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Bassem took Briq from a failed data idea to a Series B leader in construction financial automation.But the path wasn't linear.  In this episode, Bassem reveals how he pivoted to RPA bots, why he killed a high-growth fintech product to survive the 2023 cash crunch, and how he uses a relentless "Go-to-Market" strategy. He breaks down his exact ABM playbook, why he hates trade shows, and why he believes AI orchestration is a bigger shift than the cloud. Why You Should Listen How to identify the "Challenger" who will kill your deal.Why trade shows are a waste of money (and what to do instead).The "1-Person Webinar" hack to close high-value accounts.The brutal reality of cutting 50% of staff to survive.Why selling "risk reduction" beats selling "time saved."Keywords startup podcast, startup podcast for founders, product market fit, account based marketing, construction tech, go to market strategy, enterprise sales, finding pmf, robotic process automation, ai orchestration 00:00:00 Intro 00:06:23 The RPA "Aha" Moment with a Tech Giant 00:11:52 Selling Risk vs. Selling Time Saved 00:13:27 The "New CFO" Signal in Account Based Marketing 00:17:06 Identifying the "Challenger" in Enterprise Sales 00:23:22 The 1-Person Webinar Strategy 00:29:19 Killing the Fintech Product to Survive 2023 00:36:20 Why You Never Truly Have Product Market Fit Send me a message to let me know what you think!

Max went from a YC rejection to building a $1.8B company in less than two years. His company, Legora, is the fastest YC-backed company to become a unicorn in history.  His path to insane growth was not standard: after raising a massive Series A, Max told his board he was pausing all new sales for six months to rebuild the product infrastructure. In this episode, Max breaks down the "burn the boats" mentality that drove their growth, the specific demo tactics that convert 55% of prospects, and how to build an engineering culture that ships fast enough to beat incumbents like Thomson Reuters. Why You Should Listen Why he shut down sales for 6 months immediately after raising $35M.How a single live demo stunt at a conference generated 150 qualified leads.The aggressive pitch strategy that turned a YC rejection into an acceptance.How to close a $10M round with Benchmark after a single meeting.Why you should encourage your enterprise clients to run bake-offs.Keywords startup podcast, startup podcast for founders, product market fit, AI legal tech, Y Combinator, hypergrowth, enterprise sales, Benchmark Capital, fundraising strategy, rapid scaling 00:00:00 Intro 00:06:51 Getting Rejected by Y Combinator 00:15:37 Living on 50k Euros with Design Partners 00:30:19 The Live Demo That Booked 150 Meetings 00:34:06 Raising $10M from Benchmark in 30 Minutes 00:35:13 Shutting Down Sales After Raising Series A 00:46:36 How to Win 85 Percent of Competitive Deals 00:50:05 The Moment of True Product Market Fit Send me a message to let me know what you think!

Russell went from working in private equity to hand-delivering dog food on the NYC subway at 5 a.m. He didn't start with a VC check; he started with a studio apartment kitchen and a belief that dog food was broken. In this episode, Russell breaks down how he turned a side hustle into Spot & Tango, a direct-to-consumer giant doing over $100M in revenue.  He reveals the gritty reality of early-stage CPG, why he vertically integrated his own factory when everyone else outsourced, and how a simple "fresh dry" product innovation called UnKibble unlocked massive scale. Why You Should Listen How to scale from a studio apartment kitchen to $100M+ revenue.How a simple packaging choice created a premium brand identity.Why your second product might become your biggest winner.Why the best performing ad creative is often the cheapest.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, DTC startup, CPG brand, direct to consumer, scaling a startup, founder stories, Spot and Tango 00:00:00 Intro 00:02:30 From Private Equity to Dog Food 00:07:36 Hand-Delivering to the First Customer 00:11:57 The Dark Ages: Cooking in a Shared Kitchen 00:19:17 Pricing Strategy Without Sales Data 00:22:50 The Pink Butcher Paper Brand Identity 00:26:26 Launching UnKibble: The 9-Figure Product 00:31:52 Why Vertical Integration is a Moat 00:40:54 The Best Ad Creative is a Sticky Note 00:47:09 Selling Out Inventory in 4 Days Send me a message to let me know what you think!

