Uncapped #4 | Adam Guild from Owner

Adam Guild is the CEO of Owner, a business he started when he was only 17. It now has tens of millions of revenue, hundreds of employees, and thousands of customers. I’ve had the pleasure of working on his board for a few years now, and he is one of the most impressive people I’ve ever gotten to know. Working with him was a big part of what made me realize I want to do venture for the rest of my career. He tracks his nutrition, exercise, time, and sleep to an extreme degree so he can show up to work every day as strong as possible. He goes to extreme lengths to recruit the best talent. He is equal parts hungry to learn from everyone around him, but courageous in making his own unconventional decisions. I think he’s one of the most under-known founders right now, but I think that will soon change. Hope you enjoy watching this. --- Timestamps: (0:00) Intro (0:07) Inside the mind of a young founder (6:36) Boldly purchasing Owner’s domain (9:34) Listening to others vs being instinctual (14:12) Decision making as a CEO (16:43) Fostering a culture while scaling (18:34) High impact interview questions (21:29) Recruiting the best talent (29:50) Never missing an investor update (34:16) Getting canceled on Twitter (42:41) Startups are the Olympics of business --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: [email protected]

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Jack Altman?

  All 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.

• 0:06Speaker 01

  Thanks, Jack. I'm stoked.

• 0:07Jack Altman?

  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 considered, you know, like I started last when 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 have seven years of experience and tens of millions of revenue and all this other stuff. So 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

• 0:50Jack Altman?

  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.

• 1:01Speaker 01

  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. And 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.

• 1:45Speaker 01

  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 halfway through 10th grade to build a Minecraft server. It 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 TIO 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,

• 2:30Speaker 01

  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 started 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? And 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

• 3:12Speaker 01

  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, if I could be the Neil Patel 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. That was so helpful. I ended up doing the first strategy you mentioned in my restaurant and grew my sales. 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,

• 3:52Speaker 01

  and they would see that I was 18 years old at that point or 19 years old and be 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.

• 4:29Jack Altman?

  I 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 know, you're seventeen, eighteen, nineteen, twenty, 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? You 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?

• 5:10Speaker 01

  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 grooming 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 and mobile games had made her business take off and seeing not only the financial impact that 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

• 5:55Speaker 01

  excited again about her future and proud of what she'd built. And 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 yet know how hard it would be, but in order to get into scaling what would become owner, I basically sold my Minecraft servers and the mobile games that I had 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.

• 6:36Jack Altman?

  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-obvious 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.

• 6:56Speaker 01

  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.

• 7:06Jack Altman?

  But you were pretty sure. You were like, this is the North Star. This is a big deal.

• 7:10Speaker 01

  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 them these

• 7:55Speaker 01

  massive fees, whether it's the delivery apps or the reservations platforms. So 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 to small business owners, trust is scarce.

• 8:26Jack Altman?

  Yeah.

• 8:26Speaker 01

  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 rate on our website increased by more than 50%, 5-0%, just with that change. Our reply rate from candidates tripled. We saw all sorts of other massive benefits through having a ultra-premium domain.

• 8:57Jack Altman?

  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 like, you know, trust is what they operate based on and like how that trust shows up. So you really could have only been that sure by being with your customers constantly, which, you know, you still do. I mean, like, even when I walked in here today, a customer was walking out.

• 9:26Speaker 01

  Yes, out of my apartment.

• 9:27Jack Altman?

  Yes, which is a great apartment. But a customer was walking out as I walked in. And it's like, you know, 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 one 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. But 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 going to listen

• 10:10Jack Altman?

  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, and I'm just gonna have my sort of faith to do that?

• 10:29Speaker 01

  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 of our business. But sometimes that decision is going to be one that a lot of people disagree with me on, which 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 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 stance that I

• 11:12Speaker 01

  might initially perceive as the right answer to a specific problem, and instead only

• 11:20Speaker 01

  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.

• 11:33Jack Altman?

  So 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 going to make a not obvious call and you're going to just hold your convictions? This is hard to do in the face of an exec 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?

• 12:03Speaker 01

  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 that I can.

• 12:19Jack Altman?

  Yeah, that's a good frame.

• 12:20Speaker 01

  Source from.

• 12:21Jack Altman?

  So basically, it's like, even if what you concluded happens to agree with the people around you, which it often does, if it happens not to, you've gotten to a point where you don't care anymore, you would do it regardless.

