A Product Market Fit Show | Startup Podcast for Founders

Corporate spies stealing Slack messages. Adam Neumann raising another $100M (for WeWork 2.0?). AI startups hitting $34B valuations with zero revenue and ordering Ben & Jerry's ice cream over 15 payments with Klarna on DoorDash.  April was wild, and Jack Kuveke joins the show to unpack the chaos, controversy, and insanity behind the biggest startup headlines.  This is different than our normal episodes— definitely a much lighter twist, to be taken with a grain of salt. Let us know what you think! Why You Should Listen * Why Adam Neumann can raise billions—but you can’t raise your seed round * How a $40B valuation for AI startups might not be as insane as it sounds * Why espionage is moving from Wall St to Silicon Valley * What Klarna and DoorDash teaming up says about consumer debt culture * Why A16Z thinks VCs will be the last job standing when AI takes over Keywords Adam Neumann, AI startups, Silicon Valley espionage, A16Z, Klarna DoorDash, startup news, corporate spies, consumer debt, tech valuations, VC funding 00:00 Intro 01:45 Neumann’s new $500 M raise and the WeWork déjà‑vu 08:20 Deel‑vs‑Rippling spy saga uncovered 13:00 11x growth scandal and TechCrunch backlash 18:25 Marc Andreessen says only VCs are irreplaceable 20:38 ChatGPT’s $10 M “please & thank‑you” GPU bill 26:10 Safe Super‑Intelligence and the $34 B pre‑revenue club 30:00 Klarna × DoorDash lets you finance ice cream 37:40 How consumer debt became America’s default setting 41:55 Quick survival guide for founders (and a few rants) Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Forrest Zeisler spent 6 months hearing “no” from every potential customer he spoke to. One year in, Jobber had just three customers—paying $29/month. Today, Jobber generates over $100M ARR, has raised $180M in VC, and employs nearly 1,000 people. In this episode, Forrest shares the brutally honest story behind Jobber’s early days: months of rejection, maxing out credit cards, and nearly quitting. You’ll learn why there are rarely any “silver bullets”, how he handled relentless investor skepticism, and how incremental daily improvements—not crazy inflection points—led to exponential growth.  If you’ve ever wondered whether your startup can make it through the grind, this is a must-listen. Why You Should Listen • Learn how to persist through brutal rejection—Jobber took 6 months to land their first customer. • Understand why chasing “silver bullet” features or channels rarely works. • Find out when it makes sense to keep going despite extremely slow traction. • Hear why your first investors can shape or destroy your startup journey. • Discover why “compound growth” beats chasing short-term inflection points. Keywords product market fit, startup growth, founder stories, fundraising, bootstrapping, Jobber, vertical SaaS, early stage startups, scaling startups, startup rejection (00:00:00) Intro (00:01:55) From Freelance Devs to Startup Founders (00:07:23) Six Months of Rejection (00:15:09) Landing the First Customer and Almost Losing Hope (00:25:39) Brutal Investor Feedback and the $250K Seed Round (00:35:13) Early Growth and Near-Death Experiences (00:44:15) Hitting Customer Milestones and Finding True Product Market Fit (00:48:41) Crossing $100M ARR and Key Lessons Learned (00:51:11) When to Quit and When to Persist Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He turned a personal travel tracker into an app with 10 million users and $10 million in revenue, with almost no funding. He reveals how ignoring conventional startup advice—like launching early, chasing revenue, or partnering for growth—was key to their viral success.  He realized everything growth was about word-of-mouth. So the key to success was obsessing over a single metric: NPS.  If you’re an early-stage founder deciding where to focus, this is your must-listen episode. ___ Why You Should Listen • From losing 90% of users overnight to over $10M in revenue. • Why obsessing over Net Promoter Score (NPS) instead of revenue can drive explosive organic growth. • How to stay hyper-focused on one metric—and avoid distractions. • The truth about partnerships and why most startups shouldn’t chase them. • The counterintuitive decision to build for quality first, even if it delays your launch. ____ Keywords product market fit, startup growth, net promoter score, organic growth, consumer apps, app monetization, viral growth, user retention, travel app, early-stage startup _____ (00:00:00) Losing 90% of Users Overnight (00:01:10) Turning a Personal Project Into a Travel App (00:09:36) Raising $50K and Building Before Launch (00:24:09) Launch Day and First 2000 Users (00:30:35) Why Chasing Partnerships Can Hurt Growth (00:36:40) How Polarsteps Reached $10M Revenue (00:41:00) Surviving COVID as a Travel Startup (00:42:20) Finding True Product Market Fit (00:43:26) The Moment Polarsteps Almost Failed (00:45:03) One Metric Every Founder Should Track Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Jordan Boesch started 7shifts as a teenager helping his dad manage restaurant shifts. Today, his software runs scheduling for 50,000 restaurants. This episode dives into how Jordan bootstrapped early growth, why relentless focus on solving real customer pain mattered more than funding, and how tight partnerships supercharged his expansion.  Jordan also shares hard-won lessons on managing burnout, dealing with near-failure, and creating a company culture that lasts. It’s packed with practical insights every founder needs. ___ Why You Should Listen: • From side project to being used by 1 in 10 restaurant workers in the U.S. • How to use SEO and partnership strategies that drove early growth • Why customer complaints are often a good sign.  • What to do when you're about to run out of cash.  • See why defining clear core values early was key to building a resilient team. _____ (00:00:00) Building for Passion Not Profit (00:01:32) Solving Dad’s Restaurant Problems (00:06:01) Getting the First Real Customer (00:10:47) Taking the Leap to Full-Time Founder (00:13:07) Moving to Silicon Valley and Finding Focus (00:16:51) Growth Hacking with SEO and Partnerships (00:24:59) How to Actually Make Partnerships Work (00:27:08) Building a Big Company Outside the Bay Area (00:30:29) Raising Money and Surviving Near-Failure (00:35:49) Defining Culture to Scale Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

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]