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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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The Modern Acre

Tim & Tyler Nuss

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The Modern Acre is the podcast for builders in ag who think differently. Tim and Tyler interview the entrepreneurs, farmers and leaders that are innovating the food and agriculture industry. Through conversations with guests and their own unique insights, Tim and Tyler are leading the dialogue on modern agriculture - from their own farm journey to the latest investment trends. Learn more at www.TheModernAcre.com
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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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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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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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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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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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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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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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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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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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Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and wi…
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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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Tim and Tyler talk to Matt Woolf about the ag economy in California specialty crops. Takeaways Post-COVID, nut pricing is stabilizing while vegetable pricing normalizes. USDA estimates can be inaccurate due to abandoned orchards. The Big Shrink report explores the impact of population decline on agriculture. Population growth has historically suppo…
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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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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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Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple to Google—and he’s spotted a pattern that’s about to repeat with ChatGPT. In this conversation, you’ll learn: 1. The 4-step cycle every platform follows (and …
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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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Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he …
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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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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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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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Tim and Tyler talk to Gaji Balakaneshan about building Midwestern BioAg from a legacy inputs retailer to a soil health solution provider. — This episode is presented by American AgCredit. Check them out HERE. — Links Midwestern BioAg - https://midwesternbioag.com Midwestern BioAg on AgList - https://aglist.com/manufacturer/midwestern-bioag-1 AgList…
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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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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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This episode features a compelling showcase of a bootstrapped entrepreneur, Ben, the proprietor of IE Health. He shares his journey from a passionate fitness enthusiast to a successful business owner, emphasizing the significance of strategic decision-making in entrepreneurship. Ben elucidates the challenges he faced while bootstrapping his busines…
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Everyone says you need a co-founder. Y Combinator barely backs solo founders. VCs prefer teams. But what if the conventional wisdom is wrong? I went from 5 co-founders and 14 team members to running two companies with just 5 people total. We almost went bankrupt in 2023. Four co-founders left. Now we're stronger than ever. The controversial truth: …
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Lost a major partnership at 8pm. Pivoted our entire strategy by morning. This is founder reality - not the highlight reel you see on LinkedIn. I'm tired of the founder content circus. VCs who've never run companies teaching startup strategy. Consultants giving entrepreneurship advice who've never taken real risk. It's all startup theater. In this f…
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Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. …
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Today I'll be talking about a successful marketing project within my software business that turned out to be so successful that it spawned a business built on top of that business. This episode of The Bootstraped Founder is sponsored by Paddle.com The blog post: https://thebootstrappedfounder.com/the-podscan-ideas-vault-engineering-as-marketing/ Th…
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Emotions Are Not the Enemy: Unlocking Leadership, Clarity & Decision-Making Through Feeling ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Most entrepreneurs think their emotions get in the way. But what if they’re actua…
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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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In this episode of The Entrepreneur Experiment, Gary Fox sits down with Áine Kerr, the award-winning journalist, serial entrepreneur behind startups including Storyful (acquired by News Corp), and Kinzen (acquired by Spotify). From teaching in Dublin classrooms to building Storyful alongside Mark Little, leading global journalism partnerships at Fa…
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While VC news often dominates the headlines, more often than not, the VC route isn’t the best fit for a business. So, what do you do if venture capital isn’t the right path for your start-up? In today’s Making The Grade episode, we’re unpacking the evolving world of start-up funding and why VC might not be the best fit for every founder or business…
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This podcast episode presents a compelling showcase of Jack Allweil, a bootstrapped entrepreneur who divulges the intricacies of his journey toward financial independence through real estate investment. Central to his narrative is the significance of leveraging creative financing methods, which enabled him to acquire properties with minimal initial…
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Nick Groeneveld is a designer and User Experience expert who has been a valued collaborator on Podscan, my own software product. Nick works as a freelancer for a lot of companies that have no in-house design knowledge, and he's been navigating the rapid changes that AI tools like Lovable and vZero are bringing to the design world. With 10 years of …
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AI Builders Club – Club Meeting Minutes | Ep. 6: Brand Awareness, Upgraded Topic: What if AI could tap you on the shoulder the moment your brand’s reputation changes? Meeting Agenda: Stay ahead of brand chatter This week, Chase and Aaron dig into the moments you wish you’d caught sooner—when a happy user gives you props on Reddit, when your feature…
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