A Product Market Fit Show | Startup Podcast for Founders

We break down the real startup playbook: fake users, fake traction, real secondaries. From starting a company with zero customers, to raising millions and launching a VC fund that's built to lose money, Jack shares the blueprint for getting rich (without working hard).  Forget chasing product-market fit.  Start chasing growth, money, and, most of all, hype. Why You Should Listen * Why you need to spend most of your time fundraising. * Learn exactly how to fake traction, drive FOMO and raise millions-- even with a terrible product. * Get Jack's ultimate playbook for quitting early and winning big (without working hard) * How secondaries can make you rich BEFORE your startup fails. * Why League of Legends is the key to startup success Keywords startup fundraising, pivot strategy, early stage VC, founder mistakes, product market fit, startup advice, venture capital, startup growth, entrepreneur mindset, founder stories (00:00:00) Intro: Why Quitters Win and Fundraising Beats Traction (00:02:54) Ex-Googlers Can’t Hack It as Founders (00:03:12) Raising Money is Your Only Job (00:10:49) How to Fake User Growth & Create FOMO (00:14:18) Quit Fast, Pivot Faster (00:15:28) Jabroni Capital: The World’s Worst VC Fund (00:26:26) Hiring Hacks: How to Convince People to Join Your Startup (00:28:27) Adam Neumann: Hero or Villain? (00:38:16) The Real Jack Kuveke: Satire, Startups, and Why VC is Broken Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Wes Bush wrote the original bestseller on Product-Led Growth—and then watched everyone try to copy Dropbox and Slack without truly getting it. Now, he’s here to break down exactly what goes wrong when early-stage founders jump into PLG, how to spot your product’s “million-dollar free problem,” and how to fix the three biggest onboarding gaps that sabotage new users. He’ll show you why some sales-led companies die when they try freemium, how to carve out a simpler “first strike” moment, and the reason you need bumpers (like an onboarding checklist) to guide people to success. If you’re still using the “Request a Demo” button, this episode could totally transform your approach and give you a self-serve funnel that scales faster than any sales deck ever could. Why You Should Listen 1. Make Users “Smell the Cologne” – Learn Wes’s approach for letting users experience the core value before they buy. 2. Turning Complex Setups into a No-Brainer – How to map out product, skill, and knowledge gaps so anyone can get started. 3. Bowling Alley Onboarding – A framework to slash unnecessary steps, guide users to that “aha” moment, and cut churn. 4. Freemium vs. Free Trial vs. Reverse Trial – How to pick the perfect model for your startup. 5. Sales-Led to Product-Led – Why some founders fight this shift, and how to pull it off without blowing up your funnel. Keywords Product-Led Growth, PLG Strategies, SaaS Onboarding, Freemium Model, Free Trial Optimization, User Adoption, Customer Success, B2B SaaS Growth, Onboarding Framework, Go-to-Market Tactics Timestamp (00:00:00) Intro (00:01:27) What is Product Led Growth (00:04:37) When to use PLG (00:18:20) Why Simplicity is the key (00:20:15) Wes's Favorite Case Study (00:25:42) The Bowling Alley Framework for Onboarding (00:31:02) Free Trials Must Have Progression (00:36:28) Finding Those Ideal Limits on your Trials Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Jeff Adamson co-founded SkipTheDishes, scaled it to 80% market share, and sold it for $200M—all before Uber Eats and DoorDash even got serious about Canada. He started with zero tech experience, got doors slammed in his face by restaurant owners, and had to personally place orders just to keep early partners engaged. Then, when Uber Eats launched in Toronto, backed by billions in funding, he thought it was over. Instead, Skip became Canada’s dominant food delivery platform and got acquired for $200M. Then Jeff did something even crazier—he decided to take on the banks. With Neo Financial, he’s tackling Canada’s most entrenched industry, building a modern, full-stack digital bank from scratch. He's raised $100s of millions at a $1B valuation. Why you should listen: * How bootstrapped SkipTheDishes took on $10B UberEats  * How to build a three-sided marketplace. * Why building trust with customers is key to long-term success. * Why beginnings are always messy and more about grit than perfection. * Why Jeff didn't stop after exiting for $200M. Keywords SkiptheDishes, Neo Financial, entrepreneurship, delivery service, startup journey, market competition, founding team, restaurant industry, business growth, feedback loop, three-sided marketplace, startup journey, Canadian startups, entrepreneurship, financial services, exit strategy, partnerships, growth strategies, advice for founders Timestamps (00:00:00) Intro (00:02:00) Gotta Have Thick Skin (00:03:54) Skip's Origin Story (00:07:18) Competing with Uber (00:16:09) The First Few Restaurants (00:22:45) Initial Demand (00:26:28) Three-Sided Marketplace (00:38:38) The Original Mission (00:52:10) The First Year at Neo (00:58:40) Product Market Fit (00:59:55) A Piece of Advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

One of the most common questions I get is 'How do I know if I have product market fit?" Especially when you're in that gray zone where things are kind of working but they're not really taking off yet, how do you know if you have product-market fit or not? That's exactly what we dive into here.  Why you should listen: * Why demo to close is an excellent leading indicator of PMF. * Why NPS is not as good as Sean Ellis test to measure product-market fit. * Why retention is the best long-term metric, but takes long. * What qualitative signals you'll feel when you have true PMF. * What to do if you realize you don't have real product-market fit. This podcast originally aired on Matt's podcast called Product Driven, because the topics were so relevant, I figured I'd post it here too. Timestamps (00:00:00) Intro (00:00:55) How do you know if you have PMF (00:06:33) Why some problems are good (00:11:24) Solve a True Top of Mind Pain (00:15:54) Why timing matters (00:21:30) How to Know When to Pivot (00:25:00) Asking the Right Questions to Customers Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Edo Liberty left a high-paying job at AWS—where he was building AI at the highest level—to start Pinecone, a company no one understood. He pitched 40+ VCs, got rejected by every single one, and nearly ran out of money. Then, he flipped the pitch, raised $10M, and built one of the most important infrastructure companies in AI. Then ChatGPT dropped. Suddenly, Pinecone was the must-have database for AI apps, with thousands of developers signing up daily. The company exploded, leading to a $100M round led by Andreessen Horowitz and a 10x revenue surge. If you’re an early-stage founder, this episode is a must-listen. Why you should listen: •How he went from from 40 VC Rejections to a $10M Seed Round • Why he quit a High-Paying Job at AWS to start a Startup • The game-changing shift that made VCs finally “get it” •What really happened inside Pinecone when AI took off •Why most founders misunderstand market timing and what to do about it Keywords AI, Machine Learning, Startups, Entrepreneurship, Vector Databases, Fundraising, SageMaker, AWS, Technology, Innovation, Pinecone, vector database, seed funding, ChatGPT, startup growth, business model, AI, infrastructure, early stage founders Timestamps (00:00:00) Intro (00:07:50) Edo's Story (00:12:27) The Early Days of Machine Learning (00:32:23) Seed Funding (00:42:09) Unsustainable Scaling (00:53:41) Told You So (00:59:24) A Piece of Advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]