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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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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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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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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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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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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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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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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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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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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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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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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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Musing with Mo

Monesia Hobbs

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Musing: A deliberate and thoughtful process of examining ideas or situations; a sustained period of contemplation. Insert Mo - Musician whisperer, problem handler, reputation manager, event project, hospitality gal - Join Mo as she explores the complexities of topics ranging from business to motherhood to the music industry and much more. She's bringing some of her favorite thought-leaders along for the ride. Follow @musingwithmo1
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Indie Bites

James McKinven

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Short, bite-sized conversations with indie hackers that have started small, profitable and bootstrapped businesses. You'll learn how they come up with ideas, what they do to validate, find those first customers and make a sustainable income. Episodes every Tuesday.
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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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In this first episode of Musing with Mo, Mo introduces herself by sharing 12 lessons and reflection that she learned as an introvert working in music entertainment. She didn't have a guidebook on how to navigate a world that she is passionate about but called for a different version of herself that she had to find through her years of ups, downs an…
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Today, I’ll share how I’ve been preparing Podscan (and long before that, another SaaS business) to be ready to be acquired at a moment’s notice. This episode of The Bootstraped Founder is sponsored by Paddle.com The blog post: https://thebootstrappedfounder.com/making-your-business-sellable-even-if-you-never-plan-to-sell/ The podcast episode: https…
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It took me a long while to realize this: AI isn't just something like a chatbot for my customers. AI can work behind the scenes to facilitate getting the right stuff in front of the right people for me, even just to figure out who people are and how I should talk to them. And today, I want to share exactly what I'm doing, how expensive this is to r…
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In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work. Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 pre…
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In this episode of The Entrepreneur Experiment, Gary sits down with Alan Andrews, the unapologetically honest founder behind Old Barracks Roastery and Guji Coffee Bar. Known for his bold social content and Ireland’s most controversial coffee shop (no kids allowed, dogs welcome, €15 cups of coffee), Alan lifts the lid on the real cost of starting an…
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Every founder thinks they’re focused on growth. But too often, hidden mistakes in their go-to-market (GTM) strategy quietly erode their chances of success. In this Making The Grade episode, we’re joined by Keji Mustapha, CMO at Partech, to unpack the 5 Silent Killers of Go-To-Market. From undefined ICPs and premature scaling, to misaligned leadersh…
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AI has killed every competitive advantage for software founders except one: distribution. If anyone can build your app in a week, your code isn't your moat - your crowd is. The brutal reality I'm seeing as a software founder since 2019: My first MVP took 8 months to build (April 2019 → January 2020). Today? That same product could be built in a wee…
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How can you scale yourself as a founder? In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Violet, former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yourself to leading managers of managers, they dig into the tough transitions every…
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What Are You Resisting? How Founders Block Growth by Avoiding Emotion ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Show Notes: 00:00 – Intro + recap: resisting emotions, what it means for founders 02:00 – Why emotions …
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This episode presents a compelling showcase of a bootstrapped entrepreneur (Sally Pederson) who elucidates the transformative journey of establishing a business amidst unprecedented societal challenges. Sally recounts how the pandemic catalyzed a pivotal realization regarding the necessity for individuals to explore their options beyond the confine…
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Everyone's telling you to build in public. Share your revenue, your struggles, your team changes. Document everything. I'm calling BS. Most "building in public" is just startup theater with better marketing. Here's why - using my own expensive lessons about what to share, when to share it, and why most founders get transparency completely backwards…
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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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This episode presents a compelling exploration of the transformative potential of LinkedIn, particularly through the lens of artificial intelligence. Al Kushner, a distinguished author and LinkedIn growth strategist, elucidates his journey of bootstrapping a business that empowers professionals to harness the power of this platform. He shares inval…
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I failed at 3 startups before SimpleDirect worked. A ride-sharing app that got destroyed at pitch competitions. A travel planning app that went nowhere. A cashback app that hit #2 on Product Hunt but still died. Each failure taught me more than years of reading startup books ever could. The biggest barrier to founder success isn't lack of knowledge…
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I was reading Brandon Sanderson's latest novel, Wind and Truth, when I came across a sentence that stopped me cold: "A stronger current makes for stronger fish." That's it. That's what entrepreneurship is. We're constantly encountering currents that either facilitate what we want to accomplish—the businesses we want to build, the lives we want to c…
