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18 Feb 202269. When to sell your startup? ‍♂️ Equity and Valuation vs. Risk00:13:11

When to sell your startup? 🤷‍♂️ Equity and Valuation vs. Risk

When should you take an offer for your startup?

What is the risk of continuing vs. the immediate reward?

 

It is critical to consider if and at what price you would consider selling your company before the offer arrives. When it does, the big $$$ may muddle your thinking.

In this episode, I discuss how to systematically analyze these questions and share my experiences selling my first company.

 

Watch the video: https://ftb.bz/69V

Read this as a blog: https://ftb.bz/69B

Sign up for one-on-one coaching: https://ftb.bz/Join

Join the Founders Alliance: https://ftb.bz/Alliance

See our other videos on running your startup: https://ftb.bz/Running-your-startup

All the rest of our playlists and videos: https://ftb.bz/Channel

11 Feb 202268. How to recruit the perfect advisors (or directors) for your startup00:09:11

Recruit startup advisors 👨‍🦳 board of directors

Your advisors can make or break your startup

Learn how to identify and recruit the perfect startup advisory board

 

Read the blog: https://ftb.bz/68B

Watch the video: https://ftb.bz/68V

Join us to access free one-on-one office hours: https://ftb.bz/Join

Meet other entrepreneurs at the Founders Alliance: https://ftb.bz/Alliance

 

In this episode I share a step by step method for building a startup advisory board or board of directors. You will learn how to identify and recruit advisors.

Advisors can help you with startup funding, angel investors, venture capital, pitch decks, growth hacking, startup marketing, product sales, PR, and more.

04 Feb 202267. Blitzscaling vs. the 4 hour work week – choose the kind of company you want to create and run.00:03:07

Blitzscaling 🤔 4 hour work week

What kind of startup do you want to create and run?

Be clear on your desires to achieve the journey and outcome you want.

Read the blog version here: https://ftb.bz/67B

Watch the video: https://ftb.bz/67V

Join the founder alliance: https://ftb.bz/alliance

In this episode I ask founders to think about the kind of startup journey and outcome they want. Consider things like bootstrapping vs. venture capital. Going for unicorn status vs. building a lifestyle business.

Are you open to working 100 hour work weeks, or are you looking for a 4 hour work week allowing time for your favorite activities?

Do you want to be a serial entrepreneur, ride this train all the way to the end of the line, or get a payout and retire?

27 Jan 202266. Pre-revenue startup funding: valuations & venture capital00:10:26

Learn how angel investors and venture capitalists determine your startup’s valuation

I share three formal methodologies and the secret technique most angels actually use

 

Join Feel the Boot to access one-on-on coaching https://ftb.bz/Join

Meet other founders in the Founders Alliance https://ftb.bz/Alliance

Read the full blog from this episode https://ftb.bz/66B

Watch the video https://ftb.bz/66V

 

Calculating preseed valuations can be tricky because you have little to no revenue to base it on.

Both Angel Investors and Venture Capital companies have a number of valuation methodologies they can use.

Startup funding requires setting a pre-money valuation for the company, which are the end point of a negotiation between the investor and the startup founder.

 

Related topics:

Pre-seed, slidebean, crowdfunding, equity, y combinator, startup pitch, pitch deck, startup news, startup grind, growth hacking, ycombinator, how to start an online business

19 Jan 202265. Task Management ✍️ make time for strategic thinking00:10:05

Task Management ✍️ make time for strategic thinking

Use these two time management and prioritization frameworks

to ensure you accomplish your high priority strategic objectives

 

Founders and CEOs can often get in the trap of working on mundane tasks while failing to take time to do the critical strategic thinking that will make the company soar. I found two frameworks that helped me in my startup, and I will walk you through them in this episode.

Read the transcript here: https://ftb.bz/65B

Watch the Video: https://ftb.bz/65V

Subscribe to our newsletter and get a link to schedule one-on-one office hours with me. https://ftb.bz/join

Meet other founder at the Founders Alliance. https://ftb.bz/Alliance

The “what does the business require of you” concept comes from the seminal book “The Effective Executive” by Peter Drucker. https://amzn.to/3fyEdg6

30 Dec 202164. Feel the Boot 2021 year in review00:04:31

2021 was a big year for us at Feel the Boot. We experienced lots of growth, and I want to thank all of you for making such a fantastic experience.

The best part of this year has been getting to interact with so many of you founders. I had many more one-on-one coaching sessions than in previous years. I've loved talking to so many of you. If you took advantage of them, I hope you have found them helpful.

I've learned a tremendous amount from getting to take a quick peek behind the curtain of so many different kinds of companies. Many of these conversations directly inspired the episodes you saw this year, and I'm sure they will continue to do so.

It's been interesting to see how COVID has impacted my angel investing and advising experience. When I used to do in-person meetings and in-person events, the drive times were significant. Now that I'm doing everything virtually, the massive expansion in the number of people I can help and the diversity of places they can come from completely altered the way I approach this whole business.

The scale I can achieve with an all virtual process is incredible. There's no way I'll be going back to the old way of doing things.

2021 has been a fantastic year for the YouTube channel. We've more than tripled in size.

We started the year with less than 200 subscribers and will end just a hair short of 600, and people watched our videos over 16 thousand times.

That number blows my mind because there's no possible way I would be able to reach anywhere near that many founders on a one-on-one basis.

It's been interesting to look at the year's most popular videos. I was surprised to see that the most popular ones tended to be quite technical. I will try to do more of those in the coming year.

The top three were:

Understanding stock options from the employee perspective https://ftb.bz/9V

How to create financials for early-stage pre-seed startups that will wow investors https://ftb.bz/28V

Nine things angel investors look for in startup fundraising pitches https://ftb.bz/31V

While I already have a long list of potential episodes, I'm always looking for new topics to cover. I want to create what you want to hear, so please reach out and let me know what episodes you'd like to see. You can do that by reaching out to me on social media. I'm most active on Twitter, Facebook, and LinkedIn. Or you can use the contact form at Feel the Boot.

This year also saw the introduction of Swift Kicks, a series of videos less than 1 minute in length.

They turned out to be very popular because I can post the whole video to social media rather than just a little bit of an introduction to it and then a link over to YouTube.

Some Swift Kicks are highlights from longer episodes, while others are short standalone answers to specific questions.

In 2022, I'm hoping to do more of everything. More videos, more shorts, and more one-on-one coaching with all of you.

We'll also be exploring some new kinds of content. Hopefully, I'll be putting out more materials that you can use as workbooks for your startup. I've got lots of ideas, but we'll see what I can manage to execute on along with everything else I've got going.

Thanks for coming along with me on this journey over the last year. It's been a great pleasure.

If you want to stay in touch, the best ways are following Feel the Boot on social media: https://ftb.bz/twitter  https://ftb.bz/LinkedIn https://ftb.bz/Facebook

If you want to stay in touch with other founders interested in this kind of Feel the Boot content, come to the Feel the Boot Founders Alliance https://ftb.bz/Alliance.

Until next time, next year, Ciao!

10 Dec 202163. Focus on the fundamentals to create a marketing strategy for your startup – Tim Fitzpatrick Interview00:46:48

Many founders skip the marketing fundamentals and strategic thinking and jump directly to executing on some set of ad-hoc initiatives.

Then they wonder why their marketing is not working.

While I have done a lot of marketing over the years, it is not my core expertise. So, I interviewed Tim Fitzpatrick with Rialto Marketing, who is an expert.

We talked about the fundamentals of marketing strategy and some great tips on implementing them in practice.

 

Table of Contents:

Missing the Fundamentals

Defining your target customer

Crafting the story

Creating a 90 day plan

What to measure

The power of channels

 

Links

Tim provided some free resources for you: https://www.rialtomarketing.com/feel-the-boot-the-science-of-startups/

Join other Founders for help, advice, and support at the Founders Alliance: https://ftb.bz/Alliance

About our guest Tim Fitzpatrick

Tim is an entrepreneur/business owner with expertise in marketing and business growth. He has 20+ years of entrepreneurial experience with a passion for developing and growing businesses. That passion served him well in operating and managing a wholesale distribution company he co-owned for nine years. The company grew an average of 60% a year before being acquired in 2005.

Since then, he’s had failures and successes that have been valuable learning experiences. He started Rialto Marketing in 2013 and has been helping service businesses simplify marketing so they can grow with less stress. Most people overcomplicate marketing. It doesn't have to be that way.

19 Nov 202162. Design your C-suite with care. Consider the next 2 years of your startup when handing out titles00:07:00

Job titles in startups are usually loosely defined and casually managed. In many cases, founders hand out very senior-sounding titles to their co-founders and early hires.

While everyone likes having a fancy-sounding job title, they can come back to bite the company later as it grows.

The one big title you need to have in the company is a CEO. Investors, partners, vendors, and employees all need to know who speaks authoritatively for the company. They are both the face of the company and the person with ultimate operational control.

Beyond that, in an early-stage company, titles are somewhat arbitrary. Sometimes they are silly or descriptive, but often founders give all the early employees very senior titles like CTO, CMO, or Vice President of whatever.

Early on, these inflated titles do little harm and can make everyone feel important. The problem comes later.

Check out the written version of this episode here https://ftb.bz/62B

Get the video version here https://ftb.bz/62V

Get all the other episodes on our website https://ftb.bz/

Get all the videos on our YouTube channel https://ftb.bz/YouTube

To get access to free one-on-one coaching with me, join our mailing list here: https://ftb.bz/Join

29 Oct 202161. Understand founder equity dilution and how your decisions impact what you keep.00:14:27

In this episode, I talk about dilution, the process by which your ownership in the company shrinks as you bring in investment. The decisions you make, and the terms you negotiate, can drastically alter your payout at exit.

Read the article version of this content here: https://ftb.bz/61B

Listen to the Podcast: https://ftb.bz/Podcast

Join Feel the Boot: https://ftb.bz/Join

Join the Founders Alliance: https://ftb.bz/Alliance

Get episode on control and ownership: https://ftb.bz/11B

20 Sep 202160. Top Insights From 25 Years as a Founder, Angel, and Advisor00:21:45

Podcast

I have learned a lot of things about business and the entrepreneurial experience over the last twenty-five years. During that time, I was a founder, CEO, Chief Scientist, angel investor, and startup advisor. I recently gave a live talk at the Founder Institute, where I talked about my most significant insights about the startup world, business, and life.

The attendees loved it, so I immediately started working on a version for Feel the Boot.

Get the blog here: https://ftb.bz/60B

Watch the video: https://ftb.bz/60V

Join Feel the Boot and get the link for one-on-one coaching: https://ftb.bz/join

Join the Founders Alliance group: https://ftb.bz/alliance

So, here are the insights in no particular order:

Validate early and often

You can't overcommunicate

Everything a founder says is amplified

Networking is not schmoozing

Get over your aversion to selling

Talk about benefits, not features

Understand the person across the table

Style and aesthetics matter

You don't scale, and delegation sucks

Startups are a marathon

20 Aug 202159. Asking your customer these questions can prevent massive wasted effort00:19:20

I noticed a pattern among founders I meet, and it is something I did too. We have an idea and immediately start working on it before validating it with our potential customers. In many cases, we have practically finished the product before we start showing it to people.

But, if we guessed wrong we have wasted a colossal amount of work.

I think I know why this happens. For technical founders, coding and development are our comfort zone. We're happiest when we're behind the keyboard in a dark room, banging out code and creating new software.

Creating that solution is why we founded the company in the first place. Also, for introverts, getting out and talking to people makes us uncomfortable. Also, we often feel that we already know what the customers want and need.

We know our customers and feel that we can stand in as a good model for them when designing our solutions.

Unfortunately, you're not a good model for your customers unless you're building a tool for people who are exactly like you. I made that mistake.

I was building the first stand-alone application version of Anonymizer. As a privacy passionate person, building for other similarly passionate people, I thought I could just make what I wanted for myself. The product was incredible. It provided very fine-grained control over all aspects of what information websites could collect and on which sites or pages they could collect it.

Our customers hated it, and even I rarely used most of the features. I was not even a good model for what I wanted myself!

After finally talking with our customers, the next version of the product had exactly one control: on/off. It was a huge hit.

My error had significant consequences. We spent many months focused on that first product, costing us money we could not afford to lose. It also significantly delayed our entry into the market with a solution people wanted to use. Once we realized the direction we needed to go, we had to scrap almost everything we had built.

It is almost impossible to get your app perfectly right the first time, and there is no substitute for the learning you gain when your product is in a customer's hands. But, the more you can learn, pivot, and iterate before you build anything, the faster and more efficient you will be.

I noticed a pattern among founders I meet, and it is something I did too. We have an idea and immediately start working on it before validating it with our potential customers. In many cases, we have practically finished the product before we start showing it to people.

I think I know why this happens. For technical founders, coding and development are our comfort zone. We're happiest when we're behind the keyboard in a dark room, banging out code and creating new software.

Creating that solution is why we founded the company in the first place. Also, for introverts, getting out and talking to people makes us uncomfortable. Also, we often feel that we already know what the customers want and need.

We know our customers and feel that we can stand in as a good model for them when designing our solutions.

Unfortunately, you're not a good model for your customers unless you're building a tool for people who are exactly like you. I made that mistake.

I was building the first stand-alone application version of Anonymizer. As a privacy passionate person, building for other similarly passionate people, I thought I could just make what I wanted for myself. The product was incredible. It provided very fine-grained control over all aspects of what information websites could collect and on which sites or pages they could collect it.

Our customers hated it, and even I rarely used most of the features. I was not even a good model for what I wanted myself!

After finally talking with our customers, the next version of the product had exactly one control: on/off. It was a huge hit.

My error had significant consequences. We spent many months focused on that first product, costing us money we could not afford to lose. It also significantly delayed our entry into the market with a solution people wanted to use. Once we realized the direction we needed to go, we had to scrap almost everything we had built.

It is almost impossible to get your app perfectly right the first time, and there is no substitute for the learning you gain when your product is in a customer's hands. But, the more you can learn, pivot, and iterate before you build anything, the faster and more efficient you will be.

 

Read this as a blog: https://ftb.bz/59B

Watch the Video: https://ftb.bz/59V

Join the Feel the Boot Founders Alliance https://ftb.bz/alliance

Subscribe to Boot Prints and access to free office hours: https://ftb.bz/join

 

Contents:

Why do we code first and talk later?

What do you need to ask customers?

1-What is the size of the pain point?

2-What priority is this problem?

3-What features do they need?

4-What are the alternatives?

5-What are their implementation concerns?

6-How do they think about price and value for this?

7-What messaging resonates with them?

Getting to statistical significance

Don't let customers lead you around by the wallet

Who should you be talking to?

Considerations for marketplace businesses

Get it mostly right before starting to build

Shut up and take my money!

30 Jul 202158. How I learned to master complex B2B sales meetings as an inexperienced startup founder00:18:33

When I started as a founder, I struggled with sales meetings.

My scientific instincts worked against me. I often wanted to prove that I was right and argue my way to a sale. Fortunately, between fantastic coaching and excruciating failures, I eventually turned sales meetings into a personal strength.

I want to share some of my key learnings with you so you can avoid the whole "pain and suffering" part of the process.

 

Read the blog version of this episode: https://ftb.bz/58B

Watch the video: https://ftb.bz/58V

Feel the Boot Founders Alliance: https://ftb.bz/alliance

Join Feel the Boot: https://ftb.bz/join

14 Jul 202157. Startup Lifecycles and Surviving No Man’s Land – Ruth King Interview00:35:21

Profitability Master Ruth King is the award-winning author of 5 books including “the Courage to be Profitable” and “Profit or Wealth?”  In this interview, we talked about the lifecycle of startups and particularly the challenges of a phase encountered by most companies that she calls “No Man’s Land.”

 

Some of the specific topics we covered were:

·      When to listen to friends encouraging you to start a company

·      Talking to potential customers

·      Characterizing your users

·      Setting the right price

·      Managing through No Man’s Land

·      Transitioning from working in to working on your business

·      Building an emergency fund to survive the inevitable crises

 

Links

Feel the Boot “Boot Prints” signup: https://ftb.bz/join

Founder’s Alliance: https://ftb.bz/alliance

Blog with transcript: https://ftb.bz/57B

Video of interview: https://ftb.bz/57V

 

Recommended books:

The Miracle Manager https://amzn.to/3ATK0Gy

The Courage to be Profitable https://amzn.to/3ecnxdX

Profit or Wealth? https://amzn.to/3kb0N1K

 

About our guest, Ruth King

Profitability Master Ruth King has a passion for helping businesses get and stay profitable utilizing the latest systems/processes/technology.  

 

After twelve years on the road, doing 200 flights per year, she knew there had to be a better way to reach business people who wanted to build their businesses and train their employees. She began training on the Internet in 1998 and began the first television like broadcasting in 2002. Her channels include www.hvacchannel.tv,  www.profitabilityrevolution.com and others.

 

Ruth holds an MBA in Finance from Georgia State University and Bachelor's and Master's Degrees in Chemical Engineering from Tufts University and the University of Pennsylvania, respectively. 

 

Her latest book, Profit or Wealth? reached #1 in October, 2020.  This book is preceded by The Ugly Truth about Cash and the #1 best-selling book, The Courage to be Profitable.  These two books were named two of 37 books start ups should read, along with the books of Napoleon Hill, Stephen Covey, Dale Carnegie and other esteemed authors.  She is also the author of two other award winning books, The Ugly Truth about Small Business and The Ugly Truth about Managing People. 

07 Jun 202156. Bootstrapping vs. VC funding: which is right for your startup?00:20:57

Should you bootstrap your startup to greatness or take outside investment to accelerate your growth? Making the right decision can determine if your company will succeed and change your payout at exit by orders of magnitude.

 

Read the blog at https://ftb.bz/56B

Watch the Video https://ftb.bz/55V

Join Feel the Boot for our newsletter and free personal coaching https://ftb.bz/join

Meet other founders in the Feel the Boot Founders Alliance group https://ftb.bz/alliance

 

When is venture capital clearly the correct choice?

When is bootstrapping clearly the correct choice?

