The Breakout CEO

Jeff Holman, General Counsel for Scaling CEOs and Founders
  • 5.0 (5)
  • Entrepreneurship
  • Semiweekly

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 to choose a new one. Guests explain what they decided and what they would do differently. Recent topics include panic hiring, AI adoption, hidden revenue leaks, and building trust before building demand. Jeff Holman is the founder of Intellectual Strategies, where he works as outside general counsel to scaling CEOs and founders on strategy, governance, and risk during rapid growth. He brings that operator-level view to each interview. Be a guest: We feature a limited number of CEOs and founders with first-hand breakout stories. Apply at https://go.intellectualstrategies.com/ Media and event partnerships: For press access, on-site recording, or event collaboration, contact us through intellectualstrategies.com/podcast.

  1. 23h ago

    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 half.com shut down and took 80 to 90 percent of his inventory source with it. In this episode of The Breakout CEO, he walks through how each disruption, from a lost supplier to a ceiling on C2C margins, the COVID acquisition window, and tariff uncertainty, pushed his ecommerce company into its next business model. Rupesh started by buying a textbook on eBay and pre-selling it on Amazon, then wrote software to automate the buying while still working as an application engineer. He explains why he launched a second business to work directly with brands, how moving to brand ownership pushed margins past double digits, and the acquisition criteria that led him to walk away from deals that looked great on paper while others were reportedly paying 9 to 12 times EBITDA. He also gets candid about the two decisions he believes held the company’s growth back: closing his mind to outside investors, and the years he let someone else run technology, which he calls the least growth years. For founders weighing growth capital, team building, or how closely to stay involved in technology in the age of AI, this conversation shows what those choices can cost. Rupesh Sanghavi is the founder of Ergode, ergode.com. 00:00 Lessons From Scaling E-Commerce 01:59 From Engineering to Entrepreneurship 05:17 The $1,600 Textbook Sale 08:05 Building a Side Business 12:21 Creating a Brand Ecosystem 16:38 Losing Most Inventory Overnight 18:58 Acquiring Brands During COVID 22:41 Prioritizing Team and Technology 25:09 Becoming a Servant Leader 27:02 Choosing Will Over Skill 34:14 Evaluating Brand Acquisitions 47:51 Lessons That Limited Growth

  2. Oct 22

    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 year funding Regpack with his own money and loans while an angel investor’s committed $2M kept getting pushed back, until the investor went bankrupt. He had to choose between searching for new investors or bootstrapping, and he chose to cut the team from 12 or 13 people to 3 and spend a year working 14-hour days. Asaf explains why he believed the technology had to prove itself for 400 organizations, not just 4, before taking outside money. He also describes the revenue signal that told him the company would make it, and how staying founder-owned changed the financial outcome available to him. Along the way he shares how Regpack turned a marketing message that produced no leads into one that brought them in, why a free trial attracted exactly the clients the company didn’t want, and how a serious burnout led him to give his team full authority over their goals and budgets. 00:00 Firing Everyone to Survive 01:19 From Academia to RegPack 06:11 Learning Beyond Technical Expertise 10:02 Mastering Sales and Marketing 15:00 Building Infinite Product Flexibility 21:02 Why Feature Marketing Failed 25:11 Marketing in Four Seconds 30:14 Customers Want Clear Actions 35:00 Free Trials Attract Wrong Customers 40:49 Bootstrapping With Two Teammates 45:43 How AI Changed Technology 50:23 Burnout Forced Leadership Change Asaf Darash is the founder and CEO of Regpack, onboarding software for education and service-based organizations, at regpack.com.

  3. Oct 16

    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 pressure hits. Darren Tompkins, founder of Vader-Rey Companies, has spent years watching that pattern play out across the scaling businesses he works with in Houston's oil and gas, engineering, and construction market, and he has a simple diagnostic for when a CEO is overdue to delegate: watch your own personal time, not a revenue number. In this conversation, Darren breaks down why support functions like legal, IT, and back office operations quietly fall behind while a company chases new revenue, and why that gap is often what actually crushes a scaling business, not the sales slowdown everyone expects. He also explains why he treats recruiting less as a transaction and more as a strategic partnership built around a client's real long-term plan, and why most job descriptions fail to attract the right talent because they were never written for the specific person a CEO actually needs. 00:00 Avoid Hiring Too Late 01:18 Three Companies, One Talent Mission 04:13 The First Executive Decision 08:18 Recruiting as Strategic Partnership 11:22 Set a Date and Leave 20:00 The Virtual Workforce Advantage 24:31 Common CEO Hiring Mistakes 28:13 Why Support Teams Fall Behind 34:05 Where Process Meets Creativity 37:24 Beyond Generic Job Descriptions 41:06 The New Employee Marketplace 42:45 Getting Time and Peace Back Darren Tompkins is the founder and CEO of Vader-Rey Companies, which provides recruiting, project staffing, and virtual professional support to scaling CEOs and owners.

