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

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 ListenWhy 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 softwareChapters00:00:00 Intro00:02:00 Hitachi Was the PMF Moment00:04:10 What Ema Actually Does00:11:48 From Coinbase to a Pre-ChatGPT Bet00:28:48 The Cold Email That Won a Top Partner00:30:52 Small Dinners Beat Massive Conferences00:36:11 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenWhy 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 AIChapters00:00:00 Intro00:02:24 Beating a Giant on 5% Odds00:09:25 Eighty-Five Warehouse Interviews00:16:33 V1: A Slack Bot for Reshipping00:22:05 Pausing Sales to Rebuild for Enterprise00:34:49 The Scrappy Enterprise Sales Playbook00:48:23 Two Intentional Wow Moments in Every Demo00:53:40 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenWhy 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, GreylockChapters00:00:00 Intro00:03:06 Two Years in the Idea Maze00:06:51 Why He Picked Marketers Over Everyone Else00:14:36 What Best-in-Class Content Looks Like Now00:25:42 From $1M to $13M ARR00:28:29 Building a Repeatable Sales Machine00:36:15 Competing in the Hottest AI Category00:38:44 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenWhy 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 GranetChapters00:00:00 Intro00:02:34 A Typhoon Replaces an Entire Call Center00:11:52 The YC Pivot and 180 Rejections00:19:05 Betting the Company on In-House AI00:24:11 The Billion-Impression Billboard Campaign00:34:49 Firing 50% of Customers After Raising $20M00:38:43 The Enterprise Sales Playbook00:50:52 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenWhy 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, BoldVoiceChapters00:00:00 Intro00:02:14 The Accent Problem Nobody Was Solving00:11:49 Getting Into YC with No Revenue00:22:48 Shipping V1 from a Dorm Room00:29:31 Guerrilla Growth on Reddit and Facebook00:36:05 Cracking the YouTube Influencer Playbook00:48:09 Why Annual Pricing Changed Everything00:50:47 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenWhy ignoring a customer's "no" can be the best sales move you make.How flying to see buyers weekly became the number one growth driver.Why the gap between A and A-plus talent is worth blowing your budget for.How Protege went from $1M to $30M GMV in a single year.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, ProtegeChapters00:00:00 Intro00:03:01 Building the First Data Network00:06:12 Why In-Person Sales Changed Everything00:16:08 Going to Market with No Pipeline00:21:07 Ignoring the Lab's No00:27:40 From $1M to $30M in One Year00:34:55 Why A-Plus Talent Is Worth It00:38:28 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenWhy 40% of your marketing traffic is wasted the moment it hits your site.Why the future of e-commerce is a showdown between AI seller agents and AI buyer agents.How he signed 11 enterprise brands in under a year with a free POC and rev-share pricing.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 KuruvillaChapters00:00:00 Intro00:01:25 Amazon VP to Basement Startup00:06:23 Why AI Changes E-Commerce00:09:34 The 40% Traffic Gap00:17:43 AI Merchandising in Real Time00:23:17 Raising $50M for the Seller Agent00:33:12 Signing 11 Enterprise Brands00:37:17 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenWhy 22 VC partner meetings said no—and how one change fixed it overnight.How she used an AI clone of herself to close a Series A in 3 days.Why starting enterprise-first beats moving upmarket.Why outbound AI email is a race to the bottom and what to build instead.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 retentionChapters00:00:00 Intro00:05:58 22 VC Rejections—Until She Found the Right Co-Founders00:08:49 Why She Always Starts Enterprise-First00:22:00 Five Years Off—Then the AI Wave Hit00:27:32 Why AISDRs Are a Race to the Bottom00:43:23 Using Her AI Clone to Raise the Series A00:49:52 The Moment of True Product Market FitSend me a message to let me know what you think!

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 ListenHow to pre-sell a $65k enterprise contract before writing code.The "Closing Discount" hack to generate 5 referrals from every new customer.Why finding "Message Market Fit" is more important than your ICP.How to spot and avoid early-stage startup "vultures".Why scaling a B2B sales motion requires hiring misfits over pedigree.00:00:00 Intro00:01:41 Leaving a $30M Startup to Build with AI00:08:06 Finding Message Market Fit Through Cold Calling00:20:07 Pre-Selling a $65k Contract with Wireframes00:27:51 The Voice AI "Aha" Moment00:33:07 The Closing Discount Referral Hack00:37:18 The Brutal Reality of B2B Sales00:42:19 Hitting $1M ARR and Pacing for $50M00:45:05 Why Product Market Fit is Never Truly FoundSend me a message to let me know what you think!

DescriptionBhaskar 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 ListenWhy selling to developers is operating on hard mode.How one-day POCs became the killer enterprise sales weapon.Why freemium disrupted an industry that required weeks of professional services to get started.How they grew from $2M to $12M in revenue in just one year post launch.Keywords startup podcast, startup podcast for founders, product market fit, AppDynamics, application monitoring, enterprise SaaS, B2B sales, finding pmf, freemium strategy, Cisco acquisition, production POCChapters00:00:00 Intro00:11:33 Choosing the ICP00:20:37 Landing Netflix with Freemium00:28:44 Growing from $2M to $12M in Year Two00:30:10 The Free Download Strategy That Generated 60% of Leads00:32:04 Days from the NASDAQ Bell—Then Cisco Offered $3.7B00:41:28 The Moment of True Product Market FitSend me a message to let me know what you think!