The Breakout CEO
The Breakout CEO podcast brings you candid conversations with scaling CEOs at leadership & strategic inflection points. Each episode is a curated interview that explores the mindset, strategy, and pivotal decisions driving breakthrough success for high-growth companies ($5MM-$50MM+). Jeff Holman is the host of The Breakout CEO podcast and the founder of Intellectual Strategies, where he works closely with CEOs and leadership teams of scaling companies on strategy, governance, and risk during periods of rapid growth. Jeff has spent years inside the decision-making rooms of growth-stage companies, helping leaders navigate moments when complexity increases, tradeoffs become unavoidable, and the cost of misalignment rises. He brings a peer-level perspective shaped by that experience, focusing conversations on the inflection points that materially change a company’s trajectory. The Breakout CEO podcast reflects his approach with candid, operator-level discussions centered on real decisions rather than retrospective storytelling or promotion. Guest Participation - We feature a limited number of CEOs leading scaling companies with meaningful, first-hand breakout moments. If you believe your story would add value for an audience of scaling CEOs, please apply here: https://go.intellectualstrategies.com/ Media & Event Partnerships - For press access, on-site recording, or event collaboration inquiries, please contact us. We record a limited number of on-site conversations at select events with CEOs and founders whose stories align with the podcast’s focus on leadership, strategy, and execution.
Episodes
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 learned—sometimes the hard way—that d...
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, persistence and pivot.
If you’re leadi...
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 eventually feel it in their margins.
Dennis Mea...
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 instead redefine the track entirely.
If yo...
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 regulated market. The stakes were rea...
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 recapitalization, he turned his attention t...
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 timing mattered most.
Shay Levi is ...
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 candid look at how complexity quiet...
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-person marketing often is not. That gap ...
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’t see on paper: supply chain breakdow...
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 where AI actually fits in a scaling bus...
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.
Cydni explains why people-centered l...
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 filter for every company he chose t...
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 the decisions that turn growth into l...
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 this conversation, he shares real st...
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 25-year career, he built a company...
What does it really take to move from founder control to strategic optionality?
In this episode of The Breakout CEO podcast, Jeff Holman sits down with Heather Griffith Barber, founder of Queen of Wraps, to unpack the real decisions behind building a company that buyers take seriously.
Heather shares her 18-year journey growing a business from a scrappy family operation into a multi-company platform that ultimately attracted an uns...
Scaling a business does not usually break because of strategy.
It breaks because the CEO is carrying too much.
In this episode of The Breakout CEO podcast, host Jeff Holman sits down with Corinne Morahan, founder and CEO of Grid + Glam, to talk about burnout, boundaries, and the leadership shift that changed how she built her business.
Corinne shares her journey from Wall Street to entrepreneurship, why she burned out more than o...
Scaling doesn’t fail because of strategy, capital, or product. It fails because of a leadership weakness almost every founder carries into growth.
Impatience.
In this episode of The Breakout CEO podcast, Jeff Holman sits down with David Sluss, Professor at ESSEC Business School and advisor to scaling CEOs, to unpack how impatience quietly undermines leadership as companies grow.
David explains why the habits that help founders win...
In this episode of The Breakout CEO podcast, Jeff Holman sits down with Leah Brown, former corporate lawyer turned mediator and founder of The WayFinders Group, to explore what really breaks inside fast-growing companies and how CEOs can address it before it slows everything down.
Leah shares what she’s seen firsthand inside boardrooms and leadership teams when growth outpaces relationships; communication breaks down, and conflict g...
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