The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch (Harry Stebbings)

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support.

Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science. 

Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity’s potential.

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC.

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages.

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses.

Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. 

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016.

In Today's Episode We Discuss:

1. Foundational Models: Analysis

• Will foundational models become commoditized?
• Who are the major players? What are their different strengths?
• Who will win? Who will lose?
• How important is the size of the model vs the quality of the data?

2. Open vs Closed:

• What are the biggest pros and cons of an open ecosystem for LLMs?
• Why is it naive to think that open-source LLMs will prevail?
• What will determine which method wins?

3. An Analysis of the Incumbents:

• Why is Google the most vulnerable? What can they do to regain ground?
• Why is Apple the sleeping giant? How could they win the next wave of AI?
• What should Amazon do today to compete with Microsoft?

4. The Future: Doom and Gloom?

• Why is it ridiculous to assume AI systems want to dominate?
• Why will AI create a renaissance of creativity and human freedom?
• What role should regulation play in the advancement and progression of AI?

Rene Haas is the CEO @ Arm. The technologies that Arm creates are used in over 230+ Bn devices with everything from sensors to smartphones to servers. In 2016 Softbank made Arm it's largest ever acquisition with a reported price of $32Bn. As for Rene, he was appointed CEO in February 2022 having spent the last 8 years in numerous different roles within the company. Before Arm, Rene was Vice President & General Manager of the Computing Products Business Unit at Nvidia where he enjoyed a very successful 7 years with the team there.

In Today's Episode with Rene Haas We Discuss:

1.) Entry into Tech from Eastman Kodak:

• How did Rene make his way into the world of technology and innovation?
• What are 1-2 of the biggest takeaways from his 7 years at Nvidia?
• How did working with Jensen impact his leadership approach and philosophy?

2.) Decision-Making in Leadership:

• What is the single biggest mistake leaders make when making decisions today?
• How does Rene balance the trade-off between speed vs quality of decision?
• At what point does Rene believe leaders have enough data to make a decision?
• What does Rene know now that he wishes he had known when he started on decisions?

3.) Scaling the Org and Remaining Nimble:

• Agile: How does one retain the speed and agility of a startup when one is the size that Arm is today?
• Ambition: How does Rene as a leader inspire the same level of ambition and vision in his team when Arm is as large as it is?
• Risk: How does Rene encourage his teams to take large risks when they have so much more to lose?
• Breakage: What are the first things to break in scaling? What can leaders do to get ahead of them?

4.) Leadership 101:

• What really is strategy? What is it not? What mistakes do all leaders make when it comes to strategy?
• How does Rene define "high performance" in leadership? How has his style of leadership changed over time?
• How does Rene approach vulnerability in leadership? What are the pros and cons?

Gabriel Weinberg is the Founder & CEO @ DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. Over the last 12 years, Gabe has scaled DuckDuckGo to doing 1.6Bn private searches every month, a team of 83 full time fully remote employees, raising funding from some of the best in the business; USV and most importantly, being a profitable company. If that was not enough, Gabe has also written two phenomenal books, Traction and Super Thinking. 

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In Today’s Episode You Will Learn:

1.) How Gabriel made his way into the world of startups and came to found one of today's leading search engines and privacy companies in DuckDuckGo?

2.) Gabriel decided to raise $13M from USV 4 years into the life of DDG, why did he believe that was the right time? Why does Gabe believe that DDG never needed any primary capital? How does Gabe advise founders to think when it comes to chasing profitability early? How does Gabe view the relationship between growth and capital? Are they in conflict or aligned? What does Gabe make of the many $100M rounds getting done today?

3.) How does Gabe feel about the lack of free and open distribution today? How does Gabe strategise when it comes to channel diversification? What is the right level of marketing channel diversification to have? How do you know when to really double down on one that is working? How should founders be thinking about channel saturation rates? What have been Gabes biggest lessons on payback period over the last 12 years with DDG?

4.) How does Gabe feel about the digital advertising duopoly on the internet between Facebook and Google? Why does Gabe argue that this duo of incumbents are so much more powerful than any other prior generation of incumbents? How does Gabe think about strategies to reduce their data monopolies?

5.) DDG is 83 people and fully remote, what have been Gabe's biggest lessons on what it takes to run a fully-remote team from Day 1? What mistakes did they make? WHat would Gabe advise founders contemplating the fully remote strategy? Why does Gabe have nor formal hierarchy or org chart internally at DDG? Why is this so important for culture and employee morale?

Items Mentioned In Today’s Show:

Gabe’s Fave Book: The Advantage: Why Organizational Health Trumps Everything Else In Business

As always you can follow Harry, The Twenty Minute VC and Gabe on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kent Goldman is the Founder of Upside Partnership, one of the leading seed-stage investment firms in SF with investments in the likes of Laurel and Wolf, Digit and Lily. In 2015, he was named to the Midas Brink List. Prior to forming Upside Partnership in 2014, Kent was a Partner at seed investment pioneer First Round Capital. While there he led investments in companies including Airware, Hotel Tonight, and MemSQL. He also served on the board of Mashery (acquired by Intel). Earlier in his career, Kent was a member of Yahoo!’s corporate development team and also led business strategy for Yahoo! products generating $1 billion in annual revenue.

In Today’s Episode You Will Learn:

1.) How Kent made his way into the world of early stage investing and came to found Upside?

2.) What were the big takeaways from First Round for Kent? How has he applied those learnings to his formation of Upside?

3.) What does Kent look for in the LPs that invest in his fund? Why should founders look to learn which LPs are invested in the fund investing in them?

4.) How has Kent seen his investment decision-making process alter with time? What have been the big changes?

5.) Why does Kent believe valuation does not matter so much at the seed stage? What does really matter to him at the seed stage? How does this progress with rounds?

Items Mentioned In Today’s Show:

Kent’s Fave Blog: Howards Marks: Oaktree Capital

Kent’s Fave Book: A River Runs Through It And Other Stories

Kent’s Most Recent Investment: Live Neighborly

As always you can follow Harry, The Twenty Minute VC and Kent on Twitter here!

Johnny Boufarhat is the Founder & CEO @ Hopin, one of the fastest-growing companies on the planet, providing an online events platform where you can create engaging virtual events that connect people around the globe. In the last 13 months, Johnny has raised over $174M for Hopin from the likes of Accel, IVP, Slack, Northzone, Coatue, Salesforce and of course, 20VC Fund. With the funding, again in just 13 months, Johnny has grown the team from 10 people to over 210 people in 37 countries. In October of this year, Semil Shah awarded Hopin the label, "The Breakout Tech Startup Of 2020".

In Today’s Episode You Will Learn:

1.) How Johnny made his way into the world of startups and how severe health challenges led to his realisation and founding of Hopin?

2.) What have been Johnny's biggest lessons scaling the team from 10 to 235 in just 12 months? What starts to break and when? What does Johnny believe are the 3 stages of startup growth? What have been Johnny's learnings on what it takes to acquire the very best talent?

3.) Why does Johnny believe that remote has so fundamentally changed the game? How does remote culture differ from physical culture? What advice does Johnny have for those shifting from physical to remote? Where does Johnny see so many make mistakes with the remote model?

4.) Why does Johnny believe fundraising is a game of leverage? How does Johnny advise founders to structure their raise? Should they shop their term sheets around? Should founders always be raising? How should they think through a pre-emptive round? How does COVID change the world of fundraising?

5.) What does the world of virtual events look like in a post COVID world? What events will remain virtual? What will not? How does Hopin expand beyond purely events into the much wider "connection" space? How does that look both from M&A and product expansion?

Item’s Mentioned In Today’s Episode

Johnny’s Favourite Book: Nineteen Eighty-Four

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Andrew Parker is a General Partner @ Spark Capital, one of the best performing funds of the last decade with a portfolio including the likes of Twitter, Slack, Oculus, Medium, PostMates, Cruise (acq $1Bn) the list goes on. As for Andrew, he has led Spark’s investments in Carta, Kik, PanoramaEducation, Socratic, Splash, Particle and Quantopian. Prior to joining Spark in 2010, Andrew was a member of the investment team at Union Square Ventures. Before becoming an investor, Andrew did UI design and user-experience testing at Homestead Technologies and was a web developer at Groupspace.org.

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS.

Josh Wolfe is the Co-Founder and Managing Partner @ Lux Capital, the fund that supports scientists and entrepreneurs who pursue counter-conventional solutions to the most vexing puzzles of our time, the more ambitious the project, the better. Josh is a founding investor and board member with Bill Gates in Kymeta, making cutting-edge antennas for high-speed global satellite and space communications. In 2008 Josh co-founded and funded Kurion, the company was among the first responders to the Fukushima disaster. In February 2016, Veolia acquired Kurion for nearly $400 million—more than 40 times Lux’s total investment.

In Today’s Episode You Will Learn:

1.) How did Josh make his way into VC from the science lab? What was it about venture that got Josh hooked?

2.) How does Josh view the rise of thematic investing? Why does Josh believe there are a lot of tourist VCs who are going to lose a lot of money?

3.) Investing in such frontier technologies, how does Josh view market creation? How does Josh look to build a thesis and a methodology when investing in a company without an existing market?

4.) What is the inflection point for Josh for when heavy science and R&D becomes investable? What is that tipping point where science becomes commercialized?

5.) Does Josh get concerned that with such heavy IP and corporations not investing in R&D that this is a market for acquihires? What are the pros and cons of this shortened liquidity cycles?

Items Mentioned In Today’s Show:

Josh’s Fave Book: Sapiens

Josh’s Fave Blog: Media Redefined

Josh’s Most Recent Investment: Recursion Pharmaceuticals

As always you can follow Harry, The Twenty Minute VC and Josh on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Bill Gurley is a General Partner @ Benchmark Capital, Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow.

Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.

Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. 

Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades.

Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade.

Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify and many more incredible companies.

Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and many more.

In Today's Episode You Will Learn:

1.) How does the current environment compare to prior busts?

2.) How will the changing interest rates impact the startup funding climate moving forward?

3.) Why is the rate of inflation the only true metric which reveals the ultimate fate of the economy?

4.) What are the world's leading investors telling their founders?

5.) How are the best investors in the world thinking through reserves management?

In today's show I am joined by the immensely talented Nicolas Michaelsen, Founder & CMO at AirHelp, the go to place if you have grievances during air travel. Nicolas draws back the curtain on the exclusive world of Y Combinator, this includes the admissions process, the infamous interview, the tutoring available to YC startups, the effects of YC on the valuation of startups and the key takeaways from his time at YC. 

Items Mentioned in Today's Show:

• Kevin Hale: Founded @ Wufoo, Partner @ Y Combinator
• Paul Buchheit: Creator of Gmail, Partner @ Y Combinator

In today's show you will learn:

• How Nicolas got AirHelp started?
• At what point did Nicolas realise that Y Combinator was the place to go?
• Had Nicolas considered other more local incubators?
• What was the admissions process like? Is there any specific documentation required to apply?
• How is the YC interview structured? What type of questions do the partners ask?
• What percentage of the partners need to say yes for a startup to be accepted?
• How does the tutoring system work at YC? Who did Nicolas receive as tutors for AirHelp?
• What is a typical day in the life of a YC startup?

We then finish today's episode by hearing Nicolas' thoughts on his most valuable takeaway from YC, the impact of YC on the valuation of a startup, what the future holds for AirHelp?

If you would like to follow The Twenty Minute VC on Twitter, click here!

If you would like to stay up to date with Nicolas and AirHelp, click here!

Dave McClure is the founding partner of 500 Startups, who have made over 1500 investments in the likes of Twilio, SendGrid, Intercom and Makerbot just to name a few. Prior to 500 Dave was on the investment team at Founders Fund, he also led the Facebook Fund Incubator and was Head of Marketing @ Paypal pre IPO.

In Today’s Episode with Dave You Will Learn:

• How Dave made his way into VC and came to found 500 Startups?
• Do you need unicorn exits to have significant venture returns? What is the 500 view with regards to the hit ratio of finding unicorns?
• How much ownership does 500 typically take? Does this allow Dave enough of a right to follow on in further rounds with such a small initial slice?
• How does Dave and 500 avoid the inherent signalling risk involved with their fund and accelerator? How prominent is signalling in today’s market?
• What did Dave think of Sam Altman’s statement on YC not accepting companies from other accelerators? How does Dave view YC companies?

Items Mentioned In Today’s Show:

Dave’s Fave Blog and Newsletter: Brad Feld, AVC, Mark Suster

Dave’s Fave Book: Guns Germs and Steel, The Mystery of Capital

Dave’s Most Recent Investment: Markhor

As always you can follow Harry, The Twenty Minute VC and Dave on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

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Kurt Rathmann is the Founder & CEO @ ScaleFactor, the startup providing an automated bookkeeping solution at its core, bringing all of your company’s important financial information into one place. To date, Kurt has raised over $105m with ScaleFactor from the likes of Byron Deeter @ Bessemer, Coatue, Canaan Partners, Stripes Group and Firebrand to name a few. As Michael @ Coatue told me before the show, there is no way Kurt was not going to be the founder of a bookkeeping company given his background. Prior to ScaleFacotr, Kurt was the CFO of KNS Communications and a Senior Audit Professional @ KPMG.

In Today’s Episode You Will Learn:

1.) How did Kurt make his way into the world of startups and come to found the gamechanger for bookkeeping in the form of ScaleFactor? Does Kurt believe that Founders do need to be mission-driven or can founding a company be a more analytical exercise?

2.) How did it come to be that Kurt raised 3 separate funding rounds and over $105m in just 13 months? How does Kurt feel about the saying, "when there is money on the table, take it"? Having had his B and C pre-empted, how does Kurt feel about the rise of pre-emptive rounds today? How did Kurt approach the mental challenge of transitioning from resource-starved to relative resource abundance? Was that tough to do?

3.) What is Kurt's biggest advice to founders when it comes to investor selection? What does Kurt believe are the 5 things that VCs can do to add value? Why does Kurt believe it is the responsibility of the founder to extract that value from the VC? What can founders do to really get the most out of their investors? What has Kurt found to be the biggest value from his cap table? Where do founders think VCs add value but they do not?

4.) What are some very unique and deliberate things that Kurt does to create an amazing culture at ScaleFactor? How does he advise on creating great energy in the office itself? How does Kurt think about retaining that core ethos with the expansion to multiple offices? What have been some of the biggest challenges in scaling communications internally?

5.) Does Kurt believe that being outside of a core tech hub severely limits his ability to hire the best talent? What do founders outside of these hubs need to very strategically do? How does being outside of a core hub also impact how Kurt thinks founders need to approach fundraising? What specifically can they do to increase their odds?

Items Mentioned In Today’s Show:

Kurt’s Fave Book: The Empowered Challenger Playbook: How Brands Can Change the Game, Steal Market Share, and Topple Giants

As always you can follow Harry, The Twenty Minute VC and Kurt on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Stephan von Perger is an Early Stage VC at Wellington Partners where his primary role is identifying investment opportunities and building lasting relationships with the entrepreneurs behind these companies. Stephan started his career at McKinsey before moving to Stylistpick.com as Head of Operations, he then progressed to setup and run the business operations at CityMapper.com. In today's interview Stephan walks us through the pitching process from the first email to signing the term sheet!

In Today's Episode You Will Learn:

• How and why Stephan made his move from the world of startups to the venture industry?
• What are the right reasons for a founder to enter a round of venture funding?
• How should founders go about meeting and connecting with VCs? What can founders actively do to position themselves well and how should founders phrase their emails and communication?
• Are there any aspects or buzzwords in emails which instantly make VCs interested?
• What documentation is required for the initial meeting? Is there anything founders must bring?
• How can founders make the most out of their meeting with VCs? Are there any questions founders should ask? How should founders respond to a question they do not know the answer to?
• What happens if a VC says they will contact you but a week later the founder has heard nothing? What should the founder do?

We then finish todays episode with a quick fire round where we hear Stephan's thoughts on which pitch or communication has impressed him the most, what single thing Stephan most looks for in founders and his most recent investment and why he said yes?

Peter Weijmarshausen is the CEO and Co-Founder of Shapeways, the world’s leading 3D printing marketplace and community. Shapeways have raised funds from some of the world's leading investors including the likes of USV, Andreesen Horowitz and Index Ventures just to name a few. Prior to Shapeways, Peter was the CTO of Sangine, where he and his team designed and developed satellite broadband modems. Peter was also Director of Engineering at Aramiska, where he was responsible for delivering a business broadband service via satellite.

In Today’s Episode You Will Learn:

1.) How Peter made his way into startups and came to found Shapeways?

2.) Where are we in the 3D printing cycle today? Has it developed slower or quicker than Peter expected? How was it for Peter inhabiting a space with so much hype?

3.) When does 3D printing make the transition from early adopter market to mass market? What are the determinants that will allow for this to happen?

4.) Having started life in an incubator, why did Peter decide that for the origin of Shapeways? What are the benefits? What type of founder is this model right for?

5.) Shapeways have raised from Index, USV and a16z, so how was the fundraising journey for Peter? What would he like to improve upon for next time? What did he do well?

Items Mentioned In Today’s Show:

Peter’s Fave Blog: New York Times

Peter’s Fave Book: Leadership and Self-Deception

As always you can follow Harry, The Twenty Minute VC and Peter on Twitter here!

Fred Destin is a Founding Partner @ Stride.VC, one of Europe's newest seed funds with a portfolio including the likes of Cazoo and Forward Health. Over his 17 year career in venture, Fred has established himself as one of Europe's leading VCs with the exit value of 3 of his portfolio companies alone last year totalling more than $4.5Bn with PillPack's $1Bn sale to Amazon, Zoopla to Silverlake for $3Bn and Integral Ad Science to Vista for $850m. Fred has also led investments as a General Partner @ Accel in Deliveroo, the world leader of food on demand and Carwow, the number 1 for new car sales in the UK.

In Today’s Episode You Will Learn:

1.) How Fred made his way into the world of venture and early stage? What was behind his decision to leave Accel to found Stride with Harry?

2.) Why does Fred think many today misunderstand "risk" in venture? How does that apply across the portfolio? Does Fred agree with Brian Singerman, "venture is a game of upside maximisation"? What risks does Fred define as acceptable vs non-acceptable risks? How does Fred really look to strength test the quality and depth of a founder pre-investment? What are the benefits of going through conflict early?

