The Startup CEO Show (Mark MacLeod)

Unlock unparalleled wisdom on leadership and innovation!

🚀 SUBSCRIBE TO THE STARTUP CEO SHOW NEWSLETTER: https://markmacleod.me/newsletter/

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Transform your meeting productivity with Fellow, the ultimate AI Meeting Assistant. Fellow transcribes, summarizes, and optimizes your meeting workflow, seamlessly integrating with your calendar and productivity tools.

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In this riveting episode of The Startup CEO Show, host Mark MacLeod dives deep with Tobi Lütke, CEO and Co-Founder of Shopify.

Together, they navigate the complexities of constant self-improvement, the philosophy of infinite games, and the critical importance of learning loops. Tobi shares his journey from startup founder to CEO, the vital role of motorsport in his life, and his unorthodox perspectives on business excellence and personal contentment.

Prepare to revolutionize your approach to leadership with Tobi's unique insights on balancing burnout, fostering a winning culture, and pursuing ambition beyond comfort zones.

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Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on Twitter: https://twitter.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

In this episode of the Startup CEO Show we're diving deep with Drew Green, the visionary CEO of Indochino, a transformative men's fashion brand known for their custom suits. Drew unpacks their unique strategies—like extending payment terms and adopting an appointment-based retail model—and shares invaluable insights on cash flow management, strategic partnerships, and leveraging media and CRM tools for efficient customer engagement.

We'll also explore how Indochino navigated the tumultuous landscape of the COVID-19 pandemic, strategically expanded their retail footprint, and tapped into the wedding market, which now represents a significant portion of their business.

Stick around for an enlightening conversation about resilience, innovation, and staying ahead in the competitive world of custom apparel.

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How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking ground-breaking insights on startup growth and leadership excellence?

🚀 SUBSCRIBE to Mark MacLeod's newsletter for exclusive tips and updates: https://markmacleod.me/newsletter/

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Ever thought, "This meeting could be an email"? We've got you covered!

Meet Fellow: The AI Meeting Assistant that transforms your meetings by connecting to your calendar and productivity tools. Transcribe, summarize, and centralize your meetings like never before!

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Join host Mark MacLeod as he dives deep with Rob Khazzam, CEO of Float, in an unmissable conversation about redefining finance, navigating the fintech landscape, and leading high-growth startups.

Rob shares his journey from Uber to fintech innovation, emphasizing the blend of intense execution and strategic foresight required for sustainable growth. Learn about best practices for hiring, building resilient teams, and leveraging financial strategies for long-term success. Plus, Rob offers a candid look at the Canadian market's potential and challenges, bringing you unmatched insights into fintech's future.

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Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on Twitter: https://twitter.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this special episode of The Startup CEO Show, host Mark MacLeod shares his extensive experience with venture-backed startup CEOs and discusses strategies to help CEOs lead their companies effectively without burning out.

Mark dives into the importance of prioritizing health, fitness, mindset, and human connections, introducing frameworks such as the "CEO perpetual growth loop" and the "five factors of health" from Ben Bergeron. He also emphasizes the significance of living with intention and creating boundaries to ensure long-lasting leadership and satisfaction in life.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Looking for the best Startup CEO insights?

SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

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In this episode, Mark MacLeod sits with Stephany Lapierre, the founder and CEO of Tealbook, as she recounts her journey from a background in consulting to becoming a trailblazing female founder in the tech industry.

They explore the evolution of Tealbook, emphasizing the importance of using feedback to drive decisions, the challenges of scaling technology, and the unique difficulties she faced as a solo female founder. The conversation also delves into the crucial support systems for women-led technology companies and the importance of community in fostering startup growth. This episode is a must-listen for anyone interested in the highs and lows of startup leadership, especially from the perspective of a resilient entrepreneur working to bridge gender gaps in the tech industry.

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Key moments:

00:00 Introduction to Stephany Lapierre and Tealbook.

04:15 Discussing the transition from consulting to tech startup.

09:22 The role of feedback in decision making.

12:37 Challenges in scaling and technology development.

17:45 The support from Fresh Founders and Stand Up Ventures.

22:30 Gender challenges in the startup ecosystem.

27:00 Insights into hiring and building a company culture.

31:55 How the COVID-19 pandemic influenced business operations.

38:10 Navigating underfunding and technology scalability.

43:03 The importance of staying informed and understanding technology.

48:15 Final thoughts on leadership and future aspirations.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Welcome back to the Startup CEO Show with Mark MacLeod. In this episode, we dive deep with Jason Smith, CEO of Klue, into the gritty details of building and leading a tech company in the Competitive Enablement space.

Connect with his story as we unravel the nuanced strategies of convincing C-suite executives of your product's value, the science of proving ROI through innovative attribution models, and the brave new world of AI's integration in business operations.

Whether you're a startup CEO, a product marketer, or just someone passionate about the intersection of technology, leadership, and growth, this is an episode packed with wisdom you won't want to miss. So plug in and get ready to take notes - this is Startup CEO Show.

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Key moments:

00:00 - 04:21 How AI is facilitating the transition from raw intel to insight.

04:22 - 08:48 Networking and promoting innovative thinkers for change.

08:50 - 14:01 In a world with competitive radar, investors see potential.

15:35 - 19:01 Comparing sellers' adoption of clue for sales.

19:21 - 22:00 Focusing on building culture and customer satisfaction.

22:08 - 24:40 Productivity at home, missing human connection.

24:43 - 29:50 Leaders learn from mistakes, delegate for growth.

30:00 - 33:01 Experience navigating VC world during COVID challenges.

33:10 - 36:10 Harnessing competitor data, leveraging AI for insight.

36:14 - 38:01 Platform insight still needed for specific competitive edge.

41:11 - 45:01 CEO key advices on managing and growing a SaaS company

45:02 - 48:15 Balancing work and family life with focus.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Scot Chisholm to discuss the multifaceted journey of growing a startup and driving market penetration.

Scot, the CEO and co-founder of Classy, delves deep into topics like forming strategic partnerships with heavyweights like Salesforce, navigating the complexities of fundraising from individuals to institutional investors, and the challenges associated with scaling from SMB to an enterprise-level organization. Scot also reflects on the evolution of Classy and its eventual acquisition by GoFundMe, sharing key insights that all startup CEOs can learn from.

Learn More at https://scotchisholm.com/

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Looking to master the art of startup leadership and ace your CEO role? You're in the right place! 😎

🔗 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER FOR EXCLUSIVE INSIGHTS: https://markmacleod.me/newsletter/

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Exhausted by endless meetings? Feel like some could be just emails?

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In this must-watch episode of The Startup CEO Show, Mark MacLeod interviews Mikael Cho, CEO of Unsplash, as they unravel the mysteries of startup success.

