The Breakout CEO

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

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 companies, helping leaders navigate moments when complexity increases, tradeoffs become unavoidable, and the cost of misalignment rises. He brings a peer-level perspective shaped by that experience, focusing conversations on the inflection points that materially change a company’s trajectory. The Breakout CEO podcast reflects his approach with candid, operator-level discussions centered on real decisions rather than retrospective storytelling or promotion. Guest Participation - We feature a limited number of CEOs leading scaling companies with meaningful, first-hand breakout moments. If you believe your story would add value for an audience of scaling CEOs, please apply here: https://go.intellectualstrategies.com/ Media & Event Partnerships - For press access, on-site recording, or event collaboration inquiries, please contact us. We record a limited number of on-site conversations at select events with CEOs and founders whose stories align with the podcast’s focus on leadership, strategy, and execution.

  1. 19h ago

    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

  2. 1d ago

    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

  3. 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

  4. Sep 24

    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 door for ice cream money, a misdiagnosed medical condition that pushed him out of school at fifteen, and a sales job crisis where a suspiciously low expense report nearly got him fired for dishonesty. Instead of losing his job, Larry was reassigned into international sales, where a lack of budget for support staff forced a decision, insisting on translated materials and direct communication with clients in their own language, that eventually became the foundation of his translation business. In this episode, Larry walks through the operating philosophy he still uses today: knowing exactly what he is not good at, whether that is finance or technology, and building his team and his leadership decisions around people who are clever where he isn't, then letting them go once they stop being the sharpest option as the business grows. He also unpacks the framework behind his obsession with the word irresistible, a discipline he pushes on every client, employee, and investor conversation, and why most CEOs cannot answer a simple question about what makes their own company worth choosing over the competition. Larry Gould is a serial entrepreneur, founder of The Big Word, and a mentor to founders at Cornell Tech. (Guest website not confirmed in transcript — recommend confirming with Larry's team before publishing.)

  5. Sep 18

    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 five four framework for diagnosing where a growing company is breaking down, from meeting structures to KPI tracking, and shares a case where a founder was blaming their CMO for a revenue shortfall that turned out to be sitting untouched in an unmanaged accounts receivable process worth millions of dollars. The conversation covers when a fractional leader makes more sense than a full-time hire, why CEOs often make the mistake of hiring another version of themselves instead of the operator they actually need, and how staying curious about the numbers, even when things look fine, prevents small gaps from becoming expensive ones. Kati Peterman is the founder of YourFRX, a fractional executive team helping scaling businesses close operational gaps across leadership, finance, and operations. Learn more at yourfrx.com.

  6. Sep 17

    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, founder of Models Method, joins the show to unpack the diagnostic lens he uses with CEOs and organizations of every size, from Fortune 500 companies to smaller scaling businesses, to surface what he calls a company's genius, the specific way it thinks about a customer's problem. Simon walks through how he uses simple visual models, built from nothing more than a square, a circle, a triangle, and a line, to defuse conflict in high stakes meetings, align leadership teams around a single level of strategic thinking, and extract a founder's original insight before growth buries it. He also explains why simplification, not why messaging, is what actually earns trust in the marketplace, and why he believes how a company thinks, not why it exists, is what gets it chosen over the competition. For CEOs wrestling with a team that can no longer articulate what makes the company different, or a sales process that has quietly slid into price matching, this conversation offers a concrete framework for putting that thinking back on the table, literally. Simon Bowen is the founder of Models Method. Learn more at modelsmethod.com. 00:00 The Cost of Diluted Thinking 01:27 Business as a Positive Force 05:59 Service Beyond Shareholder Value 08:42 The Hidden Weight of Leadership 12:08 Leading Through Difficult Redundancies 18:57 Simplification Requires Sophisticated Thinking 24:04 Build Agreement Before Solutions 35:27 Models Remove Communication Ego 42:12 Aligning Strategic Thinking Levels 54:27 Capturing Your Company Genius 1:00:55 Why Gets Heard, How Wins 1:09:32 Company Genius as Source Code ‍

