The Breakout CEO

Jeff Holman, Fractional General Counsel for CEOs and Founders
  • 0.0 (0)
  • Entrepreneurship
  • Updated twice 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. 3 days ago

    86 - The Pivot This Founder Made After an Investor Called It Impossible

    Every scaling e-commerce business eventually collides with the same silent problem: customers who don't get what they ordered, when they were promised it. Jevon Le Roux, CEO and co-founder of Keeyu, lived that problem firsthand before building a company to solve it — and along the way, a well-known investor told him it couldn't be done. In this episode, Jevon breaks down why customer service has been built backwards for twenty years — reactive instead of preventive — and what it actually took to pivot his company's entire product, burn through almost all of its cash, and keep raising with five thousand dollars left in the bank. Jevon Le Roux isn't a typical software CEO. Before co-founding Keeyu, he built and exited a business, became a professional surfer, and later earned an executive MBA at HEC Paris — all without finishing high school. That unconventional path shaped how he approaches problems: get to the root cause, then build the plan. At Keeyu, Jevon and his co-founders are tackling the "where is my order" (WISMO) problem that quietly costs e-commerce businesses billions in lost revenue every year. His firsthand experience running e-commerce operations — including a crisis where a thousand customers ordered products that didn't exist in the warehouse — convinced him the industry's approach to customer service was solving the wrong problem. This episode traces the pressure, doubt, and near-failure behind that conviction, and the decision to keep building when it would have been easier to stop. Key Takeaways Believing a problem is real matters more than believing your first solution is right. Jevon's team built a "vitamin" before they built a "painkiller" — and had to rebuild multiple times before the product matched the pain.Skepticism from experienced voices isn't a signal to stop — it can be the reason to keep going. When a well-known e-commerce investor called the WISMO problem impossible to fix, that became the founding team's reason to fix it.Reactive customer service can't prevent the problems it's built to handle. A help desk, like a hospital ER, can only triage after something's already gone wrong — the real opportunity is preventing the failure upstream.Running low on money tests belief in the problem, not just the business. Keeyu's founders kept raising — and kept building — with roughly five thousand dollars left in the bank.Creating a new category means selling the story before the market has a name for it. Convincing buyers, users, and economic decision-makers all requires a different pitch for each. 00:00 The $213B e-commerce problem 00:14 Meet Jevon Le Roux of KEEYU 03:02 Why late orders silently lose customers 05:34 Solving an “impossible” problem 08:36 The customer crisis that sparked KEEYU 12:35 From internal tool to startup 15:47 Early product lessons and pivots 18:11 Turning detection into automation 23:15 Reinventing customer support 31:23 Building through failure and near-zero cash 36:07 Fundraising, traction, and resilience 45:07 Advice for founders and CEOs About the Guest:Jevon Le Roux is the founder of Keeyu, an Ecommerce Operations company. You can find Jevon at https://keeyu.com

  2. 5 days ago

    85 - The CEO Who Set Out to Change Policing Without Using More Force

    What happens when someone reaches the top of the financial world—only to realize success isn't enough? In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Scot Cohen, CEO of WRAP, to explore the deeply personal journey that led him from a successful career in finance to building a company focused on reducing harm in public safety. Scot shares why he walked away from Wall Street, the leadership lessons he learned after losing sight of his purpose, and how listening to customers—not assumptions—reshaped WRAP's strategy. He explains why training, culture, and evidence matter more than technology alone, and why the best CEOs are willing to challenge their own beliefs when the data tells a different story. Whether you're leading a high-growth company or navigating your own inflection point, this conversation is a masterclass in purpose-driven leadership and making difficult decisions that create lasting impact. In This Episode Why financial success didn't bring fulfillment The decision to leave Wall Street and build WRAP The leadership challenges of scaling a mission-driven company How customer feedback transformed WRAP's strategy Why training and culture outperform technology alone Leading with purpose instead of ego Building trust in one of the world's most scrutinized industries What CEOs can learn about making better decisions under pressure About Scot Cohen Scot Cohen is the CEO of WRAP, a public safety technology company focused on equipping law enforcement and first responders with tools and training designed to reduce injury and save lives. After a successful career in finance, Scot shifted his focus to building mission-driven technology that emphasizes better outcomes through innovation, training, and leadership. Connect with Scot Cohen LinkedIn: https://www.linkedin.com/in/scot-cohen-643181375/ Company: https://wrap.com

