Mato just raised pre-seed Read more
Podcast charts
Published by Mistral.vc
Every founder has 1 goal: find product-market fit. We interview the world's most successful startup founders on the 0 to 1 part of their journeys. We've had the founders of Reddit, Gusto, Rappi, Glean, Cohere, Huntress, ID.me and many more. We go deep with entrepreneurs & VCs to provide detailed examples you can steal. Our goal is to understand product-market fit better than anyone on the planet. Rated one of the world's top startup podcasts.
On the charts
Every published chart this podcast appears in, in the snapshot behind this page. Each one links to the chart it came off.
The Mato Topic Intelligence Platform does not report this podcast as charting in a published category in this snapshot.
From the feed
The latest episodes published to this podcast’s own RSS feed. Titles and descriptions are the publisher’s.
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 Intro 00:02:05 The Morgan Stanley Deal That Proved PMF 00:08:32 A 401k So Bad It Started a Company 00:10:23 Building V1 in a Regulated Industry 00:17:07 Turning Advisors Into a Sales Channel 00:23:57 Raising an A on $200K of Revenue 00:31:16 Too Boring for the Crypto Bull Market 00:38:45 Losing JP Morgan, Then Winning It Back 00:43:23 Never Regret Firing Too Soon Send 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 Intro 00:02:04 The Side Tool Everyone Wanted 00:04:26 $350K in Five Weeks 00:05:42 AI for Lawyers Before AI Worked 00:12:44 Stuck at $800K 00:13:43 Choosing Finance Over Legal 00:17:40 The 30 and 100 Rule 00:24:59 Selling the $10M Business 00:32:17 Building a Company Data Brain 00:40:01 Nine of Ten Bets Fail Send 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 Intro 00:02:11 Why Healthcare Has No Shortcuts 00:05:34 What Judi Health Actually Does 00:11:27 Opacity As A Business Strategy 00:15:12 Bootstrapping In A Regulated Market 00:21:50 Selling The First Risky Customers 00:27:15 Winning Bids When Rivals Look Free 00:33:37 Zero Marketing And A Service Moat 00:42:20 Hiring For Mission And A Players 00:52:35 Founder Advice On Focus And Discipline Send 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 Intro 00:02:23 $1.5M of Enterprise Revenue in One Month 00:04:22 Why Enterprises Couldn't Say No 00:06:04 What Endra Actually Does 00:08:27 Law School to CCTV Cameras 00:12:06 Recruiting Two Goldman Engineers 00:17:11 Finding Users in Reddit Threads 00:26:02 $4M, $20M, Then $50M From a16z 00:35:00 Spending $150K on Brand Before a Product 00:40:11 The Hiring Principles Manual Send 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 Intro 00:01:58 The Moment of True Product Market Fit 00:06:16 Losing All Five Deals and Doubling Down 00:10:43 Leaving Looker to Compete With Looker 00:17:39 Founding With $30M and Staying Stingy 00:22:09 A Hundred Demos Before the Flywheel 00:32:15 No Silver Bullet—Just Do More of Everything 00:38:32 The LinkedIn Social-Selling Playbook 00:46:07 Hiring the Best People You've Worked With Send 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 Intro 00:02:00 The Moment of True Product Market Fit 00:10:07 One Enterprise Deal or Ten 00:15:24 A Genius Idea Nobody Needed 00:24:33 Picking the Right Wave to Ride 00:34:37 Down to $2M, Firing Almost Everyone 00:41:48 Getting Enterprise to Take Your Call 00:48:07 The POCs That Aren't Real POCs Send 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 Intro 00:01:07 The Moment of True Product Market Fit 00:11:51 Getting a Police Department to Say Yes 00:16:45 Slow Growth and Word of Mouth 00:19:49 Forward-Deployed Engineers Before They Were Cool 00:27:34 Cracking Government Go-To-Market 00:34:08 Winning an RFP Written for Someone Else Send 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 Intro 00:01:20 The Moment of True Product Market Fit 00:11:33 Going Cold Turkey as a Solo Founder 00:23:07 90 Interviews in 90 Days 00:36:44 Raising $8.5M Off a Manifesto, Not a Deck 00:39:36 Every Design Partner Converted to Paid 00:44:00 Building a Repeatable POC Playbook 00:48:20 The Procurement Black Hole Send 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 ideas How 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 Intro 00:04:15 Inside Alphabet's Moonshot Factory 00:07:22 The Card Counters of Innovation 00:14:00 Learning per Dollar, Not Progress 00:23:04 Killing Ideas with Testable Hypotheses 00:26:34 Train the Monkey First 00:35:16 Kill Criteria: A Message to Your Future Self 00:41:59 The Moment of True Product Market Fit Send 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 Intro 00:01:56 The Moment of True Product Market Fit 00:09:46 Collapsing 6+ Tools Into One Platform 00:18:07 Leaving Brex to Start From Scratch 00:31:41 Landing H&R Block and Armanino 00:34:57 A 100% Pilot-to-Production Playbook 00:43:26 A 21-Person Company by Design 00:51:38 One Salary for Everyone Send 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 Intro 00:01:44 The Moment of True Product Market Fit 00:04:14 The #1 Driver of Word of Mouth 00:13:25 Why He Left Stripe to Build Render 00:23:48 Why AWS Would Never Build This 00:30:33 $10M ARR With No Marketing Spend 00:36:43 Engineers as the Support Team 00:42:19 Riding the AI Boom Send 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 Intro 00:01:39 The Moment of True Product Market Fit 00:03:33 Shutting Down a Small-Market Startup 00:07:44 Picking Fintech From Five Ideas 00:17:12 From Black Box to Full App 00:24:47 $1M ARR on Cold Email Alone 00:36:11 Why a "Seven" Is the Most Dangerous Hire 00:42:15 Compressing a $25M Series A Send me a message to let me know what you think!