  4. Oct 15

    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 consultant Stacey Hylen — who mentored under Chet Holmes and later served as VP of Consulting for Tony Robbins' Business Mastery brand — breaks down her Hidden Profits framework: a way to grow revenue through upsells, client reactivation, and deeper account mining, without spending another dollar on marketing. Stacey also explains why the real constraint most CEOs face isn't a lack of resources, but a lack of resourcefulness — and why that reframe changes what to focus on first. Stacey Hylen works with seven- and eight-figure B2B founders who are excellent at their core business but haven't built repeatable marketing and sales systems around it. Her Hidden Profits methodology, born out of a moment she witnessed live at a Tony Robbins event during the 2008 recession, centers on a simple but often-overlooked question: what revenue is already available inside your existing clients and products? In this conversation, she walks through how that question has driven results ranging from a 48% sales increase at a family-owned auto parts store to multi-million-dollar account growth built entirely from mining relationships that were already in place. TRANSCRIPT SUMMARY:00:00 Resourcefulness Unlocks Hidden Profits 01:24 Learning From Chet and Tony 04:13 When Successful CEOs Need Coaching 06:12 Coaching Should Remove Work 09:20 Scaling Sales Beyond the Founder 11:13 The Cost of Endless Hustle 15:20 Creating Boundaries for Family 18:20 Finding Hidden Profits 21:32 One Upsell Grows Sales 48% 25:06 The $700,000 Reactivation Mistake 30:40 Mining Your Existing Clients 33:14 Working in Your Genius Zone

  5. Oct 14

    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 decision gets finalized: where are the insights? Drawing on real client situations — from a four-day deadline to name a newly acquired company to untangling a four-brand portfolio boxed in by its own building — Kevin walks through what changes when customer insight, not internal convenience, drives the decision. Episode Description Kevin Perlmutter has spent more than three decades in advertising and branding, including 16 years at ad agencies and seven years at one of the world's largest brand consultancies, before founding Limbic Brand Evolution in 2019. His approach is rooted in behavioral science: the idea that customers choose and stay loyal to brands for emotional reasons, not because of features or internal talking points. In this conversation, Kevin explains the diagnostic pattern he sees repeatedly across CEO engagements — brand and naming decisions made from internal logic instead of customer insight — and the framework he uses to correct course, including how he handles pressure-filled moments like acquisitions and portfolio restructuring. TRANSCRIPT SUMMARY:00:00 Building Brands From Customer Insight 01:14 Behavioral Science Meets Brand Strategy 04:15 Why Internal Messaging Falls Short 07:28 Emotions Drive Customer Decisions 09:33 Why Brand Names Need Strategy 13:19 What a Brand Truly Is 15:46 When CEOs Need Brand Help 18:06 Navigating Brands After Acquisitions 20:14 Simplify the Customer Experience 22:30 Why Customers Choose Easy Paths 25:37 Turning Insights Into Brand Desire 29:12 Always Ask Where Insights Are

  6. Oct 13

    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 begin. In this conversation, Bryant explains why AI needs an active human guide rather than passive reliance, why most companies are missing even a basic usage policy, and why the psychological work of getting a team "into the elevator" often matters more than the technology itself. Bryant Oberg spent 15 years in finance — banking, then the buy side, eventually becoming a partner at a hedge fund — before building his first AI-powered business in six weeks with no technical background. That business was wiped out overnight by a regulatory change, a setback that pushed him to pivot fully into AI advisory work through Human Co-Pilot. His perspective is built on a recurring pattern he sees across CEOs and their teams: agreement that AI matters, paired with uncertainty about how to actually implement it. He walks through the concept of "shadow AI" — employees using personal AI tools with company data because no policy exists — and offers a framework for closing that gap through governance and hands-on adoption support. TRANSCRIPT SUMMARY00:00 Humans Must Lead AI 01:02 From Finance to AI Entrepreneurship 02:46 Escaping AI Productivity Pressure 07:14 A Failed Business Sparks Reinvention 12:22 Understanding Nondeterministic AI Responses 14:27 Allow AI to Admit Uncertainty 17:18 Keeping Humans in Control 20:53 Shadow AI Creates Business Risk 23:20 The Elevator Operator Analogy 24:45 Start With Policy and Education 28:01 The Fractional Chief AI Officer 31:36 Too Busy to Implement AI

