The Breakout CEO

Jeff Holman
  • 5.0 (3)
  • Entrepreneurship
  • Updated Weekly

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. 10h ago

    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 founders should rethink investor communication, and why AI-driven presentation formats are rapidly changing the expectations around fundraising and growth. George Dubec is an entrepreneur, author, networking strategist, and advisory board member for America’s Real Deal — a streaming investment show that combines investor pitches, crowdfunding, and consumer visibility. Drawing from decades of business experience and exposure to startup funding environments, George shares what he believes investors actually evaluate when deciding whether to back a company. The conversation explores why founder credibility matters more than polished decks, how networking directly influences funding opportunities, and why CEOs need to adapt quickly to AI-driven communication and operational shifts. George also explains how investor psychology is changing in an increasingly crowded and attention-constrained market. Key Takeaways Investors increasingly evaluate founder credibility before they evaluate pitch materials.Short-form video presentations can create stronger investor trust signals than traditional pitch decks.Networking remains one of the most underutilized funding advantages for growth-stage CEOs.CEOs who delay AI adoption risk falling behind in communication, productivity, and operational leverage.Strong decision-making increasingly depends on filtering emotion from judgment and focusing on verified information. George Dubec Entrepreneur, Author, Networking Strategist, and Advisory Board Member at America’s Real Deal Website: http://www.georgedubec.com/https://theultimatenetworker.com/ LinkedIn: https://www.linkedin.com/in/georgedubec

    27 min

  2. 5d ago

    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 founders prioritize retained earnings, culture, and long-term sustainability over short-term payouts. For CEOs navigating growth decisions, this episode offers a candid look at the tradeoffs between taking cash out of the business and building something larger over time. Lindsey Prater is the co-founder of Groovy Peach Piercing Co., a Utah-based retail and service business that has grown from a single salon suite into a company with multiple locations, eighteen employees, and millions in annual revenue. Rather than pursuing rapid growth through leverage, Lindsey and her team focused on disciplined reinvestment, values-driven hiring, and creating an experience customers actively seek out. Along the way, she learned firsthand how retained earnings can create strategic flexibility, why culture becomes increasingly important as a business scales, and how sustainable growth often requires delaying personal rewards. This conversation explores the decisions behind that growth, the lessons learned from building a bootstrapped business, and the leadership mindset required to keep investing in the future. Key Takeaways 1. Retained earnings create strategic flexibility. Leaving money in the business gave Groovy Peach the ability to expand without relying heavily on outside financing or debt. 2. Customer demand should guide expansion decisions. The company's first growth decision came after recognizing strong demand, booked-out schedules, and meaningful customer impact. 3. Sustainable growth requires deliberate tradeoffs. Choosing long-term business health over short-term distributions allowed the company to build reserves, reduce risk, and scale confidently. 4. Culture becomes a growth multiplier. Values-aligned hiring and leadership development enabled Groovy Peach to expand beyond its founders. 5. Defining company values improves hiring decisions. Formalizing values transformed culture from something intuitive into a repeatable system for selecting and developing team members. 00:00 Bootstrapping with retained earnings 00:29 Meet Lindsey Prater of Groovy Peach 02:48 The first “we’re going to make it” moment 04:10 Reinventing the piercing experience 08:36 Scaling to three studios 09:00 Sourcing jewelry in China 15:40 Early growth milestones 18:21 The power of retained earnings 20:22 Revenue growth and sustainability 24:42 Hiring the right people 27:03 Defining company values 33:38 The story behind “Groovy Peach” Guest & Host Information Guest Lindsey Prater Co-Founder Groovy Peach Piercing Co. Website: https://groovypeachpiercingco.com/ LinkedIn: https://www.linkedin.com/in/lindsey-prater-50564b276/ Host Jeff Holman Founder, Intellectual Strategies

