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The Startup CEO Show

The Startup CEO Show

By: Mark MacLeod
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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 Career Success Economics Management Management & Leadership Personal Finance
Episodes
  • AI's Impact on SaaS: Why Software is Changing Forever
    May 19 2025

    In this captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Josh Pantony, co-founder and CEO of Boosted AI, to explore the cutting-edge world of artificial intelligence in finance. Josh, a veteran in the AI space, shares his journey from co-founding Maluva, an early competitor to Siri, to his current role revolutionizing Wall Street with AI-powered tools.

    The conversation delves into the technological breakthroughs that have made modern AI possible, including unsupervised training and attention networks, and how these advancements are reshaping the financial industry. Josh provides fascinating insights into the future of SaaS, predicting that AI will soon be able to auto-generate user interfaces and drastically reduce the cost of software development.

    He envisions Boosted AI becoming an integral part of every professional investment manager's workflow, ultimately accelerating wealth creation for society as a whole. Tune in to gain valuable insights from one of AI's pioneering minds and learn how these innovations may impact your own career and investments.

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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/

    Contact Mark: https://markmacleod.me/

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    52 mins
  • Bootstrapping Success: Growing 96% in a Single Year
    May 12 2025

    In this episode of the Startup CEO Show, Mark MacLeod sits down with Craig Letton, founder and CEO of alcohol marketing platform hyble, for a raw and honest discussion about entrepreneurship, burnout, and building a successful global business. Craig shares the remarkable story of how he took over his parents' small print shop in Scotland and transformed it into a high-growth tech company serving major alcohol brands worldwide. He opens up about the immense challenges he faced along the way, including bootstrapping the business, navigating the pandemic, and executing a massive U.S. expansion that pushed him to the brink of burnout.

    Craig provides a candid look at the toll this took on his mental and physical health, and shares the strategies that helped him persevere and ultimately thrive. From tapping into his competitive athlete mindset to carving out time for self-care, his insights offer valuable lessons for any founder going through difficult times.


    The episode also explores Craig's approach to building an award-winning company culture based on authenticity, humility and continuous learning. Don't miss this must-listen conversation on navigating the entrepreneurial journey.

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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
    50 mins
  • Athlete to Entrepreneur: PartnerStack Founder's Winning Mindset
    May 5 2025

    In this episode of the Startup CEO Show, Mark MacLeod sits down with Bryn Jones, co-founder and CEO of PartnerStack, to explore the world of B2B partnerships and scaling a successful SaaS company. As PartnerStack approaches its 10-year anniversary, Bryn shares valuable lessons from his journey as a competitive swimmer turned entrepreneur. He discusses how the discipline and resilience he developed as an athlete translated into building a thriving business. Bryn provides a candid look at the challenges of creating a new category in the partnership space, including navigating relationships with analysts and adapting to market volatility.

    The conversation delves deep into the intricacies of successful B2B partnerships, with Bryn emphasizing the importance of putting partners first and building relationships based on mutual value. He shares insights on identifying ideal partner profiles, setting up effective incentives, and the role of enablement in driving partnership success. Bryn also touches on the potential impact of AI in streamlining and optimizing partnership processes. The episode offers a wealth of practical advice for startups looking to leverage partnerships for growth, including the pros and cons of selling to early-stage companies.

    Perhaps most compellingly, Bryn opens up about the challenges of managing rapid growth and the importance of addressing underlying issues rather than simply chasing numbers. He reflects on the personal and professional lessons learned during PartnerStack's journey, including the value of trusting one's instincts as a leader. Tune in to gain a deeper understanding of how partnerships can drive business growth and the key factors that contribute to long-term success in the SaaS world.

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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/

    Contact Mark: https://markmacleod.me/

    Show more Show less
    55 mins
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