The Breakout CEO

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 real: capital at risk, reputation on the line, and a local ecosystem convinced it wouldn’t work.

“It wasn’t a foregone conclusion this thing was going to be a winner.”

This conversation is about that moment when a CEO must choose between protecting the downside and taking control.

Jeff Doss, Founder of Beach Bags, built a patented anchoring system designed to replace illegal and unsafe “pinning” practices on Lake Powell. His original plan was straightforward: develop the technology and license it to the existing marina operators.

That plan collapsed.

The incumbents were skeptical. Influential players dismissed the concept. The market was small and tightly regulated. And in a reputation-driven ecosystem, one technical failure could end the business overnight.

“We knew that if there was any failure of our system, we were going to be dead.”

Instead of walking away, Jeff made a different decision: to operate the business directly. That meant capital investment, staffing challenges, marina negotiations, National Park Service approvals, and leading from the front during the first chaotic season.

The result wasn’t guaranteed. It required conviction under pressure and a willingness to own the risk instead of outsourcing it.

Check out Jeff's work at https://beachbagsanchors.com/.

Say hello to Jeff!

LinkedIn: https://www.linkedin.com/in/jeff-doss-937125/

Facebook: https://www.facebook.com/beachbagsanchors/

Instagram: https://www.instagram.com/beachbagsanchorsystem/

YouTube: https://www.youtube.com/@beachbagsanchors9178

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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 to one of the most persistent problems in small business finance: underwriting. Sal explains why incremental fixes fail in regulated, legacy systems and why rebuilding from scratch was the only viable path.

Sal also walks through why small businesses can’t be evaluated like individuals, how legacy financial systems accumulated regulatory debt, and what finally made it possible to rethink underwriting end-to-end. The episode explores the real CEO tradeoff between patching broken systems and having the conviction to rebuild them especially when credibility, timing, and execution all matter.

After exiting a billion-dollar fintech, he faced a familiar CEO question: optimize what exists or start over entirely. His answer reveals how timing, infrastructure, and judgment are not just ideas, determining whether systemic change is possible.

Check out Sal's work at https://worthai.com/.

Say hello to Sal!

LinkedIn: https://www.linkedin.com/in/sal-rehmetullah-59704741/

LinkedIn: https://www.linkedin.com/company/worth-ai/

Facebook: https://www.facebook.com/worthai.risk

Instagram: https://www.instagram.com/salrehmetullah/

Instagram: https://www.instagram.com/joinworth

Twitter: https://x.com/worth_AI

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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 a repeat founder who operates inside fast-forming markets where there is no safe middle ground. After co-founding Noname Security and scaling it rapidly before its acquisition by Akamai, Shay faced a familiar but harder decision: whether to stay on a winning trajectory or step away to build again.

In this conversation, Shay walks through the judgment calls behind choosing API security early, pushing back on investor skepticism, and later leaving a successful company to pursue Unframe at the moment enterprise AI adoption was accelerating. The focus isn’t outcomes, it’s how conviction forms when the data is incomplete, and the pressure is real.

Check out Shay's work at https://www.unframe.ai/.

Say hello to Shay!

LinkedIn: https://www.linkedin.com/company/unframe-ai/

Twitter: https://www.youtube.com/@UnframeAI

YouTube: https://www.youtube.com/@UnframeAI

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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 quietly compounds until a CEO is forced to choose.

He also walks through a rarely discussed phase of company building; pulling back from overextension, navigating painful investor conversations, and deliberately choosing simplicity over sprawl.

Rather than offering growth hacks or frameworks, Keith explains how real CEO decisions get made under pressure when capital structure changes; incentives break, and survival matters more than optics. This episode is about judgment, not tactics.

If you’re juggling multiple products, markets, or growth paths, this conversation will help you recognize when expansion stops being progress.

Check Keith's work at https://www.kpifire.com/.

Say hello to Keith!

Facebook: https://www.facebook.com/KPIFire/

Instagram: https://www.instagram.com/kpi.fire/

LinkedIn: https://www.linkedin.com/in/keithnorris/

LinkedIn: https://www.linkedin.com/company/kpi-fire/

YouTube: https://www.youtube.com/@KPIFire

Think you'd be a great guest on the show? Apply https://go.intellectualstrategies.com/

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 led him to start Mobly and focus on bringing clearer tracking and follow-up to face-to-face marketing.

The conversation also goes well beyond product and growth. He shares openly what it was like to run out of runway faster than expected, raise capital in a tougher market, and deal with serious anxiety while leading a growing company. He talks about getting help, being honest with his team, and why founders should not try to carry everything alone.

This episode is a realistic look at what scaling actually feels like, and how better decisions come from clarity, not optimism.

Check out Zach's work at https://www.getmobly.com/.

Say hello to Zach!

Instagram: https://www.instagram.com/getmobly/

LinkedIn: https://www.linkedin.com/in/zachbarney/

LinkedIn: https://www.linkedin.com/company/getmobly/

Think you'd be a great guest on the show? Apply https://go.intellectualstrategies.com/

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 breakdowns, expensive partnerships, capital pressure, and the personal weight of keeping people employed in a rural community.

