The Breakout CEO

Jeff Holman
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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. 11H AGO

    55 - Why Smart CEOs Still Make Bad Decisions Under Pressure

    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 factors that undermine decision quality — and the simple frameworks CEOs can use to protect their judgment when it matters most. William Holsten is a business mistake prevention specialist and founder of Think Smartly, where he advises CEOs on reducing preventable errors in high-stakes environments. Drawing on a study of 300 entrepreneurs, he focuses on a critical but often overlooked variable in decision-making: the environment in which decisions are made. This conversation reframes how CEOs think about mistakes. It’s not just about making better decisions — it’s about recognizing when your judgment is compromised. As businesses scale, increasing pressure, fatigue, and distraction quietly erode decision quality. Holsten introduces two practical frameworks — STORM and SAFER — that help CEOs diagnose risk conditions in real time and apply simple guardrails to avoid costly, preventable mistakes. Key TakeawaysDecision failure is usually environmental, not intellectual - Even strong strategies break down when decisions are made under stress, fatigue, and distraction.Risk increases when multiple pressure conditions stack- CEOs are most vulnerable when stress, overload, and missing signals compound simultaneously.Protecting judgment is a core CEO capability - High-performing CEOs actively manage how decisions are made — not just what gets decided.Simple guardrails outperform complexity - Slowing down, checking assumptions, and reducing distractions have outsized impact on decision quality.Preventable mistakes are the most expensive ones - The cost isn’t just the mistake — it’s knowing it could have been avoided. 00:00 — Host introduction and guest welcome 00:15 — Guest role and expertise definition 01:06 — Decision environment vs intelligence 01:57 — Background and mistake prevention focus 03:05 — Study design and methodology 05:10 — Key findings on business mistakes 06:37 — Risk levels and environmental conditions 08:01 — CEO risk perception vs reality 09:19 — Slowing down and assumption checking 10:21 — Fatigue and decision quality impact 11:54 — Solo vs supported CEO environments 13:11 — External perspective and feedback loops 14:12 — STORM and SAFER frameworks explained 16:36 — Self-awareness and risk assessment tools 18:54 — Preventable mistakes and cost implications 21:17 — Organizational dynamics and confirmation bias 23:38 — Customer proximity and insight gathering 25:12 — First-time vs repeat founder patterns 26:21 — Closing and contact information William Holsten Founder, Think Smartly Website: https://williamholsten.com/ Quiz: https://MistakeRiskQuiz.com LinkedIn: https://www.linkedin.com/in/william-holsten

    27 min

  2. 1D AGO

    54 - The Three-Part Decision Framework CEOs Need to Cut Through Noise

    Most CEOs don’t struggle with a lack of ideas — they struggle with too many. The real constraint is knowing which decisions actually matter, and which ones are just noise. In this episode, Christiane Schroeder introduces a three-part decision framework to help CEOs cut through complexity, move faster, and lead with clarity — without getting stuck waiting for alignment or delaying action under uncertainty. Christiane Schroeder is a decision-making and leadership advisor who works with CEOs to improve clarity, execution, and team alignment. In this conversation, she breaks down a practical framework built around three recurring decision challenges: separating signal from noise, distinguishing alignment from approval, and acting despite uncertainty. The discussion focuses on why decision-making slows down in scaling companies — not due to lack of vision, but because of overload, misaligned priorities, and hesitation. Her framework provides a structured way to restore momentum by narrowing focus, distributing action, and reframing fear as a necessary part of leadership. Key Takeaways Decision-making quality defines CEO effectiveness - The business cannot move faster than the clarity of its decisions.Signal vs. noise is the first filter - Focus on what you can control and what directly impacts outcomes.Waiting for approval creates unnecessary drag - Teams can move forward on defined workstreams before full alignment.Momentum comes from small, distributed actions - Breaking decisions into smaller steps accelerates execution and engagement.Fear is part of the process — not a stop signal CEOs must act without waiting to feel fully ready. 00:01 — Host introduction and episode framing 00:44 — Decision making importance for CEOs 01:24 — Leadership impact of decision making 02:08 — Introducing three-step decision framework 03:30 — Signal versus noise concept 05:01 — Structuring priorities and timelines 07:31 — Small steps and petite practice concept 08:36 — Breaking big decisions into actions 10:22 — Alignment versus approval distinction 12:05 — Speed and momentum in organizations 13:27 — River crossing and execution analogy 16:08 — Fear versus readiness framework 18:19 — Overcoming fear and taking action 20:14 — Consistency and small-step execution 24:51 — Applying the framework as a CEO 26:10 — Team strengths and delegation insights 29:09 — Unique signals and competitive positioning 30:41 — Framework recap and closing thoughts Guest: Christiane Schroeder Decision-Making & Leadership Advisor (Dr. Christiane) Website: https://doctorchristiane.com/ LinkedIn: https://www.linkedin.com/in/christianeschroeter/ Host: Jeff Holman The Breakout CEO Podcast

