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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 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.
LISTEN TO THIS EPISODE
Episode 087 (Season 4)

The Strategic Altitude Every Scaling CEO Needs

with Logan McKnight, GoodKnight Consulting

As companies scale, CEOs must move beyond day-to-day execution. Logan McKnight shares a practical framework for building ownership, accountability, and the stra
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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 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 084 (Season 4)

The CEO Playbook for Building Trust Before You Build Demand

with Romney Williams, DRYOUT

Romney explains why lasting growth begins with trust, customer discovery, and disciplined strategic pivots—not simply better products or intellectual property.
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Episode 083 (Season 4)

The Founder Lesson That Every CEO Should Hear About Customer Feedback

with Julie Tylman, GroupTogether

Learn how GroupTogether founder Julie Tylman used customer feedback to shape product decisions, build trust, and drive sustainable business growth. Read more.
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Episode 082 (Season 4)

Why AI Won't Replace Great Real Estate Professionals

with Sheldon Wolf, Intellitary AI

AI is transforming real estate, but not by replacing professionals. Sheldon Wolf explains why long-term competitive advantage belongs to companies that adopt te
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Episode 081 (Season 4)

Why Speed Beats Perfection in Healthcare Startups

with Seth Merritt, Welby Health

Discover why Welby Health CEO Seth Merritt believes speed, customer feedback, and disciplined execution outperform perfection when scaling a startup. Learn more
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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 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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