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. -1 h

    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

  2. -2 dias

    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/

  3. 30/07

    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

  4. 23/07

    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

  5. 16/07

    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

  6. 9/07

    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/

  7. 2/07

    78 -Why Most Service Companies Sell the Wrong Thing

    Most service companies lead with what they do. The ones that grow the fastest lead with the problems they solve. In this episode of The Breakout CEO Podcast, Mike LaVista, Founder & CEO of Caxy Interactive, explains how one shift in positioning transformed his consulting business from transactional projects into strategic partnerships, dramatically increasing deal size and changing the conversations he was having with CEOs. Along the way, he shares why niching down creates premium businesses and how AI should be viewed as an amplifier of strategic thinking—not a replacement for it. For years, Mike LaVista described his business the same way most service companies do: by listing the services it offered. It wasn't until he reframed the conversation around customer problems that everything changed. That single realization reshaped Caxy's growth, leading to larger engagements, stronger executive relationships, and a much clearer market position. Mike walks through the decision behind that shift, why specialization creates opportunity rather than limitation, and how asking better questions builds trust long before a proposal is ever written. The conversation also explores the practical role AI is playing inside modern businesses. Rather than focusing on automation alone, Mike argues that AI is most valuable when it helps leaders think better, explore more possibilities, and strengthen the capabilities that already make their organizations successful. 00:00 – Musician Turned Tech Entrepreneur 02:55 – Luck Landed Their First Client 06:29 – Performance Skills Built Better Leaders 12:31 – Developers Need Leaders Who Understand 17:54 – AI Should Empower Human Talent 21:46 – CEOs Need AI Thinking Partners 24:29 – Small Teams Can Compete Bigger 27:44 – Focus Before Building New Businesses 33:59 – Sell Problems, Not Your Services 40:05 – Better Questions Command Premium Prices 44:11 – Niching Down Creates Massive Growth 47:12 – Fear Stops Great Companies Growing Key TakeawaysStop describing your services and start leading with the business problems you solve. Specialization creates credibility, stronger referrals, and premium pricing. The best sales conversations begin with better questions, not better presentations. AI is most powerful when it strengthens strategic thinking instead of simply automating existing work. Great positioning makes it easier for customers to understand exactly why they should choose you. Guest InformationMike LaVista Founder & CEO, Caxy Interactive Website: https://caxy.com LinkedIn: https://linkedin.com/in/mikelavista Host Jeff Holman The Breakout CEO Podcast

  8. 30/06

    77 - How Better Hiring Decisions Create Better Companies

    Every CEO knows people matter. Fewer recognize that hiring is one of the highest-leverage strategic decisions they make. In this episode of The Breakout CEO Podcast, Fletcher Wimbush shares why building a better company starts with building a better hiring system. From hiring for integrity over raw talent to eliminating "talented terrors" and staying relentlessly focused, Fletcher explains how better hiring decisions shape culture, execution, and long-term growth. Fletcher Wimbush is the Founder and CEO of Discovered, a talent acquisition platform that helps organizations make smarter hiring decisions. His perspective comes from decades of leading teams, interviewing thousands of candidates, building recruiting systems, and growing multiple businesses through disciplined leadership. In this conversation, Fletcher explains why hiring isn't simply an HR function—it's one of the most important strategic responsibilities of a CEO. He shares lessons from taking over his father's business, separating two competing business models to unlock growth, building a SaaS platform, and acquiring complementary technology to create an end-to-end hiring solution. Whether you're making your next executive hire or scaling from 20 employees to 500, this episode demonstrates how better hiring decisions create better companies. Key Takeaways Hire for integrity and attitude before experience or technical skill. Great hiring systems reduce turnover, improve culture, and compound business performance. Focus is often the biggest growth strategy—doing fewer things exceptionally well creates leverage. "Talented terrors" usually cost far more than they contribute. Strong reference checking remains one of the most underused tools in executive hiring. 00:00 Why Every Business Is Really in the People Business 01:25 Leadership Lessons That Started at Sixteen 05:30 Growing Up with an Executive Coach as a Father 09:45 Taking Over the Family Business After Tragedy 12:40 Why Integrity and Attitude Beat Talent Alone 17:45 Learning to Hire Through 10,000 Candidate Interviews 22:30 The High Cost of Keeping "Talented Terrors" 26:30 The Hiring Question That Reveals Everything 31:50 Splitting One Business into Two—and Doubling Revenue 36:00 Building a Hiring Platform and Acquiring Integrity First 47:40 How Better Hiring Creates Better Business Results 56:35 The Power of Focus for Every Scaling CEO Guest Information Fletcher Wimbush Founder & CEO, Discovered.ai LinkedIn: https://www.linkedin.com/in/fletcherwimbush Company: https://www.discovered.ai

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Sobre

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.

Informação

  • Autoria
    Jeff Holman
  • Anos em atividade
    2025 - 2026
  • Episódios
    84
  • Classificação
    Para todos
  • Copyright
    © Copyright 2025 Intellectual Strategies
  • Site do programa
    The Breakout CEO