    41 min

  3. Jun 9

    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 startup support infrastructure continues to fail founders, how fragmentation creates operational drag across the ecosystem, why AI will accelerate both disruption and consolidation, and why scaling organizations must rethink how they support entrepreneurs. He also shares lessons from building Startup Science, his research into startup lifecycle patterns, and why “doing nothing” is often the biggest competitive threat companies face. Key Takeaways Why fragmented startup ecosystems create hidden founder failureThe operational bottlenecks limiting accelerators and incubatorsWhy “do nothing” is often the biggest competitor to changeHow AI is accelerating both fragmentation and consolidationThe difference between data, information, and wisdomWhy first-mover advantage may actually become a disadvantageThe startup lifecycle framework Gregory built after years of researchWhy founders often fail because they don’t know where they are in the journey 00:00 — Introduction To Gregory Shepard 02:05 — Growing Up In Extreme Poverty 04:45 — Discovering Industry Expansion Cycles 07:35 — First Mover Disadvantage Explained 10:10 — Startup Ecosystem Fragmentation Problems 12:10 — AI Driven Market Consolidation 15:05 — Why Human Judgment Still Matters 18:45 — Building Startup Science Platform 22:05 — Scaling Entrepreneur Support Organizations 25:10 — Platform Infrastructure For Founders 28:10 — Measuring Ecosystem Success Outcomes 30:05 — Fighting Organizational Inertia 33:05 — Change Management And Migration 35:20 — The Future Of Work 40:10 — Building The Startup Life Cycle Guest InformationGregory Shepard Founder, Startup Science https://startupscience.com https://www.linkedin.com/in/gregshepard

    47 min

  4. Jun 4

    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 ownership culture inside a scaling company. “It's much better to let one person go to keep this thing safe than to continue to harm this and put everyone in jeopardy.” Drew Allen is the CEO of Grace Technologies, an industrial safety and electrical solutions company serving customers globally across industrial and data center markets. In this conversation, Drew walks through the leadership lessons that reshaped how he operates as a CEO — from a major product failure early in his career to the realization that scaling required rebuilding leadership capacity, aggressively upgrading talent, and redefining organizational standards. The discussion explores decision-making under pressure, the emotional reality of organizational change, the challenge of hiring high-performance teams, and why ownership culture became foundational to the company’s next stage of growth. Along the way, Drew also shares how travel, long-distance trekking, and curiosity shaped his approach to leadership and problem solving. Key TakeawaysScaling often requires rebuilding the leadership team that originally built the company.Organizational bottlenecks are frequently talent and capacity problems disguised as operational issues.CEOs must separate personal loyalty from responsibility to the long-term health of the business.Ownership cultures emerge when leaders empower teams with real responsibility and accountability.Product failures become transformational when leaders stop blaming others and examine their own assumptions. Episode Outline1:00 - Welcome: Drew Allen of Grace Technologies 2:07 - Trekking the Camino de Santiago 4:00 - Walking Through Life's Big Questions 6:19 - Travel, Adventure & Business Mindset 8:04 - Growing Up with a Risk-Taking Dad 13:35 - Drew's Unconventional Path: College at 16, Hong Kong at 20 17:42 - Making It on His Own & Lessons from 3M 20:14 - Joining the Family Business & a $400K Mistake 29:29 - Taking Over as CEO in 2021 32:07 - Rebuilding the Leadership Team 39:00 - The Three Support Systems That Made It Work (Board, YPO, Coaching) 48:57 - Targeting $100M & Grace Technologies' Mission: Zero Harm, Zero Downtime Guest & Host InformationDrew Allen CEO — Grace Technologies Website: https://www.graceport.com/ LinkedIn: https://www.linkedin.com/in/drewallen Jeff Holman Host — The Breakout CEO Podcast LinkedIn: https://www.linkedin.com/company/the-breakout-ceo/

