Best Bootstrapped Giants Podcasts (2025)

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

7h 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. 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 playbook: banking, inv…

1
The Platform Powering 10,000+ Creators’ Content Success with Hani Mourra 23:17

9h ago23:17

23:17

Hani Mourra is a software entrepreneur and creator of Repurpose.io, a platform that helps content creators save time by automating video publishing across all major social media channels. Top 3 Value Bombs 1. You don’t need a big team or burnout to scale - build systems, leverage automation, and grow with intention. 2. One great feature - like auto…

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

17h ago

—

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
AI in Business: From Chaos to Competence with John Alexander Adam 24:37

1h ago24:37

24:37

John Alexander Adam speaks on AI strategy. He believes the future is AI-native and organisations and individuals who invest in it in a smart, structured way now will lead tomorrow. Top 3 Value Bombs 1. Success isn’t about originality or rigid frameworks - it’s about adaptability and the creative synthesis of proven ideas. 2. Most companies are stil…

1
How to Build a Pinball Empire When Everyone Thinks You’re Crazy with Jack Guarnieri 16:34

1d ago16:34

16:34

Starting out as a 'pinball mechanic' over forty years ago, Jack Guarnieri, better known as Jersey Jack is now in the center of the Pinball Universe bringing fun to millions of people. Top 3 Value Bombs 1. Dreams are blueprints for reality - Jack believes that if he can dream it, he can do it, and he proved that by founding a pinball empire from scr…

1
How Small Businesses Can Think Like a Fortune 100: The Framework to Get Your Product to Market Faster and Leaner with Jim Moran 23:47

2d ago23:47

23:47

Jim Moran helps small businesses get to market and scale like Fortune 100s using his STARTING LINE – STREAMLINE – FINISH LINE framework, built from 20 plus years leading global product launches. Top 3 Value Bombs 1. Your first product success unlocks revenue, confidence, and capital-fueling faster growth and future innovation. 2. Fortune 100 strate…

1
How an Entrepreneur Built a $5M Portfolio Using One Single Investing Technique with Kiana Danial: An EOFire Classic from 2022 29:31

3d ago29:31

29:31

From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Kiana Danial, CEO of Invest Diva, is an award-winning, internationally recognized personal investing an…

1
What Web 3 Will Mean For Your Business and Portfolio with Brad Hart: An EOFire Classic from 2022 38:48

4d ago38:48

38:48

From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Brad Hart is an uber nerd when it comes to Web 3, play to earn gaming, defi, crypto and NFT's. He's a b…

1
How Groove is Disrupting Online Platforms with an All-In-One Revolutionary Solution with Mike Filsame: An EOFire Classic from 2022 30:06

5d ago30:06

30:06

From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Mike Filsaime is the CEO of GrooveDigital, LLC, which is the fastest growing software platform for digi…

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

6d 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
How to Go From 0-200K Subscribers on YouTube FAST with Jonathan Levi 26:20

6d ago26:20

26:20

Jonathan Levi is a serial entrepreneur, author, podcaster, and author. Most recently, Jonathan has been focused on growing a YouTube channel in the 3D Printing niche. Top 3 Value Bombs 1. YouTube success isn’t talent - it’s strategy, learning, and consistency. 2. Niche domination happens when you go deep, not broad - and deliver real value. 3. Dele…

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

8d 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

8d 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
The Surgical Investor: Prescribing Lifestyle Freedom through Real Estate with Vasu Kakarlapudi 24:19

7d ago24:19

24:19

Vasu Kakarlapudi helps physicians achieve holistic wellness and financial freedom, investing alongside them through Apta. With surgical precision and 20 plus years of real estate success, he leads by example beyond medicine. Top 3 Value Bombs 1. Wealth is a percentage, not a number. True wealth is how much of your week you spend doing what you love…

1
$12K Credit Card Gamble that Changed Everything with Paul Tembunde & Joan Ekobena 29:00

8d ago29:00

29:00

Paul Tembunde and Joan Ekobena is a business executive and mindset coach based in the D.C. area. In 2002, he and his wife Joan launched a homecare agency with just a 12,000 dollars loan, growing it into a multi-million dollar business. Now, through Premiere Destiny LLC, they help others unlock their potential, live with purpose, and build a life of…

1
From the Dorm Room to King of Cones with Bryan Gerber 21:37

9d ago21:37

21:37

Bryan Gerber is the founder and CEO of HARA Supply - which produces a billion pre-rolled cones yearly for the cannabis industry - and of Hemper - the largest subscription box of smoking accessories. Top 3 Value Bombs 1. Timing and opportunity can outweigh planning. Being in the right place at the right time played a huge role in Bryan's success. 2.…

