Best Bootstrap Connect Podcasts (2025)

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How M&A Really Works: Buying Companies, Deal Flow & Remote Teams - EXPLAINED 1:01:41

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3d ago1:01:41

1:01:41

What if you could solve almost any business problem… by buying another business? In this episode of Founder to Founder, I sit down with Peter Lang, an M&A expert who scaled through eight acquisitions, built a fully remote global team, and stepped out of the CEO seat — all by mastering deal flow, smart structures, and AI-powered systems. We break do…

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How To Build a Multi-Million HVAC Empire - With No Experience 48:10

13d ago48:10

48:10

What if you could go from immigrant mechanic to CEO of a multi-million dollar home services group — without VC, without burnout, and without wasting years “figuring it out”? In this episode of Founder 2 Founder, I sit down with Victor Rancour(Rocket Holding) — a powerhouse founder who scaled fast through smart acquisitions, ruthless financial disci…

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The Bad Episode 54:41

29d ago54:41

54:41

This episode went a little off the rails towards the end, but not before we cover a lot of ground. It is messy, honest, sometimes awkward, and exactly why we love doing this podcast. We talk about why we refuse to brand Odysi as an “AI consultancy,” even though they we AI every day. We unpack what a product studio really is, how we think about the …

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The M&A Playbook: How to Build $2B+ Without Venture Capital 45:43

1M ago45:43

45:43

Most people chase investors. Tom Shipley built billion-dollar businesses by buying them instead. In this episode of Founder to Founder, I sit down with Tom — serial entrepreneur, Special Forces vet, and founder of multiple $2B+ brands — to break down how acquisitions, not VC, can create generational wealth. From $100 startups to $100M roll-ups, thi…

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He Lost $500M in One Minute — Then Bought 17 Amazon Brands Back 1:02:27

1M ago1:02:27

1:02:27

What happens when your $500M fund collapses on a single Zoom call? Brian Burt, founder of Canopy Management, lived it — and came back stronger. In this episode of Founder to Founder, we talk about scaling an Amazon agency, managing 100+ people with zero micromanagement, and what it really takes to win in e-commerce in 2025. 🔥 You’ll learn: • Why Am…

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Bootstrapping a Tech Agency in the age of AI 1:20:10

2M ago1:20:10

1:20:10

After a busy summer, I Think Tomorrow is back and we are having an informal conversation about what it's like to build a tech agency from the ground up. From working with AI and new technologies to the challenges of selling your own expertise, this conversation digs deep into the emotional and practical realities of bootstrapping, finding your firs…

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The Only 5 Ways to Build & Scale a Home Service Business in 2025 | Scott Slate 1:08:29

4M ago1:08:29

1:08:29

Want to build a $3M+ home service business — even if you're starting from scratch? In this episode of Founder 2 Founder, I sit down with Scott Slate, a 28-year industry veteran who’s helped scale dozens of HVAC, plumbing, and electrical businesses across the U.S. We break down what works right now — from hiring and training, to increasing your comp…

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Why Airbnb Is Dying & Crypto Is the Future — with Jason Lee 48:37

4M ago48:37

48:37

From sleeping in a garage to managing 180 luxury Airbnbs and launching a $100M crypto fund — Jason Lee is living proof that vision, grit, and purpose can build massive wealth. In this episode of Founder 2 Founder, we dive deep into Jason’s journey: scaling in short-term rentals, navigating the collapse of the Airbnb gold rush, and how crypto fund-o…

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No Investors, No Code — Just Grit! How to Build a 7-Figure HVAC Business 1:05:35

4M ago1:05:35

1:05:35

What does it really take to build a home service empire in America — from scratch, no tech skills, no outside money? In this episode of Founder 2 Founder, I sit down with Moe Osman, a former sales pro who bootstrapped his HVAC company using Facebook ads, hustle, and a clear growth strategy. We break down exactly how to start with under $3K, make hi…

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He Cleaned Toilets at 16 — Now Owns a $25M Real Estate Empire 1:07:09

