Uncapped #4 | Adam Guild from Owner

0:00All right, I'm super excited to be here with Adam the CEO of owner. Thanks for doing this. Adam, I'm really excited to have this conversation today. Thanks, Jack. I'm stoked. All right. So what I want to start with is you as a young founder. You dropped out of not college, but high school. When you were not even 18, you started owner. You're 25 now. And that's like still pretty young. All things can, you know, like I started. I was 26 and I felt like I was, I was like a pretty young founder. And you know, you're younger than I was when I started and you've already got. hundreds of employees and you know seven years of experience and tens of millions of revenue and all this other stuff.

0:35So that's like amazing. I also know you've like you know chewed a lot of glass and done a lot of hard stuff to get where you are and to make that happen and there's like a ton of backstory to what you've been through. So I guess I wanted to open with just you know Silicon Valley talks a ton about young founders and it's like this sort of both glamorized and sort of complicated topic but I'm sitting with one I'm sitting with a really good one and I just want to be inside your brain a little bit. Like, tell me about the experience of it. Initially, being a young founder is a huge disadvantage, particularly the type of young founder that I was, because I was a 10th grade high school dropout that had no credentials to my name, no professional network to draw on, no fancy college with a great computer science program to recruit classmates in order to build stuff.

1:21And the worst disadvantage of all was that I have a baby face. So when I was 17, starting owner, I looked like I was 12 and after grinding for weeks to get single demos appointments scheduled, I would walk into the restaurant to demo their software after emailing and texting and calling incessantly to try and initially grab their attention. And then they would look at me as I was telling them about SEO and I looked like I was 12 and they wouldn't take anything that I said seriously. They'd ask me things like, where'd you go to college and then I have to explain, didn't go to college. Why not? Because I dropped out of high school half way through 10th grade to build a Minecraft server.

2:03It led to all this friction where restaurant owners weren't willing to really even listen to what I had to say. Then this was like for context four years before I got any credentials to my name. Four years later, I ended up getting the T .O. fellowship. But for four years of building owner, young founder, no network, high school dropout, and just grinding to make things work. So what's interesting is that these disadvantages ended up flipping into being massive advantages, both in the way that they changed our strategy and the way that they pushed me as a founder and CEO to grow myself. I got sick and tired of having to grind so hard for trying to distribute our product outbound and sort of asking myself, how do I get them to come to me after having benefited from something that I've put out there in a way that actually makes them excited to chat with me.

2:55And this is what led to from the very earliest days focusing entirely on inbound. I realized that anybody could be an expert on the internet as long as they created content that was good enough. So one of the things that I did in that first year was I started writing a blog on restaurant marketing that had these very comprehensive articles because I had looked up to this marketer, Neil Patel, who I had learned a lot of marketing stuff from. And so I told myself I could be the Neopatel of the restaurant space, maybe people will benefit from the content and then want to use our product, which for the first few months didn't work because content takes a while, but eventually I ended up writing some of the most popular restaurant marketing articles of 2018 and 2019 at which point restaurant owners started reaching out and saying, I saw that article you posted.

3:39That was so helpful. I ended up doing the first strategy mentioned in my restaurant and in group I sell it. I'd love to chat with you about how your product might be able to help grow our sales even more. And then I would show up either for the Zoom call or for the in -person meeting and they would see that I was 18 years old at that point or 19 years old and you've blown away. And that's what ended up leading to us defying this trend in our space of selling via outbound because we had to build via inbound on that necessity alone. I was the first sales rep in the company and the person that needed to do all the demos and nobody was taking me seriously when I was going to them, but when they started coming to me, it flipped the dynamic entirely and that ended up being a superpower as a young founder, both in driving our strategy as a company, as well as in feeling extra energized by the fact that I had to work even harder.

4:29I mean, the beginning of most startups are very hard. I think it's actually, it's really uncommon that you just start and it goes really well. But so going back to those early years, you're 17, 18, 19, 20, you know, you're young. It took a while for you to find the right kind of product market fit. It's a hard market. You have these customers telling you you're a middle school intern, like fundraising's hard. Like, what was your mindset in those years? Like, what was keeping you holding through that early part of the curve that was, you know, so flat and so difficult? Like, how did you mentally hang through that when you were, you know, young?

