Explore every episode of the podcast A Product Market Fit Show | Startup Podcast for Founders
| Title | Pub. Date | Duration | |
|---|---|---|---|
| He runs 3 dinners a week instead of cold outbound—and closes $500K+ ARR deals. | Nick Fleisher, Co-Founder & CEO of Sandstone | 28 sept. 2026 | 00:49:10 | |
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
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
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| Revenue fell from $25M to $8M—so he raised $75M in crowdfunding and ignored VCs. | Dan Novaes, Co-Founder & CEO of Mode Mobile | 21 sept. 2026 | 00:51:06 | |
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
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
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| He turned off a product with 20M users and went from 70 people to 7—then raised a $47M Series A. | Keith Peiris, Co-Founder & CEO of Lightfield | 14 sept. 2026 | 00:45:31 | |
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
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
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| VCs chased crypto and passed on his “boring” startup—then he raised $385M at a $2B valuation. | Aaron Schumm, Founder & CEO of Vestwell | 07 sept. 2026 | 00:49:49 | |
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
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
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| He sold his 8-figure business to bet on a side app—then grew it to 20x in a year. | Andrew Antos, Co-Founder & CEO of Within | 31 août 2026 | 00:49:31 | |
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
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
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| He spent $0 on marketing for 2 years—then raised $400M at a $3.25B valuation. | AJ Loiacono, Co-Founder & CEO of Judi Health | 24 août 2026 | 00:55:03 | |
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
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
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| He spent $150K on brand before he had a product—then closed $1.5M ARR in 1 month. | Niklas Lindgren, Co-Founder & CEO of Endra | 17 août 2026 | 00:46:17 | |
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
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
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| He lost all 5 of his first deals—then built the next Looker and raised $250M. | Colin Zima, Co-Founder of Omni | 10 août 2026 | 00:52:38 | |
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
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
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| He fired almost everyone, kept 2 engineers—then grew 12x and raised a $30M Series A. | Rafael Broshi, Co-Founder of Notch | 03 août 2026 | 00:52:42 | |
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
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
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| He worked out of a police department for free for a year—then built a $6.8B company. | Ben Rudolph, Co-Founder of Peregrine | 27 juil. 2026 | 00:40:44 | |
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
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
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| 1st-time solo founder does 90 interviews in 90 days—closes a $25M Series A 2 years in. | Damien Lewke, Founder of Nebulock | 20 juil. 2026 | 00:50:28 | |
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
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
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| He tries 1,000 ideas a decade & kills nearly all—that's how X built Waymo & Google Brain. | Astro Teller, CEO of Moonshots at X (Alphabet) | 13 juil. 2026 | 00:48:06 | |
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
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
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| He raised $75M—but kept his team to 21 people & pays everyone the same salary. | Cos Nicolaescu, Co-Founder of Accrual | 06 juil. 2026 | 00:57:38 | |
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
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
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| He quit Stripe and hit $10M ARR in 4 years—with $0 marketing spend. | Anurag Goel, Founder of Render | 29 juin 2026 | 00:47:43 | |
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
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
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| He shut down his last startup and gave the money back—then hit $1M ARR in 6 months. | George, Founder of Monk | 22 juin 2026 | 00:46:05 | |
