The Startup CEO Show

By: Mark MacLeod
  • Summary

  • 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 2024 Mark MacLeod
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Episodes
  • The Power of Gratitude in Business: Insights from Indochino’s CEO
    Nov 18 2024

    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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    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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    53 mins
  • From $50B to $1 Trillion: Wealthsimple's Vision
    Nov 11 2024

    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/

    Show more Show less
    55 mins
  • The random episode: US election, Sovereign AI, and more with Amar Varma
    Nov 5 2024

    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.

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    Looking to elevate your leadership game with actionable strategies?

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

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    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/

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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/

    Show more Show less
    48 mins

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