  3. 6 Aug

    84 - The CEO Playbook for Building Trust Before You Build Demand

    What separates companies that become market leaders from those that remain just another product? In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Romney Williams, entrepreneur, inventor, and CEO of DRYOUT, to explore the leadership decisions behind building a category-defining business. Drawing from decades of experience launching companies, protecting intellectual property, and partnering with global brands, Romney shares why breakthrough growth isn't driven by better marketing—it's built on trust, credibility, and solving the right customer problem. From discovering an unexpected business model through customer conversations to building competitive moats beyond patents, Romney offers a candid look at the realities of scaling a company while making high-stakes decisions with imperfect information. Whether you're leading a startup or scaling an established business, this episode is packed with practical lessons on innovation, resilience, and long-term value creation. Key TakeawaysWhy trust often becomes a company's greatest competitive advantageHow listening to customers uncovered an entirely new business modelThe difference between protecting innovation and building a lasting brandHow successful CEOs make decisions despite uncertaintyWhy intellectual property alone isn't enough to sustain growthLessons from building partnerships instead of simply selling productsHow lifelong learning improves executive decision-makingWhy founders should embrace uncertainty instead of waiting for perfect clarity 00:00 Finding Joy in the Building Journey 01:17 Romney’s Career Thread Across Four Companies 03:16 From Digital Cameras to Industry Disruption 07:15 Why Founders Need Trusted Leadership Partners 12:43 Celebrating Milestones While Scaling a Business 14:15 Finding DryOut and Partnering With Its Founder 16:21 How Intellectual Property Creates an Unfair Advantage 19:08 The Accidental Invention Behind DryOut 22:09 Building the Gore-Tex of Moisture Removal 29:10 Evolving From Consumer Brand to Ingredient Brand 36:45 The Board Meeting That Changed DryOut’s Direction 59:16 Scaling Through Brand Partners and Military Applications About Romney WilliamsRomney Williams is the CEO of DRYOUT, an innovation company focused on moisture removal technologies. Throughout his entrepreneurial career, he has founded and scaled multiple businesses, developed extensive intellectual property, and built strategic partnerships with leading brands. His work centers on transforming breakthrough innovations into scalable commercial platforms by combining product development, trust, and long-term strategic thinking. Connect with Romney LinkedIn: https://www.linkedin.com/in/romneyw

  4. 4 Aug

    83 - The Founder Lesson That Every CEO Should Hear About Customer Feedback

    What if your biggest growth opportunity wasn't your product—but your customers? In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Julie Tylman, Co-Founder and Co-CEO of Group Together, to discuss how relentless customer listening shaped every major decision in her company's journey. Julie shares how a simple idea to simplify group gifts evolved into an international business, why their biggest product breakthroughs came from customer feedback—not founder assumptions—and how one bold decision during COVID accelerated growth and opened the door to the U.S. market. She also reflects on the leadership lessons she's learned along the way, including why staying close to customers has made her a better CEO. Whether you're building a startup or leading a scaling company, this conversation is a masterclass in customer obsession, product evolution, and making better founder decisions. 00:00 Introduction 03:15 The idea behind Group Together 09:40 Building the first MVP 17:20 Learning from customer behavior 26:15 Early hiring mistakes 33:40 The COVID pivot 41:20 Product-market fit and explosive growth 49:10 Expanding into the United States 57:45 Customer service and leadership 01:04:30 Final CEO lessons Connect with Julie Tylman Website: https://grouptogether.com LinkedIn: https://www.linkedin.com/in/julie-tylman-8a160977/

