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Bootstrapped Podcasts

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WP-Tonic is a podcast for WordPress professionals, Bootstrap SaaS startup entrepreneurs, and anyone looking to build a business online. We cover a large number of areas with our main show. We interview creative WordPress and startup entrepreneurs, plus online experts who share insights to help you build your online business. Jonathan Denwood and Kurt von Ahnen host and produce the WP-Tonic podcast, which is one of the longest-running WordPress podcasts. Each episode brings you valuable insig ...
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The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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IndieRails

Jess Brown & Jeremy Smith

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Jeremy and Jess interview indie developers who have a passion for the Rails framework and bring their hustle and creativity to building a business. They strive to understand the challenges these developers face and how they are overcoming them to create successful businesses.
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Every week, I sit down with extraordinary founders to explore how they build thriving businesses, maintain peak physical health, and cultivate sharp, resilient minds. This is your journey to learn from the best—world-class entrepreneurs, elite thinkers, and peak performers who have mastered success in business, body, and brain. This isn’t just a podcast; it’s a blueprint for a new kind of founder—one who balances ambition with wellness, hard work with mental fitness, and success with purpose ...
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Startup to Last

Rick Lindquist and Tyler King

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Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.
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Underdog Ecom Podcast

Jack Oswald & David Lindahl

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🚀 Welcome to the Underdog Ecom Podcast—the raw, unfiltered podcast for ecommerce founders actually in the trenches. Tired of the same 9-figure guru success stories? We’re talking real highs, lows, and struggles of running an underdog ecommerce brand—from cash flow crunches to ad meltdowns and everything in between. 🔥 What You’ll Get: - Honest conversations about building a brand without venture capital. - What’s working (and what’s not) in DTC, Amazon, and wholesale. - The latest industry sh ...
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Two Adrians walk into a startup...

Adrian Spataru, Adrian Ispas

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Two entrepreneurs named Adrian with completely different approaches to building companies. One bootstrapped his way to success, the other raised venture capital and navigated the high-growth startup world. Each episode, they share raw, unfiltered conversations about the realities of entrepreneurship from opposite sides of the funding divide. Get insights you won't find anywhere else about what it really takes to build a business.
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Bootstrapped Unicorns: Entrepreneurship with Josh Pies About the Podcast Bootstrapped Unicorns is dedicated to Examining the Journey of Entrepreneurship. Interviews of entrepreneurs – finding out their back story, how they discovered their business, and how they overcame the challenges they faced, will help you – our viewers, friends, and peers – move forward with confidence. Josh Pies (Host), serial entrepreneur and guy who has hit both good and hard times, never gives up. What has fueled h ...
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Founder Reality with George Pu. Real talk from a technical founder building AI-powered businesses in the trenches. No highlight reel, no startup theater – just honest insights from someone who codes, ships, and scales. Every week, George breaks down the messy, unfiltered decisions behind building a bootstrap software company. From saying yes to projects you don't know how to build, to navigating AI hype vs. reality, to the mental models that actually matter for technical founders. Whether yo ...
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Bootstrapped Web

Bootstrapped Web

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Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiting businesses, to growing teams and the emotional rollercoaster that is startup life. It's all here in Brian and Jordan's weekly(ish) updates.
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Bootstrap Marketing

Matteo Micheletti

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Marketing without a huge budget? Bootstrap Marketing is the podcast that helps your business by showing you free tools that are available online! Short and to the point, you can listen to one episode and immediately go and test out these new tools and tips to boost your Business or freelancing knowledge. Support this podcast: https://podcasters.spotify.com/pod/show/bootstrap-marketing/support
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Making The Grade

ScaleWise, Tom Glason

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Less than 1 in 100 Startups manage to achieve funding beyond Series D or an exit. Investors typically expect 8 out of 10 of the businesses they invest in to fail. It’s time to make building a business less depressing and scale more wisely. Tune into Making The Grade to hear first-hand experiences of venture-backed software companies in their journeys from Seed to Series B funding. Every week, we’ll be joined by Founders, Investors and senior Go-To-Market Leaders to explore the factors drivin ...
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The Bootstrap MBA

Jakob Greenfeld

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In this show I document my journey to an independent MBA-type education focussed on building bootstrapped businesses. Over the course of the next 12 month I will try to learn everything I can about ideation, software development, and marketing and then I will apply what I've learned by launching a new product each month.
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Indie Founder

