The Breakout CEO
The Breakout CEO podcast features candid conversations with CEOs of scaling companies at leadership and strategic inflection points. Host Jeff Holman, founder of Intellectual Strategies, interviews leaders about the mindset, strategy, and decisions driving breakthrough success for high-growth firms. Each episode focuses on real decisions and pivotal moments rather than retrospective storytelling.
Episodes
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 than what customers actually experience. Behavioral-science brand strategist Kevin Perlmutter, founder of Limbic Brand Evolution, argues that the fix isn't a bigger rebrand — it's a standing question leaders ask before any brand or portfolio
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 actually use it. Bryant Oberg, founder of Human Co-Pilot, argues that most AI struggles aren't AI problems at all. They're human governance and adoption problems, and they show up as "shadow AI," stalled initiatives, and teams too overwhelmed to be
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, and what they were thinking when they made the decision. For episode 100 of The Breakout CEO, host Jeff Holman goes solo to share the Breakout Arc, a four-stage framework he identified after conversations with 62 CEOs across 99 episodes.The
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 decision that forced him to spin Hypori out of his 20 year old, bootstrapped services company, Intelligent Waves, and raise venture capital for the first time in his career as a founder. He walks through the moment he realized a secure commu
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 world's largest language companies, The Big Word, and years earlier built and sold a recruitment business, but neither started with a plan. Both trace back to moments most founders would rather bury: a childhood spent selling comics door to
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 fractional executive firm YourFRX, breaks down why so many operations issues get misread as leadership or marketing failures, and what actually happens when a CEO gets too far removed from their own numbers.Kati walks through her five fiv
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 anywhere but the founder's head. As a company scales and adds layers of salespeople, that original thinking dilutes into generic spec language, and CEOs find themselves competing on price against rivals who look just like them. Simon Bowen, founde
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 conversation, he unpacks the diagnostic framework he now uses with CEOs: why success and self-worth are separate variables, why the beliefs driving self-sabotage almost always trace back to childhood, and why no one can diagnose their own blind sp
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 equation. Presence, he explains, doesn't just support execution; it multiplies it, and the gap between the two can quietly cap how far a leader rises, or open doors execution alone never could.In this conversation, Mike traces that idea throu
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 packaging distribution company David Salerno had spent years building. At the worst point, the company was net-losing $30,000 a month, with hundreds of thousands in outstanding payables piling up at the same time.David Salerno, founder of Solpak P
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 six months. Saul Leal, CEO of OneMeta, walks through why the deal stalled, how his team learned to diagnose the real cause instead of assuming failure, and what changed when a board member reframed the entire situation. This episode follows th
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, Australia's largest online art marketplace — is betting his third company on removing it entirely. Nitrosend runs from inside Claude, Cursor, or ChatGPT, with AI agents doing the majority of the work.In this episode, George walks through th
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 talks with Diane Moura, Founder & CEO of ZenChange Marketing, about what actually separates companies that break through a growth ceiling from those that stay stuck. Diane has spent decades working with Fortune 500 companies and now adv
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 Google, and now works directly with founders running businesses of three to fifty people, diagnosing why so many of them can't step back from the day-to-day. In this episode, she breaks down why founders keep absorbing decisions their team co
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, Jeff Holman sits down with entrepreneur, speaker, and leadership strategist Rael Bricker to explore why lasting business growth starts with vision—not motivation. Drawing from decades of experience leading businesses across engineering, educatio
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 growth.In this Advisor Insights episode, Jeff Holman sits down with Logan McKnight, Founder and Principal Consultant at GoodKnight Consulting, to explore what it takes for leaders to gain "strategic altitude." Drawing on his experience as both a
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. Jevon Le Roux, CEO and co-founder of Keeyu, lived that problem firsthand before building a company to solve it — and along the way, a well-known investor told him it couldn't be done.In this episode, Jevon breaks down why customer service has be
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 sits down with Scot Cohen, CEO of WRAP, to explore the deeply personal journey that led him from a successful career in finance to building a company focused on reducing harm in public safety. Scot shares why he walked away from Wall Street
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 down with Romney Williams, entrepreneur, inventor, and CEO of DRYOUT, to explore the leadership decisions behind building a category-defining business.Drawing from decades of experience launching companies, protecting intellectual property, a
