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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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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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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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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 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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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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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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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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Founder 2 Founder

Sardor Umrdinov

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Welcome to Founder 2 Founder, the ultimate podcast for entrepreneurs who refuse to settle for ordinary. Hosted by Sardor Umrdinov, founder and CEO of Home Alliance - a $100+ million tech-enabled home services platform operating nationwide. From bootstrapping his first business to building a horizontally and vertically integrated empire, Sardor brings you raw, unfiltered conversations with successful entrepreneurs, industry leaders, and game-changers who've turned their visions into multi-mil ...
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Welcome to the AI Builders Club. Yeah, it’s a podcast, but it’s also a workshop, a group chat, and your new favorite corner of the internet if you’re trying to build quality automations with AI. This isn’t a snake oil “prompts that print money” operation. It’s hands-on agentic workflows, pro tips, and real talk from two cofounders in the trenches building a new no-code automation platform. Each week, Aaron Dignan and Chase Adams take on one real-world mess, like inbox chaos, scrambled meetin ...
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Lav Musings

Vladislav Supalov

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Your stream of inspiration about bootstrapping, building a portfolio of assets and making a living as an independent creator on the internet. With your host Vladislav Supalov. Check it out!
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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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Hi, I’m Diane Tarshis — a strategic startup consultant and founder of Startup Distillery, where I partner with entrepreneurs who are experts in what they do, but have never built a business before. Together we dive into the details of their vision so we can dial in their business model and financial roadmap — giving them the clarity and guidance they need to grow and get funded. I’ve spent the last 20-plus years helping entrepreneurs from all walks of life build successful businesses and get ...
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Open Threads

Brian Casel

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Brian Casel hosts conversations with founder friends. We talk about startups, products, software, entrepreneurship, but also what's happening in our lives away from our screens and revenue graphs.
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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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Bowen Gines discusses the hurdles of business. Dive into the strategies and techniques of running and enjoying your business. You will learn from his and other entrepreneur's experiences so that you can build a business that you love. You will learn how to start your business as well as setting up the legal aspects, bootstrapping, taxes, cash flow, sales, marketing, social media, websites, SEO, ranking your Google business listing, building a team, productivity, building your business correc ...
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Backstage Capital is venture investment fund that backs underrepresented tech startup founders. Since inception in September 2015, Backstage has deployed nearly $2m into 40+ startups around the U.S. that are led by women, POC, and LGBT founders. This podcast takes you behind the scenes to show you what it's like to build a fund from scratch and give you deep insights into what investors are REALLY looking for. You'll laugh. You'll cry. You might steal a donut. But that'll have nothing to do ...
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Welcome to the ultimate podcast for exploring *how to make money online*, *build a business on a budget*, and *leverage the best tools and resources* available in the digital marketplace! This show is your guide to understanding a variety of *online income streams*, including *affiliate marketing*, *eCommerce*, *freelancing*, *digital products*, and *passive income generation*. If you’re looking to start a side hustle, grow an entrepreneurial idea, or learn *proven strategies to boost your r ...
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They Got Acquired

They Got Acquired, Alexis Grant

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A show about life-changing business acquisitions and founders who don't follow the Silicon Valley narrative. These stories will inspire you to think differently about how you build your business. And if an exit is in your future, you'll learn practical tips about how to get there. Hosted by Alexis Grant, founder & CEO of They Got Acquired, and produced by Laura Boach.
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Default Alive