5M ago1:07:09

1:07:09

From scrubbing toilets to running medical facilities — this is the unfiltered journey of Jason Santos, a real estate investor and entrepreneur who turned hustle into generational wealth. In this powerful episode of Founder 2 Founder, Jason reveals how he flipped his first house with no experience, raised smart capital, built healthcare facilities, …

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How Jason Hennessey Built an SEO Empire Without a Website 42:03

5M ago42:03

42:03

In this episode of Founder 2 Founder, I sit down with Jason Hennessey, founder of one of the top SEO agencies for law firms — and a master of systems, focus, and growth. He shares how he worked 80+ hour weeks without burning out, the sticky-note method he uses every Sunday, and how he scaled Hennessey Digital before even launching a proper website.…

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TOP AI Tools That Actually Work for SEO in 2025 1:14:09

5M ago1:14:09

1:14:09

Most people are using AI tools the wrong way. In this episode of Founder 2 Founder, I sit down with SEO legend Jason Hennessey to uncover the AI tools that actually boost traffic and increase lead conversion by 20% — and how you can use them to scale your business. 🔥 You’ll learn: • Jason’s top AI-powered SEO tools for 2025 • How to write content t…

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Authorship, Creativity, and the Future of Work in the Age of AI 1:16:49

6M ago1:16:49

1:16:49

In this episode we, Thomas and Mike explore how generative AI is reshaping the way we think, create, and understand ourselves. Starting with a quote from Ted Chiang (“ChatGPT is a blurry JPEG of the internet”), we unpack what it means to be an author when machines can generate stories, music, and ideas that surprise even their human collaborators. …

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Sweat Equity, Startups & the £75 That Changed Everything 34:16

6M ago34:16

34:16

Guest: Colin Glass – Entrepreneur, investor, accountant, and mentor to hundreds of startups 🔥 He Turned £75 into a Startup Empire: How Colin Glass Helped Build & Back Hundreds of Businesses What does it really take to build a successful startup—and back the next generation of founders? In this powerful episode of The Launch Podcast, we sit down wit…

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Boost Drinks Founder Simon Gray Spills All on £70 Million Exit 53:54

6M ago53:54

53:54

How did a rejected uni student with a 20% attendance rate turn a simple idea into a £70 MILLION brand? 👀 In this explosive episode of The Launch Podcast, we dive deep with Simon Gray, founder of Boost Drinks, on how he built a household brand from scratch—without owning a factory, warehouse, or even delivery vans. Simon shares how: 💡 He spotted a g…

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The Search for Intelligence: AI, Consciousness, and What Makes Us Human 1:28:46

6M ago1:28:46

1:28:46

In this episode, Mike gets interviewed by his good friend and business partner, Thomas Trincado, to explore some of the deepest questions AI is forcing us to ask. What is intelligence? Can machines be conscious? Does intelligence require a survival instinct? We explore how AI development mirrors and deepens our own search for self-understanding, bl…

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Bootstrapped to Exit: Phil Fraser’s Start up success story 44:36

7M ago44:36

44:36

What happens when you quit accounting, stumble into the internet boom, and accidentally build one of the UK’s first online bingo empires? In this episode of The Launch Podcast, Phil Fraser, founder of the Leeds Business Podcast and online gaming veteran, shares how he went from clueless graduate to digital trailblazer—bootstrapping a business from …

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Prison, Rugby, Redemption: Q & Suaia’s Journey to Save Lives 52:59

7M ago52:59

52:59

In one of our most powerful and emotional episodes yet, we sit down with Q and Suaia's—professional rugby players and founders of the Talk Your Walk Foundation. Their stories are raw, real, and deeply inspiring. From troubled pasts, personal loss, and prison time… to international rugby careers and a mission to transform lives through mental health…

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Behind the Screams: How GrimmFest Built a Horror Empire 35:28

7M ago35:28

35:28

In this episode of The Launch Podcast, we dive into the world of indie horror and genre cinema with Rachel and Simeon Halligan, co-founders of GrimmFest and creators of the upcoming psychological thriller Past Life. From producing their first horror feature to launching one of the UK’s leading genre film festivals, Rachel and Simeon share their jou…

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Rugby to Real Estate: How They Built a Property Empire 50:11

