Episodes
He made 100 cold calls a day. Now his startup is worth $600M. | Harma…
Harman went from cold-calling hotels 100 times a day to building the category-defining guest management platform for the hospitality industry. Canary built a $600M company by first solving one tiny, annoying problem: paper cr...
He got 100k signups in 30 days. They all churned. 2 years later, he h…
In this episode, Rich breaks down the wild story of Fathom's launch. He reveals how they secured a prime spot on the Zoom Marketplace and generated 100,000 signups in 30 days—only to realize 99.9% of them were useless. He discusses the pivot to monetization when the market crashed, how to design a …
He grew his startup to $150M ARR & an IPO. Now he's back for the AI w…
Bob is a serial entrepreneur who founded MobileIron, grew it to $150M in revenue, and took it public. Now, he's back with his fourth startup, BlueRock, tackling the next massive wave: agentic AI security. In this episode, Bob...
How his AI-enabled Services startup hit $1M ARR in just 3 months. | S…
In less than 12 months, Shahar went from an idea to a $30M Series A and a team of 40. He didn't sell another AI tool—he built an AI-first service that replaced expensive human consultants in the massive pen-testing market. In this episode, Shahar breaks down the "Service-as-Software" playbook that …
He hit $1M ARR with just 2 people. 2 years later, he's worth $1.5B. |…
Ashwin built a $1.5B company in two years. He didn't do it with a massive team or a complex 5-year roadmap. He did it by ignoring "strategy" and talking to 100+ buyers until he found a problem so painful they would pay six figures for a solution that didn't fully exist yet. In this episode, Ashwin …
His 1st startup failed. His 2nd became a unicorn in just 18 months. |…
Jake founded Serval in April 2024— by Dec 2025 he'd raised a $75M Series B from Sequoia at a $1B valuation. He didn't look for a "wedge" or a "niche." He looked at ServiceNow—a $160B, 20+ year-old incumbent that everyone IT team relies on—and rebuilt it from the ground up in a YEAR. In this episode…
It took him 4 years to launch—then he hit $1M ARR in 30 days. | Siqi …
Siqi was the CEO of a hot startup doing $20M a year. Then COVID hit. Overnight, revenue went to zero. He had to lay off 95% of his staff. In the chaos of trying to save the company using broken spreadsheets, he found his next...
Solo Episode: B2B SaaS is dead. Here's what the best AI founders are …
The startup game has completely changed. If you are still building with the 2018-2022 B2B SaaS playbook, you are already behind. In this episode, we break down exactly how the GenAI shift has altered value creation, competiti...
He got rejected by 60 VCs, burned all his savings—then grew to $100M …
For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3. Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savi...
He killed a $100K ARR product & pivoted—then raised $375M. | Viraj Pa…
They were building a Segment competitor. It was working—customers were paying. But every sales call, prospects kept asking about the backend tech instead of the product. So they killed the roadmap and pivoted. It took them 18...
Solo Episode: The Five Steps to Product Market Fit
For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 2. Here are the key lessons from the past 60 episodes that we've released to date. Each of the 5 steps to Product ...
He killed a viral app with 50k users. 2 years later, he hit $10M ARR …
David had a consumer app with 50,000 users and viral traction—and he shut it down. The retention metrics weren't as good as what he'd seen at Snapchat. That difficult decision cleared the path for Juicebox, AI for recruiting ...
Her VCs said she killed the company. 6 years later, it's worth $1.3B.…
Jennifer went from VC to founder and immediately broke every rule in the book. When she pivoted Scribe from an automation tool to a documentation platform, her investors told her she had just killed the company. She ignored t...
He exited to Snap for $166M— built an AI video startup, then raised $…
Alex built the original Snapchat filters-- and sold his company to Snap for $166M. Then he left to start Higgsfield. The company just raised a $50M Series A to help brands create AI-generated video ads at scale. We go deep on...
How his AI-first services company grew $0 to $40M ARR in one year. | …
Eric spent 30 years in cybersecurity. Built and sold an MSSP to private equity for hundreds of millions. Then he started Tenex and hit $43 million in revenue in ONE YEAR. This isn't theory. This is a founder who's done it mul...
Q3 2025 w/Carta: What you need to raise a Series A. | Peter Walker, H…
Carta's Peter Walker is back with the freshest data on what's actually happening at the early stage—and it's not what you're reading on X. While headlines scream about record-breaking rounds, the reality on the ground tells a different story. Seed deals are down. Time between rounds is stretching. …
He added AI to parking lots—then raised $3.5B. | Alex Israel, Founder…
Alex and his co-founders spent 2018 pitching parking lot owners on computer vision tech. Every meeting ended the same way: "Cute startup, come back in 30 years." So they did something else—they bought the parking operators an...
He left a $2B ARR company to build AI agents—then hit $1M ARR in < 6 …
Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data inste...
He tested his idea in one weekend—then raised $120M. | Wayne Slavin, …
Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insur...
At 21 he made his 1st million. At 23, he grew his startup to $8M ARR …
Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months. His secret? Insane distribution. His formula is to ignore...
He walked away from $5M ARR—then built a $50M company. | Russ Fradin,…
Russ has started and sold multiple companies over 30 years, but his Dynamic Signal journey will change how you think about product-market fit. They had $5M ARR selling influencer marketing software. Then Russ told investors t...
He made 2 key changes —then grew to $100M ARR in 2 years & exited for…
Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up. Then he made two changes—and scaled to $100M in revenue in 2 ...
He built a $20B public company, left—then raised a $100M Series A. | …
Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A. This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why ...
He built a new database in his bedroom—now he powers Cursor, Notion a…
Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it. When Cursor emailed abou...