Harman went from cold-calling hotels 100 times a day to building the category-defining guest management platform for the hospitality industry. Canary built a $600M company by first solving one tiny, annoying problem: paper credit card authorization forms. In this episode, Harman breaks down how a simple digital form became the wedge into thousands of hotels. He reveals why they stuck with outbound sales long after hitting millions in revenue, the terror of collecting physical checks during the first week of COVID, and the exact moment he knew they had hit product-market fit. Why You Should Listen The "Activated Hair on Fire" framework: How to turn a latent problem into a must-have purchase.Why outbound sales (and cold calling) is often your top early growth channel.How to use a simple, "unscalable" wedge to unlock a massive market.Why you should celebrate the lows: A counterintuitive take on managing founder psychology.The story of signing 200+ customers in a single day (and finding true PMF).Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, vertical saas, outbound sales, cold calling strategies, early stage growth, b2b sales, hospitality tech 00:00:00 Intro 00:02:13 From Management Consulting to Hotel Tech 00:11:32 The Paper Form that Launched a Company 00:17:35 The Activated Hair on Fire Framework 00:24:26 Landing the First Customer via Cold Call 00:28:21 Applying to YC  00:32:35 Making 100 Cold Calls a Day 00:43:42 The COVID Cash Flow Panic 00:48:27 Signing 200 Customers in One Day Send me a message to let me know what you think!

In this episode, Rich breaks down the wild story of Fathom's launch. He reveals how they secured a prime spot on the Zoom Marketplace and generated 100,000 signups in 30 days—only to realize 99.9% of them were useless.  He discusses the pivot to monetization when the market crashed, how to design a product for viral loops, and why staying in private beta for 10 months was the best decision he ever made. Why You Should Listen Why getting 100,000 signups in a single month nearly killed the company.How to use the "Iceberg Strategy" to build a defensible moat.Why you should attack the "800-pound gorilla" incumbent.How to hit $100k ARR by selling a roadmap that doesn't exist yet.The "Visible Feature" mechanic that drives zero-cost viral growth in B2B.Keywords startup podcast, startup podcast for founders, viral growth, product market fit, AI startup, freemium strategy, Zoom marketplace, PLG, B2B sales, Fathom 00:00:00 Intro 00:03:14 Why Sales Reps Hated Gong 00:07:54 Betting on Transcription Costs Going to Zero 00:11:52 The 10 Month Private Beta Strategy 00:17:46 The Zoom Marketplace Launch 00:19:52 100k Signups and Zero Growth 00:26:39 Selling a Roadmap to Hit 100k ARR 00:33:53 The Viral Loop of Visible Bots 00:36:12 Why Enterprise Sales Was a Trap 00:39:51 The Moment of True Product Market Fit Send me a message to let me know what you think!

Bob is a serial entrepreneur who founded MobileIron, grew it to $150M in revenue, and took it public. Now, he's back with his fourth startup, BlueRock, tackling the next massive wave: agentic AI security. In this episode, Bob breaks down the distinct difference between finding Product-Market Fit and finding Go-To-Market Fit—and why confusing the two can kill your company.  He shares the exact questions he asked early customers to pivot from a generic mobile idea to a billion-dollar enterprise solution, the painful transition from founder-led sales to a repeatable playbook, and why he believes agentic AI is the "mobile wave" all over again. Why You Should Listen Why asking "what else is bothering you?" can uncover real pain points.Why finding Product-Market Fit might actually increase your burn rate.Why founder-led sales often fail to scale and what to do about it.How to use a "Deal Grind" session to turn anecdotal sales wins into a scientific Go-To-Market machine.Why identifying the right tech wave matters more than your initial idea.Keywords startup podcast, startup podcast for founders, product market fit, go to market fit, enterprise sales, founder led sales, mobileiron, agentic AI, cybersecurity startup, bob tinker 00:00:00 Intro 00:03:17 Talk to Customers Before Writing Code 00:15:28 Why Finding PMF Can Increase Burn Without Growth 00:17:51 The Founder "Magic Pixie Dust" Trap 00:25:34 The Deal Grind Exercise 00:31:43 From 1M to 80M ARR in 4 Years 00:32:54 Why Agentic AI is the Next Mobile Wave 00:38:30 The Famous Sequoia Tombstone Meeting 00:40:17 The Magic Question: What Else is Bothering You? Send me a message to let me know what you think!