    34 min

  3. 2D AGO

    53 - Diagnose Before You Scale: The CEO Discipline Most Skip

    Many CEOs try to fix growth problems by adding more resources—more marketing, more hires, more tools. But according to advisor Jon Bassford, scaling problems rarely come from a lack of effort or investment. They come from failing to diagnose what’s actually broken inside the organization. In this episode, Bassford explains why CEOs must diagnose operational and cultural breakdowns before trying to scale execution. He shares the signals he looks for when organizations stall and a practical process CEOs can use to uncover what’s really slowing growth. 00:01 — Host Welcome And Guest Introduction 01:05 — Bassford Background And Career Path 02:05 — Advisory Work With Scaling CEOs 03:10 — Leadership Mindset Culture Operations Framework 04:30 — Founder Triggers For Operational Help 06:10 — Diagnosing Alignment And Operational Gaps 08:20 — Psychological Safety And Team Voice 10:35 — Leadership Letting Go Of Control 12:10 — Process Mapping As Organizational Tool 15:05 — Operational Alignment And Decision Speed 17:10 — Freedom And Profit Impact For CEOs 19:50 — Fear Habits And Leadership Decision Paralysis 23:10 — Practical Process Mapping Framework 26:10 — Leadership As Orchestra Conductor 27:20 — Closing And Contact Information‍ Jon Bassford Founder & CEO — Lateral Solutions Website: https://think-lateral.com Personal Website: https://jonbassford.com LinkedIn: https://www.linkedin.com/in/jonbassford/ Think you'd be a great guest on the show? Apply https://go.intellectualstrategies.com/ Get in Touch with Jeff Holman ⤵️ Website: https://www.intellectualstrategies.com/ Instagram: https://www.instagram.com/holmantech/ Facebook: https://www.facebook.com/jeff.holman.9678 LinkedIn: https://www.linkedin.com/in/holman/

    29 min

  4. APR 9

    52 - The Moment You Realize Your Product Isn’t the Business Model

    A CEO must recognize when strong product traction masks a weak business model — and reframe the company around how value is actually monetized before growth compounds the wrong path. The episode centers on a critical reframing moment: realizing that product success (downloads, usage) does not equal a viable business model. The conversation develops through tension between B2C traction and B2B monetization, forcing a clear strategic choice under uncertainty. The insight is earned through real signals (low retention, usage behavior) and reinforced by customer feedback, leading to a shift toward an IP-driven platform strategy. Key TakeawaysTraction without retention or monetization is a false positive. CEOs must look beyond surface growth metrics to underlying behavior signals. The real business may sit beneath the product. Reframing around IP or capability can unlock entirely new markets and revenue models. Delaying strategic choices compounds risk. When multiple paths show traction, choosing one early is critical. Hiring too late creates irreversible damage. Burnout and rushed hiring decisions degrade team quality and performance Customer reality is the only reliable signal. The pivot succeeded only after focusing on real problems customers were willing to pay to solve. Chapter Markers00:00 - Intro & guest background 02:00 - Career path (fashion, tech, product roles) 05:00 - Transition from corporate to startup 08:30 - Fashion tech industry overview 10:00 - Role as product “translator” 12:30 - Startup vs corporate speed & learning 14:30 - Initial product (AI wardrobe app) 17:00 - B2C traction vs monetization challenges 20:00 - Pivot decision: B2C to B2B 24:00 - Building an AI “operating system” for fashion 30:00 - Product-market fit & enterprise traction 36:00 - Scaling team & next growth phase Maísa Benatti is CEO of AIUTA, a fashion-tech AI company building enterprise solutions for visual experiences. Her background at Amazon and Farfetch — combined with leading a pivot from B2C to B2B — gives her direct experience navigating product-market fit, monetization challenges, and scaling decisions in AI-driven businesses. https://www.linkedin.com/in/maisabenatti/ https://www.aiuta.com/

