The Breakout CEO

By Jeff Holman, Fractional General Counsel for CEOs and Founders

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Category: Entrepreneurship

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Episodes: 106

Description

The Breakout CEO is a CEO podcast for scaling CEOs and founders, hosted by Jeff Holman. In each episode, a growth-stage CEO shares the real decisions behind scaling a business, from hiring and leadership to pivots and revenue growth. These founder interviews focus on companies in the $5M to $50M range and the business growth strategies that moved them from startup to scale-up. Every conversation centers on an inflection point: the moment a company outgrew its old way of working and the CEO had to choose a new one. Guests explain what they decided and what they would do differently. Recent topics include panic hiring, AI adoption, hidden revenue leaks, and building trust before building demand. Jeff Holman is the founder of Intellectual Strategies, where he works as outside general counsel to scaling CEOs and founders on strategy, governance, and risk during rapid growth. He brings that operator-level view to each interview. Be a guest: We feature a limited number of CEOs and founders with first-hand breakout stories. Apply at https://go.intellectualstrategies.com/ Media and event partnerships: For press access, on-site recording, or event collaboration, contact us through intellectualstrategies.com/podcast.

Episode Date
106 - Hand Off Technology and Your Growth Stalls
Oct 29, 2026
105 - The $2M Never Came. The CEO Fired Everyone
Oct 22, 2026
104 - The Real Reason Scaling CEOs Keep Panic Hiring
Oct 16, 2026
103 - The Hidden Profits Framework: Why Resourcefulness Beats Resources for Scaling CEOs
Oct 15, 2026
102 - The One Question To Ask Before Any Brand Decision
Oct 14, 2026
101 - What The Elevator Man Can Teach CEOs About AI Adoption
Oct 13, 2026
100 - The Part of Your CEO Story You're Skipping
Oct 12, 2026
99 - The Growth That Was Eating Your Best Product
Oct 01, 2026
98 - The Sales Trick That Nearly Ended a Founder's Career
Sep 24, 2026
97 - Why The Real Revenue Leak Is Rarely Where CEOs Look
Sep 18, 2026
96 - The Framework Hiding Inside Every Founder's Head
Sep 17, 2026
95 - Why Financial Success And Self-Worth Are Not The Same Thing
Sep 16, 2026
94 - Why Presence Is the Multiplier That Determines How Far You Rise
Sep 15, 2026
93 - How a $30,000 Monthly Loss Forced a Founder to Rethink His Leadership
Sep 01, 2026
92 - How OneMeta's Stalled Six-Figure Contract Grew into Eight-Figure Revenue
Aug 27, 2026
91 - Why George Hartley Built Nitrosend Without a Dashboard
Aug 25, 2026
90 - The 90-day Reset Framework Advisors Use to Get Stalled Companies to Version 2.0
Aug 21, 2026
89 - The Three-Step Framework That Makes Hard Team Conversations Easier
Aug 20, 2026
88 - Why Vision Beats Motivation When Scaling a Business
Aug 19, 2026
87 - The Strategic Altitude Every Scaling CEO Needs
Aug 18, 2026
86 - The Pivot This Founder Made After an Investor Called It Impossible
Aug 13, 2026
85 - The CEO Who Set Out to Change Policing Without Using More Force
Aug 11, 2026
84 - The CEO Playbook for Building Trust Before You Build Demand
Aug 06, 2026
83 - The Founder Lesson That Every CEO Should Hear About Customer Feedback
Aug 04, 2026
82 - Why AI Won't Replace Great Real Estate Professionals
Jul 30, 2026
81 - Why Speed Beats Perfection in Healthcare Startups
Jul 23, 2026
80 - The Signals CEOs Miss Before Growth Breaks Their Team
Jul 16, 2026
79 - The Leadership Shift That Helped Build a Billion-Dollar Company
Jul 09, 2026
78 -Why Most Service Companies Sell the Wrong Thing
Jul 02, 2026
77 - How Better Hiring Decisions Create Better Companies
Jun 30, 2026
76 -When Market Signals Are Strong Enough to Go All In
Jun 25, 2026
75 - The Leadership Skill Most CEOs Undervalue: Human Connection
Jun 23, 2026
74 - The Inventory Signals Advisors Spot Before CEOs Do
Jun 18, 2026
73 - The Cash Flow Mistake Most Founders Don’t Realize They’re Making
Jun 17, 2026
72 - Why Investor Trust Matters More Than Your Pitch Deck
Jun 16, 2026
71 - The Decision to Reinvest Instead of Cash Out
Jun 11, 2026
70 - Why Most Startup Support Systems Fail Founders
Jun 09, 2026
69 - The Hardest Part of Scaling Is Rebuilding the Team
Jun 04, 2026
68 - Why Manufacturing CEOs Can’t Wait to Adopt AI Infrastructure
Jun 02, 2026
67 - The Leadership Signals CEOs Miss About Themselves First
May 28, 2026
66 - The Labor Cost Signal CEOs Start Tracking Too Late
May 26, 2026
65 - What Hidden Stress Reveals About a CEO’s Decision Quality
May 21, 2026
64 - What CEOs Miss When They Think They’ve Already Scaled
May 19, 2026
63 - The Cost of Waiting Too Long on a High-Stakes Decision
May 14, 2026
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