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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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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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Discover how world-class entrepreneurs, elite thinkers, and peak performers master success in business, body, and brain. Every week, I sit down with extraordinary people to explore how they build thriving businesses, maintain peak physical health, and cultivate sharp, resilient minds. Together, we’ll discover the habits, systems, and experiments they use to create their unique formulas for success. Join me as you learn how to build like a founder, train like an athlete, and think like an art ...
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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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The Unofficial Shopify Podcast

Kurt Elster, Paul Reda

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NEW EPISODES EVERY TUESDAY, SUBSCRIBE FOR UNBEATABLE ECOM RECON – Every Tuesday since 2014, host Kurt Elster shares the Shopify success stories that nobody tells you about, straight from the entrepreneurs living it. Subscribe for a raw look at what it really takes to succeed on Shopify.
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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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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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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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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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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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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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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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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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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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show series
 
I know you're out there. The developer who watches their colleagues enthusiastically embrace Claude Code and Cursor, having AI write entire feature sets while you proudly type every semicolon by hand. The founder who sees AI-generated code as a ticking time bomb of bugs and security vulnerabilities. The software entrepreneur who believes that real …
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Balancing the Books for Business Success | Bootstrapped Unicorns | Episode 68 with Dan Roberts of Accurate Bookkeeping Solutions Boost Your Business Success with Expert Bookkeeping Advice from Dan Roberts! 💼📊 🎙️ Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies, hippie capitalist and ow…
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Discover AI & WordPress pros and cons! From automated content creation to security risks - get the complete guide to using AI with WordPress. Our Special Guest This Week Is Matt Medeiros of Gravity Forms & The WP Minute Podcast In this week's show, we delve into the powerful intersection of AI and WordPress, uncovering its advantages and pitfalls. …
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Dealing With Stress as a VC-Backed and Bootstrap Founder Welcome back to “Two Adrians Walk Into a Startup…” In today’s episode, both Adrians - one a VC-backed founder and the other a bootstrapper - speak about the emotional rollercoaster of startup life, with a central focus on stress. What you’ll hear: Morning routines Keeping habits under pressur…
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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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What does it take to grow from one pharmacy to a nationwide network, and redefine what healthcare means along the way? In this Mentor Moment, Oonagh O’Hagan, founder of Meagher’s Pharmacy, shares how curiosity, courage, and a willingness to step outside your comfort zone can spark incredible innovation. 🎙️ Listen to the full conversation in Episode…
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⏱️ Timestamps / Episode Guide 00:00 – Intro 01:12 – Why most companies fail to get ROI from AI 02:06 – The #1 mistake: Using AI for content without strategy 03:00 – Fragmented data = wasted AI potential 04:00 – How Neil’s team fixes that: Find what drives revenue first 05:24 – Real case study: Med spas using AI to win back Google traffic 07:00 – Ho…
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Founder Reality Podcast - Episode [#]: Three Expensive Lessons About Money That Changed How I Think About Wealth I just finished Morgan Housel's "The Art of Spending Money" and it completely changed how I think about wealth. Five years ago when I was broke, his first book "The Psychology of Money" transformed how I thought about earning. Now with t…
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How do you know when it’s the right time to sell your business? The answer might surprise you. Lexi Grant breaks down the three real factors that determine when to sell — and why waiting for perfect market timing could actually cost you. What you'll learn: The surprising truth about market timing, and why it’s overrated How burnout can quietly dest…