Implications for dilution

What if you have a modest exit?

Managerial independence

Resources

Resiliency

Relationships

VC vs. Angel investors

Bootstrapping vs. VC is not a binary choice

Other options for funding

03 May 202155. Create a pitch deck that investors can read in seconds, because that may be all you get00:16:48

Founders are often frustrated that, after struggling for weeks to perfect their pitch deck, investors just skim through it in a few seconds. Unfortunately, because they look at so many companies, they don't have a choice. I recently attended a webinar by Eric Bahn, GP and co-founder at Hustle Fund, where he talked about using better slide headlines to create a skimmable deck. His approach resonated with me, but I also had some additional thoughts on the topic. So, with his permission, I wrote this article to comment on and expand upon his concept.

I created some example slides to demonstrate this concept. Take a look at the blog to see them https://ftb.bz/55B

Eric suggests that the slide headlines should contain most of the vital information in the presentation. The contents of the slides only serve to support and amplify the titles. He advocates making the headlines complete sentences so that they can stand on their own. Furthermore, when read in order, they should create a comprehensible paragraph explaining the key aspects of the company and opportunity.

This approach also has the advantage of helping you organize your slides. For readers to follow your message, presentations must flow logically and smoothly from topic to topic. Using complete sentences as headlines makes it obvious when your deck has a problem. Logical progression failures often happen when a deck goes through many rounds of revisions. A slide that made sense in its original position now does not follow from the previous ones. Reading through the headlines can quickly show you where you need to make changes.

I encourage you to check out Eric's webinar. In addition to the presentation, he has extensive Q&A with the audience that helps explain the concept in more detail.

 

Eric Bahn’s webinar https://youtu.be/z7icuhqPq5s

Blog version of this episode: https://ftb.bz/55B

Video version https://ftb.bz/55V

Founders Alliance https://ftb.bz/alliance

Join Feel the Boot https://ftb.bz/join

23 Apr 202154. What projects to prioritize, and which you should kill, in your startup00:14:32

Today I want to address a problem faced by many founders, prioritizing development projects in the face of conflicting opinions and pressures. Because resources are usually critically limited, you must narrowly focus your development resources. What are you going to build, and more importantly, what will not get built? The problem compounds when you are a non-technical founder/CEO, and your CTO, developers, investors, or others are pushing to prioritize specific projects about which you have doubts.

 

Join Feel the Boot for office hours https://ftb.bz/join

Feel the Boot Founders Alliance https://ftb.bz/alliance

Blog Version https://ftb.bz/54B

YouTube Version https://ftb.bz/54V

Podcast https://ftb.bz/podcast

 

0:00 Introduction

2:54 What Not to Build

10:08 What to Build

 

I recently advised two founders in this situation. One was pressured by their CTO and the other by a potential angel investor. In both cases, they wanted to re-implement third-party code they had licensed and which was performing adequately. These applications were core to their business but fairly commonplace with the same basic functionality available from multiple vendors. Writing their own version would be a significant undertaking.

It can be challenging for founders to push back against more technical team members because they hired them for precisely those missing skills.

The trick is to avoid having a technical debate. Reframe the discussion in terms of business needs and priorities. Start the discussion by looking at your options in the context of the company’s limited development resources. It is usually a zero-sum situation where every effort displaces something else. Typically, there are many projects on the roadmap which are absolutely essential to your growth.

09 Apr 202153. Virtual Pitching and Fundraising Over Zoom, What Founders Need to Know00:24:45

At one time, almost all startup fundraising happened in person. Investors wanted to see the founders face-to-face to get a read on their passion, intensity, and integrity. With COVID, all that changed, and the industry quickly pivoted to conduct virtually all pitching and investing over video conferences, mostly Zoom. I don’t think we will ever go back to pitching entirely in person, so mastering remote fundraising is critical.

A comment by Munly Leong on an earlier video prompted me to create this episode. He asked how he could find angels and VCs making investments using 100% virtual and remote processes. Before addressing the general advantages, disadvantages, and key tips for virtual pitching, I address his question specifically.

0:00 How Virtual Pitching Changes Startup Fundraising

2:36 Finding people willing to invest 100% virtually

5:16 Finding investors for companies outside North America and Europe

8:55 Upsides and downsides to virtual fundraising

10:43 Pre-screening matters more

12:37 The pitch is everything

13:51 Present, Converse, Demo

16:29 Improve your A/V setup

19:37 Watch your audience

24:27 Virtual pitching not so different

 

I would love to hear about your experiences with online fundraising. Please let me know what you have seen, or any great stories, in the comments below.

Till next time, Caio!

 

Resources

Websites with Lists of angel investment groups and seed funds

https://www.angelcapitalassociation.org/

https://angel.co

https://signal.nfx.com/

https://crunchbase.com

 

Referenced Episodes

Why you need Two Pitch Decks: https://ftb.bz/5B

Five Step Pitch Deck Process: https://ftb.bz/33B

Slow Down While Pitching: https://ftb.bz/52B

Why Angels Demand 20X returns: https://ftb.bz/3B

Build a strong foundation by testing assumptions first: https://ftb.bz/21B

31 Mar 202152. Slow down and say less to communicate more when pitching startup investors00:07:57

I judged a pitch competition last night and the other judges and I, all noticed something about most of the pitches. They were going way too fast. The founders were just tearing through the material and leaving us baffled about what it was they were talking about. So I was inspired to create a quick episode talking about this issue, unpacking why it happens so often, and some ways to try to avoid the problem yourself

Read the whole blog here: https://ftb.bz/52B

Watch the video: https://ftb.bz/52V

Join Feel the Boot free for access to my office hours: https://ftb.bz/join

It is not hard to guess why the founders were going so fast through their material. They only had three minutes to pitch their company, and so much they wanted to say about it. They felt that they had to rush to get through all of the things they thought we'd need to hear. And therein lies the problem. The presentations ended up being like a fire hose of completely undifferentiated words.

So, the paradox is that you need to say a lot less. And the less time you have, the more rigorous you need to be about what you cut out. There is no way that you're going to say everything significant about your company. It's just, it's not possible. You're going to need to pick and choose.

So say less, really edit down the information. Even if you know you need to provide a piece of information, you may be able to go through it quickly. Some points will only take a couple of seconds, then pause for it to be received, then move on. And the pause matters. Let things sink in. When I listened to the pitches, my inability to understand the key elements of their business was driving me insane. They spent two seconds on one topic, and as I was trying to work out what they meant, they were on to talking about the next topic. Because I was still thinking about the previous point that I thought might be important, now I've missed the following two things, and I'm trying to scramble to keep up. Not good.

So take a breath, slow it down. It was funny to read the chat window during the pitch competition. The founders were talking to each other about how they were getting out of breath. They literally forgot to take breaths, and it showed. The key here is just to own your time, which also exudes confidence. If you slow down what you're saying, you're master of your space and time. You show that you know the points you want to make. You're not just trying to fill the time available, but rather convey exactly and only the information that you want to share. You pause to allow them to understand that, and then you move on. It shows that you are in control of the situation.

We know that investors make a lot of their decisions based on the CEO. To a great extent, the job of a CEO is to communicate. Demonstrating that you're a strong communicator is essential.

All this is a very long way of saying, "In your pitch, take your time, slow down, say less."

Till next time, ciao

12 Mar 202151. What founders need to know about patents and intellectual property for startups - Adam Philipp00:49:53

What are trademarks, patents, copyrights, and trade secrets, and how should you use them in your startup? Investors frequently pepper startups with questions about their intellectual property and how well it is protected. Most founders know very little about this somewhat arcane and complex topic. Fortunately, with a bit of information, you can start making the right decisions for your business and speaking intelligently about the issue with angels and VCs.

I brought in Adam Philipp to get you up to speed on the basics and some initial strategies. Adam is the founder of the IP law firm AEON Law, a patent attorney, and has been practicing IP law for over 25 years.

If you have any questions or would like us to go deeper on some topic, please let me know in the comments. I am sure Adam would be happy to come back for another episode. You can find Adam’s law firm at aeonlaw.com and follow him on LinkedIn at https://www.linkedin.com/in/adamphilipp/ and @AdamPhilipp on ClubHouse where he can be found offering the occasional “Patents and IP Law AMA.”

 

Read the blog version: https://ftb.bz/51B

Watch the interview: https://ftb.bz/51V

Join Feel the Boot: https://ftb.bz/join

Check out our community of founders: https://ftb.bz/alliance

In this interview we covered:

1:37 What is intellectual property?

5:08 What should founders do early on to protect their intellectual property?

10:05 What are the elements of a patent?

14:22 How can a founder talk safely to investors without an NDA?

19:54 When should you file your patents?

24:27 Which provisional patents are worth converting to full patents?

27:32 How do you enforce patents?

34:30 How should startups use copyright?

42:10 Patents vs. Trade Secrets

26 Feb 202150. Bad startup advice creates cargo cult thinking. Learn to spot and avoid it.00:12:11

I am concerned about a lot of the startup advice I see out on the internet. Much of the advice is sound, and almost all is well-intentioned, but I think that a significant fraction is problematic. The troubling advice is typically in the form of a recipe or template for success. It tells founders that if they take specific actions, follow a given pattern, or use a particular pitch deck, they will succeed. I often see this guidance in interviews with extremely successful founders. The implication is that if you do the same things they did, you will have a similar outcome.

I worry that these kinds of guidance are too rigid and replace thinking with mimicking. Startups are not like snowflakes; they are far more diverse. Tips that apply to one company may be inappropriate or harmful to another. I suspect that this kind of advice often leads founders into cargo cult thinking. Since many of you might be unfamiliar with cargo cults, I will take a quick detour to explain them before discussing how the concept applies to startups.

Read this as a blog: https://ftb.bz/50B

Watch the Video: https://ftb.bz/50V

Listen to the Podcast: https://ftb.bz/podcast

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Join Feel the Boot: https://ftb.bz/join

The 5 step pitch deck process is here: https://ftb.bz/33B

16 Feb 202149. Six reasons to delay automating processes in your startup as long as possible00:11:02

I have talked to many founders about automating business processes and why they should put that off as long as possible. You may have heard the Y Combinator mantra “do things that don’t scale.” Usually, they discuss that in terms of sales or support, but we rarely talk about the idea with respect to software and automation. We need to understand the value of doing things by hand in the early stages of a business.

 

In this episode, I explore the kinds of automation you may want to defer with some specific examples. I then share the six primary ways that performing these processes manually, in the beginning, can provide value to the business and avoid unnecessary costs.

 

Read this as a blog: https://ftb.bz/49B

Listen to the podcast: https://ftb.bz/podcast

Watch it on YouTube: https://ftb.bz/49V

 

Get exclusive FTB content and member-only office-hours by joining free on our website: https://ftb.bz/join

Join us at the FTB Founder’s Alliance: https://ftb.bz/alliance

 

 

Founders often have a strong bias towards action. When you see that some process will eventually need to be automated, you may want to do it immediately. In most cases, I suggest that you hold off and go with “mantomation” at first. Mantomation is what I call it when you fake your automation using people.

 

Users want results. They don’t care if some sophisticated software is doing the magic or a box of hard-working hamsters. It is the result that counts, and it does not matter if they need to “Pay no attention to the man behind the curtain.”

 

I am not suggesting that automation is bad or that you should not do it at all. In my examples, the companies all eventually make heavy use of software processes. My advice is to wait until the last possible moment before you start that development. When the manual approach is strained to the limit, and you have squeezed all possible information from working directly with the data and customers, then start automating.

29 Jan 202148. Who is Lance, and why is he talking about startups?00:09:05

I don't introduce myself in these blogs or episodes, which may leave some of you wondering, "Who is this Lance person, and why in the world should I take his advice on startups?" I thought So, that’s the topic for today.

TLDR:

I have been an entrepreneur where I ran my own business for 13 years.

I then stayed on as Chief scientist for the acquiring company, where I helped develop their technology, delivered sales presentations, managed their PR, and ran their marketing department.

Since 2012, I've also been an active angel investor and startup mentor.

Before all that, I was an astrophysicist, so I bring a scientific approach to the startup process.

 

The longer version

I grew up in an academic household where both my parents were professors. One of them was a physicist and the other a sociologist. From the age of six, I planned to follow my father footsteps to becoming a physicist

I went to graduate school at UCSD to study astrophysics. I was working with the Hubble Space Telescope and the Keck, trying to understand the early Universe. In my spare time, I started dabbling around with cryptography, privacy systems, and building anonymous email systems. About the time that started to take off and get exciting, I realized that the Hubble Space Telescope wasn't big enough to answer the questions I was trying to ask. That was getting frustrating, so I put my Ph.D. on hold and founded what became Anonymizer, a company focused on consumer internet anonymity. It allowed people to avoid all tracking on the Web. I grew the business for several years, but we began to hit a plateau around 2000. And, of course, 2000 was an exciting time to be in an unfunded startup. That was when the .COM collapse happened all the fundraising dried up. It was touch and go to survive at all.

After that, there was the 9/11 attack on the Twin Towers and the Pentagon. We, like everyone else, started to wonder what part we could play. We started reaching out to people that we'd met in the government, mostly in the FBI, because they kept subpoenaing us for records on our Anonymous users. We were able to talk to them about how they were conducting online undercover operations, and we pivoted to focus on building covert operational platforms for the national security community. This model was very successful. These had extreme pain points and were willing to pay a lot to have them solved, and we were the only people around doing it.

Between 2001 when we started selling to the government, and 2006 that segment of our business went from about 1% to more than 95 percent of our total revenues. Around that time, we realized we didn't have the background or government connections to take the business where we wanted to go. So we started looking at being acquired by a Beltway Insider, and in 2008 we had an excellent exit to a small systems integrator. The founders of that company were all former Spooks and had the connections, knowledge, and understanding to take the solution where I couldn't. But, being spooks, they weren't going to talk to the media, so I ended up becoming the face of the company that bought mine.

I did all the pr. I did most of the public speaking. I wrote the company blog, and it was my face & voice any time we needed to speak publicly.

After a few years of being the Chief Scientist for this company, I decided I didn't want to live in the DC area anymore, so I moved out to Wine Country in California, where I could telecommute.

That was I started to get involved in Angel Investing. One of the first things I did when I moved out here was join the North Bay angels and get involved in a startup mentoring program. Helping startups became a passion of mine. I discovered that I loved working with and helping these early-stage companies achieve success.

At this point, I don't need more outward trappings of success. I'm enjoying living on a hilltop next to my vineyard with beautiful views and an excellent wine cellar. Now I'm much more interested in giving back to other companies. The great thing about advising is it provides most of the fun of being a Founder without the hundred-hour work weeks and constant existential dread.

Shortly after joining the North Bay Angels, they invited me to be on the board and their selection committee. The committee is the group within the North Bay angels that looks at all of the applicant companies and decides which will present to the entire group. That is a great experience because I get to see so many different pitches. These are not the finely polished best of the best. I see many rough presentations, which helps me know what makes the best of them shine.

A problem with the in-person advising was I could only meet a limited number of companies, and I wanted to help a vastly larger number of Founders. That's why I created Feel the Boot as a platform where instead of doing Just one-on-one advising, I could put this information out on the Web where would be accessible to anyone. Then, if they needed more specific individual coaching, they could seek me out, and I'd be able to do that.

At the beginning of 2020, I walked away from my role as Chief Scientist to focus full-time on advising.

Later in 2020, I joined the Founder Institute. I reached out to them, and they offered to make me a global entrepreneur in residence. That means I'm advising their companies everywhere in the world. One of the great things about this is I talk to many companies with different issues and problems. I am continually learning from the experiences of every founder I help.

The advice I give through Feel the Boot comes from my history as a founder, my experiences as an investor, and learning from one-on-one advising, consulting, and BoD work with founders.

But everything always comes back to my experiences as an academic and a scientist. It shapes the way I think about everything. I am always looking for patterns. Why do startups work the way they work, and how can we understand them at a fundamental level. I want to get founders away from the "cargo cult" approach where they think that if they emulate a pattern, it should work because it worked for someone else. I want to get to the fundamental why and how. Think deeply about what you're doing so that you can take what's unique about your business and put it in the best light, and leverage it in the best possible way.

I question whether this will be useful to anyone, but hopefully, this gives you some idea of where I come from, why I'm passionate about startups, and why the things I say hopefully carry some weight.

Till next time … Ciao.

15 Jan 202147. Ten Common Startup Fundraising Mistakes and How to Avoid Them00:21:30

As a Global Entrepreneur in Residence at the Founder Institute https://fi.co and chair of the selection committee for the North Bay Angels https://www.northbayangels.com/ I see heaps of pitches. Unfortunately, the same few fundraising mistakes doom most of their efforts. I want to share with you my list of the ten most common fundraising mistakes founders make and how you can avoid them.

1 – Only Looking at Equity

Just because you can get angel or VC investment does not mean that you should. Some other sources of growth capital don't require selling part of your business.

2 – Going in Cold

At the North Bay Angels, companies introduced by a member receive funding several times as often as previously unknown startups. You are at a massive disadvantage if your first interaction with an investor is to put your hand out asking for money.

3 – Fundraising too Early

A large fraction of companies applying to the North Bay Angels are not ready for angel investment. Unfortunately, you typically only get one bite at that apple.

4 – Missing the What and Why

I often reach the end of a pitch, having heard all kinds of information but with no idea what the company does or why. I need to be able to picture your business in action and your users interacting with the solution.

5 – Failing to Understand Your Audience

You know your business far too well, or at least I hope you do. You no longer remember what was obvious about your market space and what you learned while working on your business. This leads founders, particularly technical founders, to assume that their audience of investors understands these things too. I assure you that we do not.

6 – Weak Communications

In a perfect world, investors would judge your company solely on the quality of your idea, plan, and execution. Unfortunately, we don't live in that world. Investors are unlikely to see past an ugly surface to the gold within.

7 – Hiding Weaknesses

Many startups have some skeletons in the closet. If it looks like you have been trying to keep these issues hidden, you are violating our trust. And trust is everything in early-stage investing.

