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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 103 (Season 5)

The Hidden Profits Framework: Why Resourcefulness Beats Resources for Scaling CEOs

With Stacey Hylen

A business coach's resourcefulness framework shows CEOs how to unlock revenue already sitting inside existing clients—without new spend. Learn more here.
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Episode 102 (Season 5)

The One Question To Ask Before Any Brand Decision

With Kevin Perlmutter

A business coach's resourcefulness framework shows CEOs how to unlock revenue already sitting inside existing clients—without new spend. Learn more here.
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Episode 101 (Season 5)

What The Elevator Man Can Teach CEOs About AI Adoption

with Bryant Oberg, Human Co-Pilot

Why AI adoption stalls at scale isn't a technology problem — it's a governance gap. An advisor's framework for CEOs on policy and trust. Learn more here.
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Episode 100 (Season 5)

The Part of Your CEO Story You're Skipping

with Jeff Holman, The Breakout CEO

A CEO story missing a stage is missing a piece. The Breakout Arc, drawn from 62 CEO conversations, shows how to tell a hard decision so it lands. Read more here
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Episode 099 (Season 5)

The Growth That Was Eating Your Best Product

with Jared Shepard, Hypori

Jared Shepard on why a product line can't grow inside a services company — and the spin-out decision that built Hypori. Read the full article and learn more.
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Episode 098 (Season 4)

The Sales Trick That Nearly Ended a Founder's Career

with Larry Gould, TheBigWord

A hidden expense workaround nearly cost Larry Gould his job — and became the origin of one of the world's largest language companies. Read more about Larry.
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Episode 097 (Season 4)

Why The Real Revenue Leak Is Rarely Where CEOs Look

with Kati Peterman, YourFRX

Kati Peterman's diagnostic method shows why scaling CEOs misread revenue loss as a sales problem when operations is the real leak. Read more from the article.
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Episode 096 (Season 4)

The Framework Hiding Inside Every Founder's Head

with Simon Bowen, Models Method

Simon Bowen argues the real differentiator scaling companies lose isn't their why — it's the founder's original thinking, uncaptured and diluted. Read more.
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Episode 095 (Season 4)

Why Financial Success And Self-Worth Are Not The Same Thing

with Louis Swart

A CEO advisor's framework for the hidden belief that quietly blocks delegation, trust, and internal peace at scale. Read more about the pattern Louis describes
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Episode 094 (Season 4)

Why Presence Is the Multiplier That Determines How Far You Rise

With Mike Acker, Up Level Communication

A CEO's execution and presence rarely scale together. Mike Acker on why the gap between them becomes the real ceiling on growth. Read more about the advisor.
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