  5. 30 Jul

    82 - Why AI Won't Replace Great Real Estate Professionals

    Artificial intelligence is transforming nearly every industry—but according to Sheldon Wolf, AI isn't here to replace real estate professionals. It's here to empower the ones who embrace it. Drawing on more than 35 years of experience in real estate investing, development, brokerage, and PropTech, Sheldon explains why the future belongs to leaders who understand customer behavior, not just technology. He shares how every major shift—from fax machines to AI—has rewarded those willing to adapt while leaving others behind. The conversation explores why most companies solve today's problems instead of tomorrow's, how customer acquisition drives every successful business, and why controlling the customer journey has become the greatest competitive advantage in real estate. Whether you're building a brokerage, scaling a SaaS company, or leading through technological change, this episode offers practical lessons on innovation, customer-centric thinking, and long-term strategic execution. Key Takeaways AI is a competitive advantage for professionals who know how to use it.Businesses should focus on customer behavior before building new technology.Companies that solve future problems outperform companies solving today's problems.Revenue follows customer acquisition—not the other way around.Great CEOs continually adapt while keeping the customer at the center of every decision. About the Guest Sheldon Wolf is the Founder and CEO of Intellitary AI, a PropTech company using artificial intelligence to modernize customer acquisition and the real estate buying journey. With more than three decades of experience spanning brokerage, investing, development, and technology, Sheldon has built and scaled multiple businesses while advising organizations through periods of rapid growth and transformation. His current focus is helping brokerages leverage AI to improve customer experiences while preserving the value of real estate professionals. Connect with Sheldon Wolf Website: http://www.intellitary.com LinkedIn: https://www.linkedin.com/in/sheldon-wolf-95011520

  6. 23 Jul

    81 - Why Speed Beats Perfection in Healthcare Startups

    What does it take to leave a successful corporate career and build a healthcare startup from scratch? In this episode of The Breakout CEO Podcast, Seth Merritt shares how a side project became Welby Health, a fast-growing healthcare technology company transforming chronic care management. Seth explains why moving quickly—not perfectly—became his competitive advantage, how customer conversations shaped every major product decision, and why founders should stop waiting for the "perfect" business plan before taking action. Along the way, he discusses fundraising, validating ideas, moving up-market, building an enterprise business, and the realities of leading a company through uncertainty. Whether you're a founder, CEO, or executive leading innovation inside a larger organization, this episode offers practical lessons on building faster, learning sooner, and making better decisions. Key Takeaways Why speed is a competitive advantage in healthcare.The importance of talking to customers before building products.How Welby Health evolved from a side project into a venture-backed company.Why founders should launch imperfect products and iterate quickly.Lessons learned from moving from SMB customers to enterprise healthcare systems.The mindset required to scale a startup while remaining customer-focused.Why profitable growth matters more than growth at all costs. Chapter Markers00:00 Why Speed Beats Perfection in Healthcare 01:17 Delivering Faster Impact for Healthcare Customers 08:06 Why Seth Schedules Weekly Tinker Time 10:47 How WellBe Health Supports Chronic Care 15:30 Validating Ideas Through Real Customer Conversations 20:25 Turning an MBA Project Into a Business 22:34 From First Customer to Full-Time Founder 26:25 Scaling WellBe Health to 75 Employees 28:09 Moving Upmarket to Enterprise Healthcare Customers 33:15 Competing Against Best-in-Class Healthcare Companies 40:12 AI, Profitability, and WellBe Health’s Future 42:59 Start Before Everything Feels Perfect Resources Mentioned Welby Health https://welbyhealth.com/The $100 Startup by Chris Guillebeau