Mikael dives into the roller-coaster ride of Unsplash's journey, sharing hard-earned wisdom on overcoming challenges, iterating quickly, and managing cap tables. Get inspired by tales of skyrocketing growth, strategic acquisitions, and the art of aligning investor expectations. Mikael also sheds light on balancing work and personal life, all while keeping the entrepreneurial flame burning bright. 🔥

Don't miss out on expert strategies for optimizing your startup adventure!

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Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on Twitter: https://twitter.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How often do you think about improving your company's culture and efficiency?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/

and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Cameron Wenaus, the co-founder and CEO of Retreat Guru, to discuss building trust within a company, embracing emotional sharing, and integrating mindfulness into business practices.

Cameron dives into the importance of personal check-ins in leadership meetings, the impact of feeling safe in a work environment, and shares various resources and methods for beginning mindfulness meditation. The conversation also explores the challenges of managing resource limitations, the value of mission-aligned stakeholders, and how spiritual growth intersects with running a startup.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In today's episode of the Startup CEO Show, we dive into the incredible journey of Cody Ruberto, the founder and CEO of Uride. Mark MacLeod sits down with Cody to explore how he overcame financial obstacles early in his startup journey, leveraging angel investment and creative problem-solving to build a successful rideshare company. Cody shares revealing insights on expanding Uride into underserved markets, the importance of staying close to customers, and navigating the challenges of competition and market dynamics.

We'll hear how Cody's athletic background in soccer laid the foundation for resilience and leadership, and how he channels continuous learning and self-improvement into driving business success. From battling aggressive competitors to establishing ethical business practices, Cody's story is one of perseverance, innovation, and a relentless drive to make a global impact. Don't miss this episode as we uncover the strategies, challenges, and inspiring journey behind Uride's mission to solve transportation issues in small towns and cities around the world.

Tune in, subscribe, and prepare to be motivated by Cody Ruberto’s remarkable entrepreneurial expedition!

------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------

Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on Twitter: https://twitter.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

Welcome to the Startup CEO Show, where we dive deep into the heart of startup leadership and growth. In this episode, join our host Mark MacLeod as he engages on a thrilling conversation with Notch's CEO, Jordan Huck, regarding the critical decisions and pivots that shape a startup's journey.

We will explore the dynamic world startup leaders navigate daily and take a closer look at the challenges faced by companies as they brave new markets. We'll also focus on the relevance of sales and venture capital savvy in the Canadian startup scene.

From discussing the emotional rollercoaster of passionate leadership to the cutthroat venture capital markets, we tackle the nuances of growth, value alignment, and the crucial need for personal growth outside one's comfort zone.

Get ready to aprehend valuable lessons from a resilient startup CEO! And don't forget to subscribe for more insightful episodes like this.

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Chapters:

00:00 - 8:50 How to face challenging times while building a startup

09:00 - 18:00 Honest journey, relationship building, finance automation.

18:33 - 30:00 Adaptation is vital for business survival.

30:09 - 45:00 Raising venture capital fuels growth.

46:20 - 48:00 Challenges drive success, belief in ethical leadership.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, host Mark MacLeod sits down with David Cancel, a five-time founder and tech industry veteran, to explore the secrets behind building successful startups.

David shares invaluable insights from his experiences founding companies like Performable and Drift, as well as his pivotal role at HubSpot. The conversation delves into David's decision to sell Performable to HubSpot, a move that transformed both companies. David reveals how he rebuilt HubSpot's engineering team from the ground up while simultaneously scaling the business towards an IPO - a feat he likens to "changing a plane engine mid-flight." Listeners will gain a rare glimpse into the strategic thinking and bold decision-making that propelled HubSpot to its current $36 billion valuation.

The episode also covers David's journey with Drift, exploring how he identified a massive opportunity in conversational marketing and built one of the fastest-growing SaaS companies in history. David offers candid reflections on work-life balance, the challenges of entrepreneurship, and the importance of continuous learning.

Don't miss out on these hard-earned lessons from one of tech's most accomplished leaders - tune in now!

In this episode of The Startup CEO Show, host Mark MacLeod interviews Mike Katchen, Co-founder and CEO of Wealthsimple. Discover how Wealthsimple has transitioned from a single-product company to a multi-product leader in financial services.

Listen in for tips on maintaining control, leadership strategies, working within regulatory frameworks, and evolving with client needs. Plus, learn how Mike's personal growth, fitness routines, and mental health strategies contribute to his effective leadership.

Join us for an episode filled with practical advice and inspiring stories from one of Canada's top startup leaders!

------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, Mark MacLeod sits down with Joanna Griffiths, the visionary founder and CEO of Knix, a revolutionary women's clothing brand. Joanna shares her remarkable journey of building Knix from its inception in 2013 to becoming a major player in the intimate apparel industry.

She discusses how she identified a gap in the market for leak-proof underwear and turned it into a thriving business that has expanded into bras, activewear, and swimwear. Joanna provides fascinating insights into the challenges of being a female founder in a male-dominated industry, including her experiences pitching to investors who often struggled to understand her product. She also reveals how she navigated fundraising while pregnant with twins and closed a round just days before giving birth.

Listeners will be inspired by Joanna's determination, innovative approach to product development, and commitment to creating a brand that truly serves women's needs.

Don't miss this opportunity to learn from one of the most successful female founders in the direct-to-consumer space - tune in now!

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Join Mark MacLeod on his new podcast talking to some of the most venture backed successful CEOs.

In this new episode, our host Mark MacLeod sits down with Robbie Bent, the visionary co-founder and CEO of Othership, a transformative space that combines sauna, ice baths, breathwork, sound, and community to redefine wellness in urban settings. 

Bent's innovative approach to tackling loneliness and fostering genuine connections in major cities through unique physical experiences is nothing short of revolutionary.

Robbie Bent's story is not your average entrepreneurial tale. With a background marked by personal challenges, including a battle with substance abuse, Bent's mission with Othership is deeply personal. 

His commitment to creating a healthy, inclusive space where individuals can meet, heal, and grow together is the foundation of Othership's rapid growth trajectory. Bent's insights into the power of community, health, and wellness as tools for transformation are both inspiring and instructive.

Don't forget to subscribe for more insightful episodes like this.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

We’re thrilled to bring you an insightful conversation with Mark Ang, the co-founder and CEO of Gobolt, a revolutionary logistics company transforming the way we think about delivery and sustainability. 

Mark's journey from a university side hustle to leading a major player in the logistics industry is nothing short of inspiring.

Mark was recognized on the Forbes 30 Under 30 list, and he shares his unique perspective on scaling a business, the importance of sustainability in logistics, and the challenges of navigating the startup world. Gobolt, initially a summer storage solution for students, has evolved into a sustainable logistics powerhouse under Mark's leadership, emphasizing the critical role of adaptability and vision in entrepreneurship.

