A Product Market Fit Show | Startup Podcast for Founders

Wesley turned a simple AI headshot generator into a $10M ARR, profitable company—in just two years. He was fired from his job, broke in San Francisco, and, after getting rejected by 30 VCs, down to his last few thousand bucks. But Wesley saw a moment: generative AI was taking off, and no one was tackling AI headshots.  Fast-forward two years, and he’s doing $10M in revenue, profitable, with just 10 employees. He shares every bold tactic—bundling random AI packs, hacking Google rankings, landing affiliates, and manually doing customer support until there was no time left. Wes shares insights that every founder should know, including how he navigated intense competition, handled burnout, and maintained growth without a sales team. You’ll walk away with clear, actionable strategies you can apply immediately. If you want a raw, practical take on zero-to-10M product-market fit in the AI era, this one’s unmissable. Why You Should Listen: • How Wes grew Aragon to $10M ARR—without burning any money. • The guerrilla marketing tactics Wes used to turn a $30 idea into millions of revenue. • Why starting early let him outrun lookalike competitors. • How one affiliate blog post drove more than 50% of early sales. • How he managed high early churn in the early days until the product improved. Keywords: AI startups, early-stage growth, product-market fit, AI headshots, founder stories, affiliate marketing, startup tactics, SEO for startups, guerrilla marketing, startup growth strategies (00:01:54) Zero to $10M in Two Years (00:02:34) Exploring Ideas Before AI (00:05:25) Discovering the AI Headshot Opportunity (00:07:37) How Getting Fired Led to a Startup (00:18:31) Doubling Down on Professional Headshots (00:24:11) Early Guerrilla Marketing and Traction (00:27:59) From $2K to $200K a Month (00:32:13) Affiliate Marketing as a Growth Lever (00:43:18) The Moment of True Product Market Fit (00:47:18) Surviving Near-Failure and Burnout Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Mike first raised $30M for a marketplace that never truly had product-market fit. Then he bet only $10K on ButcherBox. A few years later, he's doing $550M in revenue and he's profitable.  The difference is in his first startup he was just catering to investors— in his second one only to customers. If you’re an early founder chasing growth, listen to how Mike ditched vanity metrics, found sustainable traction, and grew ButcherBox past $500M in revenue—with no outside funding. ____ Why You Should Listen 1. Why not raising can often be a powerful forcing function. 2. Why what VCs want is often not the same as what customers want. 3. How to differentiate in what seems like a commoditized market. 4. Why there is no stronger force in startups than true product-market fit. ______ Keywords product market fit, bootstrapping, butcherbox, direct to consumer, CPG subscription, grass fed beef, founder lessons, Kickstarter, food startup, early stage founder _____ (00:00:00) Mastering the VC Game (00:01:45) How I Raised $30M Without Product Market Fit (00:08:21) Why my VC-backed Startup Failed (00:15:34) Growing Revenue but Losing Money (00:28:07) Early Signals of Real Product Market Fit (00:34:59) Solving Supply Chain to Scale ButcherBox (00:39:43) Bootstrapping to $550M (The Power of Constraints) (00:51:18) Product Market Fit from Day One (00:52:42) Why Founders Need a Lifestyle Plan Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Gopi Rangan has invested in 29 early-stage startups from scratch. He shares a simple but powerful approach to picking the right VCs, structuring your pitch (long-term vision + short-term plan + fuzzy mid-term path), and proving you are the sort of founder every pre-seed investor craves.  If you’re raising a pre-seed or seed, Gopi’s tips will make your process faster, more targeted, and a lot less painful. ___ Why You Should Listen 1. The 2-minute test for "real" pre-seed investors – Spot VCs who truly lead early rounds vs. those who waste your time. 2. His 3-step framework for finding your perfect lead – Forget the 100 investor pipeline. Zero in on 10 prospects who’ll actually write a check. 3. How to balance short-term execution with a massive mission – Win over pre-seed VCs by knowing your next 6 months and your 10-year ambition. 4. Why "business acumen" beats everything – Gopi explains how it trumps domain expertise or brand-name credentials. 