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/

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