Don't forget to subscribe for more insightful episodes like this.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Welcome to the Startup CEO Show, where we delve into the strategies and insights of successful entrepreneurs. In this episode, our host Mark MacLeod sits down with Ben Jabbawy, the mastermind behind Privy's remarkable journey to a $120 million exit. 

Ben Jabbawy is the co-founder and former CEO of Privy, a marketing automation platform that scaled phenomenally within the Shopify ecosystem. Starting from his parents' house, Ben grew Privy to 80 employees and $10 million in ARR, culminating in a $120 million exit in 2021. His insightful approach to market timing, distribution strategies, and capital efficiency has set a benchmark in the SaaS industry. Ben is now an active investor, sharing his wealth of experience with emerging entrepreneurs.

Don't forget to subscribe for more insightful episodes like this. Drop your thoughts and questions in the comments below!

Join the leading newsletter designed exclusively for the CEOs of high-growth startups and the VCs who back them.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Sean Kelly to discuss the importance of founder well-being and its impact on business performance.

Sean, the founder of Family Fund, explores crucial topics such as treating founders like elite athletes, avoiding the pitfalls of hustle culture, and the significance of health, wealth, and freedom for entrepreneurs. Learn about the essential steps for maintaining mental clarity, fostering continuous learning, and strategic growth in consumer brands. Sean also shares his approach to investment and community building, along with insightful examples from his extensive experience in the health and wellness space. Don’t miss this conversation packed with strategies to optimize your business and personal success.

_______________________________

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

How many times a day do you think "This meeting could have been an e-mail"?

----------------------------------------------------------

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod engages in a deep discussion with Greg Smith, co-founder and CEO of Thinkific. Learn from Greg's experience as he navigated the transition from a securities lawyer to becoming the leader of a cutting-edge SaaS platform.

Greg provides key takeaways on establishing a single source of truth, building a content engine, and the strategic value of acquiring profitable customer annuities. He also shares insights on the evolution of Thinkific, its roadmap, and future visions involving augmented reality and AI.

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Key highlights:

03:45 Establishing a Single Source of Truth

08:10 Building a Strong Content Engine from the Start

12:50 Strategic Value of Profitable Customer Annuities

18:30 Importance of Capital Efficiency in SaaS Businesses

24:20 Transitioning from Roadmap Control to Outcome Achievement

30:40 Impact of AI and Augmented Reality on Content Sharing

36:15 Combining Career Content with Community Platforms

42:00 Benefits of a Seamless Payments Platform on Customer Lifetime Value (LTV)

49:30 Balancing High-Level Management with Deep Dive Projects

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod engages in a thought-provoking dialogue with Michael Litt, the innovative CEO of Vidyard and investor at Garage Capital. Discover the secrets behind transforming startups into scale-ups, insights of being part of Y Combinator in Silicon Valley, and navigating the ever-evolving tech landscape.

Explore Michael's perspective on staying innovative and energized, the nexus between investing and entrepreneurship, and the pivotal role of bleeding-edge technology in shaping the future of businesses.

-------------------------

Key highlights:

04:15 The Genesis of Vidyard and Entrepreneurial Journey

08:30 Unleashing the Potential of AI in B2B Commerce

12:45 Crafting Sustainable Growth Strategies

18:20 Revolutionizing Customer Interactions with AI Avatars

24:10 Building a Strong Executive Leadership Team

30:50 Leveraging AI for Enhanced Customer Outreach

37:30 The Impact of University of Waterloo on Startup Ecosystem

42:15 Founder CEO vs. Professional CEO Insights

48:40 Navigating the Startup Landscape and Building Success

-----------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Andrew Gazdecki, to discuss the intricacies of startup acquisitions and building market value.

Andrew, the CEO of acquire.com, delves into crucial topics such as building trust with buyers, preparing your business for sale, and the importance of being diligence ready. Learn how to streamline the acquisition process with data rooms, templates, and financial recasting. Andrew also shares his experiences and insights on bootstrapping SaaS businesses, navigating private equity markets, and leveraging strong brand narratives for maximum impact.

-----------------------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Katherine Regnier, founder and CEO of Coconut Software, for an insightful discussion on growing a business while staying true to your values.

Discover Katherine's thoughts on raising funds, focusing the company's direction, and prioritizing customer perspectives while navigating sales cycles in the financial sector. Tune in to understand how flexible work policies impact productivity and employee satisfaction, and gain wisdom on transitioning from founder to CEO.

--------------------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, Mark MacLeod welcomes Glen Coates, former CEO of Handshake and current VP of Product for Core at Shopify. Glen takes listeners on a journey through his entrepreneurial experiences, from founding Handshake to his current role at Shopify.

He shares candid insights about the challenges of building a B2B e-commerce platform, including the complexities of serving businesses with thin margins and intricate needs. Glen's transition to Shopify provides a unique perspective on what makes the company a magnet for talented founders. He offers fascinating glimpses into Shopify's culture of innovation, driven by CEO Tobi Lütke's relentless pursuit of cutting-edge technology.

The conversation takes an exciting turn as Glen discusses the rapid advancements in AI and their potential impact on e-commerce. He shares intriguing examples of how Shopify is integrating AI into its platform, including a multilingual AI assistant that's revolutionizing customer support. The discussion also touches on the evolving landscape of AI and its implications for businesses of all sizes.

Don't miss out on these invaluable insights - listen now and gain a competitive edge in the rapidly evolving world of e-commerce and technology.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Jason Fried, co-founder and CEO of 37signals, for an enriching conversation on startup leadership and maintaining a successful business partnership.

Jason shares valuable insights on keeping business costs lean, the inefficiencies of large teams, and the necessity of balancing intuition with business decisions. Learn how Jason's unique approach to day-to-day operations and his "joy of missing out" mindset has contributed to 37signals' sustained success. Discover his thoughts on remaining independent, the pitfalls of excessive venture capital, and the importance of genuine personal branding.

-------------------------

Key highlights:

02:20 The Power of Respect and Admiration in Business Partnerships

06:50 Why Large Teams in Software Companies Can Be Inefficient

12:15 The Importance of Keeping Costs Low and Avoiding Early Venture Capital

18:00 Balancing Fights with Positive Outcomes in Startup Success

24:45 Jason’s Approach to Vision: Focus on Present and Immediate Future

30:15 Embracing the 'Joy of Missing Out' (Jomo)

35:50 Allowing Space for Creativity and Reflection

41:35 The Importance of Consistent Practice and Personal Satisfaction

47:20 Seeking Advice and Peer Groups for CEOs

53:40 The Value of Balancing Profit with Reinvestment

59:30 Finding Enjoyment and Energy in Work Processes

--------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Steve Bajuvez, to uncover the power of customer support as a strategic advantage.

