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Most investors told Nick not to hire a salesperson before he had product market fit. He hired the top rep in legal tech anyway and called him a product market fit finder. That rep signed a paid five-year deal in his first week, over lunch. By the time Sandstone came out of stealth, they had done hundreds of demos and had $10M+ of pipeline waiting. Sandstone just raised a $30M Series A. In this episode, Nick breaks down why the intros he never asked for were the moment he knew PMF was real, how sitting next to customers and watching them work turned into their biggest integrations, and why they fired design partners whose problems did not match the market. Why You Should Listen Why intros you never asked for are the truest early signal of PMF.How hiring an elite AE pre-PMF bought them a product market fit finder, not a quota.Why saying yes to every design partner request leads you away from the market.How two or three dinners a week convert prospects to demos almost every time.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Sandstone, Nick Fleisher, legal tech, in-house legal teams, AI for legal, contract lifecycle management, enterprise sales, design partners, hiring an AE, founder-led sales, word of mouth referrals Chapters 00:00:00 Intro00:02:14 The Referrals That Proved PMF00:05:36 How to Actually Drive Word of Mouth00:07:15 The Idea Born Inside McKinsey Legal00:11:38 Why Legal Never Got a CRM00:17:07 Quitting and Raising From Sequoia the Same Day00:25:53 The Design Partners They Fired00:30:20 Hiring an AE Before You Have PMF00:40:32 Two Dinners a Week That Fill the Pipeline00:47:03 Go Spend Time With Customers in PersonSend me a message to let me know what you think!

Dan's first app made over $1M in two months. Then Facebook sent a cease and desist and killed it. His next company, Mode Mobile, grew revenue 32,481% in three years and ranked #1 on the Deloitte Fast 500. Then his crypto advertisers went bankrupt, revenue fell from $25M to $8M, and he cut half his staff. No VC wanted a declining Series B. So he raised $5M from his own users in three months—then $75M more. In this episode, Dan breaks down how paying people to use their phone actually makes money, why revenue concentration and not growth is what nearly killed Mode, and how to run a creator-led marketing campaign at $30 a video. Why You Should Listen Why the product market fit that feels insane is often the kind that dies fastest.How building on someone else's API cost him two different companies.Why extending your payback period is the fastest way to run out of cash.How to know within $20K to $30K whether creator-led marketing works for you.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Mode Mobile, Dan Novaes, crowdfunding, Reg A, consumer apps, rewards apps, creator-led marketing, UGC creators, user acquisition, revenue concentration, Android apps Chapters 00:00:00 Intro00:03:09 The App He Built In A Week00:06:38 $1M In Two Months00:08:25 Facebook Shuts It Down00:15:39 The Pivots Before Mode00:20:42 32,481% Growth To The Fast 50000:26:26 Revenue Concentration Nearly Kills It00:31:50 How Paying People To Play Works00:37:53 Creator-Led Growth For $30 A Video00:47:09 What Makes A Crowdfund WorkSend me a message to let me know what you think!

Keith raised a $43M Series B for Tome. The product had 20 million users. But retention was terrible and nobody cared enough to complain. So he turned it off before he knew what he'd build next, went from 70 people to 7, and started over. Lightfield just closed a $47M Series A. In this episode, Keith breaks down how he knew Tome would never grow up, why customers lighting up your Slack at 3am is the signal you actually want, and the exact playbook he used to sell an AI-native CRM to YC founders before he charged them a dollar. Why You Should Listen Why angry customers are a better signal than 20 million happy ones.How to know when optimizing metrics will never re-inflect your business.Why you have to kill the old product before you can find the new one.How to win founders with free software and events instead of cold email.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Lightfield, Keith Peiris, Tome, pivoting a startup, AI native CRM, agentic system of record, cutting burn, go-to-market, selling to YC founders, launch videos, B2B SaaS Chapters 00:00:00 Intro00:02:27 The Customers Who Were Hopping Mad00:07:41 20M Users, Almost No Retention00:09:27 When Your Business Works But Won't Inflect00:11:24 Why His Board Said Burn the Boats00:18:29 Turning Off the Product Before Knowing What's Next00:22:13 Reinventing the System of Record00:30:25 How to Sell to YC Founders00:36:04 Making a Launch Video Hit a Million Views00:44:08 The One Piece of AdviceSend me a message to let me know what you think!

