Episodes
This 3x founder hit $1M ARR in 5 months. Here's his playbook. | Roy M…
Roy is a three-time founder who has cracked the code on enterprise AI. After selling his first company and realizing his second idea was too slow, he pivoted to solving a massive problem: customer service automation. In this ...
He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Rya…
Ryan was a successful lawyer with a massive problem. He couldn't find a task management tool that worked for his firm, so he built one himself. He thought he'd solved the problem, but for 8 agonizing months, he couldn't sell a single subscription. In this episode, Ryan breaks down the gritty realit…
He ignored users for a year. Then landed a $1M contract. | Sam Jones,…
Sam spent years at the Air Force and Palantir before deciding to build Method Security. Instead of launching an MVP and iterating with customers, he did the opposite: he shut out the world and built in the dark for a year bas...
He raised $150M with $0 revenue. Then hit $1M ARR in 4 months. | Mich…
Michel raised $185M and achieved a unicorn valuation before he fully cracked monetization. How? By building a community so strong it broke his engineering team. In this episode, Michel breaks down the chaotic journey from a f...
He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi G…
Didi spent five years building a product that no one really wanted. He raised $10 million, tried endless pivots, and was known as the "black sheep" of his investors' portfolio. Then, with his back against the wall, he made on...
His startup powers OpenAI's Voice Mode. Last month, they became a uni…
Russ was running a moderately successful live streaming startup. Then he got a terrifying offer from a tech giant: sell to us for cheap, or we'll crush you. He had no leverage. He was about to fold. Then he got an email from ...
He pivoted at $1M ARR—then raised $120M. | Kevin Tian, Co-Founder of …
Kevin was building a successful startup in the NFT space. They'd hit $1M ARR. But he looked at the market and realized it wasn't big enough. So he made the terrifying choice to pivot the entire company into cybersecurity. In this episode, Kevin breaks down how he navigated that transition without k…
He sold his first startup for $100M. Then raised $250M in 18 months. …
Dileep sold his first company for over $100M. For his second act, he didn't just want another win; he wanted to solve a problem that banks refused to touch: global business banking. In this episode, Dileep breaks down how Jeeves scaled to $7M ARR in just over a year by doing things that "don't scal…
He sold his first 2 startups. His 3rd grew to $1M ARR in 3 months. | …
Chaz has founded 3 companies. The first sold for over $40M. The second sold to GoPuff for even more. Now, he’s on his third act with Model ML, having just raised $75M Series A <2 years in. In this episode, Chaz breaks down th...
He fired all his customers. Then built a $1B startup in 2 years. | Ja…
Jay was running a respectable AI startup with $3M ARR. But he knew it wasn't a venture-scale rocket ship. So, he decided to fire all his customers, pivot the entire company, and bet everything on a new vertical: legal AI for plaintiff attorneys. Eve went from zero to unicorn status in under two yea…
He wrote the book on Account Based Marketing. Here are his GTM secret…
Bassem took Briq from a failed data idea to a Series B leader in construction financial automation.But the path wasn't linear. In this episode, Bassem reveals how he pivoted to RPA bots, why he killed a high-growth fintech pr...
He got rejected from YC—then grew to $1.8B in under 2 years. | Max Ju…
Max went from a YC rejection to building a $1.8B company in less than two years. His company, Legora, is the fastest YC-backed company to become a unicorn in history. His path to insane growth was not standard: after raising ...
He sold dog food from his condo. Now he does $100M+ a year. | Russell…
Russell went from working in private equity to hand-delivering dog food on the NYC subway at 5 a.m. He didn't start with a VC check; he started with a studio apartment kitchen and a belief that dog food was broken. In this ep...
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 ...