He lost all 5 of his first deals—then built the next Looker and raised $250M. | Colin Zima, Co-Founder of Omni

He lost all 5 of his first deals—then built the next Looker and raised $250M. | Colin Zima, Co-Founder of Omni

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! [https://www.buzzsprout.com/1889238/fan_mail/new]

He fired almost everyone, kept 2 engineers—then grew 12x and raised a $30M Series A. | Rafael Broshi, Co-Founder of Notch

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! [https://www.buzzsprout.com/1889238/fan_mail/new]

He worked out of a police department for free for a year—then built a $6.8B company. | Ben Rudolph, Co-Founder of Peregrine

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! [https://www.buzzsprout.com/1889238/fan_mail/new]

1st-time solo founder does 90 interviews in 90 days—closes a $25M Series A 2 years in. | Damien Lewke, Founder of Nebulock

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! [https://www.buzzsprout.com/1889238/fan_mail/new]

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)

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! [https://www.buzzsprout.com/1889238/fan_mail/new]