The Exchanges

Q So how did you go from this teenage Minecraft business to starting owner?

A When I started focusing full time on building games, which was what happened when I dropped out of high school halfway through 10th grade, it was first scaling the Minecraft servers up and then using that community of millions of players to Build my own mobile games. I started to feel very conflicted. There were certain things about that experience that I loved. It was so much fun day to day, and it was a great environment to learn software engineering and growth marketing in. But what I started to hate about it and hate about my life as I thought about my future was I felt when I looked forward three, five, 10 years of what my life would become focused in gaming, that it was basically scaling What I viewed as this negative impact because I was obsessed over how to get millions more players to ultimately waste time on my games so that I can make money. That's what you do as a gaming company. And that felt wrong to me. It, it didn't feel like something I wanted to spend my life doing, but I also felt kind of trapped because I didn't have a plan B. I was literally a 10th grade high school dropout. Didn't even finish 10th grade. And I knew there had to be some way to use that skill set that I built in Software engineering and growth marketing to actually help people, but I wouldn't know what that way would be until about a year later, I built the first version of Owner for my mom'…

AI assessment note: “I built the first version of Owner for my mom's dog grooming business”

Q So, as you sort of started to figure that out in month six and nine and 12, and this is all pre-pandemic, did it now start to feel like people were lining up at the door, or was it still a slow grind customer by customer?

A It felt a lot better than the cold outbound stuff. To me, it felt like people were lining up at the door, but I wouldn't truly know what that would feel like until a year and a half later, When we executed that post-pandemic pivot and added the online ordering module to our product. That's when things went hyperbolic. I thought it was great that we had a few dozen customers that had come to us from the inbound stuff, because somebody that had spent months grinding the outbound stuff, that was awesome. But what was really great was when we lost that online ordering product in May, we had hundreds of demo requests every week. We had so many demos that I had to create group demos to fit all the restaurant owners in that wanted to chat with me. Where I'd bring a group of three or four restaurant owners that had requested a demo, and I'd show them all the software together from, this was such a grindy period of the company, from like, seven a.m. Pacific, 10 eastern, to seven p.m. Pacific, I was in demos all fucking day that had booked inbound, and it was group demos, a lot of them. So three or four restaurant owners together would be seeing the software and then signing up. That was what real people lining up the door would feel like, and that's what real product market fit feels like. I had a very weak version of product market fit, if that. With the old dine-in focus website build…

AI assessment note: “To me, it felt like people were lining up at the door, but”

Q tried to sell to local restaurants and businesses that either got stuck and they themselves kind of got capped at X millions of revenue, or just the whole business was always upside down. What have you sort of figured out in maybe a more meta sense that might be useful to other people that are specifically thinking about other things that they want to do for this specific customer segment?

A To summarize my thinking on how to make the Very brutally difficult economics work of serving local business owners and restaurant owners. It comes down to making sure that the LTV to CAC ends up being very favorable, well over three. And the way you do that is both dropping CAC through finding resourceful, creative ways to distribute the product and maximizing LTV through delivering so much value in the product that you're able to charge a high price for it ultimately. We're doing both at Owner. On the dropping CAC, we've got not only this massive content marketing machine that is developing a large community of restaurant owners that trust us and are learning from all of the resources that we're putting out there for free, which then ends up making them want to become customers, but we've also got now our AI grader and AI website generator that makes it so that restaurant owners, in a matter of minutes and for free, Can start to experience the benefits of growing their sales through owner before they give us any money at all, which ends up giving us customer acquisition costs in the future that look more like Squarespace or Shopify with lifetime values that are even greater than toasts over time because the attach rate is so high once you earn the trust on free products. On the ensuring lifetime value is very high, that comes down to figuring out what the dollar ROI is on ado…

AI assessment note: “It comes down to making sure that the LTV to CAC ends up being very favorable”

Q Did you think about raising money before that point or just wasn't even really a consideration? It was like a non-decision.

A I had thought about it. I'd fantasized about it, really. It would be great to be able to do this, but for the longest time in starting off, I didn't know anybody in tech. I didn't know venture capital was a thing at first. And then when I realized it was a thing, I didn't think it was a thing that would be accessible to me. I didn't Nowhere to start and was in retrospect too focused on building the business the bootstrapped way, maybe at some level out of pride or imposter syndrome. And then when venture capital became an option, which came with all of these people that could really help develop my leadership and product abilities and advise in all these different ways, it felt like this huge blessing and superpower that I'm still Extremely grateful for it. The whole story of that, how that happened is bananas, if you're interested in hearing.

AI assessment note: “I had thought about it. I'd fantasized about it, really.”

Q Where did that come from, or what's the source of that?

A When I dropped out of high school, I had this fear that I was going to fall behind everybody that went to fancy colleges and was on that, that traditional track. So I promised myself that while my traditional education was ending, that my Self-guided education would ramp up. I started immediately from that point reading hundreds of books every year, listening to any business podcast that I could find. We're talking tens of thousands of hours over the past 10 years. The reason I've listened to a lot of these episodes is this is one of the resources that have been useful to me, and initially it came from that sense of fear that I would not be good enough to develop the life that I wanted or to get the things that I wanted, that I wasn't good enough ultimately, because I wasn't, and that I needed to become good enough Through having the humility of first of all, acknowledging that, and second of all, doing everything in my power every day to make myself the type of person that was capable of achieving what I wanted.

AI assessment note: “initially it came from that sense of fear that I would not be good enough”

Q And take a step back. When you spent this time doing what would be considered customer research, you reached out to thousands, talked to hundreds of different small business owners. What was the level of conviction you had before you built that first version of the Indyne booking product?

A I didn't interpret them not responding to my cold outreach as them not being interested in what I was doing. I interpreted it as them being extremely busy business owners that are constantly being bombarded by salespeople and just wanting to stay focused on growing their business, but I didn't take it personally and I didn't ascribe the meaning of, oh, they don't care about what I'm doing, which maybe was wishful thinking, but it was wishful thinking that served me because it ended up leading to them doing enough outreach where I'd have enough conversations And I was committed to making it work regardless of how many times I had to be rejected. So when I had those few conversations, I continued the wishful thinking and I'm like, Ooh, it sounds like if we can drive them more dine in reservations, they'd be interested in buying that and paying a lot of money for it. And one of the things that we did in the early days that was extremely important was we had a very high price for restaurant owners. We were charging 2000 dollars a month as a website builder around driving dine in and reservations. Which, to put that into perspective, typical website builders that restaurant owners use are Wix and Squarespace, and they're like, 49 a month products. So we were twenty-x the price, and in order to command that price, I thought to myself that we've got to deliver an ROI that is commensur…

AI assessment note: “committed to making it work regardless of how many times I had to be rejected.”