The Breakout CEO

When a services company and a product company try to grow under the same roof, one of them eventually has to lose. In this episode, Jared Shepard explains the decision that forced him to spin Hypori out of his 20 year old, bootstrapped services company, Intelligent Waves, and raise venture capital for the first time in his career as a founder. He walks through the moment he realized a secure commu...

Most CEOs never admit what they are bad at, and it costs them the exact hires and decisions that could help their business scale. Larry Gould built one of the world's largest language companies, The Big Word, and years earlier built and sold a recruitment business, but neither started with a plan. Both trace back to moments most founders would rather bury: a childhood spent selling comics door to...

Most scaling CEOs assume a revenue problem is a sales and marketing problem, and it costs them the real diagnosis. In this episode, Kati Peterman, founder of the fractional executive firm YourFRX, breaks down why so many operations issues get misread as leadership or marketing failures, and what actually happens when a CEO gets too far removed from their own numbers. Kati walks through her five fi...

Most companies eventually get commoditized, not because their product is weak, but because the thinking that made them different never gets written down anywhere but the founder's head. As a company scales and adds layers of salespeople, that original thinking dilutes into generic spec language, and CEOs find themselves competing on price against rivals who look just like them. Simon Bowen, founde...

Louis Swart built and sold multiple businesses — including one exit that scaled to $35 million in annual revenue — and still felt broken inside. In this conversation, he unpacks the diagnostic framework he now uses with CEOs: why success and self-worth are separate variables, why the beliefs driving self-sabotage almost always trace back to childhood, and why no one can diagnose their own blind sp...

Most CEOs assume they're judged on execution — results, competence, getting things done. Executive communication coach Mike Acker argues that's only half the equation. Presence, he explains, doesn't just support execution; it multiplies it, and the gap between the two can quietly cap how far a leader rises, or open doors execution alone never could. In this conversation, Mike traces that idea thro...

In 2015, a currency shock pushed the Canadian dollar from parity to $1.46 against the US dollar in eighteen months — a 46% jump in costs for Solpak, the packaging distribution company David Salerno had spent years building. At the worst point, the company was net-losing $30,000 a month, with hundreds of thousands in outstanding payables piling up at the same time. David Salerno, founder of Solpak...

When one of OneMeta's first major enterprise contracts went quiet — right after signing, right after the prepaid revenue was recorded — nothing happened for six months. Saul Leal, CEO of OneMeta, walks through why the deal stalled, how his team learned to diagnose the real cause instead of assuming failure, and what changed when a board member reframed the entire situation. This episode follows th...

Most founders spend years perfecting a dashboard. George Hartley — who built and sold SmartrMail (acquired by Relay Commerce in 2022) and co-founded Bluethumb, Australia's largest online art marketplace — is betting his third company on removing it entirely. Nitrosend runs from inside Claude, Cursor, or ChatGPT, with AI agents doing the majority of the work. In this episode, George walks through t...

Most scaling companies don't fail because they stop trying — they fail because they keep doing more of what already isn't working. In this episode, Jeff Holman talks with Diane Moura, Founder & CEO of ZenChange Marketing, about what actually separates companies that break through a growth ceiling from those that stay stuck. Diane has spent decades working with Fortune 500 companies and now adv...

Most founders don't have a hiring problem — they have a decision problem. Operations advisor Lia Garvin has spent years inside teams at Microsoft, Apple, and Google, and now works directly with founders running businesses of three to fifty people, diagnosing why so many of them can't step back from the day-to-day. In this episode, she breaks down why founders keep absorbing decisions their team co...

What separates CEOs who build resilient companies from those who burn out chasing the next motivational boost? In this episode of The Breakout CEO Podcast , Jeff Holman sits down with entrepreneur, speaker, and leadership strategist Rael Bricker to explore why lasting business growth starts with vision—not motivation. Drawing from decades of experience leading businesses across engineering, educat...

