Podcast
The Startup CEO Show
Hosted by Mark MacLeod · EN
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.
11episodes
Episodes
Newest firstAll episodes
Jerry Colonna on the Founder’s Honest Journey
Feb 1600:51:35Tap to summarizeJoin 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
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Why Founder Energy Is the Ultimate Growth Lever
Feb 200:45:23Tap to summarizeWant 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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1600 People, Virtual First: Scaling Without Chaos
Jan 1900:49:02Tap to summarizeJoin 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 PecherskiyConnect with me: My website: https://limitless.ceo/LinkedIn:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/
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300 Coffees, 12 Years, One Big Exit
Jan 501:03:36Tap to summarizeJoin a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness.Check out: https://limitless.ceoWhat 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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Why Creativity + Data Is the New CEO Superpower
Dec 1500:55:55Tap to summarizeJoin a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness.Check out: https://limitless.ceoWhat 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 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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The Backup That Built a Business: Inside Rewind with Mike Potter
Dec 100:51:44Tap to summarizeJoin a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness.Check out: https://limitless.ceoWhat if the “boring” SaaS backup tool you rarely think about is actually a rocketship, and the CEO behind it refuses to sacrifice his marriage or his health to build it?In this episode, I sit down with my friend Mike Potter, co-founder & CEO of Rewind – the category-defining backup platform for mission-critical SaaS apps like Shopify, GitHub, Jira, Confluence, and more. We talk about how a catastrophic hard-drive failure at Adobe turned Mike into a backup obsessive, how he and his co-founder quietly created a new category in SaaS, and why the big platforms’ own backups won’t save you when just your account goes sideways. We also get into the messy reality behind the scenes: bootstrapping for years, supporting 16+ platforms without drowning, and ultimately raising from Inovia, Bessemer, and Insight without abandoning their values.The second half of the conversation is all about how to build a big business without blowing up your life. Mike shares the story of his first startup nearly costing him his marriage, the panic attack that became a turning point, and the explicit pact he made with his co-founder this time: “The business will not destroy our relationships.” We unpack his operating rules for sustainable high performance: respecting people’s time, using sleep and space to solve hard problems, building systems so the CEO can walk away, and delegating so the company no longer depends on him to “save” it.If you’re a founder or CEO trying to balance hypergrowth with your health, your family, and your sanity, this one’s for you.Mike Potterhttps://www.linkedin.com/in/mikepotter/?originalSubdomain=caConnect with me:My website: https://limitless.ceo/Linkedin:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/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
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The AI Pivot That Took BlueJ to 300% Growth
Nov 1700:57:09Tap to summarizeWant to unlock your limit as CEO? Come join us:https://limitless.ceo/In this episode, I sit down with Benjamin Alarie, co-founder and CEO of Blue J, to explore one of the most fascinating founder journeys I’ve ever encountered. Imagine simultaneously being a tenured law professor and a venture-backed CEO, while reinventing one of the most painful and universal professional workflows: tax research. Ben shares how Blue J evolved from an academic insight into a hyper-growth AI platform transforming how tax professionals, enterprises, and advisors find answers in seconds instead of hours.We dive deep into the origin story of Blue J, including how a walk down Charles Street in Toronto inspired the name, how Ben threaded the needle between academic life and startup life, and how large language models completely reshaped the company’s trajectory. Ben also breaks down the realities of selling into a concentrated enterprise market, navigating the economics of professional services, and scaling from idea to 300%+ year-over-year growth.Whether you’re a founder, an operator, or a curious learner, this conversation is packed with insights on identity, reinvention, enterprise sales, AI transformation, and the emotional journey of becoming a venture-backed CEO.Benjamin AlarieConnect with me:My website: https://limitless.ceo/Linkedin:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/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
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Focus, Cash Flow & Comebacks: Inside EMERGE Commerce with Ghassan Halazon
Nov 300:57:09Tap to summarizeJoin a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness. Check outhttps://limitless.ceo/ What does it take to survive, then thrive, as a public e-commerce CEO? In this episode of Start Up CEO, I sit down with Ghassan Halazon, co-founder and CEO of Emerge Commerce, who has spent 15-plus years buying, building, and turning around brands that together have generated more than one billion dollars in GMV.We go deep on the shift from a wide roll-up to a focused portfolio in grocery and golf, the reality of timing acquisitions during the pandemic, and how Ghassan led a dramatic debt reduction while getting back to profitable growth. He shares how to handle competitor outreach, how to think about LTV to CAC, and what public market life actually feels like when the cycle turns.If you are scaling an e-commerce company or considering acquisitions, this is a playbook on focus, discipline, and resilience.Ghassan Halazon
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The FASTEST Growing Fintech You’ve Never Heard Of (yet)…
Oct 2000:56:55Tap to summarizeIf you want to connect with other CEOs who are grappling with co-founder conflict, come join Limitless.ceoI’ve known Yoseph West, the Co-founder and CEO of Relay, for years, and in this episode of The Startup CEO Show, we finally get to unpack his story. Yoseph has quietly built one of the fastest-growing fintech companies in North America, serving thousands of small businesses while staying true to his principles.We talk about how he went from the early days at Hubdoc to leading a 200-person company, what it takes to earn trust in a regulated space, and how he’s learned to lead with intensity without burning out. Yoseph opens up about his personal growth journey, from hands-on founder to strategic CEO, and how coaching, emotional intelligence, and discipline have shaped him along the way.This is one of those conversations that reminds you what real leadership looks like: clarity, humility, and long-term focus. If you’re building something ambitious and trying to grow as fast as your company, this one’s for you.Yoseph West relayfi.comConnect with me:My website: https://limitless.ceo/Linkedin:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/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
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Why Co-Founders Break Up (And How to Prevent It)
Oct 600:50:35Tap to summarizeIf you want to connect with other CEOs who are grappling with co-founder conflict, come join Limitless.ceoWhy do 65% of startups fail?It’s not a lack of funding. It’s not product-market fit. Matt Jones, psychologist, coach, and author of The Co-Founder Effect, says the number one killer of startups is co-founder conflict.In this episode of The Startup CEO Show, I sit down with Matt to unpack why co-founder relationships make or break companies and what founders can do to prevent disaster. We explore the hidden reasons co-founders clash, why alignment and values matter more than strategy or capital, and the practical frameworks Matt uses to save partnerships before they implode.Whether you’re choosing a co-founder, scaling through Series B, or already feeling the strain, you’ll learn how to protect your partnership and your company’s future.Dr. Matthew Jones-Book The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup SuccessConnect with me:My website: https://limitless.ceo/Linkedin:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/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
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