7M ago50:11

50:11

In this inspiring episode of The Launch, we sit down with Joe and Tom—two ex-rugby players from West Yorkshire—who left behind their sports careers to tackle the world of property development. With nothing but grit, hustle, and a shared vision, they went from living off maternity pay and using a broken-down Hyundai as a work van… to sourcing and ma…

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How this former Race Driver is disrupting the track experience world, and bootstrapping a business to generating revenue in 6 weeks 44:50

8M ago44:50

44:50

•⁠ ⁠A racing driver from Barnsley breaking into motorsport with zero connections •⁠ ⁠Track days that are more than just a few laps on an airfield •⁠ ⁠And a business quietly rewriting the rulebook on how to drive productivity. James Merrills has built Raidillon Racing & Race Competitions, both startups; one turning high-performance track days into a…

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Raising investment & replacing frustrating phone systems with Neural Voice ft Jeremy Smith and Harry Finch 48:06

8M ago48:06

48:06

Raising investment, replacing frustrating phone systems and being on hold with AI - Inside Neural Voice’s AI Revolution with Jeremy Smith and Harry Finch In this episode, we chat with Jeremy Smith (CEO) and Harry Finch (Lead Engineer) from Neural Voice, a UK startup building AI that replaces traditional phone systems with smart, human-like conversa…

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Digital Dating: Does Tech Help or Hurt Our Chance at Love? 36:49

8M ago36:49

36:49

Dating apps have revolutionized how we meet, but in doing so, they often short-circuit the vulnerability required for real connection. After going on 25+ dates in one month, I discovered that while apps are great at generating matches, they rarely help us transition to meaningful, in-person relationships—and may even trap us in fantasy connections …

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SaaS, Startups & LinkedIn – Real Talk With Utsav Patel of Supergrow 41:16

9M ago41:16

41:16

Send us a text In this episode of The Startup OG Podcast, host Nikunj Thakkar chats with Utsav Patel, founder of Supergrow.ai, about his journey from college dropout to building a lean, impactful SaaS product helping creators grow on LinkedIn. 🎧 In this episode, we cover: Utsav’s story from Gujarat Technological University to startup life The leap …

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Israel, Palestine, and the Digital Frontlines of Friendship 2:05:23

9M ago2:05:23

2:05:23

In this episode, I sit down with my good friend Elinor to talk about navigating conversations about Israel and Palestine in the wake of October 7th 2023. We recount some difficult discussions, why it’s been so easy to feel misunderstood — or to misunderstand others, and how our backgrounds shape the way we see things. We also get into how tech — es…

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Building a D2C Brand in the Creator Economy | Himanshu Gupta, Co-founder of KREO 45:23

11M ago45:23

45:23

Send us a text How do you build a thriving D2C brand in the competitive creator economy? In this episode, we speak with Himanshu Gupta, Co-founder of KREO, a brand that’s redefining the gaming and content creator accessories market. From high-performance gaming keyboards and ergonomic chairs to professional lighting and audio equipment, KREO is emp…

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Bootstrapping 3 SaaS Startups as a Non-Tech Founder | Ankit Dudhwewala's Journey 45:22

1y ago45:22

45:22

Send us a text How do you build and scale multiple SaaS companies without a tech background? In this episode, we sit down with Ankit Dudhwewala, the co-founder of SoftwareSuggest, CallHippo, and ControlHippo. Ankit shares his journey as a bootstrapped, non-tech founder who built not one but three successful SaaS businesses from Ahmedabad. He opens …

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Solving Cross-Border Payments: Rishabh Goel on Merchant of Records with Dodo Payments 50:05

1y ago50:05

50:05

Send us a text Join us for an insightful conversation with Rishabh Goel, Co-founder of Dodo Payments, as we dive into the world of cross-border payments and the emerging role of Merchant of Records in simplifying global transactions. 🌍 In this episode, Rishabh takes us through his incredible journey—from studying at BITS Pilani and London Business …

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Remembering My Brother: Traumatic Loss, Grief, and AI 1:53:22