  7. Sep 16

    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 spots from inside their own perspective. This episode is for any CEO who has hit the same wall more than once and suspected the problem wasn't external. Louis Swart spent years building and exiting businesses before recognizing a pattern: financial success kept arriving, but a sense of being fundamentally "not enough" never left. That recognition led him to train directly in the methods used to diagnose it — NLP, hypnotherapy, and timeline therapy — while still running his own company. In this conversation, Louis lays out the framework that came out of that work: the three primal needs (love, safety, and worthiness) that quietly drive overwork and resistance to delegation, and the "gestalt" mechanism by which a single childhood belief compounds across school, sport, and business until it feels like an unchangeable fact rather than an old story. The conversation moves from diagnosis to method — how a coach identifies these beliefs in a CEO who cannot see them in himself, and what changes once the belief is traced back to its origin. 00:00 Breaking CEO Limiting Beliefs 02:32 From Bottleneck to $5M Exit 05:39 When Success Still Feels Empty 08:08 Befriending Your Inner Imposter 13:07 The Hidden Fear of Success 20:05 Busy Means Love, Safety, Worth 25:43 You Cannot Outwork Beliefs 32:19 Seeing Beyond Your Own Patterns 45:24 How Childhood Beliefs Shape Business 50:05 Building Genuine Internal Validation 54:56 Delegating Without Fear or Insecurity 58:52 Do the Inner Work Now‍ Key Takeaways Success and self-worth are two different variables — and one does not guarantee the other. A CEO can be objectively, measurably successful and still carry an unresolved belief that they are not worthy of it.Beliefs formed early — often before age ten — quietly control decisions made decades later. A belief like "I have to give people things or they won't love me" can drive a leader's overwork and resistance to delegation without ever being named.You cannot diagnose your own limiting beliefs from inside your own perspective. The same reason an elite athlete needs a swing coach applies to CEOs — the pattern is invisible from the inside.Beliefs compound like a pearl necklace — pull one loose, and the whole chain can fall apart. Once the original belief is shown to be untrue, the reinforcing "evidence" collected across a lifetime loses its grip.The three primal needs — love, safety, and worthiness — are usually the real Guest: Louis Swart Guest website: https://louisswart.com/ Guest LinkedIn: https://au.linkedin.com/in/coachlouisswart

  8. Sep 15

    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 through his own path from a childhood speech impediment to executive director at 26, and into the pattern he now sees across the CEOs and founders he coaches: high performers who can run a company but not a room, and what actually closes that gap. Mike Acker built his career on the opposite end of the spectrum from where he now coaches from. A speech impediment as a child, then years of being mocked after a move to Mexico, gave way — almost by accident, through a college debate team — to a communication skill set that later got him hired into a Fortune 500 company despite having no relevant experience or education. That firsthand experience of presence outweighing credentials became the foundation for the framework he now uses with CEOs and executives. As an advisor working across corporate training engagements (General Electric, among others) and one-on-one executive coaching, Mike's insight isn't a single client story — it's a pattern he sees repeatedly: leaders whose execution is strong but whose fear of speaking actively limits their business, often without them realizing that's what's happening. His diagnostic lens centers on two questions: where is this person's actual starting point, and how committed are they to closing the gap. Key Takeaways Presence functions as a multiplier, not a bonus. High presence with low execution can open doors execution alone cannot — and the reverse is also true: strong execution without presence caps how far a leader rises.The higher you rise, the more a presence gap costs you. A widening disparity between a leader's execution level and their speaking level becomes more visible and more costly the more senior they become.Confidence and bravado look identical from the outside — until they're tested. Confidence is grounded trust earned through real capability; bravado is the same display without the substance behind it.The opposite of fear isn't confidence — it's action. Waiting to feel confident before speaking up keeps leaders stuck; taking action is what actually closes the gap.Most feedback loops are broken by design. Asking people who aren't equipped to evaluate you produces false confidence — CEOs need to benchmark against the level they're trying to reach, not the room they're standing in. 00:00 Why CEOs Need Communication 03:03 The CEO’s Core Responsibility 04:09 Mike Acker’s Communication Journey 05:19 Execution Versus Executive Presence 07:22 What Presence Really Means 11:22 Confidence Versus Empty Bravado 12:50 Understanding the Roots of Fear 15:44 Why Action Defeats Fear 19:54 Communication Requires a Process 24:18 Consistency Beats Intensity 26:23 Transforming a Fearful CEO 34:40 Getting Honest Communication Feedback Mike Acker Executive communication coach; founder, Up Level Communication Up Level Communication https://uplevelcommunication.com/ https://www.linkedin.com/in/mikeackerdotcom/

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About

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 companies, helping leaders navigate moments when complexity increases, tradeoffs become unavoidable, and the cost of misalignment rises. He brings a peer-level perspective shaped by that experience, focusing conversations on the inflection points that materially change a company’s trajectory. The Breakout CEO podcast reflects his approach with candid, operator-level discussions centered on real decisions rather than retrospective storytelling or promotion. Guest Participation - We feature a limited number of CEOs leading scaling companies with meaningful, first-hand breakout moments. If you believe your story would add value for an audience of scaling CEOs, please apply here: https://go.intellectualstrategies.com/ Media & Event Partnerships - For press access, on-site recording, or event collaboration inquiries, please contact us. We record a limited number of on-site conversations at select events with CEOs and founders whose stories align with the podcast’s focus on leadership, strategy, and execution.

Information

  • Creator
    Jeff Holman, General Counsel for Scaling CEOs and Founders
  • Years Active
    2025 - 2026
  • Episodes
    101
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Intellectual Strategies
  • Show Website
    The Breakout CEO