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 Tylman, Co-Founder and Co-CEO of Group Together, to discuss how relentless customer listening shaped every major decision in her company's journey.Julie shares how a simple idea to simplify group gifts evolved into an international business, w
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 empower the ones who embrace it.Drawing on more than 35 years of experience in real estate investing, development, brokerage, and PropTech, Sheldon explains why the future belongs to leaders who understand customer behavior, not just technolo
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 shares how a side project became Welby Health, a fast-growing healthcare technology company transforming chronic care management.Seth explains why moving quickly—not perfectly—became his competitive advantage, how customer conversations shap
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 lag behind growth.In this episode of The Breakout CEO Podcast, David Khim, Co-Founder of Omniscient Digital, explains why CEOs need to pay attention to qualitative signals before traditional metrics catch up. Drawing from his own experience sc
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 aggressive sales process. It was a fundamental shift in how he viewed leadership. After helping build Nagarro from a living room startup into a global technology company, Vikas discovered that sustainable growth comes from shared values, empowering gr
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, Mike LaVista, Founder & CEO of Caxy Interactive, explains how one shift in positioning transformed his consulting business from transactional projects into strategic partnerships, dramatically increasing deal size and changing the conversa
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 Podcast, Fletcher Wimbush shares why building a better company starts with building a better hiring system. From hiring for integrity over raw talent to eliminating "talented terrors" and staying relentlessly focused, Fletcher explains how bet
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 corporate career into entrepreneurship after recognizing a series of market signals that convinced him Base Case was more than just an interesting product idea. From CES validation and crowdfunding success to customer feedback and ICP refine
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, retention, sales, and customer experience: human connection. In this conversation, Richard Blank shares lessons from building Costa Rica's Call Center from the ground up, why communication remains a competitive advantage in an AI-driven world, an
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 often reveal deeper operational and financial issues long before most CEOs fully recognize them. Drawing from nearly two decades in liquidation and excess inventory markets, Alex shares the patterns he sees repeatedly across scaling businesse
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 misunderstand liquidity, leverage, and access to capital — and how those blind spots create unnecessary financial pressure during periods of growth or crisis. Rather than focusing only on revenue, Brandon argues founders need to understand how
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 earlier — based on founder credibility, clarity, visibility, and whether they believe the CEO can actually execute.In this episode, George explains why investor trust increasingly outweighs traditional fundraising materials, how modern founde
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 she and her sister grew Groovy Peach from an 85-square-foot salon suite into a multi-location, multi-million-dollar business by repeatedly choosing to reinvest earnings instead of extracting them. The conversation explores what happens when
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 startup ecosystem, and spending years researching startup failure, Gregory came to a different conclusion: founders are often operating inside fragmented systems that were never designed to scale.In this episode, Gregory breaks down why st
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 this episode, Drew Allen shares the realities of rebuilding a leadership team while transforming a business — including failed product launches, painful personnel decisions, engineering bottlenecks, and the challenge of creating a true ownershi
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 explains why the speed of technological change is now outpacing traditional organizational decision-making and what that means for manufacturing leaders trying to stay competitive.From digital twins and operational data visibility to leadership re
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 decisions that stop feeling intentional.In this episode, Jane Monroe shares how building and scaling her business forced her to confront leadership patterns she did not fully recognize in herself until pressure exposed them. The conversation exp
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 without pain.Albert Bou Fadel breaks down why labor costs are one of the most misunderstood—and least controlled—drivers of profitability, and how weak data, loose systems, and human incentives combine to create invisible risk.Albert Bou Fadel, Fo
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 why hidden internal stress — not strategy — is often the real constraint on decision speed, clarity, and execution.If decisions are slowing down, hiring is delayed, or growth is stalling, the issue may not be external. It may be internal — and
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 creates hidden bottlenecks, especially in sales and decision-making. She explains what real scalability actually requires—and why most CEOs don’t recognize the gap until it’s already limiting growth.If your business still depends on you more tha
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 process, and a product failure mid-study. In each case, the decision wasn’t just about risk — it was about whether delay itself had become the bigger risk.“After analyzing the risk and benefit… the cost of keep delaying the study”Yi-Kai Lo, CEO of