5:05You didn't have a big network in Silicon Valley. you didn't have a bunch of money from investors, you didn't have customers, like what was going on for you? It was mostly desperation and some inspiration. The inspiration had come from the experience that I had in building the first version of what would become owner for my mom's dog ring business and seeing it completely transform her life as her business took off, seeing that this skill set that I'd learned in the gaming world to grow my Minecraft servers in mobile games had made her business take off and seeing not only the financial impact that had on her, but more importantly, personally seeing my mom go from constantly stressed out about money and terrified about potentially losing her business or losing our house, which she had taken out loans against to start the business to then reaching this place of such momentum in her life that she was feeling excited again about her future and proud of what she built.

5:58And that felt so much better to me than what I'd spent the past few years doing in the gaming world that I knew that that was the business that I needed to build a life around that I needed to figure out a way to scale this to help as many people like my mom as possible. I didn't get know how hard it would be, but in order to get in to scaling what would become owner, I basically sold my Minecraft servers and the mobile games that I'd built in order to focus there. And by the time I'd sold them, I needed to make this work as my way of supporting myself and making this massive bet that I'd taken on myself of dropping out of high school in 10th grade, having faith that I would figure it out worthwhile.

6:36I actually just remembered the fact that you were so connected to this idea of owners, and that was so deep for you. And I just remembered that you spent a crazy amount of money on that domain, and that that was like one of many non -avias calls you made. I mean, I can't remember exactly what the deal was, you know, and when it happened, but you spent a lot on owner .com if I remember. It's a pretty good domain name, but... Yes, a jaw -dropping amount that I'm not allowed to specify because there's a non -disclosure agreement in place with the seller, but an amount that was super controversial at the time to spend a huge amount of money.

7:07But you were pretty sure you were like, this is the North Star, this is a big deal. I was absolutely certain this focus on the small local business owner and in getting to know a lot of them realizing that the most important word in their vocabulary in a lot of cases is the word owner. Because 70 % of restaurant owners started off in entry -level positions as bussers or line cooks or servers, and then over the course of years or in some cases decades, they worked their way up into finally being this term that they're so proud to identify with, an owner. But they're increasingly feeling like they're losing control and ownership of their business as it's shifting online and so many companies are swooping in and separating them from their customers and then charging these massive fees, whether it's the delivery apps, but the reservations platforms.

7:59So this idea that we could have a name that was associated with the proudest word in our market, customers vocabulary and build a business around it felt like it would be worth any price. That was the calculus on that specific name, as well as knowing that there's a massive halo effect and perceived authority when a company has a sexy domain name and that in selling the small business owners, trust is scarce. Yeah. It is not products that are scarce. It is not new technologies that they could test out. Those things are very abundant. Overly so, but trust is scarce. And so if you are able to get that intuitive trust with a small business owner through showing them that you've got a really strong brand and a really strong domain name, what we found is that overnight the conversion and rate on our website increased by more than 50%, 50%, just with that change.

8:51I'll reply rate from candidates tripled. We saw all sorts of other massive benefits through having an ultra premium dividend. But, you know, and the confidence to make the type of bet that you did when you didn't have a lot of money in the bank that could have only come, those insights could have only come from you really spending a humongous amount of time with your customers. I mean, like, it's knowing their vocabulary inside and out. it's knowing that trust is what they operate based on and how that trust shows up. So you really could have only been that sure by being with your customers constantly, which you still do.

9:23Even when I walked in here today, a customer was walking out. Out of my apartment. Yes, it was a great apartment. But a customer was walking out as I walked in. And it's like, you're still doing that. And I'm sure you're always going to be doing that. On this topic of You know, you're a young founder and you were an even younger founder when you started. How did you think about getting yourself up to speed and learning the things that you need to learn? And on the other side, knowing when to trust your own gut and you've made that domain is when I just remembered, but you've made a lot of non -obvious calls on important topics and you've been right a lot about them.

10:00But you've chosen, I think what's most interesting to me is that you've chosen moments to say, you know, I trust a lot of the people around me. I'm gonna listen to what they say and I'm going against the grain in a big way here and I'm curious about how you've chosen. When are you in learn, listen and sort of follow advice mode and when are you in? I'm gonna make a call that is very controversial. I'm just gonna have my sort of faith to do that. The key here is that I'm always in the second mode of I will make whatever decision is in the long -term best interest in our business. But sometimes that decision is going to be one that a lot of people disagree with me on.

10:42Which in those cases, I've got to make sure that I'm operating with as much context and understanding of why people disagree. So that sharpens my thinking and can make me decide ultimately whether I have enough conviction to press on regardless of what really smart people are advising me against doing or whether they might have a point and I've got to adjust my perspective, but it comes from a place of not feeling personally attached to the stats that I might initially perceive as the right answer to a specific problem. and instead only starting to feel extreme attachment to a stance when I know that I've done the work and considered all of the different perspectives that one might take in solving this problem and that this is the best path even if people disagree with it.

