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
106 - Hand Off Technology and Your Growth Stalls
What do you do as a CEO when the supplier behind most of your inventory disappears overnight? Rupesh Sanghavi, founder of Ergode, faced exactly that when…
- The Breakout CEO
105 - The $2M Never Came. The CEO Fired Everyone
What should a CEO do when the team and the offices are built for a $2M investment that never arrives? Asaf Darash faced that decision after spending about a…
- The Breakout CEO
104 - The Real Reason Scaling CEOs Keep Panic Hiring
Most CEOs get hiring wrong in one of two ways: they wait too long to bring someone on, or they panic and fill the seat with the wrong person the moment the…
- The Breakout CEO
103 - The Hidden Profits Framework: Why Resourcefulness Beats Resources for Scaling CEOs
Most businesses chase new clients while leaving real revenue sitting untouched inside the ones they already have. In this episode, business coach and…
- The Breakout CEO
102 - The One Question To Ask Before Any Brand Decision
Most brand and portfolio decisions inside scaling companies get made from the inside out — shaped by org charts, legal deadlines, and internal politics rather…
- The Breakout CEO
101 - What The Elevator Man Can Teach CEOs About AI Adoption
Most CEOs already agree AI belongs somewhere in their business — the harder problem is knowing where to start, and getting a team comfortable enough to…
- The Breakout CEO
100 - The Part of Your CEO Story You're Skipping
Many CEOs can tell you what happened: the market shifted, pricing changed, the quarter improved. What gets lost is what actually broke, how they recognized it…
- The Breakout CEO
99 - The Growth That Was Eating Your Best Product
When a services company and a product company try to grow under the same roof, one of them eventually has to lose. In this episode, Jared Shepard explains the…
- The Breakout CEO
98 - The Sales Trick That Nearly Ended a Founder's Career
Most CEOs never admit what they are bad at, and it costs them the exact hires and decisions that could help their business scale. Larry Gould built one of the…
- The Breakout CEO
97 - Why The Real Revenue Leak Is Rarely Where CEOs Look
Most scaling CEOs assume a revenue problem is a sales and marketing problem, and it costs them the real diagnosis. In this episode, Kati Peterman, founder of…
- The Breakout CEO
96 - The Framework Hiding Inside Every Founder's Head
Most companies eventually get commoditized, not because their product is weak, but because the thinking that made them different never gets written down…
- The Breakout CEO
95 - Why Financial Success And Self-Worth Are Not The Same Thing
Louis Swart built and sold multiple businesses — including one exit that scaled to $35 million in annual revenue — and still felt broken inside. In this…
- The Breakout CEO
94 - Why Presence Is the Multiplier That Determines How Far You Rise
Most CEOs assume they're judged on execution — results, competence, getting things done. Executive communication coach Mike Acker argues that's only half the…
- The Breakout CEO
93 - How a $30,000 Monthly Loss Forced a Founder to Rethink His Leadership
In 2015, a currency shock pushed the Canadian dollar from parity to $1.46 against the US dollar in eighteen months — a 46% jump in costs for Solpak, the…
- The Breakout CEO
92 - How OneMeta's Stalled Six-Figure Contract Grew into Eight-Figure Revenue
When one of OneMeta's first major enterprise contracts went quiet — right after signing, right after the prepaid revenue was recorded — nothing happened for…
- The Breakout CEO
91 - Why George Hartley Built Nitrosend Without a Dashboard
Most founders spend years perfecting a dashboard. George Hartley — who built and sold SmartrMail (acquired by Relay Commerce in 2022) and co-founded Bluethumb…
- The Breakout CEO
90 - The 90-day Reset Framework Advisors Use to Get Stalled Companies to Version 2.0
Most scaling companies don't fail because they stop trying — they fail because they keep doing more of what already isn't working. In this episode, Jeff Holman…
- The Breakout CEO
89 - The Three-Step Framework That Makes Hard Team Conversations Easier
Most founders don't have a hiring problem — they have a decision problem. Operations advisor Lia Garvin has spent years inside teams at Microsoft, Apple, and…
- The Breakout CEO
88 - Why Vision Beats Motivation When Scaling a Business
What separates CEOs who build resilient companies from those who burn out chasing the next motivational boost? In this episode of The Breakout CEO Podcast…
- The Breakout CEO
87 - The Strategic Altitude Every Scaling CEO Needs
As companies grow, the CEO's role must evolve. Yet many founders stay trapped in the day-to-day, becoming the very bottleneck that limits their company's…