  7. Oct 12

    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 arc moves from Build, the business and the leader’s background, to Break, what disrupted momentum and how you recognized the signal. It continues to Breakout, the reflection, insights, constraints, decision and action behind the scenes. It ends at Breakthrough, the new trajectory for the business and for you as a leader. Jeff explains why each stage matters when you tell your story to your team, investors or peers, including feedback that pushed him to dig deeper into the build stage in his own interviews. He points to two past episodes per stage: 34 and 85 for build, 33 and 79 for break, 48 and 99 for breakout, and 42 and 77 for breakthrough. He also shares where the show is headed as it grows into a community for scaling CEOs, with an online community, events and the Breakout CEO Awards planned for 2027, details to come. Jeff Holman is the host of The Breakout CEO. 00:00 Episode 100 and the Start of Season Five 00:29 62 CEO Conversations Reveal the Breakout Arc 02:03 Why CEOs Tell Better Stories With a Framework 03:31 Show Recap: CEO Episodes, Advisory Insights, Global Guests 07:18 From Podcast to a Community of Scaling CEOs 08:40 The Breakout CEO Awards and Why CEOs Deserve Recognition 10:16 A Missing Stage Means a Missing Piece of Your Story 11:26 Stage One, Build: Business and Leader Context 13:31 Stage Two, Break: Name It and How You Recognized It 15:36 Stage Three, Breakout: Reflection, Constraints, Decision, Action 19:09 Stage Four, Breakthrough: New Trajectory for Business and Leader 21:33 Eight Past Episodes That Illustrate Each Stage Episodes Mentioned: Ep. 037, Andrew Ackerman (Second Century Ventures): The CEO Decision to Stop Competing and Redefine the MarketEp. 058, Jim Tracy (Legacy Enterprises): The Customer Concentration Risk CEOs See Too LateEp. 062, Ricardo Arcia (Teravision Technologies): What Happens When CEOs Delay AI Adoption in Engineering Teams Subscribe to The Breakout CEO newsletter: https://podcast.intellectualstrategies.com/

  8. Oct 1

    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 communications tool built for a narrow military use case was actually a massive BYOD opportunity for banks, healthcare systems, and eventually consumers, and the tradeoffs that came with chasing that bigger market, including giving up control, taking on a board, and learning to sell against competitors with no comparable category. Jared talks candidly about what it took to reposition Hypori's pitch as it scaled from a few hundred thousand dollars in revenue to roughly 35 million dollars today, including the moment investors told him security was table stakes and the real value was in data sovereignty. He also gets into what it means to lead when every adjacent platform, from phone manufacturers to Microsoft, sees your growth as a threat to their own business model. For CEOs weighing whether to spin a product out of an existing operation, or trying to reposition a company that has outgrown its original pitch, this conversation offers a clear look at the decision points, cost of delay, and leadership shifts involved. Jared Shepard is the founder and CEO of Hypori, and also leads Intelligent Waves and the veteran-focused nonprofit Warriors Ethos. Learn more at hypori.com. 00:00 Jared Shepard’s Unconventional CEO Journey 01:22 From Homelessness to Military Service 06:49 Building Intelligent Waves in Iraq 11:19 Redefining the Ultimate Sacrifice 15:08 Creating Warriors Ethos 20:19 The Mission Behind Hypori 24:27 Products and Services Cannot Coexist 27:34 Swimming With Silicon Valley Sharks 32:05 Disrupting Secure Mobile Computing 38:25 Why No-Brainers Become Hard 45:13 Hire Diamonds, Not Shiny Rocks 50:12 Learn From Everyone Around You

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5
out of 5
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About

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 to choose a new one. Guests explain what they decided and what they would do differently. Recent topics include panic hiring, AI adoption, hidden revenue leaks, and building trust before building demand. Jeff Holman is the founder of Intellectual Strategies, where he works as outside general counsel to scaling CEOs and founders on strategy, governance, and risk during rapid growth. He brings that operator-level view to each interview. Be a guest: We feature a limited number of CEOs and founders with first-hand breakout stories. Apply at https://go.intellectualstrategies.com/ Media and event partnerships: For press access, on-site recording, or event collaboration, contact us through intellectualstrategies.com/podcast.

Information

  • Creator
    Jeff Holman, General Counsel for Scaling CEOs and Founders
  • Years Active
    2025 - 2026
  • Episodes
    106
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Intellectual Strategies
  • Show Website
    The Breakout CEO