11:33So how do you decide when to learn from others? Which I think is what I would characterize as your default is to sort of be learning from the world. And then when do you choose to go internal and pick your spots where you're gonna make and not obvious call and you're going to just hold your convictions. You know, this is hard to do in the face of an exact team that maybe doesn't see it the way you see it or investors or peer founders. But when do you decide this is my moment that I'm just going to do what feels right to me internally? I always do what feels right to me internally, but before deciding what feels right to me internally, it's really important that I carefully consider any perspectives on the topic before I arrive at my own conclusion, but I can.

12:19It's a good frame source from. So basically it's like even if what you concluded happens to agree with the people around you, which it often does, if it happened not to, you've gotten to a point where you don't care anymore, you would do it regardless. The thing that I look for before making big decisions is high internal conviction. And importantly, I don't have high internal conviction on the majority of big decisions, the moment that I consider them. I don't make snap judgments or intuition calls if it's the first time that I'm thinking about the problem. When I encounter a new problem that I haven't encountered before or haven't thought deeply about, my process is first very clearly defining what the problem is that I'm trying to solve.

13:06I write down pages and pages describing my various thoughts around the problem, the potential solutions, and don't judge or filter myself when I'm doing this journaling to get as much clarity as I can on what the simplest way to define the problem is. Then I start doing the same as I'm basically trying to get all of the potential solutions on paper, not evaluating them, not assigning them any value against one another, but just thinking about what are the conceivable ways to solve the problem, and then depending on the amount of conviction that I feel on those potential solutions, if it's not super high that I seek out other perspectives or seek out different books that I specifically approach with the goal of solving this problem to give me as much potential data as I possibly can have before making the decision, also acknowledging that there's so many decisions and startups that you will never have enough data to make a poor, unquote, perfect decision on where you have 100 % certainty that it's going to work, but that when you can get to that place of extremely high conviction, more often than not, it ends up being right.

14:12It's such a good instinct, I think, because it's so tempting for people, for all people, but it can be really tempting for people in leadership positions to feel the need to always have an opinion quickly and your face with a problem and you want to have all the answers and you want to turn that into, you know, a declaration fast. And I think like Most people shouldn't have an opinion about most things very quickly. You know, I think in a lot of cases it's actually okay for a CEO to just not even weigh in on a lot of stuff. Certainly not to have to do it quickly. And I think that you can run into traps when you decide, when you get into a headspace where you think you need to answer stuff fast and where you need to make decisions fast, I think that can be like a pitfall for people.

14:53I disagree with that framing actually. There are certain parts of that that I kind of agree with, but what I would nuance is that fast decisions are extremely important in startups. In decision as a CEO has cost a lot of momentum over the past six or seven years in any time that I've let it fester. So the interesting balance here is achieving both fast decision and having a considered rapid process. So what I do when I encounter one of these important new decisions that I don't have a lot of conviction on is I basically clear six to eight hours to go through as many resources as I can talk to people that I can Write out all of my thoughts and then try and clarify from those written thoughts Whether there is a direction that I have conviction and if not I continue searching in order to drive that decision.

15:45How do you decide which decisions are worthy of clearing your day? Is it like a one -way door or two -way door type thing or is it just you can tell an important decision when you can see it? How do you decide which are the ones where it's like, you know, I'm going to be quick and I'm going to be right 70 % of the time here and these are the ones that I'm going to give, you know, I'm going to give eight hours of real work to because I need to be like right when I say it. It's intuition based on identifying what the most important things for us to absolutely nail as a business are. There's things there on product, on go -to -market, on overall financing and structure of our company, management of leaders that are super high stakes, high leverage decisions that I need precision on in making those decisions, or at least as much conviction as I can quickly muster.

16:31But one of the things that I'm subconsciously considering there is whether it's a one -way door or two -way door in order to be able to assign the relative importance of that decision, relative to the other things in my calendar. The work ethic at owner has always been pretty outlier. It feels like to me yours too. I mean, I guess that's where it stems from, but feels to make the whole company has always had that pretty deep in the DNA. Like you seem to work pretty much all the time. Is that been something that's been hard to manage through or is how do you hold on to that? You know, even if the company's been growing, how have you evolved on that?