3.) How does Fred think about price sensitivity? What are the core questions a VC can ask when considering the pricing of an opportunity? How does Fred think about reserve allocation? How does Fred analogize this to the best traders? To what extent does TAM play a dominant role in Fred's evaluation? What does Fred mean when he says "we have to remember, we are the ones that get picked also"?

4.) How does Fred think about and assess innovation within venture? How does Fred perceive the role of data to impact venture over the coming years? Why does Fred believe it is exaggerated that data will disrupt the early stage in the coming years? Where would Fred like to see further innovation in the mechanics of venture?

5.) What does Fred believes separates the good from the great when it comes to board members? How can board members create an environment where the entrepreneur feels they can say all that is wrong? Where do many board members go wrong? Why are board members so wrong to bash a founder for missing their numbers? Why does Fred believe that plans are fiction? WHy is the framework of the plan what really matters?

Items Mentioned In Today’s Show:

Fred’s Fave Book: Man's Search for Meaning

As always you can follow Harry, The Twenty Minute VC and Fred on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Apurva Mehta is the Managing Partner @ Summit Peak Investments, investing in early stage venture capital funds and making direct co-investments. To date they have backed the likes of Raymond Tonsing, Lachy Groom and Josh Buckley to name a few on the fund side and then on the direct side, invested in Airtable, Virta Health and Sourcegraph. Prior to founding Summit Peak, Apurva spent 7 years as the Deputy Chief Investment Officer at Cook's Children's Hospital and before that spent 3 years as Director of Portfolio Investments at The Juilliard School.

In Today’s Episode You Will Learn:

1.) How did Apurva make his way into the world of fund investing? How did that lead to his founding Summit Peak and also becoming a GP?

2.) How does Apurva think about how much importance to place on references when diligencing managers? What reference types mean a lot? Which mean less? Why does Apurva still believe early-stage is the most inefficient segment of the venture landscape?

3.) How does Apurva think about GP commits? Is it fair to have a required benchmark? How does Apurva advise founders on LP concentration limits? When is one LP too much of a fund? How does Apurva advise managers on selling a stake in the management company?

4.) As a fund of funds, how does Apurva approach fund portfolio construction today? How does this differ between the fund portfolio vs the direct portfolio? How does Apurva think about the compression of fundraising timelines both with GPs and Founders? Why does Apurva believe founders at the early-stage care less about firm brand today?

5.) How does Apurva feel about investing in managers he has not met in person? How does the GP/LP fundraising process need to change? How does COVID change the fundraising process for venture funds? How will LPs react to these changes?

Items Mentioned In Today’s Show:

Apurva’s Fave Book: Principles: Life and Work by Ray Dalio

Apurva's Most Recent Investment: Sourcegraph

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Eric Paley is the Managing Partner at Founder Collective, one of the world's most successful seed funds with investments in the likes of Uber, Hunch, Makerbot and About.me. Prior to Founder Collective, Eric was the Co-Founder and CEO of Brontes Technologies, later acquired by 3M for $95m. Following it’s acquisition Eric began making angel investments and it was not long before Eric and David, 'super angel' at the time, saw the potential for a Founder First seed fund and Founder Collective was born.

In Today's Episode You Will Learn:

1.) How Eric made his move into the wonderful world of venture from founding Brontes Technologies?

2.) What does Eric make of early stage valuations? When creating a venture fund why did Eric believe the seed stage was the stage with the most opportunity?

3.) Question from the legend, David Hornik @ August: At such an early stage where Founder Collective traditionally put in $0.1m-$0.3m, does Eric feel they put in enough money to make it matter?

4.) Does Eric believe that by not doing follow on rounds they are missing out? Does this resistance to seed funds set Founder Collective apart? David did mention that you have begun to follow on now, so what makes you follow on with one portfolio company and not another?

5.) The Founder journey is testing both physically and emotionally, what elements of support do Founder Collective provide outside of the business relationship?

Items Mentioned In Today's Show:

Eric's Fave Book: Fooled By Randomness

As always you can follow Harry, The Twenty Minute VC and Eric on Twitter here!

If you would like to see a more colourful side to Harry with many a mojito session you can follow him on Instagram here!

Ryan McIntyre is a Co-Founder @ Foundry Group, one of the leading VC funds of the last decade with investments in the likes of Fitbit, SendGrid and Makerbot. Prior to Foundry, Ryan started his career in VC at Mobius Venture Capital in January 2000.  While at Mobius Venture Capital, Ryan led the firm’s investments in Postini (acq. GOOG) and Sling Media (acq. DISH). Prior to Mobius, Ryan co-founded Excite in 1993, which went public in 1996 and later became Excite@Home following the $6.7 billion merger of Excite and @Home in 1999. At the time this acquisition was the largest internet transaction to date and created a company that achieved peak revenues of $616 million in 2000.

In Today’s Episode You Will Learn:

1.) How Ryan made his way into the wonderful world of VC and came to co-found Foundry?

2.) At what moment did Ryan realise that he wanted to be a VC rather than his previous life of an entrepreneur? What was the catalyst moment for Ryan?

3.) What does the investment decision making process look like @ Foundry Group? What are the benefits and challenges of implementing such a model?

4.) What are the fundamentals to creating a successful venture partnership? How important is differing skill sets and contrarian thinking?

5.) What makes the great board members to Ryan? How has Ryan seen his style of being a board member alter over the time he has been on boards?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: Dune by Frank Herbert

Investment Ryan Is Most Excited By: Sendgrid

As always you can follow Harry, The Twenty Minute VC and Ryan on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Nektarios Liolios is Co-Founder and Managing Director of Startupbootcamp Fintech, the leading innovation program in the financial industry providing access to a global network of investors and VCs for up to 10 lucky startups selected. Nektarios himself has more than 15 years in business, having spent the last three with InnoTribe, running the Innotribe Startup Challenge.

Items mentioned in today's show:

• 500 Startups: How to Pitch
• investUP: The Crowdfunding Supermarket

What you will learn in today's episode:

• How Nektarios got into the world of tech accelerators?
• How Startupbootcamp Fintech varies from the traditional VC model?
• What makes the best pitches at Demo Days?
• What is the selection process to get accepted at Startupbootcamp?
• What can startups prepare to do before pitching to Startupbootcamp?
• What is the most common reason Nektarios says no to startups?
• What would Nektarios advise someone who is looking to find a co-founder?
• What sector is Nektarios most excited about for the future?
• What Nektarios thinks about the future of bitcoin?

We then complete todays interview by having a quicker round where we hear Nektarios' thoughts on his favourite entrepreneur? The happiest moment Nektarios has enjoyed in his career? A day in the life of a Managing Director of a Startupbootcamp? What was Nektarios' most recent investment and why he said yes?

For all the resources mentioned in today's show, head on over to www.thetwentyminutevc.com

For any suggestions about future guests or questions you would like to hear, we would love to hear from you. If so email harry@thetwentyminutevc.com

David Frankel is the Managing Partner at Founder Collective, one of the world's most successful seed funds with investments in the likes of Uber, Hunch, Makerbot and About.me. Prior to Founder Collective, David was the Founder and CEO of Internet Solutions, one of the largest ISP providers in Africa. Following it’s acquisition David made his move into the investing game becoming one of the very first ‘super angels’, following exceptional success in this field, David along with Eric Paley (coming on the show on Wednesday) and Micah Rosenbloom founded Founder Collective, a seed stage venture fund whereby everyone at Founder Collective has started a technology company, they have lived and breathed the founder experience, a true founder friendly venture fund.

In Today's Episode You Will Learn:

1.) How did David make his move into the wonderful world of venture from being a founder and 'super angel'?

2.) Question from Spencer Lazar @ General Catalyst: How has David evolved as an investor over time? Has his strategy and approach altered?

3.) David has experienced some immense cycles both up and down, how has he seen the seed funding environment evolve?

4.) What was it like working with Chris Dixon from a16z? What advice would David give to someone looking to maintain or create a network around them? What other sources of deal flow do you utilize? How do you most like to be approached?

5.) How did FC's investment in Uber come about? What does David make of the regulatory hurdles Uber face with regards to employees or contractors? What is the future for Uber?

6.) What can we expect from Founder Collective? What is David excited about and why?

Items Mentioned In Today's Show:

David's Fave Book: Eating Well For Optimum Health, Playing The Enemy

David's Fave Blog: Dan Primack, Term Sheet

David's Most Recent Investment: Pillpack

As always you can follow Harry, The Twenty Minute VC and David on Twitter here!

If you would like to see a more colourful side to Harry with many a mojito session you can follow him on Instagram here! 

Jenna Brown is the Founder & CEO @ Shipamax, a data driven communications platform for brokers and operators. They recently raised their seed round from the likes of FF Angel, Y Combinator, Cherubic Ventures, and top angels including Lee Linden and my personal favorite, Andy Rankin. Prior to Shipamax, Jenna was Head of Global Expansion @ GoCardless, one of London's leading Fintech players and before that was herself a trader at RWE Trading.

In Today’s Episode You Will Learn:

1.) How Jenna made her way from ship broker to YC alum, changing the world of shipping with Shipamax?

2.) How does Jenna compare fundraising in the UK to Europe? Was it a challenge raising US funds, considering Jenna was operating outside of the valley? How did Jenna look to mitigate these concerns?

3.) How did Jenna experience both direct and indirect sexual discrimination throughout the fundraising process? Which form was harder to deal with? How did Jenna respond? In hindsight, would Jenna have done anything differently?

4.) What does Jenna advise founders in terms of taking operator VC money vs non-operator VC money? What differing questions must be asked? What should founders be wary of with both types of investors?

5.) Why does Jenna disagree with the commonly held suggestion that you must get people to pay for your product as soon as possible? Why is this not the case always? In what cases is it optimal to have a smoother and faster onboarding?

Items Mentioned In Today’s Show:

Jenna’s Fave Book: Hard Thing About Hard Things

Jenna’s Fave Blog: SaaStr

As always you can follow Harry, The Twenty Minute VC and Jenna on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

WePay helps online platforms increase revenue through integrated payments processing, helping platforms offer ROI-positive integrated payments to their users - within their UX and without taking on fraud & regulatory exposure. WePay also offers award-winning support and can even work with your team thru Slack or Zendesk. Get the payments revenue you want, without getting bogged down every time a user has a payments question. Simply visit wepay.com/harry

PipeDrive is the Sales CRM and pipeline management software to use, with the primary view being the pipeline a clear visual interface that prompts you to take action, remain organized and stay in control of a complex sales process. This is why sales pros and deal makers love it (my words, not Pipedrive’s). Plus it easily lets you find the stats you need and is fully customizable. Even better, you can signup for free on here it really is a must.

Emilie Choi is the President and Chief Operating Officer @ Coinbase, the easiest place to buy and sell cryptocurrency. Prior to their IPO earlier this year, Coinbase raised funding from some of the best in the business including USV, a16z, Initialized and Ribbit to name a few. As for Emilie, before Coinbase she was Head of Corporate Development for @ LinkedIn and before Linkedin served in various positions at Warner Bros., including as Manager of Corporate Business Development and Strategy. If that was not enough, Emilie currently serves on the board of Naspers and ZipRecruiter.

In Today’s Episode with Emilie Choi You Will Learn:

1.) How Emilie made her way into the world of startups, came to lead Corp Dev @ Linkedin and how that led to her joining forces with Brian @ Coinbase as COO & President? What lessons did Emilie learn from Reid Hoffman and Jeff Weiner that she has taken with her to Coinbase?

2.) Corp-Dev Guide: Why are so many startups trying to hire Head of Corp Devs today? What are the signals that suggest now is the right time? How would Emilie structure the process of hiring a Head of Corp Dev? What questions should be asked? How can you test their skills? What mistakes do CEOs often make when hiring Head of Corp Devs?

3.) COO Guide: What does the role of COO really mean to Emilie? How does Emilie advise founders on whether they do actually need a COO? How would Emilie structure the process of hiring a COO? What are some common red flags that concern Emilie when hiring COO's? What is the right relationship between CEO and COO?

4.) Resource Allocation: How does Coinbase think about internal resource allocation between core product and their venture products? What was the thinking behind Coinbase Ventures? Why do they have no full-time staff? What is the core objective of the fund? Why does Emilie think it will be one of the best performing funds in venture?

Item’s Mentioned In Today’s Episode with Emilie Choi

Emilie’s Favourite Book: The Secret History

Roger Dickey is the Founder & CEO @ Gigster, the smart development service combining top developers and designers with artificial intelligence. They have raised over $30m in funding from the likes of a16z, Redpoint, Marc Benioff, Ashton Kutcher, Michael Jordan and then previous guests Rick Marini and Felicis Ventures. Prior to Gigster, Roger founded Mafia Wars, where he built the business to $1Bn in revenues and 100m users. Roger is also a prolific angel investor and LP in venture funds with a portfolio including the likes of Docker, ClassDojo and Addepar, just to name a few. If that was not enough Roger is also an advisor to 8VC, Lemnos Labs and OpenDoor.

Marc Benioff is one of the iconic founders and visionaries of our time. From the founding of Salesforce 25 years ago, Marc has in many ways created an entire industry. He has scaled the company to a market cap of $346BN, $38BN in revenue and over 72,000 employees. 

Ask Me Anything with Marc Benioff: 

The Future of Models:

1. Why does Marc believe we are at the upper end of LLMs and they are commoditising?

2. Why does Marc believe the future of models is many smaller, verticalised models specialised in different areas?

3. OpenAI vs Anthropic vs Xai. Which would Marc buy and which would he short?

4. What is the single biggest barrier to Salesforce winning the AI war in the next 10 years?

The Future of Agents:

5. What does Salesforce need to do to prevent becoming a database in the next generation of AI? 

6. To what extent do agents hurt vs help Salesforce?

7. What do very few people understand about agents that is very important?

The Future of Labour: 

8. Will Salesforce replace it’s human labour with digital labour? Will Salesforce be bigger or smaller in 10 years time, people wise?

9. Why does Marc believe that layoffs are a crucial tool for CEOs to win?

10. How will a future of digital labour change the pricing model of SaaS tools today?

Management Lessons from Marc Benioff:

11. How did one meeting with Steve Jobs change how Marc views leadership?

12. How does Marc analyse the required mindset to win as a CEO today?

13. What has Marc changed his mind on most in the last 12 months?

Daniel Dines is the Co-Founder @ UiPath, one of the most incredible journeys in startups. For 10 years, UiPath was a bootstrapped company that scaled to just $500K in revenue. Then it all changed, product market fit became obvious and the rest is history. The company went on to raise funding from Sequoia, Accel, Kleiner Perkins and more. Today, the company is worth over $10BN, listed on the NASDAQ and does $1BN+ in revenue.

In Today's Episode with Daniel Dines We Discuss:

1. From a Dollar a Day to Romania's Richest Man:

• How would Daniel's parents and teachers have described the young Daniel?
• How did Daniel first learn to code? Why was his first programming job on $300 per month the best?
• How did Daniel learn English by playing bridge with his friends?
• What was the a-ha moment for Daniel with UiPath?

2. Becoming a Billionaire: The Mental Journey:

• What does Daniel mean when he says everyone is a prisoner of their own mind?
• How does Daniel reflect on his own relationship to money?
• How did having absolutely nothing impact Daniel's relationship to risk?
• Why does Daniel think that he does not really experience or feel happiness?

3. 10 Years to $500K ARR: The Miracle Bootstrapping Journey:

• After 10 years, UiPath had just $500K in ARR, what was the one single moment that changed everything in 2014?
• How did raising the seed round change everything for Daniel? How did it change his approach to operating?
• What was the impact of having Sequoia invest? Does it change the game? Why did Daniel say no to them the first time they tried for the Series B?

4. Journey to a $10BN Public Company: The Crucible Moments:

• How did the company almost go bust when it spent $400M against a plan of $150M in 2021?
• What is the single proudest moment Daniel has of the 19 year journey with UiPath?
• What have been Daniel's biggest management lessons in scaling UiPath to $1BN in ARR?
• Knowing all that Daniel does today, what would he have done differently about the UiPath journey?

Mark Suster is Managing Partner at Upfront Ventures which he joined in 2007, having previously worked with Upfront for nearly 8 years as a two-time entrepreneur. Before joining Upfront Mark was Vice President, Product Management at Salesforce.com following its acquisition of Koral, where Mark was Founder and CEO. Prior to Koral, Mark was Founder and CEO of BuildOnline, a European SaaS company that was acquired by SWORD Group. Mark is also the writer of one of my favourite VC blogs, Both Sides Of The Table which is a centre piece to the whole VC community and is a must read for all interested in entrepreneurship and VC.

In Today's Episode You Will Learn:

1.) How did Mark make his way into the world of tech and later make the transition to VC?

2.) How have Mark's entrepreneurial origins influenced his investment style and approach to startups?

3.) What really gets Mark excited in terms of the founders and the companies they have built?

4.) How does Mark recommend that startup founders can meet investors and get those initial meetings?

5.) What sector is Mark most excited by and why?

6.) Mark has said in the past 'too much money too early often fucks companies up'. Why is that and how should founders determine what is the right amount to raise?

Items Mentioned In Today's Show:

My Fave of Mark's Posts: Entrepreneur DNA, I Invest In Lines Not Dots

Mark's Fave Book: The Accidental Superpower

Mark's Fave Blog or Newsletter: Stratechery, Ben Evans, Chris Dixon, Tom Tunguz

Mark's Most Recent Investment: Mitu Networks

As always you can follow Harry, Mark, The Twenty Minute VC and Upfront Ventures on Twitter here!

If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

Brad Hargreaves is the Founder & CEO @ Common, the startup that provides shared housing for those that live in common. They have raised over $20m in VC funding from some of our very favorites including the likes of Maveron, Slow Ventures, Lowercase Capital, 8VC and Brendan Wallace @ Fifth Wall. Prior to Common, Brad was the Founder of General Assembly, the global school for tech, business, and design which has, to date, raised over $140m and has locations across 4 continents.

In Today’s Episode You Will Learn:

1.) How Brad made his way into the world of tech, came to found General Assembly and then made his move into the world of real estate with Common?

2.) Why have we seen the price of real estate in core urban areas hit an all time high today? How does Brad think this will affect the future of malls?

