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 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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Episode 011

The Relentless Pursuit of Innovation: Mike Connolly on Building Breakthrough Medical Devices

with Mike Connolly, Healionics

In this episode, Mike Connolly of Healionics shares what it takes to turn scientific innovations into lasting clinical impact and meaningful patient outcomes.

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Episode 037

The CEO Decision to Stop Competing and Redefine the Market

with Andrew Ackerman, Second Century Ventures

When Dreamit Accelerator found itself stuck behind dominant competitors, the pivotal decision was whether to keep racing on the same track at all. Watch now.

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Episode 036

Licensing or Operating: The CEO’s Inflection Point

with Jeff Doss, Beach Bags

When intended distribution partners hesitate and licensing stalls, a CEO must decide whether to start a company himself and assume operational risk or not.

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Episode 035

Choosing Legacy Over Lifestyle After a Billion-Dollar Exit

with Sal Rehmetullah, Worth AI

After a billion-dollar exit, Sal Rehmetulla and his sister chose reinvention over retirement to help modernize small business financing infrastructure.

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Episode 025

When the Cold Breaks: Nikky Kho on Building Businesses, Forgiveness, and Seeing the Peak

with Nikky Kho, Self Mastery

What does trekking to Everest Base Camp have to do with building companies, pioneering AI, and surviving six-figure setbacks? For Nikky Kho, everything.

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Episode 041

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

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.

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Episode 039

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.

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The Breakout CEO: Inside the Strategic Moves of Scaling CEOs

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

The Relentless Pursuit of Innovation: Mike Connolly on Building Breakthrough Medical Devices

with Mike Connolly, Healionics

The CEO Decision to Stop Competing and Redefine the Market

with Andrew Ackerman, Second Century Ventures

Licensing or Operating: The CEO’s Inflection Point

with Jeff Doss, Beach Bags

Choosing Legacy Over Lifestyle After a Billion-Dollar Exit

with Sal Rehmetullah, Worth AI

When the Cold Breaks: Nikky Kho on Building Businesses, Forgiveness, and Seeing the Peak

with Nikky Kho, Self Mastery

Why Product-Market Fit Doesn't Guarantee Funding

with Meghan Higney, Message

The Moment CEOs Choose Between Growth and Standards

with Chris Shurian, Bootstraps and Battle Scars

Persevere or Pivot: The Founder's Hardest Call

with John Cousins, MBA ASAP

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