Episodes

In 2005 most people didn't even have cellphones yet. Those who did used flip phones. That's when Noah started Olo, a webapp to let people pre-order coffee from nearby shops. Users had to login on web, add a credit card, create pre-made orders and then send a text to a preset number when they wanted…

Frankie lost $10K in a crypto transaction—so he started Staging Labs to find a way to help others prevent crypto scams. He was head of an incubator called Entrepreneurship First and had seen dozens and dozens of founders buil...

Hussein's travel startup was doing $10s of millions when COVID hit. His revenue didn't just go to zero, it went negative. There were more customers asking for refunds than new sales. He was 4 months from running out of money. He ended up making a complete pivot, he changed the company's name from S…

When Amplitude launched Mixpanel was the big game in town. They were first to market, had raised more money, and had a well-known brand. VCs passed on Amplitude because it seemed like just another Mixpanel. Today, Amplitude i...

This first time founder just raised a $38 million Series A. The crazy part is that for all of 2021, 2022, 2023, he had almost no revenue. He spent all that time building and pivoting. Finally he launched in 2024—and it blew u...

Carta just released their report for Q4 2024. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rat...

Alon was a hacker for the Israeli Defence Forces' cyber department. There he saw the most advanced methods used in cyber warfare. So when he left, he started IntSights-- a company that helped enterprises defend themselves from cyber attacks. He was a first-time founder who didn't even know the word…

Ned had a chance to run Robinhood Asia but he turned it down. Instead, he launched a competitive product. He decided to go B2B and sell to banks and other financial institutions. He locked down a $400K revenue sale before wri...

Jason built a data center company in the 2013. When he exited in 2019, it was the third-largest exit in Canada that year. He'd sold his previous startup and invested 100% of his capital into ROOT. He grew to 10s of millions a...

Pablo is the first guest that has the same name as me-- so you KNOW this episode will be great. Pablo hustled for months just to get to $70K in ARR. He got rejected from YC, re-applied, and finally got in. But after months in...

Alex sold his last IoT startup for over $200M to Samsung. He felt the needed to build something much bigger, so he started BrightAI. The goal was to use AI and IoT to solve big problems for enterprises. A few years later, he ...

Nathan has interviewed 100s of founders on how they raised their first few rounds. In this interview, we go through some of the most compelling stories he's heard. We go through step-by-step what you should do to raise a roun...

A few years into building Flashfood, Josh was $35K in debt with no money in his account. Just a few months earlier, he'd lost both the pilot customers he'd worked so hard to lock in. He'd worked for months to land them and ha...

Darius started an EdTech startup to help users of online courses collaborate with each other. It blew up during COVID when everyone felt isolated. It gained thousands of users. They were engaged. They came back to use the pla...

Zach was burned out after a decade of working at top roles in Coinbase, Square and Brex. He quit with no startup idea-- and then, he went right back in. Given their background, Zach and his co-founder quickly raised an $8M se...

We took examples from the last 100 episodes and built a clear, 5 step path to finding product market fit: 1.Before Startup Mode, There’s Research Mode —> Become an expert to find problems worth solving. 2.Only the Insanely Fo...

Gusto is a $9.5B startup that does $500M ARR. Josh built an absolute monster of a company-- and it all started with payroll software for SMBs. Not just that, he started by servicing only new tech startups that were based in C...

We go through the top 5 product-market fit lessons I've learned from speaking to well over 100+ founders on this show over the last 3 years. These are the top 5 things you should keep top of mind going into 2025. Why you should listen: Small teams outperform larger ones in early stages.Paying emplo…

Tolga stumbled upon a problem in the security monitoring space. Motion cameras generated way too many false alerts. So he decided to solve it using AI. He raised over a million dollars and got several customers. But he always...

There are a few things harder when building startups than getting your first few customers. When you're on a standstill, getting momentum is incredibly hard. Going from zero to one takes an incredible amount of effort—you have absolutely no credibility, no proof points. So to help you out I went th…

Ankit left his job as a VC to launch a Voice AI platform—back in 2018! It wasn't the voice AI of today. The first demo sounded like a robot. But still, he convinced large enterprise customers in the healthcare space to try it out. He found a highly manual, call intensive workflow in the back office…

Marty and his co-founders lived full-time in their office for several months. They worked on their startup 24/7. To come up with the idea, they messaged 120 potential customers every day for 3 months. Originally, when they pi...

I interviewed Martin on the keynote stage at the SaaS North conference. Here is the audio version. Martin built Applyboard into a $4B unicorn doing $100M+ in ARR. He left and started a new startup called Passage— and raised a...

Jon started a sports betting app 4 years ago-- now he does $150M in revenue and $1B in betting volume. AND he's profitable. In his first year alone , he did $10 million in revenue. He took a year to build the app and as soon ...