3.) Why does Brad think that in a scalable business not every element has to scale? What does he mean by this? What proportion of elements have to scale? What are the inflection points in scaling that suggest potential for venture returns?

4.) How does Brad think about the secondary affects of AVs? Which areas does Brad think have the most potential for innovation? How does Brad think about the negative externalities of AV's? What can be done to mitigate their effects? 

5.) Why does Brad think that occupational licensing is one of the biggest barriers to economic growth in the US? What reform can be made to enhance this and allow for growth?

Items Mentioned In Today’s Show:

Brad’s Fave Book: The Lever of Riches

Brad’s Fave Blog: Kim Mai Cutler, Fifth Wall Newsletter, Steven Smith

As always you can follow Harry, The Twenty Minute VC and Brad on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

WePay helps online platforms increase revenue through integrated payments processing, helping platforms offer ROI-positive integrated payments to their users – within their UX and without taking on fraud & regulatory exposure. WePay also offers award-winning support and can even work with your team thru Slack or Zendesk. Get the payments revenue you want, without getting bogged down every time a user has a payments question. Simply visit wepay.com/harry

PipeDrive is the Sales CRM and pipeline management software to use, with the primary view being the pipeline a clear visual interface that prompts you to take action, remain organized and stay in control of a complex sales process. This is why sales pros and deal makers love it (my words, not Pipedrive’s). Plus it easily lets you find the stats you need and is fully customizable. Even better, you can signup for free on here it really is a must.

Mike Lazerow is a serial entrepreneur and now Co-Founder and Managing Partner @ Velvet Sea Ventures alongside his wife, Kass. Prior investments from the Velvet Sea Partners include Twitter, Square, SpaceX, Snap Inc., Facebook, Pinterest, Domo, and more. Prior to becoming an investor, Mike founded Buddy Media in 2007, selling the company to Salesforce just 5 years later for $745M. Before Buddy Media, Mike co-founded Golf.com, a multi-million dollar profitable golf media property that Mike and Kass sold to Time Inc in 2006.

In Today’s Episode with Mike Lazerow You Will Learn:

1.) How Mike made his way into the world of startups way back in 1993, how that led to Golf.com and Buddy Media? Why did he decide he wanted to be a VC? How did seeing the dotcom era fundamentally impact Mike's approach to business and investing?

2.) Why does Mike believe how you operate as an investor is more important than who you are and what you have done? How does Mike aim to invest and operate with this in mind? What are 3 core elements that Mike looks for in every deal? How does Mike approach his own investment decision-making process? How has it changed over time? How does he use gut to make decisions?

3.) What does Mike believe are his biggest insecurities as an investor? How does Mike think about the challenge of moving from a collaborative angel to a competitive VC? How does Mike think about the importance of ownership today? What has Mike learned about how the best VCs engage with round construction?

4.) How does Mike analyse his own style of board membership today? Why does Mike believe that boards are more helpful for the entrepreneur than for the investor? As an entrepreneur, how did Mike prepare for his boards? How does Mike advise founders to get the most out of their boards? Where do many make mistakes? How can one optimize the board member/founder relationship?

5.) Why does Mike believe that "having sex with your partner is a feature, not a bug"? How do Kass and Mike work together in such a complementary fashion? How do they ensure that personal matters never intrude on work decisions? How does Mike think about his relationship to money today? How does Mike want to imbue the same hard work and ethics to his children?

Item’s Mentioned In Today’s Episode with Mike Lazerow

Mike’s Favourite Book: Man's Search for Meaning

Mike’s Most Recent Investment: LeoLabs

Scott Kupor is Managing Partner @ Andreessen Horowitz, one of the world's most renowned venture funds with a portfolio including the likes of Facebook, Airbnb, Github, Lyft, Coinbase, Slack and many more. As for Scott, he has been with the firm since its inception in 2009 and has overseen its rapid growth, from three employees to 150+ and from $300 million in assets under management to more than $7 billion today. Before a16z, Scott was a VP @ HP where he managed a $1.5 billion (1,300 person) global support organization for HP Software product portfolio. Scott joined HP as a result of his prior company Opsware, being acquired, where he served as a Senior VP across numerous roles across an incredible 8-year journey. 

In Today’s Episode You Will Learn:

1.) How Scott made his way from the world of law to startups to being Managing Partner at one of the world's most renowned venture firms in the form of a16z?

2.) How did seeing the boom and bust of the dot com bubble and 2008 impact Scott's operating mindset today? Why does he argue that those times are so drastically different to today? How do public markets fundamentally diffferent? How do teams approach to capital efficiency and scaling differ significantly?

3.) What does Scott believe entrepreneurs get most wrong when pitching VCs? Why does Scott argue that product is not the core when pitching VCs? Does Scott agree with Fred @ Okta in weighing it: 70% market, 20% team, 10% product? What is Scott's weighting? Why does Scott believe that the compression of fundraising timelines is a problem? What pitch sticks out to Scott above all others? What made it so memorable?

4.) How does Scott advise founders on determining the right amount to raise for? Does Scott believe that founders should ask for a specific number or a range? Why does Scott believe raising for "runway" is the wrong mindset? Does Scott believe that most bridges are bridges to nowhere? If so, what is the next step? How does one relay that information to the founders?

5.) What have been some of Scott's biggest learnings from building the firm with Marc and Ben? What does Scott believe have been the biggest inflexion points in the public status of a16z? What have been the biggest challenges for Scott in the scaling of the firm? How does he foresee that changing in the future?

Items Mentioned In Today’s Show:

Scott’s Fave Book: Master of the Senate: The Years of Lyndon Johnson

As always you can follow Harry, The Twenty Minute VC and Scott on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Angela Strange is a General Partner at Andreessen Horowitz, one of the leading venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Airbnb, Asana and more. As for Angela, she largely focuses on investments in financial services and a16z has made significant investments in LATAM in the likes of Loft, Jeeves, Pomelo and Addi to name a few. Prior to a16z, Angela was a product manager at Google where she launched and grew Chrome for Android and Chrome for iOS into two of Google’s most successful mobile products.

In Today’s Episode with Angela Strange You Will Learn:

1.) How Angela made her way into the world of venture from a career of running marathons and product management at Google?

2.) Does Angela believe we are going to see regional winners in LATAM with players owning their segment for Argentina, Mexico, Brazil etc? Why does Angela believe there is a huge business to be had in catering to the unbanked? How does Angela analyze whether startups can acquire distribution before incumbents acquire innovation?

3.) How does Angela respond to the suggestion that LATAM merely produces copycat companies of Western alternatives? How does Angela respond to claims that there is a lack of viable exit opportunities with insufficient local public markets and few international acquirers in the region? Does Angela believe there is a sufficient depth of engineering talent in the region?

4.) What has been Angela's biggest miss? How did it change her investment process? How does Angela analyze TAM? Where does Angela think many make mistakes in their underwriting of market size? How has Angela learned to think through societal and behavioral changes that impact market timing (cash-based economies, COVID etc?)

Item’s Mentioned In Today’s Episode with Angela Strange

Angela’s Favourite Book: More More Than You Know: Finding Financial Wisdom in Unconventional Places

Angela’s Most Recent Investment: Jeeves

Mike Hirshland is the Co-founder of Resolute Ventures, one of the leading pre-seed and seed stage funds of the last decade having recently announced their new $75m Fund IV. In prior funds they have the likes of OpenDoor, Mixmax, Greenhouse, AppZen and more incredible companies. As for Mike, prior to founding Resolute, he founded Dogpatch Labs, the community which helped launch over 350 companies including Instagram. Before Dogpatch, Mike was a partner with Polaris Venture Partners from 1999-2011, where he was the original seed investor behind Automattic, Q1 Labs (acquired by IBM for $600 million), Quantcast and KISSmetrics.

In Today’s Episode You Will Learn:

1.) How Mike made his way from a legal clerk in the US Supreme Court to founding his own venture firm in the form of Resolute Ventures?

2.) What does Mike mean when he says Resolute invest at the "old seed stage?" What stage of development and traction are the companies at this stage? Why does seed investing out of a $Bn fund not make sense to Mike? What are the acceptable vs unacceptable risks at this stage?

3.) How does Mike think and assess portfolio construction today? How many lines in the portfolio is enough to be sufficiently diversified? How does Mike think about ownership given his thesis on diversification? How does Mike assess his own price sensitivity today? How does Mike think about loss ratio within the portfolio today?

4.) What are the ideal attributes of the founder/VC relationship to Mike? Is it right for the investor to also be friends with their founders? What can founders do to really build and deepen relationships with investors both during and outside of official fundraises? Where does Mike often see founders making mistakes here?

5.) How does Mike think about the right time to establish a board? What does Mike advise founders in terms of board composition in the early days? How does Mike look to build a sense of "board intimacy" with his founders? Why does Mike believe that there is a "counter-productivity to boards at seed"?

Items Mentioned In Today’s Show:

Mike’s Fave Book: A Little Life

As always you can follow Harry, The Twenty Minute VC and Mike on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company.

In Today's Episode with Ryan Akkina We Discuss:

1. From Engineer to LP with MIT:

• How did Ryan make his way into the world of fund investing as an LP with MIT?
• Why did he turn down the chance to be a VC early in his career?
• What does Ryan know now that he wishes he had known when he started at MIT?

2. The Manager Evaluation Process for MIT:

• What does Ryan look for most when investing in new managers?
• How important is track record when evaluating a new manager?
• What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process?

3. How MIT Builds Their Portfolio:

• How does MIT construct their portfolio from private to public to everything in between?
• What are the three different types of check sizes that MIT writes when investing in new managers?
• What are the most common reasons why MIT will not re-up with a manager?
• What are the single biggest reasons why great managers turn bad?

4. MIT: The Direct Investor:

• Why does MIT see so much opportunity in direct investing?
• How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process?
• How do MIT think about the right number of direct deals to make up their portfolio?
• How do they approach check sizing on a per-company direct investment?
• What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset?

5. LP Markets Today and Where We Go From Here:

• Are LPs open for business today? What type of firms will not struggle? Which will?
• How does Ryan view liquidity windows today? When will M&A and IPO markets open?
• What would Ryan most like to change about the world of LPs?
• Why does Ryan believe the LP incentive structure in terms of compensation is broken?

Dennis Mortensen is the Founder & CEO @ X.ai, the startup that realises scheduling sucks and provides ridiculously efficient AI software that solves the hassle of meeting scheduling. To date, Dennis has raised over $44m in VC funding from the likes of Firstmark, IA Ventures, Lerer Hippeau, DCM and more fantastic names. As for Dennis, he is an expert in leveraging data to solve enterprise use cases and prior to X.ai he was the Founder & CEO of 3 companies, 2 of which were acquired and one which went bust or as he describes a rather expensive MBA. Dennis is also the author of Data Driven Insights, on collecting and analyzing digital data.

In Today’s Episode You Will Learn:

1.) How Dennis made his way from Copenhagen to New York, the world of startups and came to found one of the hottest AI companies of our day in X.ai?

2.) What were Dennis' biggest lessons from enjoying 3 successful exits prior to X.ai? What were Dennis' learnings from his one failed startup? What would he do differently if he were to start another company? How does Dennis navigate the balance of between pursuing a vision and miss vs when something is just not working?

3.) Does Dennis believe that there really is such a thing as an AI first company? What is the right mentality to approach a company solving a problem through AI with? How does Dennis view the standardisation of AI tools today (Tensor Flow, libraries etc etc)? Does this remove barriers and defensibility for AI companies? What is the key to success for all AI companies?

4.) What does a truly differentiated data acquisition strategy look like? How can one determine the different utility value between different sizes of data? At what point does Dennis believe utility value of data diminishes due to the sheer size of existing data?

5.) Does Dennis believe that conversational UI is truly a paradigm shift in the way we interact with our devices or an iterative improvement? What have been some of the biggest lessons for Dennis in designing conversational UI products? What have been some of the fundamental challenges?

Items Mentioned In Today’s Show:

Dennis’ Fave Book: The Narrow Road: A Brief Guide to the Getting of Money, Shoe Dog: A Memoir by the Creator of NIKE, Mike Tyson: Undisputed Truth

As always you can follow Harry, The Twenty Minute VC and Dennis on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steve Pagliuca is a Senior Advisor at Bain Capital, the firm he joined in 1982 and as a Managing Director of Bain Capital, he has helped build the firm into one of the world’s leading investment companies with over $160 billion in assets under management. Steve is also a Managing Partner and Co-Owner of the World Championship Boston Celtics Basketball franchise. Steve is also co-owner and co-chairman of the Serie A professional football club, Atalanta Bergamasca Calcio. If that was not enough, Steve currently, serves on the Board of Directors of Burger King, Gartner Group, HCA, Warner Chilcott, and FCI. Huge thanks to Moshe @ Shrug Capital for making the intro.

In Today's Episode with Steve Pagliuca We Discuss:

1.) From Duffel Bags at Duke to Buying Sports Teams:

• How Steve went from having a single duffel bag arriving at Duke University to entering the world of private equity with the founding of Bain's PE funds?
• Did Steve always know he would be successful? What does Steve think about the importance between luck and timing?
• How did Steve's mother impact how he approaches parenting and self-belief with his children?

2.) Buying Sports Teams: Not So Different to Companies:

• When buying and running a sports team, what is the same, and what is different from buying and running a company?
• What is Steve's biggest advice to new owners of sports teams?
• What are the single biggest mistakes sports team owners make when they buy a team?
• What happened with the Chelsea bid? Why did Steve lose? How did debt change the deal?

3.) The Future of Sports Ownership:

• Why does Steve believe we have seen a massive rise in American and private equity buyers of both global sports teams but also European sports teams?
• How has "new media" changed the inherent value that can be placed on a team? Why does it change the value? Which forms of "new media" are most important?
• How much further can the value of these sports teams increase?
• Does this massive increase in the price and assets of certain clubs not lead to a massive inequality in sports? What can be done to prevent this imbalance?

4.) Steve Pagliuca: The Person and Capital Allocator:

• What is the single best investment advice Steve has ever received?
• How does Steve think about his relationship to wealth today? How has it changed over time?
• What does it take to have an amazing marriage and be at the top of your profession?
• What were 1-2 elements that made Bain able to scale to the proportions of AUM that they have done? What would he have done differently?

AJ Tennant is the Vice President of Sales & Success at Glean, Glean has more than 20x'd its revenue and 100x'd its user base in the just two and a half years he's been there. Before Glean, AJ had incredible runs at Slack and Facebook. At Slack, AJ helped grow revenue from $6 million to more than $1 billion. 

In Today’s Episode with AJ Tennant We Discuss:

1. How to Sell AI Tools in 2024:

• Are we still in the experimental budget phase for AI?

• How does selling AI tools differ to selling traditional SaaS?

• What are enterprises biggest concerns when it comes to adopting AI tools?

• What buzzwords get enterprises most excited in the sales process?

• Will we see a massive churn problem when the first renewal cycle for many of these AI products comes?

2. Outbound, Discounting, Closing:

• Is outbound dead in 2024? What does no one do that everyone should do?

• How does AJ approach discounting? Biggest lessons and advice?

• What can sales teams do to create a sense of urgency in a sales cycle?

• How does AJ do deal reviews and post-mortems? What is the difference between good and bad post-mortems?

3. How to Master Customer Success:

• What are the biggest mistakes founders make today in managing their CS teams?

• Should CS be compensated for upsell? How should the comp structure of CS teams change?

• What can be done to create a good handoff experience for the customer when handing from AE to CS?

• What are the most common ways CS teams break over time?

4. Hiring the Best Sales Teams:

• How does AJ structure the hiring process for all new sales hires?

• What questions does AJ always need to ask when hiring sales reps?

• What are clear signs of outperformers when hiring new reps?

• Does AJ give candidates a take-home assignment? What does he want to see from them?

Kyle Hill is the Co-Founder & CEO @ HomeHero, one of the largest providers of non-medical home care in California. HomeHero has provided over 1 million hours of care to thousands of families and won "Best Employment Website of 2014". Due to this immense success Kyle has been on CNN, Forbes, Wall Street Journal and many more. HomeHero has raised funds from some of the world's best investors including Chamath & Mamoon @ Social Capital, Jason Calacanis @ TWIST and Peter & Michael @ Science Inc.

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In Today’s Episode You Will Learn:

1.) How Kyle came to found HomeHero? What was the a-ha moment for him?

2.) Question from Mamoon @ Social Capital: Considering that this is not your typical software business; being largely people centric, how does Kyle think about the profitability of such a business?

3.) How much of a role does unit economics lay in the mind of Kyle? How does Kyle look to balance growth with profitability?

4.) How was the fundraising process for Kyle with Chamath & Mamoon @ Social Capital? What did Kyle do to prepare for the pitch? What did Kyle do well? What would Kyle look to improve upon? How would Kyle like VCs to treat him as a Founder?

5.) ?

Items Mentioned In Today’s Show:

Kyle's’s Fave Book: Black Swan

Kyle’s Fave Blog: The Best Designs.com

Scott Dietzen is Vice Chairman of the Board of Pure Storage and served as the Company’s CEO from 2010 to 2017. Under his leadership, Pure grew to thousands of employees and
completed an IPO in 2015. Dietzen is a four-time successful entrepreneur with WebLogic, Zimbra, and Transarc. Before Pure, he was President and CTO of Zimbra (now part of VMware), but originally acquired by Yahoo!, where Dietzen served as interim SVP of Communications and Communities. Prior to Zimbra, Dietzen was CTO of BEA Systems, where he helped craft the technology and business strategy for WebLogic that drove BEA from $61m in annual revenues prior to the WebLogic acquisition to over $1B.

In Today’s Episode with Scott Dietzen You Will Learn:

1.) The Journey to Pure Storage CEO:

• How did Scott make his way into the world of tech and startups?
• What was the hardest element of making the transition from CTO to CEO?
• What advice would Scott give to more technical leaders looking to make the move to CEO? Where do so many make mistakes?

2.) How To Build Trust in a Team:

• What are the most important ways that leaders can build trust with their teams?
• How can leaders be honest and share the hard truths without damaging role?
• What is the right tone to communicate both the big wins and big losses?
• Why does Scott always believe the losses teach more? How does Scott approach post-mortems?

