Jeff Holman

The Breakout CEO

Business EN ↓ 79 episodes

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 companie...

Author

Jeff Holman

Category

Business

Latest episode

Jul 9, 2026

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Episodes

079 - The Leadership Shift That Helped Build a Billion-Dollar Company 09.07.2026

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 billion-dollar global technology company, Vikas discovered that sustainable growth comes from shared value...

78 -Why Most Service Companies Sell the Wrong Thing 02.07.2026

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 conver...

77 - How Better Hiring Decisions Create Better Companies 30.06.2026

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 be...

76 -When Market Signals Are Strong Enough to Go All In 25.06.2026

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 23.06.2026

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 18.06.2026

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 17.06.2026

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 16.06.2026

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 found...

71 - The Decision to Reinvest Instead of Cash Out 11.06.2026

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 09.06.2026

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...

69 - The Hardest Part of Scaling Is Rebuilding the Team 04.06.2026

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 ownersh...

68 - Why Manufacturing CEOs Can’t Wait to Adopt AI Infrastructure 02.06.2026

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 r...

67 - The Leadership Signals CEOs Miss About Themselves First 28.05.2026

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 ex...

66 - The Labor Cost Signal CEOs Start Tracking Too Late 26.05.2026

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,...

65 - What Hidden Stress Reveals About a CEO’s Decision Quality 21.05.2026

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 — a...

64 - What CEOs Miss When They Think They’ve Already Scaled 19.05.2026

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 t...

63 - The Cost of Waiting Too Long on a High-Stakes Decision 14.05.2026

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...

62 - What Happens When CEOs Delay AI Adoption in Engineering Teams 12.05.2026

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 — an...

61 - The Moment CEOs Realize They’ve Become the Bottleneck 07.05.2026

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...

60 - What Happens When CEOs Optimize for Scale Over Trust 05.05.2026

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 30.04.2026

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 28.04.2026

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....

57 - The Hidden Cost of Building Blind in Product Development 23.04.2026

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 21.04.2026

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 unce...

55 - Why Smart CEOs Still Make Bad Decisions Under Pressure 16.04.2026

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...

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