17:04Because obviously, you know, as the company grows, you're hiring people who, you know, have worked at bigger companies. Maybe people have kids, maybe people who are, it's just not realistic for them to work seven days a week. Like, what's the, what's the journey that owners currently on knowing that these routes were, you know, so all in to now your part way through the journey, your couple hundred employees. Like, what's that management been like? There's been two keys to keeping the intensity and work ethic even as we've scaled. The first piece is leading by example. So I'm very proud of the fact that I am working seven days a week, like often in 18 hour days like today, and that I'm not bragging about it openly to the team, but people noticed that when they send me a Slack at 10 p .m., I'm very quickly responsive just like I am at 5 a .m.

17:53Pacific time, or that I am able to get a lot done in every week that I have because I think ultimately it's got to start from the top. And if I'm not willing to show up with an extreme level of dedication, then I can't expect other people to, which I try to live by example, but I'm not calling out to our broader team constantly about it. The second piece is that an interesting byproduct of filtering for these traits in people, like being autodidactic in your learning, people that end up reading lots of books and listening to lots of podcasts, or people that take an extreme ownership mentality, which my favorite question for is if you were the CEO of your past company, what would you have done differently?

18:39If that's the first time that that question is even crossed their mind and they look like a deer in the headlights about like having no thoughts or just surface level thoughts, that to me is not an indicator that they were thinking as an owner in that role. That's such a good question because the quality of answer you could get there could be so high. Yes. Yes. And it is so high when people truly operate with that mentality. The best answer in my mind is a very clear assessment of here are the biggest problems to solve and here are solutions that were being overlooked, but that I have high conviction would have made a massive difference to our trajectory as a company, and we're our biggest opportunity for improvement.

19:12Okay, so that's like one great example. What are some other questions that you found have been like high impact for you? One of the interesting high -signal questions that I ask is what resources have been most formative to who you are as a person. But what I'm looking for there is not a specific resource for them to name, but the habit of going to external resources and learning from other people's experiences, having the curiosity to stand on the shoulders of giants and not approach every single problem that's something that we've got to learn from experience, but instead seeking out other perspectives, whether via books or podcasts or mentors that they recruit to show that they're going to scale well with the company through the effort that they put in to their continued learning and growth.

20:00So it's less about what the thing is, and it's more like how much have they thought about it, how deep have they gone with their own reflection, how it connects to themselves, it doesn't really matter what it is, it's about how they talk about it. My hot take here is that trying to go through life, purely learning from your own experience is hard mode. Of course, you've got to learn from your experience, but there's this great quote that summarizes my belief, which is that a wise person learns from their own mistakes, but a wiser person learns from the mistakes of others as well. That quote is so powerful to me because we've got two choices on how to learn about scaling in our role as a startup CEO or whatever role that I'm recruiting for.

20:46I can either make the choice to purely learn from trial and error in which case it's going to take me years or decades to get to certain conclusions because I won't have encountered them before or the right set of data to deepen my understanding or I can seek out people that have very successfully done similar things and try and distill their years or decades of learning into a few hours of studying how they made decisions how they operate in the early days how they think about that specific area of expertise. And the second route is so much more efficient. And to me has been personally transformative, so I look for other people that have activated that same superpower of their lives in learning voraciously from others.

21:29You also have talked about sticking with candidates to say no to you for months or quarters or even years in a couple of cases. Yeah, we just had an engineer that started two days ago that I recruited for four years. Crazy. Oscar. What happened? Like, how does the process go for four years? The way this all started was one of our first engineers who is amazing had previously worked with this candidate and described him to me when we first started working together as one of the very best engineers in tech, which from this engineer that tends to be very skeptical in nature particularly of others engineering abilities because he's very good.

22:08I didn't like mental. It was extremely high praise. This person doesn't think very highly of most other engineers. And the fact that they were describing this person with such high praise is what perked my ears up. The problem was this person had recently joined a very hot company that was getting a lot of financing from top firms and was being promoted constantly in this company to eventually lead a portion of the product as like a product leader engineer hybrid. And so there was a lot going against us over the past four years given that this was a larger company growing super fast great investors even though it was a clear no for three years and nine months at which point it turned into a maybe I knew how monumental getting an engineer like that on the team was and I also knew that it is not his responsibility to feel excitement for the opportunity of building at owner.

