Shows / The Breakout CEO
The Breakout CEO
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…
Episodes
- The Breakout CEO
46 - The Real Cost of Executive Misalignment in Scaling Companies
Most CEOs don’t notice executive misalignment when it starts. They notice it when they’re spending 70–80% of their time on people problems. In this Advisory…
- The Breakout CEO
45 - The Moment a CEO Must Choose Between Control and Scale
Most scaling CEOs say they want growth. Fewer are willing to confront the moment when growth requires them to give up control. In this Advisory Insight…
- The Breakout CEO
44 - The warning signs CEOs are scaling complexity instead of structure
The warning signs CEOs are scaling complexity instead of structure Scaling doesn’t fail because of ambition. It fails because of misalignment. Many founders…
- The Breakout CEO
43 - Advisory Insights: Finding and Fixing Executive Leadership Misalignment in a Scaling Business
In this episode, Jeff Holman sets the stage for a new Breakout CEO format: Advisory Insights, a short series of episodes where experienced operators and…
- The Breakout CEO
42 - Why Smart CEOs Design Their Exit Long Before They Sell
CEOs who want the option to sell their company later must run it with the operational discipline, customer traction, and leadership structure investors expect…
- The Breakout CEO
41 - Why Product-Market Fit Doesn’t Guarantee Funding
Product-market fit is supposed to unlock growth. But what happens when customers show up and investors don’t? In this episode, Meghan Higney — founder of the…
- The Breakout CEO
40 - The Moment CEOs Choose Between Growth and Standards
When growth pressures your standards, the decision defines your brand. Every scaling CEO eventually faces it: the deal that’s close but not quite aligned, the…
- The Breakout CEO
39 - Persevere or Pivot: The Founder’s Hardest Call
Every founder says perseverance is key. Fewer know when it becomes expensive. In this episode, John Cousins reflects on the hardest decision a CEO faces: when…
- The Breakout CEO
38 - When Authority Erodes, Pricing Power Disappears
Authority used to be assumed. Today, it must be built. As markets become more transparent and commoditized, pricing pressure doesn’t begin with competition —…
- The Breakout CEO
37 - The CEO Decision to Stop Competing and Redefine the Market
Most CEOs assume that winning means competing harder. Andrew Ackerman learned the opposite. When Dreamit Accelerator found itself stuck behind larger, more…
- The Breakout CEO
36 - Licensing or Operating: The CEO’s Inflection Point
Most founders prefer to license. It’s a lower risk. Lower capital exposure. Fewer operational headaches. But what happens when the incumbents won’t move, and…
- The Breakout CEO
35 - Choosing Legacy Over Lifestyle After a Billion-Dollar Exit
Small business credit isn’t broken because of a lack of data; it’s broken because the system was never designed for how businesses actually operate. In this…
- The Breakout CEO
34 - When CEOs Must Choose Between Conviction and Consensus
Markets don’t wait for consensus. In this episode, Shay Levi explains how CEOs recognize the moment when speed and conviction matter more than alignment and…
- The Breakout CEO
33 - The Decision That Separates CEOs Who Quit From Those Who Rebuild
Scaling doesn’t usually fail because of a bad product. It fails because focus erodes slowly, one customer, one feature, one exception at a time. In this…
- The Breakout CEO
32 - The Revenue Risk When CEOs Say “We Can’t Measure Event ROI"
In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Zach Barney, founder and CEO of Mobly, to talk about a problem many growth-stage…
- The Breakout CEO
31 - When a $4 Part Forces a CEO Into a Total Operating Reset
What does it actually take to scale a manufacturing business in the U.S. today? In this episode of The Breakout CEO, Jeff Holman sits down with Spencer…
- The Breakout CEO
30 - When CEOs Must Decide What AI Does and What It Never Should
AI can organize information faster than any team you’ve ever built. It can surface patterns, speed up workflows, and remove friction from execution. But it…
- The Breakout CEO
29 - What Happens When CEOs Tolerate Misalignment Too Long
Most leadership advice breaks down the moment real pressure shows up. In this episode of The Breakout CEO, Cydni Tetro, 3-time CEO, board member, and former…
- The Breakout CEO
28 - The Hidden Complexity Behind “Simple” Consumer Products
What does it take to build a company when the mission matters more than momentum? In this episode of The Breakout CEO, Jeff Holman sits down with Thomas…
- The Breakout CEO
27 - Replacing Hustle with EBITDA as the Real Scorecard
Every CEO reaches a threshold where hustle and revenue aren’t enough. In this episode of The Breakout CEO, host Jeff Holman cuts into the hard operating truths…
- The Breakout CEO
26 - The Real Truth About Selling a SaaS Business and Why Most Founders Get It Wrong
What does it really take to sell a SaaS business successfully? In this episode of The Breakout CEO, Jeff Holman sits down with Andrew Gazdecki, founder of…
- The Breakout CEO
25 - The Leadership Shift That Unlocks Breakout Growth (Most CEOs Learn It Too Late)
What does it really take to break through as a CEO when the pressure is highest, and the path forward isn’t clear? In this episode of The Breakout CEO Podcast…
- The Breakout CEO
24 - What It Takes for Women Founders to Build Companies Buyers Trust
What does it really take to move from founder control to strategic optionality? In this episode of The Breakout CEO podcast, Jeff Holman sits down with Heather…
