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/

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

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.ceo

What 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 Potter

https://www.linkedin.com/in/mikepotter/?originalSubdomain=ca

Connect 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 Alarie

Connect 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 out

https://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.ceo

I’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.com

Connect 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

If you want to connect with other CEOs who are grappling with co-founder conflict, come join Limitless.ceo

Why 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 Success

Connect 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/

What happens when 41% of all VC dollars flow to just 10 companies?

In this episode of The Startup CEO Show, I sit down with my friend and serial founder/investor Amar Varma (Mantle, Xtreme Labs, Pivotal) to unpack the new power law era of venture capital, the rise of AI, and what it all means for startup founders today.

We talk about how AI is reshaping startup costs, why some founders are skipping entire funding rounds, and how the next wave of alumni networks could rival the PayPal Mafia. We also dive into what happens when incumbents get disrupted and why the very idea of a moat is being redefined in real time.

This was one of those conversations where I walked away both excited and uneasy about the future of tech startups, VC trends, and entrepreneurship. I think you will too.

Amar Varma

Connect with me:

My website: https://limitless.ceo/

Linkedin:https://www.linkedin.com/in/themarkmacleod/

Instagram: https://www.instagram.com/markmacleodcoach/

 If you’re building, raising, or investing, you don’t want to miss this one.

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

In this illuminating episode of the Startup CEO Show, host Mark MacLeod dives deep into the habits and traits of some of the world's most successful tech leaders. Drawing from his extensive research and experience coaching CEOs, MacLeod explores what sets apart founders who continue to scale and innovate year after year. He examines 11 companies with a collective market cap of $6.4 trillion, including giants like Airbnb, Meta, and Shopify, to uncover the secrets behind their limitless growth.

MacLeod breaks down the personal habits and leadership traits of CEOs like Brian Chesky, Melanie Perkins, and Tobi Lütke, revealing surprising insights about their routines, decision-making processes, and management styles. From prioritizing sleep and mindfulness to fostering customer empathy and making bold bets, these leaders share common threads that contribute to their ongoing success. The episode challenges conventional notions of hustle culture, highlighting how many top CEOs actually prioritize work-life balance, continuous learning, and self-reflection.

Don't miss out on these invaluable lessons from the tech world's most enduring visionaries. Tune in now and unlock your potential for limitless growth.

LIMITLESS CEO: https://limitless.ceo/

Slides: https://pitch.com/v/limitless-leadership-why-some-ceos-never-stop-growing-69v8yn

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/

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

In this insightful episode of the Startup CEO Show, host Mark McLeod sits down with Marie Chevrier Schwartz, former founder and CEO of Sampler, to discuss the challenging journey of entrepreneurship and the importance of community in the startup ecosystem. Marie openly shares her experience of Sampler's bankruptcy, offering valuable lessons on losing product-market fit and the need for founders to separate their identity from their business. She emphasizes the importance of being prepared for market shifts and understanding the type of company you're building. The conversation takes an inspiring turn as Marie discusses her transition to leading Tech2, Canada's largest tech community, where she now focuses on supporting and connecting entrepreneurs across the country. Listeners will gain a unique perspective on failure, resilience, and the power of authenticity in the startup world. Whether you're a seasoned entrepreneur or just starting out, this episode offers crucial insights into navigating the ups and downs of building a company and the vital role of community support. Tune in to hear Marie's candid reflections and learn how to approach entrepreneurship with a healthier mindset.

Marie Chevrier Schwartz

02:29 From Montreal to Entrepreneurship

06:31 When Ventures Fail: Sampler's Story

15:34 Rebirth of a Business Idea

17:55 Bouncing Back from Bankruptcy

02:29 From Montreal to Entrepreneurship

06:31 When Ventures Fail: Sampler's Story

15:34 Rebirth of a Business Idea

17:55 Bouncing Back from Bankruptcy

------------------------------------------------------------------------------

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/

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