Season 3

Paul built a startup that was acquired for $2.2B. He worked on AI at Uber and Oculus. But when a farmer told him about some of the problems he was facing, he quit and went all-in on farming. He built a robot that attaches to ...

Elon Musk single-handedly took on the entire automotive industry. No one, including me, thought he would succeed. But he's built an $800B company. Whether sales are slowing down misses the mark: the punchline is it took well ...

Last month, Ashby raised a $30M Series C. Ashby is used by customers like Notion, Ramp and Sequoia. Benji built Ashby as an end-to-end Applicant Tracking System (ATS) that would replace several point solutions. He had to buil...

AI startups don’t necessarily have to beat incumbents. Some will start entirely new markets instead. Like Canva to Photoshop, Shopify to Amazon or Pickleball to Tennis, many of these won’t even have to compete. They create 10...

"I was technically homeless at the time. I was sleeping on my buddy's couch. I had declined $250,000/ year at McKinsey... I had no idea what I was doing." Now, Blake has $150M in ARR, growing 30% per year, with 80% gross margins. He's raised $400M and his startup ID.me is worth over $1B. This is th…

Every startup needs to compete with incumbents. But it's different with AI. AI startups need to create websites or apps from scratch and drive traffic. Incumbents can just add AI as a feature. They have distribution built in. AI is not like previous tech revolutions. Unlike mobile, the internet, or…

Andrew spoke with 120+ VCs to raise a $1.5M pre-seed round. He closed $2.7M and had demand for many millions more. He devoted 90% of his time to fundraising, but only took weeks from the first meetings to close. 99% of founde...

Zoom was THE work-from-home stock. It's down 90% from peak. The same hype that fuelled work-from-home stocks is now fuelling AI. What happened to Zoom will happen to many AI companies. AI startups today need to carefully position against foundational models and incumbents. Here's how to think throu…

Chris shares the story of how he grew Refine Labs to $22M ARR, what he did to grow so fast, and also why he regrets spending so much on growth instead of focusing on profitability. He goes exceptionally deep on sales and mark...

Sam Altman is playing chess not checkers. He partnered with Microsoft. He partnered with Apple. He grew to $3B in ARR in 2 years. Hate him or love him, he's a strategic genius. You'll recognize a pattern: Sam has an idea, pos...

We interview Chris Slow the CTO and Founding Engineer at Reddit. Reddit is now a ~$10B company, with nearly $1B in revenue. Their 1B+ monthly active users are so powerful they can move markets. This is the story of how it al...

Wardah was a PhD graduate working at a biomedical imaging startup. But all it took was two different dentists giving her two totally different diagnoses for her to quit her full-time job. She was unemployed with no idea what ...

Dane was the CEO of Squarespace from 2007 to 2011. He grew the company from ~$2M in revenue to ~$15M. He's a multi-time founder with multiple exits. His current startup, Odeko, raised $227M. He takes us through his long journey as a founder of multiple companies and shares the key startup lessons h…

His first startup was a cool idea: Uber for Valet Parking. Investors loved it. But the unit economics didn't work out. So he had to pivot. He ended up selling it, but decided to do things differently the second time around. “...

His travel startup crashed 90% overnight. Here’s how he used AI to grow past $2M/year—to $2M a month: For a while, Andrew was crushing it. Accelerator -> $750K pre-seed -> $2M ARR -> $2.5M seed round. Then COVID hit. He was selling to events like CES, SXSW, etc. Revenue dropped from $160K/…

Poojan is a multi-time successful founder. He raised $60M for his first startup and exited. He just raised a $75M Series D at his current startup. But it wasn't always easy. - In his first startup, he had to hover beside conf...

Arvind founded 2 billion-dollar startups—by doing everything lean startup tells you not to do. - He didn’t focus on launching an MVP. - He ignored early market feedback. - He didn’t charge beta users anything— for 2 years. A...

Snapchat got 0 downloads the day it launched. 5 months in, it had only 127 users. Today Snapchat is an $18B company with 400 million daily active users. Evan Spiegel noticed what even Zuck missed: daily communication is meant...

If you feel like the ‘unicorn or bust’ playbook isn’t for you, then this episode definitely will be. Rand Fishkin is a multi-time founder and published author of Lost and Founder. He founded Moz, raised $29M in VC, grew to $5...

While Voice AI is all the rage now, it wasn't a hot sector in 2017. After Dylan graduated from YC, VCs rejected him. He couldn't raise a round. They all assumed Google would do it. So he raised what he could from angels and made it work for the next 3 years. He's now built the world's most accurate…

Andrew is the founder/CEO of Enable. And he is riding a rocket ship: 2020: $17M Series A 2021: $45M Series B 2022: $94M Series C A few months ago he raised $120M at a $1B valuation. But it took him five years from the time he started Enable in 2015 until he was able to raise his first round in 2020…

Alex started Apt2B in 2010. He sold couches online before IKEA did. It took him over 3 years to make as much money as he used to as a furniture salesperson. But it paid off. After growing the business to $6M in revenue, he so...

Every founder wants to build the next $1B+ company. So it’s normal to get inspired by what companies like Apple, Shopify and Microsoft do. But it’s also a huge mistake. In this episode, we look at what Shopfiy, Fullscript and...

Spellbook is ChatGPT for lawyers. They've raised $30M in the last 6 months. They now have over 2,000 law firms as customers. But it wasn't a straight line-- it took Scott 6 years to get here. For the first 5 years, Scott worked on a legal tech platform called Rally. During that time, Scott along wi…