The Breakout CEO Podcast | Intellectual Strategies

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.

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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 049

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 050

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 047

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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Episode 048

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 046

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

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

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 043

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 042

Why Smart CEOs Design Their Exit Long Before They Sell

with Draven McConville, Klipboard

Building a company that can be sold later requires years of operational discipline, traction, and systems that allow the business to function beyond the founder

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Episode 024

How The Queen of Wraps Scaled to Success: Loss Leaders, Capacity, and Margin Control

with Heather Griffith Barber, Buy Scale Sell

Explore how "The Queen of Wraps" scaled an exit-ready business by using loss leaders, smart capacity bets, and vertical integration to protect margins.

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The Breakout CEO: Inside the Strategic Moves of Scaling CEOs

The Cost of Scaling a Marketplace With Misaligned Incentives

with Paul Roberts, GoodBite

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

with Josh Carr, Echo Water

The Moment CEOs Realize Their Company Is Too Complicated

with Alex Sanfilippo, PodMatch

The Leadership Shift That Took This CEO From Survival to Scale

with Michael Chaput, Endsight

The Real Cost of Executive Misalignment in Scaling Companies

with Robert White, Extraordinary People

The Moment a CEO Must Choose Between Control and Scale

with Ral West, Ral West Livin' The Dream

The Warning Signs CEOs are Scaling Complexity instead of Structure

with Derek Fredrickson, The COO Solution

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

with Jeff Holman, Intellectual Strategies

Why Smart CEOs Design Their Exit Long Before They Sell

with Draven McConville, Klipboard

How The Queen of Wraps Scaled to Success: Loss Leaders, Capacity, and Margin Control

with Heather Griffith Barber, Buy Scale Sell

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