The Startup CEO Show

Join 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/

Join 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

Want 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

Join 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

If 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