Tiago Ferreira

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My name is Tiago and I am a full time Indie Maker. I build startups without any external investment and my goal is to perfect my entrepreneurial craft and reach $100K ARR (Annual Recurrent Revenue) Join me as I narrate my story and interview other entrepreneurs. Join our community
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Bootstrapped Growth

Bootstrapped Growth

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Welcome to Bootstrapped Growth where you will get actionable, tactical steps you can implement immediately to get results. No latest tips or tactics. No mindset training or feelings. Myself and the guests I bring on are going to share with you the most effective sales, marketing and business skills, strategies, and frameworks so you can repeatedly build a business in any economy.
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Bootstrap Farmer Radio is a podcast that focuses on empowering growers and gardeners with the knowledge and resources they need to be successful, whether they are backyard gardeners, flower farmers, or market farmers. We interview farmers from all walks of life to share their experiences and give helpful tips to growers, no matter where they are in their journey. If you’re just starting your gardening business, an experienced market farmer or home gardener, or growing your first plants in th ...
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The Pestle: In-depth Movie Talk, No Fluff | Film Review | Spoilers

Wes Evans: Actor, Filmmaker, Director, Writer; Todd Sapio: Actor, Producer, Musician, Athlete

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Cinema lovers unite! Two actors and filmmakers decided to cut through all the fluff and start a movie podcast where they actually discuss the film and not a million other things you don’t care about. Covering the obvious (did you like the movie?) while diving a little deeper (what is Interstellar really about? is there a bootstrap paradox?) we are having an in-depth conversation about movies and see if they hold up to scrutiny, and maybe even inform us about life or moviemaking itself. Becau ...
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This podcast will follow my journey as I create https://www.reviewiply.com my latest bootsrapped SaaS. I will keep you updated on everything that goes on. How many customers, how many free trials, what is the MRR? All of the details you could want about my latest SaaS product.
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"Growing Up Poor in Irish Boston” is a podcast series, colored with humor, nostalgia and pathos. It’s about a Boston tenement kid, born in 1939, clawing his way out of poverty by being hard-working, creative, persistent, entrepreneurial and by taking risks often. There are also stories of my later life in Boston, Cambridge and New England. If you like old Boston stories or Irish-American stories or old Cambridge stories, this is your podcast. If you like Pull-Yourself-Up-By-The-Bootstrap typ ...
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Bootstrapped: In The Trenches