8 – Failing to Make Commitments

Often founders are vague about timelines and milestones. I want to know that after this investment, you will release a new version of the product with the following enhancements, grow to some number of customers, and generate a specific amount of revenue. If you can show a history of making and keeping commitments, even better.

9 – Raising too Much (or too Little) Capital

Sometimes funding applications draw an immediate rejection because they are raising too much money or too little.

10 – Failing to Follow-up

Finally, follow-up after your introduction, pitch, and any other interaction. Most investors are busy and easily distracted. If you wait a few days to get back to us or set the next meeting following a pitch, I am likely to have forgotten most of what you said and be off chasing some new shiny object.

Conclusion

Fundraising is hard, time-consuming work. Even if you do everything right, the odds of any angel or VC investing in your company are low. But, if you make these unforced errors, the odds quickly drop to zero. You are taking a huge risk as an entrepreneur. Make sure you give yourself the best possible chance of success.

31 Dec 202046. I picked the wrong year to stop sniffing airplane glue - looking back at 2020 and to our future.00:09:45

In this year-end installment of Feel the Boot, I want to, not surprisingly, look back at 2020 and also talk about some of the ideas I have for where Feel the Boot can go going forward.

When I thought about this episode, the first thing that came to mind was the "I picked the wrong week to stop sniffing glue" scene from Airplane!

For those of you who aren't familiar with that reference, check the Wikipedia article. https://en.wikipedia.org/wiki/Airplane!

A time of transition

This year has been kind of a train wreck for almost all of us, and it made me realize how much privilege I have personally. I know many people who are having a rough time while I'm up here on a mountaintop with a beautiful view, a vineyard, and naturally isolated. Plus, I've been working from home for years, so not that much has changed for me.

The reason I thought about the "Picked the wrong year to quit sniffing airplane glue" is that at the beginning of this year, I chose to leave my job after 24 years. I founded Anonymizer in 1995, eventually exiting through an acquisition. I became the Chief Scientist of the company that acquired mine, which then got reorganized. I ended up doing PR for the company, public speaking, running the marketing department, and helping with sales and technology, all kinds of different jobs and roles. But fundamentally never had to jump off that cliff, as I did when I first started Anonymizer, until January 1 of this year. I decided to leave a job where they treated me very well and paid me well to go full-time with Feel the Boot, helping startups, advising mentoring, and Angel Investing. Of course, that meant I walked away from my entire income stream. Angel Investing is not a short-term returns kind of activity. Also, I don't charge for my advising. So, walking away from my paycheck was scary enough without doing it in a strange year like this. It wasn't just the risk of taking on this new role and focusing on this new kind of activity, but then there was the covid crisis, the pandemic, the lockdowns everything got transformed.

As usual, we had fires. I live up here, north of San Francisco, where the fire seems to come through every year. Fortunately, I didn't get evacuated this year. I got evacuated. In 2017 and 2019, but not in 2020, going against the pattern of things this year. The fires only came within a couple of miles of me, but I was able to wait them out at home. I had to use industrial Quality Air Filters to go outside, but even so, we did better than in some of the previous fire seasons.

New roles

With this new focus on my advising activities, I took on some new roles. One of the things I'm doing now is chairing the selection committee at the North Bay Angels, which means I am in charge of looking at all of the companies applying to get funded and deciding which ones get to go through to present to the group as a whole. It is a severely narrow funnel. We might get 30 applicants in a two-month cycle. The committee will look at maybe 15 of them, with the rest dropped right off the bat. We pick five or six to present to the committee, and the committee then selects two or three to pitch to the whole group in that two-month cycle. That's why I talk so much about fundraising and how competitive it is. Many of the companies we reject are good companies with sound business plans.

One change we made this year is looking at companies from a much wider geographic area because of things like zoom and the fact that people don't need to travel to present to a group. Now it's not a hardship where someone needs to fly out to Sonoma for a chance at funding. They just need to show up for a quick Zoom meeting. Rather than being exclusively Bay Area focused, the North Bay Angels is now looking at applicants from anywhere around the country. The dissolving of geographical borders is a big trend in the investment community right now.

The other activity I have taken on this year is becoming a global entrepreneur in residence for the Founder Institute. With them, I provide advice to the companies in their program anywhere around the world. Founder Institute is a global organization with chapters in 90 countries. I might have office hours with someone in Toronto, and then the next call with someone in London, Sydney, Cape Town, or Hong Kong. These days I open my sessions by guessing whether it's day or night by the light in their room and then asking where they are. It's fascinating to see all the different kinds of businesses they're launching relevant to their specific geographic areas.

I'm finding that this Covid lockdown environment has been a real boon for my ability to engage with the startup community without regard to driving distance. Before this, I would usually have to go down to San Francisco for most activities. That's at least an hour drive in good traffic, and it's rarely good traffic, to attend a meeting for an hour or two and then drive back. So I didn't do that very often. Whereas now that I can just jump on the zoom, I'm going to tons of these kinds of events. They give me exposure to a much greater range of companies in different situations doing different types of things. Those experiences informed many of the videos I created this year.

Most frequent advice of 2020

I don't know if it's something about the plague that we're having, but I've noticed that I seem to be giving two pieces of advice more than I ever remember doing before. The first is about the need to focus on talking about what your business is. More than ever, I'm seeing pitches laser in on some technical aspect of the business, or diving into jargon, and skipping answers to the big picture questions.  Who are you doing this for? Why are you doing it? What is the business? How does this make money? Why do people want to pay for it? I need to understand these big dumb picture items before I can appreciate the subtle aspects of exactly how you're accomplishing what you're doing or what's unique about your technology.

The other theme of my 2020 advising has been narrative. Convincing people that they need to spend more time telling stories. They present a lot of facts, and they've got compelling data, but it's hard to digest it and contextualize it when it's just presented in that raw form. I think most of the companies I'm looking at would do much better if they could tell a story about their customers, the problems they're having, and why engaging with this product will benefit them.

I am not sure why those two are coming up over and over this year, but it's definitely a pattern. I'm curious to see whether that continues into 2021.

Feel the Boot going forward

Speaking of 2021, I think we're going to be doing some reorganizing of the Feel the Boot content. Starting off, I only had a couple of episodes, so the blog format worked well. Now that I have 40+ episodes recorded, and by the end of next year it'll be a lot more, we need to find ways of making this content more accessible. We must ensure that when you come in looking for an answer to a certain kind of question, you can immediately find the episode or the blog or the content that's relevant to what you need to know as opposed to digging through them all in chronological order. So I'm going to be spending more time thinking about how I can curate the information to make it more useful.

I'm also considering creating more of a course like structure. Rather than just having an episode on whatever topic occurred to me after talking to some founder, I could try creating a series on getting started, finding product-market fit, doing experiments, or what have you. The episodes would flow together in a logical way to create a program Founders could go through, for free, to take them from point A to point B. From getting their funding rounds, or not getting their funding rounds and bootstrapping their way up, to eventually reaching whatever level of success they're shooting for.

I also think that it might make sense to start pulling this together into a book, so one of the projects that I'm going to be looking at this year is whether I can take all of this content that I've created and distill it down into a volume which would provide that clear roadmap of progress making it much easier to find or refer back to relevant information when experiencing particular problems as you go through different phases of growth.

Finally, your feedback would be invaluable in helping guide our direction. What kinds of content would you like me to create? How can I, and Feel the Boot, be maximally useful to you as a Founder? What kind of problems are you having? What kind of information or answers are you unable to find in other places? Many other people are writing and blogging on these topics, but you're here for a reason. How can I make this more effective and productive for you? Let me know what you like, what you don't, and how I can improve.

Until next time, next year, ...

Ciao.

04 Dec 202045. Founders, your competition might not be what you think it is00:04:35

Watch the video version here.

Or read the blog here.

I want to talk about a different way of thinking about your competitive environment. It's been resonating with a lot of the people I advise.

I talk with a lot of founders about their competitive environment. Usually, that starts in the context of helping them with their deck. They're often in the process of putting together that all-important competition slide, which shows how they stack up against the other companies in their space. Inevitably, it shows that they're superior and puts them in the upper right quadrant or gives them all the little checkmarks down the grid. But one thought that occurred to me during these discussions was that your competition isn't just the other companies in your space.

Fundamentally, your competition is absolutely everything else in the world with which your customer might need to engage. Although you might be better than their existing solution, they still might not choose to buy your product. So often, I see companies where the competition is Microsoft Excel. They've created a solution targeted at some particular vertical that is far better at solving this problem than Excel, so they think: "well, of course, people are going to want to switch to us. We're going to save them money. We're going to save them time we're going to provide whatever benefits we've got." And those are all true statements. But the problem is, will the customer engage? Just because you're better doesn't mean they're going to buy.

Why won't they buy? In many cases, it's because they have too many other priorities. A company or the purchasing manager only has so many hours in the day. They have a limited budget to start these things. They only have a few people free to work on new projects and finite mental energy to even think through these issues. It's not just a matter of being better than what they're doing. It's a matter of being able to rise above that level of noise and get on the priority stack at all. Of the thousands of things this person could potentially do, they will only act on maybe 10. How do you get to be one of those 10? That is why any other thing they could spend time attention money on is a competitor to you.

When you're thinking about the question "how much do people want my product?" it's not enough to say it will save them money or produce some sort of beneficial outcome. You need to show that this is a big enough problem for your customers to put it at the top of their priority stack. People talk about a solution needing to be much better than the alternatives and addressing a substantial need. It's not because what you're doing isn't better. But if it's not a whole lot better, it will not lose to your direct competition, but rather to the fog of war that's going on all the time and all the other things people need to do.

I'm encouraging the people I advise, and I'm encouraging you, to spend a lot of time talking to potential customers. Understand the problem set, understand what other priorities they're dealing with. Make sure before you invest time and treasure into your own business that you meet the threshold where people will put you above the set of priorities that they were previously considering.

I would appreciate your feedback on this shorter and more casual blog/episode format. Please leave a comment down below to let me know whether you like these shorter episodes or whether you'd like me to stick with longer, more formal episodes that I've been doing in the past.

Until next time ... Ciao!

20 Nov 202044. Che Voigt - Feel the Boot Interview pt. 200:47:11

I first interviewed Che Voigt a few months ago. He is chair of the North Bay Angels and co-founder and CEO of Altwork.

If you have not already listened to that episode, you can get it here: https://ftb.bz/32B

At that time he was getting ready to release a new version of his product right in the middle of the COVID crisis. Little did we know that all his plans were about to change. Shortly before the launch, Black Lives Matter protests broke out all over the country. Out of respect to that situation, Che had to radically alter his approach. We started this interview by looking at how he adapted to that rapidly changing situation. We also talked at length about raising angel or venture capital, when it makes sense, what kinds of companies are suitable for it, and how the fundraising climate has evolved.

Che has thought long and deeply about all aspects of the startup process and shares many of his profound insights in this interview. Enjoy!

06 Nov 202043. Sales Aren’t My Thing: How To Reframe Your Perspective and Close Multi-Million Dollar Deals00:23:01

When I founded Anonymizer, I struggled with selling and marketing our solutions. I want to talk about how I overcame my engineering and science habits and prejudices to become effective at sales and marketing.

 

Selling does not come naturally to most technical people. From a cultural perspective, we see it as a “bad thing.” Engineers typically dislike being sold and don’t want to sell. It is a bad word. However, selling is a core responsibility of any founder. You need to do it all the time, in many contexts, and do it well if you want to be successful.

 

I want to help you by sharing a mental framework for approaching sales and marketing that worked for my technical/scientific brain. It worked well enough that after Ntrepid acquired Anonymizer, even though I was chief scientist, they had the marketing department report to me.

Watch this as a video https://ftb.bz/43V

Read the whole blog: https://ftb.bz/43B

Join your fellow founders over at the Founders Alliance group on Facebook https://ftb.bz/alliance

16 Oct 202042. Johann Moonesinghe - Feel the Boot Interview00:46:53

I recently talked to serial entrepreneur Johann Moonesinghe about his experiences as a founder and investor. He was one of the first people in the country to try equity crowdfunding, focused on restaurants.

He actively invests in and advises tech startups through TechStars and directly.

We talked about how the COVID crisis impacted restaurants and other startups, and the common elements among those that are surviving.

He shared his experience as a gay minority founder and the importance of mutual community support.

Finally, we dove into his process in choosing what companies he wants to invest in and his advice to new entrepreneurs.


Get the podcast here https://ftb.bz/podcast


Johann recommended:

StartOut Growth Lab - LGBTQ+ focused accelerator https://startout.org/growth-lab/

TechStars Accelerator https://TechStars.com

LinkedIn (don’t forget the obvious tools) https://LinkedIn.com


02 Oct 202041. Joy Hermsen - Feel the Boot Interview00:49:06

In my recent interview with Joy Hermsen, we talked about a wide variety of issues and ideas critical to entrepreneurs, including finding mentors, startup survival strategies, how training for triathlons relates to entrepreneurship, and getting or giving frank feedback.

Joy’s experience in business and from teaching entrepreneurship and leadership shines through in this conversation.

Bio:

Joy Hermsen is an educator, connector and strategist who loves to help aspiring doers do. Of all the roles she has had over the years, teaching Entrepreneurship and Leadership is her favorite, allowing her to draw on her experiences as a founder, intrapreneur and “Chief Activator” in organizations large and small. As Statewide Director of Retail/Hospitality/Tourism for Economic/Workforce Development at the CA Community Colleges, she connects industry to students and campuses across the state. By asking direct questions such as “Why not?” and “What are you waiting for?” Joy has managed to annoy some and inspire most.

Links:

Blog https://ftb.bz/41B

Podcast https://ftb.bz/podcast

Website https://FeelTheBoot.com

Feel the Boot Founder’s Alliance https://ftb.bz/alliance

Joy’s recommended resources:

Sacramento Entrepreneurship Academy https://www.sealink.org/

Marketplace https://www.marketplace.org/

Kaufman Foundation https://www.kauffman.org/

18 Sep 202040. How to make luck and exploit hidden business opportunities00:14:39

Intelligence, skill, and hard work are necessary for your startup to succeed, but they are often not enough. In my experience, you need to be lucky too. In this blog, I will share some of my experiences with creating luck and opportunity to help you make and exploit them yourself.

The corpses of companies with good ideas and execution litter the entrepreneurial landscape. I know that many of my competitors were at least as smart and tireless as me. I also know just how many times luck played a pivotal role in our survival. We had many “by the skin of our teeth” escapes and miraculous opportunities that dropped in our laps. Some of these are “only over a beer” stories. But, I will tell you a few that will illustrate how you can take control of your luck to a degree. Let’s talk about how you can make your luck and exploit it when it happens.

Watch the video: https://ftb.bz/40V

Read the blog: https://ftb.bz/40B

04 Sep 202039. Michele Chaboudy - Feel the Boot Interview00:38:40

I recently had the chance to talk with Michele Chaboudy.

She is an experienced senior executive, serial entrepreneur, consultant, and angel investor.

Michele is vice-chair of the north bay angels and teaches innovation at Santa Rosa Junior College.

Her background and experience are wildly diverse giving her insights broad applicability.

In this interview, she shares tons of useful advice for any founder or CEO.


In the course of our conversation, we talked about:

how many young entrepreneurs misunderstand networking. It is not handing out business cards over drinks and hors d'oeuvres. It can happen every day, all the time.

her favorite analogy, taken from her experience racing motorcycles. You need to be looking at least two turns ahead because you go where you look.

her process for evaluation companies as an investor, and what matters most to her.

how she teaches founders to develop a strategic mindset

what entrepreneurs need to know about researching their intended customers


Feel the Boot Founder’s Alliance: https://ftb.bz/alliance


Michele’s startup consulting website: https://macabbey.com/blog


Michele’s suggested resources for founders and entrepreneurs:

https://helloalice.org---co founded by Elizabeth Gore, who was also interviewed on Feel the Boot.

Simon Sinek— https://simonsinek.com/ particularly his “Start with Why” (book) and any of his speeches.

Scott Berkun— https://scottberkun.com/ - “Dance of the Possible” book and “Saving My Creative Soul” (video). All of his books and talks are excellent.

Malcolm Gladwell, recommend all of his books including his latest, Talking to Strangers.

Tina Seelig— http://www.tinaseelig.com/ - Stanford prof in engineering dept teaching innovation. Favorite book: Ingenius. Recommend any of her books and Ted Talks.

Jason Calacanis— https://thisweekinstartups.com/ Interviews Start-up Founders/CEO’s. Recommend his book on angel investing for tech start-ups.

Range by David Epstein. Why Generalists Triumph in a Specialized World. —The worst thing you can do is ask a kid what he or she wants to be when they grow up. Try to keep all your options open and don’t worry about starting “late” in a pursuit.

Lean Impact—How to innovate for radically greater social good by Ann Mei Chang. Takes the Lean Start-up concept and applies it to non-profits.


21 Aug 202038. Identify the one strength you must emphasize in your fundraising pitch with four startup case studies00:13:34

When you pitch investors, your audience will only remember a couple of ideas. Your job is to make sure they are your biggest strengths. In this blog, I will help you identify the aspects of your company that will wow investors.

I talked in previous blogs about why you need to highlight the most important strengths of your business in any presentation, particularly in pitches. If you need help creating the pitch, check out my complete pitch building process, check out this blog.

How do you decide which aspects of your startup will be the most important to this audience of potential investors? First, you need to get inside their heads. Try to understand what about your business will impress them. If you have not watched it, it might help to go back and revisit my blog on the nine things angels want to see in an investment pitch

I think that some real-world examples might be the most effective way to illustrate the kind of strengths that impress investors. In this blog, I will consider four companies I know well and the characteristics that made them stand out to me.

One thing that may surprise you is that none of these are about the technology or cool solution itself. Obviously, the solution needs to be valuable and desired, but there are a lot of companies that meet that standard. Most often, the startup’s best aspect is something outstanding about the company or business model.

One – Pet wearables platform

If you follow our interviews, you may already know the company I am talking about. They make a smart modular pet collar with an associated smartphone app. The app has a marketplace and supports other kinds of third-party integrations.

While they have gone through a few pivots, both in their products and in their messaging. I think they have nailed their key ideas.