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
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
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| He quit his $50M ARR startup to work as a paralegal—then raised a $60M Series A. | Dan Mishin, Founder of Manifest | 15 juin 2026 | 00:42:37 | |
Dan founded and scaled a $50M ARR, SoftBank-backed startup—and could've stayed to make tens of millions. Instead, he handed it to his chief of staff and started from scratch. He wanted something bigger. He took an entry-level paralegal job to learn everything about law hands on. Then he built Manifest, which just raised a $60M Series A. In this episode, Dan breaks down why he did intake calls for 1,000 legal clients before building anything, how free Slack communities turned Fortune 500 HR managers into buyers without a dollar of ads, and why he refused to sell software to law firms even when investors told him he was crazy. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, legal tech, legal AI, AI-native law firm, immigration law, services as software, community-led growth, earned media, customer discovery, Dan Mishin, Manifest
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| He churned 100% of his revenue on purpose—then grew 10x to $2M ARR in under 12 months. | Ali Khokhar, Founder of Amigo AI | 08 juin 2026 | 00:53:00 | |
Ali quit his job a few months after ChatGPT launched, convinced AI would eat labor marketplaces like Upwork. With no co-founder and no code, he collected $12K from real customers—using a faked demo and a cloned voice. Then he pitched 100 VCs in 10 days and got 47 straight 'no's. In this episode, Ali breaks down how he banked $12K in revenue before writing a single line of code, how a $20/month Slack community drove Amigo's first $1M in ARR, and why he churned every existing customer to go all-in on $100K+ healthcare enterprise deals. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI agents, healthcare AI, enterprise sales, pre-seed fundraising, community-led growth, customer validation, pivot, Amigo AI Chapters
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| He hit $1M ARR by sending 500,000 cold emails—then raised a $25M Series A in 6 days. | Mark Hughes, Co-Founder of Solidroad | 01 juin 2026 | 00:42:52 | |
Mark was running a startup out of a tiny annex office in Dublin with zero product usage. Then one customer turned it on and overnight he saw usage spike to thousands of simulations. He got to $1M ARR 100% through outbound, by sending 500,000 cold emails. A few months ago he closed a $25M Series A. In this episode, Mark breaks down the pivot from sales roleplay to customer support that unlocked his first real traction, the cold outbound playbook that took him to $1M ARR (500K emails, 250 meetings, 40 customers), and why doorstepping customers in Utah is what drove his net revenue retention to 186%. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI startup, customer support, cold outbound, Y Combinator, Series A, enterprise sales, SaaS, Solid Road
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| Q1 2026 w/Carta: What you need to raise a Series A. | Peter Walker, Head of Insights at Carta | 25 mai 2026 | 00:38:28 | |
The AI boom is making founders feel like the market is wide open, but the data tells a sharper story: valuations are up, round sizes are bigger, and the bar to “count” in a top-tier fund’s Monday meeting keeps rising. We sit down with Peter to translate Q1 2026 venture capital trends into founder reality, from seed-stage pricing distortions driven by AI infrastructure to the quieter pressure building across the rest of the startup market.
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| How to get a VC (like me) to wire you $2M in under 2 weeks (the FOMO playbook) | Solo Episode | 18 mai 2026 | 00:21:47 | |
I meet 1,000+ founders every year. Most are bad at fundraising. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, fundraising, raising a seed round, VC pitch, FOMO, startup fundraising playbook, term sheets, investor meetings, Pablo Srugo, venture capital Chapters
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| Coinbase's ex-CPO bet on AI agents before ChatGPT—now he's closing 7-figure Fortune 500 deals. | Surojit Chatterjee, Founder of Ema | 11 mai 2026 | 00:37:27 | |
