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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 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.
LISTEN TO THIS EPISODE
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.
LISTEN TO THIS EPISODE
Episode 042 (Season 2)

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
LISTEN TO THIS EPISODE
Episode 041 (Season 2)

Why Product-Market Fit Doesn't Guarantee Funding

with Meghan Higney, Message

Even strong product-market fit may not unlock capital. Meghan Higney explains why consumer founders must adapt strategy to the working-capital realities of scal
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Episode 040 (Season 2)

The Moment CEOs Choose Between Growth and Standards

with Chris Shurian, Bootstraps and Battle Scars

When companies scale, CEOs must decide whether to pursue every revenue opportunity or protect the standards that define their brand. Listen to this episode.
LISTEN TO THIS EPISODE
Episode 039 (Season 2)

Persevere or Pivot: The Founder's Hardest Call

with John Cousins, MBA ASAP

A CEO’s judgment call between perseverance and pivot: examining control, feedback loops, and how time increases your luck surface area. Listen to this episode.
LISTEN TO THIS EPISODE
Episode 038 (Season 2)

When Authority Erodes, Pricing Power Disappears

with Dennis Meador, The Legal Podcast Network

In commoditized markets, pricing pressure often reflects authority erosion. Dennis Meador explains why founder-led visibility protects margin and positioning.
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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.
LISTEN TO THIS EPISODE

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