- The Breakout CEO
86 - The Pivot This Founder Made After an Investor Called It Impossible
Every scaling e-commerce business eventually collides with the same silent problem: customers who don't get what they ordered, when they were promised it…
- The Breakout CEO
85 - The CEO Who Set Out to Change Policing Without Using More Force
What happens when someone reaches the top of the financial world—only to realize success isn't enough? In this episode of The Breakout CEO Podcast, Jeff Holman…
- The Breakout CEO
84 - The CEO Playbook for Building Trust Before You Build Demand
What separates companies that become market leaders from those that remain just another product? In this episode of The Breakout CEO Podcast, Jeff Holman sits…
- The Breakout CEO
83 - The Founder Lesson That Every CEO Should Hear About Customer Feedback
What if your biggest growth opportunity wasn't your product—but your customers? In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Julie…
- The Breakout CEO
82 - Why AI Won't Replace Great Real Estate Professionals
Artificial intelligence is transforming nearly every industry—but according to Sheldon Wolf, AI isn't here to replace real estate professionals. It's here to…
- The Breakout CEO
81 - Why Speed Beats Perfection in Healthcare Startups
What does it take to leave a successful corporate career and build a healthcare startup from scratch? In this episode of The Breakout CEO Podcast, Seth Merritt…
- The Breakout CEO
80 - The Signals CEOs Miss Before Growth Breaks Their Team
As companies scale, the first signs of trouble rarely appear on a dashboard. They show up in stretched teams, founder bottlenecks, and hiring decisions that…
- The Breakout CEO
79 - The Leadership Shift That Helped Build a Billion-Dollar Company
What separates CEOs who build enduring companies from those who simply manage growth? For Vikas Sehgal, the answer wasn't a better strategy or a more…
- The Breakout CEO
78 -Why Most Service Companies Sell the Wrong Thing
Most service companies lead with what they do. The ones that grow the fastest lead with the problems they solve. In this episode of The Breakout CEO Podcast…
- The Breakout CEO
77 - How Better Hiring Decisions Create Better Companies
Every CEO knows people matter. Fewer recognize that hiring is one of the highest-leverage strategic decisions they make. In this episode of The Breakout CEO…
- The Breakout CEO
76 -When Market Signals Are Strong Enough to Go All In
Most founders know how to build. Fewer know when the evidence is strong enough to commit. In this episode, Arthur Jessop shares how he moved from a successful…
- The Breakout CEO
75 - The Leadership Skill Most CEOs Undervalue: Human Connection
As companies scale, leaders often invest heavily in systems, processes, and technology while overlooking the one advantage that compounds across culture…
- The Breakout CEO
74 - The Inventory Signals Advisors Spot Before CEOs Do
Inventory problems rarely start as inventory problems. In this episode, Alex Hennick explains how excess inventory, warehouse pressure, and distressed assets…
- The Breakout CEO
73 - The Cash Flow Mistake Most Founders Don’t Realize They’re Making
Most founders think they have a growth problem when they actually have a cash flow problem. In this episode, Brandon Neely explains why many business owners…
- The Breakout CEO
72 - Why Investor Trust Matters More Than Your Pitch Deck
Most CEOs preparing to raise capital focus on pitch decks, projections, and presentation polish. George Dubec argues that investors are making decisions much…
- The Breakout CEO
71 - The Decision to Reinvest Instead of Cash Out
Many founders assume growth requires outside capital, debt, or aggressive expansion. Lindsey Prater took a different path. In this episode, Lindsey shares how…
- The Breakout CEO
70 - Why Most Startup Support Systems Fail Founders
Most startup advice focuses on founders. Gregory Shepard thinks that misses the real problem. After building and selling multiple companies, investing across…
- The Breakout CEO
69 - The Hardest Part of Scaling Is Rebuilding the Team
Scaling a company doesn’t usually fail because of strategy. It breaks when the organization can’t evolve fast enough to support the next stage of growth. In…
- The Breakout CEO
68 - Why Manufacturing CEOs Can’t Wait to Adopt AI Infrastructure
AI adoption is no longer a future planning exercise for manufacturers — it’s becoming an operational timing decision. In this episode, Torian Richardson…
- The Breakout CEO
67 - The Leadership Signals CEOs Miss About Themselves First
Most leadership blind spots do not show up as dramatic failures. They show up slowly — through exhaustion, drift, misplaced priorities, overextension, and…
- The Breakout CEO