Surojit spent 14 years at Google building mobile ads into a $100B+ business and then took Coinbase public as Chief Product Officer in 2021. In early 2023, before "agent" was even a word in AI papers, he started Ema in stealth—betting on a future where teams of AI agents would replace the "human glue" inside Fortune 500s. In this episode, Surojit breaks down how a Hitachi deployment across 55,000 employees became Ema's true PMF moment, why he spent the first year obsessed with SOC 2, ISO 42001, and air-gapped architecture before chasing revenue, and why one client just cut their HR team from 1,000 people to 550 by automating 65,000 monthly job changes. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI agents, enterprise AI, AI employees, Fortune 500 sales, Surojit Chatterjee, Ema, agentic AI, enterprise software
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| How this 1st-time founder went from closing customers for $500 a month to $300,000 a year. | Sean McCarthy, Founder & CEO of BackOps | 04 mai 2026 | 00:55:46 | |
Sean was spending four days a week inside customer warehouses at Amazon Shipping when he noticed the same thing everywhere: back-office admin staff churning every six months, buried under the same repetitive claims and reshipping tasks. He talked to eighty-five warehouse owners, quit Amazon in July 2024, and cold emailed his way to a pre-seed round within weeks. In this episode, Sean breaks down why he paused all sales to rebuild BackOps as an enterprise-grade platform, how an SOP recorder that takes eight minutes replaced months of deployment delays, and the scrappy enterprise playbook—from sending donuts to warehouses to building the customer's board deck for them—that wins $300K Fortune 500 deals. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, supply chain, AI automation, enterprise sales, BackOps, first-time founder, warehouse operations, logistics AI, Sean McCarthy, agentic AI
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| He built for 2 years before raising a dollar—then hit $13M ARR and a $40M Series B. | Alex Halliday, Co-Founder & CEO of AirOps | 27 avr. 2026 | 00:40:45 | |
Alex spent two years building AirOps nights and weekends during the pandemic before raising a single dollar. A chance conversation with Sam Altman—while walking down the street during SF Pride—sent him down the LLM rabbit hole months before ChatGPT existed. He pivoted his product toward AI, picked marketers as his customer, and never looked back. In this episode, Alex breaks down why he picked marketers over every other AI use case after watching them build 80-step workflows on his platform, the consultative sales motion that converts almost every pilot to annual at $60K–$250K ACVs, and why positioning—not product—was the unlock that took AirOps from $1M to $13M ARR. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI marketing, content engineering, SEO, AEO, AI search, enterprise sales, SaaS growth, AirOps, Alex Halliday, Greylock
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| 180 VCs rejected him—then a $60K billboard got him to $2M ARR in 4 months. | Isaiah Granet, CEO of Bland AI | 20 avr. 2026 | 00:52:22 | |
Isaiah pivoted mid-YC, landed in the bottom 10% of his batch, and watched 180 investors say no—their reason: phone calls won't exist a year from now. Voice AI was not yet a thing. With almost no money left, he and his co-founder bet everything on building AI phone calls from scratch. Bland went from pre-seed to a $40M Series B in a year. In this episode, Isaiah breaks down how a $60K billboard and a strategic influencer campaign generated close to a billion impressions, why he fired 50% of his customers right after raising a Series A, and the enterprise sales playbook that lands six- and seven-figure contracts with companies most people have never heard of. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, voice AI, AI phone calls, enterprise sales, Bland AI, YC pivot, billboard marketing, influencer marketing, call center automation, Isaiah Granet
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| She bet on a consumer app when every VC wanted B2B—then grew to $10M ARR. | Anada Lakra, Founder of BoldVoice | 16 avr. 2026 | 00:52:20 | |
Anada Lakra just raised a $21M Series A for BoldVoice, a $150/year pronunciation app that helps immigrants speak English with confidence. But she started from zero in her Harvard dorm room and a problem most VCs didn't think was big enough. She recruited a Hollywood accent coach, shipped a bare-bones V1, and got into YC. In this episode, Anada breaks down why she launched a consumer app when every investor was chasing B2B, how a Reddit thread called "Judge My Accent" became an early growth hack, and why switching to annual-default pricing transformed her unit economics overnight. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, consumer app, B2C startup, pronunciation app, accent coaching, AI app, YC startup, mobile app growth, Anada Lakra, BoldVoice