    50 min

  5. APR 7

    51 - The Cost of Getting Comfortable Too Early as a Scaling CEO

    Early success creates a false sense of security that hides structural weaknesses—and when disruption hits, only CEOs who take full accountability can rebuild stronger. This episode follows the arc of growth → comfort → blind spots → external shock → internal reckoning → rebuild, showing how success itself becomes the precursor to failure. The conversation sharpens around a single decision: blame external events or take full accountability, and how that choice determines whether a CEO stagnates or evolves. The insight earned is that comfort—not failure—is the real inflection point, and the cost only becomes visible under pressure. Key TakeawaysComfort is a leading indicator of risk When things feel stable, CEOs often stop questioning assumptions—this is when fragility builds. Accountability—not circumstance—determines recovery External shocks trigger collapse, but internal ownership determines what happens next. Scaling dilutes intuition if not actively protected As teams and complexity grow, CEOs risk replacing judgment with over-reliance on data or consensus. Customer proximity is the only reliable ground truth Losing touch with customers is often the earliest—and most ignored—signal of decline. Resilience requires structural diversity, not optimization Businesses optimized around a single model are efficient—but fragile under disruption. Chapter Marker 00:00 - Intro & global background (France, US, Israel) 02:30 - Cultural differences in business communication 05:00 - Early business experience (environmental company & e-commerce) 08:30 - Importance of knowing your customer 10:30 - Intuition vs data in decision-making 16:30 - E-commerce success & hitting growth ceiling 23:00 - Breakout moment through acquisitions 30:00 - Scaling operations & rapid integration 36:30 - Crisis: volcano disrupts global shipping 42:00 - Merchant account shutdown & business setback 44:30 - Radical accountability & rebuilding mindset 50:00 - Lessons: no comfort zone & infinite business thinking Laurent Cohen is the Founder of GetOblic who shares his firsthand experience scaling an e-commerce business, hitting a growth ceiling, breaking through it, and then losing momentum due to structural blind spots exposed by a crisis. https://getoblic.com/

    1h 3m

  6. APR 2

    50 - How Josh Carr Rebuilt Echo Water Into an $18M Hardware Company

    As AI makes software easier to replicate, Josh Carr argues that durable businesses may increasingly come from harder-to-build physical products and hardware companies. Echo Water effectively restarted from scratch, forcing the company to rebuild customers, products, and operations from the ground up. Josh Carr explains why hardware companies are harder to build but often more defensible than software businesses. The conversation reframes entrepreneurship around experimentation, execution, and identifying opportunities where physical products create durable advantage. Scaling CEOs and founders often default toward software or digital businesses because they scale quickly and require less capital. But the episode raises a strategic tension: If AI makes software easier and cheaper to build, where will real competitive advantage exist? Leaders must decide whether to continue pursuing purely digital products or consider opportunities in physical products and hardware where barriers to entry remain higher. Execution reveals strategy. Real insights about markets and products emerge through experimentation and real customer transactions. Hardware businesses are difficult—but defensible. Manufacturing, supply chains, and product design create operational complexity that discourages fast followers. Early sales validate the direction. The first transaction provides critical proof that the market values the solution. AI may commoditize large parts of software. If building software becomes dramatically easier, competitive advantage may shift toward physical products. Innovation often comes from combining unrelated ideas. Entrepreneurs can generate new opportunities by connecting concepts that previously had nothing to do with each other. Chapter Marker: 00:00 - Intro & guest welcome 01:30 - Car restoration & personal background 04:30 - Business turnaround analogy 07:00 - Visionary founder & early hydrogen water 10:30 - Restarting the company from zero 14:00 - Entrepreneur mindset & first sale excitement 17:30 - Team strategy & “mobbing” workflow 21:00 - Product explanation (hydrogen water tech) 26:30 - Scaling the business to $18M 32:00 - Product design & manufacturing challenges 38:30 - Hardware vs software future trends 45:00 - Business ideas, innovation & entrepreneurship advice Josh Carr https://www.linkedin.com/in/superstar/ CEO, Echo Water Josh Carr rebuilt Echo Water into an $18M hardware and health technology company, focusing on hydrogen water and advanced water filtration systems. His experience spans startups, product design, and scaling physical products.