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 when his company started losing deals in 2024 — not because they lacked talent, but because their approach to building software had already become obsolete.This is a conversation about what actually changes when AI enters your workflow — and
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 breaks down what that moment actually looks like in practice—and what it takes to move past it. From building systems that remove dependency on the founder to leveraging AI and automation, this conversation is about the shift from operator t
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, fast-growing business—only to realize that the way it scaled was disconnecting her from the people she was trying to help. This episode explores what happens when financial success masks a deeper breakdown in customer connection—and the decision to
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 cost of delaying action is rising faster than most leaders realize.In this episode, Brian Cute, CEO of Global Cyber Alliance, breaks down what’s changing in the cyber threat landscape—and why many companies are already behind. From AI-powered
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 canceled every purchase order—and what it forced him to confront about leadership, responsibility, and survival. This episode is about what happens when a hidden risk becomes immediate reality—and how CEOs respond when there’s no time to prepare.J
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 breaks down the hidden cost of building blind — where manufacturers spend tens or hundreds of thousands per product without real demand signals. The result isn’t just wasted capital — it’s a system where failure is baked into the business mo
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 opportunities before you fully understand them — and building the capability to solve them after.From landing Google as a client without a plan to scaling a multi-division company, this conversation is about how real CEOs operate under uncert
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, pressure compounds: speed increases, stakes rise, and leaders operate under stress, fatigue, and incomplete signals. In those environments, even strong CEOs make preventable mistakes.In this episode, William Holsten breaks down the hidden fa
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 just noise.In this episode, Christiane Schroeder introduces a three-part decision framework to help CEOs cut through complexity, move faster, and lead with clarity — without getting stuck waiting for alignment or delaying action under uncer
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 rarely come from a lack of effort or investment. They come from failing to diagnose what’s actually broken inside the organization.In this episode, Bassford explains why CEOs must diagnose operational and cultural breakdowns before trying to
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 compounds the wrong path. The episode centers on a critical reframing moment: realizing that product success (downloads, usage) does not equal a viable business model. The conversation develops through tension between B2C traction and B2B mo
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 stronger. This episode follows the arc of growth → comfort → blind spots → external shock → internal reckoning → rebuild, showing how success itself becomes the precursor to failure. The conversation sharpens around a single decision: blame
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 companies. Echo Water effectively restarted from scratch, forcing the company to rebuild customers, products, and operations from the ground up. Josh Carr explains why hardware companies are harder to build but often more defensible than softw
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 misalignment between stakeholders.In this episode, Paul Roberts, CEO of GoodBite, explains why marketplace startups often fail when incentives between customers, partners, and suppliers drift apart — and why scaling too early can make the problem ex
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 down with Michael Chaput, CEO of Endsight, to explore the leadership transformation that helped him grow a managed services company to more than $35 million in revenue and 140 employees. Michael shares the lessons he learned after his first comp
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 Alex Sanfilippo shares the moment he realized his business had become confusing to the market. After launching multiple offerings and expanding quickly, he discovered that customers no longer understood what the company actually did.For CEOs
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 Insight episode, Robert White breaks down the hidden cost of leadership misalignment — and why it almost always traces back to a failure to clearly define and enforce purpose, vision, and values.Episode DescriptionExecutive misalignment rarely a
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 episode, Ral West breaks down the recurring pattern she sees: founders who want scale but continue operating as if the business would “die without me.” That tension — between control and trust — is where companies either plateau or accelerate.Episode
44 - The warning signs CEOs are scaling complexity instead of structure
The warning signs CEOs are scaling complexity instead of structureScaling doesn’t fail because of ambition. It fails because of misalignment.Many founders believe they’re building for growth — launching new services, expanding markets, hiring faster. But without structure underneath that growth, complexity compounds. What feels like momentum becomes chaos. What looks like opportunity becomes bottl
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 advisors share the patterns they see inside scaling companies.The theme for this series is executive leadership misalignment — a problem that rarely shows up as a dramatic conflict, but instead builds slowly through small signals inside the busine