5. When to be fuzzy, when to be precise – The counterintuitive approach that shows you’re open to customer feedback while still having big vision. ____ Keywords Pre-seed Funding, Early-Stage VC, Business Acumen, Go-to-Market Strategy, Founder–Investor Fit, Strategic Networking, Seed Round Pitch, Warm Introductions, Mission-Driven Startups, Conviction Investing ____ (00:00:00) Why Ruthless Prioritization Wins (00:03:29) Why Investing at Pre-seed is Personal (00:08:36) Investing When There Are Still Typos in the Pitch Deck (00:12:23) Spotting Founders with Exceptional Business Acumen (00:17:21) Great Ideas in the Hands of the Right Founder (00:26:29) The Practical Guide to Raising Your Seed Round Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Cardiologist Jim Min watched too many 50-year-olds die with no heart-attack warning. He co-founded Cleerly to automate detailed coronary scans—no invasive procedures, no endless manual work.  Yet healthcare’s glacial pace, payers, and federal approvals all stand in his way.  Hear how he’s testing AI across thousands of patients, fighting for universal insurance coverage, and coping with near-burnouts. If you’re a founder navigating hyper-regulated markets, Jim’s journey is the blueprint. ____ Why You Should Listen 1. Heart Disease Kills More Than All Cancers Combined – The staggering truth behind silent heart attacks (and why most diagnoses come too late). 2. Jim’s Big Bet on Early Detection – He’s using advanced AI to spot “dangerous plaque” long before a patient gets chest pain or drops dead. 3. A 10–15 Year Fight to Save Lives – The brutal reality of building a medtech startup in a system that moves slower than any other. 4. Surviving a 17-Day Runway – How his mission-focus (and supportive backers) pulled Jim’s startup back from the brink. 5. Why repeated failure drives game-changing breakthroughs ____ Keywords Heart Disease Detection, Medtech Startup, Coronary CT Angiogram, AI in Healthcare, Early Heart Attack Prevention, FDA Approval Process, CPT Code Reimbursement, Plaque Imaging, Cardiovascular Innovation, Clinical Trials ____ (00:00:00) Embracing Failure & Surviving Dark Days (00:01:56) From Cardiologist to Startup Founder (00:03:07) What Most People Don’t Know About Heart Attacks (00:06:39) Using AI & Imaging to Predict Heart Attacks (00:09:19) Why Cleerly Needed to Exist (00:16:34) The Reality of Healthtech (00:20:41) How Cleerly Built its First Product—and Why it Wasn’t an MVP (00:28:33) Raising $225M to Prove a Radical Idea (00:33:57) Finding Product-Market Fit & the Fight Worth Having Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Adam Robinson once struggled with a stagnant email SaaS stuck at $3M ARR, but he kept experimenting until he found how to solve a problem no one else was tackling—and everything changed. Suddenly, buyers were begging for his identity-based marketing tool—so he spun out Retention.com and grew it to $14M+ in annual profit with no outside funding. In this episode, Adam reveals why he ignored “scalable hacks” until his product proved undeniable, the two keys that finally unleashed product-market fit, and how he uses no-friction brand marketing on LinkedIn to sign up thousands of new leads. ____ Why You Should Listen 1. He chose profit over fundraising – Adam shows how ignoring “growth-hack hype” and focusing on real word-of-mouth built a wildly profitable SaaS. 2. Shocking pivot to product-market fit – A failed email tool spun out a game-changing identity product that users demanded. 3. The #1 trap killing early-stage founders – Why “growth hacking” tactics fail without genuine pull, and what to do instead. 4. Bootstrapping to $14M profit – His surprising path from 3M stalled ARR to unstoppable momentum (with a team of only six). 5. LinkedIn brand building done right – How to attract thousands of perfect-fit leads—no spammy sequences required. _____ Keywords Bootstrapped SaaS, Product Market Fit, Email Marketing Growth, Founder Lessons, B2B LinkedIn Strategy, High Profit Margins, Startup Pivot, Word-of-Mouth Marketing, Early-Stage Experimentation Timestamps (00:00:00) Intro (00:01:57) A Bootstrap Story (00:06:33) Why Bootstrapping Often Means You Can't Lose (00:10:36) The downside of raising VC (00:19:53) A Case Study: Constant Contact (00:22:45) Find an Unsolved Porblem (00:32:06) PMF and Word of Mouth (00:46:45) Piece of Advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]