This is a Platform, not a Product

The marketplace for smart pet devices is crowded, and many of them are having difficulty standing out. The company avoids that problem by positioning itself as a platform. They integrate deeply into the whole pet ecosystem and the lives of the owners.

The platform also provides multiple potential streams of revenue and partners that can act as sales channels: pet food, toys, medicine, vets, groomers, walkers, boarding, training, and many more. Also, the integrated platform is more sticky than a simple device. Switching to a different collar would disrupt many other relationships.

Additionally, they have active contracts with partners that are paying the company to develop integrations and are committing to help with marketing. They are in mature discussions with several more possible partners with different offerings.

This shows people that the idea is not some fantasy, but is real and works.

What I remember from their pitch: a platform, not just a device, with proven traction.

Two – Virtual group sports watching

This company created an app that allowed friends from college to continue to watch sports together virtually even after they scattered to the corners of the globe.

This company is inherently viral

You can’t watch sports with friends by yourself (obviously). Users have to recruit their friends to the platform. Because we don’t all have the same friends, that person would invite a different set of friends for other events. This exponential growth would expand the userbase automatically.

The company only needed strong execution to generate the effect. The company was inherently viral.

In addition to growth, the network effects in the business could exclude latecomers to the market. Once all your friends are on a platform, you don’t want to try to get them to move to a new one. If even one of your friends does not want to switch, the group will default back to the original one.

The pitch focused on the inherent virality of the business and how it created both growth and defense.

Three - Medical devices

I have seen several medical device companies that share the same strength. This is not a problem. Highlight your real strengths rather than something unique but less impactful. Their solutions were all very different, but their strengths happened to be the same.

This team will win

These companies all had effective products, solving big problems, in large markets. But that was not the grabber. What made them a compelling investment was the team.

The founders had worked together on previous successful medical startups. They have a track record of success. They know the space, the opportunities, and the traps. They already have relationships with manufacturers, doctors, insurers, the FDA, and so forth. They can talk about precisely and confidently about how they will bring the solution to market.

With a team like that, there are few unknowns and a high probability of success. That is music to the ears of an investor.

All the companies made a point of focusing on the obligatory team slide.

Four – Water-saving next-generation irrigation

This company developed an innovative lawn irrigation technology that saves water and reduces installation labor costs. They are reaching their market through landscaping companies who sell and install the systems for end consumers or institutions.

A Win-Win-Win alignment of interests

The key idea, and what pushed me over the line to become an investor, was how the company ensures that all parties are highly motivated.

The landscapers love it because installing this system takes a fraction of the time/labor as a conventional one, while the hardware costs are comparable. But, they charge the same price, so their profits go way up.

The customers love it because, for the same price, they save a ton of money on water. They also feel good about helping to conserve a scarce resource.

Recruiting new landscaping contractors is easy, and each one then drives new sales. Win, Win, Win.

Some companies have a murky path to market. Their deck made it crystal clear why this would get traction and take off.

Of course, there is much more to say about each of these businesses. All of their pitches hit all the required points. At the end of the presentations, I felt comfortable with the companies. They had addressed all my concerns. But, beyond that general feeling, the things I still remembered days later were these key points, which was the point. If you can identify and emphasize the best aspects of your business, as they did, you will have a big leg up on most of your competition.

The same concept applies to marketing, just with different points. Your customers won’t care about the same things that motivate investors. The smart collar company does not talk about platforms in its advertising; it talks about protecting the health and safety of fur-babies. The medical device companies talk about the health and cost benefits of their solutions. The irrigation company talks about improved profits and sales to landscapers and about saving money, saving water, and saving the planet to the customers.

Hopefully, those examples will be helpful with finding your key strengths. Many founders have a hard time with this exercise because they are too close to the business. They understand all the details and subtleties and may think the big picture is too obvious to state. If you are having trouble, find an outside advisor or peer to help you get the perspective you need.

Let me know if this helped clarify how to find those key strengths or whether I need to take another crack at it. I would love to hear about the aspects you identified either in the comments or over in the Founders Alliance group.

07 Aug 202037. Lisa Tamayo - Feel the Boot Interview00:50:18

I recently had a chance to interview Lisa Tamayo, serial entrepreneur, angel investor, CEO/Co-founder of Scollar, and my close friend.

We talked about their pivot from product to platform, and she shared hard-won experience about the startup process that will be invaluable to any new founder.

Video: https://ftb.bz/37V

Blog: https://ftb.bz/37V

31 Jul 202036. A tool for choosing the best business direction and strategy for your startup. Part 200:11:34

This is the second video exploring a process I developed for helping you find the optimum direction and strategy for your business. In part 1, you captured a wide range of possible concepts, then systematically narrowed them down to just the best few. If you have not already read it, I suggest you go back to part 1 before reading this. https://ftb.bz/35V

In this part, you will dig deeper into your best business ideas to crown an eventual winner.

You can also read this as a blog. Part one at https://ftb.bz/35B or this part at https://ftb.bz/36B

Digging deeper on your top options:

You narrowed your options down to just a few top options using a quick process based mainly on your experience and intuition. Now you can spend some time exploring only the best strategies in more detail. The fundamental question is, can you win with any of these business directions?

Read as a blog: https://ftb.bz/36B

Watch as a video: https://ftb.bz/36V

24 Jul 202035. A tool for choosing the best business direction and strategy for your startup. Part 100:14:56

If you need to choose a problem to solve, identify their customers, and settle on the solution for your startup to bring to market, this video is for you.

This tool can also be useful for thinking about your pivot options if your current direction is failing.

You can read this as a blog at https://ftb.bz/35B

This video explains the first part of the process where you develop a large number of possible business directions, then systematically narrow it down to a few best candidates. In part 2, you will learn how to drill down and analyze those finalists to pick the one business model most likely to succeed.

Download the worksheet for this process here: https://ftb.bz/35-business-plan-worksheet

As you work through this process, you will uncover your optimum business direction.

For each potential path, you will consider the following criteria:

· What is the need, pain, or unfulfilled desire?

· Who needs that, and how would they use it?

· How many people fit that description, and how urgent is their need?

· Your proposed solution

· Why that solution is better than competitors, alternatives, or workarounds

You should be able to do this initial exercise in a day. After that, you will need to do some more research and conduct tests to see if your guesses and assumptions are right. Using this worksheet is a navel-gazing activity, but you can’t navel-gaze all the way to your final destination.

One thing I did not include in the worksheet is your passion. Because startups are all-consuming, make sure whatever direction you consider is something you would love to spend all your time doing for a long time. Don’t write down an option if you are not willing to do that thing at maximum intensity for years.

Digging deeper on your top options

Part 2 of this video covers how to look more closely at your top contenders and pick the one strategy you want to pursue for your business.

A work in progress

I am using this tool with some of my portfolio companies, but it is not as mature as most of my other advice and methodologies. If you try it, please give me feedback about what worked and what you think needs to be adjusted. Thanks!

10 Jul 202034. Iris Fujiura - Feel the Boot interview00:28:27

I recently had a chance to talk with Iris Fujiura, Chapter Lead of the Silicon Valley chapter of Golden Seeds, a national network of angel investment groups focused on woman-run startups. Prior to that, she was an engineer, and eventually an executive, working on rockets and launch systems.

Video version: https://ftb.bz/34V

Blog version: https://ftb.bz/34B

She provided great insight into angel investor priorities, and what makes for a successful funding pitch. We also discussed the particular challenges facing female entrepreneurs.
Iris recommended the Female Founders Alliance https://femalefounders.org/ as a particularly useful resource.

18 Jun 202033. Five step process to create a killer pitch deck for your startup00:22:55

I answer more questions and provide more coaching about investor pitches than anything else. Once you decide that you need investment to grow your company, your task as a founder is to convince investors to give it to you. The first step in that process is a pitch, and getting it right is essential to the future of your business. In this blog, I will share with you my five-step process for building a killer pitch.

Read the blog: https://ftb.bz/33B

Watch the video: https://ftb.bz/33V

These steps are a process, not a recipe. I don’t have template slides where you just fill in the blanks because we are not playing Mad Libs. Your pitch needs to be unique and crafted to highlight your company’s strengths and relative advantages.

As you create your deck consider its purpose and your objective. It exists to get you the next meeting, nothing more. If you generate enough interest and excitement to move forward with due diligence, you have succeeded.

The five steps are:

· Gather – capture all the information investors might want to learn

· Focus – Zero in on the key elements

· Organize – Layout the flow of your presentation

· Build – Create the actual slides

· Polish – Refine your presentation until it sings

Gather

Start by pulling together all the information that your deck will probably require.

Jot down your answer to each of the following questions. Some may require time, research, and analysis to answer well. Here is a link to a worksheet with all five steps and these questions: https://ftb.bz/pitchdeck-worksheet

1. What is the business?

a. What problem are you solving?

b. How are you solving it?

2. How will you grow

a. Go to market plan

3. What is special about it?

a. Any secret sauce, unfair advantage, etc.

4. Why is this defensible?

a. Moat, defensible IP, network effects, etc.

5. Who is the customer?

a. Why do they need the problem solved?

6. Competition

a. Why much better?

b. Why not just use an existing solution?

7. Business model

a. How do you make money?

b. If not now, eventually.

c. Key economics

8. Financial projections & roadmap

a. Can you survive?

b. When do you need more investment?

9. Why now?

a. Market trends?

b. New technologies?

c. New opportunities?

d. New problems?

10. Why this team?

a. If there are gaps, own it and answer how you will fill them.

11. Current status

a. What have you accomplished so far?

b. What exists, and at what level of maturity?

c. Customers and traction?

12. What is the deal?

a. Amount

b. Structure – equity, note, SAFE, etc.

c. Valuation if set

d. Terms – discount, interest, preference, etc.

If you don’t have satisfying answers to these questions, you might not be ready to pitch. It would be better to spend time researching, testing, and refining the business rather than pushing forward with developing your deck. With most investors, you only get one bite at the apple. Don’t waste it by going in half-assed.

Focus

Now that you have all the information that might go into your deck, you need to bring some focus to your presentation. Try to highlight what your audience needs to hear, not what you like to talk about. I wrote a blog on the nine things angels want to see in your pitch: https://ftb.bz/31B

Try to keep your explanations at a high level. If the audience wants to know more, they can ask questions or dig deeper in due diligence. Don’t get into the technical details of your product unless it is absolutely required. On the other hand, DO state the obvious. Things about your business or market that are obvious to you may not be to most investors.

Thinking of your business as a whole, and referencing the list you made in step 1, what are the best things about your startup? Do you have any business superpowers? What are your particular strengths or aspects that make you stand out? Make a note of that to ensure you highlight it during the pitch.

Then, look for a few other things about your company that the audience must understand and remember. Limit yourself to just a few. After a few days, most people only retain 3-5 items from a presentation. Choose yours carefully and make them count.

Look for and remove details or trivia that does not need to be in the deck. If the investor does not need to know something to understand your business at a 60,000 ft level, it should go. Every slide, every word, every idea, needs to fight for existence in your pitch. Be brutal in your focus.

Organize

Now you need to pull all those ideas into a coherent structure. A pitch is just a special kind of presentation. For a deeper dive into presentations and presenting in general, check out my hour-long presentation training video: https://ftb.bz/P2V

You won’t be able to get away with creating just one deck. Different contexts require different decks. One size will not fit all. You will frequently need to adjust your deck to fill the amount of time they give you. You should never need to rush or stall to hit your allotted time.

You will also need to customize your deck for each audience. If you are addressing a random group of angel investors, you will need to explain some things that are blindingly obvious to you.

However, if it is a group of industry experts, they might be insulted by that kind of remedial level information but want to see more details of your solution.

Finally, and I have ranted about this in a past blog, create different decks for presenting in-person vs. emailing to be read alone.

I want to make a radical suggestion; resist the urge to start using any kind of presentation software at this point. I use 3X5 cards, mind maps, or sticky notes to organize my presentations.

The key is making it as easy as possible to reorganize your deck. You need to be able to see everything all at once and shuffle it around with zero effort. For simplicity, I will just talk about my process with cards.

Another advantage of jotting just a couple of words on each card is that you can cultivate a Buddhist detachment towards them. You spent no time making them, so it is easy to rip them up and replace or change them. Keep the process as frictionless as possible.

Capture on the cards all the information you decided to keep in the presentation and lay them out in what seems like a reasonable order. Mark the headline and key point cards so you can see if they are getting the emphasis you want.

The first and last things an audience hears will be the most memorable and carry the greatest impact. If you can, put your headline in one or both of those places. I did a blog on nailing the opening of your pitch here: https://ftb.bz/17B

Think about your pitch as a story. Narrative is far more memorable than data, particularly if you invest it with emotion. Is there a way of organizing your presentation so that it tells a story about you or your customers? It could be a story about how you came to found the company or a story about a real or imagined customer. One of my portfolio companies created a children’s picture book to illustrate their product and found it to be incredibly effective in all kinds of contexts. Try to connect all the content in your pitch with a single thread running throughout the presentation.

Next, consider the transitions between each concept. Walk through the cards in order and think about what you will say as you advance through them. Does each one follow logically from the one before? Do they build a narrative? Do you make any statements or claims before showing the supporting information or context to understand them? You may need to change the order, add, or remove cards to make things flow smoothly

Now, start practicing the pitch. Do it right from the cards while everything is still easy to change. Present or read (depending on whether it is a delivered or emailed deck) all the way through, making notes and changes as you go. Continue to feel for those awkward transition points. Look for places where the pace drags. Notice if you are spending too much time on less important things. Check whether the key points stand out and are positioned for maximum impact.

Fix the problems you found, then do it again and again until it feels good.

Build

In many ways, this is the easy part. You know all the slides that will be in the deck, why they are there, and what you will say about them. Now, go create those slides. I usually start by making a blank slide with the tiny bit of text that was on each card.

From there, I start zeroing in on the exact content for the slide, of which there should not be much. Slides must be clean and uncluttered, even for read-alone decks. For delivered presentations, the audience must be able to read it from across the room in a couple of seconds. When someone is reading a slide, they are not hearing what you are saying. Your spoken words carry much more weight than the text on the slide.

In a presentation, slides only exist to support and enhance your words. They need not, and should not, stand alone. Steve Jobs was a master of this. When he introduced the new MacBook Air, he talked about how small it was, not with numbers but by pulling it out of a mailing envelope.

And the computer on an envelope was all you saw on the screen behind him. Focusing on and reinforcing that one concept made it memorable. Every article written on the launch used that example.

If you have enough artistic talent to make the deck look fantastic, great, get to work!

If not, mockup the slides, create rough diagrams, and find appropriate graphics or images. Then hand it off to a designer who can make it look professional. With all the content planned out and prepared, it should not cost much to get it looking fabulous.

Polish

Now is the time to start polishing your pitch to a fine edge. If you will be delivering the pitch verbally, whether in person, video conference, or recording, make sure you know the content inside and out. Don’t memorize the words you will say, but rather the message you want to deliver. Internalize the point and purpose of every slide. A memorized presentation often feel awkward, wooden, and over-rehearsed. The only exception is the opening, which can lead to stumbles, so knowing the first few sentences word for word can help. Practice until you can consistently deliver the pitch, in your improvised words, within the time limit.

Next, get feedback from as many people as you can. Ideally, use people who are not familiar with your company, so they better reflect the mental state of your real audience. Find people who are willing to hurt your feelings. You want them to tell you, in great detail, why your baby is ugly. Embrace the power of frank feedback. For read-alone decks, let them read it without you in the room. For presentation, present just like you would in the real meeting.

Afterward, don’t just ask what they thought about your pitch, pose specific questions.

· Where did they get confused?

· Where did they lose interest?

· Did the pitch make them excited about the business opportunity?

· For a presentation, how was your delivery in terms of energy, eye contact, body language, and vocal tone, and filler words?

· Did the visuals and layout of the slides help with their understanding?

· Ask them to explain your business back to you. Did they understand the key points you wanted them to?

· Watch your audiences for clues as to where they are more interested, dubious, or checked out.

Lather – Rinse – Repeat. Keep improving the deck and showing it to new audiences. This process never stops. No pitch is perfect, you can always find ways to improve it, and your company will be continually evolving, requiring you to adapt your content.

Pitch

Pitching is not your core business, so it seems unfair that your success or failure could depend on something so unrelated.

But it does.

Your pitch needs to be amazing because the competition is intense. I see lots of good companies fail to raise funds because of weak presentations. As hard and wasteful as it can sometimes seem, take the time and invest the effort to make yours sing. You may even find that this process helps clarify your thinking about the business.

If you use this process to build or revise your deck, I would love to take a look. As an incentive, I will give the first ten submissions detailed feedback over a coaching call. Warning, I am one of those people willing to tell you that your baby is ugly, sometimes in gory detail.

12 Jun 202032. Interview with Che Voigt, CEO & Co-Founder of Altwork00:21:02

Recently, I talked to my friend Che Voigt, co-founder and CEO of AltWork and chair of the North Bay Angels.

We discussed their innovative workstation and how COVID is driving a work from home trend that is driving unprecedented growth in their sales. He also described their experiences of working with a supply chain based in China during this crisis.

The launch of their first product immediately went viral, and Che theorized about how their choices impacted that.

Now, they are about to launch a new version of the workstation, so this interview is under embargo until the official announcement. We discussed how they are positioning the new product to achieve similar success.

One of the unknowns in any launch is the news environment at the time.

Launching during COVID would have been complicated enough, but we have had to push back the date of this episode because they delayed the launch in light of the current civil unrest.

At the last moment before the release of this episode Altwork chose to do a soft launch of the new product out of respect to the protests and national discussions around BLM. A lesson that you can never control all the variables.

01 Jun 202031. Nine things angel investors look for in startup fundraising pitches00:11:48

Watch the Video https://ftb.bz/31V

Read the Blog https://ftb.bz/31B

Part of the startup fundraising process is pitching angel investors. But when you are putting together a pitch deck, it would be great to know what that audience wants to see. Rather than simply use my list, I reached out to a bunch of other angel investors to learn what they wanted. All of us wanted to see similar things.