1y ago1:53:22

1:53:22

In this first episode, I explore a deeply personal topic—the sudden death of my brother Christopher in 2023 at just 27 years old. Joined by my surviving brother James, we reflect on Chris’s life, our grief, and the strange dissonance of losing someone so young. We end by exploring whether AI could—or should—play a role in preserving and even recrea…

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Bootstrapping, Pivoting, and Going Global: The Story Behind Dyrect with Abhishek Agarwal 36:51

1y ago36:51

36:51

Send us a text Join us as we sit down with Abhishek Agarwal, Co-founder of Dyrect, a cutting-edge warranty management platform for modern brands. In this episode, Abhishek shares: His journey of building a startup from Pune The realities of bootstrapping and multiple startup attempts The importance of pivoting to find product-market fit How Dyrect …

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Building & Selling an EdTech Startup: Raj Kothari’s Journey from MyClassCampus to Teachmint 45:33

1y ago45:33

45:33

Send us a text Join us in this episode as we talk with Raj Kothari, Co-founder of MyClassCampus, who shares his journey of building one of India’s largest EdTech startups. Raj dives into how he scaled MyClassCampus into a leading school ERP system and discusses the strategies that led to its successful acquisition by Teachmint. Learn key insights i…

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The Ultimate Product Hunt Launch Playbook: Superjoin's Success Story Revealed 43:00

1+ y ago43:00

43:00

Send us a text 🚀 Want to dominate Product Hunt? Discover the step-by-step strategy that helped Superjoin achieve a #1 Product of the Day, #2 Product of the Week, and rank as the #1 Productivity, Artificial Intelligence, and SaaS product of the week! In this exclusive interview, the Superjoin team breaks down their Product Hunt launch playbook, shar…

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How Shyamal Parikh Built SmartTask: Insights on SaaS, Funding, and Entrepreneurship 49:41

1+ y ago49:41

49:41

Send us a text In this episode of Entrepreneur's Cafe, we chat with Shyamal Parikh, Founder of SmartTask, an online productivity tool designed to help organizations streamline their workflows. Shyamal shares his entrepreneurial journey, including raising pre-seed funding and building SmartTask in a highly competitive SaaS market. We explore the cha…

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SmartCue's Journey & How Interactive Demos Can Skyrocket Your Sales | With Robin Singhvi 39:39

2y ago39:39

39:39

Send us a text Join us for an exhilarating new episode of the Entrepreneur's Cafe Podcast featuring Robin Singhvi, the innovative Founder of SmartCue. In this episode, we delve into Robin's entrepreneurial journey, exploring the genesis of SmartCue and the vision behind it. Discover how SmartCue is revolutionizing the way businesses engage with the…

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Xobin's CEO Guruprakash Sivabalan on Pivoting, VC Funding, and Building $500K ARR Business 55:57

2y ago55:57

55:57

Send us a text Join us for an insightful episode of the Entrepreneurs Cafe Podcast as we dive deep into the remarkable journey of Guruprakash Sivabalan, the Founder and CEO of Xobin—a smart talent assessment platform that's taking the hiring world by storm. In this episode, Guruprakash shares the story of Xobin's evolution, from its early pivots to…

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An Indie Hacker's Journey to $4.5K MRR and beyond | Ft. Sai Krishna, Founder, Superblog.ai 44:30

2y ago44:30

44:30

Send us a text Join us in this enlightening episode as we delve into the world of SaaS with Sai Krishna, the indie hacker and brain behind Superblog.ai. Discover how he propelled his platform to an impressive $4.5K MRR and beyond, overcoming the unique challenges of solo entrepreneurship. Dive deep into Sai's journey, from his early days as an indi…

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Ola Doudin (BitOasis) - How her rebellious childhood caused her to get kicked out of school, why fringe online forums were her entry into the crypto world, and her journey to becoming the first regulated ... 1:05:48

3y ago1:05:48

1:05:48

In this episode, we chat with Ola Doudin, Founder of BitOasis, the largest and most trusted cryptocurrency platform in the MENA region. Formed in 2015, BitOasis serves as the go-to platform for first-time cryptocurrency buyers and seasoned traders alike. They are a pioneer of the cryptocurrency movement in the region. How BitOasis came to be was un…

