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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 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 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 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
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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.
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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.
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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 037 (Season 2)

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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