Aaron started Vestwell in 2016. Two years in, he had $500K in ARR and an investor asking if it would ever make money. During the 2021 bull market, VCs told him 401ks were too boring—they were busy chasing crypto. Then Morgan Stanley signed. Today Vestwell has 2.5 million people saving on the platform, over $200M in ARR, and just raised $385M at a $2B valuation. In this episode, Aaron breaks down why he white-labeled everything instead of building his own brand, how losing the JP Morgan bid as a 40-person startup still turned into one of his largest partnerships, and how a methodical cap table let him raise a Series A on a couple hundred thousand in revenue. Why You Should Listen Why letting your customers keep their brand beats competing with them.How to raise a Series A with only a few hundred thousand in ARR.Why losing an enterprise deal is the start of the sale, not the end.Why you never regret firing someone too soon.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Vestwell, Aaron Schumm, fintech, 401k, retirement savings, enterprise sales, channel partnerships, white label software, Series A fundraising, Morgan Stanley Chapters 00:00:00 Intro00:02:05 The Morgan Stanley Deal That Proved PMF00:08:32 A 401k So Bad It Started a Company00:10:23 Building V1 in a Regulated Industry00:17:07 Turning Advisors Into a Sales Channel00:23:57 Raising an A on $200K of Revenue00:31:16 Too Boring for the Crypto Bull Market00:38:45 Losing JP Morgan, Then Winning It Back00:43:23 Never Regret Firing Too SoonSend me a message to let me know what you think!

Andrew spent two and a half years selling AI contract review to lawyers. It stalled at $800K. He rebuilt the company around finance teams and grew that to $10M. Then he demoed a little internal tool on the side at his own conference, and nobody wanted to talk about anything else. It did $350K in five weeks. He sold the $10M business and went all in on the side tool—Within went from zero to nearly $20M in 18 months. In this episode, Andrew breaks down the 30-and-100 rule he uses to validate every idea, how he turned every customer conversation into a database that tells him what to build next, and why nine out of ten experiments have to fail. Why You Should Listen Why 30 conversations validate an idea and 100 customers reveal product market fit.Why the thing everyone asks about matters more than the thing you launched.How to tell that slow growth is a market problem, not a go-to-market problem.How to run four bets a quarter with a kill metric on every one.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Within, Klarity, Andrew Antos, enterprise AI, AI transformation, pivoting a startup, enterprise sales, legal tech, finance automation, AI agents, customer discovery, voice of customer Chapters 00:00:00 Intro00:02:04 The Side Tool Everyone Wanted00:04:26 $350K in Five Weeks00:05:42 AI for Lawyers Before AI Worked00:12:44 Stuck at $800K00:13:43 Choosing Finance Over Legal00:17:40 The 30 and 100 Rule00:24:59 Selling the $10M Business00:32:17 Building a Company Data Brain00:40:01 Nine of Ten Bets FailSend me a message to let me know what you think!

AJ spent two years selling health benefits with no customers and no references. His competitors told buyers their service was free. He charged a flat fee and told the truth about where the money actually went. Two years in, at $10M ARR, a Fortune 500 company called him. Judi Health just raised $400M at a $3.25B valuation. In this episode, AJ breaks down how he beat three Fortune 15 giants by operating 70% more efficiently, why he spent zero on marketing for two years and let customers sell for him, and the one hiring signal he refuses to ask about directly. Why You Should Listen Why $10M ARR still felt like nothing against three Fortune 15 competitors.How to sell healthcare when your answer to "who are your customers" is "just you."Why he spent $0 on marketing and made customers the brand ambassadors.How he spots A players without ever asking them about the mission.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Judi Health, Capital Rx, AJ Loiacono, pharmacy benefit management, PBM, healthcare startup, enterprise sales, transparent pricing, bootstrapping, self-insured employers, hiring for mission Chapters 00:00:00 Intro00:02:11 Why Healthcare Has No Shortcuts00:05:34 What Judi Health Actually Does00:11:27 Opacity As A Business Strategy00:15:12 Bootstrapping In A Regulated Market00:21:50 Selling The First Risky Customers00:27:15 Winning Bids When Rivals Look Free00:33:37 Zero Marketing And A Service Moat00:42:20 Hiring For Mission And A Players00:52:35 Founder Advice On Focus And DisciplineSend me a message to let me know what you think!

