Best Bootstrapped Giants Podcasts (2025)

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#455: Jim Carlisle | Boardroom Ownership: Protecting Value, Preserving Legacy, and Capital Allocation 1:17:42

3d ago1:17:42

1:17:42

If your goal is to run your company from the boardroom, the real work isn’t just stepping out of day-to-day operations. It’s making sure the business—and your wealth—are protected no matter what happens. In this conversation with attorney and deal advisor Jim Carlisle. Jim has guided hundreds of owners through sales, ESOPs, continuity crises, and l…

1
EE440 - Mentor Moment: Redefining Success Beyond Money With Sahil Bloom

7d ago

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In this Mentor Moment, Gary Fox speaks with Sahil Bloom — investor, writer, and creator — about how his definition of success has transformed. Once focused purely on financial outcomes, Sahil now measures success through time, people, purpose, and health, seeing money as a natural byproduct rather than the goal. He also shares a refreshing take on …

1
#454: Candice Bradley | Designing the Game You Want to Play: Ownership, Capitalism & Real Decision Making 1:41:01

10d ago1:41:01

1:41:01

If you want to design a business that works for your life — not the other way around — you need to understand the actual game you’re playing. Watch on YouTube In this episode, I sit down with Candice Bradley, a business owner, investor, former banker, and strategic advisor who’s lived through nearly every ownership structure in the capitalist playb…

1
EE439 - From 5 Cafés to 800 Locations: How Bobby Kerr Built and Sold Insomnia Coffee

10d ago

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In this episode of The Entrepreneur Experiment, Gary Fox sits down with one of Ireland’s most recognisable business voices, Bobby Kerr — founder of Perk, former CEO and Chairman of Insomnia, investor, broadcaster, and champion of Irish enterprise. Bobby shares his remarkable journey from starting his first business at 39 — remortgaging his house wi…

1
The Answers Are Hiding in Your Repressed Emotions 48:13

16d ago48:13

48:13

Emotions Are Not the Enemy: Unlocking Leadership, Clarity & Decision-Making Through Feeling ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Most entrepreneurs think their emotions get in the way. But what if they’re actua…

1
#453: Jennifer Davis | From Chaos to Cash: The Comp Plan That Frees You to Lead 1:34:49

17d ago1:34:49

1:34:49

If you’re trying to grow your business without creating a mess of misaligned incentives, resentment, or comp plans that backfire—this episode is for you. I brought Jennifer Davis back on because she built one of the most intentional compensation systems I’ve ever seen. We walk through how she tied her company’s mission and KPIs directly to each per…

1
EE438 - 2 Startups, 2 Exits: Áine Kerr’s Blueprint for Purpose-Driven Success

17d ago

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In this episode of The Entrepreneur Experiment, Gary Fox sits down with Áine Kerr, the award-winning journalist, serial entrepreneur behind startups including Storyful (acquired by News Corp), and Kinzen (acquired by Spotify). From teaching in Dublin classrooms to building Storyful alongside Mark Little, leading global journalism partnerships at Fa…

1
#452: Geoff Woods | Author of The AI-Driven Leader 1:23:32

24d ago1:23:32

1:23:32

What if the success you're chasing isn't the final destination, but the beginning of something more? Watch on YouTube Most business owners I talk to know AI matters—but many are still stuck thinking it’s just for writing emails or something their IT team should handle. That’s not the game we’re playing. In this episode, I sat down with Geoff Woods …

1
EE437 - The €100M E-Commerce Blueprint: Fran Quilty on the Data Every Brand Needs 1:29:40

24d ago1:29:40

1:29:40

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Fran Quilty, co-founder and CEO of Conjura, the analytics platform powering the world’s fastest-growing e-commerce brands. From spinning out Wayflyer to building one of Ireland’s most exciting SaaS companies, Fran shares the unfiltered reality of transitioning from a services b…

1
EE436 - Mentor Moment: From Trading Phones to Powering Teslas: Barry Napier’s $1Bn Story

28d ago

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Barry Napier didn’t follow the typical founder path. In this bite-sized Mentor Moment, he shares how trading phones around the world laid the foundation for building Cubic Telecom - the company he’d go on to sell 51% of for €473 million. From street smarts to striking deals with Tesla, it’s a story of grit, vision, and relentless execution. To list…