From that, I developed this list of nine things angels want to know before committing to a follow-up meeting or starting due diligence.

Full disclosure: this is what we say we want, but might not reflect how we actually make decisions. Emotions and other subjective factors often weigh heavily in our considerations even though we like to think we are making purely logical choices.

#1 Problem or Need

We want to understand who your customer is and the problem or need your company addresses for them. Frame this as what the customer wants, vs. the idea you have. The problem is all about your customer’s world. Tell us about how much pain the lack of your solution is causing to this marketplace, or how eagerly they desire what you offer. If we are not familiar with this market, it helps if you can show that other thought leaders recognize the magnitude of the need.

#2 Your Solution

Having laid out your customer’s problem, what are you going to do about it?

Describe your solution quickly and clearly. Addresses how your offering solves the problem you described.

Don’t get bogged down in details. If you were pitching me the telegraph, I would want to know what it can do, but would I care much less about how it does it. Implementation and technology details are almost always better left for due diligence. We need to have a general understanding of what your thing is, but not at the level of detail you would use if you were selling it to us.

At the end of this, I should be able to picture your customers using your solution to solve their problems.

#3 Competitive landscape

There is always some kind of competition out there. Somehow, your potential customers are making do without your product right now. Their alternative might not be another startup, but just some widely adopted improvised solution. I often see companies where that alternative is just spreadsheets, which work remarkably well for many things. Convince us that your offering will win in the market.

A lot of competitor comparisons are just a list of features. Unless we are your target customer, we may not know if those are exciting features or not.

Suppose you founded Spaceman Spiff’s Rockets. You might use this chart to show why you are better than Space X or NASA. The problem is, I am not in the market for rockets, so I have no idea if your customers will value those differences. Do they care that Spiff’s rocket has a “freem drive”, whatever that is? Is vertical landing a significant differentiator? Who needs a mertilizer beam, and will they pay more for it?

In contrast, I can see why exploring the galaxy rather than just the near-earth orbits would be a big deal. I can imagine that vaporizing enemies might be desirable to your launch market of supervillains.

Frame your comparisons in terms of why they are better for the customer, not in terms of features. It does not matter that you care about or are proud of them if they don’t motivate your customers.

Show us how your solution is enough better than the incumbent solutions that users will switch. Switching is usually painful, so that is a high hurdle.

#4 Defensibility

Your solution might be better than the competition right now, but how do you stay ahead once they see how awesome your product is and start copying it? Let us know about any barriers to entry that will prevent them from competing? Can you create a moat to protect your business from business marauders?

For example, are there network effects that allow a first mover to grab enough of the market to block later entrants? Do you have some unfair advantage that can’t easily copy?

Does the company have enforceable intellectual property?

Strong intellectual property is much more than just having a patent; it needs to be one that competitors can’t easily circumvent and that you could plausibly enforce against likely infringers. Don’t lean on patents as your primary defense unless you know that they will stand up to scrutiny during due diligence. Otherwise, it makes you look naïve.

#5 Team

Most angels put a lot of weight on the quality of the team. A common saying among startup investors is “bet on the jockey, not the horse.” Unfortunately, team slides are often the worst in a deck. They are just a list of names and photos, sometimes with corresponding companies or roles.

This slide is your chance to sell us on your team. Why is this the group of people that will win, even if you have to pivot a few times first? If you have prior experience in your space, it means that you have intimate knowledge of the needs and complexities of the industry. That is important, tell us about it. Also, highlight any team members that have a track record of success in leadership positions in other startups.

Highlight all your team’s outstanding skills: technical, human, leadership, and communications.

Some things about the team can be an explicit part of your pitch, but others will only come out in interactions and conversations. We are observing and judging your listening skills, coachability, and humility as we interact. Coachability matters a lot to most of us because we want to stay involved in helping you.

Through your presentation style, angels want to see that you exhibit focus, high energy, and enthusiasm for your company while being flexible and adaptable in the face of challenges.

In your deck, your presentation style, and all other interaction, make sure these qualities shine through.

#6 Business Plan

We need to see a business plan, but we don’t want a formal MBA style written plan. We need to understand your strategy and tactics for your business to succeed.

How are you going to make money? Maybe not right away but eventually.

How are you going to get into the market? What is your marketing and channel strategy? Avoid just a list of the obvious: social media, keyword ads, word of mouth, pr, etc. Everyone says that. Demonstrate that you have thought about this, have some insight, and maybe have done some tests already. We are looking for any glaring holes or unwarranted assumptions in your plans that would make us say “no.”

Show that the opportunity is big enough for angel and VC investment? In a past blog, I talked about why we need the possibility of at least 20x returns.

When you talk about the size of the market, I want to know about the size of your portion of the market, not the whole thing. If you sell seatbelts, don’t quote me the size of the entire auto industry.

We need to see some financial projections. I also did a blog on how to create appropriate forecasts for early-stage startups. They need to show us your cash requirements and projected future funding rounds. We worry about dilution in later funding rounds if you need a lot more money, and possibly running out of money if those rounds are late. If you say nothing, we will assume the worst.

Finally, do you have a grand strategy for the long term? Where is the company going in several years once you own the initial market?

#7 Progress

What have you achieved so far? Do you have a concept, prototype, MVP, or full product? We need to know what actually exists right now before this funding.

Can you demonstrate customer traction and interest? Do you have sales, paid or un-paid pilots, testimonials, or surveys? Your valuation depends on the maturity of the company and the tangible and intangible assets you have created.

From that starting point, tell us the immediate next steps?

#8 The Deal

You are pitching us because you are looking for investment in your company. Don’t be coy about it. You must be very clear and concise in describing the deal on the table, or honest about the lack of current terms. We need to know:

· How much are you raising in this round?

· What is it that are we buying? Preferred stock, Note, SAFE?

· At what valuation or conversion cap?

· What will this cash be used for?

We want to know how much you have raised in previous rounds, and what you have committed on this one.

If you have any well-respected lead or key investors, be sure to mention it? Investors can be sheep and like to follow a trusted leader.

#9 Exit Strategy

Finally, we need to understand how we will make money on this investment. Typically we get paid when your company is acquired (most often) or goes public (rarely). Therefore we want to know if this an active space for acquisitions. Do you already know of companies that are likely to be interested in you? If so, do you already have strategic relationships with any of them? What are common multiples for acquisitions in the space for companies like yours?

If we get paid in some other way, make that crystal clear. I see this most often in real estate investments where the company makes regular payments starting. Otherwise, non-standard payouts are usually a turn-off. Angel investments are risky enough without introducing unnecessary uncertainty and doubt.

On to due diligence

While it is always possible that any individual investors will have some hot button issue not on this list, if your pitch delivers on all of these nine areas, you have a strong chance of getting that next meeting and potentially getting funding.

24 May 202030. Elizabeth Gore’s Feel the Boot Interview00:26:56

Elizabeth Gore, co-founder and president of Alice (helloalice.com), recently joined me to talk about her entrepreneurial journey and to share some insights with other founders. Alice is a free multi-channel platform powered by AI technology that guides business owners by providing access to funding, networks, and services.

You can also watch this as a video: https://ftb.bz/30V

Before that, she was the entrepreneur in residence at Dell Technologies, served in the Peace Corps, and much more.

We talked about how she became an entrepreneur and how her background contributes to her capabilities as a co-founder.

We discussed why women and minorities are at a massive disadvantage as entrepreneurs, and the particular challenges of being a founder/parent.

Finally, she shared several tips that will be of great help to any small business owner, particularly during the COVID-19 epidemic.

17 May 202029. Escape the busyness trap that tricks entrepreneurs into working hard while accomplishing little00:10:58

Over the last couple of months, I have been incredibly busy with Feel the Boot and other projects. I have been setting up schedules, writing blogs, recording interviews, posting content, advising companies, and the like. All of the associated deadlines have been stacking up, making me feel stressed while not making much progress on my main strategic goals.

Then suddenly, I realized that I had been caught by the busyness trap … again!

You can get this as a video.

Or read the blog on our website here.

The busyness trap is when you get caught in a pattern of doing a lot but accomplishing little. In this installment, I look at: why entrepreneurs are so easily caught in the trap, what it means for your startup, what gets lost when you are in the trap, and some approaches to escaping from it.

Why are entrepreneurs so vulnerable to this trap?

For many, being busy has become a status symbol. When people ask, “how are you?” we say “busy” or even “it’s been crazy.” We brag about long hours, but rarely in the context of any strategic objectives.

Another cause is guilt. I often feel guilty when I am not busy. I will do meaningless little things at my computer rather than walk away. Sometimes I find myself doing completely wasteful activities rather than leave the office. I find myself thinking that there might be a link to a useful article on Twitter if I just scroll down a few more pages.

Stress can often lead to busyness. When you know there is a lot to do, you may focus on doing a lot of things. With no time to look up, you laser in on knocking off that next task, answering that next email, scheduling that next post, or whatever other tasks are on your to-do list, without pausing to think whether those are the most important things to be doing.

For entrepreneurs, busyness is self-imposed. No external boss breaths down your neck, making sure you are filling every moment with productive activity. Although we might have learned the habit from prior employment, we have the power to change that pattern now.

What does busyness mean for your startup?

First, there can be diminishing returns from working longer and harder. Value produced does not scale linearly with hours spent on the job. Productivity drops off sharply after too long on the job.

When I was in graduate school, pursuing a Ph.D. in Astrophysics, I had to take a two-day test covering all aspects of undergraduate and graduate-level physics. For months my life revolved around studying for that test, cramming my head with every possible detail, equation, and technique. I wallpapered my living room in equations big enough to read from the other side of the room to help me have all the information instantly available at any time.

I quickly discovered that I was only good for about three hours per day of focused high-intensity mental effort. Working longer than that accomplished nothing more and left me fatigued. Eventually, I had to give myself permission to structure my days around that reality and do only less brain intensive things outside of those 3 hours.

I need to remind myself that the opposite of busyness is not laziness. It is a purposeful choice about what to do and when.

What gets lost when you get busy?

A lot of important things can get dropped or missed as we get busier. As an example, look at the essential activities that I have been allowing to fall to the wayside.

I don’t read nearly as much as I would like. Reading is fuel for my idea engine. When I am going through a good non-fiction book, I regularly stop to take notes on new ideas and projects.

Busyness prevents me from making time to talk to people outside of structured meetings. Open-ended conversations bring forth all kinds of fantastic concepts and cement relationships that will be valuable later on.

I find it hard to stop and “sharpen my saw” while in the middle of work chaos. It feels like wasted time, even though these meta-activities can lead to substantial overall productivity boosts. Intellectually, I know that improving skills, workflows, and organization structures can all pay big dividends. Yet I stay caught in the demands of the moment.

I feel like I am missing out on opportunities. Being heads down in the weeds can mean that I don’t take time to notice openings or to take advantage of changing situations.

I remember a lesson about relaxation from my Kung-Fu instructor. Tension makes your body slow, while a relaxed body is fast.

The same is true of a relaxed mind that can perceive opportunities for action that would miss when locked into a narrow channel. When you are stressed, opportunity looks like one more thing to do, so you avoid it.

The biggest thing I miss out on is pure thinking time without a specific plan, so my mind can wander over possibilities. I keep a waterproof pad of paper in my shower because of all the thoughts that pop up while engaging in that mindless activity. Long walks, or just sitting staring into a fire, can often be the most effective use of my time, if only I permit myself to do it.

General Eisenhower had an excellent framework for thinking about tasks and making sure that important ones did not get lost in the shuffle. He looked at every activity along two axes.

Whether it was it important and whether it was urgent.

If something is urgent and important, like putting out a grease fire in your kitchen, then there is no question or hesitation. Of course, you do that immediately.

The busyness trap arises from the issues that are urgent but not particularly important. They make a lot of noise and attract attention, but don’t change your world. These are the tasks that often fill our time driving out the others. They need to be kept in check.

We need to make room for the things that are important but aren’t urgent. Reading, thinking, talking, planning, and working on long duration projects all fall into this category. If they are going to happen, we need to carve out substantial time for these kinds of important but not urgent activities.

Finally, there are those tasks that are neither urgent nor important. You don’t need to do those at all.

How do you escape the busyness trap?

Obviously, I haven’t found the magic solution to avoiding the busyness trap. It is a tricky thing because there is no one moment when you feel its jaws grab you; it comes on over time.

For me, awareness of this issue is the first step. Knowing that the trap is a real thing, helps me look for signs that it is happening again.

When you realize that you are spending your time on less important things while strategic initiatives are being ignored, stop and take a breath. Force yourself to take some time to look for ways to eliminate the clutter. I find that an audit of where my time actually goes helps me see where my priorities are out of alignment with my daily practices.

As soon as you realize you are in the trap, spend some time listing the projects and activities that are important to you and make sure you have a process to keep them front and center on your schedule.

Finally, permit yourself to just ponder. Creativity requires that kind of open, unstructured time.

If you are in the midst of the trap, this should help you find your way out, if only for a while.

03 May 202028. How to create financials for early stage pre-seed startups that will wow investors00:12:41

Any time you are talking to an investor, whether in a pitch deck or during due diligence, they expect you to show financial projections. Many founders run into trouble with this when the company is mostly or entirely pre-revenue. You might wonder what you can show with no track-record. Even so, financial projections are still essential both to the investor and to your strategy.

Right off the bat, let's be honest. Angels know that your numbers are going to be wrong. That is the only thing they can be sure of.

Angel investors are an idiosyncratic bunch; we all have different things we are looking for in a business and in financial projections. I want to see the founder tell a not impossible story about their company’s success. We all know that it is likely that you will need to pivot at some point, but you still need to show that your initial plan could work and produce substantial returns on my investment. Of course, that means you will have a chart showing hockey-stick growth. But don't just make up the numbers, show that they are plausible, or better yet likely.

Read the blog version: https://ftb.bz/startup-financials

Listen to the podcast: https://ftb.bz/podcast

Links from the episode:

Embrace the Pivot- https://youtu.be/OEDmau9ljoU

Why do Angels Demand 20X returns - https://youtu.be/J7tnKZW7TXg

The Three Kinds of Virality - https://youtu.be/jyxTtZ6Gl0w

Test Driving Your Business - https://youtu.be/MLJQMRIIm7Q

19 Apr 202027. How To Launch A Startup With Zero Capital00:11:57

Video: https://ftb.bz/27V

Blog: https://ftb.bz/27B

Episode on testing assumptions: https://ftb.bz/21B-testing-assumptions

Starting a business with nothing

A viewer recently asked me how he could launch a startup when he does not have any significant savings or wealthy connections. With just an idea, but no source of capital, he is going to have to do this the hard way because no outside investor will ever fund a first-time entrepreneur with only an idea. If an entrepreneur has a significant track record of successful exits, then they might be able to get investment in their idea, but at that point, they would also have friends and family with money.

If you are in this position, your first step is research and lots of it. You need to know everything about your business and market. Fortunately, it takes little or no money to conduct this kind of research and experimentation. For a company starting with no capital, avoiding waste and mistakes is even more critical. I wrote an entire episode on testing assumptions.

Can you build it yourself?

Engineers found most tech startups because they can build the initial prototypes themselves. They use their time, rather than cash to launch the company, avoiding the whole problem of fundraising on an idea.

If you are launching a software-based business, can you code it yourself? You don't need to be the best programmer, just good enough to create a proof of concept or prototype that can demonstrate and validate the company's premise. I wrote much of the early code for Anonymizer and a few other products. I am not a professional developer, and that software was spaghetti code of the worst kind. But it got us initial customers and demonstrated that the idea was valuable or, in some cases, not. The same concept applies equally to hardware and service-based businesses if you have the needed skills.

With just enough functionality to demonstrate your capability, and to validate customer demand and engagement with the solution, you are ready to bring your company to outside investors.

If you can't build it yourself

But what if you are an expert in business, sales, or marketing but have none of the skills required to create the solution? After you have finished all of the research and testing you can do without a product in hand, you must start evangelizing your startup to more technical entrepreneurs.

Many technically skilled individuals want to be entrepreneurs but don't have an idea for their own business. Get them excited about your idea and bring them onboard. It may take a long time to find the person who both has the skills you need, and fully appreciates and shares your vision.

This person will be your co-founder. They can spend their time creating the prototype and MVP while you focus on networking, pre-marketing, creating visibility, and yet more research. Mutually respectful technical and non-technical founding teams are incredibly powerful and attractive to investors. Your new technical co-founder will expect, and deserves, a substantial stake in the company. You literally could not do this without them, and they are not getting paid any salary.

Spend time not money

People often say that we should always spend money to save time. In this no-money situation, the opposite advice applies. In an unfunded startup, you are using time, which you have, to avoid spending money, which you don't. Beyond creating your prototype / MVP and doing research & testing, many of the other activities you should pursue depend on whether you are creating a consumer-focused offering or a B2B company.

Consumer

· Leverage free tools and online communities to get beta testers and early users. ProductHunt.com is a good example.

· Engage in social media to build a following and create excitement about what is coming.

· Participate in relevant online communities that will provide visibility, future users, advisors, partners, and investors.

· Leverage PR if your solution is newsworthy. A company I help gets amazing PR because he is a veteran who makes a device addressing PTSD.

· Use inexpensive online ads to test your messaging and the market need. You can learn a lot from just $100.

B2B

· Network with everyone in the space, in person, on LinkedIn, in forums, etc.

· Ask for referrals and introductions to potential partners and customers.

· Join associations and groups (that are cheap or free)

· Attend industry events (that are cheap or free)

· Spend time meeting and talking with potential customers, not to sell them but to learn from them.

For everyone

· Attend and present at pitch contests to hone your message, meet other entrepreneurs, and connect to advisors & investors.

· Join quality accelerators or incubators for networking, logistical support, discounts, and sometimes funding.

· Find potential advisors and sell them on the exciting prospects for your business. They can help with strategy, tactics, and growth. They should also make introductions and generally provide an experienced outside perspective.

A long hard road

Because you won't have any cash to spend, building your company to the point where angel investors are interested may take a long time. The process is challenging but not impossible. By the time you are ready for fundraising, you may be so good at bootstrapping that you find you don't need to bring in investors after all.

