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The Startup CEO Show

The Startup CEO Show

Auteur(s): 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 2026 Mark MacLeod Développement commercial et entrepreneuriat Entrepreneurship Finances personnelles Gestion et leadership Économie
Épisodes
  • Why Founder Energy Is the Ultimate Growth Lever
    Feb 2 2026

    Want to unlock your limits as CEO? Come join us: https://limitless.ceo/

    In this episode, I sit down with Justin Mares, co-founder of TrueMed and Founder Health, to unpack a topic most founders ignore until it’s too late: your health is part of your business model. Justin shares how he built companies around prevention instead of reaction and why founder energy, clarity, and resilience directly compound into better decisions, stronger leadership, and long-term business growth. We talk about the hidden costs of burnout, why traditional healthcare fails entrepreneurs, and how treating health like infrastructure changed the way Justin builds. If you’re scaling a company, leading a team, or feeling the weight of constant decision-making, this conversation reframes health not as self-care, but as a strategic advantage. Watch now to learn how elite founders protect their most undervalued asset: themselves.

    Justin Mares

    Connect with me: My website: https://limitless.ceo/ Linkedin:https://www.linkedin.com/in/themarkmacleod/ Instagram: https://www.instagram.com/markmacleodcoach/

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    45 min
  • 1600 People, Virtual First: Scaling Without Chaos
    Jan 19 2026

    Join a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness.

    Check out: https://limitless.ceo

    What no one tells you about scaling is that the “big milestones” usually aren’t revenue numbers; they’re philosophy shifts, focus decisions, and how you build a company that can outgrow its founders. In this episode of The Startup CEO Show, I sit down with Vitaly (StackAdapt) to unpack how StackAdapt scaled to 1,600 people, crossed $500M+ in revenue, and stayed Virtual-First without letting culture collapse into chaos. We talk about what changed when Vitaly stepped into the CEO seat after nine years of founder-led leadership, why they delayed early fundraising and later brought in growth-stage investors (for credibility, maturity, and long-term category leadership), and what it takes to build systems that don’t depend on a few heroic decision-makers. We also get into a powerful insight Vitaly doesn’t hear enough in marketing conversations: a great product makes marketing easier. If you’re building in a crowded market, scaling a remote team, or trying to grow without losing your soul as a company, this one’s for you.

    Vitaly Pecherskiy

    Connect with me: My website: https://limitless.ceo/LinkedIn:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/

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    49 min
  • 300 Coffees, 12 Years, One Big Exit
    Jan 5 2026

    Join a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness.Check out: https://limitless.ceo

    What does it really take for a finance guy to become a startup founder and build all the way to a meaningful exit?In this episode of the Start Up CEO Show, I sit down with Blair Livingston, founder of Street Context, to unpack the real story behind building a vertical SaaS business inside one of the hardest enterprise markets on earth: capital markets. Blair shares how 300 coffees and relentless hustle opened doors early, why “delusional optimism” is a founder superpower, and what it felt like to spend nearly a decade “crossing the desert” before growth finally took off.We also get into the gritty stuff most founders avoid: when raising money becomes a trap, why strategy can’t be driven by capital, how Blair executed a painful 40% layoff to save the company, and why he optimized for control (board + voting) so he could run the business with clarity and transparency. Finally, Blair opens up about the emotional whiplash of selling, post-exit identity shifts, and why he’s now focused on AI + tokenization as the next major wave in finance.

    Blair Livingston

    Connect with me:My website: https://limitless.ceo/LinkedIn:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/

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    1 h et 4 min
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