1
#451: Paul Spiegelman | The Origin Story of the Small Giants Community 1:12:09

1M ago1:12:09

1:12:09

What if the success you're chasing isn't the final destination, but the beginning of something more? Watch on YouTube This episode is the natural continuation of last week's conversation with Jean Moncrieff, the new leader of the Small Giants Community. But today, we go back to the source to get the full origin story of the Small Giants Community. …

1
EE435 - From €1M in Debt to 1,000 Clients: Inside Ireland’s Quiet Tech Giant 2:11:29

1M ago2:11:29

2:11:29

In this episode of The Entrepreneur Experiment, Gary sits down with Kevin O’Loughlin, founder and CEO of Nostra, one of Ireland’s leading IT services and cybersecurity companies. From being €1 million in debt and living on pasta, to building a company helping 1,000+ businesses across Europe, Kevin shares the deeply personal story behind his mission…

1
EE434 - Mentor Moment: The Mindset Behind Raising $26M with Conor Sheridan, Nory 6:01

1M ago6:01

6:01

In this weekend's Mentor Moment, Conor Sheridan, founder of Nory, shares the mindset shift that helped him go from startup operator to scaling a global restaurant tech company. From embracing boldness in a culture that often discourages it, to mastering the underrated power of “the next logical step,” Conor breaks down the thinking that led to rais…

1
#450: Jean Moncrieff | Letting Go, Leading with Values, and Building a Company That Lasts 1:13:39

1M ago1:13:39

1:13:39

What does it actually mean to build a company that lasts? Watch on YouTube Not just one that grows. Not just one that sells. But one that thrives beyond the founder—because it was built with values at the core. In this episode, I’m joined by Jean Moncrieff, an entrepreneur, coach, and the new leader of the Small Giants Community, for a conversation…

1
EE433 - Raising €4M To Automate the Painful Side of Business 1:22:13

1M ago1:22:13

1:22:13

In this episode of The Entrepreneur Experiment, Gary Fox is joined by Ross and David, the powerhouse duo behind Outmin, a game-changing AI bookkeeping platform. What starts as a conversation about longevity, biohacking, and raw vegetable breakfasts quickly evolves into a masterclass in building a deep-tech startup from scratch. From rejecting vanit…

1
EE432 - Mentor Moment: Why E-Commerce Didn’t Kill the Supermarket 7:33

1M ago7:33

7:33

In this Mentor Moment from Episode 372, David O’Meara, CEO of Greenman Group, unpacks the surprising reality of post-COVID retail: traditional supermarkets aren’t just surviving—they’re evolving. While many predicted the death of brick-and-mortar retail with the rise of e-commerce, David explains why food retail continues to thrive, especially in G…

1
Creative Tension: The Secret to Creating Big Results Without the Grind 51:47

1M ago51:47

51:47

Why do some goals drain you while others inspire action? In this powerful conversation, Jesse Pujji and executive coach Dave Kashen unpack a core concept at the heart of entrepreneurship: the Desired Future State (DFS). They explore how clean motivation, grounded in acceptance and vision—not fear or lack—can transform the way you lead, strategize, …

1
Motorboat Leadership vs. Sailboat Leadership 41:18

1M ago41:18

41:18

[00:00:00] Intro – Jesse hints at a personal and professional transition [00:00:27] Jesse’s life update – spiritual journey and post-Japan reflection [00:01:30] The Motorboat vs Sailboat leadership metaphor explained [00:02:51] Internal conflict: fear of letting go and team dependency [00:04:03] Overwhelm from managing multiple businesses – “a comp…

1
EE431 - €0->€4 Million in 4 Years 2:07:47

1M ago2:07:47

2:07:47

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Cait and Cillian, the powerhouse duo behind Luxury Exchange - the Irish-born fashion resale platform that’s redefining pre-loved luxury. From humble beginnings selling designer pieces on Instagram between her shifts at Brown Thomas, Cat grew her side project into a business pro…

1
#449: Ryan Tansom | Understanding the Meaning of Life, God, and Money 33:28

2M ago33:28

33:28

This episode is different. No guest. No business mechanics. Just me, reading from my journal and unpacking the questions that have been driving my work, my life, and everything behind Independence by Design™. Watch on YouTube A few questions have been front and center for me since my first memories. Why are we here? What’s the point of all this wor…

1
EE430 - Mentor Moment: Luke Joyce: Disrupting a Traditional Industry Through Smart Systems 6:16

2M ago6:16

6:16

In this Mentor Moment from The Entrepreneur Experiment Episode 378, Luke Joyce shares how he’s transformed the traditional window cleaning business using technology, subscriptions, and automation. Luke reveals his vision to scale nationwide, break into the UK, and ultimately build systems that could apply to any home service — all while solving pai…