When COVID disrupted overseas suppliers, Spencer didn’t wait for things to “normalize.” He built Merit3D to solve a real operational problem... speed. Using additive manufacturing, his team helps companies skip long lead times, avoid tooling delays, and keep production in the U.S. without sacrificing quality.

Spencer is clear-eyed about the struggle. Growth creates pressure. Leadership compounds risk. And success rarely feels stable while you’re in it. But with the right operating mindset and a team that can execute, manufacturing in the U.S. can still win.

If you’re a CEO, founder, or operator thinking about scale, supply chain risk, or bringing production closer to home, this episode offers grounded insight from someone actively doing the work. This conversation isn’t about trends or theory. It’s about decisions.

🎧 Listen to the full episode to hear the nuance behind the decisions and why Spencer still believes the future of manufacturing belongs here.

Check out Spencer's work at https://merit3d.com/.

Say hello to Spencer!

LinkedIn: https://www.linkedin.com/in/spencer-loveless/

Facebook: https://www.facebook.com/Merit3D/

Instagram: https://www.instagram.com/merit3d/

LinkedIn: https://www.linkedin.com/company/merit-3d/

YouTube: https://www.youtube.com/@Merit-3D/

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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 business and where CEOs still have to step in and decide.

Lou has built and advised small and mid-sized businesses through multiple disruptions, from 9/11 to financial crises to the pandemic. His perspective is shaped by operating when capital tightens, banks pull back, and clean answers don’t exist. That experience informs how he thinks about AI, cash flow, and resilience today.

The conversation centers on a simple reality that many CEOs are living right now. Tools are more powerful than ever, but businesses still fail when leaders confuse automation with judgment. AI can help organize the ingredients, but CEOs still decide what gets cooked, what gets scrapped, and when it’s time to pivot.

This episode is for CEOs and founders who are navigating uncertainty, experimenting with AI, and trying to scale without losing control of the fundamentals. It’s a grounded conversation about decision-making, resilience, and why leadership judgment still compounds when everything else levels out.

Listen to the full episode of The Breakout CEO for a candid, operator-level discussion on scaling through chaos without outsourcing your judgment.

Check out Lou's work at https://www.shieldadvisorygroup.com/ and https://creditbanc.io/.

Say hello to Luigi!

LinkedIn: https://www.linkedin.com/in/luigi-rosabianca/

Enclosed is also a copy of his book (free audio version), Buying The American Dream - A Strategic Playbook for Acquiring Small Businesses. https://drive.google.com/file/d/1iCSh0yb8PrwKFo0AZnpjV4Z84YZj2Elx/view

If you want a paper copy, it’s also available on Amazon. http://bit.ly/3ZwSHnz.

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 leadership becomes harder as companies scale, not easier, and why many CEOs underestimate the operational cost of misalignment until it’s already doing damage. She also breaks down how “blue sky thinking” actually works inside real companies: not as vision work, but as a way to surface options teams stop seeing once constraints harden.

The discussion also addresses a reality many CEOs quietly face; isolation at the top, decision-making without certainty, and the internal weight of responsibility when outcomes rest on a few calls made under imperfect conditions.

If you’re building, scaling, or resetting a company and carrying the weight that comes with it, this one’s for you.

Check out Cydni's work at https://www.swirecocacola.com/.

Say hello to Cydni!

LinkedIn: https://www.linkedin.com/in/cydnitetro/

Facebook: https://www.facebook.com/cydtetro/

Instagram: https://www.instagram.com/cydtetro/

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 to build.

The discussion traces Tom’s path through product development, global manufacturing, and consumer electronics, leading to the creation of Paleblue batteries and its focus on eliminating single-use battery waste. Along the way, Tom breaks down the real challenges of hardware entrepreneurship, from supply chain complexity to fundraising during market shocks, and why progress often comes from simply staying in the fight longer than others.

This episode offers practical insight for CEOs and founders navigating long build cycles, uncertain markets, and decisions that test personal conviction.

If you are building something you believe in and need a reminder of why staying in the course matters, this conversation delivers clarity without gloss.

Check out Tom's work at https://paleblueearth.com/.

Say hello to Tom!

LinkedIn: https://www.linkedin.com/in/thomas-bishop-bb67267/

Instagram: https://www.instagram.com/pale_blue_earth/

https://www.linkedin.com/company/pale-blue-earth/

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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 lasting value: tightening margin discipline, aligning incentives, understanding true profitability, and building leadership capacity that can carry the business forward.

If you’re leading a scaling company and feel the tension between growth targets and operational reality, this episode speaks directly to the strategic shifts' CEOs have to make to break through to the next level.

Check out Dan's work at https://winktoolbox.com/ & https://bdexperts.com/.

Say hello to Dan!

Facebook: https://www.facebook.com/blackdiamondexperts

Instagram: https://www.instagram.com/bdexperts/

LinkedIn: https://www.linkedin.com/in/daniel-james-b2716022/

https://www.linkedin.com/company/blackdiamondexperts/

https://www.linkedin.com/company/wink-reports/

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