The Startup CEO Show

Jerry Colonna on the Founder’s Honest Journey

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 if the fastest way to scale your startup is to stop pretending you’re “crushing it”? In this episode of The Startup CEO Show, I sit down with Jerry Colonna, legendary CEO coach, former VC, and author of Reboot, for a raw conversation about the founder’s inner journey: the anxiety, the bravado, the “should,” and the quiet suffering that often hides behind high growth. Jerry challenges the startup ecosystem’s obsession with spinning a story and reframes “vulnerability” as something simpler and harder: honesty. We unpack why founders feel pressured to perform, how hustle culture disconnects leaders from clarity and compassion, and why building a company is often a personal development journey disguised as a business. We also explore meditation, purpose, equanimity, and why poetry can cut through the monkey mind when nothing else will. If you’re a founder, CEO, or investor who wants to build something big without burning out, this is one of those conversations that sticks with you. Connect with me: My website: https://limitless.ceo/ Linkedin:https://www.linkedin.com/in/themarkmacleod/ Instagram: https://www.instagram.com/markmacleodcoach/ Subscribe for more founder-level conversations. Jerry Colonna - Reboot.io | LinkedIn https://www.linkedin.com/in/jerry-colonna-reboot/ Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS. https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1

Why Founder Energy Is the Ultimate Growth Lever

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

1600 People, Virtual First: Scaling Without Chaos

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 [https://www.linkedin.com/in/vitalypecherskiy/overlay/about-this-profile/] Connect with me: My website: https://limitless.ceo/LinkedIn:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/

300 Coffees, 12 Years, One Big Exit

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 [https://www.linkedin.com/in/blairhlivingston/?originalSubdomain=ca] Connect with me:My website: https://limitless.ceo/LinkedIn:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/

Why Creativity + Data Is the New CEO Superpower

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 happens when your “software startup” accidentally turns into an agency, and that mistake becomes the fuel for your next breakout company? In this episode, I sit down with Reza, founder of Motion, to unpack one of the most honest startup journeys you’ll hear: pivots under pressure, brutal clarity moments, and the insight that reshaped modern growth marketing. We talk about how Shoelace went from a struggling SaaS product to a profitable agency almost overnight, why admitting reality saved the company, and how that experience directly led to Motion, a creative analytics platform built for the new era of advertising, where creative (not targeting) is the ultimate growth lever. Reza explains why the future belongs to creative strategists, leaders who combine left-brain data rigor with right-brain creativity, and why founders must solve the most urgent problems, not the safest ones. We also dive deep into AI-native leadership: how Reza uses AI to prototype ideas, scale the CEO role, rebuild a product from the core, and make bold decisions without hedging. If you’re a founder navigating disruption, creative vs. data tension, or the pressure to reinvent your company before the market forces you to, this episode is for you. Reza Khadjavi [https://www.linkedin.com/in/reza-khadjavi-46802918/?originalSubdomain=ca] Connect with me: My website: https://limitless.ceo/ LinkedIn:https://www.linkedin.com/in/themarkmacleod/ Instagram: https://www.instagram.com/markmacleodcoach/