23:04It is my responsibility to convey all of the reasons to be excited and to persist knowing that long term. This would be in his best interest to join us and build together because he's so strong. And then basically being willing to shamelessly, even when I felt embarrassment of like the amount of times I'd texted and emailed and met with. I was just going to ask how many messages, how many unrequited messages were there? Over the past four years, I would say over 20. Wow. It wasn't like 20 back to back to back. Yeah, I'm sure you're replied. Yeah, yeah. We still hit it off on a friendly friendship level in initially connecting after this engineer spoke so highly.

23:42And immediately, we attempted to recruit him. It wasn't working because there were other forces at play, but it was basically not giving up. And interestingly, that is one of over 10 people in the company that are in extremely impactful roles now that I've persisted with for over a year before they joined us. Do you have other people that you're currently persisting with on a like a multi -year time frame like this that hopefully one day you'll get you know whether it's in six months or 20 months? Yes, even if it takes years. I keep this running list of people that I must work with throughout life where when I get an extremely strong impression of somebody as a individual that they're just a force of nature in their role.

24:27I add them to this list of those people and then I follow up with them every quarter to catch up to share the latest, to learn more about them, to develop the relationship so that when the stars do align, we are best positioned to work together because in startups, the team we build is the company we build. It is the single most important thing that I do as a CEO is building the team and obsessing over talent quality, but the only way to get the very best people who have literally dozens of offers competing for them is to continuously persist until the timing is right and the circumstances are right.

25:05What's the net of all of this in terms of hours per week, let's say, that you spend recruiting? I do time audits every week and 30 % of my time is spent in recruiting. That is the goal that I target against. Sometimes it's more, sometimes it's a bit less, but I really hold myself accountable to 30 % of my 10th Ann's researching references, interviews, all the rest of it. One of the really inspiring things that I heard on this front was I heard the node, Kostla, talking about how he views recruiting, even as the founder and managing partner of Kostla ventures in a multi -billionaire and how he still views it as so important that on weekend, and he'll spend time scouring LinkedIn and reaching out to candidates for his portfolio companies in order to help place them in those companies.

25:51And so I thought to myself, if Vinod is doing that at the scale that he's operating with billions of dollars in net worth to help portfolio companies, I better be doing that as well. So I don't feel above source in candidates. I don't feel above taking introductory or screening meetings even though we've got hundreds of headcount now, team is everything. And when I find really special people, or hear about really special people, I view it as my responsibility to figure out how we might be able to work together and persist if that's required. It's a small price to pay relative to the impact that they can have in the business.

26:21I've also heard you reference from the node, the like gene pool engineering of the team. Thank you. Share a little bit about that. Yeah. This was one of the game -changing moments as a founder when I started viewing recruiting through this lens early on. Gene pool engineering of a team is what the node calls, building your team around the biggest risks. in your business being able to reach multi -billion dollar scale and global impact. So here's the process. You start by identifying what those risks are. For example, one of our risks in serving small business restaurant owners is making the go -to -market motion extremely cost -effective and efficient.

27:00So then after identifying what the risk is of this type of business, you move on to what are the centers of excellence which he defined as companies that have successfully solved against that risk in the past and built best -in -class systems for solving that problem. In our case, it was Shopify and HubSpot because those companies have each very successfully and very efficiently distributed software to small business owners, defying the typical acquisition economics breakdown that happens when pursuing small business owners. Then, step three is going on LinkedIn Recruiter Search and figuring out who specifically was most responsible for the de -risking of those motions and who would know it inside and out.

27:47It's typically not whoever was the Chief Revenue Officer at that period, although they might have some insight. It's often a director of theirs or one of their specific team members that was able to solve the problem that is now ready for a VP or a C suite level role. At owner, an example of this would be Kyle, who initially was not looking for a new role. He was crushing it at Shopify. He was the revenue leader there that was scaling up their brand new POS line of business and After hearing amazing things about him from a bunch of his colleagues and various advisors of ours and initially connecting in an advisory capacity over the course of six months No became maybe and maybe became yes, which then was a massive unlock for our business as you know because he's been such an effective revenue leader and draws on years of experience and a super relevant network in de -risking, distributing effectively to small business owners.

28:41Kyle actually, that's another good topic. So, Kyle, the CEO, was, I think, at the time he joined. Some people would have said, he's more experienced, he's a stage ahead. And I think you've often done that, where you've hired what looks like a stage ahead on paper, of people who have, he's bigger experience as a bigger company, is leading bigger teams and you bring them into owner. And in your interview process, you're figuring out, can I make that person successful in my environment, but I want that person with that experience. Talk about the way you think about hiring ahead with your exact team.