Steve, a former FreshBooks employee with 14 years of tenure, shares the transformative impact of spending time in support roles for new hires and how it shifts their perspective and understanding of the product. Discover the unique support strategies at FreshBooks, the importance of empathy and problem-solving in support roles, and how Steve led his team to foster a culture where every member could shine. Learn about the balance between creating memorable customer experiences and the "effortless experiment" aimed at reducing support calls by solving issues proactively.

---------------------------------------------

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

---------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this milestone 50th episode of The Startup CEO Show, host Mark MacLeod reflects on 25 key lessons from his 25 years in the startup world. Drawing from his extensive experience as a CFO, venture capitalist, and advisor, Mark shares invaluable insights on timing, market dynamics, fundraising, and leadership.

He emphasizes how timing and luck play a crucial role in startup success, citing examples like Tungle's fortunate Series A raise just before the 2008 financial crisis. MacLeod also delves into the challenges of operating in hot markets, the potential of disrupting established industries, and the pitfalls of poor market selection. He shares candid thoughts on the venture capital industry, board dynamics, and the importance of founder self-awareness.

Throughout the episode, Mark peppers in anecdotes from his work with successful companies like Shopify, providing listeners with a rich tapestry of startup wisdom.

Tune in to gain insights that could shape your entrepreneurial journey and potentially save you from costly mistakes.

----------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, Mark MacLeod engages in a deep and insightful conversation with Alison Taylor, co-founder and co-CEO of Jane App, a leading practice management and scheduling platform for healthcare clinics. Alison shares the remarkable journey of building Jane from a solution for her own healthcare practice to a thriving company with 600 employees and a global user base. Alison's unique perspective on growth, prioritizing customer and team satisfaction over rapid expansion at all costs, provides a refreshing alternative to the typical startup narrative.

The conversation delves into the intricacies of maintaining a successful co-founder relationship, with Alison and her partner Trevor sharing the CEO role. She emphasizes the importance of values alignment and having a shared vision for the company's future. Alison also provides valuable insights into the advantages and challenges of building a tech company in Canada, advocating for the strength of the Canadian startup ecosystem and the importance of contributing to its growth.

One of the most compelling aspects of the conversation is Alison's candid discussion of balancing the demands of running a fast-growing company with personal life. As a solo parent to three teenagers, she offers a unique perspective on the challenges faced by working parents, particularly women, in leadership roles. Alison provides thought-provoking insights into gender roles in the workplace and at home, emphasizing the need for true equality in both spheres.

Don't miss this opportunity to learn from one of Canada's most successful tech entrepreneurs - tune in to the Startup CEO Show with Mark McLeod and gain invaluable insights that could shape your own entrepreneurial journey.

-------------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

----------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

---------------

In this episode of The Startup CEO Show, host Mark MacLeod engages with Daniel Saks in an insightful discussion on leadership transitions and the future of AI in business.

Daniel, who navigated a successful transition from CEO to president and board member at AppDirect, talks about the importance of leadership changes for company growth. He shares his experiences with technology startups, the role of AI in enhancing business productivity, and his vision for agentic AI. Learn from Daniel's perspectives on building market value, overcoming industry challenges, and leveraging digital tools for optimal operational efficiency.

--------------------

Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on Twitter: https://twitter.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

Welcome back to the Startup CEO Show, where we delve into the minds and experiences of successful startup leaders! In today’s episode, we're joined by Aydin Mirzaee, CEO of Fellow.app, a company on a mission to make meetings more productive.

Tune in as Aydin shares his journey from bootstrapping his first startup to a stellar exit, and the shifts in his entrepreneurial approach since diving into the world of venture capital. Our host, Mark MacLeod, explores practical tips from Aydin on schedule management, energy audits, and embracing the unconventional. For an insightful blend of big-picture dreaming and operational tactics, this episode is a must-listen for every high-growth CEO out there!

And don't forget to subscribe for more insightful episodes like this!

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Are you seeking invaluable tips on becoming a successful startup CEO?

SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

----------------------------------------------

In this episode, Mark MacLeod gets into an engaging discussion with Hiten Shah, the co-founder and CEO of Nira, exploring the myriad facets of leading and funding a startup. Hiten shares his experiences and philosophies, ranging from the necessity of aligning product development with customer feedback to the intricacies of venture capital and self-funding.

Discover the profound insights on venture capital investment, the vital importance of investor-founder alignment, and Hiten's unique approach to product innovation and company culture. This episode is perfect for aspiring entrepreneurs and seasoned executives alike, who are eager to learn from someone who has walked the challenging path of startup success.

-------------------------

Key moments:

05:10 How to Build a Startup from Scratch

11:20 Advantages of Self-funding versus VC

14:45 The role of Investors

19:30 Strategies for Handling Risk and Investors

29:10 Remote Work and its Impact on Company Culture

32:40 Discussion on Customer Obsession

37:50 Challenges of raising money and the timing of investment pitches.

42:05 Understanding and Leveraging Investor Expectations.

47:00 Accountability in Remote Work and Transparency in Business.

----------------------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Dan Park, co-founder and CEO of Clutch, to discuss the rollercoaster journey of building Canada's leading online used car marketplace. Park shares the highs and lows of Clutch's growth, from rapid expansion fueled by venture capital to a near-death experience that forced massive layoffs. He offers a candid look at how Clutch weathered the storm, pivoted to profitability, and emerged stronger on the other side.

Park dives deep into Clutch's mission to disrupt the traditional used car buying experience in Canada by offering full transparency, reconditioning every vehicle, and allowing customers to complete the entire purchase online. He explains how Clutch's vertically integrated model and focus on customer experience sets it apart in an industry not known for trust or convenience. Listeners will gain valuable insights into building a venture-scale business in a mature market, balancing growth with unit economics, and staying motivated through extreme challenges.

The conversation also explores key lessons Park brought from his time leading Uber Eats Canada, including the importance of operational focus and rapid iteration. His perspective on fundraising cycles, investor expectations, and navigating macro headwinds will resonate with many founders.

Don't miss Park's inspiring story of turning setbacks into comebacks - tune in now to the Startup CEO Show.

--------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Want to receive the best Startup CEO Insights?

SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

------------------------------

In this episode of the Startup CEO Show, explore the power of long-term vision and work-life integration with our host Mark MacLeod and the inspiring Erin Bury, co-founder and CEO of the innovative estate planning platform, Willful.

Tune in as Erin sheds light on rejecting hustle culture, creating ease for families with online wills, and steering a startup alongside her spouse. Discover how Willful is simplifying end-of-life planning and Erin's unique approach to leading a consumer brand and fostering a startup that values both profitability and a balanced lifestyle.