1
How a Simple T-Shirt Created a 7-Figure Business with Clay Mosley: An EOFire Classic from 2022 26:04

10d ago26:04

26:04

From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. After job hopping for 10 years, Clay Mosley started a digital marketing agency in 2015. He grew it and …

1
The Basics for How to Retire Young with Crypto with James McMahon: An EOFire Classic from 2022 36:20

13d ago36:20

36:20

From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. James McMahon runs the 'Crypto with James' YouTube channel and the 'Copy my Crypto' membership site, wh…

1
Building a High Growth Brand in CPG with Bryan Freeman: An EOFire Classic from 2022 22:36

12d ago22:36

22:36

From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Bryan Freeman led Real Good Foods from startup in 2017 to IPO in 2021, listing with a 300 dollars plus …

1
Tales from the Corner Office with Stasia Mitchell 19:05

13d ago19:05

19:05

As an advisor to ambitious CEOs, owners, and entrepreneurs, Stasia Mitchell leads EY’s entrepreneurship strategy and the EY Entrepreneur Of The Year™ programs in over 60 countries, with responsibility for the development of long-lasting relationships with our winners, our alumni, their investors, and the whole entrepreneur ecosystem. Top 3 Value Bo…

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

15d 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

15d 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
Monetizing Your Podcast with Heather Osgood 21:00

14d ago21:00

21:00

Heather Osgood founded True Native Media, a podcast representation agency specializing in podcast advertising, and The Podcast Broker, a service that facilitates the buying and selling of entire podcasts. Top 3 Value Bombs 1. Podcasting success comes from action, not over-planning. 2. Think like a content creator, not just a podcaster, to attract s…

1
4X Your Clarity & Productivity to 2X your Revenue & Time Off with David Wood 24:51

16d ago24:51

24:51

David Wood went from Fortune 100 actuary to coaching maverick, he helps entrepreneurs double revenue and happiness - drawing on hard-won lessons from business, burnout, and bold leaps like Hollywood acting and near-death survival. Top 3 Value Bombs 1. Intentionality is your superpower. You can drastically improve your clarity, productivity, and rev…

1
From Suffering to Success with G. Michael Hopf 23:22

17d ago23:22

23:22

G. Michael Hopf is a USA Today bestselling author of forty books, including The New World series which sold over a million copies, a Marine veteran, and co-founder of Beyond The Fray Publishing. Top 3 Value Bombs 1. Suffering is inevitable, but staying stuck is optional. Your response to adversity defines the trajectory of your growth. 2. Reframing…

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

18d ago

—

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
How to Redefine Our Broken Education & Employment System for Good with Siddharth Rajsekar: An EOFire Classic from 2022 43:46

17d ago43:46

43:46

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Sidz is a college drop-out, "musician turned digital geek", a spiritually grounded minimalist, father …

1
Becoming A Hero: How To Transform Into The Best Version of Yourself with Brian Johnson: An EOFire Classic from 2022 21:28

18d ago21:28

21:28

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Brian Johnson, Founder and CEO of Heroic, recently made crowdfunding history and is building a social …

1
Earn More with LinkedIn Sales Navigator with Julbert Abraham: An EOFire Classic from 2022 24:03

19d ago24:03

24:03

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Julbert Abraham is widely known as “The LinkedIn Guy”. He is the author of the book “7 Steps to 7 Figu…

1
Prosper from the Inside Out with Joan Sotkin 23:29

21d ago23:29

23:29

Joan Sotkin helps entrepreneurs rapidly improve their relationship with money and themselves while coping with the current chaos. She started doing business online in 1995 and now hangs out on Substack. Top 3 Value Bombs 1. Financial problems are never about money - they’re emotional patterns rooted in childhood experiences. 2. The five emotions pe…

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

22d 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

22d 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
How to Create Platform-Proof Livestreams That Consistently Generate Leads and Revenue with Tanya Smith 20:27

22d ago20:27

20:27

Tanya Smith, Video Strategist & Business Coach, helps service-based entrepreneurs simplify content marketing, automate workflows, and create platform-proof livestreams and video podcasts that consistently generate leads, clients, and revenue. Top 3 Value Bombs 1. Authentic live streaming builds real-time human connection, trust, and leads - without…