    1h 1m

  7. MAR 31

    49 - The Cost of Scaling a Marketplace With Misaligned Incentives

    Marketplace businesses look simple on the surface: connect supply and demand and let the network grow. But for CEOs, the real risk isn’t growth — it’s misalignment between stakeholders. In this episode, Paul Roberts, CEO of GoodBite, explains why marketplace startups often fail when incentives between customers, partners, and suppliers drift apart — and why scaling too early can make the problem exponentially worse. “At scale, misalignment becomes the most expensive risk.” Drawing from multiple startups and over $130M raised, Roberts shares how CEOs should validate marketplace alignment before writing code, raising capital, or scaling distribution. Marketplace businesses are attractive to founders because of their potential for rapid scale. But behind the growth narrative is a difficult operational reality: every stakeholder in the marketplace must win at the same time. Paul Roberts, serial entrepreneur and CEO of GoodBite, has spent decades building companies across data science, advertising technology, and marketplaces. In this conversation, he explains why the biggest threat to scaling a marketplace isn’t competition or funding — it’s misaligned incentives between the participants in the ecosystem. Roberts shares how lessons from previous startups shaped the design of GoodBite, a food delivery platform that integrates charitable giving into everyday consumer transactions. By aligning incentives across restaurants, consumers, and nonprofits, the model attempts to solve the structural problems that plague many marketplace platforms. The discussion explores how CEOs should think about validating marketplace ideas, making decisions with incomplete data, building leadership teams, and avoiding structural misalignment that becomes expensive once growth accelerates. Key Takeaways 1. Misalignment becomes exponentially expensive at scale Marketplace businesses often move fast early, but structural misalignment between stakeholders becomes costly once growth accelerates. 2. Growth amplifies problems — it doesn’t solve them Scaling a company with weak foundations only exposes the cracks faster. 3. Marketplace CEOs must validate every side of the ecosystem Successful marketplaces require alignment between suppliers, customers, and platform incentives before scaling. 4. CEOs must act before perfect information exists Decision-making at scale requires recognizing signals early and moving with conviction rather than waiting for perfect data. 5. Leadership is about building the right team, not controlling everything Roberts compares the CEO role to a bench coach — responsible for assembling the right team and enabling them to execute. 00:00 Intro hook: misalignment is the most expensive risk 00:15 Welcome to the show + Paul Roberts intro 00:56 Family, entrepreneurship, and bringing business lessons home 03:13 What a CEO can actually control 04:21 The CEO as a “bench coach” 05:57 Paul’s founder background: adtech, data science, and the SPAC 06:48 Why he built GoodBites: food delivery with charitable giving 08:21 Lessons from past companies: alignment, risk, and pattern recognition 12:26 Entering food delivery without restaurant-industry experience 13:42 The GoodBites elevator pitch 15:00 Why now is the right time to build this marketplace 17:16 The problem with traditional delivery apps for restaurants 19:27 Connecting restaurants, consumers, and charities 21:05 Making giving effortless through everyday orders 23:22 Traction, college ambassadors, and growth goals 25:33 What’s working in the rollout 27:04 Restaurant exclusivity deals and market friction 29:18 How campus ambassadors drive local adoption 30:06 User experience: choosing charities, impact tracking, and verification 32:30 Adoption trends and coverage challenges 35:32 Partnering with larger restaurant groups and franchise owners 37:43 Advice for CEOs scaling marketplace businesses 39:03 Alignment, validation, and building the right foundation 42:05 Five-year vision for GoodBites 43:38 How students, restaurants, and charities can get involved 44:17 Paul’s personal charity picks: Alzheimer’s Foundation and ASPCA 45:20 Outro Paul Roberts is the CEO of GoodBite and a serial entrepreneur who has raised more than $130 million across multiple startups. His experience building marketplace and platform businesses informs his perspective on incentive alignment, ecosystem design, and scaling strategy.