In less than 12 months, Shahar went from an idea to a $30M Series A and a team of 40. He didn't sell another AI tool—he built an AI-first service that replaced expensive human consultants in the massive pen-testing market. In this episode, Shahar breaks down the "Service-as-Software" playbook that allowed him to hit $1M ARR in just three months. He reveals how to convert design partners into paying customers before the product is finished, why he refuses to sell to service providers, and how to achieve a 40% SQL-to-Close rate in the enterprise. Why You Should Listen How to hit $1M ARR in a single quarter with zero marketing spend.Why asking "Would you use this?" is useless and the one question that actually validates demand.Why "Service-as-Software" is the single best business model for AI startupsHow to maintain a 100% win rate against competitors in live bake-offs.The ultimate litmus test for knowing if you have true Product-Market Fit.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, agentic AI, cybersecurity startup, B2B sales strategy, service as software, rapid scaling, Felicis 00:00:00 Intro 00:04:06 Why Manual Pen Testing is Broken 00:15:42 Ideation and The Wallet Test 00:22:38 How to Convert Design Partners to Paid 00:28:05 40 Percent SQL to Close Rate 00:33:14 The Service as Software Business Model 00:46:06 Hitting 1M ARR in One Quarter 00:48:50 Raising a 30M Series A from Felicis 00:50:01 The Turn It Off PMF Test Send me a message to let me know what you think!

Ashwin built a $1.5B company in two years. He didn't do it with a massive team or a complex 5-year roadmap. He did it by ignoring "strategy" and talking to 100+ buyers until he found a problem so painful they would pay six figures for a solution that didn't fully exist yet. In this episode, Ashwin breaks down the exact playbook Decagon used to go from zero to unicorn. He reveals why he refused to hire anyone until $1M ARR, how to differentiate in a crowded AI market, and why your customers are the only roadmap you’ll ever need. Why You Should Listen How to hit $1M ARR in 6 months with just two founders and zero employees.The "Willingness to Pay" test: How to know if a customer will sign a $150k check.Why "over-thinking" your strategy is the fastest way to kill your startup.How to close massive enterprise deals before you have a full product.Why going vertical is often the wrong move for AI startups.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, B2B sales, enterprise sales, AI startup, customer discovery, pricing strategy, early stage growth 00:00:00 Intro 00:02:56 Selling His First AI Startup to Scale 00:09:11 Why Founders Over Intellectualize Strategy 00:13:48 How to Get 100 Customer Interviews 00:15:10 The 150k Willingness to Pay Test 00:21:05 Hitting 1M ARR with Zero Employees 00:25:09 Ignoring Scalability to Win Early Customers 00:31:43 Defensibility in the Gen AI Era 00:39:42 Mocking APIs to Close Enterprise Deals 00:42:58 The Moment of True Product Market Fit Send me a message to let me know what you think!