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 long before an exit process begins.Many CEOs delay thinking about exit readiness because it feels premature or distracting from growth.The hidden risk is that companies built around founder effort, weak metrics, or informal operations become
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 footwear brand Message — shares what it looks like when early traction collides with a funding drought. After launching to strong demand and immediate media attention, Meghan discovered that validation from customers didn’t translate into capi
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 client outside your ideal profile, the opportunity that promises revenue—but threatens your operating discipline.Chris Shurian built multiple companies across construction and hospitality by choosing standards over opportunistic growth. He le
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 to push through obstacles — and when to admit the wall in front of you is brick. Drawing from his experience launching and losing control of a startup, John breaks down the tension between conviction and reality, control and collaboration, pe
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 — it begins with perception. When differentiation disappears, the only lever left is price.In this episode, Dennis “DM” Meador explains why founder-led visibility is no longer optional — and how CEOs who fail to build authority early eventually
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 established competitors, the question wasn’t how to move from number three to number one. It was whether that race was worth running at all.This episode explores the pivotal decision to stop fighting for position in a crowded market — and instea
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 your product only works if someone actually operates it?In this episode, Jeff Doss shares the pivotal decision to stop trying to license his patented anchoring system and instead operate the business himself inside a small, skeptical, highly re
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 episode, host Jeff Holman speaks with Sal Rehmetullah, CEO and Founder of Worth AI. He has scaled, exited, and re-entered fintech at the highest levels. After building Stax Payments into a market leader and navigating a billion-dollar recapita
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 what it costs to hesitate. Drawing from building and exiting Noname Security and starting Unframe, Shay breaks down how he made contrarian calls under uncertainty, trusted firsthand signals over investor pushback, and moved aggressively when
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 episode, Keith Norris shares the decisions that nearly broke his company and the hard reset that followed. From serving too many customers across too many industries to running multiple products that were effectively separate businesses, this is a
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 companies quietly accept.They spend a lot on in-person events and have no real way to know what is working.Zach explains how his background as a VP of Sales exposed a gap most teams accept as normal. Digital marketing is measured closely. In-perso
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 Loveless, second-generation CEO of Dustless Technologies and founder of Merit3D @Merit-3D .Spencer grew up inside a family-run manufacturing business and stepped into leadership early. Over time, he’s had to navigate the realities most CEOs don’t
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 still can’t make judgment calls when the data is incomplete, the market is shifting, and real money is on the line. In this episode of The Breakout CEO, Jeff Holman talks with entrepreneur and financial advisor Luigi “Lou” Rosabianca about wher
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 CIO of Swire Coca-Cola, draws from her experience as a 3-time CEO, enterprise executive, and board member to talk through those moments honestly. Not as lessons learned in hindsight, but as decisions made while the outcome was still unclear. C
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 Bishop, founder of Paleblue, for a grounded conversation on conviction, persistence, and building products that genuinely change behavior. Tom shares how a near-death experience reshaped his career decisions and why meaningful missions became the
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 that separate early growth from a sustainable scale. We explore what happens when pricing, financial clarity, team leadership, and systems become the deciding factors—not just harder work or bigger marketing.This conversation goes deep on th
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 Acquire.com (formerly MicroAcquire) to unpack what founders need to know about buying, scaling, and exiting online businesses.Andrew has helped thousands of founders sell SaaS companies, ecommerce brands, mobile apps, and digital businesses. In t
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, I sit down with Nikky Kho @NikkyKho , an entrepreneur, AI pioneer, and lifelong learner for a wide-ranging conversation on the breakout moments that shape leaders at the highest levels. Nikky’s journey is anything but conventional. Over a
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 Griffith Barber, founder of Queen of Wraps, to unpack the real decisions behind building a company that buyers take seriously. Heather shares her 18-year journey growing a business from a scrappy family operation into a multi-company platfo
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, host Jeff Holman sits down with Corinne Morahan, founder and CEO of Grid + Glam, to talk about burnout, boundaries, and the leadership shift that changed how she built her business. Corinne shares her journey from Wall Street to entrepreneurs
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