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 105 (Season 5)

The $2M Never Came: Why Asaf Chose to Bootstrap Instead of Raising Again

with Asaf Darash, Regpack

When a $2M angel commitment collapsed, Asaf cut Regpack to three people and bootstrapped until the technology was proven. The decision logic and its cost.

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Episode 085 (Season 4)

The CEO Who Set Out to Change Policing Without Using More Force

with Scot Cohen, Wrap Technologies

Many CEOs eventually encounter a more difficult question: What happens when you've achieved everything you set out to accomplish and knew it isn't enough?

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Episode 079 (Season 4)

The Leadership Shift That Helped Build a Billion-Dollar Company

with Vikas Sehgal, HyperDart

Learn from Vikas Sehgal of HyperDart why scaling CEOs succeed by enabling great people, aligning around shared values and solving customer problems...

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Episode 086 (Season 4)

The Pivot This Founder Made After an Investor Called It Impossible

with Jevon Le Roux, Keeyu

In this episode, Jevon breaks down why customer service has been built backward. Here's the decision logic he used to pivot Keeyu and prove him wrong.

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Episode 080 (Season 4)

The Signals CEOs Miss Before Growth Breaks Their Team

with David Khim, Omniscient Digital

David Khim explains why the earliest signs of growth constraints appear in team capacity, founder behavior, and qualitative leadership signals long before trad

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Episode 078 (Season 4)

Why Most Service Companies Sell the Wrong Thing

with Mike LaVista, Caxy

Mike LaVista explains why service companies grow faster when they stop selling services and instead communicate the business problems they solve. Read more.

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Episode 077 (Season 3)

How Better Hiring Decisions Create Better Companies

with Fletcher Wimbush, Discovered.ai

Fletcher Wimbush explains why hiring is a strategic CEO responsibility, how disciplined talent decisions shape culture and execution, and why focus—not complexi

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Episode 090 (Season 4)

The 90-day Reset Framework Advisors Use to Get Stalled Companies to Version 2.0

with Diane Moura, ZenChange Marketing

Advisor Diane Moura's diagnostic reset shows why stalled growth is a structure problem, not a strategy problem — and how CEOs fix it in 90 days. Learn more.

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Episode 092 (Season 4)

How OneMeta's Stalled Six-Figure Contract Grew Into Eight-Figure Revenue

with Saul Leal, One Meta

A stalled six-figure enterprise deal taught OneMeta's CEO to diagnose bureaucracy instead of blaming his team or the client. Learn more from this article.

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Episode 088 (Season 4)

Why Vision Beats Motivation When Scaling a Business

with Rael Bricker

Rael Bricker's RISE Framework shows scaling CEOs why motivation fades and how vision, strengths, and delegation build execution that lasts. Read more.

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The Breakout CEO: Inside the Strategic Moves of Scaling CEOs

The $2M Never Came: Why Asaf Chose to Bootstrap Instead of Raising Again

with Asaf Darash, Regpack

The CEO Who Set Out to Change Policing Without Using More Force

with Scot Cohen, Wrap Technologies

The Leadership Shift That Helped Build a Billion-Dollar Company

with Vikas Sehgal, HyperDart

The Pivot This Founder Made After an Investor Called It Impossible

with Jevon Le Roux, Keeyu

The Signals CEOs Miss Before Growth Breaks Their Team

with David Khim, Omniscient Digital

Why Most Service Companies Sell the Wrong Thing

with Mike LaVista, Caxy

How Better Hiring Decisions Create Better Companies

with Fletcher Wimbush, Discovered.ai

The 90-day Reset Framework Advisors Use to Get Stalled Companies to Version 2.0

with Diane Moura, ZenChange Marketing

How OneMeta's Stalled Six-Figure Contract Grew Into Eight-Figure Revenue

with Saul Leal, One Meta

Why Vision Beats Motivation When Scaling a Business

with Rael Bricker

STRATEGIC MOVES OF SCALING CEOs, IN YOUR INBOX