Jake founded Serval in April 2024— by Dec 2025 he'd raised a $75M Series B from Sequoia at a $1B valuation. He didn't look for a "wedge" or a "niche." He looked at ServiceNow—a $160B, 20+ year-old incumbent that everyone IT team relies on—and rebuilt it from the ground up in a YEAR.  In this episode, Jake reveals the audacity behind building a full-platform replacement from Day 1, why he spent months building in the dark with zero revenue, and how he achieved a 50% demo-to-close rate on six-figure enterprise deals. Why You Should Listen How to go from incorporation to a $1B valuation in just 18 months.The psychological shift in sales calls that proves PMF.How to build a demo so compelling that 50% buy on the spot.Why you no longer need to find a small wedge to win post Gen AI.The specific question that stops customers from giving you generic feedback.Keywords startup podcast, startup podcast for founders, hypergrowth, zero to one, unicorn startup, Sequoia Capital, replacing legacy software, enterprise sales strategy, ServiceNow competitor, Jake Stauch 00:00:00 Intro 00:03:25 Why "Hair on Fire" Problems Matter 00:06:58 Learning What Winning Feels Like at Verkada 00:14:05 100+ Customer Discovery Calls 00:18:12 The One Question That Unlocks Real Pain 00:23:48 Why No-Code Workflows Fail 00:28:45 Taking Risks on AI Model Improvements 00:35:49 From $0 to Six-Figure ACVs in 6 Months 00:39:00 The Strategy to Rip and Replace ServiceNow 00:47:30 The "Rounding Up" Signal of PMF Send me a message to let me know what you think!

Siqi was the CEO of a hot startup doing $20M a year. Then COVID hit. Overnight, revenue went to zero. He had to lay off 95% of his staff. In the chaos of trying to save the company using broken spreadsheets, he found his next big idea: Runway. But the path wasn't a straight line. Siqi spent four years building the product before fully launching.  In this episode, he breaks down why product taste matters more than A/B testing, and the insane viral launch strategy that overwhelmed his sales team and generated $1M ARR in a single month. Why You Should Listen How a viral marketing campaign added $1M ARR in just 30 days.Why "user love" is a trap.Why it took 4 years of building in the dark to create the "Figma for Finance."How to mentally survive losing 95% of your revenue and staff overnight.Why startups are a test of stamina, not intelligence.Keywords startup podcast, startup podcast for founders, product market fit, viral marketing, fintech, financial modeling, finding pmf, startup growth, founder stories, Siqi Chen 00:00:00 Intro 00:04:09 The COVID Crash: From $20M to $0 ARR 00:20:36 The V1 Trap: Great UI, Zero Willingness to Pay 00:36:25 The 4 Year Build: Comparing to Figma and Notion 00:46:53 The Viral Time Locked Jacket Launch 00:53:04 Adding 1M ARR in 30 Days 00:53:45 The PMF Moment Send me a message to let me know what you think!

The startup game has completely changed. If you are still building with the 2018-2022 B2B SaaS playbook, you are already behind.  In this episode, we break down exactly how the GenAI shift has altered value creation, competition, and business models forever. This isn’t just about adding AI to your product—it’s about rethinking your entire reason to exist.  If you want to know where the massive, uncrowded opportunities are right now (and why Service-as-Software is the next gold rush), this is your blueprint. Why You Should Listen Why "incremental value" startups are no longer fundable.The 3 new threats killing your "time-to-market" moat.Why the B2B SaaS playbook is dead and what’s replacing it.The massive "Service-as-Software" opportunity most founders are missing.Moving beyond "per seat" pricing: The new revenue models winning today.Keywords startup podcast, startup podcast for founders, GenAI startups, product market fit, service as software, B2B SaaS, AI business models, startup competition, seed stage, founder advice 00:00:00 Intro  00:01:57 Pre-Gen AI vs Post-Gen AI Eras  00:03:23 The Trap of Incremental Value Props  00:06:58 Gen AI Unlocks Undeniable Value  00:08:50 The New Triple Threat Competition  00:11:50 Why Time in Market Is Dead  00:13:14 Cycle Speed Is the Only Moat Left 00:15:00 Rethinking B2B SaaS Business Models  00:16:45 The Service as Software Opportunity Send me a message to let me know what you think!

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!

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 productThe exact question to ask prospects to validate willingness to payWhy getting to $1M ARR slowly can set you up to scale fasterHow to compete when you're not based in Silicon ValleyWhat talking to your first customer 4x a day for 2 months teaches youKeywords 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!

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!

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!