The Breakout CEO

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 a healthcare CEO and executive adviso...

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 been built backwards for twenty...

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 Street, the leadership lessons he l...

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 property, and partnering with global brands, R...

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 business, why their biggest product brea...

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 technology. He shares how every major...

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 shaped every major product ...

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 scaling a bootstrapped agency through...

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 global technology company, Vikas discovered that sustainable growth comes from shared values, empowering great people, and solving customer pr...

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 conversations he was having with CEOs. Alon...

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 better hiring decisions shape culture,...

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 refinement, Arthur explains how he learne...

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, and how leaders can create cultures t...

Inventory problems rarely start as inventory problems.

In this episode, Alex Hennick explains how excess inventory, warehouse pressure, and distressed assets often reveal deeper operational and financial issues long before most CEOs fully recognize them. Drawing from nearly two decades in liquidation and excess inventory markets, Alex shares the patterns he sees repeatedly across scaling businesses — especially when companies...

Most founders think they have a growth problem when they actually have a cash flow problem.

In this episode, Brandon Neely explains why many business owners misunderstand liquidity, leverage, and access to capital — and how those blind spots create unnecessary financial pressure during periods of growth or crisis. Rather than focusing only on revenue, Brandon argues founders need to understand how money actually flows through...

Most CEOs preparing to raise capital focus on pitch decks, projections, and presentation polish. George Dubec argues that investors are making decisions much earlier — based on founder credibility, clarity, visibility, and whether they believe the CEO can actually execute.

In this episode, George explains why investor trust increasingly outweighs traditional fundraising materials, how modern founders should rethink investor co...

Many founders assume growth requires outside capital, debt, or aggressive expansion. Lindsey Prater took a different path.

In this episode, Lindsey shares how she and her sister grew Groovy Peach from an 85-square-foot salon suite into a multi-location, multi-million-dollar business by repeatedly choosing to reinvest earnings instead of extracting them. The conversation explores what happens when founders prioritize retained earnin...

Most startup advice focuses on founders. Gregory Shepard thinks that misses the real problem.

After building and selling multiple companies, investing across the startup ecosystem, and spending years researching startup failure, Gregory came to a different conclusion: founders are often operating inside fragmented systems that were never designed to scale.

In this episode, Gregory breaks down why startup support infrastructure contin...

Scaling a company doesn’t usually fail because of strategy. It breaks when the organization can’t evolve fast enough to support the next stage of growth.

In this episode, Drew Allen shares the realities of rebuilding a leadership team while transforming a business — including failed product launches, painful personnel decisions, engineering bottlenecks, and the challenge of creating a true ownership culture inside ...