3.) The Biggest Mistakes Founders Make:

• What are the single biggest hiring mistakes that founders make?
• What are the single biggest firing mistakes executives make?
• Why should founders sometimes say no to customers?
• How should founders approach investor selection and valuation for rounds?

4.) How to Optimise a Board:

• What specifically can founders do to optimise their board?
• What are the biggest errors founders make when communicating with their board?
• What is the value per word framework? How does it tell which board member is the best?

Item’s Mentioned In Today’s Episode with Scott Dietzen

Scott’s Favourite Book: The 22 Immutable Laws Of Marketing

Kevin Niparko is the VP of Product @ Twilio. Kevin joined Twilio through the acquisition of Segment where he spent an incredible 8 years in numerous different roles including as Head of Product. Before entering the world of product, Kevin was a Management Associate at the world-renowned, Bridgewater Associates.

In Today's Episode with Kevin Niparko We Discuss:

1. From Bridgewater to Head of Product:

• How Kevin made his way from the world of asset management and analytics to leading product teams?
• What are 1-2 of Kevin's biggest takeaways from his time at Bridgewater with Ray Dalio?
• How did the 8 year journey with Segment leading to their $3BN acquisition impact his approach to product?

2. What Makes a Great Product Person:

• Does Kevin believe that product is more art or science? If he were to put a number on it? What would it be out of 100?
• Why does Kevin believe that all product people should learn to write?
• Why does Kevin believe that the best product people are generalists and not specialists?
• Why does Kevin think that analytics is an insanely good start for product people?

3. How to Hire the Best Product People:

• How does Kevin approach the hiring process for product hires today?
• What are the non-obvious traits of hires he looks for? How does he test for them?
• Does Kevin use case studies? Where do many fall down? What do the best do?

4. Product Reviews: Good vs Great:

• How often does Kevin do product reviews? Who is invited?
• How have product reviews changed in a world where the company is now fully remote?
• What is the difference between good and great product reviews?
• What is the single best product decision Kevin has made? What did he learn?
• What is the worst product decision Kevin made? How did that change his approach?

Olaf Carlson-Wee is the Founder & CEO @ Polychain Capital, one of the world's premier funds actively managing a portfolio of blockchain assets. Having founded the firm less than 2 years ago with their initial $4m fund, Polychain now has over $200m AUM with backing from the likes of Sequoia, Founders Fund, Andreessen Horowitz and USV just to name a few. Prior to founding Polychain, Olaf was the first employee at Coinbase serving as their Head of Risk and as product manager. In addition, Olaf has also been an active angel with a portfolio including the likes of Robinhood, Ethereum and Numerai.

Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.

Marcelo Claure is the Founder & CEO of Claure Group, a multi-billion-dollar global investment firm. He is the Executive Chairman and Managing Partner of Bicycle Capital, a $500M Latin America-focused growth equity fund, and was appointed Chairman in Latin America of SHEIN, the global #1 on-demand fashion company in the world. Claure was also the CEO of SoftBank Group International where he launched SoftBank’s $8B Latin America Funds, and had direct oversight for SoftBank’s operating companies. 

Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel. 

Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets.

Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees.

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world. 

In Today's Episode on Price Sensitivity We Discuss:

1. Doug Leone: Why the attitude of "deploy, deploy, deploy will get so many in trouble"?
2. Marcelo Claure: How to know when price matters and when it does not?
3. Geoff Lewis: What is the right framework to assess price at an early stage?
4. David Tisch: How does the importance of price change vis a vis company vs portfolio?
5. Orlando Bravo: What have been Thoma Bravo's biggest lessons on price?
6. Cyan Banister: Why does Cyan believe there will be a reckoning?

Eric Glyman is the Co-Founder and CEO of Ramp, America's fastest growing corporate card and finance automation platform. Under Eric’s leadership, Ramp has raised more than $1 billion in financing, with a valuation of $8.1 billion. Prior to Ramp, Eric co-founded Paribus, a price-tracking app to help consumers save money (acquired by Capital One). Ramp recently raised another $150 million series D round co-led by Founders Fund and Khosla ventures, with a post-money valuation of $7.65 billion.

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Prior to Khosla Ventures, Keith was General Partner at Founders Fund, where he led investments for Ramp, Trade Republic, and Aven. 

In Today’s Episode with Eric Glyman and Keith Rabois We Discuss:

1. Behind Ramp’s Partnership with Founders Fund & Khosla Ventures

• How did the first Founders Fund deal come to be? How was the first meeting?

• What does Keith mean when he says Ramp has the “secret sauce” to be successful?

• What are 1-2 things Keith thinks Eric is world-class at? What are 1-2 things Eric thinks Keith is world-class at?

• How did the latest Khosla deal come to happen?

2. Ramp: The Fastest Executing Company on the Planet.

• How is Eric so good at executing at Ramp? What is his biggest advice to founders on speed of execution?

• What are Eric’s biggest challenges in the next 12 months at Ramp?

• Why does Keith believe momentum is crucial for early stage startups? What are some easy ways founders can build momentum?

• How does Eric think AI will accelerate Ramp and the world of finance?

3. Leadership Lessons From the Best Founders 

• What are Keith’s biggest lessons from Brian Chesky @ Airbnb?

• What did Keith learn from Jack Dorsey @ Square about leadership?

• What does Eric think founders today should build? What should they not build?

• What did Eric learn from Keith on how founders should measure time & progress?

4. Hiring & Team Management

• How did Ramp build a solid talent team? What did they do differently?

• Does Keith & Eric believe it is better to hire externally or promote internally? What is the right balance?

• Does Keith agree founders should hire & get out the way or micromanage?

• How many direct reports does Keith think is enough?

Dom Holland is the Founder & CEO @ Fast, the world's fastest login and checkout with no more passwords, no more typing credit card details or shipping addresses. The special announcement today, Fast have just raised their seed round led by Jan Hammer @ Index, joined by Susa Ventures, Kleiner Perkins, Global Founders Capital and then angels including Nick Molnar, Founder @ Afterpay and proud to say I joined the round as an angel also. Prior to Fast, Domm was a Director @ Tap Tins, a network of smart tap-to-donate collection terminals. Domm was also the Founder & CEO @ Tow, an on-demand towing platform which transacted $50m in its first 4 years.

In Today’s Episode You Will Learn:

1.) How Domm made his way from founding an on-demand towing company in Queensland, Australia to founding one of Silicon Valley's hottest new startups in Fast?

2.) What did Domm do in prior companies that worked and he will do again with Fast? What did not work and he will look to avoid? Does Domm agree with Joe Fernandez @ JoyMode in saying, "serial entrepreneurship is overrated"? What advice does Domm give to first-time founders? Where do they most often make mistakes?

3.) Over the last few years we have seen incredible innovation on the merchant side of payments with Stripe and Adyen but why does Domm believe we have seen no innovation on the consumer side? Why have large internet platforms not built it themselves? Does it have to be an independent 3rd party, external to Google, Facebook, Amazon etc?

4.) With the war for talent, rising rents and a lower standard of living, why did Domm choose SF as the base for Fast? How has the move been? What have been the biggest challenges? What would Domm advise founders contemplating moving to SF? How has Domm been able to hire some big hitter valley operators so early on? How does Domm think about equity sharing and optimising ESOP plans?

5.) Jan Hammer @ Index has discussed Domm's work mentality, so how does Domm structure his day? What does Domm do to ensure he optimises every minute? What work habits has Dom found to be most effective? What has not worked? How does Domm think about balancing speed and quality when executing today?

Items Mentioned In Today’s Show:

Dom's Fave Productivity Tool: Superhuman

As always you can follow Harry, The Twenty Minute VC and Domm on Twitter here!

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and is one of the most popular newsletters on Substack. Lenny is also an extremely active angel investor with a portfolio including Figma, Sorare, Clubhouse, Vanta, WhatNot and many more incredible companies. If that was not enough, Lenny also has the best course on product management, check it out here.

In Today’s Episode with Lenny Rachitsky You Will Learn:

1.) Origins in Product:

• How did Lenny make his way iunto the world of product management at Airbnb?
• What were some of his biggest takeaways from his time at Airbnb on product?
• What mistakes did he make on product at Airbnb? How did it impact his product thinking?

2.) Product Management: 101

• How does Lenny define product management today? How is the role of PM changing?
• When is the right time to hire your first PM as a startup?
• What is the difference between Head of Product and CPO? When do you hire each?
• What are the biggest mistakes founders make when hiring their first product hires?

3.) The Hiring Process:

• How should founders breakdown the process of hiring for their first in product?
• What does the interview process look like? How should founders structure it?
• What core questions should teams ask of prospective candidates?
• What are red flags when interviewing potential product hires?

4.) The Onboarding Process:

• How should founders structure the onboarding process for new product hires?
• What can founders do to make PMs successful in their first 30 days?
• Where do many product hires make the biggest mistakes in the first 30 days?
• What can product hires do to build trust with their new team?

Items Mentioned in Today's Episode with Lenny Rachitsky

Lenny's Fave Book: The Mom Test

Julio Vasconcellos is the Founder and Managing Partner @ Atlantico, one of the leading early-stage funds in Latin America. Prior to the world of venture, Julio got his break in the world of startups as Facebook’s first country lead for Brazil. Julio then went on to co-found Peixe Urbano, a company he scaled to over 1,200 employees and $100M+ in revenue. Post the sale of Peixe Urbano, Julio became an EiR @ Benchmark Capital where he met Scott Belsky. Scott and Julio went on to co-found Prefer, a Benchmark backed company transforming the future of work. If that was not enough, Julio has a stellar angel track record with prior investments in the likes of Ipsy and Quinto Andar.

In Today's Episode with Julio Vasconcellos We Discuss:

1.) Entry into Startups:

• What are 1-2 of Julio's biggest takeaways from being Facebook's first hire in Brazil?
• What does Julio know now that he wishes he had known at the start of his career in startups?

2.) Lessons from Scaling Peixe Urbano to $100M in Revenue:

• How does Julio advise founders on when is the right time to launch a second product or market?
• How does Julio advise founders on the right balance between growth and unit economics?
• When times are tougher, should founders cut fast or cut slower? What is irreversible?
• What are the single biggest and worst things to break in hyper-scaling?

3.) Investing: Why Not Enough Play To Win:

• What is more important, a great market or a great founder?
• Why do not enough VCs today play to win? If they do not play to win, what do they play to do?
• Why is greed the number one enemy of venture returns?
• What are the single biggest investing lessons Julio has learned from Benchmark Founder, Andy Rachleff? How have they impacted his investing mindset?
• Why does Julio believe you can have a close relationship with founders as an angel and not a VC?
• How did Julio's approach to investing change with the transition from angel to VC?
• Does Julio believe that boards really add any value? If so, how?
• What is Julio's biggest investing hit? How did it change his approach?
• What is his biggest miss? How did that impact his mindset?

4.) The Future for LATAM:

• Is Julio as concerned as I am by the removal of growth stage capital from the LATAM ecosytem?
• Does this mean a higher mortality rate for LATAM companies? How does Julio advise founders?
• How did COVID adoption of technology in LATAM fundamentally differ to the US?

Sanjit Biswas is the Founder and CEO @ Samsara, allowing businesses that depend on physical operations to harness Internet of Things (IoT) data. Over the last 8 years, Sanjit has scaled Samsara to $1BN in ARR and a public company with tens of thousands of customers. Before Samsara, Sanjit was the CEO and co-founder of Meraki, one of the most successful networking companies of the past decade. Sanjit grew Meraki from his Ph.D. research into a complete enterprise networking portfolio. Meraki's sales doubled every year from inception and in 2012, Cisco acquired Meraki for $1.2 billion. Huge thanks to Doug Leone for some fantastic question suggestions pre this episode.

In Today's Episode With Sanjit Biswas We Discuss:

1. From Founding to $1BN in ARR in 8 Years:

• What was the founding a-ha moment for Sanjit with Samsara?
• Sanjit sold his prior company Meraki for $1.2BN, what worked with Meraki that Sanjit took with him to Samsara? What did not work that he left behind?
• What does Sanjit know now that he wishes he had known when he started Samsara?

2. The Man Who Found Product Market Fit Time and Time Again:

• What is the one single moment that Sanjit believes you know you have product market fit?
• What are the biggest mistakes founders make when chasing product market fit?
• How does being a bootstrapped company change how a company approaches chasing PMF?

3. Mastering a Multi-Product Company:

• How do you know when it is the right time to launch a second product?
• Does the second product have to make the first product better?
• What are the biggest mistakes companies make when going multi-product?

4. The Art of Great CEOship:

• Does Sanjit believe that the best CEOs are the best capital allocators?
• What has been the single best and single worst capital allocation decision in Samsara's journey?
• What are the biggest mistakes Sanjit has made in leadership? How did he learn and grow from them?

In episode 5 of The Twenty Minute VC, we are joined by Kent Godfrey, General Partner at Pond Ventures. Prior to entering into the VC industry Kent was Chairman and CEO of Andromedia before merging it with MacroMedia. Kent was also CEO of Frictionless Commerce concluding with the sale of the company to SAP in 2006.

Kent has previously served on the board of numerous companies including LiveRail (acquired by Facebook), TRM Corporation (Nasdaq:TRMM), HipBone Communications (acquired by Kana) and Vocal Point Inc (acquired by Telecom Italia).

In this session you will learn: 

• What is the most challenging aspect of being a CEO?
• Should CEO's have a clear and precise strategy for the future?
• What can a CEO do to position themselves to be more successful?
• How can an individual develop the skills to be a successful CEO?
• What Kent learnt from his meetings with Steve Jobs?
• What is the most challenging aspect of transitioning from CEO to VC?
• What do VCs do when concerned about an investment?
• What is the best aspect of being a Venture Capitalist?
• Is it possible to go straight into the Venture Capital industry from University?

We end the episode with a quick fire round where Ken describes the future of the Internet Of Things (IOT). Why Founders are better than a Founder? Plus, what the biggest misunderstanding of the Venture Capital industry is?

For all the resources mentioned in today's show heav on over to www.thetwentyminutevc.com

Erik Allebest is the CEO @ Chess.com, the #1 online chess service on the planet with more than 150+ million members and 15+ million games played each day. Erik has scaled the company to over 700 people and $100M+ in revenue with no venture funding.

In Today's Episode with Erik Allebest:

1. From Unemployable to $100M+ Revenue Founder:

• How did Erik make his way into the world of tech and startups?
• Was his MBA worth it? How does he advise others on whether to get one or not?
• What does Erik know now that he wishes he had known when he started?

2. Scaling to $100M Revenue with No Venture Funding:

• Why did no one want to invest in Chess.com in the early days?
• What did Erik do differently as a result of not raising any venture funding?
• What would Erik have done if he had money from the start?
• What are Erik's biggest pieces of advice to founders with funding today?

3. Hard Lessons Scaling to 150M Members:

• What are 1-2 of Erik's biggest lessons on how to scale users with zero budget?
• What customer acquisition worked? What did not work?
• How important was COVID and The Queen's Gambit to memberships and sign-ups?
• What are the single biggest mistakes Erik sees founders make on customer acquisition today?

4. Parenting, Marriage, Metrics and Money:

• Why does Erik not care about money or capitalism today?
• How has Erik's style of parenting changed over the years? What works? What does not?
• What does Erik believe is the secret to marriage? What have been his biggest lessons?
• Why does Erik hate metrics? If so, how does he run the business towards goals and output?

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Welcome to the 1st episode of The Twenty Minute VC, on today's show we have Guy Kawasaki, Guy is the Founding Partner of Garage Technology Ventures, a seed & early stage venture capital fund investing in extraordinary entrepreneurs with unique technologies. Previously, he was Chief Evangelist of Apple Inc and an advisor to the Motorala Business Unit of Google. Guy is also the author of many best selling books including the recent best seller, The Art of Social Media: Power Tips for Power Users.

In this episode we delve into:

• Why Guy made the transition into the VC industry?
• What is the most important aspect for a startup to have?
• What drives Guy insane about startup founders today?
• What books Guy gives to aspiring entrepreneurs?
• What software & apps Guy cannot live without?

We then finish on a quick fire round where we discover Guy's thoughts on the future of Amazon, Tesla and whether we really are in the midst of a tech bubble.

All of the products mentioned in todays show can be found at www.thetwentyminutevc.com

If you love the show, please do leave a review on the iTunes store and don't forget to subscribe!

Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you might not have heard about.

In Today's Episode with Avi Eyal We Discuss:

1. The Biggest BS "Rules" in Venture Capital:

• Why does Avi believe that it is BS for every deal to need to be a homerun and return the fund?
• Why does Avi believe that signalling is real and it is BS to suggest otherwise?
• Why does Avi believe that it is BS that ownership is crucial to make mega venture returns?
• Why does Avi believe that you do not have to win every deal to be one of the best in venture?
• Why should venture investors not manage the positions of their companies when they go public? Why is it BS to think they have asymmetric information when the company goes public?

2. What Makes the Best Founders:

• Does Avi prefer first or second time entrepreneurs? Why?
• Would Avi rather back a founder that is an expert in a market or one that is new to a market and has the naivety to not know what is hard?
• Are the best CEOs the best fundraisers?
• How does Avi rank the following when investing; team, market, traction and technology?
• When Avi has misread a founder, what was it that he missed?

3. The Biggest Hits and Biggest Misses:

• Monday: How did Entrée build such a large position in Monday over time? How did a Series A lead dropping out leading to a $1.5BN gain for Entree?
• Stripe: Entrée has now 50% of his Stripe position. Why? What is the three step process for Avi in selling positions? How does he know when to and what is the right amount?
• PillPack: Entrée made $15M from PillPack's exit. What did that teach Avi about ownership?
• Cazoo: How was Entrée the only one to make money from Cazoo? How did Entrée's sell strategy help him make millions when everyone else did not sell?

Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame.

In Today’s Episode You Will Learn:

1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel?

2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here?

3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far?

4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Meditations by Marcus Aurelius

As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sumeet Gajri is the Chief Strategy Officer @ Carta, the startup that helps companies and investors manage their cap tables, valuations, investments, and equity plans. Sumeet is largely responsible for all things fundraising and M&A and Carta have raised over $485m from a16z, USV, Thrive, Spark, K9, Lightspeed and Meritech to name a few. Sumeet is also Managing Partner @ Original Capital, where he has partnered with companies including Front, Tonal, Instabase, Everlywell and Cockroach Labs to name a few. Finally, Sumeet is also an LP in world-leading firms such as USV and Valar Ventures.

