The Breakout CEO

Marketplace businesses look simple on the surface: connect supply and demand and let the network grow. But for CEOs, the real risk isn’t growth — it’s misalignment between stakeholders . In this episode, Paul Roberts, CEO of GoodBite, explains why marketplace startups often fail when incentives between customers, partners, and suppliers drift apart — and why scaling too early can make the problem...

What does it take to scale a company in one of the most competitive industries in technology? In this episode of the Breakout CEO Podcast, Jeff Holman sits down with Michael Chaput, CEO of Endsight , to explore the leadership transformation that helped him grow a managed services company to more than $35 million in revenue and 140 employees . Michael shares the lessons he learned after his first c...

Most founders start with a simple idea. Then growth happens — and suddenly the company becomes ten different things at once. In this episode, PodMatch founder Alex Sanfilippo shares the moment he realized his business had become confusing to the market. After launching multiple offerings and expanding quickly, he discovered that customers no longer understood what the company actually did. For CEO...

Most CEOs don’t notice executive misalignment when it starts. They notice it when they’re spending 70–80% of their time on people problems. In this Advisory Insight episode, Robert White breaks down the hidden cost of leadership misalignment — and why it almost always traces back to a failure to clearly define and enforce purpose, vision, and values. Episode Description Executive misalignment rare...

Most scaling CEOs say they want growth. Fewer are willing to confront the moment when growth requires them to give up control. In this Advisory Insight episode, Ral West breaks down the recurring pattern she sees: founders who want scale but continue operating as if the business would “die without me.” That tension — between control and trust — is where companies either plateau or accelerate. Epis...

The warning signs CEOs are scaling complexity instead of structure Scaling doesn’t fail because of ambition. It fails because of misalignment. Many founders believe they’re building for growth — launching new services, expanding markets, hiring faster. But without structure underneath that growth, complexity compounds. What feels like momentum becomes chaos. What looks like opportunity becomes bot...

In this episode, Jeff Holman sets the stage for a new Breakout CEO format: Advisory Insights , a short series of episodes where experienced operators and advisors share the patterns they see inside scaling companies. The theme for this series is executive leadership misalignment — a problem that rarely shows up as a dramatic conflict, but instead builds slowly through small signals inside the busi...

CEOs who want the option to sell their company later must run it with the operational discipline, customer traction, and leadership structure investors expect long before an exit process begins. Many CEOs delay thinking about exit readiness because it feels premature or distracting from growth. The hidden risk is that companies built around founder effort, weak metrics, or informal operations beco...

Product-market fit is supposed to unlock growth. But what happens when customers show up and investors don’t? In this episode, Meghan Higney — founder of the footwear brand Message — shares what it looks like when early traction collides with a funding drought. After launching to strong demand and immediate media attention, Meghan discovered that validation from customers didn’t translate into cap...

When growth pressures your standards, the decision defines your brand. Every scaling CEO eventually faces it: the deal that’s close but not quite aligned, the client outside your ideal profile, the opportunity that promises revenue—but threatens your operating discipline. Chris Shurian built multiple companies across construction and hospitality by choosing standards over opportunistic growth. He...

Every founder says perseverance is key. Fewer know when it becomes expensive. In this episode, John Cousins reflects on the hardest decision a CEO faces: when to push through obstacles — and when to admit the wall in front of you is brick. Drawing from his experience launching and losing control of a startup, John breaks down the tension between conviction and reality, control and collaboration, p...

Authority used to be assumed. Today, it must be built. As markets become more transparent and commoditized, pricing pressure doesn’t begin with competition — it begins with perception. When differentiation disappears, the only lever left is price. In this episode, Dennis “DM” Meador explains why founder-led visibility is no longer optional — and how CEOs who fail to build authority early eventuall...

Most CEOs assume that winning means competing harder. Andrew Ackerman learned the opposite. When Dreamit Accelerator found itself stuck behind larger, more established competitors, the question wasn’t how to move from number three to number one. It was whether that race was worth running at all. This episode explores the pivotal decision to stop fighting for position in a crowded market — and inst...