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 How 2 months working as a paralegal beat years of customer discovery. How free Slack communities turned Fortune 500 HR managers into clients. Why earned media compounds like an asset while paid ads burn like an expense. Why impact is the best driver for starting startups. 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 Chapters 00:00:00 Intro 00:06:34 Walking Away from $50M ARR 00:13:12 Why Immigration Law Has AI Leverage 00:18:01 The AI-Native Law Firm Model 00:21:49 1,000 Intake Calls Before Building Anything 00:30:21 Turning Free Communities Into Buyers 00:37:20 Earned Media That Compounds Send me a message to let me know what you think!
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 Why validation only counts when dollars exchange hands. How a $20/month paid community turned into $1M in ARR. Why he refunded every customer and churned 100% of his revenue. Why founders must sell the first $2M themselves before hiring an AE. 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 00:00:00 Intro 00:08:37 From Upwork to Starting Amigo 00:13:30 $12K in Revenue Before Writing Code 00:23:24 Pitching 100 VCs in 10 Days 00:30:20 47 No's—Then FOMO Took Over 00:37:12 The $20/Month Community Behind the First $1M 00:45:47 Churning 100% of Revenue on Purpose 00:01:49 The Moment of True Product Market Fit Send me a message to let me know what you think!
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 Exactly how to use a cold outbound strategy to hit $1M ARR. Why getting on 56 flights last year to visit customers led to 186% NRR. How he closed a $25M Series A in just 6 days. 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 Chapters 00:00:00 Intro 00:06:10 The Pivot From Sales to Customer Support 00:12:54 Why Moving to SF Changed Everything 00:22:34 Cold Outbound to $1M ARR 00:32:47 Doorstepping Customers for 186% NRR 00:39:17 Closing a $25M Series A in 6 Days Send me a message to let me know what you think!
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. We get specific on early-stage fundraising benchmarks and why Series A now looks riskier than many people assume. Median Series A valuations have climbed close to 2x in a few years, while typical raises jumped from roughly $8M to $10M to $13M to $15M. That changes everything: ownership targets, follow-on costs, and the outcome math that pushes investors (and founders) toward “decacorn-plus” expectations. If you are pitching $100M ARR as the endgame, you may already be behind. Then we zoom out to the forces shaping who wins: Bay Area gravity, a real valuation gap versus other hubs, and practical tactics like visiting the Bay to capture network effects without uprooting your life. We also dig into defensibility in AI application startups, where building is faster but competition is fiercer, plus the rise of smaller teams and solo founders, and what that means for hiring, equity, and motivation on early teams. Chapters 00:00:00 LLM Hype And Bubble Warning 00:02:13 Five Stars Then We Begin 00:03:02 Seed Prices Spike In AI Infra 00:07:10 2026 Benchmarks For Pre-Seed To A 00:09:36 Series A Doubles And Exit Math 00:12:54 Bay Area Gravity And Valuation Gap 00:18:22 Defensibility Gets Harder In AI Apps 00:23:22 Smaller Teams Solo Founders Talent Shifts 00:35:20 VC Fund Shakeout And Final Share Ask Send me a message to let me know what you think!
I meet 1,000+ founders every year. Most are bad at fundraising. I also interview 100+ of the world's best founders on my podcast each year. Most are incredible at fundraising. One raised $14M in 17 days. another was 3x oversubscribed on a $3M round. another closed a seed in hours from a single X post. All are first-time, unproven founders. They don't waste time becoming "friends" with VCs. They have a business to build. They treat fundraising for what it is: a process where you manufacture FOMO as fast as possible, take the money, and move on. This video breaks down the 4 steps the best fundraisers use to raise fast. The same 4 steps taught at YC and 500 Startups (where i went). The same 4 steps you can run on thousands of VCs worldwide to close $2-3M in weeks not months. Why You Should Listen Why you need to reach out to 50 VCs on the same day just to end up with three term sheets. How to engineer intro blurbs that make VCs feel like they're already late to the game. Why setting fake deadlines is the fastest way to destroy all your credibility with investors. How one founder raised $3M in five weeks by starting with a $1.5M target and driving FOMO. 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 00:00:00 Intro 00:01:30 Step 1: Build a List of 50 Qualified VCs 00:06:00 Step 2: Engineer the Intros 00:14:00 Step 3: Compress the Timeline 00:20:00 Step 4: Manufacture FOMO 00:26:00 Three Rules to Never Break Send me a message to let me know what you think!
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!
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!
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!
Ranking source
Apple Podcasts rankings via the Mato Topic Intelligence Platform.
Observed September 18, 2026. Cached outside the daily freshness window; the positions keep the date they were taken on.
Apple and Apple Podcasts are trademarks of Apple Inc., registered in the U.S. and other countries.
Pairs with
Bring this source into Mato to read its transferable patterns, then turn them into an original show for your own audience.