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In this episode of The Entrepreneur Experiment, Gary Fox sits down with Dan Murray, co-founder of Heights, the brain health and wellness brand redefining supplements through science and transparency. From building a startup after insomnia and burnout to scaling Heights to over £25 million ARR, Dan’s story is a masterclass in resilience, product int…
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Why Everyone's Chasing the Wrong Thing (And It's Making Them Replaceable) I walked away from a $3-5 million partnership deal two months ago. Not because the numbers were bad, but because something in my gut said "this feels like work." Most founders would call me crazy, but here's what I've learned: the moment you start optimizing for external vali…
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They Got Acquired is back! In this new season, host Lexi Grant shares insider insights every founder should know before selling a business. After years of studying M&A and publishing nearly 300 acquisition stories, Lexi breaks down what really works — and what doesn’t — when it comes to selling your company. What you'll learn this season: How to st…
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We go inside “Tron: Ares” and discuss: Story & Writing, small details, exposition, likeable characters; and other such stuff and things and stuff. “I have love in me the likes of which you can scarcely imagine and rage the likes of which you would not believe. If I cannot satisfy the one, I will indulge the other.“ – Mary Shelley, from Frankenstein…
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When Passion Isn’t Enough: Startup Fails, Mental Plateaus, and Moving On In this episode, the two Adrians - one a VC-backed founder, the other a bootstrap founder - approach the topic of failure. From stories about failed investment pitches and learning new skills, to reflecting on the often lonely and painful process of entrepreneurship, both Adri…
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Why I wrote a 350-page free ebook that goes against everything Silicon Valley teaches about startups. The consulting-first model that works for the 99.95% of founders who will never raise VC - and why the traditional advice is poisoning young entrepreneurs. The brutal reality nobody talks about: Only 0.05% of startups ever raise VC funding (5 out o…
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What's it really like to attend MicroConf? In this episode, Rob Walling and Laura Sprinkle, founder of Rootabl, recap MicroConf Europe 2025 in Istanbul. They discuss the MicroConf vibe, standout talks on AI, affiliate marketing, and SaaS growth, as well as the value of networking and connecting while getting outside the conference room. Topics we c…
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"These tools rely on automation that only catches 30% of issues. And for blind users with screen readers? The overlays often conflict with their assistive tech—making the site harder to use." Bet Hannon runs AccessiCart, an agency that fixes accessibility problems for e-commerce stores—usually right after they've been sued. We talked about why "qui…
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Send us a text Episode 109 Irish Songs & Slievenamon & The Rest of the Story. My Irish Songs Series continues with the song, "The Valley Near Slievenamon". It describes the song's author Charles Kickham and his passion for Irish Indepence and for the Maid of Slievenamon. I then sing the song in a voice made for photography. Support the show…
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How to Follow What Makes You Feel Alive (Even If It Makes No Logical Sense) You’ve probably heard advice like “follow your passion” or “do what lights you up”—but how do you actually do that in practice as a founder? And how do you know when you’re following aliveness vs fear or performance? In this episode, Jesse and Dave dive into the deeper laye…
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In this Mentor Moment from episode 403 of The Entrepreneur Experiment, Aimee Connolly shares the behind-the-scenes story of building Sculpted by Aimee: from 19 months of figuring out formulation, logistics, and packaging on her own, to spray-painting roses gold for her first press drop. She opens up about what it really takes to bring an idea to li…
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Send us a text Episode 108 Irish Songs & "Kevin Barry" & the Rest of the Story. My Irish Songs Series begins with the song, "Kevin Barry". It describes the 18 year Irish patriot who was hanged in 1920 in Dublin, soon giving rise to Irish Independence. I then sing the song in a voice meant for photography. Support the show…
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⏱️ Timestamps / Episode Guide 00:00 – Intro 00:46 – Garry Tan on CaseText, early LLMs, and hallucination risk 04:00 – The first AI breakthroughs in legal tech 08:00 – How vertical SaaS outperforms general AI platforms 11:00 – Avoca & HVAC: beating ServiceTitan with niche AI 13:00 – YC startup growth rates: 10%–20% revenue weekly 17:00 – The “startu…
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Three interconnected insights that fundamentally changed how I run SimpleDirect and ANC. Why finding balance beats going to extremes, measuring the right things determines your destination, and building systems creates compound leverage. Thought #1: Why LinkedIn makes me cringe (and why I was wrong too): LinkedIn is 50% performance theater - fake v…