1
#448: Jennifer Davis | Bootstrapping Davisware to $20M+, Selling to PE, Raising 10 Kids, & Living Exponentially 1:28:42

2M ago1:28:42

1:28:42

Jennifer Davis is the co-founder and former CEO of Davisware, a vertical ERP platform she and her husband started at 17. Over two decades, they scaled it to $20M+ in revenue, built a team of over 200, and sold to private equity. She’s also the mother of ten kids and the author of two books, including Living Exponentially. Watch on YouTube In this c…

1
EE429: The Future of Food: How Gousto Delivers 100 Million Meals a Year 1:08:17

2M ago1:08:17

1:08:17

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Timo Boldt, the visionary founder and CEO of Gousto, the UK’s leading homegrown meal-kit company. From humble beginnings hand-delivering recipe boxes and knocking on doors, to building a data-powered food business that serves millions of dinners annually, Timo shares his 13-yea…

1
Is Spirituality the Missing Key for Founders? 46:37

2M ago46:37

46:37

You're Not Your Inner Voice: Meditation, Spirituality, and Mental Clarity for Founders ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up 00:00 – Jesse introduces the topic: spirituality for entrepreneurs 01:00 – What does s…

1
EE428 – Mentor Moment: Stephen Kinsella on How and When the Next Economic Crisis Will Hit 9:01

2M ago9:01

9:01

In this Mentor Moment, economist Stephen Kinsella joins Gary Fox to break down the patterns behind economic booms and busts - and why the seeds of the next crisis are often sown during the good times. Stephen explains the theory of financial instability, the role of credit, and how euphoria can quickly turn to fear. He also explores what could trig…

1
#447: Jeff Buettner | Q2 2025 M&A Update: What Buyers Want, What’s Holding Deals Back, and How Founders Can Prepare 45:15

2M ago45:15

45:15

What’s happening in the M&A market right now? Who’s buying, who’s selling, and how should owners think about timing, value, and optionality? Watch on YouTube In this episode, I sit down with Jeff Buettner from ButcherJoseph, an investment banker who specializes in founder-led companies in the lower middle market. We unpack the current state of deal…

1
EE427: 100,000 Customers with Zero Marketing Budget: The Story of Seed Golf 1:31:30

2M ago1:31:30

1:31:30

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Dean Klatt, the Australian founder of Seed Golf, who built a global direct-to-consumer golf brand… from Carlow. Dean shares the story of how he reverse-engineered premium golf balls, bootstrapped his way to international markets, and took on billion-dollar brands without a cent…

1
EE426 - Mentor Moment: Working With Your Brain, Not Against It: DC Cahalane on ADHD & Entrepreneurship 7:14

2M ago7:14

7:14

In this bite-sized Mentor Moment, DC Cahalane shares how a late diagnosis of ADHD transformed his understanding of himself — and his work. From battling procrastination to embracing what he once saw as flaws, DC opens up about the mental health rollercoaster that led to a powerful realization: ADHD wasn’t a limitation, it was a lens. He unpacks why…

1
#446: Joe Brown | What Every Owner Should Know About Inflation, Debt, and the Real Economy 1:00:28

2M ago1:00:28

1:00:28

Most owners rely on gut instinct, advisors, or market trends to make decisions, but few stop to ask: What’s actually happening underneath the economy? Watch on YouTube In this episode, I’m joined by Joe Brown—creator of Heresy Financial—for a macroeconomic breakdown that actually makes sense for business owners. We unpack inflation, interest rates,…

1
EE425 - Fetching €40 Million: How Anthony Gallagher Started & Scaled Petstop 1:31:37

2M ago1:31:37

1:31:37

In this episode of The Entrepreneur Experiment, Gary Fox meets Anthony Gallagher - the man behind Petstop, Ireland’s most successful independent pet retailer. From sweeping floors at Penneys to nearly selling his dot-com startup for $42 million (before it all collapsed), Anthony’s story is packed with lessons on grit, resilience, and building somet…

1
Close - Focused CRM does $50 million a year 49:11

2M ago49:11

49:11

[00:00:00] Intro – Andrew sets up the conversation: sales reluctance, AI, and CRM evolution [00:00:47] Steli explains Close's positioning: high-communication CRM for salespeople [00:01:41] Revenue milestone: Close is on track to hit $50M this year [00:02:36] Bootstrapping vs. fundraising: why Close chose profitability over VC [00:04:01] Why staying…