As companies grow, the CEO's role must evolve. Yet many founders stay trapped in the day-to-day, becoming the very bottleneck that limits their company's growth. In this Advisor Insights episode, Jeff Holman sits down with Logan McKnight , Founder and Principal Consultant at GoodKnight Consulting , to explore what it takes for leaders to gain "strategic altitude." Drawing on his experience as both...

Every scaling e-commerce business eventually collides with the same silent problem: customers who don't get what they ordered, when they were promised it. Jevon Le Roux, CEO and co-founder of Keeyu, lived that problem firsthand before building a company to solve it — and along the way, a well-known investor told him it couldn't be done. In this episode, Jevon breaks down why customer service has b...

What happens when someone reaches the top of the financial world—only to realize success isn't enough? In this episode of The Breakout CEO Podcast , Jeff Holman sits down with Scot Cohen , CEO of WRAP , to explore the deeply personal journey that led him from a successful career in finance to building a company focused on reducing harm in public safety. Scot shares why he walked away from Wall Str...

What separates companies that become market leaders from those that remain just another product? In this episode of The Breakout CEO Podcast , Jeff Holman sits down with Romney Williams , entrepreneur, inventor, and CEO of DRYOUT , to explore the leadership decisions behind building a category-defining business. Drawing from decades of experience launching companies, protecting intellectual proper...

What if your biggest growth opportunity wasn't your product—but your customers? In this episode of The Breakout CEO Podcast , Jeff Holman sits down with Julie Tylman , Co-Founder and Co-CEO of Group Together , to discuss how relentless customer listening shaped every major decision in her company's journey. Julie shares how a simple idea to simplify group gifts evolved into an international busine...

Artificial intelligence is transforming nearly every industry—but according to Sheldon Wolf , AI isn't here to replace real estate professionals. It's here to empower the ones who embrace it. Drawing on more than 35 years of experience in real estate investing, development, brokerage, and PropTech, Sheldon explains why the future belongs to leaders who understand customer behavior, not just techno...

What does it take to leave a successful corporate career and build a healthcare startup from scratch? In this episode of The Breakout CEO Podcast , Seth Merritt shares how a side project became Welby Health, a fast-growing healthcare technology company transforming chronic care management. Seth explains why moving quickly—not perfectly—became his competitive advantage, how customer conversations s...

As companies scale, the first signs of trouble rarely appear on a dashboard. They show up in stretched teams, founder bottlenecks, and hiring decisions that lag behind growth. In this episode of The Breakout CEO Podcast , David Khim, Co-Founder of Omniscient Digital, explains why CEOs need to pay attention to qualitative signals before traditional metrics catch up. Drawing from his own experience...

What separates CEOs who build enduring companies from those who simply manage growth? For Vikas Sehgal, the answer wasn't a better strategy or a more aggressive sales process. It was a fundamental shift in how he viewed leadership. After helping build Nagarro from a living room startup into a billion-dollar global technology company, Vikas discovered that sustainable growth comes from shared value...

Most service companies lead with what they do. The ones that grow the fastest lead with the problems they solve. In this episode of The Breakout CEO Podcast , Mike LaVista, Founder & CEO of Caxy Interactive, explains how one shift in positioning transformed his consulting business from transactional projects into strategic partnerships, dramatically increasing deal size and changing the conver...

Every CEO knows people matter. Fewer recognize that hiring is one of the highest-leverage strategic decisions they make. In this episode of The Breakout CEO Podcast , Fletcher Wimbush shares why building a better company starts with building a better hiring system. From hiring for integrity over raw talent to eliminating "talented terrors" and staying relentlessly focused, Fletcher explains how be...

Most founders know how to build. Fewer know when the evidence is strong enough to commit. In this episode, Arthur Jessop shares how he moved from a successful corporate career into entrepreneurship after recognizing a series of market signals that convinced him Base Case was more than just an interesting product idea. From CES validation and crowdfunding success to customer feedback and ICP refine...

As companies scale, leaders often invest heavily in systems, processes, and technology while overlooking the one advantage that compounds across culture, retention, sales, and customer experience: human connection. In this conversation, Richard Blank shares lessons from building Costa Rica's Call Center from the ground up, why communication remains a competitive advantage in an AI-driven world, an...