05 Apr 202026. Five critical steps to save your startup during a catastrophe like COVID-1900:09:19

During any economic crisis, startups need to take immediate and radical action to stay alive. While I wrote this in response to the pandemic, the advice applies to any situation creating an existential threat to your company.

My most significant experience with this kind of challenge was in the aftermath of the tech bubble bursting in 2000. Everything in the dot com sector seemed to grind to a halt. Surviving required that we significantly change the way we operated. The following five actions saved the company.

1. Reset Expectations

2. Seek Opportunity

3. Hoard Cash

4. Slash Costs

5. Don’t Pay Your Bills

Watch the video of this episode: https://youtu.be/_fqYF2qREaw

Read the blog version: https://ftb.bz/Crisis-survival

22 Mar 202025. In startups, distractions are everywhere. Entrepreneurs must find the fine balance of intense focus without rigidity.00:16:11

Blog: https://ftb.bz/25PB

Video: https://ftb.bz/25PV

Intro

Founders can be like hound dogs on a trail. They are tracking a scent, absolutely focused on their objective. Then suddenly: Squirrel! The CEO races off after some new enticing goal, possibly causing catastrophic damage to the core business. For all companies, but especially for startups, focus is critical.

A founder I advise recently asked if they needed to be looking for an opportunity to pivot. They had seen the "Feel the Boot" on pivots and thought I was saying that they should be trying to pivot. My actual point was that while pivots end up being necessary for most companies, and should not be avoided, they are not something to seek out on their own. Changing direction without purpose is just a random walk. Pivots are a response to an underperforming business plan.

The founder suggested that I should create a balancing episode about the importance of focus. So, here it is.

Sources of Distraction

There are countless sources of distraction for an entrepreneur. News and social media are overflowing with new shiny objects: some new tech stack, development tool, development methodology, cloud service, API, marketing channel, etc. New technologies are particularly distracting to engineer founders.

New markets can be another big distraction. Suddenly you realize that a whole different class of people needs something similar to what you are already building, and surely it would not be too hard to accommodate them as well. Right?

Existing customers can also drive distraction. They will ask for new features or capabilities specific to their circumstances. It can be tempting to drop everything to give them what they want. While these might be great ideas, always consider them within the broader product roadmap and customer base.

One company I am helping makes a wonderfully simple and effective medical device. One potential customer wants to have motion tracking and networking added to it so they can collect data on the users. The founder wants to add that capability. I am less enthusiastic. While this might be a productive new direction, my concern is that it will delay the product by at least several months. At the same time, it is not clear that adding this feature would increase sales and margins overall, or that the customer would refuse to buy without it.

On the other hand, distractions can also come from advisors, so be careful when listening to them (me). We have lots of ideas that can help your business but might not be something you can address right now.

All of these distractions are incredibly attractive because the grass always looks greener in the fields you have not explored yet. You know the challenges with what you are trying to do now, but those new things look easy.

Benefits of Focus

Entrepreneurs need to focus because they have way too many ideas. Scanty time and cash resources require a tight focus on only those efforts and deliverables central to the business. Creating the perfect minimum viable product addressing the needs of a narrowly defined customer set can be all you need to start the business growing.

That single targeted and polished offering can generate far higher returns than creating additional parallel capabilities within your solution.

Focus also helps clarify your vision to several different audiences. Your teams, from development to marketing, will all understand exactly what the company does and what you are trying to accomplish. Your potential investors will see what you are selling, who you are selling to, and appreciate the business model. Your prospective customers will gain a clear idea of how your offerings fit into their business and address their pain points.

Pain of Digression

Lack of focus leads to being spread too thin. Each of the multiple activities you pursue receives fewer resources than required. Even with perfect focus, in most startups the core of the business gets less attention than it needs, so with parallel efforts, the shortfall multiplies.

We lose a tremendous amount of time and energy every time we switch tasks or change priorities. For that reason alone, we should never change direction frivolously. I have seen many projects in easily distracted organizations that never get finished because the constant reshuffling of tasks repeatedly pushes the completion date over the horizon.

I think this killed one of the companies I helped last year. They wanted to create a comprehensive experience for their users, and so tried to provide a whole range of features that people said they wanted to see. However, this diffusion of effort left the core invitation and new user onboarding capabilities underdeveloped and untested. Those processes were awkward and complex. As a result, users never really engaged in the platform at all, making it impossible to raise additional capital and dooming the business.

The Balancing Act

Founders need to find a balance between focus and flexibility. It is a Zen thing, like when my Tai-Chi instructor said that my elbow had to be "bent, but not bent and straight but not straight." You need to be laser-focused on your most important objectives right up until the moment you take the considered decision to change them. Never allow yourself to follow a random walk from shiny object to shiny object, but also keep an eye out for the opportunity and necessity to pivot to a new direction when the current one is failing, or you have real evidence that the new course is better.

So, my Zen wisdom is “be as focused and disciplined as possible, but not more so.”

It is hardly a new thought that choosing what not to do is often more important than choosing what to do. The large number of opportunities combined with constrained time and resources means that you will be saying no to things far more often than yes. For those times you do need to change direction, make sure it is thoughtful and intentional, not reactive and Squirrel!

08 Mar 202024. Why do most founders and entrepreneurs feel like frauds and suffer from impostor syndrome?00:10:47

Watch the video: https://ftb.bz/impostor-video

Read the blog: https://ftb.bz/impostor-blog

The topics for these blogs come from the things I discuss most often with founders. Once they have started to trust me, they almost always talk about how they feel like frauds who will soon be caught and exposed. Even the most talented and successful feel this way. That is when I tell my favorite anecdote from author Neil Gaiman. http://journal.neilgaiman.com/2017/05/the-neil-story-with-additional-footnote.html

Some years ago, I was lucky enough invited to a gathering of great and good people: artists and scientists, writers and discoverers of things. And I felt that at any moment they would realize that I didn’t qualify to be there, among these people who had really done things.

On my second or third night there, I was standing at the back of the hall, while a musical entertainment happened, and I started talking to a very nice, polite, elderly gentleman about several things, including our shared first name*. And then he pointed to the hall of people, and said words to the effect of, “I just look at all these people, and I think, what the heck am I doing here? They’ve made amazing things. I just went where I was sent.”

And I said, “Yes. But you were the first man on the moon. I think that counts for something.”

And I felt a bit better. Because if Neil Armstrong felt like an imposter, maybe everyone did. Maybe there weren’t any grown-ups, only people who had worked hard and also got lucky and were slightly out of their depth, all of us doing the best job we could, which is all we can really hope for.

Impostor Syndrome


People with impostor syndrome engage in a psychological pattern of doubting their competence and accomplishments. In short, they feel like frauds. They attribute any successes or recognition to either luck or deception. A UK study https://www.thehubevents.com/resources/impostor-syndrome-survey-results-116/ shows just how common this is, with 85% of people admitting to feeling inadequate or incompetent at work. Most of those people suffer in silence because they think they are alone in this. Only 25% are aware of the existence of impostor syndrome. Entrepreneurs with these feelings are often paralyzed with self-doubt, harming their businesses and chances for success.

I experience impostor syndrome all the time, despite any objective evidence to the contrary. For example: I studied astrophysics in graduate school. I founded a company and brought it to a successful exit. I have been invited to speak at conferences around the world. I have dozens of published articles. I am regularly sought out as an authority on multiple subjects.

Yet, I had a hard time writing that paragraph or believing those statements. In particular, I feel impostor syndrome every time I write or record for Feel the Boot.

I suspect that impostor syndrome is even more common among entrepreneurs than in the general population. We are high achieving people with high expectations. Our role models tend to be the most successful founders and CEOs in the world, people like Steve Jobs, Elon Musk, or Jeff Bezos. If they are our reference for what we should be as founders, it is no wonder we feel that we fall short. We also tend to surround ourselves with amazing people, far above the average, which skews our perspective on our qualities.

Anti-Impostor Syndrome

There is a mirror image to impostor syndrome in a set of people with no doubt about their worth or ability. Interestingly, where people with impostor syndrome underestimate their competence, this other group generally overestimates it.

The Dunning-Kruger effect describes this odd relationship where self-assessed competence is often inversely proportional to actual competence. High performing entrepreneurs tend to assume that everyone around them is at or above their level.

I think that part of this has to do with knowing what we don’t know. The greater your knowledge of a subject, the more you understand the vast extent of your ignorance. With each increase in knowledge or skill, we simultaneously discover an even larger set of new things about which we are ignorant. In my experience, true experts are humble in the face of the ocean of unknowns they can see.

Conversely, people who only know a little often think that is everything there is to know.

A Vaccine Against Impostor Syndrome.

Just recognizing the existence, and near ubiquity, of impostor syndrome among founders can go a long way to reducing its impact. Thinking of Neil Armstrong’s self-doubt gets me through many crises of confidence.
Knowing that we tend to undervalue our true areas of expertise, try to take a hard and realistic look at your abilities. Recognize where you are strong, and hire or otherwise compensate for the areas where you are objectively weaker.

One path to recognizing our strengths is to start taking compliments seriously. If you regularly hear positive and specific statements about yourself or your work, believe them!

Many of us suffer needlessly with this problem because we think we are alone. Entrepreneurs are constantly selling and pitching, and one of their key products are themselves. We often try to create an image of the perfect confident leader and visionary. It would be healthier for all of us if we could, even just in private with each other, admit and share these feelings. It goes a long way to reducing the burden. The community of entrepreneurs is powerful. We need to leverage our networks for mutual support far more than we do.

23 Feb 202023. Why are even successful startups and entrepreneurs having trouble raising their Series-A rounds?00:08:27

When I talk to startup founders or angel investors, one topic has started to dominate the conversations: the lack of A round financing.

Video: https://ftb.bz/a-round-video

Blog: https://ftb.bz/a-round-blog

Podcast: https://ftb.bz/podcast

Many founders and seed stage investors have a story for how a startup will grow. Initially friends and family will fund early prototypes. About six months later, once there is some traction and market interest, angel investors will fund the work required to demonstrate product market fit. Six months to a year after that the company will close a $5 million series-A round that will fund explosive growth.

But in reality, it is taking much longer to reach that A round investment, often a number of years. So the CEO needs to find other ways of funding the business until it happens, or skip further funding entirely.

I am working with several companies right now that: have working products, that customers like, are growing, and generating revenue. Yet, after multiple years of effort, they still can’t close that A-Round.

The problem with A rounds is structural. Funds are getting bigger which leads to larger investments. Investments of any size require a similar amount of work from the VC firm. With a larger amount of cash to deploy and a roughly constant amount of labor available, the rounds need to be larger. Rather than investing $5m, I am hearing that many investors won’t invest less than $15m.

Of course, with that larger investment comes higher expectations. Reaching those higher hurdles takes longer and consumes more cash. The entrepreneur typically needs to to back to angel and seed round investors multiple times before they clear them.

At Anonymizer, we raised a total of $2.5 million over about 7 years, all from angel investors. The slow growth in the consumer space never got us to a place where we could bring in VC with their larger investments, even in the more permissive late 1990’s environment. As it turned out, that saved us when the market crashed in 2000 because we were small and lean, unlike some well funded competitors who had high burn rates but no prospect for additional money.

Other than in the medical space, which seems to have its own set of industry specific hurdles, I am seeing three paths to A-round funding.

The first is to be growing exponentially. While 30% year over year growth is respectable, the VC are looking for 30% month over month, doubling every quarter. In addition to that, they are looking for strong fundamentals and unit economics. Finally, they want to see a clear path to continued growth at that pace. With all that in place, the investment decision is fairly easy.

Another path is to have the right history or some unfair advantage. If you have multiple massive prior exits investors are much more likely to take a chance on this next venture. Similarly, if you have a rockstar team of people with track records of amazing execution, they will have more confidence that they can do so again. Finally, investors tend to move as a herd. If you have extremely impressive investors in your seed round, they will know the general partners at the VC firms and be able to leverage their reputations to secure the investment.

The final path is to create enough track record to remove the risk. If the company has been executing for several years showing reasonable growth and reliable results, it will be in a position where a $15 million investment is warranted and relatively safe.

Anonymizer never did raise an A round. Once we did our big pivot towards the national security community we started generating revenue faster than we could effectively spend it. While the VC might have been interested in us, we no longer needed them.

Like Anonymizer, you might choose take many small investments until the company is self sustaining. Alternatively, you might be able to bootstrap the business with little or no funding at all.

Sometimes the problem with growth is timing. The market forces and conditions are not yet right for your business. If that is the case, and you are confident they will be aligned soon, then just surviving till then can be the right strategy.

Finally, it might be a sign that your business model is just not going to work. You either need to pivot to something that will generate the growth you need, or you should wind things down and look for a new opportunity entirely.

Fortunately, two companies I have helped recently scored A-Round funding. One through the medical device exception, and the other through the long track record of reliable growth approach.

The key is to build your business in a way that it can succeed even if the A round funding take much longer than expected or never happens at all. Model your finances without that investment to make sure the company has a viable plan B for survival and success. In this new reality, angel and seed investors need to see that kind of robust business model.

10 Feb 202022. One thing most successful companies share: a pivot00:10:37

Almost all successful companies share one thing in common: a pivot. When your startup hits a wall, the best path may be to change direction to go around it, rather than trying to bash your way through. Learning and adapting can be the best path to growth and success.

Video: https://ftb.bz/Pivot-video

Blog: https://ftb.bz/Pivot-blog

27 Jan 202021. Build a strong foundation for your startup by testing assumptions first00:09:10

Entrepreneurs are always enthusiastic about their next business idea. They often avoid asking the hard questions that could undermine their plans. In this episode, I explore the importance of testing your assumptions and how to actually do it. Early experiments will reduce your risk and impress potential investors.

Video: https://youtu.be/MLJQMRIIm7Q

Blog: https://FeelTheBoot.com/blog/test-driving-your-business

13 Jan 202020. Passion is the secret weapon of successful entrepreneurs. Learn how to identify and leverage it.00:09:36

Everyone has been told to follow their passion. What they don’t learn is how to identify and leverage that passion. That energy is the unfair advantage of the best entrepreneurs. This episode shows how to connect your business to your passion with examples from my own path to startup success.

Video: https://youtu.be/_4NvC0SEU3Q
Blog: https://FeelTheBoot.com/blog/powerofpassion

30 Dec 201919. Raising Capital: Why you need more money than you think00:05:51

When you are raising funds for your startup, one of the biggest questions is, How much should I ask for? Don’t let concerns about dilution tempt you into raising too little money in your investment rounds.

Video: https://youtu.be/20NbJ9LxTag
Blog: https://FeelTheBoot/blog/raising-enough-capital

16 Dec 201918. While starting a business, when should you quit your day job?00:09:35

One of the most frightening moments as an entrepreneur is when you finally quit your day job. Fortunately you can risk reduce that transition and improve your chances for angel funding at the same time.

https://youtu.be/jUY-Vjz83lo
https://FeelTheBoot.com/blog/quityourdayjob

02 Dec 201917. Nail the start of your investment pitch00:06:49

I lose interest in most of the pitches I see within the first thirty seconds. After that, it is incredibly difficult to get me back on board. This is a common experience with most investors. I am going to share with you what goes wrong and how to nail the opening of your pitch.

Video: https://youtu.be/88FOE093LsQ

Blog: https://www.feeltheboot.com/blog/hook-investors

18 Nov 201916. Why founders don’t delegate as much as they should00:11:08

Most growing startups quickly reach a point where they are choked by the founder’s limited time. As humans, we simply don’t scale well. There is only so much that efficient work and forgone sleep can squeeze out of a day. The problem is that the entrepreneurs need to delegate more of their responsibilities. This is not an intuitive process for most of us. The typical career path is all about accumulation responsibility and power. Rising through the ranks and building ever larger fiefdoms. As a founder, you go through the opposite process. Founders start off doing literally everything. They are CEO, accountant, customer support, and janitor. Between there and running a large successful company, they need to delegate almost all of that.

Video: https://youtu.be/S_KTNIM5UMs

Blog: https://www.feeltheboot.com/blog/delegation

04 Nov 201915. Priorities and Perseverance: Finding balance and moving forward in the face of major adversity00:05:29

I recorded the video for this episode in a hotel room while evacuated from my home because of the Kincade fire in Northern California. I wondered if I should just skip this episode because I was feeling very stressed and distracted. I decided that it might be interesting to do a short episode about how sometimes life makes you look at where your true priorities lie. Video: http://bit.ly/2pCGfWa Blog: http://bit.ly/32a7qVt

Video: http://bit.ly/2pCGfWa
Blog: http://bit.ly/32a7qVt

21 Oct 201914. My #1 advice to startups: Always be due diligence ready00:10:13

When founders come to me for advice, they are often looking for help with pitching, fundraising, strategy, or security. At some point, they will often ask what one piece of advice I would give them. I always tell them “stay due diligence ready”. This comes from my personal experience of being totally unprepared when an offer to buy my business come out of the blue five years after starting. What followed was months of the hardest work and longest days I have ever experienced. We had to obtain signatures from former employees and past vendors for work done years earlier. We hunted through old emails for key contracts and agreements. It was a mess. If we had started keeping all of our records organized early on, and kept them up to date, we could have avoided all that pain. In the end, the deal fell through and it was for the best, but it was an experience I will never forget. The bottom line is that it is much easier to stay due diligence ready than to get due diligence ready, and the earlier you start the simpler the process will be. Investors will want different things, so it is impossible to be perfectly prepared but with the right systems and processes you can be 99% ready and able to fill in that last part with minimal effort. The following is my list of the records you need to have close to hand and up to date.

Video: https://youtu.be/4dMpbfNaB-M

Blog: https://www.feeltheboot.com/blog/duediligenceready

07 Oct 201913. The three kinds of viral growth and how to use them in your startup00:15:45

Virality is the holy grail of business growth strategies. In this installment I explain the three kinds of virality and how you can leverage them in your startup. Investors love viral business models, but are also skeptical of the claim. Through early testing and clear analysis, you can show why your company has the potential for viral hyper-growth.