Niklas quit law school to install CCTV cameras in iPhone repair shops. Eight years later he sold that business to private equity at 26. Then he went after the most boring software in the world: the 1997 tool engineers use to design the wiring and plumbing inside buildings. He spent $150K on a website before he had a product and DM'd engineers on Reddit to find his first users. His first month of sales was $1.5M, all enterprise. Endra has now raised $75M, including a $50M Series A led by a16z. In this episode, Niklas breaks down why he spent $150K on brand before there was a product, how DMs in Reddit engineering threads turned into $300K enterprise contracts, and the hiring principles he used to screen the first 50 employees. Why You Should Listen Why spending $150K on brand before you have a product can be the right call.How DMs in Reddit threads turned into $300K enterprise contracts.Why your customer's competitors are your best sales channel.How to know when 80% output is actually enough to sell.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Endra, Niklas Lindgren, MEP engineering, AI for construction, vertical AI, enterprise sales, brand building, Reddit marketing, hiring principles, agentic design software Chapters 00:00:00 Intro00:02:23 $1.5M of Enterprise Revenue in One Month00:04:22 Why Enterprises Couldn't Say No00:06:04 What Endra Actually Does00:08:27 Law School to CCTV Cameras00:12:06 Recruiting Two Goldman Engineers00:17:11 Finding Users in Reddit Threads00:26:02 $4M, $20M, Then $50M From a16z00:35:00 Spending $150K on Brand Before a Product00:40:11 The Hiring Principles ManualSend me a message to let me know what you think!

Colin spent eight years building Looker into a $2.7B Google acquisition. Then he left to compete with his own product. He thought traction would take a month—it took nine. A hundred demos got him five verbally-committed customers, and he lost all five. So he spent two months killing bugs, went on one podcast, and won every single trial that came out of it. Omni just raised over $250M. In this episode, Colin breaks down how to tell the difference between a product that's genuinely better and one the market just doesn't want, why founding with $30M didn't stop them from staying stingy, and the LinkedIn playbook that turned 6,000 connections into a 90% response rate. Why You Should Listen Why losing every deal doesn't mean the idea is wrong—and how to know the difference.Why real differentiation shows up as "wow" moments in demos, not signed contracts.The LinkedIn social-selling playbook that built Omni's first pipeline.Why hiring sellers from your old industry hands you their Rolodex on day one.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Omni, Colin Zima, Looker, business intelligence, BI tools, enterprise SaaS, AI analytics, social selling, LinkedIn outbound, founder-led sales, innovator's dilemma Chapters 00:00:00 Intro00:01:58 The Moment of True Product Market Fit00:06:16 Losing All Five Deals and Doubling Down00:10:43 Leaving Looker to Compete With Looker00:17:39 Founding With $30M and Staying Stingy00:22:09 A Hundred Demos Before the Flywheel00:32:15 No Silver Bullet—Just Do More of Everything00:38:32 The LinkedIn Social-Selling Playbook00:46:07 Hiring the Best People You've Worked WithSend me a message to let me know what you think!

Rafael launched a crypto insurance product in 47 states, backed by a real carrier. Everyone told him it was genius. Nobody needed it. He shut it down with $2M left in the bank, fired almost everyone, and rebuilt with two engineers on $20K a month. Notch just raised $30M. In this episode, Rafael breaks down how a POC he entered through the back door turned into a seven-figure contract, why "isn't everyone doing this?" is the feedback you actually want, and how to tell whether an enterprise deal makes you a real company or just their dev shop. Why You Should Listen Why "that idea is genius" is a warning sign, not a compliment.How entering a POC last still made them the front runner.Why the enterprise deals that scale need zero customization.How to stop hiding your idea and go straight to your dream customers.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Notch, Rafael Broshi, AI agents, insurance technology, customer experience automation, regulated industries, enterprise sales, POC strategy, pivoting a startup, on-prem deployment Chapters 00:00:00 Intro00:02:00 The Moment of True Product Market Fit00:10:07 One Enterprise Deal or Ten00:15:24 A Genius Idea Nobody Needed00:24:33 Picking the Right Wave to Ride00:34:37 Down to $2M, Firing Almost Everyone00:41:48 Getting Enterprise to Take Your Call00:48:07 The POCs That Aren't Real POCsSend me a message to let me know what you think!