In Today’s Episode You Will Learn:

1.) How Sumeet made his first foray into the world of venture in NYC having grown up in Scotland? How that led to his move to operations with Carta? How his learnings from Carta led to his establishing Original Capital?

2.) How is Original Capital different from every other micro-fund? How does Sumeet approach portfolio construction with the fund? What is the optimal number in a portfolio? How does Sumeet think about loss ratio? What 3 criteria dos every new investment have to pass to make it into the portfolio? How does check size vary by deal?

3.) How does Sumeet invest in some of the best companies in between "official rounds"? What does this conversation look like with the founders? How does Sumeet analyse reserve allocations? What makes the right strategy? What are his capital concentration limits per company? How does Sumeet think about using SPVs effectively?

4.) Sumeet helps his companies fundraise a lot, what does the first step look like? How does he advise on investor selection? How does he advise on pipeline management? Should founders speak to investors when they are not raising? How open should they be in these meetings? What can founders do to catalyse the process? Where does Sumeet see many founders make mistakes?

5.) How does Sumeet think about distribution vs product? What can founders do to adopt a more distribution first mindset? What have been some of Sumeet's biggest lessons in turning Carta from a single product company to a multi-product company? Do companies have to own their own lines of distribution today?

Items Mentioned In Today’s Show:

Sumeet’s Fave Book: Howard Marks: The Value of Predictions

As always you can follow Harry, The Twenty Minute VC and Sumeet on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kanyi Maqubela is a Partner at Collaborative Fund, who have made investments in AngelList, CodeAcademy, AltSchool, Reddit, Task Rabbit just to name a few. On a more personal note, and a little background on Kanyi, he is originally from Johannesburg South Africa, and was a founding employee at Doostang, a venture-backed peer-to-peer career marketplace, he attended Stanford University and as Kanyi states his most meaningful and difficult work done so far is his work on the Obama Campaign in 2008. You can checkout Kanyi's blog here! I would like to thank Mattermark for providing all the data and analysis for this interview and you can check them out here!

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In Today's Episode You Will Learn:

1.) How Kanyi made the move into VC and tech from South Africa?

2.) Was the decision to leave Stanford tough? Why would Kanyi advise others to say in school? What was so tough about the startup experience for Kanyi?

3.) What is the investing thesis at Collaborative Fund? What stage do you prefer? Average cheque size? Sector preference? Does specializing in themes result in higher returns?

4.) How is it being such a young partner in the industry? What are the challenges Kanyi has face? Does Kanyi think his age acts as a disadvantage when it comes to attracting older founders?

5.) What are Kanyi's personal marketing strategies that he uses to establish his own personal brand? What platforms are most effective?

6.) How effective does Kanyi find demo days and hackathons as source of deal flow? Are there any tips Kanyi would suggest to maximise their utility? What is Collaborative's most effective form of deal sourcing today?

Items Mentioned In Today's Episode:

Kanyi's Fave Book: The Brothers Karamazov

Kanyi's Most Recent Investment: CircleUp

As always you can follow Harry, The Twenty Minute VC and Kanyi on Twitter here!

If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

Leah Busque is a General Partner @ Fuel Capital, one of Silicon Valley's leading seed funds with the most incredible portfolio including many previous 20VC guests Ryan @ Flexport, Florian @ Mesosphere, Alex @ Clearbit and Dan @ Convoy (episode Friday). As for Leah, prior to VC, she was a pioneer of the sharing economy with her founding of TaskRabbit, one of the leading online labor marketplaces in the US, raising over $37m in the process before their sale to IKEA last year. Due to this incredible success, Leah has been named to Fast Company's "100 Most Creative People in Business".

In Today’s Episode You Will Learn:

1.) How Leah made her way from sitting on the couch discussing dog food with her husband to founding TaskRabbit and how that translated into the world of VC today?

2.) How did Leah's time in operations affect:

• Question from Sean @ Shasta: the founders Leah backs and why she chooses them?
• Question from Craig @ Collaborative: the business models and unit economics Leah backs and why she backs them?

3.) Leah has said before that "authenticity and transparency between VC and founder are now table stakes", what more can be done to improve the VC product? How did Leah select the investors she worked with on TaskRabbit? How can founders truly determine "founder friendly" VCs?

4.) What have been Leah's biggest surprises on her move into the world of VC? What elements has Leah found most challenging? How has Leah looked to scale that learning curve?

5.) What does a successful marketplace look like? How does one know when is the right time to really scale a marketplace? What is the inflection point? How can marketplaces be efficient with their unit economics from day 1? How does one balance the NPS of the supply side with the NPS of the demand side?

Items Mentioned In Today’s Show:

Leah’s Fave Book: Founders at Work 

Leah’s Most Recent Investment: Bark: Parental Control Phone Tracker App

As always you can follow Harry, The Twenty Minute VC and Leah on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Parker Conrad is the Founder and CEO @ Rippling, the employee management platform allowing you to manage your employees' payroll, benefits, devices and more—in one place. To date, Parker has raised over $197M for Rippling from the likes of Founders Fund, Kleiner Perkins, Initialized, Bedrock, Greenoaks and Coatue. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in the likes of Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund.

In Today’s Episode with Parker Conrad You Will Learn:

1.) How did Parker make his way into the world of technology and startups? What was the founding a-ha moment for Parker with Rippling? How did his journey with Zenefits change or alter his leadership style today with Rippling?

2.) Why does Parker believe that the conventional advice of focus, focus, focus is BS? What does Parker mean when he states, "The Compound Startup"? How does the approach of the compound startup differ from traditional approaches of product and company building? What are the core benefits of using the compound startup approach?

3.) How does Parker think about providing sufficient product quality with an increasing breadth of product offering, entailed within a compound startup? In what way does pricing differ when comparing compound startups to traditional startups? How can compound startups optimise their pricing on a bundle basis? What has Slack and Microsoft taught us about this?

4.) Why does Parker disagree with the conventional analogy of the VC <> founder relationship being a marriage? Why does Parker refer to it more as a "General Contractor" relationship for a house? What can founders do to sufficiently protect themselves from overarching VCs? What can VCs do to be the very best partners to the founders they work with?

5.) How does Parker evaluate his relationship to money today? How has it changed over time? What does Parker know now that he wishes he had known at the start of his founding of Rippling? What have been Parker's biggest lessons on talent acquisition? Why did Parker decide to bring on a COO when he did? How has it changed his role?

Item’s Mentioned In Today’s Episode with Parker Conrad

Parker’s Favourite Book: Matilda by Roald Dahl

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Steve Huffman is the Co-Founder & CEO @ Reddit, home to thousands of communities, endless conversation, and authentic human connection. To date, Reddit has raised over $550m in funding from some of the world's leading investors including Sequoia Capital, Marc Andreesen, Peter Thiel, Ron Conway, Sam Altman, Josh Kushner, Alfred Lin and Tencent, just to name a few. Steve started his career at Y Combinator as one of their first alumni back in 2005. At YC, Steve co-founded Reddit with Alexis Ohanian, which they sold in 2006 to Conde Naste Publications. In 2010, Steve co-founded Hipmunk, making business travel seamless and easy. Then in 2015, Steve re-joined Reddit as their CEO.

In Today’s Episode You Will Learn:

1.) How Steve made his way into the world of startups and came to be one of the very first ever entrants in the now hailed Y Combinator? How did that lead to the founding of Reddit? Why did Steve return to Reddit, the company he founded, in 2015?

2.) What were Steve's biggest lessons from his journey with Hipmunk when it came to product feedback and iteration? How does Steve assess people's reliance on data today to drive product decisions? Why does he believe 3 criteria must be considered? What are the other two? What time did Steve see the confidence of his own intuition really increase?

3.) How does Steve think about stress management today? What was he like when he was younger in his relationship to stress? What did he actively do to change his relationship to stress? How has Steve seen himself change and develop as a CEO? What have been the inflection points? What has he struggled and also made mistakes in the journey?

4.) What have been Steve's biggest lessons when it comes to hiring truly A* talent at scale? What are the commonalities in the very best hires Steve has made? In the cases of it not working, what does Steve advise founders on the right way to let someone go? How does one do it with efficiency and compassion?

5.) Why does Steve believe that in dense cities, self-driving cars will not be that useful? How does Steve envisage the future of consumer transportation? What does he believe are the alternatives to self-driving cars? How does Steve see the future for the unbundling of social networks? Will they be unbundled into specific communities? How will this look?

Items Mentioned In Today’s Show:

Steve’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ravi Viswanathan is the Founder and Managing Partner @ NewView Capital, launched in 2018 with their $1.35Bn Fund I, they have already set themselves as leaders in the world of growth funding with 3 massive exits in less than 2 years in the form of Plaid, sold to Visa for $5.3Bn, Acquia, sold to Vista Equity for $1Bn and then Scout, sold to WorkDay for $540M. Prior to founding NewView Ravis spent 14 years at one of the largest venture firms in the business, NEA where he co-led their venture growth equity practice and in 2016, became COO @ Nea. Before the world of venture, Ravi spent 4 years as a VP @ Goldman Sachs and before that was at McKinsey & Co.

In Today’s Episode You Will Learn:

1.) How Ravi made his way into the world of venture from investment banking and how that led to his founding the monster $1.35Bn Fund I for NewView Capital?

2.) Given the first fund being $1.35Bn, how did Ravi find the fundraising process for NewView? On reflection, what did he and the team do well that they would do again? What did they not do well that they would alter? What advice would Ravi give to first-time fund managers raising today?

3.) Would Ravi agree with Bill Gurley, "the biggest challenge today is the sheer quantum of capital flowing into the industry"? What does Ravi make of the rise of private equity (PE) houses entering the venture landscape? How does it change the exit landscape?

4.) How does Ravi think about the right way for funds to navigate and approach the secondary market? What advice would he give to emerging managers? How does Ravi feel about founder secondaries? What framework does he use to determine whether the amount is reasonable?

5.) How does Ravi think about what it take to truly win the best deals in competition today? If one does not have the budget of a16z, how does one build a venture platform? Where do the majority of investors make mistakes when it comes to VC value add?

Items Mentioned In Today’s Show:

Ravi's Fave Book: Shoe Dog: A Memoir by the Creator of NIKE, Born A Crime: Stories from a South African Childhood

Ravi’s Most Recent Investment: Plaid

As always you can follow Harry, Ravi and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Businesses are always looking for ways to shorten their sales cycles. HelloSign provides secure, effortless eSignatures proven to speed up contract signing by 80%. Most clients go from a multi-week turnaround to a multi-hour one. They’re an industry leader and have been voted #1 for Ease of Use two years in a row on G2 Crowd. Don’t let pen and paper processes slow you down. Click Here to join the millions of users already using HelloSign to close more deals faster!

Jon Callaghan is a founder of True Ventures, one of the West Coast's leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of Wordpress) and more amazing companies. Jon also led the deals and sits on the board of Fitbit, Brightroll, Peloton and Glu Mobile, just to name a few. Prior to True, Jon founded 3 of his own companies, the first being in 1986 with Mountain Bike Outfitters Inc. Following several years founding companies, Jon made his move into VC with Summit Partners and then enjoyed roles with AOL's venture incubator, CMGi's Venture group and Globespan Capital.

Keith Rabois is an investment partner at Khosla Ventures where he has led investments in Stripe, Thoughtspot, HealthTap and Teespring among many others. He also started OpenDoor, which aims to transform the process of selling a home through technology. Keith's unparalleled operational track record does not stop there as he has forged several of the most important new social and commerce platforms over the last decade holding key roles at LinkedIn, Paypal and being COO at Square. As a board member, Keith guided Yelp [NYSE: YELP] and Xoom [NASDAQ: XOOM] from inception to successful IPOs. Simultaneously, he also invested in other like-minded entrepreneurs with early stakes in YouTube [acquired by GOOG], Yammer [acquired by MSFT], Palantir, Lyft, AirBnB, Eventbrite and Quora.

In Today’s Episode You Will Learn:

1.) How Keith made the move from key executive at LinkedIn, Paypal and Square to being a VC with Khosla?

2.) Question from Lee Hower: What were the biggest learnings from playing a key role at LinkedIn, Paypal and Square? How do they compare to learning from Slide, a not so successful project? Does one learn more from success or failure?

3.) Question from Jason Lemkin: How can founders assess the potential of their teams? How long is it possible to allow individuals to stretch to their roles? What are the signs that people are either exceeding or falling below expectations?

4.) Eric Yuan @ Zoom has previously illustrated the importance to me of sustainable growth. What is Keith's view of this? Why does he not like this term? What are his thoughts on the key constraints on growth for most startups?

Items Mentioned In Today’s Show:

Keith’s Fave Book: The Upside of Stress

Keith's Fave Blog: Stratechery 

Keith’s Most Recent Investment: Forward 

As always you can follow Harry, The Twenty Minute VC and Keith on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Pejman Nozad is the Founding Managing Partner @ Pear.vc, one of the leading seed stage funds in the valley. However, Pejman did not enter the tech industry like most venture capitalists. Having immigrated from Iran, he lived in an attic above a yogurt shop and took a job at a rug store in the Valley. But he immersed himself in what was happening in technology. Slowly, with a few small investments, he developed a reputation for identifying talent and helping take promising ideas to the next level. From next to nothing, he built a $20B portfolio, investing in over 100 startups and seeding several multi-billion dollar companies such as Dropbox, Lending Club, SoundHound and Gusto.

In Today’s Episode You Will Learn:

1.) How Pejman made his way from football in Iran to rug dealer in Palo Alto to leading seed stage VC?

2.) Mike Moritz has previously said that 'a call from Pejman is a call he will always take'. What led Mike to say this? What makes Pejman the brilliant networker and community builder that he is?

3.) How does Pejman assess early stage founders and teams? From seeing an early Andy Rubin, what did Pejman take from that as to what makes the best founders?

4.) Pejman invested $400K in Andy Rubin's Danger which exited 8 years later for $500m yet Pejman only 2x his money. What did he take from this? What have been the other major learning inflection points for Pejman in the journey?

5.) From working alongside some of the best investors of our generation, what does Pejman perceive to be the commonalities of the best investors? How do they operate? How do they evaluate early stage opportunities?

Items Mentioned In Today’s Show:

Pejman’s Fave Book: Power of Now

Pejman's Most Recent Investment: Gfycat

As always you can follow Harry, The Twenty Minute VC and Pejman on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Today we deconstruct the canonical question in early-stage sales. Does the founder need to create the sales playbook? Then secondly, if not, should the first sales hires be reps or a sales leader? Today we are joined by 7 of the best sales leaders to share their thoughts.

Jordan Van Horn is a Revenue Leader @ Montecarlo. Previously Jordan spent 4 years with Segment and before that spent another 4 years at Dropbox.

Oliver Jay (OJ) most recently spent 6 years at Asana where he was hired as the company’s first revenue leader. Before Asana, OJ spent 4 years at Dropbox where he scaled the sales team from 0 to 50 while tripling ARR.

Dannie Herzberg is a Partner @ Sequoia Capital and previously spent 4 years at Slack as their Head of Enterprise Sales. Before Slack, Dannie spent 5 years at Hubspot building sales, opening an SF office, and then joining product to launch CRM & platform.

Zhenya Loginov is the CRO @ Miro, where he runs the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas.

Kyle Parrish is VP Sales @ Figma, where he has scaled the sales team from 0 to over 100 people in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, where he scaled the Austin, Texas office from 3 to over 80 people.

Sam Taylor is the VP of Sales and Customer Success @ Loom, at Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader.

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.

Mitch Tarica is Head of North America Sales at Zoom Video Communications. Before Zoom, Mitch spent over 5 years at RingCentral and before RingCentral, Mitch was at Oracle for over 7 years in numerous different sales roles.

In Today's Discussion on Sales Playbooks We Learn:

1.) What is the right definition for a "sales playbook"?

2.) When is the right time to change your "sales playbook"?

3.) What are the biggest mistakes or misnomers made around the "sales playbook"?

4.) Should the founder be the one to create the first sales playbook or can it be a sales leader?

5.) When is the right time for founders to hire their first sales leaders?

6.) For the first sales hire, should founders hire sales reps or a sales leader?

7.) When should you hire a rep vs a sales leader? What are the nuances?

Luca Ferrari is Co-Founder and CEO of Bending Spoons, one of the most incredible but untold success stories in startups. Luca has scaled Bending Spoons to 100M monthly active users, $380M in sales in 2023 and aiming to reach $500M in EBITDA by the end of 2026. The company’s products include Evernote, Meetup, Remini, and Splice and their products have now been downloaded more than 500M times.

In Today’s Episode with Luca Ferrari We Discuss:

1. From McKinsey Associate to $2BN Founder

• What was Luca like as a child? How would his parents have described him?
• Why did Luca share his McKinsey salary with his co-founders?
• What were Luca’s biggest lessons from his failed startup?

2. Bootstrapping Bending Spoons 

• Why did Luca decide to bootstrap Bending Spoons?
• What does Luca think about the EU vs. US startup environment?
• Why did Luca kill a $7M project? What were his lessons?
• How did Luca pick his investors?

3. How to Find the Best Talent

• What are the 3 key traits Luca looks for when picking the best talent?
• Why does Luca think traditional interview strategies do not work?
• What tests does Luca conduct for each candidate?
• What were Luca’s biggest hiring mistakes?

4. Mastering Acquisition & Growth

• How does Luca determine which products to acquire? How does he identify signals?
• How does Luca approach pricing assets? How does he win every bid?
• What are Luca’s biggest lessons from acquiring Evernote?
• What key lessons on risk management does Luca wish he’d known 10 years ago?
• What are Luca’s biggest challenges on user acquisition?

Jared Friedman is a Partner @ Y Combinator, the world's most successful accelerator with portfolio companies including the likes of AirBnB, Dropbox, Stripe, Zenefits, Twitch, the list goes on. Prior to YC, Jared was Co-Founder & CTO @ Scribd, the digital library and document sharing platform, which has over 80 million users and attained funding from the likes of Marc Andreessen, Redpoint and CRV. As well as his time in operations, Jared is also a prolific angel investor with investments in the likes of Instacart, FundersClub and Cruise Automation just to name a few.