Video: https://www.youtube.com/watch?v=jyxTtZ6Gl0w

Blog: https://www.feeltheboot.com/blog/virality

23 Sep 201912. How to pitch your blockchain startup to a skeptical investors00:16:03

If you are launching a blockchain based company, I have some specific advice for you. Right now, I see many times more blockchain and Initial Coin Offering pitches than anything else. And most of them are bad. This creates additional hurdles that I want to help you navigate. The tsunami of blockchain pitches causes investors to set the bar very high. At the same time, the entrepreneurs are making a lot of unforced errors. Learn what these other founders are doing wrong and how you can deliver a pitch that will stand out and interest investors.

Video: https://youtu.be/jOAcvAyttJY
Blog: https://feeltheboot.com/blog/blockchain-pitching-mistakes

09 Sep 201911. Understanding Control and Power in Your Startup00:08:32

Your business is your baby. You don’t want anyone to take it. But holding on too tight could smother it. Understanding the dynamics of power and control in a startup will allow you to grow and succeed. 51% ownership is less important than you might think and the contortions required to hold that number can scare off the investors you need.

Video: https://bit.ly/51percent-video
Blog: https://bit.ly/51percent-blog

26 Aug 201910. Understanding how and why to leverage stock options in your startup00:15:13

Founders and entrepreneurs need to understand the inner workings of stock options. Otherwise they can waste equity, disappoint key employees, and dilute their ownership. In this episode I cover: Why you should issue options How to create an option plan Setting up the initial option pool Negotiating changes to the option pool How many options to grant an employee How to vest options

Video: http://bit.ly/stock-options-explained-video
Blog: http://bit.ly/stock-options-blog

https://tools.ltse.com/sizing-the-option-pool-whats-normal-95e0f2bc0b88
https://gust.com/launch/blog/how-much-equity-should-you-offer-your-startup-team-members
https://firstround.com/review/The-Right-Way-to-Grant-Equity-to-Your-Employees/

12 Aug 20199. Understanding stock options from the employee perspective00:14:17

Many times, when giving out stock options, I found that the recipient did not understand them. Options are one of the most important employee motivators and a big part of their compensation, and confusion substantially reduces their effectiveness. This episode is devoted to educating employee about the options they receive and helping founders explain them to their teams.

Video: http://bit.ly/options-explained-video
Blog: http://bit.ly/options-explained-blog

29 Jul 20198. Pre-Seed Through A and Beyond: What are all those investment rounds?00:15:07

Founders are confused about all the different terms used for funding, and what they all mean. Are they ready for a seed round and what does it take to get an A round? Learn what each kind of investment round means, what to expect, and what investors will expect from the business. Making the right ask to the right people at the right time is one of the keys to startup fundraising.

Video: https://bit.ly/investment-rounds-explained-video
Blog: https://bit.ly/investment-rounds-explained

15 Jul 20197. Why ideas matter less than execution to investors and your startup business00:13:41

Media and popular culture focuses excess attention on flashy “big ideas”, but it is excellent “execution” that separates the massive successes from the failures. Too many founders focus on finding that perfect idea, rather than making a great business out of a good idea. Investors need to know how you are going to grow. Focus on the things that you are going to do more than on the big picture.

Video: http://bit.ly/execution-over-ideas-video
Blog: http://bit.ly/execution-over-ideas

01 Jul 20196. How to get funding for your startup company - answering a viewer question00:28:16

Trying and failing to raise funds for your startup business? In this episode I answer a viewer question asking for suggestions. Learn what it takes to get funding from early stage investors.

Video: http://bit.ly/finding-investors-vid
Blog: http://bit.ly/finding-investors
Links mentioned in the podcast:
The Angel Capital Association https://www.angelcapitalassociation.org
Blog on Why Angel Investors need high returns https://www.feeltheboot.com/blog/greedy-angel-investors
Two lists of Community Development Financial Institutions https://fitsmallbusiness.com/community-development-financial-institutions-cdfi-list/ https://about.bankofamerica.com/en-us/partnering-locally/cdfi-list.html
My previous video on how to build a presentation: https://www.feeltheboot.com/blog/2019/4/1/bad-presentations-can-scuttle-your-startup-make-yours-soar

17 Jun 20195. The two pitch decks you need to get angel investment00:07:49

Your investor pitch may be failing because you are using the wrong deck! I have seen many otherwise good investment pitches fall flat because the speaker used a deck that was not optimized for the environment. Sometimes you will pitch in person, and sometimes your deck will be read alone. In this episode I cover how to triumph in both scenarios.

Blog: https://www.feeltheboot.com/blog/startups-need-two-pitchdecks

Video: https://www.youtube.com/watch?v=d-QhA47gWmg

03 Jun 20194. Your Non Disclosure Agreement can poison the well for angel investment00:06:13

Asking for an NDA up-front can kill your chances for investment. Non-disclosure agreements have their place but they can stop a conversation with angels or VCs before it starts. Handle this situation correctly and you will have nothing to fear.

Blog: https://www.feeltheboot.com/blog/no-nda-before-pitch

Video: https://www.youtube.com/watch?v=ZyI34GCDUj4

20 May 20193. Are angels greedy to demand a massive 20X return on investment?00:07:48

Angel investors demand massive potential returns. Understanding why is the key to a successful pitch. Entrepreneurs in startups need to know the economics that drive angel investors and the harsh reality of how many startups fail.

Blog: https://www.feeltheboot.com/blog/greedy-angel-investors

Video: https://www.youtube.com/watch?v=J7tnKZW7TXg

06 May 20192. Why I don’t care about your technology!00:09:35

Engineer entrepreneurs love their technology, but that can be their downfall. In an investor pitch, when and if you talk about your technology can make a huge difference. Leading with, and focusing on, technology is the biggest mistake I see many engineer entrepreneurs make. The technology is often what they are most passionate about and was the reason they created the company. Technology is also where they feel most comfortable and can speak most confidently. Unfortunately that comes at the expense of focus on customers and their pain points.

Read the blog version of this episode here: https://www.feeltheboot.com/blog/angel-pitch-deck-not-technology

Watch the video version of this episode here: https://www.youtube.com/watch?v=BLpHXWGQsrE

22 Apr 20191. Is your passion project worth a day of your vacation time?00:06:13

Are you having trouble getting your big project off the ground? I had a hard time finding the time to launch Feel The Boot. Eventually I realized that I would have to take some time away from my day job to just make it happen. I suspect that this is a very common experience. If you have a question, topic suggestion, or feedback, message me on Twitter @LanceCottrell or contact me through the https://FeelTheBoot.com website

Blog: https://www.feeltheboot.com/blog/unsticking-your-passion-project

Video: https://www.youtube.com/watch?v=apK2eGBiiOY

04 Mar 202270. High valuations can demotivate employees and derail investment00:11:28

In this episode I explain why a very high valuation can cause trouble for your startup.

It can demotivate your employees by hurting their payout at exit.

It can derail your next funding round my making your last investors hostile and demanding.

 

Read this as a blog: https://ftb.bz/70B

Watch the Video: https://ftb.bz/70V

Join the Founder’s Alliance: https://ftb.bz/Alliance

Subscribe to Boot Prints for free office hours: https://ftb.bz/Join

09 Mar 202271. How to get startup mentoring and advising at Feel the Boot00:03:54

Feel the Boot 🤓 Mentoring & Advising

How our free mentoring office hours work

Establishing formal advising relationships

 

Subscribe to Boot Prints: https://ftb.bz/Subscribe

Join Founders Alliance: https://ftb.bz/Join

Read this: https://ftb.bz/71B

Watch the Video: https://ftb.bz/71V

 

Lance Cottrell has been an active startup advisor and startup mentor for over a decade.

His advice and mentoring can supplement or replace startup accelerators or startup incubators like Y Combinator.

He provides help with startup funding including raising venture capital and angel investment.

He can help you achieve liquidity for your company at a high valuation.

Feel the Boot is a startup vlog of tips and advice for early-stage founders.

22 Mar 202272. Get more value from your startup advisors00:09:48

Startups 🧐 business advisor value

Get more value from your startup advisors

How to use mentors more effectively

 

If you have not recruited your advisors yet, watch this first: https://ftb.bz/68V

The video on Founder Time Management for Strategic Thinking is here: https://ftb.bz/65V

Read the blog: https://ftb.bz/72B

Watch the Video: https://ftb.bz/72V

Join us to access free one-on-one office hours: https://ftb.bz/Join

Meet other entrepreneurs at the Founders Alliance: https://ftb.bz/Alliance

 

In this episode I share best practices for working with your advisors and mentors.

Advisors should be more than just a pretty face on your pitch deck. You give them equity, so you should maximize their value to you.

Advisors can help you with startup funding, angel investors, venture capital, pitch decks, growth hacking, startup marketing, product sales, PR, mergers and acquisitions, and more.

 

Lance Cottrell has been an active startup advisor and startup mentor for over a decade.

His advice and mentoring can supplement or replace startup accelerators or startup incubators like Y Combinator.

He provides help with startup funding including raising venture capital and angel investment.

He can help you achieve liquidity for your company at a high valuation.

Feel the Boot is a startup vlog of tips and advice for early-stage founders.

13 Apr 202273. When your startup hits hard times: quit, pivot, or persevere?00:11:35

Startup Survival 🤕 Quit, Pivot, or Persevere

When your startup hits hard times what should you do?

Make this high stakes decision with confidence

 

When your startup is in a dark place with no path forward, what should you do?

This episode explores how to analyze your options objectively to choose the best option for you and your startup.

 

Subscribe to Boot Prints: https://ftb.bz/Subscribe

Join Founders Alliance: https://ftb.bz/Join

Read this: https://ftb.bz/73B

Watch the Video: https://ftb.bz/73V

 

Lance Cottrell has been an active startup advisor and startup mentor for over a decade.

He has helped countless startups navigate the key decisions of their journey, like when to close their startup vs. persevere or pivot.

His advice and mentoring can supplement or replace startup accelerators or startup incubators like Y Combinator.

He provides help with startup funding including raising venture capital and angel investment.

He can help you achieve liquidity for your company at a high valuation.

Feel the Boot is a startup vlog of tips and advice for early-stage founders.

02 May 202274. What is a Cap Table? Tracking VC Investments and stock option grants00:19:06

What is a Cap Table? 🧐 Tracking VC Investments and stock option grants

Understand startup capitalization, preferred stock, and angel investments

Track ownership, options, SAFE, Convertible Notes, and dilution.

 

Startup equity and cap tables can be confusing to many founders.

The CEO needs to understand startup equity well enough to talk to their lawyers and negotiate with investors. This episode will teach you all you need to know.

 

Subscribe to Boot Prints: https://ftb.bz/Subscribe

Join Founders Alliance: https://ftb.bz/Join

Read this: https://ftb.bz/74B

Get the video: https://ftb.bz/74V

 

Lance Cottrell has been an active startup advisor and startup mentor for over a decade.

He has helped countless startups navigate the key decisions of their journey, like when to take venture capital investment and negotiating a termsheet.

His advice and mentoring can supplement or replace startup accelerators or startup incubators like Y Combinator.

He provides help with startup funding including raising venture capital and angel investment.

He can help you achieve liquidity for your company at a high valuation.

Feel the Boot is a startup vlog of tips and advice for early-stage founders.

20 May 202275. Surviving a Short Runway. Startup burn rate < 6 months cash00:13:42

Low on cash with no imminent funding?

Here’s how to keep your startup alive

 

Read this as a blog: https://ftb.bz/75B

Watch the Video: https://ftb.bz/75V

Visit the website: https://ftb.bz/

Join the mailing list: https://ftb.bz/Join

 

When things get tough and cash is short, you need to manage your startup cash flow to survive. If things are particularly difficult, you might be forced to pivot or sell the company.

 

Lance Cottrell has been an active startup advisor and startup mentor for over a decade.

He has helped countless startups navigate the key decisions of their journey, like when to take venture capital investment and negotiating term sheets.

He works with many companies in accelerators like Y Combinator and Founder Institute.

He provides help with startup funding including raising venture capital and angel investment.

He can help you achieve liquidity for your company at a high valuation.

Feel the Boot is a startup vlog of tips and advice for early-stage founders.

16 Jun 202276. Investor Updates: how, why, and an investor update template00:10:31

Get more from your investor updates

What to include and an easy template

 

Get the template here: https://ftb.bz/investor-update-template

 

Watch the Video: https://ftb.bz/76V

Get the podcast: https://ftb.bz/Podcast

Visit the website: https://ftb.bz/

Join the mailing list: https://ftb.bz/Join

 

A regular investor update email is the best way to keep existing and prospective investors in the loop on your startup’s progress.

Use it to ask for investments, introductions, advice, assistance, and more.

In this episode I share how to craft an update that people will read and will keep them engaged and supportive.

 

 

Lance Cottrell has been an active startup advisor and startup mentor for over a decade.

He has helped countless startups navigate the key decisions of their journey, like when to take venture capital investment and negotiating term sheets.

He works with many companies in accelerators like Y Combinator and Founder Institute.

He provides help with startup funding including raising venture capital and angel investment.

He can help you achieve liquidity for your company at a high valuation.

Feel the Boot is a startup vlog of tips and advice for early-stage founders.

28 Jun 202277. Pitching when tech’s glitching. Handle PowerPoint failure with style!00:11:53

Have you ever tried to deliver a pitch deck or other presentation, and the technology just won’t cooperate? Either your computer won’t talk to their projector, or there is some issue with the PowerPoint.

How can you handle these situations in a way that leaves you looking as good or better than you would have if everything had gone perfectly?

Video: https://ftb.bz/77V

Article: https://ftb.bz/77B

Join: https://ftb.bz/Join

21 Jul 202278. Investment Term Sheets: Explanations, Red Flags, and where to push back00:38:04

Term Sheet Red Flags ☠️ Venture Capital

Abusive terms cause dilution, loss of control, & sabotage future deals

Learn what they mean and when to push back

 

Read the article https://ftb.bz/78B

Watch the video https://ftb.bz/78V

Founders Alliance https://ftb.bz/Alliance

Mailing list for office hours https://ftb.bz/join

 

Article on pre-revenue startup valuations: https://ftb.bz/66B

Article on why high valuations can be bad: https://ftb.bz/70B

 

Here are the standard term sheets I mentioned:

Y Combinator https://ftb.bz/Y-Com-TS

National Venture Capital Association https://ftb.bz/NVCA-TS

Angel Capital Association https://ftb.bz/ACA-TS

24 Aug 202279. Cofounder Vesting Handling founder shares when things go wrong00:12:37

Cofounder Vesting 😭 Handling founder shares when things go wrong

Stock vesting can save you in multi-cofounder startups

Investors may require founder vesting before investing

 

This episode looks at the issue of founder vesting through the lens of a fictitious company founded by Iron Man, The Hulk, Thor and Loki.

 

Read the article https://ftb.bz/79B

Watch the video https://ftb.bz/79V

Founders Alliance https://ftb.bz/Alliance

Mailing list for office hours https://ftb.bz/join

08 Sep 202280. Fire the Founder? Take the initiative and replace yourself as CEO00:18:16

Fire the Founder? 🔥 Take the initiative and replace yourself as CEO

Startup typically outgrow their founding CEO

It’s better find your replacement then be replaced

 

My board of directors wanted to replace me as CEO. This episode explains how I handled that with fantastic results.

If you recruit the new CEO, you can find someone you want to work with, and who will respect you.

They can help drive the company’s success and give you the exit you want.

 

Read the article https://ftb.bz/80B

Watch the video https://ftb.bz/80V

Founders Alliance https://ftb.bz/Alliance

Mailing list for office hours https://ftb.bz/join

19 Oct 202281. My worst day as a founder how we pivoted, survived, and eventually thrived00:21:09

My worst day as a founder 😭 how we pivoted, survived, and eventually thrived

Startup Stories: angel investor quits, acquisition falls through, & personal tragedy

What to expect as a founder.

Creating and growing a company can be an incredible experience, but you will have days that seriously suck. You will probably experience situations that challenge your determination to carry on.

Because I frequently talk about how challenging launching a startup can be, I want to share my worst day as a founder. I hope it helps prepare you for some of the trials you will experience on your journey.

Read the article https://ftb.bz/81B

Watch the video https://ftb.bz/81V

Founders Alliance https://ftb.bz/Alliance

Mailing list for office hours https://ftb.bz/join

05 Nov 202282. Startup Fundraising in a Bear Market00:09:16

📉Startup Funding in a Bear Market

Adapt your fundraising strategy to succeed in a downturn

Raise angel investment and venture capital in challenging times

 

When the economy is rough, investors become cautious.

Learn how to position your company to survive these times and appeal to angel and VC investors.

 

Read the article https://ftb.bz/82B

Watch the Video https://ftb.bz/82V

Founders Alliance https://ftb.bz/Alliance

Mailing list for office hours https://ftb.bz/join

01 Dec 202283. Angel Investing 101 00:13:34

Angel Investing 101 💰

What is angel investing?

How to invest in pre-IPO companies

 

Angel investors put their own money into early-stage startup companies.

This is the first in a series of episodes on becoming an effective angel investor / venture capitalist

 

Read the article: https://ftb.bz/83B

Watch the Video: https://ftb.bz/83V

Signup for the mailing list and office hours: https://ftb.bz/join

19 Dec 202284. How to start angel investing00:11:17

How to Start Angel Investing 💰

What you need to know to start investing in early-stage startup companies

Best practices for new angel investors

 

This is the second in a series of videos on angel investing.

It explains the best way to begin as a new angel investor, and some critical pitfalls to avoid.

 

Read the blog: https://ftb.bz/84B

Watch the Video https://ftb.bz/84V  

Subscribe to Boot Prints https://ftb.bz/join

Here’s the episode on dangerous investment terms https://youtu.be/LCCXSS2ubn8

Merch! https://ftb.bz/merch

05 Jan 202385. How venture capital kills startups ☠️00:12:08

VCs destroy more startups than they make unicorns

Learn how to identify and avoid that trap

 

The reason is the “marginal dollar problem”

Understanding that will help you choose whether to accept venture capital investment with open eyes.