    56 min

  5. Jun 2

    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 reframing and organizational resistance, this conversation focuses on how CEOs can begin AI transformation without attempting to overhaul everything at once. “The technology is moving faster than human trust.” Torian Richardson, co-founder of DBR77, brings a global perspective shaped by leadership roles across manufacturing, education, AI infrastructure, and international business development. Drawing from experiences spanning Africa, China, NVIDIA, and industrial transformation consulting, he explains why small and mid-sized manufacturers face a uniquely urgent opportunity to modernize operations while remaining grounded in practical implementation realities. Rather than treating AI as a software trend or abstract future technology, Torian frames AI infrastructure as a leadership and systems problem: how organizations gather data, make decisions, and adapt operationally under accelerating change. The conversation also explores the human side of transformation — including listening, caregiving, trust, and organizational readiness. 00:00 — AI is moving faster than human trust 01:59 — The origin story behind DBR77 04:05 — Guangxi and universal human connection 12:53 — Why small manufacturers need digestible transformation 17:34 — Making AI real in the physical world 21:56 — Finding the first measurable bottleneck 24:48 — Governance, leadership, and human-in-the-loop AI 26:30 — DBR77’s milestones and Innovation Exchange 28:36 — Overcoming resistance to AI adoption 35:16 — Digital twins as decision-making tools 39:29 — Speed of change and marketing challenges 50:54 — Listening, caregiving, and the future of DBR77 Key TakeawaysAI adoption pressure is accelerating faster than most manufacturing organizations’ decision-making structures.Successful transformation starts with measurable operational visibility, not massive enterprise-wide overhauls.Digital twins are evolving from optimization tools into decision-making infrastructure for manufacturers.Organizational resistance to AI is often rooted in leadership mindset and change management, not technology limitations.Manufacturers that learn to integrate operational data recursively will compound advantages over time. Guest InformationTorian Richardson Co-Founder, DBR77 / DBR 7.7 USA Website: https://dbr77.com LinkedIn: https://www.linkedin.com/in/torian

    55 min

  6. May 28

    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 explores delegation, self-awareness, company culture, personal identity, and the cost of operating too long without reflection. “If the project does not invigorate you, you will not last.” Jane Monroe is the founder and CEO of Embrace the Grape, a beverage catering company she built after entering the events industry through an unlikely path that included DJing, liquor retail, parenting four children, and learning entrepreneurship in real time. But this episode is less about hospitality and more about the hidden leadership signals CEOs often miss about themselves until external pressure forces clarity. Jane shares the moment she realized her company had begun pulling her away from her original priorities, how delegation changed the trajectory of the business, and why understanding your own blind spots becomes essential as companies scale. The conversation also explores Jane’s “leadership cohesion” framework — a practical way of thinking about self-awareness, hidden behavioral patterns, and the disconnect between how leaders see themselves and how others experience them. Key TakeawaysLeadership blind spots usually accumulate gradually before they become obvious.Delegation becomes a survival skill long before most founders recognize it.Protecting energy and attention is a strategic leadership responsibility, not a personal luxury.Strong company culture often reflects the founder’s level of self-awareness.Founders create better businesses when they stop accepting every client, opportunity, or demand. Chapter Markers:00:00 – From Stay-at-Home Mom to Entrepreneur 04:21 – Thinking Like an Owner Early On 05:56 – The DJ Career That Changed Everything 11:25 – Motherhood, Plate Spinning & Real Priorities 15:08 – Buying a Liquor Store Without Experience 18:49 – The Moment She Chose Family Over Business 22:12 – Creating Kansas City’s First Beverage-Only Catering Company 26:04 – Scaling Fast, Learning Delegation & Surviving COVID 32:34 – How the Business Became a Lifeline During Divorce 39:43 – The “Leadership Cohesion” Framework Explained 47:42 – Discovering She Was an Athlete at 40+ 53:29 – Why Saying “No” to Bad Clients Changed Everything Guest InformationJane Monroe CEO, Embrace the Grape, LLC Website: https://www.keynotejane.com/ LinkedIn: https://www.linkedin.com/in/janemonroe/