Corey Haines & Chris Spags

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Two founders share an unedited look at what it's like to bootstrap a startup through weekly updates. Chris Spags is the founder of Jetboost, a suite of no-code plugins for Webflow. Corey Haines is the founder of Swipe Files, a membership site for marketers built with no-code tools. They chronicle their journeys getting to and staying "default alive": profitable, self-sustaining, with infinite runway.
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In this episode of the Frugalpreneur podcast, host Sarah St. John sits down with Corey Ganim, a self-made entrepreneur who shares his journey of bootstrapping an Amazon-based business from scratch. Corey recalls the pivotal moment that pushed him to pursue entrepreneurship full-time: witnessing a senior manager at IBM frequently missing family time…
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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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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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Clay Adams puts writer Kevin Joseph, the co-creator of the Fantasy Adventure series Tart under the ComixLaunch Pro spotlight. They discuss Kevin's journey from a fourth-grade storyteller to a successful comic book writer, the impact of ComixLaunch courses on his crowdfunding efforts, and the creative process behind his extensive list of projects.…
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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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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 this solo episode of The Entrepreneur Experiment, Gary Fox takes us behind the scenes of the very first Entrepreneur Experiment Retreat — a transformative five-day experience in Marbella, Spain that brought together a select group of founders to focus on their body, brain, and business. Gary shares how a spontaneous idea in 2024 turned into a fu…
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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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Founder or Employee: Why I Chose the Harder Path Two founders. Two paths. One backed by venture capital, the other bootstrapped. This episode is about the personal motivations that drove Adrian and Adrian away from traditional employment and into entrepreneurship, discuss what life might look like if they hadn’t chosen the founder path, and recount…
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Q4 is make-or-break for most brands, but it’s not just about Black Friday. In this episode, Jack and David share how they’re approaching Q4 strategy, from high-level planning and product angles to managing cash flow and staying sane during the chaos. If you're an operator in the trenches, this one’s for you. 📢 Enjoyed the episode? Thanks for listen…
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After 5 years building SimpleDirect Financing from my university dorm to today, I'm shutting it down. This isn't about failure - it's about the brutal lessons every founder needs to learn about attachment, external dependencies, and why starting with principles beats chasing opportunities. The real cost of founder attachment: Spent 5 years attached…
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This special episode was recorded from the Buzzsprout podcast booth on Day 1 of Rails World 2025 in Amsterdam. Our guest, Mariusz Kozieł, is the CEO of Visuality, a Ruby on Rails agency based in Poland. We chat about Mariusz' career progression from developer, to engineering manager, to CTO, and now CEO. We also talk about his and Visuality's effor…
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What if your SaaS isn’t growing because of the product, not the marketing? In this solo adventure episode, Rob Walling unpacks why SaaS marketing feels harder than ever and why most advice out there will waste your time. He shares how he’d approach things if growth has stalled, the questions he’d ask first, and why real progress comes from proven f…
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Why You Resist Feeling Bad (And How It Holds You Back as a Founder) ✅ 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 – Intro + today's topic: “shadows” and the parts we deny 01:30 – Jesse’s shadow: the victim 03:00 –…
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A few years ago I checked my Y Combinator application 20+ times a day. Last month I was obsessively refreshing Twitter analytics every few hours. Then I stopped caring about numbers completely - and everything started working better. The brutal reality of metric obsession: Checked YC application status obsessively after 2021/2022 interviews - made …
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Justin and Jon reconnect after a two-year podcasting hiatus. What's happened since their last episode? Lots! They talk about big changes in their personal lives, and then move on to how they're thinking about Transistor as a business. These discuss burnout and motivation, the evolution of the podcasting industry, the pressure of being a leader, and…
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This Mentor Moment with Mary Sadlier (from Episode 398) dives into why digital is the great equaliser for entrepreneurs. Mary shares the art of getting products on and off shelves, why persistence matters, and the hard truth that nobody’s coming — unless you ask the right questions. A powerful reminder that value creation and resourcefulness win in…
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Why undisclosed acquisition prices should worry you. A bootstrap founder's analysis of the "successful" startup exits that may not be so successful - and why starting over in your thirties isn't a winning strategy. The pattern that's making me worried: Two friends' startups acquired in past two months, five in past two years All labeled "successful…
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I was recently reading an article about The Great British Baking Show - or Bake Off, as we fans of this fun TV competition call it. It was written by someone who had been on the show, one of the competitors, and they were talking about how looking at the show from the inside made them realize something profound: there are no real amateurs anymore. …
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Harris hit $20k MRR. It’s real. What’s next? In this episode of TinySeed Tales, Rob Walling celebrates with Harris Kenny after OutboundSync crosses $20k MRR ahead of schedule. They talk about why hitting a milestone can feel both exciting and overwhelming, the arrival fallacy, and how simple, consistent execution may be all it takes to reach $30k. …
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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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In this episode of The Entrepreneur Experiment, Gary Fox sits down with Paul Buckley — the fiercely honest and deeply reflective founder behind C2O Group. From nearly going pro in golf to blowing his savings in a poker room, to scaling and selling one of Australia’s fastest-growing engineering companies, Paul shares his rollercoaster journey throug…
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Why Silicon Valley VCs giving location advice to founders is complete BS. A technical founder's contrarian take on the "move to SF to maximize luck" myth that's costing bootstrap companies millions. The cringe-worthy VC advice that sparked this rant: Well-known Silicon Valley VC telling founders to "move back to SF" Claims "being successful as a fo…
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B2C, low price point, one-time payments… not the typical recipe for a life-changing exit. In this episode, Rob Walling talks with longtime listener Zamir Khan, founder of VidHug (now Memento). Zamir’s story broke a lot of SaaS “rules”: B2C, low price point, one-time payments, and years of slow growth. He shares how he nearly gave up, the pandemic s…
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