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| He raised a $10M seed with no revenue—then grew 30x to $30M in year two. | Bobby Samuels, Founder of Protege | 13 avr. 2026 | 00:39:24 | |
Bobby launched Protege in early 2024 to connect data holders with AI model builders. He raised a $10M seed with almost no demand pipeline. A year later, Protege jumped 30x to $30M in GMV and raised $30M from a16z. In this episode, Bobby breaks down how he built a 250-partner data network by leveraging prior healthcare relationships, why he flies from New York every week to close seven-figure enterprise deals, and why the "texting terms" litmus test tells you if a deal is real. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI data, enterprise sales, founder-led sales, data licensing, healthcare AI, a16z, B2B startup, Bobby Samuels, Protege Chapters
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| He ran Prime fulfillment for Amazon—then raised $20M to replace e-commerce with AI. | Maju Kuruvilla, Founder of Spangle | 09 avr. 2026 | 00:42:01 | |
Maju ran Prime fulfillment technology for all of Amazon — same-day, one-hour shipping, global logistics during the pandemic. He became CEO at Bolt. Then he walked away to start Spangle in a basement with a co-founder, convinced AI could replace e-commerce infrastructure as we know it. In this episode, Maju breaks down why 40% of e-commerce traffic loses its context the moment it arrives on a brand's site, how Spangle's AI dynamically rebuilds the entire storefront in real time for each visitor, and why he believes the future of commerce will be a battle between AI seller agents and AI buyer agents. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, e-commerce, AI commerce, agentic commerce, personalization, dynamic storefronts, conversion optimization, enterprise SaaS, Series A, Spangle, Maju Kuruvilla
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| She got rejected by 22 VCs—then built 6sense to $100M+ in revenue. Now she's back for AI. | Amanda Kahlow, Founder of 1mind | 06 avr. 2026 | 00:52:13 | |
Amanda spent 16 years running a services business for Cisco and Intel. When she tried to productize her business, 22 VCs rejected her. That became 6sense, a $200M ARR company. After stepping aside as CEO and taking five years off, she's back with an AI startup called 1 mind. In this episode, Amanda breaks down why she always goes enterprise-first when everyone tells her to start small, how she used an AI clone of herself to pitch 60 VCs and raise 1mind's Series A in three days, and why she believes the entire sales process—SDRs, AEs, sales engineers—is about to be collapsed into a single AI "superhuman." Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, AI agents, AI sales, enterprise sales, 6sense, 1mind, finding pmf, B2B SaaS, AI enabled services, net dollar retention Chapters
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| How this AI founder is on track to hit $50M ARR just 2 years after launch. | Tarek Alaruri, Co-Founder of Stuut | 02 avr. 2026 | 00:47:16 | |
Tarek already built a B2B software company to $30M ARR. But when the AI wave hit, he realized he could build a generational business by automating the manual world of accounts receivable. So, he left to start Stuut. In this episode, Tarek breaks down how he reached $1M ARR in a couple of months and is on track to hit up to $50M this year. He reveals how he pre-sold his first $65k contract with just wireframes, why he forces new customers to introduce him to five peers, and the brutal reality of finding message-market fit through hundreds of cold calls. Why You Should Listen
00:00:00 Intro | |||
| He launched a free product for enterprise customers—then grew to $12M ARR in 2 years. | Bhaskar Sunkara, Founding CTO of AppDynamics | 30 mars 2026 | 00:44:59 | |
Description Bhaskar was employee #1 at AppDynamics, which was sold to Cisco for $3.7B. He and co-founder Jyoti found a way to change how enterprise monitoring tools worked. From tracking low-level code metrics that ops teams didn't understand to monitoring what the business actually cares about. In this episode, Bhaskar breaks down how that one insight won them Netflix and Priceline as early customers, why they ran production POCs that no competitor would dare try, and how a free download called AppDynamics Lite generated over 60% of their leads—in an industry where getting started normally took weeks of professional services and six-figure contracts. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, AppDynamics, application monitoring, enterprise SaaS, B2B sales, finding pmf, freemium strategy, Cisco acquisition, production POC Chapters