66 - The Labor Cost Signal CEOs Start Tracking Too Late
Most CEOs don’t realize they have a labor cost problem until it’s already eroding margins. By the time the signal shows up clearly, it’s too late to fix…
- The Breakout CEO
65 - What Hidden Stress Reveals About a CEO’s Decision Quality
Most CEOs assume decision quality is a function of logic, experience, and information. This episode challenges that assumption. Rochelle Carrington explains…
- The Breakout CEO
64 - What CEOs Miss When They Think They’ve Already Scaled
Many CEOs believe they’ve scaled—until they step away and the business slows down. In this episode, Veronica Kirin breaks down why founder-led growth often…
- The Breakout CEO
63 - The Cost of Waiting Too Long on a High-Stakes Decision
What does it actually cost a CEO to wait for certainty? Yi-Kai Lo faced that question while leading Aneuvo through an $8M clinical trial, an 11-month FDA…
- The Breakout CEO
62 - What Happens When CEOs Delay AI Adoption in Engineering Teams
AI isn’t just accelerating software development — it’s exposing where your organization is already broken. In this episode, Ricardo Arcia shares what happened…
- The Breakout CEO
61 - The Moment CEOs Realize They’ve Become the Bottleneck
At some point in every scaling company, growth slows—not because of the market, the team, or the product—but because of the CEO. In this episode, Barry Bradham…
- The Breakout CEO
60 - What Happens When CEOs Optimize for Scale Over Trust
At some point in scaling, the model that drives growth starts to erode the very thing that made it work: trust. Amber Duncan built a highly profitable…
- The Breakout CEO
59 - What Happens When CEOs Ignore Cyber Risk in an AI-Driven World
Cybersecurity is no longer an IT issue—it’s a CEO-level decision with compounding consequences. As AI accelerates both innovation and attack capability, the…
- The Breakout CEO
58 - The Customer Concentration Risk CEOs See Too Late
Most CEOs know customer concentration is risky. Few experience what it actually feels like when it breaks. Jim Tracy shares the moment his only customer…
- The Breakout CEO
57 - The Hidden Cost of Building Blind in Product Development
Most product teams don’t fail because they build poorly — they fail because they build without knowing what will actually sell. In this episode, Pete Polyakov…
- The Breakout CEO
56 - How CEOs Build Companies by Solving Problems They Don’t Understand Yet
Most CEOs wait for clarity before committing. That’s often the mistake. In this episode, Dusty Gulleson breaks down what actually drives growth: saying yes to…
- The Breakout CEO
55 - Why Smart CEOs Still Make Bad Decisions Under Pressure
Most bad decisions aren’t caused by poor strategy or lack of intelligence — they happen because of the conditions surrounding the decision. As companies scale…
- The Breakout CEO
54 - The Three-Part Decision Framework CEOs Need to Cut Through Noise
Most CEOs don’t struggle with a lack of ideas — they struggle with too many. The real constraint is knowing which decisions actually matter, and which ones are…
- The Breakout CEO
53 - Diagnose Before You Scale: The CEO Discipline Most Skip
Many CEOs try to fix growth problems by adding more resources—more marketing, more hires, more tools. But according to advisor Jon Bassford, scaling problems…
- The Breakout CEO
52 - The Moment You Realize Your Product Isn’t the Business Model
A CEO must recognize when strong product traction masks a weak business model — and reframe the company around how value is actually monetized before growth…
- The Breakout CEO
51 - The Cost of Getting Comfortable Too Early as a Scaling CEO
Early success creates a false sense of security that hides structural weaknesses—and when disruption hits, only CEOs who take full accountability can rebuild…
- The Breakout CEO
50 - How Josh Carr Rebuilt Echo Water Into an $18M Hardware Company
As AI makes software easier to replicate, Josh Carr argues that durable businesses may increasingly come from harder-to-build physical products and hardware…
- The Breakout CEO
49 - The Cost of Scaling a Marketplace With Misaligned Incentives
Marketplace businesses look simple on the surface: connect supply and demand and let the network grow. But for CEOs, the real risk isn’t growth — it’s…
- The Breakout CEO
48 - The Leadership Shift That Took This CEO From Survival to Scale
What does it take to scale a company in one of the most competitive industries in technology? In this episode of the Breakout CEO Podcast, Jeff Holman sits…
- The Breakout CEO
47 - The Moment CEOs Realize Their Company Is Too Complicated
Most founders start with a simple idea. Then growth happens — and suddenly the company becomes ten different things at once. In this episode, PodMatch founder…