Let's chat!
Click HERE to book a call

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 076 (Season 3)

When Market Signals Are Strong Enough to Go All In

with Arthur Jessop, Base Case

Arthur shares how he learned to distinguish curiosity from genuine demand and why waiting for certainty can become a greater risk than moving forward without it
LISTEN TO THIS EPISODE
Episode 075 (Season 3)

The Leadership Skill Most CEOs Undervalue: Human Connection

with Richard Blank, Costa Rica's Call Center

As companies scale, leaders often strengthen systems while weakening relationships. Richard Blank explains why human connection remains a durable leadership adv
LISTEN TO THIS EPISODE
Episode 074 (Season 3)

The Inventory Signals Advisors Spot Before CEOs Do

with Alex Hennick

Alex Hennick explains why inventory stress often reveals deeper operational and financial problems before CEOs clearly recognize the underlying issue.
LISTEN TO THIS EPISODE
Episode 073 (Season 3)

The Cash Flow Mistake Most Founders Don’t Realize They’re Making

with Brandon Neely, Counterflow

Brandon explains why many founders mistake revenue growth for financial resilience — and how liquidity, capital access, and cash flow mechanics shape survival.
LISTEN TO THIS EPISODE
Episode 072 (Season 3)

Why Investor Trust Matters More Than Your Pitch Deck

with George Dubec, America's Real Deal

George Dubec explains why investor credibility, visibility, networking, and AI-driven communication matter more than polished pitch decks for scaling CEOs seeki
LISTEN TO THIS EPISODE
Episode 071 (Season 3)

The Decision to Reinvest Instead of Cash Out

with Lindsey Prater, Groovy Peach

Lindsey Prater grew Groovy Peach into a multi-location, multi-million-dollar business by prioritizing retained earnings, disciplined expansion, and culture ove
LISTEN TO THIS EPISODE
Episode 070 (Season 3)

Why Most Startup Support Systems Fail Founders

with Gregory Shepard, Startup Science

Gregory Shepard explains why fragmented startup support systems create founder failure — and why lifecycle clarity and operational coordination matter more as A
LISTEN TO THIS EPISODE
Episode 069 (Season 3)

The Hardest Part of Scaling Is Rebuilding the Team

with Drew Allen, Grace Technologies

Drew Allen explains why scaling often requires rebuilding the leadership team, raising organizational standards, and creating a culture of ownership.
LISTEN TO THIS EPISODE
Episode 068 (Season 3)

Why Manufacturing CEOs Can’t Wait to Adopt AI Infrastructure

with Torian Richardson, DBR77

Torian Richardson explains why manufacturing CEOs must treat AI adoption as an operational leadership decision before delayed adaptation compounds into competit
LISTEN TO THIS EPISODE
Episode 067 (Season 3)

The Leadership Signals CEOs Miss About Themselves

with Jane Monroe, Embrace the Grape

Jane Monroe explains how self-awareness, delegation, and cultural discipline shape leadership decisions as companies scale under pressure. Read more here.
LISTEN TO THIS EPISODE

GET SMART LEGAL INSIGHTS STRAIGHT TO YOUR INBOX

Sign up for our upcoming newsletter!
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.
Intellectual Strategies © 2025