- The Breakout CEO
23 - Why CEOs Need to Choose Calculated Risk Over Playing It Safe
Scaling a business does not usually break because of strategy. It breaks because the CEO is carrying too much. In this episode of The Breakout CEO podcast…
- The Breakout CEO
22 - Scaling Exposes This Leadership Weakness Every Founder Has
Scaling doesn’t fail because of strategy, capital, or product. It fails because of a leadership weakness almost every founder carries into growth. Impatience…
- The Breakout CEO
21 - The Leadership Blind Spots That Create Avoidable Problems
In this episode of The Breakout CEO podcast, Jeff Holman sits down with Leah Brown, former corporate lawyer turned mediator and founder of The WayFinders…
- The Breakout CEO
20 - When CEOs Stop Listening: Early Warning Signs Your Business Is Scaling the Wrong Way
In this episode of The Breakout CEO Podcast, I sit down with Steve Smith, a veteran business coach with more than 45 years of experience in manufacturing…
- The Breakout CEO
19 - The Unconscious CEO Habits That Are Holding Back Your Growth
In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Dr. Noah St. John, bestselling author of Power Habits and the creator behind the Zero…
- The Breakout CEO
18 - When Survival Turns into Strategy: The Breakout Shift Every CEO Needs
In this episode of the Breakout CEO podcast, host Jeff Holman interviews Jerry Brazie, an entrepreneur with a remarkable journey from poverty to success. Jerry…
- The Breakout CEO
17 - The Hidden Spiral Pattern Behind Fast-Growth Companies
In this episode of The Breakout CEO Podcast, host Jeff Holman sits down with Dr. Natasha Todorovic-Cowan, author of Making Change Work and expert in Spiral…
- The Breakout CEO
16 - The CEO Advantage No One Tracks: Understanding Your People Better Than Your Competitors Do
In this episode of The Breakout CEO Podcast, host Jeff Holman sits down with leadership coach and former competitive chess player John Whitt to explore the…
- The Breakout CEO
15 - Your Story Is Your Strategy: Why Most CEOs Miss It
In this episode of The Breakout CEO, Jeff Holman sits down with Paige Arnof-Fenn, a 24-year marketing veteran and CEO of Mavens & Moguls, to break down what…
- The Breakout CEO
14 - Preventing Burnout: The EQ Approach Every CEO Needs Now
In this episode of The Breakout CEO Podcast, host Jeff Holman sits down with Aasha LaCount, CEO of BeyondEQ International, to explore how emotional…
- The Breakout CEO
13 - Fractional COO Explained: The Role That Transforms Scaling Companies
This episode is part of our CEO Expert mini-series where we talk with experts who coach, mentor, train, and work with scaling CEOs to expand their insights and…
- The Breakout CEO
12 - From Bankruptcy to Industry Leader: The Mindset That Changed It All
In this episode of the Breakout CEO Podcast, host Jeff Holman speaks with Earl Foote, founder of Nexus IT, about the company's growth, team culture, and the…
- The Breakout CEO
11 - From the Navy to Medical Innovation: A Journey of Persistence and Purpose with Healionics Corporation's Mike Connolly
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO and Chairman at Healionics Corporation, Mike…
- The Breakout CEO
10 - Building with Heart: How Culture and Collaboration Drive Unlikely Success with Aspen Mountain Partners' Greg Schow
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the Partner at Aspen Mountain Partners, Greg Schow. Greg…
- The Breakout CEO
9 - How Curiosity Drives Innovation: Leadership Strategies for Growth with INSEAD's Spencer Harrison
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the Full Professor at INSEAD, Spencer Harrison. Spencer…
- The Breakout CEO
8 - The Importance of a Strong Foundation: Why Resilience Matters in Product Development with Product 1's Steven Selikoff
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the Founder of Product 1, Steven Selikoff. Steven shares…
- The Breakout CEO
7 - Resilience at the Crossroads: CEO Insights from Design and Logistics with Shyft's Alex Burdge
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO and Co-Founder at Shyft, Alex Burdge. Alex…
- The Breakout CEO
6 - Persistence in Action: Redefining the Fintech Landscape with ASA's Landon Glenn
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO and Founder at ASA, Landon Glenn. Landon shares…
- The Breakout CEO
5 - Pivoting in the Face of Adversity: Lessons from a Tech Leader’s Journey with Intel Corporation's Dr. Darren Pulsipher
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the Chief Solutions Architect at Intel Corporation, Dr…
- The Breakout CEO
4 - Smart Strategies for a Thriving Software Development Business with DevSquad's Phil Alves
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO at DevSquad, Phil Alves. Phil shares his journey…
- The Breakout CEO
3 - The Rollercoaster of Entrepreneurship: Embracing Ups and Downs for Growth with Startup Ignition Academy's John Richards
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the Founder and CEO at Startup Ignition Academy, John…
- The Breakout CEO
2 - Cash Flow and Innovation: Strategies for Sustainable Growth in High ASP Markets with SubcontractorHub's Justin Brach
In this episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Jeff Holman speaks to the CEO at SubcontractorHub, Justin Brach. Justin shares…
- The Breakout CEO
1 - From Crisis to Confidence: Unleashing the Breakout CEO Within with Jeff Holman
In the inaugural episode of The Breakout CEO: Inside the Strategic Moves of Scaling CEOs, Josh Elledge of UpMyInfluence speaks to Jeff Holman. Jeff is the…