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| He raised $41M in one year to replace enterprise accountants with AI. | Yogi Goel, Founder of Maxima | 26 mars 2026 | 00:43:49 | |
Yogi spent 20 years living the nightmare of enterprise accounting. As a senior finance leader at Rubrik, he watched highly paid professionals spend three weeks every month manually wrangling data into spreadsheets—a problem that caused mass burnout and multi-million dollar stock corrections. When ChatGPT launched, Yogi knew the technology was finally ready to solve the problem. In this episode, he breaks down how he left his executive track to found Maxima, how he landed massive enterprises like Scale AI and Rippling as early design partners, and why he managed to raise $41M from top-tier VCs like Kleiner Perkins and Redpoint before he even had a pitch deck. Why You Should Listen
Keywords startup podcast, startup podcast for founders, AI in accounting, enterprise SaaS, product market fit, finding pmf, raising seed round, raising series a, B2B sales, design partners 00:00:00 Intro | |||
| How he grew his AI startup from $2M to $20M ARR in 12 months. | Omar Haroun, Co-Founder of Eudia | 23 mars 2026 | 00:49:29 | |
Omar already built and sold an AI startup for over $100M. But when the generative AI wave hit, he realized the technology wasn't just the future of software—it was the future of labor. So he started Eudia to completely transform how enterprise legal teams operate. In this episode, Omar breaks down how he scaled from $2M to $20M ARR in just 12 months. He reveals the exact cold email strategy he used to land C-suite design partners, why he bought an existing legal services company to accelerate his AI platform, and why replacing human labor with AI is the ultimate business model. Why You Should Listen
Keywords startup podcast, startup podcast for founders, AI startups, product market fit, AI enabled services, legaltech, B2B SaaS, enterprise sales, finding pmf, generative AI 00:00:00 Intro | |||
| She raised $20M from Accel to replace QuickBooks with AI. | Helen Hastings, Founder of Quanta | 19 mars 2026 | 00:56:39 | |
Helen was a software engineer who noticed a massive problem: accounting software for startups was broken, manual, and weeks out of date. Instead of just building a shiny new dashboard on top of legacy platforms, she decided to completely replace the offshore accounting model with AI. In this episode, Helen breaks down how she raised a $4.7M seed round pre-product as a solo founder and why she chose to build an AI-enabled service instead of pure software. She reveals the exact user research playbook she used across 200 interviews, how to rebuild a monopoly like QuickBooks, why hitting product-market fit actually forced her to stop taking new customers, and how she raised a $15M Series A. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, AI enabled services, fintech startup, user research, solo founder, raising seed round, B2B SaaS, finding pmf | |||
| He moved to the US with nothing. Now he does $750M ARR. | Mateo Marietti, Founder of CookUnity | 16 mars 2026 | 00:56:24 | |
Mateo had already built a successful food company in Argentina. But he wanted more. So he moved to New York with no network, no credibility, and a dream to build the "Spotify for Food." The first two years were messy. He nearly ran out of money multiple times, relied on corporate expense accounts to keep the lights on, and failed a major expansion into LA. But then, he noticed a strange behavior: some customers were ordering 10 meals at a time. That single insight led to a massive pivot, a partnership with world-class chefs, and eventually, a $750M run rate. In this episode, Mateo breaks down the gritty reality of building a marketplace from scratch, how to survive the "messy middle," and why sometimes you have to kill your revenue to save your company. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, food tech, marketplace startups, pivot, founder story, CookUnity, scaling a startup, immigrant founder 00:00:00 Intro | |||
| This 3x founder hit $1M ARR in 5 months. Here's his playbook. | Roy Moussa, Founder of GetVocal | 12 mars 2026 | 00:44:13 | |
Roy is a three-time founder who has cracked the code on enterprise AI. After selling his first company and realizing his second idea was too slow, he pivoted to solving a massive problem: customer service automation. In this episode, Roy breaks down how GetVocal went from zero to $1M ARR in just five months. He reveals the "Context Graph" technology that allows them to beat LLM wrappers, why he believes purely generative AI is useless for business, and how he turned a single deployment into an enterprise-wide contagion. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, enterprise AI, customer service automation, finding pmf, context graphs, AI agents, B2B sales, Roy Moussa 00:00:00 Intro | |||
