• He moved to the US with nothing. Now he does $750M ARR. | Mateo Marietti, Founder of CookUnity
    Mar 16 2026

    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

    • Why he shut down a $2M revenue stream to pivot to a model with $0 ARR.
    • How identifying the small group of users who would be "very disappointed" unlocked massive scale.
    • Why he failed at expanding the first time, but succeeded the second time by changing just one variable.

    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
    00:02:50 Moving from Argentina to New York
    00:07:43 Why Leave a Successful Business?
    00:13:37 The "Airbnb for Food" Vision
    00:22:44 Faking Traction with Corporate Stipends
    00:28:41 The $2M Pivot: Shutting Down On-Demand
    00:34:54 Why Unit Economics Mattered More Than Revenue
    00:42:14 The COVID Inflection Point & Chef Partnerships
    00:48:09 Failing Fast in LA vs. Succeeding Later
    00:51:54 The Moment of True Product Market Fit

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

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    56 mins
  • This 3x founder hit $1M ARR in 5 months. Here's his playbook. | Roy Moussa, Founder of GetVocal
    Mar 12 2026

    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

    • How to hit $1M ARR in 5 months with a single salesperson.
    • Why "Context Graphs" are the secret to building AI that doesn't hallucinate.
    • How to expand from a single agent to 80 agents across the enterprise.
    • The critical difference between Deterministic and Probabilistic AI
    • Why starting with a personal passion project failed, but pivoting to enterprise worked.

    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
    00:02:29 From Engineer to 3-Time Founder
    00:08:11 The Failed Pivot
    00:12:49 Solving Sales Efficiency First
    00:16:06 The Pivot to Customer Service
    00:18:57 Why Chatbots Failed & The Hybrid AI Solution
    00:25:43 What is a Context Graph?
    00:34:46 The "Contagion" Effect: 80 Agents in 8 Weeks
    00:39:34 Competing with Decagon & The Human-Centric Approach
    00:41:58 Hitting $1M ARR in 5 Months

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

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    44 mins
  • He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Ryan Anderson, Founder of Filevine
    Mar 9 2026

    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

    • How 8 months of zero sales almost broke him.
    • Why building customizability into your core product is the ultimate defense.
    • How to recruit top engineers when you have zero funding.
    • Why SMBs often have "beer money but champagne tastes."
    • How to pivot from SaaS to AI.

    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
    00:07:20 Recruiting an Amazon Engineer with No Funding
    00:11:52 The First Conference and the "Terrible" MVP
    00:15:23 The Dark Months: Zero Sales from Cold Calling
    00:19:28 The GTM that Saved the Company
    00:27:36 Why In-Person Events Beat Cold Calling
    00:36:19 Moving Upmarket to Avoid Demanding SMBs
    00:37:32 Beating a $50M Salesforce-Backed Competitor
    00:46:45 Rewriting Filevine for the AI Era

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

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    57 mins
  • He ignored users for a year. Then landed a $1M contract. | Sam Jones, Co-Founder of Method Security
    Mar 5 2026

    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

    • Why he ignored the "talk to users" advice and built in the dark for a year.
    • How to raise a $5.5M seed round from a16z in just 3 days.
    • The "2-Hour Bootcamp" strategy that shortens enterprise sales cycles.
    • Why keeping your engineering team dangerously small creates speed.
    • How to turn a design partnership into a $1M+ contract.

    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
    00:02:00 From Air Force to Palantir
    00:06:28 The "Shared Notion Space" of Ideas
    00:10:04 Raising Seed from a16z in 3 Days
    00:17:23 The "Dark Period": Building Without Users
    00:22:23 Structuring Enterprise Design Partnerships
    00:28:48 The "2-Hour Bootcamp" Sales Strategy
    00:31:03 Why the Org Chart is Flat (15 Reports to CTO)
    00:34:02 Converting Pilots to Commercial Contracts
    00:41:07 The Moment of True Product Market Fit

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

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    45 mins
  • He raised $150M with $0 revenue. Then hit $1M ARR in 4 months. | Michel Tricot, Co-Founder of Airbyte
    Mar 2 2026

    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

    • How to hit $1M ARR in 4 months with a bare-bones product.
    • The "Magic Wand" framework for validating startup ideas.
    • Why you should sometimes optimize for Vanity Metrics.
    • How to raise $150M+ by solving the "build vs buy" dilemma.
    • The critical difference between Project Market Fit and Product Market Fit.

    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
    00:09:37 The Failed Marketing Product & COVID Pivot
    00:16:13 The "Magic Wand" Framework for Ideas
    00:20:52 Launching Open Source to Solve "Build vs Buy"
    00:24:39 Bootstrapping a Community on Reddit & Hacker News
    00:30:17 Why Too Many Users Broke the Team
    00:34:32 Project Market Fit vs. Product Market Fit
    00:36:16 Hitting $1M ARR in 4 Months
    00:37:53 Managing a Unicorn Valuation Without Revenue
    00:41:20 Advice for Early Stage Founders

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

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    43 mins
  • He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails
    Feb 26 2026

    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

    • How to survive 5 years of wandering before finding PMF.
    • Why he sold $790/month contracts to validate a pivot.
    • How to scale from $0 to $20M ARR with 100% outbound sales.

    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
    00:02:42 The First 5 Years of Wandering
    00:11:39 Being the "Black Sheep" of the Portfolio
    00:14:12 Identifying the FP&A Opportunity
    00:20:55 The Pivot: Selling $790/Month Contracts
    00:30:30 Scaling from $1M to $20M with Outbound
    00:33:18 Why the Mid-Market is Wide Open
    00:34:22 The Moment of True Product Market Fit

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

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    38 mins
  • His startup powers OpenAI's Voice Mode. Last month, they became a unicorn. | Russ d’Sa, Co-Founder of LiveKit
    Feb 23 2026

    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

    • How to secretly power ChatGPT’s voice mode.
    • Why you should build "boring" infrastructure instead of AI apps.
    • How to negotiate an acquihire when you have no leverage.
    • Why a "sell or die" threat from a tech giant was the best thing to happen.
    • How to pivot from a failed consumer app to a unicorn infrastructure play.

    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
    00:02:49 The OG YC Batch Experience
    00:07:08 How to Sell a Failing Startup
    00:15:51 The "Good Cop, Bad Cop" Investor Negotiation
    00:35:56 The First Voice AI Demo That Flopped
    00:38:29 The Secret Email from OpenAI
    00:43:47 How to Scale Stateful Voice Agents

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

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    55 mins
  • He pivoted at $1M ARR—then raised $120M. | Kevin Tian, Co-Founder of Doppel
    Feb 19 2026

    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

    • How to pivot from a bad market to a unicorn opportunity.
    • Why he sold a $5k/month contract with zero product.
    • How to raise a Series A from a16z during a pivot.
    • Why you never truly "find" Product Market Fit.
    • The danger of building for a niche market (and how to escape).

    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
    00:02:17 Meeting at Uber and the "Glass Eating" Phase
    00:07:21 The First Idea
    00:11:52 Selling the First $5k/Month Contract with No Product
    00:16:52 The Decision to Pivot at $1M ARR
    00:29:43 Network Selling to Enterprise Cybersecurity
    00:32:03 Raising Series A from a16z During a Pivot
    00:33:36 Why Product Market Fit is Not a One-Time Event
    00:35:10 Action Produces Insights

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

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    36 mins