A Product Market Fit Show | Startup Podcast for Founders
00:00:00 · Dane Atkinson, Pablo Srugo
[00:00:00] S0: This is another thing that’s also really dangerous for founders, and it comes back to the VC cycle. You so desperately want this to work. It has to work. You’ve told everyone it’s going to work. You told your wife it’s going to work. Your kids know you’re carrying around coffee bags, like it’s got to work. That desperation off and turns into it not working, but you’re just making it work. [00:00:20] S1: Welcome to the Product Market Fit Show, brought to you by Mistral, a seed-stage firm based in Canada. I’m Pablo. I’m a founder turned VC. My goal is to help early stage founders like you find product market fit. Dane, welcome to the show. [00:00:38] S0: Hey, Pablo. Really happy to be here. [00:00:39] S1: Right now, you’re the CEO of Odeko Company that was started in 2019, and just last month, you raised a $50 million Series D. Before we get into that story, the Odeko story, I wanted to jump back, I guess at this point, nearly, what is that, 20 years or so when you were in 2007, you were the CEO of Squarespace, and Squarespace obviously a very well-known company. Today, it’s about a $6 billion business driving over $1 billion in top line sales. You joined a CEO in the really early days. The company was founded, if I’m not mistaken, in 2003. It was only a few years old doing about a few million revenue. Curious if you could go back to those days and just give us the inside story on how found out about Squarespace back then, and why you decided to join, just how that all played out.
00:00:39 · Pablo Srugo, Dane Atkinson
[00:00:39] S1: Right now, you’re the CEO of Odeko Company that was started in 2019, and just last month, you raised a $50 million Series D. Before we get into that story, the Odeko story, I wanted to jump back, I guess at this point, nearly, what is that, 20 years or so when you were in 2007, you were the CEO of Squarespace, and Squarespace obviously a very well-known company. Today, it’s about a $6 billion business driving over $1 billion in top line sales. You joined a CEO in the really early days. The company was founded, if I’m not mistaken, in 2003. It was only a few years old doing about a few million revenue. Curious if you could go back to those days and just give us the inside story on how found out about Squarespace back then, and why you decided to join, just how that all played out. [00:01:32] S0: Most of the things I’ve built, I’ve built as a founder. In this scenario, I was driving another company and stumbled into Squarespace through a friend and met the founder at the time and now CEO, Anthony Casalena, who had that brilliant gift of being both an engineer and a designer at the most extreme caliber in both, as well as solving the product market fit dilemma by just being the customer. He built the first version just to satisfy his need. [00:02:02] S1: Which was what, by the way? Today’s Squarespace used to make any type of website you want, but what was the key problem that he had that he was solving for?
00:02:02 · Pablo Srugo, Dane Atkinson
[00:02:02] S1: Which was what, by the way? Today’s Squarespace used to make any type of website you want, but what was the key problem that he had that he was solving for? [00:02:10] S0: The problem he had, and it was also similar when I joined up, was just blogging. Blogging at the time was incredibly hard thing to do. You had to stand up your own server. You had to do quite a bit of work, and that was only to share your ideas on things. He made it much easier system to get that done. You could already see the design of civic that’s lived on through the last decade in his tooling. I think the way he tells the story is he built this in his dorm room. Then one of his friends, who became a friend of both of us, Tristan, came in and was like, I’ll give you 20 bucks if I can build my own log on it. He was like, oh, all right, that sounds cool. I met him a number of years later. He had moved to New York in a dorm scenario with some friends and had a little office. I figured maybe we could pair up and try these be more meaningful. For a while, Sam and I sitting in a room trying to figure out how we could expand this to serve more people’s needs and navigate that journey, which <laugh> it’s fun as everybody out there knows.
00:02:10 · Dane Atkinson, Pablo Srugo
[00:02:10] S0: The problem he had, and it was also similar when I joined up, was just blogging. Blogging at the time was incredibly hard thing to do. You had to stand up your own server. You had to do quite a bit of work, and that was only to share your ideas on things. He made it much easier system to get that done. You could already see the design of civic that’s lived on through the last decade in his tooling. I think the way he tells the story is he built this in his dorm room. Then one of his friends, who became a friend of both of us, Tristan, came in and was like, I’ll give you 20 bucks if I can build my own log on it. He was like, oh, all right, that sounds cool. I met him a number of years later. He had moved to New York in a dorm scenario with some friends and had a little office. I figured maybe we could pair up and try these be more meaningful. For a while, Sam and I sitting in a room trying to figure out how we could expand this to serve more people’s needs and navigate that journey, which <laugh> it’s fun as everybody out there knows. [00:03:08] S1: First of all, it’s pretty crazy because it reminds me – this company started in 2003. Another company called Shopify started in 2004 under a very, very similar situation where Toby, the CEO, just wanted to sell snowboards online, so he creates this company to do so. People start knocking on his door like, hey, I also want to sell things online. That became $100 billion success there’s something there.
00:03:28 · Dane Atkinson, Pablo Srugo
[00:03:28] S0: There is, and there are many ways to go about finding your product guide. Being the customer yourself is one of the best, because especially if you can viscerally understand the desire and hold onto that as you grow, it’s fantastic. There are a couple of blind spots that get created. I remember sitting with Anthony, arguing over improving the core module versus adding a calendar, which would have taken hours versus days. I think you see one version of the world, but being truthful to that almost always leads to a good fit because you yourself are that fit. A lot of VCs, you not included a lot of investors are like, but the TAM is too small. You’re just focused on blogs, or you’re just focused on selling surfboards. That tends to not actually be an effective long-term strategy, because once you build something that works for a customer, as in with Squarespace, I think the big delta for us was we had these blogging components and we added a blank module, add a photo module, which allowed you to really expand the use case. Originally, it was like photo blocking. Before you knew it, people were building wedding sites, and their pet stores, and everything else on it because utility was so strong in the core that these extensions made a lot of sense for everybody. [00:04:45] S1: How do you become CEO? It’s not normal for somebody to just be like, hey, you come and join me as CEO. Did you try to invest or buy the company? Or did you tell him right off the bat, hey, I’d be better off leading this, you’ll make more money? How did happen?
00:04:45 · Pablo Srugo, Dane Atkinson
[00:04:45] S1: How do you become CEO? It’s not normal for somebody to just be like, hey, you come and join me as CEO. Did you try to invest or buy the company? Or did you tell him right off the bat, hey, I’d be better off leading this, you’ll make more money? How did happen? [00:04:59] S0: He’s wickedly smart, so there was no hope of buying the company, although that was definitely on my mind at the time. It was actually interesting journey. I love founders. I love startups. I’ve spent my life trying to build tools, Squarespace, and help Shopify, and all these. These have been a facilitator of that. He looked like, in a lot of ways, a younger version of me. I felt like if I can’t get a big hug of this, I could definitely help on the journey and share some of my scars. It was interesting because it was just really him at the point. The final interview I had to become his CEO was his dad. He had coffee somewhere in the ‘20s. I remember it was the last second [unclear]. He was like, yeah, my dad says you’re all right, so let’s go for it. All right, cool. [00:05:44] S1: That’s awesome. You ran that company, what was like, 2 to 10 million, 2 to 15 million? Is that more or less when you were there?