| He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Ryan Anderson, Founder of Filevine | 09 mars 2026 | 00:56:43 | |
Ryan was a successful lawyer with a massive problem. He couldn't find a task management tool that worked for his firm, so he built one himself. He thought he'd solved the problem, but for 8 agonizing months, he couldn't sell a single subscription. In this episode, Ryan breaks down the gritty reality of bootstrapping Filevine into a $3B legal tech startup doing over $200M in revenue. He shares how a random Instagram ad campaign ended his sales drought, how he fought off a Tiger Global-backed competitor built on Salesforce, and how he's completely rewriting his company's architecture to win the AI legal tech war against the likes of Harvey and Legora. Why You Should Listen
Keywords startup podcast, startup podcast for founders, legaltech, product market fit, bootstrapping, B2B SaaS, enterprise sales, AI startup, founder story, finding pmf 00:00:00 Intro | |||
| He built heads down for a year. Then landed a $1M contract. | Sam Jones, Co-Founder of Method Security | 05 mars 2026 | 00:45:13 | |
Sam spent years at the Air Force and Palantir before deciding to build Method Security. Instead of launching an MVP and iterating with customers, he did the opposite: he shut out the world and built in the dark for a year based on his own conviction. In this episode, Sam breaks down his contrarian approach to building a platform for the enterprise and government. He reveals how he raised millions from Andreessen Horowitz with just a prototype, why he refuses to hire a sales team, and how he landed a seven-figure contract right out of the gate. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, cybersecurity, a16z, Palantir, enterprise sales, design partners, government contracting, founder led sales 00:00:00 Intro | |||
| He raised $150M with $0 revenue. Then hit $1M ARR in 4 months. | Michel Tricot, Co-Founder of Airbyte | 02 mars 2026 | 00:42:59 | |
Michel raised $185M and achieved a unicorn valuation before he fully cracked monetization. How? By building a community so strong it broke his engineering team. In this episode, Michel breaks down the chaotic journey from a failed YC marketing idea to becoming the standard for open-source data movement. He reveals why he killed a high-growth fintech product, how he used the "Magic Wand" question to find his true direction, and the specific insight that allowed Airbyte to hit $1M ARR in just 4 months after launching their enterprise product. Why You Should Listen
Keywords startup podcast, startup podcast for founders, open source business model, data infrastructure, product market fit, Y Combinator, pivoting, fundraising, developer tools, Airbyte 00:00:00 Intro | |||
| He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails | 26 févr. 2026 | 00:38:28 | |
Didi spent five years building a product that no one really wanted. He raised $10 million, tried endless pivots, and was known as the "black sheep" of his investors' portfolio. Then, with his back against the wall, he made one final bet on a boring, unsexy market: FP&A for Excel users. In this episode, Didi breaks down how that final pivot turned into a rocket ship. He reveals why he sold cheap monthly contracts to prove demand, how he used his kids to automate LinkedIn outreach, and why targeting the market everyone else ignores (Excel lovers) was the key to unlocking massive growth. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, B2B sales, outbound sales strategy, FP&A software, excel automation, Didi Gurfinkel 00:00:00 Intro | |||
| His startup powers OpenAI's Voice Mode. Last month, they became a unicorn. | Russ d’Sa, Co-Founder of LiveKit | 23 févr. 2026 | 00:55:18 | |
Russ was running a moderately successful live streaming startup. Then he got a terrifying offer from a tech giant: sell to us for cheap, or we'll crush you. He had no leverage. He was about to fold. Then he got an email from OpenAI. They had secretly built ChatGPT's voice mode on his infrastructure. Overnight, everything changed. In this episode, Russ reveals the wild story of how LiveKit became the backbone of multimodal AI, why he almost sold his previous company for parts, and how to survive when the biggest companies in the world are breathing down your neck. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, AI infrastructure, multimodal AI, OpenAI, ChatGPT voice mode, founder stories, pivot, LiveKit 00:00:00 Intro | |||
| He pivoted at $1M ARR—then raised $120M. | Kevin Tian, Co-Founder of Doppel | 19 févr. 2026 | 00:36:21 | |