1
EE424 - Mentor Moment: The Power of Relentless Selling with Gary Lavin, Founder of VITHIT 7:37

2M ago7:37

7:37

What do you do when your business is on the brink of collapse? For Gary Lavin, it meant getting in his car and personally selling into 3,500 stores in 18 months. In this raw and honest moment, Gary shares how fear became his biggest motivator, why most people skip the hard (but essential) work of selling, and how doubling your store count can doubl…

1
EE423 - From 25-Seater Café to National Brand: The Gourmet Food Parlour Story 1:36:30

2M ago1:36:30

1:36:30

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Lorraine Heskin, the trailblazing founder of Gourmet Food Parlour, one of Ireland’s most successful independent hospitality groups. Lorraine shares her journey from selling Irish foods on the streets of Manhattan to opening a tiny 25-seater café off a side street in Dun Laoghai…

1
#445: Mark Cleveland | You Don’t Have to Sell or Scale—There’s a Third Option 1:10:36

2M ago1:10:36

1:10:36

We’ve all heard it: “Pick one thing. Focus. Go all in.” But what if that advice doesn’t apply once you’ve built real optionality? Watch on YouTube In this episode, I’m joined by Mark Cleveland—an experienced entrepreneur, investor, and self-described parallel entrepreneur—to rethink how owners can design the next chapter of life. Instead of scaling…

1
EE422 - Mentor Moment: Mental Fitness, Therapy & Legacy - Laura Bonner’s Reset Rituals 5:19

3M ago5:19

5:19

In this Mentor Moment from Episode 365 with Laura Bonner, founder of The Muff Liquor Company, she opens up about the mental practices that keep her grounded in business and life. Laura shares her unapologetic belief in therapy, the importance of taking time to reset, and why legacy isn’t about being a great business person—but a great person. It’s …

1
#444: Clint Fiore | Understanding Main Street Valuations (Through the Buyer’s Lens) 1:36:06

3M ago1:36:06

1:36:06

If you're running a mid-sized company and considering acquisitions—or you just want to understand how smaller companies get valued—this episode is for you. Watch on YouTube I sat down with Clint Fiore, a business broker who’s helped hundreds of Main Street businesses try to sell. And here’s the truth: most of them don’t get what they want. Not beca…

1
EE421 - Email is King: How Rory’s Travel Club Hit 200K Members with a €12 Email Subscription 1:46:22

3M ago1:46:22

1:46:22

In this episode of The Entrepreneur Experiment, Gary sits down with Rory King, the founder of Rory’s Travel Club- a radically simple subscription business that’s quietly revolutionising travel in Ireland and beyond. With no investors, no fancy app, and no startup playbook, Rory turned a €10 Facebook idea into a thriving travel club with over 200,00…

1
EE420 - Mentor Moment: From Stockbroker to Showroom - Nadia Adan’s Leap of Faith 9:38

3M ago9:38

9:38

In this Mentor Moment from episode 370, Nadia Adan shares how she left a high-paying corporate job in finance to launch her own car dealership, Ashford Motors, just before the pandemic. With grit, intuition, and a flair for social media, Nadia built a thriving business from scratch—even as others called her a "backstreet garage." This short episode…

1
#443: Graham & Kyle | How to Value Your Business Without the Bullsh*t 1:46:35

3M ago1:46:35

1:46:35

You’ve probably heard that business valuation is more art than science. But what if the art is just smoke and mirrors—and the science has been hiding in plain sight all along? Watch on YouTube In this episode, I’m joined by Graham Stephen and Kyle McCulloch, the team behind Bizval, a company that’s quietly building a tool that may completely disrup…

1
EE419 - The Painter That Became a Powerhouse: Sean Brett’s Accidental Empire 1:42:35

3M ago1:42:35

1:42:35

In this powerful episode of The Entrepreneur Experiment, Gary Fox meets Sean Brett – the unstoppable founder behind Steeltech Sheds. From painting houses with no experience to dominating Galway’s coal market and eventually building Ireland’s leading steel shed business, Sean shares a rollercoaster entrepreneurial journey packed with grit, hustle, a…