In Today’s Episode You Will Learn:

1.) How Jared made his way from founding the immensely successful, Sribd, to being a YC partner?

2.) What is the process behind the invites for YC demo day? What does it take for one to get a hotly anticipated seat? Is there really a black list?

3.) A lot of investors suggest that if you are seeing the company at demo day it is too late, what is the thesis around letting friends and family in to view and invest in the companies before demo day?

4.) How can investors look to get into the best YC companies? What can the investors do to show their value to both the companies and the YC partnership? How do you look to advise companies with regards to selecting investors?

5.) Demo days have scaled massively so I have to ask, is there enough capital to go into the 120+ companies now being produced at YC demo days? What are the strategies for scaling YC effectively?

Items Mentioned In Today’s Show:

Jared's Fave Book: Sapiens: A Brief History of Humankind

Jared’s Fave Blog: HackerNews

Jared Most Recent Angel Investment: Starcity

As always you can follow Harry, The Twenty Minute VC and Jared on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Foundersuite makes the leading CRM for raising startup capital. Since March of 2016, Foundersuite customers have raised over $130M in seed and venture capital. Foundersuite's CRM sits on a database of over 50,000 investors, which will help you quickly populate your fundraising funnel including a beautiful and easy-to-use investor update tool, and the recently launched a new portal that helps investors and accelerators track their portfolio companies on a single dashboard. For a whopping 40% off a Monthly or Annual subscription use the code "20MinuteVC" at checkout. 

Greenhouse Software designs tools that help companies hire great people and ultimately build better businesses. Greenhouse works with over 1,500 of the world’s most innovative companies such as Airbnb, Slack, Snap Inc. and Lyft. A wrong hire is not only costly for a company but can also turn an employee into an unhappy one. With Greenhouse's Applicant Tracking System, companies can make well-informed decisions and hire qualified candidates who are empowered to do the best work of their careers. Anybody who has a company that's scaling quickly but has trouble hiring and retaining the right people. Visit www.greenhouse.io today to discover how your company can grow.

Max Levchin is one of the great founders and technologists of our time. As the Founder and CEO of Affirm, he has built am $18.7BN monster in the buy no pay later space. Prior to Affirm he was one of the original co-founders of PayPal. Max is also the co-founder and Chairman of Glow, a data-driven fertility company. Max is also an immensely successful angel investor with a portfolio including the likes of Yelp, Pinterest and Evernote. 

In Today’s Episode We Discuss:

04:19 How to Hire the Best People in the World

05:05 How to Manage Extreme Personalities

08:18 Biggest Lessons on Trust and What Happens When Lost

12:05 Is Grading Talent A and B Players Total BS?

15:31 How to Think About Calculated vs Uncalculated Risk

27:18 How to Create a Culture of Post Mortems: Step by Step

32:08 Why Every Person Must Write and How to Create a Writing Culture

36:01 Leadership Lessons from Layoffs

38:38 Is Affirm Losing or Beating Klarna in the US?

47:03 Peter Thiel or Elon Musk: Who Would Max Rather Start a New Company With?

48:37 Quickfire Round

Puneet Mehta, Founder @ Msg.ai, an artificial intelligence startup for conversational commerce and for an AI founder you don’t get much better than starting your career at IBM's TJ Watson Center, which is exactly what Puneet did. He then went on to build predictive platforms to power large-scale trading systems aka bots on Wall St. It is clearly not joust us who think he is awesome as Advertising Age named Puneet to the Creativity 50 list in 2014, honoring the most creative and innovative thinkers and doers.

• Paul Graham: Blog

Alain De Botton is one of the greatest philosophers of our time. His work has had a profound impact on me more than any other. I have wanted to do this episode for the last 8 years. 

In Today’s Episode with Alain De Botton We Discuss:

1. Why Status is Making You Miserable: 

• Why are we richer yet more anxious than ever?

• What is the right way to define status? Why do we want it so much?

• Is it bad to want status? What are some non-obvious signs that you are seeking status when you do not realise it?

• Does social media enhance the desire for status? How so?

• Do the happiest people want status the least? What are Alain’s biggest observations in how truly happy people think about status?

2. Why Parents Want You To Fail: 

• Why is the sign of good parenting when your child does not want to be famous?

• Why do your parents sometimes want you to fail? 

• What should parents do if their child wants to chase an unachievable goal?

• Why should parents encourage their children to start very early? 

3. Why Meritocracy is a Fallacy & Meaningful Work:

• Why does Alain believe a true meritocracy is an impossible dream?

• Why is meritocracy a bad thing when taken to the extreme?

• Why does Alain believe that companies are not families?

• Why does Alain tell people that they should not bring their full selves to work? 

4. WTF is “Meaningful Work”: 

• What does it mean to do “meaningful work”?

• Why do humans need to do “meaningful work” today in a way that we did not many years ago?

• What are Alain’s biggest pieces of advice to young people today, unsure of what they should do with their lives and careers?

• Why does Alain believe the idea of a “calling” is BS?

5. Ambition, Achievement and Sacrifice:

• What does Alain mean when he says “you have to tolerate your own averageness”?

• What does Alain say to the young generation who want work/life balance?

• What does Alain mean when he said you “cannot be at war with yourself”?

• Does Alain agree that to achieve you must sacrifice?

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world. Today, Orlando directs the firm’s strategy and investment decisions. Orlando has overseen over 420 software acquisitions conducted by the firm, representing more than $235 billion in transaction value. Forbes named him "Wall Street’s best dealmaker" in 2019, and he was dubbed "Private equity’s king of SaaS" by the Financial Times in 2021.

In Today's Episode with Orlando Bravo We Discuss:

1.) From Puerto Rico Roots to Wall Street's Best Dealmaker:

• How did Orlando come to co-found Thoma Bravo? What was that a-ha moment for him?
• Orlando mentioned 2 mentors that shaped how he thinks, who were they? What are his single biggest lessons from those mentors?
• What does Orlando know now that he wishes he had known when he started his career?
• Why does Orlando disagree with setting timelines in life? Why does it not help?

2.) The Secret to Success in Value Investing:

• What is good value investing today? What is it not?
• What three things does Orlando look for when doing a deal and acquiring a company?
• Why is every company in the world worth its future cash flows?
• How important is price today? How does Orlando reflect on his own price sensitivity?
• Many suggest Coupa and Anaplan were extremely expensive. How does Orlando respond and defend the prices he paid for companies in 2020-2022?

3.) WTF is Happening In Markets Today:

• How does Orlando reflect on where the market is today?
• Is this the new normal? How does Orlando expect the market to change over the next 12 months?
• Why does Orlando believe that the best companies win in the worst times?
• Is this the result of quantitative easing on behalf of central banks? Who is to blame?
• How does Orlando balance the mindset of his team between risk on and taking advantage of lower prices in market but also not catching a falling knife?

4.) Orlando Bravo: The Leader, Father and Husband:

• What is Orlando's biggest fear in investing? How has this changed over time?
• How does Orlando reflect on his own relationship to money today? How has that changed?
• What are Orlando's biggest parenting lessons from his mother?
• Why does Orlando believe that for most people, their late twenties are their toughest?
• How does Orlando instill the same drive and ambition in his children that he had, despite very different financial profiles growing up?
• How does Orlando maintain being at the top of his game in his profession but also being a great husband? What is the secret to a happy marriage?

Items Mentioned in Today's Episode:

Orlando's Fave Book: The Power of Now: A Guide to Spiritual Enlightenment

Ophelia Brown is the Founder of Blossom Capital, one of Europe's newest but leading early-stage venture firms. Ophelia and the Blossom team have invested in stand-outs including Checkout, Duffel, Tines, and Moonpay. Prior to Blossom, Ophelia was a GP at LocalGlobe and a Principal at Index Ventures where her investments included Robinhood and Typeform.

In Today's Episode with Ophelia Brown We Discuss:

1.) From Restaurant-Owning DJ to Leading European VC:

• How Ophelia made her way into the world of venture and came to found Blossom?
• What does Ophelia know now that she wishes she had known when she entered venture?
• What does Ophelia feel she is running away from?

2.) Venture Capital: The Market:

• Why does Ophelia believe the best venture firms focus either by stage/theme/geography?
• Why does Ophelia believe that marketing in venture has no substance? How can founders determine between what is real and what is false?
• Why does Ophelia believe that growth investors have ruined the venture market?
• When does Ophelia believe VCs will realise that FOMO investing is not a good strategy?

3.) Ophelia Brown: The Investor and Fund Manager:

• What has been Ophelia's biggest investing mistake? How did it change her mindset and approach?
• In a world where everyone does seed investing, why does Ophelia not?
• How was raising the first Blossom fund? What were some of her biggest lessons?
• Why does Ophelia believe that follow-on investing can damage returns?
• How does Ophelia reflect on her own relationship to price? When has she paid up and it worked? When has she paid up and it not worked?
• Does Ophelia think it is fair that many find her curt and abrasive to work with?

4.) Europe: Is Now Really The Right Time?

• What would Ophelia like to see change in the way European VCs act?
• If Ophelia could invest in one seed firm, one Series A firm and one growth firm in Europe, what would they be? Why?
• What are 1-2 of the biggest barriers Europe must overcome in the next 5 years?

Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman.

In Today's Episode on Seed Rounds We Discuss:

1. The Three Types of Seed Round:

• What are the three different types of seed round today?
• Has seed ever been this competitive?
• Will seed be unimpacted by the macro decline we are seeing?
• Why are growth and multi-stage funds being more active than ever in seed?

2. Too Much Cash Will Kill You!

• Why does Ed believe that too much capital can kill companies at the seed round?
• Why does Ed believe that the best founders are not always optimising for the highest price?
• What are the single biggest negatives of taking a high price at the seed round?
• What advice does Ed have for founders who have large offers from multi-stage funds at seed?

3. Is Growth Dead?

• Why does Ed disagree and suggest that growth is not dead?
• What do multi-stage and growth funds now what to see that they did not before?
• How will the growth market evolve over the next 12-18 months?

4. IPOs, AI and M&A:

• What will cause the IPO windows to crack open again?
• Why does Ed believe that many investing in AI are simply giving money to Nvidia?
• Does Ed agree that 95% of the cash going into AI from venture today will go to zero?
• Will we see more or less M&A in the next 12 months?
• How did Ed evaluate the Loom acquisition by Atlassian?

Joey Levin is the CEO of IAC where he has overseen the constant evolution of the company, including the initial IPO and subsequent spin-off of Match Group, the spin-off of Vimeo, and the acquisitions of Angie’s List and Care.com. If that was not enough, in October 2022, Joey was also appointed as CEO of Angi Inc. In addition to this, Joey also serves on the boards of IAC, Turo, and MGM Resorts International.

In Today's Discussion with Joey Levin We Discuss:

1.) The Makings of a Great Leader:

• When Joey was younger, what did he want to be when he grew up?
• What is Joey's biggest advice to people coming out of college/university at this time?
• What 1-2 things does Joey credit his internal and fast rise in IAC to?

2) Value Investing is BS & The Markets Today:

• Why does Joey believe the idea of "value investing" is BS?
• What 1-2 behavior traits of investors in the last few years were most dangerous?
• Why does Joey believe that the current market is reasonable and now is the new normal?
• How does Joey keep internal morale high when people have become accustomed to high stock prices?
• Does Joey believe in the statement, "be greedy when others are fearful and fearful when others are greedy"?

3.) Simplification is the Secret to Margin & Messaging 101:

• Why does Joey believe simplification is the core of high margins?
• How can startups and scale-ups identify where to simplify first? What are the subsequent steps?
• Why does Joey believe that the best values should make you feel uncomfortable?
• What is a lesson from Joey's father on what makes truly great messaging?

4.) Parenting, Money and Marriage:

• How does Joey reflect on his own relationship to money today?
• What are 1-2 lessons taught by his mother on how to approach money and wealth?
• What does Joey believe is the secret to truly happy marriages?
• What are Joey's biggest lessons on what it takes to be an effective and good father?

Roseanne Wincek is an investor with IVP, one of the leaders in growth financing with a portfolio including the likes of Snap, AppDynamics, SuperCell and Slack. At IVP, Roseanne focuses on investing in later-stage, high-growth consumer and enterprise companies, currently serving as a Board Observer for MasterClass and actively working with IVP’s investments in Compass, Glossier, and Qubole. Prior to IVP, Roseanne was a Principal with Canaan Partners where she completed transactions for Beckon, Metacloud, and Stayful, just to name a few. Prior to VC, Roseanne was a co-founder @ imthemusic working to built music apps on the early Facebook platform.

Dhananja Jayalath is the Co-Founder & CEO @ Athos, creating the new standard for fitness by changing the way we train the human body. Athos have funding from our friends at Social Capital, Felix Capital and DCM Ventures just to name a few of their investors. Prior to Athos, DJ turned down a job with Apple straight from University to pursue his vision of creating the next generation of consumer fitness wearables with Athos.

In Today’s Episode with DJ You Will Learn:

• How DJ went from University to turning down Apple to founding Athos?
• How did DJ come to meet Chamath @ Social? How was the fundraising experience? What did Athos do well and what would DJ like to improve for the next round?
• How does DJ approach iteration and testing within product testing at Athos?
• What are the lessons DJ has learned in the manufacturing and iteration process with Athos?
• How does DJ approach business models for Athos today? Does DJ agree that the winners of hardware will be determined by software?

Items Mentioned In Today’s Show:

DJ’s Fave Book: Velocity: The 7 New Laws For A World Gone Digital

As always you can follow Harry, The Twenty Minute VC and DJ on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world’s first Wi-Fi video doorbell while working in his garage in 2011. Since Ring’s launch in 2013, Ring has helped make thousands of neighborhoods safer all around the world. As part of the journey, Jamie raised over $385M from the likes of True Ventures, Felicis, First Round, CRV, Upfront and more. In 2018, Amazon acquired Ring for a reported $1BN. Prior to Ring, Jamie founded several successful ventures including PhoneTag, the world’s first voicemail-to-text company, and Unsubscribe.com, a service that helped email users clean commercial email from their inboxes. He successfully sold both companies in 2009 and 2011 respectively.

In Today's Episode with Jamie Siminoff We Discuss:

1.) From Creating the First Wi-Fi Doorbell to $BN Acquisition:

• When was the moment Jamie realized he had to create the world's first Wi-Fi-enabled doorbell?
• How di Richard Branson come to be an investor in Ring? What was the process?
• How does Jamie advise other founders when it comes to the question of whether it is valuable having business moguls as investors in their business?

2.) Crucible Moments: From Lawsuits and Near-Death to $22M in Sales in a Day:

• When Jamie hears the words "near-death experience" what is the moment in the Ring journey that comes to mind?
• How did Jamie get through a crippling lawsuit and come out selling $22M in 24 hours on QVC?
• How did Jamie feel when he placed a $500M order with manufacturers when he only had $100M?
• What does Jamie believe was the hardest phase of the business?

3.) Jamie Siminoff: The Leader:

• Why does Jamie want to hire marathon runners? Why does the analogy make for good hires?
• Does Jamie start from a position of trust with new hires and it is there to be built or start with no trust and it is there to be gained?
• Does Jamie believe he is a tolerant leader? What does he mean when he says, "I want to see the dirt under your fingernails"?
• Why does Jamie believe that building a brand is like making great wine?
• Why does Jamie really hate customer surveys? What should be done instead?

4.) Selling for $1BN to Amazon:

• How did the Amazon acquisition come to be? How did the discussion go?
• Why did Jamie decide then was the right time?
• When you sell for a $1BN, does the cash hit your account soon? When did Jamie actually receive the money? How did he feel when he saw it is in his account?
• What does Jamie believe Ring did so well to make the acquisition a success?
• What did Amazon do well to ensure Ring was integrated most effectively?
• What are 1-2 of the biggest lessons Jamie has learned from being within Amazon?

Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California.

In Today's Episode with Jordan Van Horn We Discuss:

1.) Entry into the World of Sales:

• How did Jordan make his way into the world of sales first with a vineyard?
• What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset?
• What does Jordan know now that he wishes he had known when he entered sales?

2.) The Sales Playbook:

• How does Jordan define "the sales playbook"? What is it not?
• What five core things should the sales playbook help you accomplish?
• Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales?
• How does Jordan advise founders on three signals that now is the right time to bring in a sales hire?
• How does Jordan advise founders on whether the first sales hire should be a rep or a leader?

3.) The Secrets to Pricing and Discounting:

• Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for?
• When does price discipline become important in a company journey? What are the dangers of not having price discipline?
• What two tools do sales leaders have to use in order to create urgency in a deal closing process?
• How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it?

4.) The Hiring Process:

• How does Jordan structure the hiring process for all new sales hires?
• What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers?
• Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for?
• Does Jordan use case studies with candidates? What makes the best? What makes the worst?

5.) The Onboarding:

• What is the ideal onboarding process for new sales reps?
• What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready?
• What are some early signs that a new hire is not working out? How do we measure their impact?
• For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long?

James Beshara is the Co-Founder @ Tilt the micro-crowdfunding platform that allows you to receive funding from friends—changing the way collaborative funding works. Tilt has raised $37 million from 3 rounds of funding from the likes of Andreesen, SV Angel, Alexis Ohanian, Naval Ravikant and Sean Parker just to name a few. As for James Before co-founding Tilt, he studied Development Economics as an undergrad and then went on to build dvelo.org, a site for crowdfunding loans and donations to poverty-alleviation organizations in developing countries. In order to vote for who you think will win James and Harry's beer pong match, head over to @twentyminutevc on Twitter and vote using our poll.

Luis Von Ahn is the Founder & CEO @ Duolingo, the leading language learning platform with over 100m users. They have backing from some of the best in the investing world with over $100m in funding from the likes of USV, Kleiner Perkins, NEA, Google Capital and even Ashton Kutcher. Prior to Duolingo, Luis is known for inventing CAPTCHAs, being a MacArthur Fellow (“genius grant” recipient), and selling two companies to Google in his 20’s. Luis has been named one of the 10 Most Brilliant Scientists by Popular Science Magazine, one of the 20 Best Brains Under 40 by Discover.

In Today’s Episode You Will Learn:

1.) How Luis, a man as he describes "never great at learning languages", came to found the leading language learning app, Duolingo?