Ben and his co-founder had no product, no law enforcement background, and no pitch—just an offer to help detectives solve cases. One commander took a chance, handed them background checks, and said "let's see what you can do." They worked out of that police department every day for 18 months. Peregrine just raised $250M at a $6.8B valuation. In this episode, Ben breaks down how researching every police captain in the Bay Area landed their first design partner, why working as free crime analysts for 18 months was "the purest form of method acting," how forward-deployed engineers drove them from $1M to $3M to $10M ARR, and the 120% RFP prep that won a contract written for a billion-dollar competitor. Why You Should Listen Why doing your customer's job is the fastest path to product market fit.How two founders with no product convinced a police department to let them in.Why over-investing in deployment became a growth engine, not a margin problem.How obsessive research wins enterprise deals when you have zero credibility.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Peregrine, govtech, public safety technology, forward deployed engineers, selling to government, enterprise sales, data integration, design partners, Ben Rudolph Chapters 00:00:00 Intro00:01:07 The Moment of True Product Market Fit00:11:51 Getting a Police Department to Say Yes00:16:45 Slow Growth and Word of Mouth00:19:49 Forward-Deployed Engineers Before They Were Cool00:27:34 Cracking Government Go-To-Market00:34:08 Winning an RFP Written for Someone ElseSend me a message to let me know what you think!

Damien left his job to start a startup solo. Two years later, Nebulock closed a $25M Series A. In between: 90 customer interviews in 90 days, a year of design partners, and a Fortune 500 deal that closed in 6 weeks. In this episode, Damien breaks down how his 90-in-90 customer discovery sprint killed his original architecture before he wasted money building it, how his design partner program converted 100% into paying customers, and how a POC playbook needing just 2 hours of customer time closed a Fortune 500 in 6 weeks. Why You Should Listen How 90 customer interviews in 90 days saved him from building the wrong product.Why every single design partner converted into a paying customer.How a 2-hour POC playbook closed a Fortune 500 in just 6 weeks.Why procurement—not your champion—decides how fast your deal closes.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, cybersecurity startup, solo founder, customer discovery, mom test, design partners, enterprise sales, POC process, AI security, Nebulock, Damien Lewke Chapters 00:00:00 Intro00:01:20 The Moment of True Product Market Fit00:11:33 Going Cold Turkey as a Solo Founder00:23:07 90 Interviews in 90 Days00:36:44 Raising $8.5M Off a Manifesto, Not a Deck00:39:36 Every Design Partner Converted to Paid00:44:00 Building a Repeatable POC Playbook00:48:20 The Procurement Black HoleSend me a message to let me know what you think!

Astro has run X, Alphabet's Moonshot Factory, for 16 years. His teams created Waymo, Wing, and Google Brain—by testing over 1,000 ideas a decade and killing nearly all of them. His whole system rests on one uncomfortable rule: celebrate the people who kill their own projects. In this episode, Astro breaks down why you should do the hard thing first, how pre-written kill criteria force intellectual honesty, and why X maximizes learning per dollar instead of progress—and never tracks whose idea it was. Why You Should Listen Why working on the riskiest part first is the key to testing new ideasHow writing kill criteria a year in advance stops you from running a zombie startup.Why progress doesn't matter when launching a new startup.How to come up with big ideas like Waymo and Wing.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Astro Teller, Google X, moonshot factory, Alphabet, Waymo, innovation process, kill criteria, idea validation, deep tech Chapters 00:00:00 Intro00:04:15 Inside Alphabet's Moonshot Factory00:07:22 The Card Counters of Innovation00:14:00 Learning per Dollar, Not Progress00:23:04 Killing Ideas with Testable Hypotheses00:26:34 Train the Monkey First00:35:16 Kill Criteria: A Message to Your Future Self00:41:59 The Moment of True Product Market FitSend me a message to let me know what you think!

