The Startup CEO Show

De: Mark MacLeod
  • Resumen

  • 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.
    Copyright 2025 Mark MacLeod
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Episodios
  • Building a Mission-Driven Brand: Lessons from Knix Founder
    Mar 10 2025

    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/

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    48 m
  • Startup Resilience: How Clutch Bounced Back from Near-Collapse
    Mar 3 2025

    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.

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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/

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    48 m
  • From Fintech to AI: Andrew D'Souza's Entrepreneurial Evolution
    Feb 24 2025

    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.

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    48 m

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