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Rami Salman (Wrappup, Cisco) - Why his Lebanese roots impact him to this day, how he is able to make something out of nothing, what prompted the Voicea acquisition, and how he overcame countless failures ... 1:07:34

3y ago1:07:34

1:07:34

In this episode, we talk with Rami Salman, the Co-Founder of Wrappup, a meeting-based productivity app with intelligent voice recording that helps inside sales managers make better decisions. Now, Rami is the Director of M&A, Strategy, & Partnerships at Cisco, after Wrappup's acquisition by Voicea, and concurrently by Cisco. This was an in-depth co…

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Sonia Weymuller (VentureSouq) - How VentureSouq came to be, why she describes herself as an accidental outlier in everything, and what her own philosophy of impact investing is 54:15

3y ago54:15

54:15

In this episode, we're having a chat with Sonia Weymuller, Co-Founder and General Partner of VentureSouq (VSQ), a GCC-based Venture Capital firm. Launched in 2013, VSQ is active in the MENA region with a global portfolio of 200+ companies, as well as developing rich educational content around venture investing. Sonia is the most conscious investor …

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Kamal Reggad (RemotePass) - Why his father starting a company at 48 left a lasting impact, how different the initial MVP looked to RemotePass now, and why Kamal still runs onboarding for clients to this ... 47:09

3y ago47:09

47:09

In this episode, we talk with Kamal Reggad, the CEO of RemotePass, a specialised remote work platform making it easy to hire, offer benefits, onboard, manage & pay your global team all at once. Kamal gives us an overview of his entrepreneurial journey: from taking a risk by diving into Morocco's e-commerce ecosystem, to his hardest lessons as a sol…

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Ben Mouflard (Chatfood) - How his first business was selling golf balls at 7 years old, why he was working on idea #20 before reaching PMF, how he met his cofounder, and why they chose to bootstrap Chatfood ... 48:08

3y ago48:08

48:08

In this episode, we’ll have a chat with Benjamin Mouflard, Co-Founder and CEO of the Dubai startup ChatFood. In 2018, Ben and his co-founder Vinny launched ChatFood, a technology platform designed to help restaurants drive their online orders from a centralised system. ChatFood has since empowered 6,000 local businesses across 62 countries to grow …

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Talal Bayaa (Bayzat) - Growing up in Dubai when it had dial-up internet, why he rejected Amir’s initial investment offer, what it’s like to expand across MENA, and how Bayzat went from 3 employees to now ... 44:33

3y ago44:33

44:33

In this episode, Talal Bayaa talked about his journey as a health-tech entrepreneur and founder of Bayzat, A company that provides a free platform for employee benefits, human resources, payroll and more. From finding the right investor to support the business plan, identifying the right talent to hire and grow the company, to even learning how Tal…

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Sapna Chadha on building tenacity, dealing with imposter syndrome, authentic storytelling, organisational influence, doing transformational work [#25] 1:27:27

3+ y ago1:27:27

1:27:27

"Life is not about waiting for the storm to pass, it is about learning to dance in the rain". Sapna Chadha is a dear friend and the VP of Marketing for India and SEA at Google. She is a force of nature, and there's a lot to learn from her career journey. Her early years of learning from her inspiring mother, her experience dealing with imposter syn…

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Manan Khurma on mathematical thinking, aristocratic tutoring, seeking mastery, creating a 'math learning' company [#24] 1:07:09

3+ y ago1:07:09

1:07:09

Manan Khurma is the founder of Cuemath (www.cuemath.com), a leading math learning platform. He is a passionate educator, entrepreneur and a deep believer in making 'mathematical thinking' accessible and enjoyable to every child. My inner geek enjoyed this conversation and we explored many questions about math tutoring and enabling children to aim f…

4y ago53:02

53:02

A very different guest this time, from the world of philosophy, spirituality and service. Nipun Mehta is the founder of ServiceSpace (servicespace.org), a volunteer-driven global organisation that creates lasting change and drives global compassion through small acts of service. Their mission, in their own words, is "to create a shift from consumpt…