• 12:32Speaker 01

  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. I 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

• 13:17Speaker 01

  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.

• 13:27Speaker 01

  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, then 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 in startups that you will never have enough data to make a quote 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.

• 14:12Jack Altman?

  It'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 you're faced 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.

• 14:53Speaker 01

  I 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. Indecision as a CEO has cost a lot of momentum over the past six or seven years and any time that I've let it fester. So the interesting balance here is achieving both, a 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

• 15:36Speaker 01

  try and clarify from those written thoughts, whether there is a direction that I have conviction in, and if not, I continue searching. In order to drive that decision.

• 15:46Jack Altman?

  How do you decide which decisions are worthy of clearing your day? Is it like a one-way door, 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.

• 16:06Speaker 01

  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. But 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.

• 16:43Jack Altman?

  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 me that 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 as the company's been growing? How have you evolved on that? Because 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 Owner's currently on, knowing that these roots were, you know, so all in? To now you're partway through the journey, you're a couple hundred employees. Like what's that management been like?

• 17:28Speaker 01

  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, often in 18-hour days like today.

• 17:44Speaker 01

  And that I'm not bragging about it openly to the team, but people notice that when they send me a Slack at 10:00 PM, I'm very quickly responsive, just like I am at 5:00 AM Pacific 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

• 18:25Speaker 01

  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? If that's the first time that that question has 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.

• 18:50Jack Altman?

  Such a good question, because the quality of answer you could get there could be so high.

• 18:54Speaker 01

  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 where our biggest opportunity for improvement.

• 19:12Jack Altman?

  Okay, so that's like one great example. Like, what are some other questions that you found have been like high impact for you?

• 19:18Speaker 01

  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 as something they'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.

• 20:00Jack Altman?

  So it's less about like what the thing is and it's more like how much have they thought about it? How deep have they gone with sort of their own reflection, how it connects to themselves? It doesn't really matter what it is. It's about like how they talk about it.

• 20:10Speaker 01

  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. I 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

• 20:54Speaker 01

  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 operated 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.

• 21:29Jack Altman?

  You also have talked about like sticking with, you know, candidates who'd say no to you for like months or quarters or like even years in a couple of cases.

• 21:37Speaker 01

  Yeah, we just had an engineer that started two days ago that I recruited for four years.

• 21:43Jack Altman?

  Crazy.

• 21:44Speaker 01

  Oscar.

• 21:44Jack Altman?

  What happens? Like, how does that, how does the process go for four years?

• 21:47Speaker 01

  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,

• 22:08Jack Altman?

  like mental.

• 22:09Speaker 01

  Extremely high praise. This person doesn't think very highly of most other engineers.

• 22:15Speaker 01

  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.

• 22:58Speaker 01

  And I also knew that it is not his responsibility to feel excitement for the opportunity of building at Owner. It 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 had texted and emailed and met with him.

• 23:24Jack Altman?

  I was just gonna ask, how many unrequited messages were there?

• 23:27Speaker 01

  Over the past four years, I would say over 20.

• 23:30Jack Altman?

  Wow.

• 23:30Speaker 01

  It wasn't like 20 back to back to back.

• 23:32Jack Altman?

  Yeah, I'm sure you replied.

• 23:33Speaker 01

  Yeah, yeah. We hit it off like on a friendly friendship level in initially connecting after this engineer spoke so highly. And 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.

• 24:02Jack Altman?

  Do you have other people that you're currently persisting with on like a multi-year timeframe like this that hopefully one day you'll get, you know, whether it's in six months or 20 months?

• 24:10Speaker 01

  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

• 24:22Speaker 01

  A individual that they're just a force of nature in their role. I 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.

• 25:05Jack Altman?

  What's the like net of all of this in terms of like hours per week? Let's say that you spend recruiting.

• 25:10Speaker 01

  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 time.

• 25:24Jack Altman?

  And that's researching, references, interviews, all the rest of it?

• 25:27Speaker 01

  Yeah, one of the really inspiring things that I heard on this front was I heard Vinod Khosla talking about how he views recruiting, even as the founder and managing partner of Khosla Ventures and a multi billionaire, and how he still views it as so important that on weekends, he'll spend time scouring LinkedIn and reaching out to candidates for his portfolio companies in order to help place them in those companies. And so I thought to myself, if Vinod is doing that at the scale that he's operating with, with billions of dollars in net worth to help portfolio companies, I better be doing that as well. So I don't feel above sourcing candidates. I don't feel above taking introductory or screening meetings, even though we've got hundreds at Hemcat now. Team is everything. And when I find really special people or hear about really special people,

• 26:12Speaker 01

  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.

