A Product Market Fit Show | Startup Podcast for Founders

He got rejected by 60 VCs, burned all his savings—then grew to $100M ARR & a $2B valuation. | Kyle Hanslovan, Founder of Huntress

For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3. Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel. Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round.  But then things changed: 2018: $1.5M ARR 2019: $5M ARR 2020: $10M ARR 2021: $20M ARR 2022: $40M ARR 2023: $70M ARR 2024: $100M+ ARR Huntress is valued at $2B. The investors who backed his $1M bridge are up 140x.  Now every VC wants to invest—and Kyle's the one saying 'no'. Why you should listen:  How to know whether you should keep going or quit. What it takes to get through the first few years at a bootstrapped startup. Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention). How starting a startup can impact your personal life and relationships. How to work with partners to sell to long tail SMB customers. Keywords entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth Timestamps: (00:00:00) Intro (00:2:01) Working at the NSA (00:6:14) A big win in counter cyber terrorism (00:10:00) What gave way to Huntress (00:14:22) Pitching to a startup accelerator (00:16:29) Adopting curiosity (00:21:04) Getting ahead of cyber criminals (00:26:00) Starting to grow (00:32:50) Cult or conviction (00:35:00) It takes grit (00:39:50) Learning from people's lessons (00:42:20) Cockroaches and underdogs (00:46:10) Three strikes, I'm out (00:52:56) Having a military background (00:56:17) One piece of advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He killed a $100K ARR product & pivoted—then raised $375M. | Viraj Parekh, Co-Founder of Astronomer

They were building a Segment competitor. It was working—customers were paying. But every sales call, prospects kept asking about the backend tech instead of the product.  So they killed the roadmap and pivoted. It took them 18 months to hit $1M ARR. Then they started growing. And so far, they've raised $350M.  Viraj walks through exactly how he validated the pivot, landed the first 10 customers, and why being outside Silicon Valley forced him to show more traction than everyone else. Why You Should Listen * How to know when your side feature is actually your real product * The exact question to ask prospects to validate willingness to pay * Why getting to $1M ARR slowly can set you up to scale faster * How to compete when you're not based in Silicon Valley * What talking to your first customer 4x a day for 2 months teaches you Keywords startup podcast, startup podcast for founders, open source startup, B2B SaaS growth, pivot strategy, developer tools startup, finding product market fit, early stage fundraising, design partners, commercial open source 00:00:00 Intro 00:01:46 Getting caught at the Coldplay concert 00:14:29 Deciding to Pivot From a Working Product to Something New 00:17:27 Building a Business Around Open Source Technology 00:19:38 Selling Before You Build 00:27:37 Talking to the First Customer Four Times a Day 00:30:51 Landing the First Ten Customers 00:35:10 Fundraising Without Silicon Valley Pedigree 00:38:48 When He Knew He Had Product Market Fit Retry Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Solo Episode: The Five Steps to Product Market Fit

For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 2. Here are the key lessons from the past 60 episodes that we've released to date.  Each of the 5 steps to Product Market Fit is based on actual case studies with real examples you can use. It's a recap of everything I've learned over the last two years- you don't want to miss it. Chapters: (00:00:45) Mistakes Are Unavoidable But Avoidable Mistakes Are Unaffordable (00:04:41) 1. Before Startup Mode, There's Research Mode (00:07:16) 2. Only The Insanely Focused Survive (00:10:49) 3. You Have to be IN the Market to WIN the Market (00:14:08) 4. Forget Growth. Find Value. (00:18:05) 5. Pivot Harder & Faster (00:23:50) Recap Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He killed a viral app with 50k users. 2 years later, he hit $10M ARR and raised $30M from Sequoia. | David Paffenholz (Juicebox)

David had a consumer app with 50,000 users and viral traction—and he shut it down. The retention metrics weren't as good as what he'd seen at Snapchat. That difficult decision cleared the path for Juicebox, AI for recruiting that grew to $10M ARR in 2 years.  In this episode, David reveals how he pivoted to AI recruiting, generated millions of views with a simple LinkedIn demo, and ground through months of brutal churn to unlock 10x growth. If you want to know how to execute a flawless PLG strategy, run a hyper-lean team, and secure a $30M Series A from Sequoia, this is the blueprint. Why You Should Listen * Why you should kill some products even if they're going viral. * How to launch a B2B product with zero budget. * The "manual" playbook for fixing high churn. * Why you should keep your team under 25 people even after raising millions. * How to land an inbound term sheet from Sequoia. Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, PLG strategy, viral marketing, pivoting, AI recruiting, Series A fundraising, Sequoia Capital 00:00:00 Intro 00:03:15 Learning Growth at Snap 00:13:01 Killing a Viral App with 50k Users 00:20:34 The 90 Second LinkedIn Video That Launched Juicebox 00:26:21 Fixing High Churn with Manual Work 00:33:04 Why B2B Products Only Need to be Marginally Better 00:42:27 Scaling to $10M ARR with Founder Led Sales 00:47:40 Raising a $30M Series A from Sequoia 00:50:12 The Moment of True Product Market Fit Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Her VCs said she killed the company. 6 years later, it's worth $1.3B. | Jennifer Smith, Founder of Scribe

Jennifer went from VC to founder and immediately broke every rule in the book. When she pivoted Scribe from an automation tool to a documentation platform, her investors told her she had just killed the company. She ignored them.  Instead of polishing her product, she launched a "janky" offline MVP on Product Hunt to test for real market pull. Scribe is now used by 95% of the Fortune 500.  In this episode, Jennifer reveals the brutal truth about ignoring "smart" money, why you should run PLG and Enterprise sales simultaneously from Day 1, and how to tell the difference between pushing a boulder up a hill and chasing one down it. Why You Should Listen * Why you sometimes need to ignore your investors to save your startup. * The "Boulder Test": The definitive gut check for knowing if you have true Product-Market Fit. * How to validate a massive opportunity with zero marketing budget. * Why the conventional wisdom about choosing between PLG and Enterprise Sales is wrong. * How to turn executive hiring interviews into free mentorship sessions. Keywords startup podcast, startup podcast for founders, product market fit, PLG strategies, MVP testing, enterprise sales, go to market strategy, early stage growth, finding pmf, founder stories 00:00:00 Intro  00:02:21 1,200 Customer Interviews as a VC  00:22:07 How to Hire for Excellence  00:30:18 The Pivot from Automation to Documentation  00:39:17 Launching a "Janky" MVP on Product Hunt  00:49:09 The Boulder Test for Product-Market Fit  00:52:50 Doing PLG and Enterprise Sales Simultaneously  01:03:12 Ignoring Investors to Save the Company Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]