Make sure to like, share, comment, and subscribe to stay updated with more fascinating episodes like this one from the Startup CEO Show!

-----------------------------------------

⏰Timestamps:

02:20 - 05:49: Rejecting "Hustle Porn" for Work-Life Balance

05:50 - 08:33: Willful's Origins and Market Disruption

08:34 - 12:05: Overcoming Investor Doubts

12:06 - 15:40: The Joys and Juggles of a Spouse-Run Startup

15:41 - 18:15: Erin's CEO Strategy: Hiring, Vision, and Financial Stability

18:16 - 22:10: Personal Time Management

22:11 - 26:00: The Willful Couple's Work-Life Blend

26:01 - 29:35: Startup Ecosystem as a Consumer Brand

29:36 - 33:08: The Canadian Startup Scene

33:09 - 36:45: Fostering a Sustainable Business

36:46 - 40:25: Young Parents and Elderly Individuals

40:26 - 43:10: Strategic Partnerships and Marketing in Estate Planning

43:11 - 46:55: Life, Legacy, and Running a Startup

46:56 - 50:26: The "Unicorn" Potential

50:27 - 55:00: Intentional Living and the Reality of Entrepreneurship

---------------------------------------------------------------------------

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/

and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Nicholas Reichenbach to discuss the journey of Flow Alkaline Spring Water, from its unique inception to becoming a public company.

Nicholas dives into key topics such as building strategic partnerships, the challenges of raising capital in Canada, and driving sustainable business practices. Learn how Flow distinguished itself in the competitive water market, the importance of long-term vision, and the role of serendipity and positive energy in startup success. Nicholas also shares his experiences with celebrity endorsements and the impact of maintaining strong entrepreneurial leadership.

------------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Matt Turck, General Partner at FirstMark Capital, for a wide-ranging discussion on venture capital, AI, and the startup ecosystem.

As the first VC guest on the show, Turck offers a unique perspective on board dynamics, content creation, and the evolution of the tech industry. He shares his experiences as an early AI investor and discusses the current state of enterprise AI adoption, highlighting the challenges and opportunities in the space.

Turck emphasizes the importance of founder quality and market timing in startup success, drawing on his years of experience backing unicorn companies. The conversation also touches on the global nature of tech innovation, with Turck expressing bullish sentiments on European entrepreneurship and the spread of Silicon Valley's model worldwide.

Tune in to hear Turck's thoughts on the future of SaaS, the AI revolution, and what it takes to build a successful startup in today's rapidly changing landscape.

-------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Looking for the best Startup CEO Insights?

SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

----------------------------------------------

In this episode, we’re joined by former Dribbble CEO, Zack Onisko, who shares his insightful experiences from leading one of the few remaining independently owned social networks designed specifically for designers.

Zack and host Mark MacLeod discuss his decision to step down, reflecting on a period of significant profitability and growth at Dribbble, achieved without the backing of venture capital. Making major career transitions, the impact of leadership on company culture, and the importance of aligning personal values with professional endeavors are some of the key topics of this episode. Join us for a compelling conversation that unveils the nuances of steering a tech enterprise through evolving landscapes and personal growth.

-------------------------

Key moments:

00:00 Leaving Dribbble due to personal pursuits.

05:42 Silicon Valley raised CEO reflects on growth.

06:48 Talking to investors, company grew, profitable results.

10:11 Technology has shifted startup landscape, lowering expenses.

13:54 Email crucial for user acquisition and revenue.

18:00 Transition from investment banker to coach amidst COVID.

20:58 Transition from employee to successful entrepreneur for freedom.

24:27 Self-driven urgency led to company's success.

28:01 Learning from Andrew's entrepreneurial and investment approach.

30:29 Transitioned from startup operator to capital management.

36:43 Reinvesting profits to fuel company growth and acquisitions.

40:52 Shifted managerial style, focused on building trust.

42:10 Remote work offers efficiency and productivity benefits.

46:58 Found your insights helpful, want to explore further.

50:28 Joining Dribbble was a dream come true, looking to pursuit new ones

-------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, host Mark MacLeod sits down with Tyler Denk, co-founder and CEO of Beehiiv, to explore the world of email marketing and the creator economy. Tyler shares the fascinating origin story of Beehiiv, which grew out of his experience building custom tools at Morning Brew. He explains how Beehiiv has become a leading all-in-one platform for creators and brands to grow their audience and monetize their content.

Tyler dives deep into Beehiiv's unique value proposition, combining website building, email newsletters, and monetization tools in one seamless platform. He discusses how this integrated approach sets Beehiiv apart from legacy email providers and allows creators to focus on what they do best. The conversation touches on the evolving role of AI in content creation, with Tyler offering nuanced insights on when AI can be helpful and when human creativity is irreplaceable.

One of the most compelling parts of the discussion centers on Tyler's leadership philosophy and operational strategies. He shares his commitment to radical transparency, describing how he writes detailed weekly emails to keep his team aligned and motivated. Tyler also reveals how Beehiiv raised its Series A in just six days and its Series B in two weeks, crediting his practice of sending comprehensive monthly investor updates. For aspiring founders and CEOs, this episode is a masterclass in building a high-growth startup with intention and focus. Don't miss Tyler's contrarian views on company size and his emphasis on deep work - tune in now to gain invaluable insights from one of tech's rising stars.

In this episode of the Startup CEO Show, host Mark MacLeod welcomes Dax Dasilva, the founder and CEO of Lightspeed Commerce, for a wide-ranging discussion on leadership, spirituality, and building a billion-dollar tech company. As Lightspeed celebrates its 20th anniversary, Dasilva reflects on the company's journey from a small team in Montreal's Gay Village to a global leader in commerce solutions. He shares how his personal growth, including his conversion to Judaism, has intertwined with Lightspeed's evolution, providing him with the spiritual foundation to navigate the challenges of scaling a tech company.

Dasilva offers unique perspectives on creating an inclusive workplace culture, emphasizing the importance of allowing employees to bring their authentic selves to work. The conversation delves into Lightspeed's funding journey, from bootstrapping to venture capital to going public, with Dasilva providing valuable insights on each stage. He also discusses the company's acquisition strategy and the complexities of integrating multiple platforms.

Dasilva opens up about his experiences with burnout and the importance of physical health in maintaining leadership stamina. The episode concludes with Dasilva explaining his decision to return as CEO and his vision for Lightspeed's future. This conversation is a goldmine of wisdom for entrepreneurs, offering a rare glimpse into the mind of a leader who has successfully balanced growth, innovation, and values over two decades.