2.) Why do VCs generally believe Edtech to be such a "hard" space? Is that really a fair assumption? How does the role of government change the distribution and landscape of edtech? How does content creation play a pivotal role in edtech today?

3.) What role does Luis believe AI and ML will play for the future of edtech? Will the transition to bots represent a transformational shift in the interface paradigm? How does gamification and edtech integrate? Why does Luis always measure themselves against the most addictive of games?

4.) How has Luis seen himself scale and change as a leader with the scaling of the firm? What story shows an element that Luis struggled with and how did he overcome it? What were the major inflection points in the growth of the firm?

5.) Duolingo recently raised their $25m Series E, how did this round differ from prior rounds? Why did they want to negotiate down the figure they wanted to raise? How did Valley based VCs present herd mentality for the duration of the recent raise?

Items Mentioned In Today’s Show:

Luis’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid 

Luis' Fave Blog: AVC by Fred Wilson

As always you can follow Harry, The Twenty Minute VC and Luis on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Semil Shah is the founder of Haystack, an early stage investment firm now investing out of it’s third fund, with previous investments being Instacart, DoorDash, Managed by Q. In the past he has also been a consultant to some of the leading funds in the valley including the likes of Kleiner Perkins, DFJ, General Catalyst and more. If that was not enough, Shah also has an extensive career in media having been a contributor for both TechCrunch and the Harvard Business Review in the past. Due to all of this Shah was listed by Marc Andreesen as one of his '55 Unknown Rockstars in Tech'. 

In Today’s Episode You Will Learn:

1.) How Semil made his way into VC? How did he come to create Haystack?

2.) What were the challenges and concerns for Semil in raising and establishing his own fund?

3.) Question from Michelle Tandler: How does Semil send deals through to Series A? What is his 'cool' process? What are the commonalities of those that make it to Series A and those that do not?

4.) How has Semil approached the aspect of personal VC branding? How does he evaluate the rise of the personal VC brand in the last few years?

5.) Why does Semil believe he is not 'founder friendly' in the conventional sense?

Items Mentioned In Today’s Show:

Semil’s Fave Book: Burmese Days by George Orwell

Semil’s Most Recent Investment: AquaCloud

Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies. Woody joined TCV in 1995 and has since led investments in Spotify, Netflix, AirBnB, Peloton, Groupon and the list goes on. Due to this phenomenal success, Woody has been named numerous times to the Midas List by Forbes as one of the industry’s top technology investors. Prior to joining TCV, Woody spent 12 years at Trident Capital, where he focused on the payments, internet, and mobile markets.

In Today’s Episode You Will Learn:

1.) How Woody made his way into the world of VC over 23 years ago and came to invest in products of a generation such as AirBnb, Spotify and Netflix?

2.) What have been the foundational changes Woody has seen over his last 23 years in venture? How did witnessing the boom and bust affect his operating and investing mentality? How does Woody approach price sensitivity? When is stretching on price a stretch too far?

3.) How does Woody analyse and assess the extended period of privatisation for companies today? How does the mega raises of funds from Softbank, Sequoia, GC, Lightspeed etc change the competitive landscape for Woody? Is there a surplus of capital in market today? Why does Woody believe the pie is larger than it has ever been?

4.) Does Woody agree that the dominant role of CEO is management upscaling? From Woody's portfolio, on hearing this, who is the first CEO that comes to mind and what is the story behind it? What are the mistakes that CEOs tend to make most often when scaling into hypergrowth? What are the 2-3 things that all companies need to focus on when product market fit is apparent and they need to scale?

5.) Woody has spent over 3,500 hours in the board seat, how has he seen himself evolve and develop over time as a board member? What were the biggest learning curves and points of development for Woody? How do the best founders manage and operate their board? Who exemplifies this best from recent memory? What do they do?

Items Mentioned In Today’s Show:

Woody’s Fave Book: The Boys in the Boat

Woody’s Most Recent Investment: Peloton

As always you can follow Harry, The Twenty Minute VC and Woody on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Adam Grenier is an OG of the growth world. His first role in growth, was none other than Uber where he was Head of Growth Marketing and Innovation building the global marketing growth infrastructure and team from the ground up. He then enjoyed successful spells at Lambda School and Masterclass as VP Growth and VP of Marketing, respectively. If that was not enough, Adam is also a prolific angel having made investments in Superhuman, Table22, and FitXR to name a few.

In Today's Episode with Adam Grenier We Discuss:

1.) Entry into the World of Growth with Uber:

• How did Adam make his way into the world of growth with Uber and Ed Baker?
• What are the single biggest takeaways from his time at Uber, Lambda and Masterclass?
• What does Adam know now that he wishes he had known when he started in growth?

2.) Growth: What it is? Why You Do Not Need a Team for it?

• How does Adam define the term "growth" today? What is the role of "Head of Growth"?
• Why does Adam believe that you do not need a growth team?
• How can leaders infuse growth principles, mindsets and metrics into existing teams?
• WHat are the single biggest mistakes founders make when thinking about growth?

3.) Hiring Growth Mindsets: How to Ask the Right Question:

• What are the clearest signs to Adam that someone has a growth mindset?
• What are the right questions to ask to see how they think?
• How does Adam use tests and case studies to determine the growth mindset of a person?
• What did Uber teach Adam about the best practices to hire for growth?

4.) Uber: Scaling a Monster and Spending $1BN on Ads:

• What are some of Adam's biggest lessons from spending $1BN on advertising at Uber?
• Why at anytime were there 200 people paying for ads with their personal credit cards?
• Why does Adam believe China was "the wild-west"? How did all of their competitors in China have Uber data?
• How do growth mechanics, channels and disciplines compare between US vs China?

Elena Verna is a master when it comes to all things starting and scaling growth organizations. Previously, Elena spent over 7 years as SVP Growth @ SurveyMonkey where she ran product, growth marketing, and data teams. Post SurveyMonkey, Elena worked with the rocket ship that is Miro both as Interim CMO and as an advisor. Elena has also advised some of the best growth orgs with advisor roles at HP, MongoDB, Netlify, Maze, and many more awesome companies.

In Today’s Episode with Elena Verna You Will Learn:

1.) How Elena made her way into the world of tech and growth from a Craiglist job listing? What was her big break in the world of growth with her first Head of Growth role?

2.) How does Elena define "growth" and "Head of Growth"? When should startups not have a growth team? What are the 3 main levers to the growth model today? How does Elena advise between hiring a CMO vs Head of Growth? Where do many founders make mistakes with this decision in mind?

3.) Who are the wrong people to hire for your growth team? What characteristics and traits do these people have that make them bad for growth? What questions does Elena ask in interviews to determine if they have these traits? How does Elena advise founders structure the process of hiring their "Head of Growth"? Should it be internal promotion or external hire?

4.) Where do most founders go wrong in the onboarding phase of their growth team? What do you have to have in place before the growth team starts? What are the biggest red flags for founders when reviewing their growth teams in the first 3 months? Why does Elena not like post-mortems? What is the optimal relationship between CEO and Head of Growth?

5.) How can growth teams work most effectively with both product and engineering teams? How do they need to communicate to ensure a healthy relationship? Where do growth teams most often make mistakes here? What have been some of Elena's lessons on how growth can experiment without angering engineering teams?

Nicolai Tangen is the CEO of Norges Bank Investment Management, the largest sovereign wealth fund in the world with $1.55 Trn in assets, owning on average, 1.5% of every listed company. Tangen was previously Chief Executive Officer and Chief Investment Officer in AKO Capital, which he founded in 2005. Prior to this, Tangen was a partner and senior analyst at Egerton Capital and an equity analyst at Cazenove & Co.

In Today's Episode with Nicolai Tangen We Discuss:

From Religious Town in Norway to Leading the Largest Sovereign Wealth Fund:

• What was Nicolai like as a child? How would his parents have described him?
• Why does Nicolai think that loners have a greater chance/ability to make money?
• What does Nicolai know now that he wishes he could tell a 20-year-old Nicolai?

The Top 10 Questions:

1. US Tech Firm Concentration: Is Nicolai concerned by the concentration of enterprise value in US tech firms? Have incumbents ever been as strong as they are today?

2. Impact of AI: What does Nicolai believe the impact of AI will be on society and productivity? What is his approach to investing in it moving forward?

3. Bitcoin: Why does Nicolai not want to hold Bitcoin? Why does he not understand it?

4. China: What would need to happen for China to be investable? How will the China situation play out?

5. Europe: Does Nicolai believe Europe is so far behind the US? Why? What can we do to improve?

6. Climate Change: How does Nicolai approach investing in climate? What works? What does not?

7. Sam Altman: Would Nicolai invest in Sam's new $7Trn project? What are some of Nicolai's biggest lessons from the time he has spent with Sam?

8. Investment Psychology: How does Nicolai retain a neutral investor psychology? How does he not get too up when doing well and too low when not doing well?

9. Investing Lessons: What are Nicolai's biggest investment hits and misses? What did he learn from them?

10. The Future: Why is Nicolai so optimistic about the future? What is he concerned about? How will we overcome our greatest challenges?

Nico Wittenborn is the Founder of Adjacent, one of the best early-stage firms created over the last 5 years. Before starting Adjacent, Nico spent over 3 years at Insight Partners in New York and before that learned the craft of venture from some of the best in early-stage, Point Nine, where he spent over 4 years. Nico's portfolio across funds includes the likes of Revolut, Chainalysis, Oura, RevenueCat and PhotoRoom to name a few.

In Today's Show with Nico Wittenborn We Discuss:

1.) From Selling Mobile Phones to Leading Early-Stage Investor:

• How did Nico first make his way into the world of venture with Point Nine?
• What did Nico learn from his time with Point Nine and Insight? How did his time at each impact how he invests and runs Adjacent today?
• What does Nico know now that he wishes he had known when he started investing?

2.) Is Consumer Subscription Even a Good Place to Invest?

• With Calm ($2BN) and Duolingo ($6BN) as the market leaders and there only being two of them, is consumer subscription even a good place to invest?
• How does Nico pushback that retention for consumer subscription apps is so bad? What do many not see about consumer subscription retention numbers?
• How does Nico respond to the challenge of high customer acquisition cost and navigating challenging platform shifts in advertising, when investing in consumer subscription?
• What will the consumer subscription landscape look like in 5 years time?

3.) Adjacent: The Fund, The Strategy:

• Why does Nico believe if your fund model relies on $10BN outcomes, you are in trouble?
• How large is the latest Adjacent fund? What does the portfolio construction look like for the fund?
• How much diversification is the right level of diversification? How many companies per fund?
• How does Nico think about capital concentration on a per company basis?
• What are Nico's ownership requirements? How have they changed with funds?
• What is it about Nico's structure which enables him to be more collaborative than others?

4.) Nico: The Investor: Lessons:

• How does Nico reflect on his own relationship to price? When does he pay up? When does he not?
• What has been one of Nico's biggest misses? How has that changed his approach?
• Why does Nico not really compete with the large multi-stage funds?
• Why is Nico deliberately trying to reduce the amount of companies that he sees?

5.) The Future of Venture:

• How does Nico analyze the rise of solo GPs? What are the biggest pros and cons of the model?
• Why does Nico believe the large generalist funds are in trouble?
• Who is set to win and who is set to lose in the next 10 years of venture?
• Which seed firm would Nico invest in? Which Series A firm? Which growth firm?

Guillaume Pousaz is the Founder and CEO of Checkout.com, one of the world's leading global payments solutions providers and one of Europe's most valuable private companies. Guillaume founded Checkout.com in 2012 and bootstrapped the business until its record-breaking $230M Series A led by Insight and DST in 2019. Since, Guillaume has raised a further $600M for Checkout from the likes of Coatue, Tiger, Blossom, GIC and Greenoaks. As part of this process, Guillaume has scaled the team to over 900 people around the world and Checkout as one of the category leaders in payments with a reported $15Bn valuation.

In Today’s Episode with Guillaume Pousaz You Will Learn:

1.) How Guillaume made his way into the world of payments following a travelling experience? How that experience led to his founding the now $12Bn, Checkout.com?

2.) Why did Guillaume wait 7 years into the running of the business before raising a massive $230M Series A? Why was then the right time? Was it a difficult mental transition to move from lean, capital efficiency to raising $230M? Why have Checkout never spent a single dollar on marketing? Is it true, Checkout has never spent a single dollar you have raised?

3.) What does Guillaume mean when he says he "has 3 roadmaps for life"? How does he structure his planning for the next 2,5 and 10 years? How does Guillaume think on his own identity and how it is tied to Checkout, the company? How does Guillaume advise founders in terms of tying their identity to their company?

4.) Why does Guillaume believe that becoming a father made him a better CEO? How did it impact his operating style? How does Guillaume analogise the role of the CEO to the profession of being a sailor? How does Guillaume think through his relationship to money today? How has it changed over time? How does he think about ensuring it does not impact his children?

5.) In what way does Guillaume structure his decision-making process today? What does Guillaume believe it is about the velocity of decisions that determine the quality of the leader? What topics does Guillaume struggle to make fast decisions on? What advice does Guillaume give to founders in situations when you just do not know what to do?

Item’s Mentioned In Today’s Episode with Guillaume Pousaz

Guillaume’s Favourite Book: Dune by Frank Herbert

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Scott Sandell is the Managing General Partner of NEA, one of the leading firms of the last 3 decades with now close to $24Bn under management and a portfolio including Salesforce, Robinhood, Plaid, Databricks and more. As for Scott, since joining the firm in 1996 he has led investments in Salesforce.com, Tableau Software, WebEx and Workday and serves on the board of Robinhood, Cloudflare, Coursera and Divvy to name a few. 

Rick Yang is a General Partner and Head of Consumer Investing @ NEA, since joining in 2007 he has led investments in the likes of Masterclass, Plaid, Robinhood and many more.

In Today’s Episode with Scott Sandell and Rick Yang You Will Learn:

1.) How Rick came to meet Vlad, Robinhood Founder, for the first time? What impressed Rick most in that first meeting? How did the internal discussions proceed at NEA? Was it a unanimous decision to make the investment?

2.) The Market:

• How did Rick and Scott evaluate the market at the time? Bottoms up, top down?
• How did the market change and evolve both in ways they did and did not expect?
• How do Rick and Scott evaluate market timing risk today when investing?
• How did Rick and Scott approach outcome scenario planning with Robinhood?

3.) The Traction:

• What core signals and datapoints made Rick realise Robinhood had product-market-fit?
• How did Rick and NEA analyse Robinhood's early organic customer acquisition? How did the board advise on how to spend their first marketing dollars?
• How does the cost structure of the business compare to Charles Swaab and eTrade? Why is Robinhood such a superior model?

4.) The Team: 

• How has Vlad evolved and developed as a leader over time?
• How did Vlad handle the 36 hours in Feb 2021 when he had to go and raise $3BN+?
• Who is the unsung hero of the Robinhood team? What have they done to deserve this?

Mario Schlosser is the Co-Founder and Chief Technology Officer at Oscar Health. The public company that went public with a market cap of $7.1BN. Following a tumultuous time in the markets, their stock price dropped 94%. Today, the company has rebounded and has a market cap of $3.2BN with an astonishing $5.8BN of revenues. Before co-founding Oscar, Mario also co-founded the largest social gaming company in Latin America.

In Today's Episode with Mario Schlosser We Discuss:

1. From German Middle-Class to Public Company Founder:

• How did Mario make his way into the world of tech and come to co-found Oscar with Josh Kushner?
• Does Mario agree with Jensen Huang that "we should all have lower expectations"?
• What does Mario know now that he wishes he had known when he started Oscar?

2. Why Did Oscar Tank 94% in the Public Markets:

• What was the core reason why Oscar tanked 94% in the markets?
• What would Mario have done differently knowing all he knows now about public markets?
• Does Mario regret going public? What are the biggest pros and cons?

3. The Mental Challenge of a 94% Market Cap Decline:

• How did Mario mentally deal with the company being down 94%?
• What does he say to himself in the truly hard times?
• How did Mario use his co-founder, a coach and his family, to get through the really bad times?
• What are Mario's experiences like with anti-depressants? What worked? What did not?

4. Firing Yourself as CEO:

• Why did Mario decide to step aside as CEO? What was the decision-making process?
• On reflection, does Mario think he was a good CEO? Where was he good? Where was he bad?
• What are the biggest management pieces of advice that Mario thinks are BS?

Brendon Cassidy is one of the OG of enterprise sales of the last decade, having advised the likes of Gong.io, Pipedrive, Showpad. Previously Brendon was first Head of Sales at LinkedIn and VP of Sales at Talkdesk.

In Today's Episode with Brendon Cassidy We Discuss:

1. From Recruiter to Sales OG and Linkedin's First Head of Sales:

• How did recruiting prepare Brendon for a career in sales?
• What impact did the dot-com bubble burst have on his early career?
• What does Brendon know now that he wishes he had known when he started his career in sales?

2. The Sales Playbook and Hiring The Team:

• How does Brendon define the "sales playbook"?
• Should the founder be the one to create and execute V1 of the playbook?
• Should the first sales hire be a rep or a sales leader?
• When is the right time to make that all-important first sales hire? 

3. Why Discovery and Outbound Are Broken Today:

• Why does Brendon feel discovery is useless in today’s sales process?
• Why does Brendon believe outbound will move under the marketing function?
• How does AI change the world of outbound sales?
• Why will no great sales leaders join a company that doesn’t have an inbound machine?

4. How to Master Onboarding and Increase Sales Performance:

• What is the right way to onboard new sales reps?
• How quickly do you know if a sales rep is not good? What are the signs?
• What is the right way to measure the effectiveness of sales teams today?
• What are the biggest mistakes founders make in onboarding sales teams?

Brendan Wallace is the Co-Founder and Managing Partner @ Fifth Wall, the fund with the core thesis being the physical world around us is colliding with technology. Within their portfolio is the likes of Lime, OpenDoor, Clutter, ClassPass, Lyric and Hippo just to name a few. As for Brendan, before co-founding Fifth Wall he co-founded Identified, a data & analytics company focused on workforce optimization that was acquired by Workday in 2014. Prior to that, Brendan co-founded Cabify, the largest ridesharing service in Latin America. If that was not enough, Brendan has been an active angel investor having led over 60 angel investments including Bonobos, Dollar Shave Club, Lyft, SpaceX, Clutter, Philz Coffee and Zenefits.

