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The Breakout CEO

The Breakout CEO

Jeff Holman 71 Episodes Jul 2, 2026

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

78 -Why Most Service Companies Sell the Wrong Thing Jul 2, 2026 49:51 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 Jun 30, 2026 58:44 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 Jun 25, 2026 52:09 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 Jun 23, 2026 01:05:25 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 Jun 18, 2026 37:59 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 Jun 17, 2026 38:13 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 Jun 16, 2026 26:41 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 Jun 11, 2026 41:26 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 Jun 9, 2026 47:10 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 Jun 4, 2026 55:42 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 Jun 2, 2026 54:55 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 May 28, 2026 57:17 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

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