 

Read the blog: https://ftb.bz/85B

Watch the video: https://ftb.bz/85V

Join Boot Prints for access to free office hours: https://ftb.bz/Join

Meet other founders in the Founders Alliance: https://ftb.bz/Alliance

02 Feb 202386. BoD vs. Shareholder ⚖️ Startup Corporate Governance00:12:18

Who decides what between the board and shareholders?

How to handle the BoD and Shareholder meetings as a founder.

 

Read the blog: https://ftb.bz/86B

Watch the Video: https://ftb.bz/86V

Get access to office hours and Boot Prints: https://ftb.bz/Join

 

In this episode, I explain the board of directors and shareholders roles and responsibilities.

Some votes require both groups to approve. Others are specific to the BoD or shareholders.

Running shareholder and board meetings as a startup is easier than you think.

Having those meetings is essential, even if you are the only participant!

14 Feb 202387. Get Angel Investor Dealflow 00:13:53

💸Get Angel Investor Dealflow

You need to look at a lot of startups to find good investments

Learn several ways to uncover quality startups

 

 

Our Angel Investing 101 series teaches new Angel Investors how to invest in startups.

This episode focuses on Angel Investor dealflow. You need to source a lot of potential deals to identify those few worthy of investment.

 

Where to list yourself as an angel investors:

https://LinkedIn.com/

https://signal.nfx.com/

https://www.angellist.com/

https://www.crunchbase.com/hub/angel-investors

 

Syndicate sites:

https://AngelList.com

https://TheSyndicate.com

 

Crowd Funding Sites:

https://Wefunder.com

https://Republic.com

https://Seedinvest.com

https://Fundable.com

https://StartEngine.com

https://MicroVentures.com

 

Read the blog version: https://ftb.bz/87B

Watch the video: https://ftb.bz/87V

Get access to Boot Prints & Office Hours: https://ftb.bz/Join

Feel the Boot Merch: https://ftb.bz/Merch

22 Mar 202388. Talking to friends and family about investing in your startup.00:13:07

Your earliest investors are probably unsophisticated.

You must help them understand how startup investing works.

 

When you are at the idea stage, almost no angel or VC investors will back you, but people who know and care about you might.

Unfortunately, this is usually all new and very confusing to them.

You must ensure they understand what they are doing and paint a realistic picture of the possible outcomes.

This video is for you, the founder. It explains your options for structuring the deal and how to communicate with them about this opportunity.

I created another video to share with your potential investors that tells them what they need to know. https://ftb.bz/friends-and-family-explainer

 

Read this as a blog: https://ftb.bz/88B

Watch the video: https://ftb.bz/88V

17 Apr 202389. Non-Dilutive Startup Fundraising SBIR Grants for Innovation00:49:15

Non-Dilutive Fundraising 💰 SBIR Grants for Innovation

Get cash for your startup without giving up ownership.

Government grants can fund your development from idea to MVP and beyond.

 

Read the transcript: https://ftb.bz/89B

Watch the Video: https://ftb.bz/89V

Subscribe to Boot Prints: https://ftb.bz/Join

Get FTB Merch: https://ftb.bz/merch

Join the Founders Alliance: https://ftb.bz/Alliance

 

 

In this interview, Caroline Arzoo, Director of Partnerships at OmniSync, and I discusses the different options for funding a startup. She emphasizes that federal grants and contracts can be a great alternative to conventional angel and VC investment. However, she notes that the application process can be difficult, with over 80% of people who apply for federal funding on their own getting rejected for non-compliance. To help founders access non-dilutive funding, OmniSync has created an AI-powered platform that simplifies the process of finding and applying for federal funding.

 

In addition to federal grants and contracts, Caroline also suggests considering crowdfunding and pitch competitions as creative funding avenues.

 

She highlights the importance of community, transparency, and being open to change in order to navigate the complexities of growing a startup.

 

We also also touch on the emotional toll of the founder journey and the importance of building a support system.

 

Caroline Arzoo Bio:

Caroline Arzoo is a passionate advocate of innovation, supporting early-stage founders through her community-building work at OmniSync Inc and as a mentor for Founder Institute. A graduate of UC Santa Barbara’s Technology Management program, Caroline has supported hundreds of early-stage startups in accessing non-dilutive capital from the federal Small Business Innovation Research (SBIR) program.


In addition to her work supporting founders, Caroline also works to empower and build innovation ecosystems, partnering with universities, small business development centers, accelerators, and more to support their entrepreneurial initiatives.

Find her on LinkedIn at https://www.linkedin.com/in/carolinearzoo/

 

Check out OmniSync’s grant application tools at https://www.turbosbir.com/

01 Jun 202390. Thirteen Key Considerations for Evaluating Angel Deals Angel Investing 10100:11:16

How to quickly eliminate the losers,

and identify companies worthy of further due diligence.

 

As an angel investor, you will need to look at many startups.

This guide provides a framework for quickly analyzing deals to see if digging deeper is worth your time.

 

This is part of a series on Angel Investing https://ftb.bz/Angel

Subscribe to Boot Prints and access office hours https://ftb.bz/join

Learn about advising from Feel the Boot https://ftb.bz/advising

Watch the Video https://ftb.bz/90V

Read as an article https://ftb.bz/90B

 

Make a Quick First Cut

Is the Company Angel Investable?

Competition

Valuation

Problem/Solution Validation

Business Economics

Defensibility

Intellectual Property

Need for Additional Funding

What is There?

Churn

Assumption Validation

Is This Possible?

(bonus) Team

29 Jun 202391. Non-monetary Startup Rewards and Recognitions00:13:36

Non-monetary Startup Rewards and Recognitions.

Eight employee incentives that work better than cash.

 

In this episode of "Feel the Boot: The Science of Startups," I, discuss seven highly effective motivators and rewards for employees that founders can use to attract and retain top talent. These motivators include having a strong vision, giving employees equity, providing public recognition, delegation and employee empowerment, giving personal attention, tailoring rewards to the individual, and unique “wow” rewards. I emphasize the importance of understanding what motivates individual employees, as what works for one may not work for another. I share two examples of "wow rewards" that have had a significant impact on employees, such as handmade plaques and giving solid gold coins to employees who have put in a "gold medal performance."

 

Access all my content on Running your Startup https://ftb.bz/running

Get this content at an article https://ftb.bz/91B

Watch the Video https://ftb.bz/91V

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18 Jul 202392. The Economics of Angel Investing Angel Investing 10100:15:08

How to create an angel investment portfolio for maximum returns.

Learn what drives the returns for your angel investments.

 

Read this as an article: https://ftb.bz/92B

Watch the Video: https://ftb.bz/92V

Subscribe to BootPrints: https://ftb.bz/Join

Angel Investing 101 series: https://ftb.bz/angel

 

 

In episode, I delve into the economics of angel investing, emphasizing the need for a significant number of investments to increase the chances of success. Research shows that most angel investments result in losses or minimal returns, but a small percentage can yield substantial profits. To improve the likelihood of hitting those winners, you should make at least 20 angel investments. Diversification across different sectors is also crucial to mitigate risks associated with market fluctuations and sector-specific downturns.

 

I then discuss the importance of planning an investment budget. Startups typically prefer pre-seed investments of at least $25,000 to avoid numerous small investments on their cap table. For investors with smaller check sizes, you might explore options like crowdfunding or syndicates. Syndicates involve a lead investor selecting an investment, while crowdfunding platforms allow for lower minimum investment requirements, enabling diversification through multiple smaller investments.

02 Aug 202393. Startup Branding and Positioning Mara Rada Interview00:35:44

Branding is far more than just a logo and color scheme.

Learn how to leverage both positioning and branding in your startup buisiness

 

In today's fiercely competitive business landscape, effective branding and positioning strategies are crucial for startups to stand out from the crowd. However, many founders underestimate the true scope and importance of these concepts. In this interview, we heard valuable insights from branding and positioning expert Mara Rada, shedding light on why these elements are vital for emerging companies. By understanding the multi-faceted nature of branding and the emotional factors that drive purchasing decisions, founders can create stronger connections with their target audience, ultimately leading to long-term growth and success.

 

In the interview, Mara mentioned a few resources that will help founders learn more about branding and positioning:

-       42Courses.com has many lessons on these and related topics.

-       Anything written by George Tannenbaum formerly with Ogilvy, and R/GA https://www.linkedin.com/in/georgetannenbaum/

-       Anything written by Manoj Jacob Creative Director at Crayons. Formerly at Ogilvy, DDB Mudra, Soho Square, & Havas https://www.linkedin.com/in/jacobwriter/

 

Get this as an article: https://ftb.bz/93B

Watch the video: https://ftb.bz/93V

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Mara Rada is a feral thinker, a brand whisperer, and a category positioner. She helps companies create the beast brands of the future without selling their souls. She has worked with some of the world's most remarkable startups, Fortune 500 corporations, and the world’s best advertising agencies (Ogilvy). She is also a veteran public speaker and keynote presenter who talks about topics such as brand naming, category design, perceptual positioning, and nin-cliche-istic branding. She is the founder of FERAL, a strategic consultancy that specializes in untamed thinking and identity commercialization. Mara is not a guru and detests the word. Maybe as much as the dreaded “digital transformation”. But she sure knows how to transform lemons.

 

https://LinkedIn.com/in/mararada

https://ThinkFeral.com

23 Aug 202394. Escape the Startup Paradox Strategies for Funding Product Development00:25:23

Escape the Startup Paradox 😬 MVP Without VC

Can’t Build Your Product Without Funding

But Can’t Get Funding Without a Product

 

In the newest episode of Feel the Boot, we're diving headfirst into the world of product development sans angel investment.

I provide strategies for startups to navigate the challenges of raising funding pre-MVP.

Consider the paradox that most startups face: they need money to build their product, but struggle to obtain funding without a product.

I lay out three strategies to overcome this challenge.

The first is to build a cheaper version of the product by using off-the-shelf tools and proving its success.

The second strategy is to validate the business by conducting interviews, surveys, and gathering evidence of customer interest.

The third strategy is to explore alternative funding sources beyond traditional equity investors like: friends and family, grants, partnerships, or bootstrapping.

By following one or more of these strategies, you can find alternative ways to build your minimum viable product (MVP), enabling you to progress towards your business objectives.

 

Read this as an article: https://ftb.bz/94B

Watch the Video: https://ftb.bz/94V

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Get Advice for Your Startup: https://ftb.bz/Advising

07 Sep 202395. You’re delivering your pitch deck ask wrong What you should say instead 00:08:13

You’re delivering your pitch deck ask slide wrong! What you should say instead.

Learn the right and wrong thing to ask for.

How to handle hard questions during your ask.

 

I was listening to several founders deliver their pitches. Most of them did their “ask” wrong and seriously damaged their chances of success.

In this episode, look at their mistakes and how they could improve this critical step in their pitches.

You need to understand the whole angel and VC investment process. You pitch to get the next meeting, not for an immediate investment in your startup.

 

Read this as an article: https://ftb.bz/95B

Watch the video: https://ftb.bz/95V

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Get Advice for Your Startup: https://ftb.bz/Advising

25 Sep 202396. Startup Privacy Policies What you need to know about GDPR, CCPA and beyond!00:45:03

Startup Privacy Policies 🥷 What you need to know about GDPR, CCPA and beyond!

In this interview, Sabir Ibrahim, an attorney and entrepreneur, provides valuable insights on the implications of privacy and privacy policies for startups.

He emphasizes the importance of privacy laws, particularly highlighting the General Data Protection Regulation (GDPR) and the California Consumer Privacy Act (CCPA), and explains that these laws apply to all companies, regardless of their size.

Sabir advises startups to prioritize privacy policies, starting with a comprehensive privacy policy that includes information about data collection, usage, and sharing.

He also recommends engaging an attorney to ensure compliance with relevant regulations.

Sabir highlights the potential risks and consequences of non-compliance with privacy laws, such as regulatory enforcement actions and lawsuits.

He suggests implementing a plan for data privacy as companies grow, including the concept of privacy by design.

 

The discussion also explores the relevance of privacy issues in specific sectors, such as Medtech, Fintech, and AI applications, mentioning the need to consider industry-specific regulations.

The interview concludes by emphasizing the importance of engaging legal counsel, budgeting for legal expenses related to privacy policy creation and compliance, and treating privacy compliance as an investment rather than a cost.

 

Read this as an article https://ftb.bz/96B

Watch the Video https://ftb.bz/96V

Subscribe to Boot Prints https://ftb.bz/Join

Get personal advising https://ftb.bz/advising  

 

00:00 Introduction to Sabir Ibrahim

02:24 Evolution of privacy laws and regulations

04:43 Implications of privacy laws for startups

07:14 FTC enforcement actions on smaller companies

08:08 Importance of starting with a privacy policy

08:58 Key elements of a privacy policy

11:15 Considerations for international users and GDPR

14:22 Key data privacy laws to be aware of: GDPR and CCPA

17:54 Planning operations to ensure compliance

19:28 Privacy by design and value proposition

23:43 Privacy concerns in specific verticals

25:54 My Health, My Data Act and regulatory gaps

32:22 Cost considerations for early-stage startups

37:48 Privacy compliance on a limited budget

38:34 Avoiding conflicts in privacy-related terms

 

Sabir Ibrahim’s Bio:

During his 15-year career as an attorney and technology entrepreneur, Sabir has advised clients ranging from pre-seed startups to Fortune 50 companies on a variety of issues within the intersection of law and technology. He is a former associate at the law firm of Greenberg Traurig, a former corporate counsel at Amazon, and a former senior counsel at Roku. He also founded and managed an IT managed services provider that served professional services firms in California, Oregon, and Texas.

 

Sabir received his BSE in Computer Science from the University of Michigan College of Engineering. He received his JD from the University of Michigan Law School, where he was an article editor of the Michigan Telecommunications & Technology Law Review.

 

Sabir is licensed to practice in California and before the USPTO. He is a Certified Information Privacy Professional.

 

His website is: https://www.optimedge.legal

You can also find him at:

https://linkedin.com/in/sabir-ibrahim-a9505b1

https://medium.com/@optimedgelegal

https://youtube.com/@optimedgelegal

https://tiktok.com/@optimedgelegal

https://instagram.com/optimedgelegal

25 Oct 202397. Exposing the top reasons for angel investment pre-screen rejections00:18:42

🤯 Exposing the top reasons for fast angel investment rejections

Investors only take a few seconds to decide if a startup is worth a serious look.

These eight factors lead to most of the fast NOs ☠️

 

In this episode, I discuss the screening process for companies seeking funding from angels and VC.

Out of over a hundred applicants to my angel group, we only select about 20 for detailed consideration.

We drop the rest after only a few moments' consideration.

A handful of reasons dominate why investors eliminate companies in under a minute.

If you can avoid those traps, you can force investors to take the time to understand your startup.

At worst, you will get feedback to improve your business and your pitch.

At best, you will get the funding you need to grow.

 

Read this as an article https://ftb.bz/97B

Watch the Video https://ftb.bz/97V

Get advising for your startup https://ftb.bz/Advising

Subscribe to Boot Prints https://ftb.bz/Join

 

Check out the whole Fundraising Playlist https://www.youtube.com/playlist?list=PLgMU_ie96T-LoIvSK3hHFF0AmySuQjbKe

Watch the video on valuation methodologies https://ftb.bz/66V

16 Nov 202398. Startup Fundraising Facilitators Surviving the Pit of Serpents!00:20:09

Startup Fundraising Facilitators 🐍 Surviving the Pit of Serpents!

You might want to ask for help when you need to raise capital.

Take care, most of those people are useless or actively harmful.

 

 

Quoth the AI describing this episode:

In this episode, Lance Cottrell, an experienced startup advisor, shares insights on the challenges of fundraising, focusing on the role of fundraising facilitators in the process. He offers a candid look at the pitfalls of working with unskilled or unethical fundraisers. The episode provides crucial pointers about operational red flags and underlines the importance of maintaining realistic valuations. Additionally, it explains the logistics of fee models and advises on how successful fundraising can be approached. Moreover, it includes a brief discussion on the regulations surrounding fundraising and the need for facilitators to be registered. The episode concludes with advice on selecting the correct people to work with and setting adequate standards for partners.

 

Read the article: https://ftb.bz/98B

Watch the Video: https://ftb.bz/98V

 

The episode on the Startup Fundraising Paradox: https://ftb.bz/94B

06 Dec 202399. The 10x rule Why better is not enough00:07:25

The 10x rule 🌟 Why better is not enough

Having a superior solution is not good enough.

The special barriers startups face force you to build at least ten times better products.

 

Why Your Startup Needs to Be 10x Better

 

In this episode of 'Feel the Boot', host Lance Cottrell breaks down why startups need to be substantially better than their competition, particularly in the B2B context.

He explains the elements such as the high cost of switching, the immaturity of a startup product, and the typical risk of a startup failing, that force a startup to deliver a solution ten times better than the competitors.

 

Read the article https://ftb.bz/99B

Watch the video https://ftb.bz/99V

 

See the rest of the Founder Insights https://ftb.bz/Insight

 

Schedule advising with Lance https://ftb.bz/advising

03 Jan 2024100. Recognizing and Surviving a Startup Heart Attack 00:21:02

In this milestone episode, host Lance Cottrell dives deep into several critical topics inspired by his recent heart attack. First, he compares a heart attack with a financial crisis in a startup, emphasizing the need for recognizing early warning signs and taking immediate actions. He discusses how to identify critical situations where your venture is at risk and how to handle them effectively while sharing his personal experiences with his own startup. Then, he talks about the need to reassess one's priorities and the importance of aligning personal goals with the way we spend our time. He urges all founders to question their inherited societal goals and reflect on their passions. Lastly, as a public service announcement, he shares early warning signs for heart attacks and strokes, drawing parallels between them and potential dangers facing startups. He ends by stressing the urgency of immediate medical attention and action in such health crises.

 

Read as an article https://ftb.bz/100B

Watch the video https://ftb.bz/100V

Schedule advising with Lance https://ftb.bz/Advising

 

US Government Subsidized Health Insurance https://www.healthcare.gov/

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