    45 min

  8. MAR 26

    48 - The Leadership Shift That Took This CEO From Survival to Scale

    What does it take to scale a company in one of the most competitive industries in technology? In this episode of the Breakout CEO Podcast, Jeff Holman sits down with Michael Chaput, CEO of Endsight, to explore the leadership transformation that helped him grow a managed services company to more than $35 million in revenue and 140 employees. Michael shares the lessons he learned after his first company went bankrupt and how those experiences shaped the leadership philosophy that ultimately fueled Endsight’s growth. The conversation dives deep into the realities of the managed services industry, why most firms never scale beyond a handful of employees, and the critical shift leaders must make from survival mode to strategic leadership. Michael also explains how evolving company values, aligning teams around a shared vision, and creating meaningful work environments can unlock both performance and long-term growth. Along the way, he introduces powerful frameworks—from the Predator vs. Prey mindset in leadership to the Becker Rudder principle, which explains how small internal shifts can transform an entire organization. This episode is packed with insights for founders, executives, and leaders who want to build companies that scale while maintaining strong culture and purpose. Key Takeaways Failure can be the foundation of success. Michael’s first company ended in bankruptcy, but the lessons from that experience helped shape Endsight’s long-term growth.The managed services industry is extremely fragmented. In most cities there are hundreds or even thousands of small competitors, making differentiation and scale difficult.Scaling requires letting go. Founders must eventually delegate even the parts of the business they enjoy most in order to grow the organization.Core values must evolve with the business. Early company values can unintentionally create the wrong culture if they aren’t continually reevaluated.Alignment beats perfect strategy. A team united around a shared vision will outperform a group pursuing multiple competing strategies.Purpose drives performance. Employees perform best when they find meaning and play in their work, not just economic incentives.Leadership starts with the inner game. The most powerful changes leaders can make often begin with their own habits, mindset, and philosophy. Michael Chaput is the CEO of Endsight, a leading managed IT services provider serving hundreds of businesses. Under his leadership, the company has grown to more than 140 employees and $35M in annual revenue in a highly competitive industry. Michael is a longtime entrepreneur and leadership thinker who focuses on building organizations rooted in strong values, team alignment, and continuous improvement. Through his work and writing, he explores how leaders can create meaningful work environments while achieving sustained business success. Chapter Markers 00:00 Intro: Inner Game vs Outer Game 00:17 Podcast Intro & Guest Introduction (Mike Chaput) 01:00 Early Career & First Business Failure 02:08 Lessons from Bankruptcy & Resilience 02:12 What Insight Does Today (Managed IT Services) 03:05 Industry Landscape: Small vs Large Players 04:46 Why It’s Rare to Scale in This Industry 07:52 How Mike Got Into Managed Services 10:54 Early Growth & First Competitive Advantage 12:45 Scaling Challenges & Customer Retention 14:06 Growth Ceilings & Leadership Evolution 16:39 Biggest Leadership Learning Moments 18:35 When Core Values Were Wrong 22:00 Redefining Company Values (Respect vs Humor) 26:26 Setting Vision: Thinking Backwards vs Big Goals 28:46 Why Big Goals Create Energy 29:31 The Turning Point: Why Change Was Necessary 30:49 Prey vs Predator Mindset in Leadership 33:09 Sponsor Break + Podcast Context 33:33 Vision & Values as Team Alignment Tools 36:00 Why Alignment Beats “Perfect Strategy” 38:04 Building Team Trust & Leadership Foundations 40:39 How to Actually Create Core Values 44:17 Why Most Company Values Are Weak 45:17 Learning Through Books & Experience 47:02 Diagnosing Problems Through Values 49:06 How Goals Shape Attention & Behavior 51:18 Capital Strategy: Growth vs Exit Decisions 53:00 Future Direction: AI & Business Transformation Resources Mentioned Unreasonable Hospitality — Will GuidaraThe E-Myth Revisited — Michael GerberBuilt to Last — Jim Collins & Jerry PorrasLean / Toyota Production System principlesSAVERS productivity framework

    1h 19m
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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
  • Years Active
    2025 - 2026
  • Episodes
    55
  • Rating
    Clean
  • Copyright
    © Copyright 2025 Intellectual Strategies
  • Show Website
    The Breakout CEO