    57 min

  7. May 26

    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, Founder and CEO of SmartBarrel, didn’t start by building technology—he started by living the problem. Working in construction, he saw firsthand how unreliable labor data, “buddy punching,” and poor visibility made it nearly impossible to manage costs. Even when the numbers existed, they couldn’t be trusted—and without trust, there’s no real decision-making. This episode walks through the moment that broke the system for him, how he approached solving it from the ground up, and what CEOs miss about labor until it starts destroying margins. It also surfaces a broader leadership pattern: most operational risks don’t show up as obvious problems—they creep in quietly until they compound. As Albert puts it: "We had information, but we never had insight." Key Takeaways Labor cost creep is nonlinear—and easy to underestimateOvertime, inefficiencies, and poor visibility compound faster than expected, making small issues financially material very quickly.Data without trust is operationally uselessIf your inputs are inconsistent or manually manipulated, reporting becomes noise—not a decision tool.Most labor problems are system failures, not people problemsWeak controls, distance from the field, and unclear accountability create environments where bad behavior becomes rational.CEOs wait too long to act on labor signalsBy the time labor cost issues are visible in financials, the margin damage is already done.Control comes from capturing data at the source—not downstreamReliable decision-making requires first-touch accuracy, not post-hoc reporting cleanup. Chapter Markers00:00 Intro Hook: Labor Costs & “Court-Ready” Data 00:14 Welcome to The Breakout CEO Podcast 01:27 What “Buddy Punching” Really Means in Construction 03:57 The Friday Payroll Fraud That Changed Everything 06:49 Why Labor Theft Happens So Easily on Job Sites 09:49 How Overtime Quietly Destroys Profit Margins 14:24 Construction Culture, Leadership & Crew Dynamics 16:52 From Glazing Contractor to Startup Founder 21:07 What SmartBarrel Actually Does 23:23 Building the First Prototype in a Miami Beach Bedroom 27:44 Turning a DIY Tool Into a Real Business 29:08 Surviving COVID by Reinventing the Product 35:11 Leadership Lessons, Risk-Taking & Building the Future Guest & Host Information Albert Bou Fadel Founder & CEO, SmartBarrel https://smartbarrel.io/ https://www.linkedin.com/in/albert-boufadel/ Jeff Holman The Breakout CEO https://www.linkedin.com/company/the-breakout-ceo/

    41 min

  8. May 21

    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 invisible. Rochelle Carrington advises CEOs on performance using a neuroscience-based framework she calls performance drag — the accumulated emotional load that quietly degrades execution over time. Drawing from her work with founders and operators, she explains how most CEOs misdiagnose the problem. They assume friction is strategic or operational, when in reality, it’s driven by unresolved internal pressure. The conversation reframes performance at its root: emotions are not a byproduct of leadership — they are a primary driver of decision quality, speed, and team behavior. For CEOs navigating growth, this creates a different question: not just what should I do? — but what internal state am I operating from when I do it? Key Takeaways 1. Decision quality is constrained by internal state, not just logic Most CEOs rely on reasoning and experience, but unresolved stress directly impacts clarity, speed, and judgment. 2. “Performance drag” accumulates when emotions are not resolved High-performing CEOs move quickly — but in doing so, they often carry unresolved pressure forward, compounding over time. 3. Mindset tools manage symptoms — they don’t remove the cause Traditional approaches like discipline or reframing thinking do not address the underlying emotional drivers of performance. 4. CEO emotional state directly impacts team behavior and execution Teams mirror the nervous system of the CEO — affecting risk-taking, communication, and decision velocity. 5. Removing internal friction restores clarity and accelerates execution When performance drag is reduced, decisions become faster, hiring becomes easier, and growth constraints begin to lift. 06:49 Performance drag and CEO execution 10:53 Emotion vs logic in decision-making 09:28 How stress accumulates in high performers 11:27 Why mindset tools fail to resolve performance issues 18:37 The impact of internal state on hiring and growth 20:46 Applying emotional awareness to execution 25:26 How CEO state shapes team culture About the Guest: Rochelle Carrington Founder, EmotionalBP Website: https://emotionalbp.com LinkedIn: https://www.linkedin.com/in/rochellecarrington/

    30 min
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5
out of 5
3 Ratings

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
  • Years Active
    2025 - 2026
  • Episodes
    72
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 Intellectual Strategies
  • Show Website
    The Breakout CEO