1
Growing a Business with Community with Michael Chernow 22:57

23d ago22:57

22:57

Michael Chernow, Founder and CEO of Kreatures Of Habit is a Cereal Entrepreneur and wellness expert. Chernow launched his first business in 2010 and has been building business for the last 15 years. Top 3 Value Bombs 1. Balance is Possible - Even as a driven entrepreneur, you can craft a work-life balance that brings joy and success. 2. Community W…

1
5X Growth: From 60 Employees to 350+ Employees with Clay Clark and Special Guest Kevin Thomas of www.MultiCleanOK.com 32:01

24d ago32:01

32:01

Clay is the former U.S. SBA Entrepreneur of the Year, founder of 6 multi-million dollar companies, Forbes Contributor, author of 13 books & host of 6-times iTunes chart topping podcast. Special Guest Kevin Thomas Founder of www.MultiCleanOK.com. Top 3 Value Bombs 1. You don’t need a massive team to start - just a proven system. 2. V.I.S.M.D. is the…

1
Expense Management Flipping Sucks, But Fintech Is Revolutionizing The Game with Nate Meadows: An EOFire Classic from 2022 21:47

25d ago21:47

21:47

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Nate Meadows is the Head of Marketing for ClearSpend. He carefully crafts marketing campaigns, voice, …

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

26d 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
How to Generate a Passive Income Through Real Estate Tokenization Through RealT with Remy Jacobson: An EOFire Classic from 2022 22:47

26d ago22:47

22:47

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Remy Jacobson has been the Chief Executive Officer of J Cube Development since 2012. In 2011, Remy tra…

1
How Entrepreneurs Can Build Their Own App without Knowing How to Write a Single Line of Code with Emil Egeland: An EOFire Classic from 2022 29:17

27d ago29:17

29:17

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Emil Egeland is the founder of the software company Yellow Jersey. Prior to Yellow Jersey, Emil founde…

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

28d 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
Scaling with Soul: Conscious Entrepreneurship & Venture Growth with Amish Shah 20:55

28d ago20:55

20:55

Amish Shah is an entrepreneur, investor, and visionary bridging ancient wisdom with modern innovation. He specializes in media, wellness, and technology, empowering businesses through strategic growth, conscious leadership, and venture investments. Top 3 Value Bombs 1. Entrepreneurs are dynamic and can thrive by building multiple synergistic ventur…

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

29d 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
Curating Community for Business and Personal Success with Darren Darnborough 25:16

29d ago25:16

25:16

Darren Darnborough is a British-born Actor working in Hollywood. His TV & Film work includes hit US shows MacGyver, Magnum PI, 2 Broke Girls & True Blood. He is also the Co-Founder and CEO of WeAudition.com - the global video-chat community for auditions, rehearsals, self tapes & advice. Top 3 Value Bombs 1. Curating a community is an art - curate …

1
Scale Effectively, Build Internal Leaders with Hana Ngo 19:21

30d ago19:21

19:21

Hana Ngo is an experienced Executive & High-Performance Team Coach, supporting 300+ global companies and 100+ teams to elevate leadership, boost performance, reduce turnover, and cultivate thriving, resilient, agile teams & leaders. Top 3 Value Bombs 1. Delegate outcomes, not just tasks - true leadership growth happens through thinking transfers. 2…

1
Fail to Win with Colin Campbell 25:02

1M ago25:02

25:02

Colin Campbell is a serial entrepreneur who has co-founded over a dozen multi-million dollar companies. Number 1 Best Selling Award winning Author, speaker, and founder of Startup Club, helping entrepreneurs globally through his book - Start. Scale. Exit. Repeat. Top 3 Value Bombs 1. You can fail 8 out of 10 times and still succeed if you cut loser…

1
Why the Creator Economy Needs a Creator-Focused Event with Joe Pulizzi: An EOFire Classic from 2022 29:26

1M ago29:26

29:26

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Joe Pulizzi is founder of multiple startups, including content creator education site, The Tilt (TILT …

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
Why Every Brand Needs To Be A Content Machine in 2022 with Eric Dyck: An EOFire Classic from 2022 25:14

1M ago25:14

25:14

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Eric Dyck is co-founder of DTC Newsletter and Podcast, where he connects his subscribers to the exact …

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
Why the World Needs You to Make a Lot More Money with Derrick Kinney: An EOFire Classic from 2022 28:38

1M ago28:38

28:38

From the archive - This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Derrick Kinney believes if you’re not making the money you deserve, and you’re not making the impact o…

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