• 26:21Jack Altman?

  I've also heard you reference from Vinod, the like gene pool engineering of the team thing. Can you share a little bit about that?

• 26:27Speaker 01

  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 Vinod calls building your team around the biggest risks.

• 26:42Speaker 01

  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. So then after identifying what the risk is of this type of business, you move on to what are these 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

• 27:24Speaker 01

  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. It's typically not whoever was the chief revenue officer at that period, although they might have some insights. 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.

• 28:08Speaker 01

  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 in a super relevant network in de-risking, distributing effectively to small business owners.

• 28:41Jack Altman?

  Kyle, actually, that's another good topic. So Kyle, the CRO, 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 these bigger experiences at bigger companies, 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 like, you know, the way you think about hiring ahead, you know, with your exec team. I think that's like, you know, something that is noteworthy to me for Owner.

• 29:20Speaker 01

  Hiring big company executives that have only done big company work is always an unmitigated disaster.

• 29:27Jack Altman?

  Disaster.

• 29:27Speaker 01

  But hiring people that are big company executives that have previously had experience doing stuff at this stage can be a superpower because they've seen both sides. They've seen what best in class looks like at scale eventually, and they've seen what specific actions, systems, strategies were really successful at this stage to create those success stories.

• 29:50Jack Altman?

  Talking about the investor updates, because they are like works of art. Like, what's going on with those investor updates?

• 29:55Speaker 01

  I'm very proud that we've never missed an investor update since the first dollar we raised, and it's been more than five years of not only never missing, but always being exactly on time. Where that comes from is feeling extremely grateful to our investors, because for the first two and a half years of building Owner, I didn't think I'd be able to raise venture capital. I didn't think I'd be good enough to raise money, and I didn't know anybody that had. The fact that people have bet millions of dollars that they're responsible for on our success is touching to me. Even still, like, I can almost feel emotional thinking about it, because at some level, they're staking some part of their career and their success on believing in me and believing in the company, and I feel that I owe it to them to give them as much transparency

• 30:40Speaker 01

  and insight into how we're operating, not only to make sure that they feel continuously confident and apprised of the decisions we're making, but also because ultimately, I want these relationships to last for life, for many decades, and

• 30:58Speaker 01

  I want to invest in them every single month in a way that I would feel confident that we'll still be friends in 20 or 40 or 50 years' time because of how much effort and value I put into the relationship. It comes mostly from a place of gratitude and also knowing that the tech world is small and that reputation in the tech world is everything. So my belief from the beginning is that I've got to treat the people that bet on me like gold because in the case that I was never able to raise another outside dollar again, I would want to treat them so well that they would feel really excited and confident about continuing to bet on me because of the way that I lead.

• 31:39Jack Altman?

  It's a really nice way to live and I actually think one of the interesting things, you know, without sort of, you know, no judgment about it, but I think as Silicon Valley has gotten more professionalized, let's say, and as it's become, you know, just much more understood how startups are built and there's tons of venture capital, there's tons of startups. I think, not that the, you know, VC founder relationships are negative, but I think in they are often transactional and I don't think they have to be. And so it's a, it's a nice perspective to treat those relationship, treat the, the money that gets exchanged as part of a much broader relationship, not just like a, a deal that happened.

• 32:21Speaker 01

  100% agree with you and think that it is really important in long-term optimizing for the company's success to never treat relationships as transactional, to, to be extremely proactive in nurturing and treating the relationship like gold because ultimately reputation is everything, not just in fundraising, but recruiting, in customer acquisition. We think that that is always the most important long-term thing to optimize for, which sounds generic in theory to say, but the way we. Action, that concept is with all our investor relationships, making sure that I am doing everything in my power to give them as much information and clarity as possible

• 33:03Speaker 01

  on how the company is doing, on where they can help. And one of the magical things that happens when you do that is you get more help. And we've been so blessed from our very first seed round, where it's been the same group of investors that then doubled down and tripled down and quadrupled down in our company. And I'm so, so grateful to them and to you for, for believing in me. It feels like the least I can do to make sure that those updates are great and on time for you and give you clarity on what we're doing because you've done a ton for me.

• 33:38Jack Altman?