Cos was the CTO of Brex, which he helped scale from 40 people to over 1,000. Before that, he led engineering at Stripe. When he finally left, he had no startup idea—just a co-founder he trusted and one rule: whatever they built had to have massive impact. Six months of brainstorming later, they landed on accounting. In this episode, Cos breaks down why he capped the company at 21 people after raising $75M, why everyone—engineers and salespeople alike—earns the exact same salary, how he hit a 100% pilot-to-production conversion rate with top accounting firms, and the counterintuitive process he used to pick accounting over every other industry. Why You Should Listen Why the only reason to join an early-stage company should be the equity, never the cash.How Accrual hit a 100% pilot-to-production conversion rate selling to the largest accounting firms.Why he raised $75M but refuses to grow past 21 people.How to tell real product market fit from the "just one more feature" trap.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI accounting, vertical AI, enterprise sales, pilot to production, Brex, Stripe, Cosmin Nicolaescu, Accrual, lean team Chapters 00:00:00 Intro00:01:56 The Moment of True Product Market Fit00:09:46 Collapsing 6+ Tools Into One Platform00:18:07 Leaving Brex to Start From Scratch00:31:41 Landing H&R Block and Armanino00:34:57 A 100% Pilot-to-Production Playbook00:43:26 A 21-Person Company by Design00:51:38 One Salary for EveryoneSend me a message to let me know what you think!

Anurag was employee #8 at Stripe, set for life and free to do anything next. Instead he spent a year and a half hunting for a problem worth decades of his life. He chose to build a product to make it simple for developers to ship apps, going head-to-head with AWS. In this episode, Anurag breaks down how he hit $10M ARR in 4 years with zero marketing spend, why refusing to launch a free tier was his most expensive mistake, and how putting engineers on customer support rotations quietly shaped the entire product roadmap. Why You Should Listen Why you don't have real product market fit until your users sell the product for you.How a sub-2-minute setup turned developers into a word-of-mouth machine.Why skipping a free tier for years was his most expensive mistake.How engineers doing support on rotation built the roadmap—and 6M+ developers.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, developer tools, cloud infrastructure, PaaS, Render, word of mouth growth, product-led growth, AI infrastructure, Stripe Chapters 00:00:00 Intro00:01:44 The Moment of True Product Market Fit00:04:14 The #1 Driver of Word of Mouth00:13:25 Why He Left Stripe to Build Render00:23:48 Why AWS Would Never Build This00:30:33 $10M ARR With No Marketing Spend00:36:43 Engineers as the Support Team00:42:19 Riding the AI BoomSend me a message to let me know what you think!

George had to wind down his last startup and give investors their money back. He went deep into the valley of despair, certain he'd missed his window to build something big. Then he met a co-founder, decided to start over, and started selling. In this episode, George breaks down how a customer signed a $36K pilot off nothing but a Loom and a one-pager, how cold email took him from zero to $1M ARR with no sales team, and why a "seven out of ten" is the most dangerous hire you can make. Why You Should Listen How a customer signed a $36K pilot after a single Loom and zero calls.Why he gave the money back on his last startup—and what "follow your energy" really means.How cold outbound email built his first $1M ARR with no sales team.Why a "seven out of ten" is the most dangerous hire you can make.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, fintech, accounts receivable automation, AI agents, cold outbound email, B2B SaaS, Series A fundraising, services as software Chapters 00:00:00 Intro00:01:39 The Moment of True Product Market Fit00:03:33 Shutting Down a Small-Market Startup00:07:44 Picking Fintech From Five Ideas00:17:12 From Black Box to Full App00:24:47 $1M ARR on Cold Email Alone00:36:11 Why a "Seven" Is the Most Dangerous Hire00:42:15 Compressing a $25M Series ASend me a message to let me know what you think!