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I fell hard for "vibe coding" - using AI to build apps based on vibes rather than understanding. Spent 6 months with Cursor and Claude, paying $200/month. Built 3 projects. One succeeded, two failed spectacularly. - Project 1 (Success): Rebuilt our dormant mobile app in 2 days using Figma designs and Claude. Looked perfect, worked great, solved a r…
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Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between. In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It…
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Too many startups hire ahead of demand, invest in the wrong leaders, or scale sales without a clear ICP - all mistakes that can cost millions and kill momentum. Today’s Making The Grade guest knows exactly how to avoid those pitfalls. We’re joined by James Bagan, Investor at Frog Capital, Chair and GTM advisor for investors. James has been on both …
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If we could rewind the clock and start our ecom journeys over, what would we actually change? While far from experts, we've both been in the game for several years now, with the battle scars to prove it. In this episode, we dive into what we'd do differently if we could start it all again: from product and marketing choices to financial decisions a…
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Would you take that check again? Two founders. Two paths. One backed by venture capital, the other bootstrapped. This episode breaks down the tradeoffs of startup funding in today’s environment, where open-source tools and cheaper tech stacks have changed the rules. What you’ll hear: How modern stacks cut startup costs VC mentorship vs. hard-earned…
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What are the real risks of AI-generated code and “vibe coding”? In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how integrations can shape early traction. Want to get your questions answered? Drop t…
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I spent 2 years and hundreds of thousands building a sophisticated quant trading firm. Hired 5 engineers. Built complex algorithms. Backtested everything. Result? Couldn't beat the S&P 500. Then I discovered Bogleheads on Reddit. Bought 8-10 simple index funds and household names in May. It's August now. I'm up 5.5% in 3 months doing absolutely not…
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This podcast episode serves as a compelling showcase of the entrepreneurial journey, wherein a seasoned bootstrapped entrepreneur (Lindsey Huettner) shares invaluable insights and strategies pertinent to the art of launching a business with minimal financial resources. The discourse elucidates the importance of maintaining a lean operational model,…
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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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In this Mentor Moment, Gary Fox speaks with Sahil Bloom — investor, writer, and creator — about how his definition of success has transformed. Once focused purely on financial outcomes, Sahil now measures success through time, people, purpose, and health, seeing money as a natural byproduct rather than the goal. He also shares a refreshing take on …
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Weekend rambling thoughts - no script, just real talk. Hit 25,000 Twitter followers this week. Feels surreal because I barely put any time into it. I don't even have Twitter on my phone. Have an extension that blocks it so I don't get addicted. Only check it on desktop once in a while. The weird thing: Sometimes what you don't focus on performs bet…
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This episode serves as a profound exploration of the journey of a bootstrapped entrepreneur, Connor Tyson, who elucidates pivotal strategies that have facilitated his ascent in the realm of personal financial coaching. At the crux of his narrative lies the assertion that the cultivation of genuine client relationships is paramount, as it fosters tr…
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I just said no to $3-5 million. Partnership came in last week. Two years of work for life-changing money. My spreadsheet said yes. My gut said absolutely not. For the first time ever, I listened to my gut. Here's the thing everyone gets wrong: If it consistently feels like work, you're probably doing it wrong. Y Combinator says "do things that don'…
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I think we're at the precipice of a pretty significant change in how we build software products. Obviously, the recent ascent of vibe coding and all the agentic coding tools that we find very useful and highly effective shows a difference in how we approach building products. But there's another change - not just in how we build, but in who these p…
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Too many founders stay in the CEO seat for too long. Often to the detriment of their company, their teams and themselves. It’s not about giving up. It’s about knowing when you are no longer the best person to lead the business into its next chapter. One example of a founder who knew the time was right and made that leap with clarity and intention i…
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In this episode of The Entrepreneur Experiment, Gary Fox sits down with one of Ireland’s most recognisable business voices, Bobby Kerr — founder of Perk, former CEO and Chairman of Insomnia, investor, broadcaster, and champion of Irish enterprise. Bobby shares his remarkable journey from starting his first business at 39 — remortgaging his house wi…
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This podcast episode features an enlightening discussion with Jeremy Smith, the founder and CEO of Neural Voice, who elucidates the pivotal role of voice AI in enhancing the sales process within the B2B sector. Smith articulates how his innovative platform facilitates immediate engagement with potential customers, thereby significantly augmenting c…
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James Phoenix is an expert in agentic coding, particularly Claude code, a tool that I have been using to great effect over the last couple months. I chatted with James just a couple days ago and have implemented several of the tips that he gave me during a conversation, and I'm already almost twice as effective at using this already magically effec…
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San Francisco real estate is back. New York City is back. But the tech community is still obsessed with remote work - "work from anywhere," digital nomad life, "the future is distributed." Here's my controversial take: Remote work might be killing your tech startup. I started my career working remotely in 2018 - before it was cool. Had teammates in…
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AI Builders Club – Club Meeting Minutes | Ep. 7: Goodbye Manual Triage, Hello AI Router Topic: Can AI route every support request to the right human (or bot) without missing a beat? Meeting Agenda: Reroute your support backlog with AI This week, Chase and Aaron answer a universal cry for help—literally. Customer support inboxes are a swamp of passw…
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How do you know it’s time to move on from a product that’s growing? In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting…
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