  7. 16 Jul

    80 - The Signals CEOs Miss Before Growth Breaks Their Team

    As companies scale, the first signs of trouble rarely appear on a dashboard. They show up in stretched teams, founder bottlenecks, and hiring decisions that lag behind growth. In this episode of The Breakout CEO Podcast, David Khim, Co-Founder of Omniscient Digital, explains why CEOs need to pay attention to qualitative signals before traditional metrics catch up. Drawing from his own experience scaling a bootstrapped agency through rapid growth and AI-driven industry disruption, David shares how a change in hiring philosophy—and in his own leadership—helped unlock the company's next stage of growth. Episode Description Rapid growth can hide organizational strain until it's too late. David Khim discusses how his team reached a point where they had to turn away new business because they had optimized for efficiency instead of capacity. That realization changed how Omniscient Digital hires, plans, and leads. The conversation also explores why experienced leaders increasingly rely on qualitative observations alongside KPIs, how AI is reshaping service businesses, and why founder growth ultimately determines company growth. Rather than treating ambiguity as something to avoid, David argues that CEOs should learn to recognize it as an opportunity to build stronger organizations before cracks begin to show. Key Takeaways Watch for qualitative signals—team capacity, stress, and leadership bandwidth—before the metrics reveal a problem.Hiring ahead of demand can prevent growth from stalling when opportunities arrive.Founder development often becomes the limiting factor in organizational growth.AI changes how work gets done, but judgment remains a CEO's competitive advantage.Building capacity requires intentional decisions before they're financially comfortable. Before the main episode, David joined us for an informal icebreaker conversation about how he recharges outside of work, why he schedules solo CEO retreats, and the routines that help him process difficult decisions. Watch the Icebreaker on The Breakout CEO LinkedIn page: https://www.linkedin.com/company/the-breakout-ceo/ 00:00 AI Is Changing Business Faster Than Ever 00:40 Meet David Khim of Omniscient Digital 05:18 From Chemistry to Organic Growth 11:42 Scaling from Startup to Growth Company 13:17 The Hiring Mistake That Limited Growth 18:27 Avoiding the Founder-Made Trap 20:34 Why Strong Co-Founder Relationships Matter 24:01 Why Every CEO Needs Outside Support 29:15 Helping Clients Navigate AI Disruption 32:13 Building AI Systems That Create Leverage 34:54 Charging for Outcomes, Not Output 39:58 Grace and Space for Better Leadership Guest David Khim Co-Founder, Omniscient Digital Website: https://www.omniscientdigital.com LinkedIn: https://www.linkedin.com/in/davidlykhim Host Jeff Holman Host, The Breakout CEO Podcast

  8. 9 Jul

    79 - The Leadership Shift That Helped Build a Billion-Dollar Company

    What separates CEOs who build enduring companies from those who simply manage growth? For Vikas Sehgal, the answer wasn't a better strategy or a more aggressive sales process. It was a fundamental shift in how he viewed leadership. After helping build Nagarro from a living room startup into a global technology company, Vikas discovered that sustainable growth comes from shared values, empowering great people, and solving customer problems before trying to sell solutions. In this episode of The Breakout CEO Podcast, Vikas reflects on the leadership lessons forged through the 2008 financial crisis, why his team chose shared sacrifice over layoffs, how that decision reshaped their culture, and how those same principles now guide hyperDart as it reimagines the future of search through AI and creator-first economics. Key TakeawaysWhy shared values matter more than organizational hierarchy when scaling a company.How choosing pay reductions over layoffs strengthened culture during the 2008 financial crisis.Why the best sales organizations begin by solving customer problems—not chasing opportunities.The leadership transition from controlling outcomes to enabling great teams.Why entrepreneurship can only be learned by building, not by waiting for perfect conditions. Episode Chapters00:00 From Living Room Startup to Billion-Dollar Company 02:10 Why Shared Values Beat Vision Every Time 10:35 Great Ideas Come From Every Corner of the Company 16:50 The 2008 Crisis That Changed Nagarro Forever 25:58 Stop Selling and Start Solving Customer Problems 34:46 Why Taking Time Off Made Him a Better Founder 44:41 Why Search Is Broken and hyperDart Can Fix It 55:57 Building an AI-First Search Platform 01:03:37 Why Knowledge Creators Are the Real Customers 01:08:10 The Right Time to Start Never Comes 01:10:15 Building Confidence One Challenge at a Time 01:12:04 Final Advice for Every Aspiring Entrepreneur Guest Vikas Sehgal Founder & CEO, hyperDart Former CEO & Co-founder, Nagarro LinkedIn https://www.linkedin.com/in/vsehgal/ Website https://hyperdart.com/ Host Jeff Holman The Breakout CEO Podcast LinkedIn https://www.linkedin.com/company/the-breakout-ceo/

See All (86)

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, Fractional General Counsel for CEOs and Founders
  • Years Active
    2025 - 2026
  • Episodes
    86
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Intellectual Strategies
  • Show Website
    The Breakout CEO