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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.
Subscribe & Listen
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.
LISTEN TO THIS EPISODE
Episode 034

When CEOs Must Choose Between Conviction and Consensus

with Shay Levi, CEO of Unframe

Scaling CEOs learn to act on conviction, using firsthand market signals to lead in fast-forming industries, even before consensus from the team is available.
LISTEN TO THIS EPISODE
Episode 033

The Decision That Separates CEOs Who Quit from Those Who Rebuild

with Keith Norris, KPI Fire

When a company hits real constraints, the line between quitting and rebuilding comes down to a single decision a CEO must make without certainty under pressure.
LISTEN TO THIS EPISODE
Episode 032

The Revenue Risk When CEOs Say “We Can’t Measure Event ROI”

with Zach Barney, Mobly

Unmeasured in-person marketing spend creates hidden revenue and capital risk. Zach Barney explains why delayed ROI discipline forces painful leadership resets.
LISTEN TO THIS EPISODE
Episode 031

When a $4 Part Forces a CEO Into a Total Operating Reset

with Spencer Loveless, Merit3D

A minor supply chain failure exposed structural operating risk, forcing a CEO to reset control over speed, production, and decision-making under pressure.
LISTEN TO THIS EPISODE
Episode 030

Scaling Through Constraint: Capital, Cash Flow, and Resilient Execution

with Lou Rosabianca, Sheild Advisory Group

Lou Rosabianca explains why working capital is an operating decision, how resilient CEOs pivot through shocks, and what financial discipline enables scale.
LISTEN TO THIS EPISODE
Episode 029

People-Centered Leadership and Blue Sky Thinking

Cydni Rogers Tetro

Cydni Tetro discusses people-centered leadership, blue sky thinking, resilience, and how creative problem-solving drives innovation and business success.
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Episode 028

Building a Mission-Driven Hardware Company in a Disposable World

with Tom Biship, CEO of Paleblue

Blending mission-first thinking, sustainability, and product manufacturing discipline can transform a disposable hardware category into a scalable business.
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Episode 027

Scaling a Home Services Company to $30M: Pricing, Leadership, and the Path to Private Equity

with Dan James, Former CEO of Black Diamond Experts

Learn how a home services business scaled to $30M by repricing for EBITDA, building leadership systems, and preparing for a private equity exit strategy.
LISTEN TO THIS EPISODE
Episode 026

Designing a Business Buyers Will Actually Acquire

with Andrew Gazdecki, Acquire.com

A practical look at how founders design businesses for acquisition, avoid stalled exits, and create a clear, buyer-ready sale process without operational drag.
LISTEN TO THIS EPISODE

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