Tune in now to gain invaluable insights from one of Canada's most successful tech entrepreneurs.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Mike Serbinis, a prolific tech entrepreneur with over $1 billion in exits under his belt. Mike shares his incredible journey from engineer to CEO, including competing against Amazon with his e-reader company Kobo and his current venture League, a healthcare technology platform with over 20 million users.

Dive into Mike's experiences in Silicon Valley, his approach to building and scaling companies, and how he's tackled immense challenges in the healthcare industry. Mike discusses the importance of going for "gold" in business, likening it to the Olympics where only the top performers are remembered. He also reveals his strategies for maintaining work-life balance while pursuing ambitious goals, including his weekly "Week Ahead" memos that have become a cornerstone of his leadership style.

Tune in now to learn from one of tech's most successful founders and gain actionable insights to apply to your own entrepreneurial journey.

--------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Welcome back to the Startup CEO Show! In this episode, we're diving into the inspiring journey of Kyle Braatz, founder and CEO of Fullscript. From competitive hockey to shaking up the healthcare industry, Kyle's path exemplifies the crossover between sports and entrepreneurship, highlighting the power of teamwork and competitive spirit.

We'll uncover the inner workings of building a billion-dollar company, Fullscript, which is revolutionizing whole person medicine by championing natural alternatives. Kyle shares the strategic choices that set Fullscript apart – shunning venture capital, focusing on a niche market, and prioritizing capital efficiency and organic growth.

Stay tuned as we skate through the highs and lows of startup growth, strategic investment decisions, and the qualities of empathetic leadership with Kyle Braatz. Whether you're a budding entrepreneur or an established CEO, you won't want to miss the wisdom Kyle drops on this episode of the Startup CEO Show.

Don't forget to subscribe for more insightful episodes like this.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod engages in a thought-provoking dialogue with Nick Francis, co-founder and CEO of Help Scout. Dive into Nick's pioneering journey of building a 100% remote company, leveraging intentional decision-making, and setting new standards for customer support excellence.

Nick shares his vision on the transformational impact of AI in customer service, the importance of company culture and values, and his personal commitments to both team and customer experiences. Learn how Help Scout navigated the challenging tech landscape while staying profitable and integrating first principles in their growth strategy.

-------------------------

Key highlights:

04:15 Founding Help Scout

08:30 Embracing and Excelling in a 100% Remote Work Environment

12:45 The Transformational Potential of AI in Customer Support

18:20 Aligning Fundraising Strategies with Core Values and Integrity

24:10 Whole Company Support and Onboarding Processes

30:50 The Importance of Self-Service Documentation in Customer Support

37:30 Achieving B Corp Status and Its Impact on Business

42:15 Stewardship of Capital and Long-term Thinking in Fundraising

48:40 Balancing Work-Life Harmony and Sustainable Leadership

-----------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Welcome to The Startup CEO Show with Mark MacLeod. In this episode we are diving into a truly enlightening conversation with none other than Chris Savage, the co-founder and CEO of Wistia.

This time, we unpack the deeply rooted values that have shaped Chris's company, emphasizing the importance of genuine connections, personal growth, and integrity in leadership.

We also explore into the importance of personal branding in today's social media landscape, with Chris explaining why CEOs should be building genuine profiles that resonate with their community.

So grab your favorite beverage and enjoy this in-depth episode. Don't forget to subscribe to learn the best advice from the best startup CEOs.

------------------------------------------------------

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Looking for expert insights on startup success and leadership strategies for CEOs?

🚀 Subscribe to Mark MacLeod's Newsletter: markmacleod.me/newsletter

------------------

Tired of meetings that should've been emails?

Fellow's AI Meeting Assistant is your solution—transcribing, summarizing, and streamlining your workflow by connecting with your calendar and productivity tools.

Enhance your productivity today: fellow.app

------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod interviews Russ Heddleston, former CEO of DocSend, to explore the nuances of startup acquisitions and creating market value. Russ shares his experience selling to Dropbox, navigating competition, and making strategic business decisions. Discover how building relationships with potential buyers and competitors can influence acquisition outcomes. Russ also discusses product-led growth, capital efficiency, and his new ventures focused on leveraging LLMs.

------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

----------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Mikita Mikado, co-founder and CEO of Pandadoc, to explore the journey of transforming a startup into a thriving business with over $100 million in revenue.

Gain inspiration from Mikita's reflections on his entrepreneurial mission, his commitment to paying it forward, and the impact of therapy and emotional health on his leadership journey.

--------------

Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on Twitter: https://twitter.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

In this new episode of “Startup CEO Show,” we talk with Jordan Boesch, the dynamic co-founder and CEO of 7shifts, a comprehensive HR and team management platform tailored for the hospitality industry. Dive into the world of startup growth, leadership transitions, and the undeniable impact of user feedback on product development.

Jordan Boesch's journey from a passionate developer to a visionary CEO is nothing short of inspiring. Hailing from Saskatoon, Jordan has scaled 7shifts from a nascent startup to a powerhouse with over 400 employees, all while maintaining a deep connection to product development and customer satisfaction. 

His unique approach to leadership, coupled with a relentless pursuit of excellence, makes this episode a must-watch for aspiring entrepreneurs and seasoned executives alike.

Don't forget to subscribe for more insightful episodes like this.

___________________

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

___________________

Connect with Jordan:

https://www.linkedin.com/in/jordan-boesch/

https://www.7shifts.com/

Setting the table: https://www.amazon.ca/Setting-Table-Transforming-Hospitality-Business/dp/0060742755/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=1706900857&sr=1-1

On this episode of The Startup CEO Show, Mark MacLeod and Amar Varma discuss everything from the role of artificial intelligence in business to navigating complex political climates -such as US election day- as a CEO.

Amar offers his expertise on creating sustainable growth, overcoming business hurdles, and building successful teams in today’s fast-paced world. Whether you’re looking to innovate in your field or adapt to new challenges, this episode is packed with actionable insights for leaders and entrepreneurs alike.

-------------------

Looking to elevate your leadership game with actionable strategies?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter

----------------------

Boost team productivity and streamline meetings with Fellow, the AI Meeting Assistant that transcribes, organizes, and integrates seamlessly with your calendar. Learn more: https://fellow.app/

-----------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Welcome to another episode of The Startup CEO Show!

This week, we have a special video edition featuring Joel Gascoigne, founder and CEO of Buffer, known for its revolutionary approach to transparency and remote work. Our host, Mark MacLeod, dives deep with Joel into the intricacies of managing a startup during times of growth and decline, the strategic changes that Buffer has embarked on, and the personal journey of leadership.

