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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.
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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 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 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 043 (Season 2)

Advisory Insights: Finding and Fixing Executive Leadership Misalignment in a Scaling Business

with Jeff Holman, Intellectual Strategies

Jeff introduces the Advisory Insights series and explains why leadership misalignment is one of the most common causes of stalled growth in scaling companies.
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Episode 046 (Season 2)

The Real Cost of Executive Misalignment in Scaling Companies

with Robert White, Extraordinary People

Executive misalignment often appears as people problems. Robert White explains why unclear and unenforced purpose, vision, and values quietly drain a CEO’s time
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Episode 045 (Season 2)

The Moment a CEO Must Choose Between Control and Scale

with Ral West, Ral West Livin' The Dream

Scaling often stalls when a founder remains operationally indispensable. Ral West explains why growth accelerates only after a CEO shifts control into culture,
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Episode 044 (Season 2)

The Warning Signs CEOs are Scaling Complexity instead of Structure

with Derek Fredrickson, The COO Solution

Scaling companies often mistake growth activity for operational progress. Derek Fredrickson explains why structure—not complexity—is what actually enables scale
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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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