The Product Market Fit Show

Last month, Ashby raised a $30M Series C. Ashby is used by customers like Notion, Ramp and Sequoia. Benjamin Encz built Ashby as an end-to-end Applicant Tracking System (ATS) that would replace several point solutions. In meant he had to build heads down for a while and couldn't launch a simple MVP. Surprisingly, even though he raised $3.5M at seed, he didn't grow his team. He built the product with just 3 people. "We could spend time recruiting or we could spend time building"-- he decided to build. When they launched, they grew to $200K in ARR within a year and then 10x'd a year after that. Here's the story of how they found product-market fit. Listen to the full episode here:

In 2014, Ian MacKinnon 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 small seed round. His main competitor, HootSuite, raised over $300M. In spite of that, he built a $40M ARR business that sold for well over $100M. Here's the story of how it all happened. And why there's an option besides bootstrapping and raising round after round: it's called the one & done. Listen to the full episode here:

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 the top 5%-- the ones where things went right and everything worked out. But you tend to learn more from failures than successes. On this episode, we go deep with David to see what building Tandym was like, why it ultimately didn't work, and what he would do differently the second time around. Listen to the full episode here:

Justin Adams 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, just a week before recording the episode, he shared a post on LinkedIn about a recent panic attack that left him frozen for 15 minutes. It turns out, the sheer pressure of running a startup gets to him-- like it does to most founders-- and shows up in the forms of panic attacks. Fortunately, he's getting better, but like all of us, mental health is something he has to grapple with, despite all the success he's had. We discuss mental health in startups, what it takes to be successful, the difference between bootstrapping and the VC-backed route, and how he grew his startup from nothing to 8 figures in just 4 years. Listen to the full episode here:

Rob Palumbo 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 ad spend dropped, growth ground to a halt. Nothing he did could revitalize growth. Ultimately, he decreased expenses and exited. He was able to return some cash to investors, find a home for his team and keep the product going. You tend to hear about what happens to the best 1% of startups. Here’s what tends to happen to the other 99%. Listen to the full episode here:

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, the VC who seeded Snapchat in 2012. Cameo became a unicorn in 2021. But as the markets turned, revenue decreased, investor interest waned, and their valuation dropped from $1B to $100M. After the restructuring and the layoffs, Steven Galanis found a way to turn things around. Now the company is profitable again. And growing. Here's how he did it.

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. We also talk about trends in founder vesting, and why some founders are choosing to vest for longer. Finally, we go through what to do if you’re stuck with some product-market fit but mediocre growth, and why more exits are happening now than anytime in the fast couple of years. Listen to the full episode here:

Lior Susan 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 and the Managing Director of Eclipse Ventures. And he's not building "easy" software startups either. Bright Machines is looking to automate the entire manufacturing process with robots. He launched it with a $179M round and a 100-person team.    Lior is not normal. His story isn't either. You won't want to miss this one. Listen to the full episode here:

Parker Gilbert 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 first year. He worked with a dozen design partners until the value prop was perfect. He even refused to let customers pay upfront in annual contracts. He wanted monthly payments to light a fire for him and his team. This month, just 3 years after quitting his job, he closed a $28M Series A. Here's exactly how he did it. Listen to the full episode here:

Mike Wessinger 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 that time, they went through the 2000 Dotcom crash and nearly went bankrupt in 2004 as they chased too many markets too soon. Since then, the company has continued to grow at over 20% compounded rate and hit $500M in ARR in 2024 and a $5B valuation. Mike shares how they started the company, the go-to-market strategy they used to go from 0 to $10M ARR and some of the most common mistakes he sees in the founders he works with today. Listen to the full episode here: