A Product Market Fit Show | Startup Podcast for Founders

• The secrets to mastering product-led growth. | Wes Bush, Author of the #1 Bestselling Book on Product-Led Growth

  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 Listen1. 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.KeywordsProduct-Led Growth, PLG Strategies, SaaS Onboarding, Freemium Model, Free Trial Optimization, User Adoption, Customer Success, B2B SaaS Growth, Onboarding Framework, Go-to-Market TacticsTimestamp(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 TrialsSend me a message to let me know what you think!

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• He sold SkipTheDishes for $200M—then grew Neo Financial to a $1B valuation. | Jeff Adamson, Co-Founder of NeoFinancial & SkipTheDishes

  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.KeywordsSkiptheDishes, 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 foundersTimestamps(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 AdviceSend me a message to let me know what you think!

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• How to tell if you have true product-market fit—& what to do if you don't. | Matt Watson, Host of Product Driven

  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 CustomersSend me a message to let me know what you think!

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• He got rejected by 40 VCs & had 6 months of runway—2 years later, he raised $100M from a16z. | Edo Liberty, Founder of Pinecone

  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 itKeywordsAI, 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 foundersTimestamps(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 AdviceSend me a message to let me know what you think!

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• Post-YC, he split with his co-founder—then grew profitably to $2M ARR with just 5 people. | Jon Yoo, Founder of Suger

  Jon Yoo’s startup wasn’t working. He pivoted mid-YC, spent five brutal weeks without signing a single customer, and then—right after raising his seed round—his co-founder left.Most startups die right there. Instead, Jon figured out how to land massive customers like FiveTran and Snowflake. He grew from $500K to $2M ARR in 6 months. Why you should listen:•Navigating a founder breakup – What happens when co-founders split and how to handle it.•The real YC experience – What worked, what didn’t, and how they pivoted mid-program.•Landing major customers – How they got big logos like Snowflake.•Fundraising insights – What really matters to investors at the seed and Series A stages.•Why startups need forcing functions – The tactics that drove fast product development.•How to know if you have product-market fit – The signals John saw at Sugar.•Burn rate discipline – Why they raised millions but barely spent it.Keywordsentrepreneurship, startups, investment banking, Salesforce, Y Combinator, founder dynamics, product market fit, scaling, cloud marketplaces, business strategy, fundraising, startup, YC demo day, customer acquisition, product-market fit, founder dynamics, early stage startup, team building, scaling, challengesTimestamps(00:00:00) Intro(00:07:55) The Origin of Suger(00:13:30) Going All In(00:19:08) The first 10 customers(00:24:20) The Hardest Pain Point(00:30:29) Becoming Profitable(00:37:05) Celebrate The Small Wins(00:39:56) Finding Product Market Fit(00:42:27) A Piece of AdviceSend me a message to let me know what you think!

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