Coinbase's ex-CPO bet on AI agents before ChatGPT—now he's closing 7-figure Fortune 500 deals. | Surojit Chatterjee, Founder of Ema

Coinbase's ex-CPO bet on AI agents before ChatGPT—now he's closing 7-figure Fortune 500 deals. | Surojit Chatterjee, Founder of Ema

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 * Why true PMF is when your average salesperson can sell the product without you in the room. * How a single Hitachi deployment unlocked credibility for every Fortune 500 deal that followed. * Why a cold email—not a warm intro—turned into Ema's largest partner today. * How partnering with PwC and KPMG became a faster wedge into the C-suite than any conference. 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 Chapters * 00:00:00 Intro * 00:02:00 Hitachi Was the PMF Moment * 00:04:10 What Ema Actually Does * 00:11:48 From Coinbase to a Pre-ChatGPT Bet * 00:28:48 The Cold Email That Won a Top Partner * 00:30:52 Small Dinners Beat Massive Conferences * 00:36:11 The Moment of True Product Market Fit Send me a message to let me know what you think! [https://www.buzzsprout.com/1889238/fan_mail/new]

How this 1st-time founder went from closing customers for $500 a month to $300,000 a year. | Sean McCarthy, Founder & CEO of BackOps

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 * Why talking to 85 customers before writing a line of code is worth more than anything. * How an eight-minute screen recording replaced months of SOP-writing delays. * Why "what are your problems?" fails in enterprise and a pointed use case wins eight out of ten times. * How to structure pilots that auto-convert so you never end up in post-pilot purgatory. 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 Chapters * 00:00:00 Intro * 00:02:24 Beating a Giant on 5% Odds * 00:09:25 Eighty-Five Warehouse Interviews * 00:16:33 V1: A Slack Bot for Reshipping * 00:22:05 Pausing Sales to Rebuild for Enterprise * 00:34:49 The Scrappy Enterprise Sales Playbook * 00:48:23 Two Intentional Wow Moments in Every Demo * 00:53:40 The Moment of True Product Market Fit Send me a message to let me know what you think! [https://www.buzzsprout.com/1889238/fan_mail/new]

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

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 * Why picking the highest-taste customer is more important than picking the biggest market. * How proof-point-driven outbound gets you past the "nobody's heard of you" problem. * Why the founder-to-seller handoff is a forcing function for focus—and when to make it. * How a consultative, education-led sale converts almost every pilot to annual contract. 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 Chapters * 00:00:00 Intro * 00:03:06 Two Years in the Idea Maze * 00:06:51 Why He Picked Marketers Over Everyone Else * 00:14:36 What Best-in-Class Content Looks Like Now * 00:25:42 From $1M to $13M ARR * 00:28:29 Building a Repeatable Sales Machine * 00:36:15 Competing in the Hottest AI Category * 00:38:44 The Moment of True Product Market Fit Send me a message to let me know what you think! [https://www.buzzsprout.com/1889238/fan_mail/new]

180 VCs rejected him—then a $60K billboard got him to $2M ARR in 4 months. | Isaiah Granet, CEO of Bland AI

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 * Why 180 VCs saying your market won't exist is actually a bullish signal. * How two billboards and a wave of micro-influencers generated a billion impressions. * Why firing half your customers right after raising your Series A can save your roadmap. * How internal newsletters and org-chart mapping win six-figure enterprise deals. 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 Chapters * 00:00:00 Intro * 00:02:34 A Typhoon Replaces an Entire Call Center * 00:11:52 The YC Pivot and 180 Rejections * 00:19:05 Betting the Company on In-House AI * 00:24:11 The Billion-Impression Billboard Campaign * 00:34:49 Firing 50% of Customers After Raising $20M * 00:38:43 The Enterprise Sales Playbook * 00:50:52 The Moment of True Product Market Fit Send me a message to let me know what you think! [https://www.buzzsprout.com/1889238/fan_mail/new]

She bet on a consumer app when every VC wanted B2B—then grew to $10M ARR. | Anada Lakra, Founder of BoldVoice

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 * Why building a consumer app in the 2020s is not as crazy as VCs think. * How Reddit threads and guerrilla marketing drove BoldVoice's first thousand users. * Why defaulting to annual pricing gave her instant CAC payback. * How she grew from zero to $1M ARR and raised a $21M Series A. 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 Chapters * 00:00:00 Intro * 00:02:14 The Accent Problem Nobody Was Solving * 00:11:49 Getting Into YC with No Revenue * 00:22:48 Shipping V1 from a Dorm Room * 00:29:31 Guerrilla Growth on Reddit and Facebook * 00:36:05 Cracking the YouTube Influencer Playbook * 00:48:09 Why Annual Pricing Changed Everything * 00:50:47 The Moment of True Product Market Fit Send me a message to let me know what you think! [https://www.buzzsprout.com/1889238/fan_mail/new]