In Today’s Episode You Will Learn:

1.) How Brendan made his way from founding the largest ridesharing platform in Latin America to changing the face of early stage real estate and consumer retail investing with Fifth Wall?

2.) What is really going on in retail today? Is "retail apocalypse" a fair term to give to the landscape today? What formats does physical retail no longer work for? What is it perfect for? How does Brendan think about the distribution of physical retail for emerging brands? Will they need 1,000s of stores or is the 1,000 store brand era over?

3.) Why do digitally native brands fundamentally need retail? How much of consumer US spend relies on physical retail still today? When do these DNVB's need to expand into physical retail? From speaking to DNVB CEO's what are the most common challenges they face when making the expansion?

4.) How does expanding into physical retail change the game in terms of customer acquisition for DNVBs? At what point do DNVBs hit the invisible asymptote where acquiring customers through traditional online channels is no longer efficient? How have Amazon impacted the CACs for DNVBs in recent years?

5.) Given the consumer retail focus of the fund, one would expect a lower loss ratio, is it right to assume the lower loss ratio? How does Brendan think about portfolio construction with the fund? How does reserve allocation differ when investing in physical retail vs pure software plays? Is Brendan concerned by the lack of downstream capital in the physical retail space?

6.) How does Brendan assess outcome potential when comparing physical retail to pure software plays? Why des Brendan believe we will see a ton of intermediate outcomes? How does this change the type of entrepreneur that Brendan looks to back with the retail fund?

Items Mentioned In Today’s Show:

Brendan’s Fave Book: The Great Gatsby

Brendan’s Most Recent Investment: Heyday

As always you can follow Harry, The Twenty Minute VC and Brendan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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Elias Torres is the Co-Founder and CEO of Agency, the AI agent for customer success teams. Prior to Agency, Elias was the Co-Founder of Drift, a company he sold to Vista for $1.2BN Before that he started Performable, which he sold to Hubspot. 

In Today’s Episode We Discuss:

03:50 Do Rich Founders Make Better Founders: How Backgrounds Shape You

06:23 Speed: Why are Incumbents Slower than Ever

10:00 Quality: Why are Incumbents Worse than Ever

25:34 Why Was Selling Drift For $1.2BN a Massive Failure

33:30 How Did a Cushy Culture Kill Drift

37:01 What They Never Tell You About Selling for $1.2BN

41:08 How to Hire F******* Rockstars

46:52 The Biggest Mistakes Founders Make in Hiring

54:52 Everything You Think You Know About Working Parents is Wrong

01:02:00 Quickfire

Jiaona “JZ” Zhang is the Chief Product Officer at Linktree, the world’s leading link-in-bio platform empowering 45M+ creators, brands and SMBs. JZ joined Linktree from Webflow, where she served as SVP of Product. Before that, she spent four years at Airbnb where she built and led numerous teams on the host side. JZ’s also held leadership roles at the likes of Wework, Dropbox and teaches at Stanford University and Reforge.

In Today’s Episode with Jiaona Zhang We Discuss:

1. Entry into the World of Product

• How did JZ first fall in love with product?

• Why does JZ believe the best PMs have experience in the gaming industry?

• Does JZ think Linktree could be a $100BN business? How could Linktree become a $100BN business?

2. Mastering Product Metrics

• Why does JZ think product is the most chameleon role? Where does product start & end? 

• Why does JZ think every function should have tension with product?

• What is a KPI tree? How does JZ branch business & product metrics?

• When does JZ think startups should set up a metric infrastructure?

• What are the three levers of product? How does JZ determine which ones to trade off?

3. How to Run Product: Planning, Strategy, & Rituals

• Why does JZ think planning should not exist?

• What are strategy and rituals? When should founders do either?

• What are JZ’s three core rituals?

• What is the scorecard method? How do they help team transparency?

• What are product jams? When does it work? When does it not work?

4. Product Career Advice

• When does JZ think founders hire a product person? 

• What are the most common mistakes early stage founders make when hiring for product?

• Does JZ think domain expertise is important? What does she look for in product hires?

• What is JZ’s advice to PMs who want to get promoted today? 

• What is JZ’s advice to young people who want to get into product?

Hugo Barra is the OG of consumer hardware of the last decade. In Hugo's current position, he is the CEO @ Detect, building tools that empower people to understand their health and make informed, timely decisions. Before Detect, Hugo spent an incredible 4 years as VP of VR @ Meta with Oculus. Prior to Oculus, Hugo was in China as VP of Global @ Xiaomi, the 3rd largest phone maker in the world. Finally before Xiaomi, Hugo was a product leader @ Google for over 5 years including as VP of Android Product Management.

In Today's Episode with Hugo Barra We Discuss:

1.) Entry into Product:

• How did Hugo make his way from Brazil to Silicon Valley and Beijing Product OG?
• What is one takeaway from Google, Meta, and Xiaomi that influenced the way Hugo approaches product today?
• What is 996 Chinese work culture? How does the experience of working and leading teams in China impact his approach to team building today?

2.) The Secret to Success in Hardware:

• Why is hardware so much harder than software? What are the main differences?
• What are the biggest challenges faced when building V1 and V2 in hardware? How much do you rely on data vs gut and intuition?
• What are some of Hugo's biggest consumer product hardware failures? What did he learn from them?

3.) Feature King vs Budget King:

• Previously Hugo has said, "in the beginning, there is only two types of consumers." What does he mean by this? How does that impact his approach to product building?
• Can a budget king product leader also be an amazing feature king leader? What is the difference in the two? Why is it harder to be a budget king product leader?
• What happens if you have both budget king and feature king in one product? What happens then?

4.) Product Management 101:

• How does Hugo define product management today? What does it really mean to Hugo?
• Gustav @ Spotify has said before, "details are not details, they are the product." How does Hugo think about this statement in terms of great product management today?
• When do product orgs start to break down? What are the catalysts? What can be done to stop this?

5.) Brand Marketing vs Product Marketing:

• What is the difference between product and brand marketing?
• Why does Hugo believe you should always start every product build with the press release? What is the difference between good and great in a press release? What do the best have?
• What are the single biggest mistakes founders and product leaders make in storytelling today?

6.) Masterclass in Hiring:

• Why does Hugo do 3-and-a-half-hour interviews when hiring new candidates?
• What are the benefits of their being so long? What does he want to achieve?
• What core questions does he ask every time? What differentiates good from great?
• How does he get people to really open up and show true vulnerability?

John Doerr is an engineer, venture capitalist, the chairman of Kleiner Perkins, and the author of the #1 New York Times best-seller Measure What Matters. For over 40 years, John has helped build some of the most generational defining companies of our generation. He was an original investor and board member at Google and Amazon, helping to create more than a million jobs. A pioneer of Silicon Valley’s cleantech movement, John has invested in zero emissions technologies since 2006. Check out his latest book, Speed & Scale: An Action Plan for Solving Our Climate Crisis Now.

In Today’s Episode with John Doerr You Will Learn:

1.) What was John's entry into climate change investing? Having backed the likes of Amazon and Google, why did John decide then was the right time to do a climate fund, a pandemic fund, an iPhone fund? How does John think about market timing risk today? How does John determine between risks he is vs is not willing to take?

2.) What was one of John's biggest lessons on risk and upside from working alongside Tom Perkins? How did the Google deal come together? Where did John first meet Larry and Serge? What convinced John to write them a $12M check for 12% of the company? Why was it a contested deal within the partnership? How did the discussion go internally?

3.) Why and how is climate innovating and investing different today than it was in 2008? What are the core OKR's laid out in the book, that we need to achieve as a society? Why does John believe that governments are the biggest problem to us achieving these objectives? What does John mean when he says, "I am hopeful but not optimistic"?

4.) What does truly great listening mean to John? How would John describe his style of board membership? What do the truly special board members do? What does John do that makes him often cited as one of the best at recruiting? What is John's biggest investing miss? How did it change his mindset and approach? What investment is John most proud of, that no one knows? 

Item’s Mentioned In Today’s Episode with John Doerr

John’s Favourite Book: How to Avoid a Climate Disaster: The Solutions We Have and the Breakthroughs We Need

Ryan Wiggins is the VP of Growth and Analytics at Mercury where he oversees a Growth team and founded the Analytics function. Prior to this, Ryan built Growth teams at WhatsApp, where he helped grow WhatsApp Business from 0->100M users, Workplace, and Facebook Ads. If that was not enough, Ryan is also an active angel investor.

In Today's Episode with Ryan Wiggins We Discuss:

1.) From US Department of Commerce to Leading Growth Teams:

• How Ryan made his initial foray into the world of growth with Facebook and Whatsapp?
• What does Ryan know now that he wishes he had known when he made the entry into growth?
• What advice does Ryan have for people who want to change their career but are not sure what they want to do?

2. ) Who and When: Building the Team:

• Should we hire a Head of Growth or a more junior growth hire first?
• What are the different profiles of growth hires? How do they change with business model?
• When is the right time to hire your first growth hire?
• What are the single biggest mistakes founders make on the timing of growth hires?

3.) How to Hire: The Process:

• Structurally, what is the right way to hire for a growth team? What does the interview process look like? What do you want to get out of each meeting?
• Should case studies be used, if so, should they be used for the company hiring or of the company where the candidate is from?
• What does the comp package look like for different growth hires?
• Who should be brought into the growth hiring process? What stage should they be involved?

4.) Onboarding: Setting Growth Up for Success:

• What is the ideal first 30,60 and 90 days for new growth hires?
• What can leaders do to ensure they are set up for the maximum chance of success?
• What are three of the biggest red flags bad growth hires show in the first 30 days?
• What are the biggest mistakes founders make in the onboarding process of growth hires?

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all Intercom’s R&D efforts, and parts of Intercom’s marketing.

In Today's Episode with Des We Discuss:

1. From Consultancy to Founding a Unicorn:

• What was the founding a-ha moment for Des and the team with Intercom?
• Why does Des believe that most startup advice is BS and outdated in 5 years?
• What does Des know now that he wishes he had known when he started?

2. LLMs: The World is Not Equal:

• What does Des mean when he says the world of LLMs is not equal?
• How do the different LLMs very in quality, price and speciality?
• Does Des agree with Alex @ Nabla, "the best companies in the future will work with many LLMs at the same time and switch between them for different things"?
• To what extent does Des believe LLMs will be commoditised and it will be a race to the bottom?
• Would Des be a buyer of OpenAI at a $90BN price? Why not?

3. How to Survive in a World of OpenAI:

• What two simple questions will determine if Open AI will kill your existing business?
• What 3 criteria will determine if there is a new business to be built on top of OpenAI?
• What is the different between a thin layer on top of an LLM and a thick wrapper with real value?
• Which traditional incumbents are most vulnerable? What should they do in this new world?
• How long does it take for incumbents to really be impacted?

4. The Titans of Tech: Who Wins:

• Why does Des believe that Apple could be a massive winner in the next wave of AI?
• Why does Des believe that Google have not been impressive and failed to keep pace?
• Why does Des think OpenAI should be wary of Amazon? What could they do to threaten them?
• What opportunity does Facebook have here? How could Instagram and Whatsapp win?

5. Startup and Investing 101:

• Why does Des believe that every founder should write a blog post per week?
• Why does Des believe that most B2B marketing sucks? What makes great B2B marketing?
• What are Des' biggest lessons from the Hopin journey?
• How has Des' angel investing changed in the last year with the rise of AI?

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M in backing from individuals including Peter Thiel and Mark Cuban and it has been reported that the firm now has over $1B in assets under management. Nick has led seed investments in OpenSea, dYdX, SuperRare, Polkadot and Cosmos among others. Prior to 1confirmation, Nick was a Principal @ Runa Capital and before that led business development and marketing at Coinbase in the early days of the company.

In Today's Episode with Nick Tomaino We Discuss:

1. From Cryptokitties to founding the Leading Seed Crypto Firm:

• How did Nick first come into contact with crypto and bitcoin specifically?
• How did getting fired from Coinbase catalyse his move into venture?
• What does Nick know today that he wishes he had known when he started investing?

2. The Landscape Today: Funds and SBF

• Are the current generation of crypto funds too large? Should they give money back to their LPs?
• Will the next generation of crypto funds be smaller? Are any crypto funds able to raise right now?
• Why does crypto Twitter hate crypto VCs? Who are the worst VCs for pump and dump?

3. SBF & FTX: What Actually Happened, Who is to Blame, What Happens from here?

• What is the biggest misconception on SBF and FTX today?
• Who should be held accountable? What else would Nick like to see?
• How should FTX change the way that LPs invest into venture managers?

4. How to Build the Best Crypto Portfolio in Venture:

• How large are the funds? How does Nick determine the right size for a fund?
• How many investments does Nick make per fund? How do loss rates look in crypto?
• What have been Nick's biggest investment hits and losses? How did that impact his mindset?

5. The Future for NFTs and Opensea:

• Why does Nick remain bullish on the future of NFTs?
• How is Nick able to remain optimistic about the future of Opensea given their volumes?
• Where does Nick believe the fair price for Opensea should be today?
• Did Nick sell their Opensea at the $13Bn round?

Shoaib Makani is the Co-Founder & CEO @ KeepTruckin, the modern fleet management platform building solutions that make drivers and fleets safer, smarter, and more efficient. To date, Shoaib has raised over $229M from some of the world's leading investors including Index, GV, Greenoaks, IVP & Scale Venture Partners. Pre-founding KeepTruckin, Shoaib was an investor @ Khosla Ventures where he led investments in Instacart, Everlane and Indiegogo to name a few. Before venture with Khosla, Shoaib was on the operations side enjoying roles at both Google and Admob.

In Today’s Episode You Will Learn:

1.) How Shoaib made his way from the very comfortable world of venture to changing the way trucking fleets are managed today with KeepTruckin? How does Shoaib analyse and assess his own attitude to risk today?

2.) How has Shoaib seen himself change and evolve as a leader over the last few years? How did his time investing impact how he approaches the role of CEO? How does Shoaib think about appropriate market sizing today? What advice does he give to founders on this? What is a reasonable market penetration to assume if successful?

3.) What advice would Shoaib give founders when it comes to successful board management? How does Shoaib ensure investors have the right context at the right time to provide advice? What does that information flow to investors look like? How does Shoaib determine between the advice to accept vs what to reject?

4.) Shoaib thought about distribution and customer acquisition long before he launched the product, why? What did this thought process conclude with? Does Shoaib believe you have to own your own lines of distribution to succeed? How does Shoaib feel when it comes to current CAC's on incumbent platforms?

4.) As a founder, what does Shoaib say is his biggest mistake made in the KeepTrickin journey? How does Shoaib think about what it takes to acquire the very best talent? How does Shoaib advise founders work with recruiters? What can they do to really get the most out of them? When can this function be brought in house?

Items Mentioned In Today’s Show:

Shoaib’s Fave Book: Presidents of War

As always you can follow Harry, The Twenty Minute VC and Shoaib on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeff Russakow is the CEO @ Boosted, the startup producing vehicle grade electric skateboards rethinking how we travel. To date, they have raised $74m in funding from the likes of Khosla Ventures, iNovia Capital, Andreessen Horowitz and our friends at Initialized. Prior to Boosted, Jeff was CEO @ Gimbal where he doubled revenue in his first year and added 80 new enterprise clients. Before that, Jeff was the CEO @ Findly where he grew the company to 450 employees and 20m end users. Jeff also enjoyed prior roles with the likes of Symantec, Adobe, SAP and Yahoo.

In Today’s Episode You Will Learn:

1.) How Jeff made his way from leading enterprise CEO to re-thinking the way we travel today as CEO of Boosted?

2.) How does Jeff analyse the current sentiment to fundraising in the valley, specifically with regards to business construction? How has Jeff seen the investor class fundamentally transition over the last 20 years? When approaching investor selection, what is the 1 question that Jeff always asks? Where do founders often make mistakes here?

3.) Having raised the $60m round in 2018, how does Jeff approach the theme of capital efficiency today with Boosted? How does Jeff determine when is the right time to pour fuel on the fire? Why is Series B often the most challenging phase when considering the focus on unit economics and vision simultaneously?

4.) What is Jeff's gut reaction to the statement, "hardware is hard"? Why does Jeff feel this to be a glib statement that misses the point? How does Jeff respond to the criticism of the commodity element of hard, easy to replicate and copy? How would Jeff like to see the investor class change their mindset to hardware? What is the right way to approach it?

5.) What are the core elements required for a successful CEO transition? For a potentially incoming CEO, what must they be wary of with regards to the information conveyed to them by investors of the company? Where has Jeff seen many go wrong in CEO transitions? What can the founders do to make this process as smooth as possible?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Missing Piece 

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jack Brody is the VP Product @ Snap. Jack joined Snap in 2014 as a Product Designer, and ultimately helped build out the design organization as the Head of Design before taking on his current role overseeing all of Product for the Snapchat application and Hardware. In his 9 years at Snap, he helped create Memories, the Snap Map, and AR Lenses like Face Swap.

In Today's Episode with Jack Brody We Discuss:

1. The Shortest Internship in Tech:

• How did Jack get an internship with Evan Spiegel and Snap while he was still at college?
• How did it turn into the shortest internship in tech history?
• What are the single biggest product lessons Jack has from working with Evan Spiegel?

2. Product 101: Art vs Science:

• Does Jack believe product is more art or science? If he were to assign numbers to them, what would they be?
• How does Jack define creativity? What can founders and product leaders do to ensure their teams are as creative as possible?
• What is the 3 step framework through which product leaders should prioritize product ideas?
• Does Jack believe that when the CEO is no longer the Head of Product, the company is dead?
• Does Jack agree with Gustav Soderstrom, "talk is cheap, so we should do more of it"?

3. The SNAP Hiring Process: What Works and What Does Not:

• What is the hiring process for the product team at SNAP?
• What questions are most revealing of 10x product people in the interview process?
• What case studies and tests does Jack use in the interview process?
• What other roles and functions does Jack bring into the interview process as part of the decision?
• What are the single biggest mistakes founders make in the hiring process for product?

4. SNAP, The Future, and The World Around Us:

• What do Jack and SNAP believe will be the future for augmented reality?
• What country is SNAP not big in today but will be in the next 5 years? Why that one?
• Why did SNAP tear down its android app and start again? What has been the impact?
• Were the SNAP glasses a success? What is their future?