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The Breakout CEO: Inside the Strategic Moves of Scaling CEOs

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.
APPLY TO BE A GUEST
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.
Subscribe & Listen
Episode 056 (Season 3)

How CEOs Build Companies by Solving Problems They Don’t Understand Yet

with Dusty Gulleson, Tectonic

Scaling CEOs grow by committing before clarity and building the capability to solve problems under pressure, rather than waiting for full understanding.
LISTEN TO THIS EPISODE
Episode 055 (Season 3)

Why Smart CEOs Still Make Bad Decisions Under Pressure

with William Holsten, Think Smartly

Most CEO decision failures stem not from poor strategy, but from degraded decision environments—conditions that can be diagnosed and mitigated with simple frame
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Episode 054 (Season 3)

The Three-Part Decision Framework CEOs Need to Cut Through Noise

with Dr. Christiane Schroeter

A three-part framework for CEOs to improve decision clarity, accelerate execution, and maintain momentum under uncertainty. Read more from Dr. Christiane Schroe
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Episode 053 (Season 3)

Diagnose Before You Scale: The CEO Discipline Most Skip

with Jon Bassford, Lateral Solutions

Scaling problems rarely come from lack of effort. Jon Bassford explains why CEOs must diagnose operational and leadership breakdowns before adding resources.
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Episode 052 (Season 3)

The Moment You Realize Your Product Isn’t the Business Model

with Maísa Benatti, AIUTA

Even strong product traction can conceal a broken business model. This post examines how CEOs must interpret signal vs. noise before scaling locks in the wrong
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Episode 051 (Season 3)

The Cost of Getting Comfortable Too Early as a Scaling CEO

with Laurent Cohen, GetOblic

Early success can hide structural risk. Laurent Cohen explains how comfort, not failure, nearly broke his business—and what CEOs must do differently. Read more.
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Episode 050 (Season 3)

How Josh Carr Rebuilt Echo Water Into an $18M Hardware Company

with Josh Carr, Echo Water

As AI makes software easier to replicate, Echo Water CEO Josh Carr argues durable businesses may increasingly come from harder-to-build hardware companies.
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Episode 049 (Season 2)

The Cost of Scaling a Marketplace With Misaligned Incentives

with Paul Roberts, GoodBite

Marketplace companies often fail when stakeholder incentives drift apart. Check out Paul Roberts' explanation on why alignment must exist before scale begins.
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Episode 048 (Season 2)

The Leadership Shift That Took This CEO From Survival to Scale

with Michael Chaput, Endsight

Scaling a services business is harder than it looks. Michael Chaput scaled Endsight to $35M and shares his lessons from failure and leadership ceilings.
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Episode 047 (Season 2)

The Moment CEOs Realize Their Company Is Too Complicated

with Alex Sanfilippo, PodMatch

A founder grows through opportunity until the market becomes confused. Alex Sanfilippo explains the leadership decision to simplify and refocus the business.
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