  It's funny you say that because it was, it was, I think all of your investors probably feel like we were the lucky ones and you were an easy person to bet on the whole way through. But it's still very nice of you to say. But I do also think that one of the things that's happened because of the way you treated investors is I've observed you getting a lot more help from your investors than a lot of people do because that relationship is so not transactional. And so I, you have a lot of, you know, besides the institutions, you also have a lot of great angels and I see a lot of people who really want you to win. And I think a lot of that has to do with the way you've treated people the whole time.

• 34:14Speaker 01

  I appreciate you saying that.

• 34:15Jack Altman?

  One of the things that you mentioned is that you know quickly, you know, about candidates. And so this is going to be like a funny change in tone. There was a time that you interviewed a candidate a few years ago and you quickly realized that they weren't for you. And you shared about that story on Twitter. It's funny because for me now, looking back on it, I'm like, that should have been one of the first moments that I saw like real greatness in you as a CEO. It might've been, I don't even remember if that was one of the moments. But thinking back on that, I'm like, what an obviously good CEO that is. So can you share what happened there, what you did? And then I'll have a couple of other questions about it.

• 34:54Speaker 01

  Yeah. This was an interview that I was really excited for. One of the marketing leaders at Shopify that had done a lot of relevant stuff, agreed to meet when I reached out on email and LinkedIn. And so I'd done a ton of prep work, learning about this person's background and relevant things that they'd done. Then we head into the meeting and the question that I opened with to get the conversation flowing was, hey, How's it going? And they, in the most drained and jaded possible way, looked into my eyes and said, I'm counting down the hours till the weekend. How about you?

• 35:37Speaker 01

  Just like that, just like almost deadpan monotone. And one of the more controversial things that I look for in people for our team is bringing great energy, we call it, people that are super energized and optimistic by default. So when he said, counting down the hours till the weekend, how about you? I knew within 15 seconds that while he might be an extremely skilled and experienced marketer, that we weren't going to work well together. And so I thought out of respect for his time and my time, I'm just going to say very kindly, I appreciate you finding the time this morning. Just to let you know, I don't think this is going to be a perfect fit.

• 36:22Speaker 01

  And I don't want to take up any of your time in this conversation because my belief is that startups are too hard to be counting down the hours till the weekend. Like I believe in working weekends at this stage and bringing in tons of great energy. So I really appreciate it for great things about you. And you're going to be super successful in whatever you do, I'm sure. But it's just not going to be the perfect fit at Owner.

• 36:44Jack Altman?

  So it was a minute? It was all like a one minute conversation?

• 36:47Speaker 01

  It was less than a minute. And he was very angry and I was, I was very surprised by how angry he was. And so I called up my co-founder Dean and I'm like, you would not believe the, the past two minutes of what just happened. I got on with this candidate, I was very excited. And he said that at the beginning of the conversation, I just knew that it wasn't going to be a great fit for Owner. And Dean found it really funny that like, good for you. You know what we, we want and need in people. And I think it's actually kind long-term to not waste 30 minutes or an hour of this person's time. If you know it's not going to be a great fit. So then I went into our morning leadership meeting.

• 37:27Speaker 01

  But right before I did, I thought this is a potentially good thing to share about our culture that like, We're looking for people that are really energized and excited about their work and excited to potentially work weekends. I thought that that was like an important thing to be transparent about. So I tweeted out exactly what happened, those exact words, and went into this leadership meeting, turned my phone off. And for 90 minutes, we went through every part of the business, our metrics, how things were progressing, and wasn't really paying attention. And then, after I ended the leadership meeting, right before I hop into another meeting, I checked my phone. And you were getting canceled. And I'm not exaggerating, the tweet had more than 100,000 organic impressions,

• 38:08Speaker 01

  and I have like 1,000 followers in an hour. It had gone so hyperbolically viral of people getting really offended and angry with me, saying, this is disgusting, are you running a sweatshop? Are people not allowed to count down the hours till the weekend? What year was this again? Remind me? This is 2021? 2020? 2021 or 2022. Okay. And I was so taken aback to how angry people were by this. It really escalated when apparently there's a community on Reddit called the Anti-Work Community. I didn't know about them before this, but we got posted to the Anti-Work Community subreddit, which has a lot of active people, apparently. And they were just railing on me in this thread,