Joel shares his unique experience of managing 12 direct reports and transitioning to an asynchronous communication model to foster deep work and reduce meeting overload. He reflects on overcoming challenges, such as plateauing growth and navigating the pandemic's impacts with a renewed focus on supporting entrepreneurs and small businesses. We also explore the dynamics of co-founder relationships, raising and managing investor expectations, and Buffer’s return to a bootstrap model after a strategic VC buyout.

Joel's insights into the long-term strategic vision, maintaining company culture, and embracing transparency offer invaluable lessons for startup CEOs and leaders striving to sustain growth while preserving core values. Plus, we touch on how fatherhood has influenced Joel's productivity and work-life balance.

Tune in to glean actionable strategies for managing your startup more effectively and authentically.

------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------

Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on X: https://x.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Josh Reeves, Co-founder and CEO of Gusto, to discuss Gusto’s values-driven approach, the intricacies of scaling an SMB, and the long-term vision for Gusto.

Josh delves into critical topics such as Gusto's UI simplicity, building a warm customer experience, and maintaining company culture. He shares his unique leadership style, the importance of aligning values in hiring, and how he promotes a culture of kindness and honest feedback at Gusto.

------------------------------------------------------

Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Stay updated on X: https://twitter.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/

Seeking the best startup and leadership advice tailored for CEOs?

SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

----------------------------------------------

Are you curious about the journey of raising over $400 million in capital and navigating the path from startup to IPO? Tune in for this enlightening conversation!

In this episode, host Mark MacLeod delves deep with Jack Newton, the co-founder and CEO of Clio, to explore the multi-faceted aspects of leading a legal tech company. Jack shares the inspiring story of Clio's origin, the pivotal moments in their fundraising journey, and the strategic decisions that led them to become a market leader.

Discover insights into how Jack and his co-founder Ryan balanced their roles, the crucial importance of continuous learning, and how surrounding oneself with experienced team members can propel a company forward.

-------------------------

Key moments:

04:15 The Origin Story of Clio

08:30 Importance of Product and Technology Expertise

11:45 Securing First Institutional Angel Funding

19:20 Growth Stage Power Dynamics

25:50 Transitioning from Venture to Private Equity

33:05 Choosing the Right Partners for Growth

40:50 Vertical SaaS and Customer Retention

46:30 Preparing for an IPO and Future Growth

-----------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

-----------------------------------------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

----------------------------------------------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Mark Faggiano, former co-founder and CEO of Taxjar, to discuss the journey from startup to successful acquisition and his current dedication to the Cure Alzheimer's fund.

Mark Faggiano shares insights on navigating the e-commerce tax compliance landscape, fostering strong co-founder relationships, and making customer-centric decisions that drive growth. He also delves into the importance of profitability, independent control, and effective remote work strategies. Additionally, Faggiano talks about his commitment to Alzheimer’s research and ways to mitigate the risk of the disease through lifestyle choices.

----------------------------------------------

Connect with Mark Faggiano: https://www.linkedin.com/in/markfaggiano/

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?

🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

--------------

How many times a day do you think "This meeting could have been an e-mail"?

Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.

Go to https://fellow.app/ and discover the best way to enhance productivity today!

-----------

In this episode of The Startup CEO Show, host Mark MacLeod sits down with David Hauser to discuss optimizing routines, building processes, and achieving startup success.

David, a multi-time founder, angel investor, and author, delves into crucial topics such as the importance of morning routines, building a high-performing team, integrating values into company culture, and sending regular updates as a predictor of entrepreneurial success. Learn how to apply discipline and data-driven marketing across various industries, as well as insights into bootstrapping versus raising venture capital.

----------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

The latest episode of the Startup CEO Show features an enlightening conversation with Nick Franklin, the visionary behind ChartMogul, a leading subscription analytics platform. Mark McLeod explores ChartMogul's evolution from a niche product to a comprehensive platform for B2B SaaS companies. Nick shares fascinating insights into the state of SaaS metrics, revealing that while core metrics like MRR and churn remain crucial, the rise of AI and metered billing is reshaping the landscape.

The discussion touches on ChartMogul's unique position as a barometer for the SaaS industry, offering listeners a rare glimpse into industry-wide trends and benchmarks. Nick's journey from an illustration background to becoming a successful tech CEO is both inspiring and instructive, highlighting the importance of adaptability and continuous learning in the startup world.

The episode also dives into the challenges of remote work, with ChartMogul embracing a distributed model long before it became mainstream. Listeners will appreciate Nick's candid reflections on the pros and cons of venture funding, and his decision to prioritize profitability over rapid, unsustainable growth. Don't miss this opportunity to learn from one of the industry's most experienced and thoughtful leaders.

--------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, join Mark MacLeod and Elizabeth Caley for an insightful discussion with Elizabeth Caley, co-founder and CEO of Poppy. Learn how Poppy is revolutionizing indoor air quality with cutting-edge technology and bold leadership.

Gain strategic insights as Elizabeth shares her journey from corporate to startup life, navigating product development, and embracing the chaos of entrepreneurship. Discover the power of clear communication, remote work culture hacks, and the magic of co-founder synergy.

Don't forget to like, share, comment and subscribe for more insightful episodes like this!

-----------------------------------------

⏰Timestamps:

04:33 - 07:01: How the Pandemics Shifted Businessess

07:01 - 11:11: Strategic Moves: Meta.com Acquisition

11:11 - 14:54: Startup Success: Pandemic Agility

14:54 - 18:55: Energy Efficiency: HVAC Optimization

20:06 - 25:20: Seamless Transition to Remote Work

25:20 - 28:01: Collaboration & Resilience

28:01 - 31:50: CEO's Time Management: Maximizing Availability

31:50 - 36:24: Inclusive Leadership: Empowering Sales

38:06 - 42:34: Embracing Change: COO to CEO

42:34 - 45:24: Career Evolution: Shedding Norms

45:24 - 49:02: Diverse Journey: Consulting to Product Leadership

---------------------------------------------------------------------------

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this captivating episode of the Startup CEO Show, Mark MacLeod sits down with Clive Kinross, the CEO of Propel Holdings, a company that's revolutionizing lending for underserved consumers. Clive shares his remarkable journey from South African chartered accountant to successful entrepreneur, detailing the founding and growth of Propel Holdings. With over a million customers served and $2 billion in loan originations, Propel has become a game-changer in the financial industry.

Clive discusses the company's innovative use of AI in credit assessment, allowing them to serve customers traditional banks often overlook. He emphasizes the importance of profitability, team loyalty, and maintaining a long-term perspective in business growth. Listeners will gain valuable insights into building a successful fintech company, navigating the challenges of going public, and maintaining a strong company culture through rapid growth.

Clive's story is a masterclass in entrepreneurship, demonstrating how a background in accounting can be leveraged to create a thriving business. Don't miss this opportunity to learn from one of the most successful CEOs in the fintech space – tune in now!