Kevin was building a successful startup in the NFT space. They'd hit $1M ARR. But he looked at the market and realized it wasn't big enough. So he made the terrifying choice to pivot the entire company into cybersecurity. In this episode, Kevin breaks down how he navigated that transition without killing the business. He reveals how he sold his first $5k/month contract with no product, why he raised a massive seed round he didn't need, and how he convinced Andreessen Horowitz to lead his Series A in the middle of a strategic shift. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, cybersecurity, crypto startup, a16z, raising series a, Kevin Tian 00:00:00 Intro | |||
| He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves | 16 févr. 2026 | 00:55:54 | |
Dileep sold his first company for over $100M. For his second act, he didn't just want another win; he wanted to solve a problem that banks refused to touch: global business banking. In this episode, Dileep breaks down how Jeeves scaled to $7M ARR in just over a year by doing things that "don't scale"—like physically mailing credit cards to Argentina. He reveals the counterintuitive strategy of raising from dozens of small investors, how to pivot a fintech when interest rates skyrocket, and why being an outsider was his biggest advantage in building a global banking infrastructure from scratch. Why You Should Listen
Keywords startup podcast, startup podcast for founders, product market fit, fintech startup, global expansion, second time founder, Y Combinator, fundraising strategy, B2B banking, finding pmf 00:00:00 Intro | |||
| He sold his first 2 startups. His 3rd grew to $1M ARR in 3 months. | Chaz Englander, Founder of Model ML | 12 févr. 2026 | 00:49:44 | |
Chaz has founded 3 companies. The first sold for over $40M. The second sold to GoPuff for even more. Now, he’s on his third act with Model ML, having just raised $75M Series A <2 years in. In this episode, Chaz breaks down the playbook behind his successes. He reveals how he raised his first million by pitching strangers on LinkedIn, why his delivery startup was just a text message system on the backend, and why speed is the only defensive moat left. Why You Should Listen
Keywords startup podcast, startup podcast for founders, serial entrepreneur, fundraising strategy, product market fit, rapid scaling, AI startup, exit strategy, MVP, fintech 00:00:00 Intro | |||
| He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve | 09 févr. 2026 | 00:52:16 | |
Jay was running a respectable AI startup with $3M ARR. But he knew it wasn't a venture-scale rocket ship. So, he decided to fire all his customers, pivot the entire company, and bet everything on a new vertical: legal AI for plaintiff attorneys. Eve went from zero to unicorn status in under two years, raising $100M at a $1B valuation. In this episode, Jay breaks down the brutal reality of pivoting a revenue-generating company, how to achieve "demo shock" in an antiquated industry, and why 4-hour user sessions were the first sign that he had struck gold. Why You Should Listen
Keywords 00:00:00 Intro | |||
| He wrote the book on Account Based Marketing. Here are his GTM secrets for enterprise. | Bassem Hamdy, Founder of Briq | 05 févr. 2026 | 00:39:17 | |
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
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 | |||
| He got rejected from YC—then grew to $1.8B in under 2 years. | Max Junestrand, Founder of Legora | 02 févr. 2026 | 00:52:15 | |
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
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 | |||
| He sold dog food from his condo. Now he does $100M+ a year. | Russell Breuer, Founder of Spot & Tango | 29 janv. 2026 | 00:51:45 | |
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
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 | |||
| He made 100 cold calls a day. Now his startup is worth $600M. | Harman Narula, Founder of Canary Technologies | 26 janv. 2026 | 00:52:03 | |
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
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 | |||
| He got 100k signups in 30 days. They all churned. 2 years later, he hit $10M ARR. | Rich White, Founder of Fathom | 22 janv. 2026 | 00:42:32 | |
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
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 | |||
| He grew his startup to $150M ARR & an IPO. Now he's back for the AI wave. | Bob Tinker, Founder of MobileIron & BlueRock | 19 janv. 2026 | 00:41:00 | |
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
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 | |||