Michael Lee Rolland

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We’ve been in the food delivery industry since 2005 and have bootstrapped the entire way. While we compete with VC backed behemoths, this podcast gives listeners an idea about day to day life as an entrepreneur behind closed doors.
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Oliver Cookson is the founder of the world’s number one sports nutrition brand Myprotein®. Starting out in a lock-up garage and an overdraft of just £500, Oliver bootstrapped Myprotein, selling it seven years later to The Hut Group as part of a total exit of around £350,000,000 in a cash and shares deal that saw him become a key shareholder and NED at The Hut Group. In each episode of 'Bootstrap Your Life', Oliver answers business questions sent in from listeners, covering the tools and habi ...
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A couple of years ago, I tweeted that “the best tech stack is the one you already know.” To this day, this is one of my most resonating tweets. People keep bringing it back, and founders who've been around for a while seem to particularly agree with it. But AI changes things. Or does it? This episode of The Bootstraped Founder is sponsored by Paddl…
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Bootstrapped Unicorns Podcast | One Hot Take: Insights on Patent Success | Episode 65 with Dr. Julie Burke Video podcast link: https://youtu.be/Wq8ui5z6Df8 🎙️ Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies, hippie capitalist and owner of C47 Digital Studios, and join the conversation…
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WordPress and Tech Stories of The Month. Get the insights you need now. Discover the month's must-know WordPress and tech stories in our latest video! We explore key updates, fascinating innovations, and expert commentary that are vital for anyone involved in the digital realm. Our engaging discussion keeps you informed and inspired as you navigate…
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While everyone argues about which AI model is best, the smart money is building connectors that work with ALL of them. This week GitHub and Microsoft just made this approach inevitable - and if you're still building custom integrations for every AI tool, you're about to feel very stupid. What is MCP and why the scary name doesn't matter: MCP = Mode…
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I reflect on my recent interview with Craig Hewitt, founder of Castos. I dive into the trade-offs between bootstrapping and raising venture capital. I share my thoughts on how AI is changing entrepreneurship and jobs. I talk about my own experiences with product pivots and tough market challenges. I explain how I use AI to boost efficiency in my st…
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What does it take to build a category-defining SaaS company when your biggest competitors have raised 40x more funding than you? In this episode, Tom Lavery, Founder & CEO of Jiminny, joins us to share how he bootstrapped for years before raising, why staying in control beats chasing hype, and how to layer AI into GTM without over-engineering your …
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What does it really take to make the leap from CMO to CRO and to build a revenue function that actually scales? In the final episode of Season 1, Tom is joined by Florence Broderick, CRO at General Index, to unpack what it actually takes to make the transition to CRO and what founders should know before hiring their first CRO. Florence shares candi…
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In this episode of The Entrepreneur Experiment, Gary Fox sits down with Ciara Troy, founder of Oishii Sushi, to uncover the 19-year journey of building Ireland’s most recognisable sushi brand. From her first Saturday market in Greystones to supplying nationwide through Lidl, Aldi, Tesco, and Spar, Ciara shares the grit, resilience, and fearless nai…
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I have a friend who makes $500K at Google. He's worked there 15 years, made Managing Director, and he told me: "I've basically given up and I'm just collecting my paycheck." This is what happens when you trade freedom for money. The pattern I keep seeing across industries and countries: Waterloo classmate at Microsoft making $250K base - quit becau…
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I speak about the challenges of setting prices for B2C and B2B customers. I share why B2C is more price-sensitive and talk about Podsqueeze’s shift to bigger B2B clients. I give examples from other SaaS companies—how some only show enterprise pricing and others adjust based on value or usage. I talk about Podsqueeze’s new pricing strategy for enter…
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This special episode was recorded from the Buzzsprout podcast booth on Day 2 of Rails World 2025 in Amsterdam. Our guests (and fellow Rails World attendees) are Jesper Christiansen, Olly Headey, and Andreas Wagner. Together we have a roundtable discussion about our wishlist items as independent Rails devs toward the one-person end of the spectrum. …
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We track down Paul Thomas Anderson’s “One Battle After Another” and discuss: Cinematography, tracking shot; Story & Writing, rats, chase sequence; Music adding tone, driving the story; Performances; and other such stuff and things and stuff. “Yes, we do defend our office as we do defend our homes. This is a constitutional right everybody has, and n…
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Three stories from this week reveal something fundamental changing about how you build businesses in 2025. The old VC playbook is dead - here's what's actually working now. Story 1: Founders walking away from traditional VC (and it's strategic, not desperate): Mercury surveyed 1,500 early-stage startups about funding in 2025 66% of founders changed…
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What if you could get all 15 years of this podcast bundled up into one episode? In episode 800, Rob Walling goes solo for a special milestone installment of Startups For the Rest of Us. He covers the 12 foundational commandments that shape his approach to SaaS, hard-won lessons forged from years of building, investing in, and advising startups. Top…
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In this Mentor Moment, Colin Harmon, founder of 3FE Coffee, reveals why consistency beats occasional brilliance when it comes to building lasting brands. He shares the lesson that changed how he thought about coffee forever: customers don’t need the “best cup ever” - they just need it never to be bad. By raising the floor instead of the ceiling, Co…
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What does it take to build, lose, and rebuild as an entrepreneur—while staying true to yourself? In this conversation, host Dave Kashen sits down with Gagan Biyani (co-founder of Udemy, Sprig, and Maven) to explore the emotional and practical realities of entrepreneurship: co-founder dynamics, letting go of team members, navigating failure, and mov…
