The Breakout CEO

By Jeff Holman

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Category: Entrepreneurship

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Episodes: 62

Description

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 here: https://go.intellectualstrategies.com/ 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.

Episode Date
62 - What Happens When CEOs Delay AI Adoption in Engineering Teams
May 12, 2026
61 - The Moment CEOs Realize They’ve Become the Bottleneck
May 07, 2026
60 - What Happens When CEOs Optimize for Scale Over Trust
May 05, 2026
59 - What Happens When CEOs Ignore Cyber Risk in an AI-Driven World
Apr 30, 2026
58 - The Customer Concentration Risk CEOs See Too Late
Apr 28, 2026
57 - The Hidden Cost of Building Blind in Product Development
Apr 23, 2026
56 - How CEOs Build Companies by Solving Problems They Don’t Understand Yet
Apr 21, 2026
55 - Why Smart CEOs Still Make Bad Decisions Under Pressure
Apr 16, 2026
54 - The Three-Part Decision Framework CEOs Need to Cut Through Noise
Apr 15, 2026
53 - Diagnose Before You Scale: The CEO Discipline Most Skip
Apr 14, 2026
52 - The Moment You Realize Your Product Isn’t the Business Model
Apr 09, 2026
51 - The Cost of Getting Comfortable Too Early as a Scaling CEO
Apr 07, 2026
50 - How Josh Carr Rebuilt Echo Water Into an $18M Hardware Company
Apr 02, 2026
49 - The Cost of Scaling a Marketplace With Misaligned Incentives
Mar 31, 2026
48 - The Leadership Shift That Took This CEO From Survival to Scale
Mar 26, 2026
47 - The Moment CEOs Realize Their Company Is Too Complicated
Mar 24, 2026
46 - The Real Cost of Executive Misalignment in Scaling Companies
Mar 19, 2026
45 - The Moment a CEO Must Choose Between Control and Scale
Mar 18, 2026
44 - The warning signs CEOs are scaling complexity instead of structure
Mar 17, 2026
43 - Advisory Insights: Finding and Fixing Executive Leadership Misalignment in a Scaling Business
Mar 16, 2026
42 - Why Smart CEOs Design Their Exit Long Before They Sell
Mar 12, 2026
41 - Why Product-Market Fit Doesn’t Guarantee Funding
Mar 10, 2026
40 - The Moment CEOs Choose Between Growth and Standards
Mar 05, 2026
39 - Persevere or Pivot: The Founder’s Hardest Call
Mar 03, 2026
38 - When Authority Erodes, Pricing Power Disappears
Feb 26, 2026
37 - The CEO Decision to Stop Competing and Redefine the Market
Feb 24, 2026
36 - Licensing or Operating: The CEO’s Inflection Point
Feb 20, 2026
35 - Choosing Legacy Over Lifestyle After a Billion-Dollar Exit
Feb 17, 2026
34 - When CEOs Must Choose Between Conviction and Consensus
Feb 12, 2026
33 - The Decision That Separates CEOs Who Quit From Those Who Rebuild
Feb 10, 2026
32 - The Revenue Risk When CEOs Say “We Can’t Measure Event ROI"
Feb 05, 2026
31 - When a $4 Part Forces a CEO Into a Total Operating Reset
Feb 03, 2026
30 - When CEOs Must Decide What AI Does and What It Never Should
Jan 29, 2026
29 - What Happens When CEOs Tolerate Misalignment Too Long
Jan 27, 2026
28 - The Hidden Complexity Behind “Simple” Consumer Products
Jan 22, 2026
27 - Replacing Hustle with EBITDA as the Real Scorecard
Jan 20, 2026
26 - The Real Truth About Selling a SaaS Business and Why Most Founders Get It Wrong
Jan 15, 2026
25 - The Leadership Shift That Unlocks Breakout Growth (Most CEOs Learn It Too Late)
Jan 13, 2026
24 - What It Takes for Women Founders to Build Companies Buyers Trust
Jan 08, 2026
23 - Why CEOs Need to Choose Calculated Risk Over Playing It Safe
Jan 06, 2026
22 - Scaling Exposes This Leadership Weakness Every Founder Has
Dec 30, 2025
21 - The Leadership Blind Spots That Create Avoidable Problems
Dec 23, 2025
20 - When CEOs Stop Listening: Early Warning Signs Your Business Is Scaling the Wrong Way
Dec 18, 2025
19 - The Unconscious CEO Habits That Are Holding Back Your Growth
Dec 16, 2025
18 - When Survival Turns into Strategy: The Breakout Shift Every CEO Needs
Dec 11, 2025
17 - The Hidden Spiral Pattern Behind Fast-Growth Companies
Dec 09, 2025
16 - The CEO Advantage No One Tracks: Understanding Your People Better Than Your Competitors Do
Dec 04, 2025
15 - Your Story Is Your Strategy: Why Most CEOs Miss It
Dec 02, 2025
14 - Preventing Burnout: The EQ Approach Every CEO Needs Now
Nov 29, 2025
13 - Fractional COO Explained: The Role That Transforms Scaling Companies
Nov 13, 2025
12 - From Bankruptcy to Industry Leader: The Mindset That Changed It All
Nov 11, 2025
11 - From the Navy to Medical Innovation: A Journey of Persistence and Purpose with Healionics Corporation's Mike Connolly
Nov 05, 2025
10 - Building with Heart: How Culture and Collaboration Drive Unlikely Success with Aspen Mountain Partners' Greg Schow
Oct 29, 2025
9 - How Curiosity Drives Innovation: Leadership Strategies for Growth with INSEAD's Spencer Harrison
Oct 22, 2025
8 - The Importance of a Strong Foundation: Why Resilience Matters in Product Development with Product 1's Steven Selikoff
Oct 15, 2025
7 - Resilience at the Crossroads: CEO Insights from Design and Logistics with Shyft's Alex Burdge
Oct 01, 2025
6 - Persistence in Action: Redefining the Fintech Landscape with ASA's Landon Glenn
Sep 24, 2025
5 - Pivoting in the Face of Adversity: Lessons from a Tech Leader’s Journey with Intel Corporation's Dr. Darren Pulsipher
Sep 17, 2025
4 - Smart Strategies for a Thriving Software Development Business with DevSquad's Phil Alves
Sep 10, 2025
3 - The Rollercoaster of Entrepreneurship: Embracing Ups and Downs for Growth with Startup Ignition Academy's John Richards
Sep 03, 2025
2 - Cash Flow and Innovation: Strategies for Sustainable Growth in High ASP Markets with SubcontractorHub's Justin Brach
Aug 27, 2025
1 - From Crisis to Confidence: Unleashing the Breakout CEO Within with Jeff Holman
Aug 20, 2025