The Startup CEO Show

Mark MacLeod
  • 5.0 (2)
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The Startup CEO Show

The Startup CEO Show hosted by coach and advisor Mark MacLeod, brings you veteran CEOs each week who have collectively had had billion dollar valuations, 9 figure exits, and millions in revenue each week. Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them. This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions. About Mark MacLeod 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.

  1. Scaling to a Million Customers: Lessons from Propel Holdings

    6D AGO

    Scaling to a Million Customers: Lessons from Propel Holdings

    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/

    54 min
  2. Transforming Personal Wellness: The Future of Health Tech

    APR 14

    Transforming Personal Wellness: The Future of Health Tech

    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. -------------------------------- 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/

    51 min
  3. Why Shopify is a magnet for founders with Glen Coates

    APR 7

    Why Shopify is a magnet for founders with Glen Coates

    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/

    49 min
  4. From Bootstrapped to Public: Lightspeed's 20-Year Evolution

    MAR 31

    From Bootstrapped to Public: Lightspeed's 20-Year Evolution

    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/

    43 min
  5. From 49 Cents to Millions: Beehiiv's Incredible Startup Journey

    MAR 24

    From 49 Cents to Millions: Beehiiv's Incredible Startup Journey

    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.

    49 min
  6. The CEO as Chief Marketer: Personal Branding in Tech

    MAR 17

    The CEO as Chief Marketer: Personal Branding in Tech

    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/

    1 hr
  7. Building a Mission-Driven Brand: Lessons from Knix Founder

    MAR 10

    Building a Mission-Driven Brand: Lessons from Knix Founder

    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! ---------------------- 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/

    48 min
  8. Startup Resilience: How Clutch Bounced Back from Near-Collapse

    MAR 3

    Startup Resilience: How Clutch Bounced Back from Near-Collapse

    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/

    48 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

The Startup CEO Show hosted by coach and advisor Mark MacLeod, brings you veteran CEOs each week who have collectively had had billion dollar valuations, 9 figure exits, and millions in revenue each week. Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them. This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions. About Mark MacLeod 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.

Information

  • Creator
    Mark MacLeod
  • Years Active
    2024 - 2025
  • Episodes
    60
  • Rating
    Clean
  • Copyright
    © Copyright 2025 Mark MacLeod
  • Show Website
    The Startup CEO Show

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