Most founders prefer to license. It’s a lower risk. Lower capital exposure. Fewer operational headaches. But what happens when the incumbents won’t move, and your product only works if someone actually operates it? In this episode, Jeff Doss shares the pivotal decision to stop trying to license his patented anchoring system and instead operate the business himself inside a small, skeptical, highly...

Small business credit isn’t broken because of a lack of data; it’s broken because the system was never designed for how businesses actually operate. In this episode, host Jeff Holman speaks with Sal Rehmetullah, CEO and Founder of Worth AI. He has scaled, exited, and re-entered fintech at the highest levels. After building Stax Payments into a market leader and navigating a billion-dollar recapita...

Markets don’t wait for consensus. In this episode, Shay Levi explains how CEOs recognize the moment when speed and conviction matter more than alignment and what it costs to hesitate. Drawing from building and exiting Noname Security and starting Unframe, Shay breaks down how he made contrarian calls under uncertainty, trusted firsthand signals over investor pushback, and moved aggressively when t...

Scaling doesn’t usually fail because of a bad product. It fails because focus erodes slowly, one customer, one feature, one exception at a time. In this episode, Keith Norris shares the decisions that nearly broke his company and the hard reset that followed. From serving too many customers across too many industries to running multiple products that were effectively separate businesses, this is a...

In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Zach Barney, founder and CEO of Mobly, to talk about a problem many growth-stage companies quietly accept. They spend a lot on in-person events and have no real way to know what is working. Zach explains how his background as a VP of Sales exposed a gap most teams accept as normal. Digital marketing is measured closely. In-per...

What does it actually take to scale a manufacturing business in the U.S. today? In this episode of The Breakout CEO, Jeff Holman sits down with Spencer Loveless, second-generation CEO of Dustless Technologies and founder of Merit3D ⁨@Merit-3D⁩ . Spencer grew up inside a family-run manufacturing business and stepped into leadership early. Over time, he’s had to navigate the realities most CEOs don’...

AI can organize information faster than any team you’ve ever built. It can surface patterns, speed up workflows, and remove friction from execution. But it still can’t make judgment calls when the data is incomplete, the market is shifting, and real money is on the line. In this episode of The Breakout CEO, Jeff Holman talks with entrepreneur and financial advisor Luigi “Lou” Rosabianca about wher...

Most leadership advice breaks down the moment real pressure shows up. In this episode of The Breakout CEO, Cydni Tetro, 3-time CEO, board member, and former CIO of Swire Coca-Cola, draws from her experience as a 3-time CEO, enterprise executive, and board member to talk through those moments honestly. Not as lessons learned in hindsight, but as decisions made while the outcome was still unclear. C...

What does it take to build a company when the mission matters more than momentum? In this episode of The Breakout CEO, Jeff Holman sits down with Thomas Bishop, founder of Paleblue, for a grounded conversation on conviction, persistence, and building products that genuinely change behavior. Tom shares how a near-death experience reshaped his career decisions and why meaningful missions became the...

Every CEO reaches a threshold where hustle and revenue aren’t enough. In this episode of The Breakout CEO, host Jeff Holman cuts into the hard operating truths that separate early growth from a sustainable scale. We explore what happens when pricing, financial clarity, team leadership, and systems become the deciding factors—not just harder work or bigger marketing. This conversation goes deep on...

What does it really take to sell a SaaS business successfully? In this episode of The Breakout CEO, Jeff Holman sits down with Andrew Gazdecki, founder of Acquire.com (formerly MicroAcquire) to unpack what founders need to know about buying, scaling, and exiting online businesses. Andrew has helped thousands of founders sell SaaS companies, ecommerce brands, mobile apps, and digital businesses. In...

What does it really take to break through as a CEO when the pressure is highest, and the path forward isn’t clear? In this episode of The Breakout CEO Podcast, I sit down with Nikky Kho @NikkyKho , an entrepreneur, AI pioneer, and lifelong learner for a wide-ranging conversation on the breakout moments that shape leaders at the highest levels. Nikky’s journey is anything but conventional. Over a 2...