--------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

This episode of the Startup CEO Show delves deep into the world of sustainable business practices and corporate responsibility with Stuart Lombard, the visionary behind Ecobee. Mark MacLeod guides the conversation through Lombard's philosophy on building a company that not only succeeds financially but also makes a positive impact on the world.

Lombard shares compelling examples of how Ecobee integrated sustainability into its core business model, from reducing packaging and optimizing shipping methods to negotiating better payment terms with suppliers. He explains how these practices not only reduced the company's environmental footprint but also improved its bottom line, challenging the notion that sustainability always comes at a cost.

The discussion also touches on Ecobee's innovative "donate your data to science" program, which allowed the company to contribute to groundbreaking research in energy efficiency and senior care. Lombard's insights demonstrate how corporations can act as responsible citizens in their communities while driving innovation and growth.

Don't miss this inspiring conversation that will change the way you think about business and sustainability.

-------------------------------------

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this enlightening episode of the Startup CEO Show, host Mark MacLeod welcomes Andrew D'Souza, the innovative co-founder and CEO of Boardy, for a deep dive into the world of AI-driven networking and entrepreneurship. D'Souza, known for his previous success with Clearco, shares candid reflections on his journey from building a unicorn company to exploring the frontiers of AI technology. The conversation offers listeners a rare glimpse into the mind of a serial entrepreneur, covering everything from the challenges of hypergrowth to the intricacies of navigating investor relationships in today's competitive landscape.

Andrew introduces Boardy, an AI super connector that's redefining how professionals network and collaborate. He explains the groundbreaking technology behind Boardy, including its use of advanced voice models and AI to facilitate meaningful connections. The discussion explores the potential for AI to unlock hidden value in human interactions and reshape our understanding of work and productivity. Andrew's vision for Boardy goes beyond traditional AI assistants, imagining a future where AI entities play a more integral role in society, with their own agency and autonomy.

The episode delves into the impact of AI on various industries, with a particular focus on SaaS companies. D'Souza challenges CEOs to rethink their competitive advantages in light of rapidly evolving AI capabilities, offering valuable insights for business leaders navigating this technological revolution. The conversation also touches on the broader implications of AI for the job market and workforce development, with D'Souza presenting an optimistic view of AI's potential to enhance human creativity and self-expression. The episode concludes with a thought-provoking discussion on the Canadian tech landscape and the cultural challenges faced by ambitious entrepreneurs.

Tune in now to gain invaluable insights from one of tech's most forward-thinking leaders.

In this episode of the Startup CEO Show, join us as Mark MacLeod welcomes special guest Amar Varma, co-founder and CEO of Mantle, for a captivating discussion. Discover how Mantle is revolutionizing private asset tracking through innovative AI integration and fresh approaches.

Gain strategic insights from Amar as he explores market opportunities for startups and the transition to an enterprise-driven model. Explore the complexities of investment strategy and the transformative potential of AI, all while delving into Amar's invaluable firsthand experiences in the startup world.

Don't forget to subscribe for more insights on how to become a successfull startup CEO!

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Key moments:

00:00 - 04:39 Reimagining market with fresh approach and AI.

04:39 - 08:23 A dominant player in finance.

08:23 - 13:03 Becoming investor after previous experiences with no regrets.

13:03 - 16:25 Invest wisely, be mindful about timing and luck.

16:25 - 20:26 Embracing feedback, self-awareness, and professional growth.

20:26 - 23:54 Understanding my process and transparent communication

23:54 - 26:46 Identify winners by DNA and winning consciousness.

26:46 - 29:29:Obsessive people find success in various domains.

32:00 - 37:14: Considering alignment before investing in overpriced companies.

37:14 - 41:05: AI progress with potential misuse concerning.

41:05 - 43:11: Founder-led company going public.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this latest episode of the Start Up CEO Show, we dive deep into the dynamic world of startups, revealing the secrets behind successful entrepreneurship and innovative business strategies. 

Join us as we examine the intricate balance between risk and innovation, a critical aspect for any aspiring entrepreneur or business enthusiast.

Our guest, Kirk Simpson, is a renowned figure in the startup ecosystem. With a career rich in entrepreneurial ventures, Kirk has navigated the challenging waters of the business world, transforming obstacles into opportunities for success. 

His journey is not just inspiring but also packed with valuable lessons for anyone looking to make their mark in the business world. In this episode, Kirk shares his insights on managing risks, fostering innovation, and the mindset needed to excel in the constantly evolving business environment.

Don't forget to subscribe for more insightful episodes like this.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

The Startup CEO Show takes a deep dive into the world of conscious entrepreneurship in this enlightening episode featuring Shrad Rao, the visionary former CEO of Wagepoint. Host Mark MacLeod guides listeners through a fascinating discussion that bridges Eastern spirituality with Western business acumen. Rao, fresh from stepping down after over a decade at the helm of Wagepoint, shares his journey of building a successful tech company while maintaining a strong spiritual foundation.

The episode explores the emotional landscape of transitioning out of a long-held CEO position, with Rao candidly discussing the mix of exhilaration and grief he experienced. He reveals his unique approach to leadership, emphasizing the importance of caring deeply for employees and creating a culture of experimentation and growth. Rao's insights into conducting personal "culture calls" with potential hires and his philosophy on parting ways with employees compassionately offer valuable lessons for leaders at all levels.

MacLeod and Rao delve into the power of intuition in business decision-making, discussing how to balance analytical thinking with gut instincts. The conversation takes an introspective turn as both share their experiences with Eastern spiritual practices and how these inform their leadership styles. Rao's perspective on the intersection of creativity and technology, inspired by figures like Steve Jobs and Warren Buffett, provides a fresh take on innovation in the tech industry.

This episode is a must-listen for entrepreneurs and leaders seeking to infuse their business practices with mindfulness and compassion while driving success.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, host Mark MacLeod sits down with Sameer Dhar, co-founder and CEO of NiaHealth, to explore the intersection of entrepreneurship and personal health. Dhar shares his journey from diabetes researcher to investment banker to healthcare innovator, highlighting how his experiences shaped NiaHealth's mission to bring proactive, evidence-based healthcare to the masses.

The conversation delves into the challenges of Canada's healthcare system and how NiaHealth is working to complement and alleviate pressure on public healthcare through personalized diagnostics and actionable insights. Dhar emphasizes the importance of empowering individuals with consumer-friendly health information, allowing them to take charge of their wellbeing in ways previously unavailable. The episode offers valuable insights for entrepreneurs on balancing the demands of building a company with maintaining personal health, drawing parallels between running a successful business and managing one's physical wellbeing.

Tune in to discover how you can leverage the latest in health technology to enhance your performance and quality of life.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/