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A lot of early-stage founders have understood—mostly because more and more people are talking about their early-stage strategies—that you need to validate your ideas. You need to make an effort to figure out if the thing you're planning to do is actually reasonable to attempt. Validation is important and absolutely worth doing prior to building. Th…
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Ever feel stuck as a founder—uncertain about your next move, paralyzed by fear, or second-guessing what you really want? In this episode, Jesse Pujji and Dave Kashen unpack the hidden dynamics behind “stuckness” and how founders can transform it into growth. From reframing “I don’t know” as liberation, to uncovering fear, anger, and desire as power…
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One Hot Take: Designing Timeless Spaces and Crafting More Than Just a Home | Bootstrapped Unicorns Podcast | Episode 67: Tera Smith Link to video podcast episode: https://youtu.be/eW6jx7pCtUs 🎙️ Welcome to the Bootstrapped Unicorns Podcast! Take a dive into the world of entrepreneurship with host Josh Pies, hippie capitalist and owner of C47 Digita…
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From Magic addiction to Margins updates - Sean finally talked to a customer! Andrew tried Claude Code and wasn't impressed, then gets into product ideas around workflows and flexible tables for MetaMonster. Surprise twist: the guys accidentally design a $699 productized service for MetaMonster and close the deal live on the call. Also: type 2 fun, …
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In this episode, we dive deep into what’s working (and what’s definitely not) in Facebook ads right now, from ASC vs ABO to product-market fit, flash sale testing, and why some campaigns randomly tank. It's a real-time look at rebuilding ad strategy during this tumultuous time of year. 📢 Enjoyed the episode? Thanks for listening! Leave a review on …
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In this episode of The Entrepreneur Experiment, Gary Fox sits down with Steve Crosbie, former professional rugby player turned founder of Fad Saoil Saunas — one of the pioneers of Ireland’s sauna movement. After years playing for Leinster, Munster, and Connacht, Steve walked away from his dream rugby career at just 26. The transition from athlete t…
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How To Build a Successful Plugin Business in 2025 With Special Guest Devin Walker of RollBack Pro & Give WP Learn how to build a successful plugin business in 2025 with proven strategies, monetization tips, and market insights. Start your profitable journey today. In this video, we explore the key strategies for establishing a successful plugin bus…
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The 8AM Text That Saved My Company: When to Pivot vs. Sunset" Episode Summary George shares the raw, unfiltered story of almost shutting down SimpleDirect Financing last week - and how an 8am customer text changed everything. This is a deep dive into the emotional rollercoaster of deciding whether to sunset or pivot a product, the difference betwee…
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We clobber Dwayne The Rock Johnson’s “The Smashing Machine” and discuss: Story & Writing, exposition, stakes, finales; and other such stuff and things and stuff. “I’m always asked, ‘What’s the secret to success?’ But there are no secrets. Be humble. Be hungry. And always be the hardest worker in the room.“ – Dwayne Johnson Notes & References: Suppo…
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Wall Street Journal just proved what every founder already knows: AI isn't leveling the playing field - it's making superstars 10x better while average performers fall further behind. You have 18 months before this gap becomes permanent. Story 1: AI is widening the performance gap (not closing it): Wall Street Journal research: AI makes superstars …
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In this episode we’re excited to be talking with Anthony Eden, founder & CEO of DNSimple. For those who haven’t come across it yet, DNSimple is a service that makes managing domains and DNS simple and developer-friendly. Like DNS, DNSimple has been around many years. I first met Anthony years back at Less Conference in Atlanta, around the time DNSi…
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Where’s the best place to publish if you’re starting content from scratch? In this episode, Rob Walling flies solo, answering your questions on marketing and audience building. He covers what to do when your channels stop scaling, where to publish early on, and the "media company first" approach. Episode Sponsor: Are you a non-technical founder wit…
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I spent three days at Smart Marketer Live in Denver, capturing raw conversations with agency owners, brand founders, and Meta reps about what's actually working in 2025. This isn't your typical conference recap. We're talking about Meta's Andromeda update that killed everyone's ad performance over the summer, why TikTok Shop might be a trap, and ho…
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In this Mentor Moment, tech founder Sean Blanchfield, best known for building and scaling Demonware (acquired by Activision, now part of Microsoft), PageFair, and now Jentic, shares his take on the age-old question: are entrepreneurs born or made? From being the “willing geek” in college to helping shape Ireland’s startup ecosystem, Sean reflects o…
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