Episodes
He hit $40M ARR, exited for over $100M—& raised only $1.5M. Here's ho…
In 2014, Ian launched a simple product: it let social media marketers buffer Instagram posts. It was originally a hackathon project. But it quickly gained users. So he and his co-founders went all in. They raised just one sma...
He raised $16M, hit $1M ARR—& failed. Here are the top 3 lessons he l…
David's startup failed. But he had everything going for him: a solid thesis, $16M in funding across 3 rounds, $1.5M in ARR. At a high-level it seemed like everything was going the right way. And yet, it didn't work out. This is what happens to 95% of startups. On thhis show, we mainly speak with th…
He sold his 1st startup for 8 figures, grew his 2nd to $3M in a year—…
Justin sold his first bootstrapped startup for over $10M. He raised $2M out of the gate for his second and then grew from $250K to $3M ARR in one year. He raised $40M in total, including a Series B from Bessemer. And yet, jus...
He raised $1.5M, hit $400K ARR in 9 months— but had to Exit Early. He…
Rob founded Outpoint in 2020 to help marketers optimize their ad spend. He was a growth marketer and his founder a data scientist. He had team-market fit, a solid thesis, and paying customers. But when the recession hit and a...
His startup Cameo was a unicorn—until it crashed 90%. Here's how he w…
Cameo is one of the best-known recent consumer startups. You've either used it or know someone who's used it to get famous people to create personalized videos. And, for a while, they were a total rocket ship. Year 1: $300K GMV Year 2: $4M Year 3: $20M Year 4: $100M They were backed by Jeremy Liew,…
VC funding is not popping back. THIS is the new normal—here's how to …
Q3 startup data just dropped. We chat with Peter Walker, Head of Insights at Carta about valuations at pre-seed, seed and Series A. Why the current fundraising environment is the new normal and not about to get much better. W...
His robotics startup raised $400M, his VC fund over $4B—& he ran both…
Lior is the Elon Musk of VC. In just 8 years, his venture fund went from 0 to $4B under management. And while doing that, he founded Bright Machines, which to date has raised over $400M. He's both the CEO of Bright Machines a...
This 1st-time founder raised $4M, kept the team to 5 people—& just ra…
Parker quit his job as VP Finance at a late-stage startup in mid 2021. He raised $4M out of the gate because, well, it was 2021. But he didn't ramp up sales, he didn't hire 15 developers. He kept the team to 5 people for the ...
In 2004, they "almost bankrupted themselves". In 2024, they hit $500M…
Mike started selling SaaS before SaaS was a thing. PointClickCare is the Salesforce of healthcare. For the first 7 years, they raised just $600K from friends and family. With that funding, they grew to $50M in ARR. Through th...
The top 3 reasons why Zuck is killing Apple in the Mixed Reality race.
Apple sold only 370,000 VisionPro headsets-- much fewer than it expected. Meanwhile, Meta Ray-Bans are the top-selling product in 60% of Ray-Ban stores. The outcome of their AR/VR products couldn't be more different, even tho...
His influencer marketplace hit $150M in revenue—& just exited for $50…
Piotr met his co-founders at a party in Coachella. He built them an app for influencers to post online. That simple idea evolved into one of the world's first influencer marketplaces. While so many other tried and failed, Pio...
Your odds of raising a Series A just dropped from 30% to 15%—here's w…
New Carta data shows that 30% of seed-stage startups used to raise a Series A within 2 years of their seed. Now, only 15% do. The bar for Series As is as high as it's ever been. And the number of seed extensions that I see is...
His 1st startup failed—but his 2nd one hit $100M ARR & a $1.6B valuat…
Liran quit a cozy job at IBM to launch Fusic, a TikTok-like app back in 2011. He raised over $10M, acquired tens of thousands of users, and failed. So he went back to what he knew: deep tech and enterprise. He launched WEKA i...
He quit Google with no startup idea, raised $50M from Sequoia with no…
This episode is going to piss you off. Most founders struggle to raise their first few million. Many have to bootstrap for years. Even once there's revenue, many get rejected because they're "too early". Dan had dozens of VCs...
He founded a banking app for kids 10 years ago, grew to 2M customers …
It was “really slow in the first couple of years...really, really slow.” GoHenry was an app and debit card for kids to help parents teach their kids about money. Dean started over a decade ago in 2012, when mobile was just tr...
1st-time AI founder grows from $0 to $1.3M ARR in 8 months. Here's ex…
Jaspar graduated YC & closed a $11.5M seed round this week. He launched Artisan just 8 months ago. And this is the first venture-backed startup he's ever ran. He started with product-led-growth but struggled. In May, he moved...
He launched an Uber competitor with just $3,000—& grew to $20M in rev…
Cody started a ride-share business in 2017 with no capital. He focused exclusively on small towns (population <100K) where Uber/Lyft weren't available. I know as a VC I would've passed if he'd pitched me when he started—and I...
The ONLY guaranteed way to attract & retain A-players.
I tried to pay my employees as little as possible. I thought I was being resourceful—& it seemed to work. Until it totally backfired. I learned my lesson the hard way. No founder wants to hire B-level or C-level talent. Every...
He got rejected by 60 VCs, burned all his savings—then grew to $100M …
Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks be...
Forget Founder Mode— MrBeast Mode is Where it's At. | The top 7 highl…
MrBeast's 36-page framework leaked this week. It's how he built a $1B+ company and became the #1 YouTuber in the world. His channel is worth over $1B. For the first time ever, we get to see how MrBeast operates. We go through the 7 most important things that startup founders can learn from MrBeast.…
He took on Uber & grew Rappi to $5B—here’s why the craziest founders …
Andres Bilboa is one of the co-founders of Rappi, the highest-valued app of LATAM ($5B valuation). Now he runs an incubator called Makers and has invested in dozens of startups. In this episode, he shares how Rappi started wi...
How to Get Free PR for Your Startup—Tips from the Editor-in-Chief of …
Douglas has been in media and PR for over two decades. He’s the founder of Betakit Inc and has been running Betakit, Canada’s TechCrunch, for nearly 10 years. He understands what startups need to do to leverage PR, and how PR...
He built Cohere into a $5.5B AI startup; How to Win in AI; & Why LLMs…
In this episode, I sit down with Nick Frosst, Co-Founder of Cohere, the $5.5B AI startup that’s targeting the enterprise landscape. We go through the origin story of Cohere, the challenges of building foundational models, and...
The ONLY guaranteed way to find Product Market Fit
Even if founders do everything right, they may still fail to find PMF. That's why even repeat founders have only 1.5% chance of building a unicorn. We talk about product-market fit constantly in this podcast. Hopefully, we learn from what others did and improve our chances of finding PMF. But there…