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As I'm building yet another software service business after having built and sold one back in 2019, I keep wrestling with a fundamental question that might sound simple but has profound implications: What do I actually own in this business? This episode of The Bootstraped Founder is sponsored by Paddle.com The blog post: https://thebootstrappedfoun…
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Bootstrapped Unicorns Podcast | Innovations In Travel and Franchising| Episode 64 with Dawn von Graff 🎙️ Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies, hippie capitalist and owner of C47 Digital Studios, and join the conversations filled with inspiring stories and actionable tips ai…
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Send us a text Episode 100 Southbridge MA Cable TV Promotion of My Podcast Series, "Growing Up, Poor in Irish Boston". September 22, 2025 Cable TV show of Rod Murphy explaining podcasts and podcasting to Southbridge Senior Center folks. The piece de resistance was Episode 12 "Weinstein's Fence" video. Support the show…
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What's next for OutboundSync? In the Season 5 finale of TinySeed Tales, Rob Walling talks with Harris Kenny as OutboundSync blows past $500k ARR. Harris shares the wins and struggles of getting here, from choosing not to raise funding (for now), to planning a laser tag event no committee would approve, to what comes next on the road to $1M. Topics …
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What do you think of when you hear ‘exited Founder’? Someone travelling the world or sitting on a remote island sipping cocktails? Today’s Making The Grade guest may change your perspective… We’re joined by Sean Williams, Co-Founder & CEO of AutogenAI, the AI bid writing software. Before AutogenAI, Sean co-founded Corndell Ltd, which he grew from s…
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In this episode of The Entrepreneur Experiment, Gary Fox sits down with Colin Meagle, serial entrepreneur, venture builder, and founder of Continuous Ventures. Colin has built, scaled, and exited multiple businesses: from creative agencies to international tech ventures, and now operates out of Dubai, where he helps founders and corporates spin up …
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I looked at my calendar this week: zero meetings. Last week: zero meetings. Most founders think this is impossible, but here's what six years taught me - meetings don't make you productive, they make you FEEL productive. The meeting theater that's killing startups: Pre-COVID: Weekly all-hands, daily standups, planning meetings felt "professional" P…
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978 - WP-Tonic Show: We Discuss Local SEO and Speed to Lead in 2025 Master Local SEO and Speed to Lead techniques that convert searchers into customers instantly. Transform your local marketing today. In this show, we dive into the essential elements of Local SEO and its impact on your business's visibility. Discover how optimizing your online pres…
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We trudge through Stephen King’s “The Long Walk” and discuss: Cinematography, constantly bouncing subjects; Story & Writing, themes; Reading books; and other such stuff and things and stuff. “You don’t have to burn books to destroy a culture. Just get people to stop reading them.“ – Ray Bradbury Notes & References: Supports us on our Patreon here! …
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How do you bootstrap a SaaS to $1 million+ ARR? In this episode, Rob Walling chats with Colin Bartlett about how he and his co-founder Andy transformed a side project monitoring tool into a seven-figure ARR business that now serves as an early warning system for outages across 6,000+ services. From nearly abandoning the product during three stagnan…
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For 5 years building SimpleDirect, 45-50% of our blog traffic came from UK, Germany, France, and South America. I turned away all those paying customers because I thought "global" meant "complex." I was dead wrong. Every founder should build globally from day one - it's easier than perfecting a single local market. The "focus" trap that costs milli…
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This week’s Mentor Moment dives into how Nadia Adan built her brand through bold, disruptive content, and why testing, learning, and finding a repeatable format is the secret to scaling on social media. Michael Corcoran shares why standing out often means doing the opposite of everyone else, and how brand storytelling, even with its raw ups and dow…
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Ever find yourself stuck in a cycle of self-discipline, shame, and yo-yo habits? In this episode of Heart of Entrepreneurship, Jesse and Dave dive deep into the psychology behind personal growth—and why punishing yourself into change doesn’t actually work. From fitness routines to leadership patterns, they explore how to unlock lasting behavior cha…
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A year ago I ordered takeout daily, couldn't speak French, and avoided the gym. Today I cook my own meals, read French business newspapers, and work out every day. The secret wasn't willpower or dramatic changes - it was discovering that learning how to learn is the ultimate founder superpower. The learning misconception that kills progress: We thi…
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This is something I've been wrestling with at Podscan, and I know many of you face the same challenge: you're building a product that could serve two, three, maybe even five different ideal customer profiles. And you're trying to figure out how to keep them all balanced—or whether you should even try. This episode of The Bootstraped Founder is spon…
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Building Baseball Dreams: Insight with Rochester Red Wings GM Dan Mason | Bootstrapped Unicorns Podcast | Episode 63 🎙️ Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies, hippie capitalist and owner of C47 Digital Studios, and join the conversations filled with inspiring stories and act…
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OutboundSync just hit $35k MRR—but the decisions are only getting harder. In this episode of TinySeed Tales, Rob Walling and Harris Kenny dive into the messy middle of SaaS growth, where every opportunity comes with a trade-off. They explore the tension between raising funds you don't need, staying focused when good ideas keep coming, and building …
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In the start-up ecosystem, there are a few truths that never change - scaling is harder than it looks, over-hiring can kill momentum, and knowing when to hand over the CEO reins might be the hardest call of all. In this episode,Ed Barltett, Founder & CEO of Hicomply, unpacks how to successfully scale with a lean team and build a GTM engine that act…
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