1
EE418 - Mentor Moment: David Jelly on the €150 Billion Sitting Still In Irish Bank Accounts 11:48

3M ago11:48

11:48

In this bite-sized Mentor Moment from Episode 384, David Jelly, founder of Property Bridges, joins Gary Fox to dissect two of Ireland’s biggest challenges: why people aren’t investing — despite sitting on billions in cash — and why startups struggle to retain talent in a post-COVID world. From cultural mindsets to broken incentives, David gets hone…

1
EE417 - Skin in the Game: How Ella & Jo Went from 1 Idea to Selling in 50 Countries 1:54:23

3M ago1:54:23

1:54:23

In this inspiring episode of The Entrepreneur Experiment, Gary Fox sits down with Charlene Flanagan and Niamh Ryan—the powerhouse duo behind Ella & Jo, one of Ireland’s fastest-growing beauty brands. From a single product and two simultaneous pregnancies to a global business stocked in Boots, Dunnes Stores and over 400 pharmacies, their story is an…

1
#442: Alex McClafferty | What Happens When You Can't Outwork the Truth Anymore 1:08:27

3M ago1:08:27

1:08:27

What happens when the business you built no longer protects you from the parts of yourself you've been avoiding? Alex McClafferty co-founded and sold WP Curve to GoDaddy—but it wasn’t until after the exit that he found himself face-to-face with an identity crisis, emotional collapse, and a brutal confrontation with his shadow self. Watch on YouTube…

1
EE416 - Mentor Moment: Barry Napier on Leadership, Accountability & Evolving as a Founder 11:13

3M ago11:13

11:13

In this Mentor Moment from Episode 355 of The Entrepreneur Experiment, Barry Napier shares hard-won wisdom on how founders need to evolve as their companies scale. From letting go of control to building a culture of trust and accountability, Barry reflects on how he went from “hard work and chaos” to leading with clarity and self-awareness. If you'…

1
EE 415 - Inside the €1B+ Business Empire of John Purdy 1:54:35

3M ago1:54:35

1:54:35

In this episode of The Entrepreneur Experiment, Gary Fox sits down with John Purdy, co-founder of Ergo and a seasoned leader who has helped shape the Irish tech landscape over the past three decades. From launching Ergo in 1993 with just a handful of people to scaling it into one of Ireland’s top IT services companies, John shares the highs, the ha…

1
#441: John Rood | What Happens After You Sell the Business? 1:10:08

3M ago1:10:08

1:10:08

What really happens when an entrepreneur sells their business? For John Rood, it was the start of a deeply personal reckoning with identity, purpose, risk, and time. In this episode, we go beyond the typical exit story and talk about what it actually feels like to step away from the company you built—and what comes next when you’re no longer busy, …

1
He's controlling ChatGPT responses 50:56

3M ago50:56

50:56

[00:00:36] Intro: ChatGPT as a traffic driver and Chirag’s early insight [00:01:48] Revenue Numbers and Profitability of Taco [00:02:24] Personal investment strategy and non-AI assets [00:03:36] How Chirag uses AI agents to replace writers and boost efficiency [00:05:42] What makes Taco a true AI-powered agency [00:07:03] Tracking brand rankings in…

1
EE 414 - Building a Global Brand With Millions Watching: Keilidh Cashell's Story 1:42:21

4M ago1:42:21

1:42:21

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Keilidh Cashell — one of Ireland’s most recognisable beauty creators turned entrepreneur and founder of Kash Beauty. With over 2 million followers on TikTok and a loyal global audience, Keilidh opens up about what it really takes to build a brand in the public eye. From creatin…

1
#440: Cash, Risk, and the Real Reason Most Deals Fall Apart with Elliott Holland 1:45:16

4M ago1:45:16

1:45:16

This episode is fire. Elliott Holland is a straight shooter who has seen hundreds of deals from every angle—searcher, investor, operator, and QofE provider. In this conversation, we cut through the noise to talk about what’s really going on in the acquisition market, why most self-funded searchers fail, and how owners can actually position their bu…

1
1440 is a Bootstrapped Giant 49:49

4M ago49:49

49:49

[00:00:00] Quick Montage (Growth, Grit, Vision, Revenue, Meaning of 1440) [00:00:36] Intro: Why 1440 is Different [00:01:48] Revenue Numbers and Profitability [00:02:24] How They Funded Without Venture Capital [00:04:48] How Big Can an Email Newsletter Get? [00:05:15] Why They Ignored Advice to “Go Niche” [00:06:09] 1440’s Thesis: Inch-Deep, Mile-W…

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