• 38:52Speaker 01

  all these crazy conspiracy theories about how, of course, Peter Thiel is associated with this person because I got a Thiel Fellowship, and this is disgusting, this is everything that's wrong with Silicon Valley in one tweet. And not only were they like angry on Reddit, but they were writing all of these crazy nasty messages to the initial message and then tweeting my investors. One of them wrote Jason Lemkin this very long email about, how dare you back this founder? This is the most disgusting behavior. How could he treat people this way? And it was interesting to me that it had evoked such an angry reaction. I meant it as a very light tweet. And then I actually ended the tweet with thoughts, because I was curious to get other perspectives. This is one of the reasons why I don't really post

• 39:35Speaker 01

  that much on X anymore. I'm not curious in hearing like the broader internet's thoughts, because I think there's a lot of really toxic mindsets that are brought in, at least from my perspective, although from their perspective, apparently I'm toxic.

• 39:47Speaker 01

  It it both led to the importance of like, in my mind, not outsourcing any thinking or opinions from like, the broader internet community and the clarity that it was actually the right decision to respectfully end the interview in that way and have stucked to my intuition on whether somebody's a great fit, but the wrong decision to publicly share it.

• 40:12Jack Altman?

  Yep. Yeah. So if you were facing that situation again today, you'd still end the interview, but you'd keep it to yourself?

• 40:18Speaker 01

  Definitely. I would end the interview and I would share it with our team transparently and anybody that was curious. It's not like a secret.

• 40:24Jack Altman?

  Would you go out of your way to share with your team just to like reinforce anything about the values or the hiring practices or that wouldn't be important?

• 40:31Speaker 01

  I would go out of my way to share it with the team for exactly that reason, reinforcing this idea that our values aren't just corporate BS.

• 40:40Jack Altman?

  Like we hire about against them?

• 40:42Speaker 01

  Yes, they are non-negotiables in the people that we bring on. And so if somebody very early on is showing us that they are not going to be aligned with the type of company that we want to build, why would we spend 30 minutes of their time and 30 minutes of hours evaluating them all these different dimensions if it's truly a non-negotiable?

• 40:57Jack Altman?

  One of the things I always tried to think about with like, that made it easier was just people who loved their work, who you don't, who then are just driven on their own to want to work because they love it. Like if you don't experience your work as work, which I think a lot of people don't, I think that, you know, that puts you in a position where you can work all the time and it doesn't, it doesn't feel bad. It's what you want to be doing.

• 41:17Speaker 01

  Yes, I agree with that to some degree. And I would delineate between different roles and the necessity of that.

• 41:25Jack Altman?

  Yeah.

• 41:25Speaker 01

  Are we asking our customer support reps to work 100 hours a week? Absolutely not, nor is that an expectation or even a major positive. Because there are certain roles that lend themselves to having other priorities in life and are able to have much more of a balance, which we are encouraging of. We expect excellence of those people in different ways, but we're not expecting them to dedicate their entire existence to the company. In certain other roles, like really key leadership roles, it's important to me that our leaders operate with. A huge amount of intensity and lead by example in the way that I do because I view them not as my employees, but as my partners in developing the business. That's how I treat them. That's how we talk about the business together.

• 42:07Speaker 01

  I'm not treating them as employees and I expect them to show up in a way that indicates to me their level of commitment and intensity and focus on our business. It really varies.

• 42:17Jack Altman?

  I love that.

• 42:18Speaker 01

  At this stage, but at the seed stage, when every single hire was life or death critical, which is how we viewed it, we were more intense about enforcing extreme work ethic on those roles because ultimately the first customer support rep is kind of like your head of customer support that's developing all of the systems and they're almost like an executive in and of it themselves.

• 42:41Jack Altman?

  One of the things I didn't appreciate the wisdom of until later is Y C and Paul Graham talked a lot about how important it was to exercise, actually. And I was just like, oh, that's kind of like a funny thing. And then, but then when I was in Y C and I, you know, you start, you know, work, you start a company, you just start working constantly. And I quickly realized how important your own physical health, mental health are to being able to do the work. But I actually think it's like deep wisdom that like, you know, we're, we're working in our bodies, keeping your body strong and healthy is, is a big deal. You have what I would describe as like outrageously outlier personal discipline on a bunch of fronts. Like a couple of examples are like, I remember you once told me that you don't drink caffeine

• 43:25Jack Altman?

  specifically because you didn't want to have like the crashes, which you thought would make you like net less productive. And then at some point you changed that and you started using caffeine, but you cycled it and it was like using caffeine, not like drinking coffee because you feel like it. You know, you've also, you know, the way that you think about your sleep, your calendar audits, the food you eat, the exercise you do, you like, I don't know if you're still meditating twice a day, but you were at one point, but it's pretty like, it's pretty dialed. So like, have you always been that way? Is this all for the purpose of owner? If you weren't building owner, would you be super disciplined, even if you were hanging out on the beach, which is hard to imagine you doing, but like what's, what's the story with all this discipline?

• 44:03Speaker 01

  There's a few different parts to this that have actually evolved over time. It started from a place of insecurity and acceptance, realizing early on in getting to know some really intimidatingly great founders that I was not going to be able to win on intelligence. There are some founders that are extremely brilliant, one in a million level brilliant, like Alex Wang from Scale, I'd put in this category, breathtakingly smart. And that is not me. I am smart enough to be effective, but I've got to work that much harder versus those founders that are extremely smart. I will not be outworked.

• 44:47Speaker 01

  Startups are the Olympics of business. And as the founder and CEO of a startup, I've accepted the responsibility that I've got to compete like an Olympian, taking every input into my life seriously, not just hoping to show up with the right level of energy or the right level of clarity of mind, but also controlling all of the parts of my life like Michael Phelps does when he's going for a gold medal with his exercise routine and his diet and the various other contributing factors that are going to affect the way that I am able to show up in work.

• 45:22Jack Altman?

  I've never heard somebody describe it that way of like treating it, you know, like, you know, the Olympics of business or whatever, but like, that's actually a very inspiring way to put it. Did you develop this mindset over some period of time or were you wired this way before, owner? Or like, how did you come to that? Cause you're not just, I know you well enough to know you're not just saying that, like you live this like kind of every minute to like an extreme degree, like, how did you get, I mean, you know, you shared this realization or this sort of opinion that you're like, you know, and you're being a little humble, you're a very smart guy, but you know, obviously, you know, there's bell curves on things and Alex Wang's really smart and whatever. But how did you come to this?

• 46:00Speaker 01

  It started from a place of

• 46:04Speaker 01

  Insecurity, even before I had met really special founders personally, and being really worried that all of the people that told me that I was ruining my life, that I was making a very stupid decision, that I wasn't going to amount to anything when I dropped out of high school.

• 46:25Jack Altman?

  It's almost like because you sat, you put so much on the line by dropping out of high school, that it adds even extra pressure to not leave anything up to chance.

• 46:33Speaker 01

  Yeah, I was worried they'd be right if I didn't do everything in my power from that point forward to give myself the best possible opportunity to succeed. That's also when I started reading super voraciously. I actually didn't read in school. I was conditioned to view reading the way school teaches us to, which is trying to memorize all these random rote facts from the outsiders that we pass the English test, and reading being just a means to an end of proving that you're compliant with the teacher. But when I dropped out of high school, I was so worried that I was going to fall behind everybody in my peer group, that the people that went to fancy colleges would learn all of these amazing things about business and then crush me.

• 47:20Speaker 01

  I promised myself that from that point forward, I would do everything in my power, everything in my power to scale as a person and as a leader. Because another belief that powers this is accepting that I am not the CEO yet that I need to be for the next stage of scale. That there's a ton of work that I've got to do to figure out how to operate this business when it's got $100 million in annual revenue, or a billion dollars in annual revenue. And I don't have all the answers now, nor am I the most brilliant founder that can just coast on intelligence alone, which I'm not saying that that is the case with Alex or anybody else. They also work super hard,

• 48:02Speaker 01

  which is just super inspiring to me and pushes me to work that much harder. But I will not be outworked and I will not let myself down or any of the people that bet on me down in. The way that I execute against all the factors that are in my control.

• 48:21Jack Altman?

  That was a powerful note to end on. Adam, this has been really fun to do this with you. And more importantly, it's just a, it is a real pleasure to get to work with you every day. So thank you for, for everything.

• 48:30Speaker 01

  I just wanted to say that I feel extremely grateful that you bet on me when you did. You believed in me when I was still a shit show in many ways. And the company was still a shit show in many ways back when we were a seed stage company. And believed in me before I fully believed in myself. And that was life changing because it gave me a ton of courage and encouragement to continue executing to the best of my ability and changed my life to be able to learn from you and have the confidence that somebody as impressive and awesome as you believed in me too.

• 49:06Jack Altman?

  Well, it's very nice of you to say, I, I, I think I learned more from you than you do from me. And it was easiest day of my life, but, but thank you and thanks again.