High School Dropout Turned Unicorn Founder | Adam Guild, CEO of Owner | Ep. 4

Jack Altman 0:00 [upbeat music] 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.

Adam Guild 0:06 Thanks, Jack. I'm

Adam Guild 0:07 stoked.

Jack Altman 0:07 All right, so what I wanna start with is you as a young founder. You dropped out of, not college, but high school when you were not even eighteen. You started at Owner. You're twenty-five now, and that's, like, still pretty young, all things consider-- You know, like, I started Lattice when I was twenty-six, 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 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 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 wanna be inside your brain a little bit. Like, tell me about the experience of it.

Adam Guild 1:02 Initially, being a young founder is a huge disadvantage, particularly the type of young founder that I was. Because I was a tenth 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 seventeen, starting Owner, I looked like I was twelve, 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 twelve, 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'd have to explain, "I didn't go to college." "Uh, why not?" "Uh, 'cause I dropped out of high school halfway through tenth 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 Thiel Fellowship, but for four years of building Owner, young founder, no network, high school dropout, and just grinding to, 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 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 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, 'cause content takes a while, but eventually, I ended up writing some of the most popular restaurant marketing articles of twenty eighteen and twenty nineteen, 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, 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, and they would see that I was eighteen years old at that point, or nineteen 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.

Jack Altman 4:29 I mean, the m- 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, tw- 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 customer-- Like, what was going on for you?

Adam Guild 5:10 It was mostly desperation and some inspiration.

Jack Altman 5:15 Mm.

Adam Guild 5:16 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 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 in to 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 tenth grade, having faith that I would figure it out, worthwhile.

Jack Altman 6:36 I 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-

Adam Guild 6:56 Yes, a jaw-dropping amount that I'm not allowed to specify because there's a non-disclosure agreement in place with the seller-

Jack Altman 7:02 But how you know it, yeah

Adam Guild 7:02 ... But an amount that was super controversial at the time to spend a, a huge amount of money.

Jack Altman 7:07 But you were pretty sure. You were like, "This is the North Star. This is a big deal."

Adam Guild 7:10 I was absolutely certain. This focus on the small local business owner and, and 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 seventy percent 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 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 customer's vocabulary-

Jack Altman 8:06 Mm-hmm

Adam Guild 8:07 ... 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.

Jack Altman 8:26 Yeah.

Adam Guild 8:27 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 fifty percent, five zero percent, just with that change. Our reply rate from candidates tripled. We saw all sorts of other massive benefits through having a ultra-premium domain name.

Jack Altman 8:57 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, 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, you know?

Adam Guild 9:27 Yes, out of my apartment.

Jack Altman 9:28 Yes, which is a great apartment.

Adam Guild 9:29 [chuckles]

Jack Altman 9:30 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

Jack Altman 9:34 you're always gonna 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 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, and I'm just gonna have my sort of faith to do that?"

Adam Guild 10:29 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 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.

Jack Altman 11:33 So how do you decide when to learn from others, which I think is what I would characterize as your default, um, is to sort of be learning from the world. And then, when do you choose to go internal and, you know, pick your spots where you're gonna make a not obvious call, and you're gonna just hold your convictions? You know, this, 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 gonna do what feels right to me internally?"

Adam Guild 12:03 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-

Jack Altman 12:19 Yeah. It's a good frame-

Adam Guild 12:20 -source from.

Jack Altman 12:21 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.

Adam Guild 12:32 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 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, 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 one hundred percent 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

Adam Guild 14:12 right.

Jack Altman 14:12 It's such a good instinct, I think, because it's so tempting for people, uh, 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 wanna have all the answers, and you wanna 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.

Adam Guild 14:53 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 in 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 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.

Jack Altman 15:46 How do you decide which decisions are worthy of clearing your day? Is it like a one-way door, a 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 what? I'm gonna be quick, and I'm gonna be right seventy percent of the time here, and these are the ones that I'm gonna give, you know, I'm gonna give eight hours of real work to because I need to be, like, right when I say it"?

Adam Guild 16:06 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 a-assign the relative importance of that decision relative to the other things in my

Adam Guild 16:43 calendar.

Jack Altman 16:43 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 it feels to me like the whole company has always had that pretty deep in the DNA. Like, you seem to work pretty much all the time. Has that been something that's been hard to manage through, or is... How, 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 routes 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?

Adam Guild 17:28 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 eighteen-hour days, like today, and that I'm not bragging about it openly to the team, but people notice that when they send me a Slack at ten pm, I'm very quickly responsive, just like I am at five 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 to lots of podcasts, or people that take an extreme ownership mentality, which my favorite question for

Adam Guild 18:34 is: if you were the CEO of your past company, what would you have done differently?

Jack Altman 18:38 Hmm.

Adam Guild 18:39 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 a indicator that they were thinking as an owner in that role.

Jack Altman 18:50 That's such a good question, 'cause the quality of answer you could get there could be so high.

Adam Guild 18:54 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 were the biggest problems to solve, and here were solutions that were being overlooked, but that I have high conviction would've made a massive difference to our trajectory as a company and were our biggest opportunity for improvement."

Jack Altman 19:12 Okay, so that's, like, one great example. Like, what, what are some other questions that you've found have been, like, high impact for you?

Adam Guild 19:18 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.

Jack Altman 20:00 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 themself? It doesn't really matter what it is. It's about, like, how they talk about it.

Adam Guild 20:10 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, 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 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

Adam Guild 21:29 from others.

Jack Altman 21:29 You also have talked about, like, sticking with, you know, candidates who say no to you for, like, months or quarters or, like, even years in a couple cases.

Adam Guild 21:37 Yeah. We just had an engineer that started two days ago that I recruited for four years.

Jack Altman 21:43 That's crazy.

Adam Guild 21:44 Oscar.

Jack Altman 21:45 What happened? Like, how does that- how does the process go for four years?

Adam Guild 21:48 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-

Jack Altman 22:08 Like, meant a lot

Adam Guild 22:09 ... 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.

Jack Altman 22:33 Hmm.

Adam Guild 22:33 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-

Jack Altman 22:52 Mm-hmm

Adam Guild 22:52 ... 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. 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, e- even when I felt embarrassment of, like, the amount of times I had texted and emailed and met with him-

Jack Altman 23:24 I was just gonna ask, how many mess- how many unrequited messages were there?

Adam Guild 23:27 Over the past four years, I would say over twenty.

Jack Altman 23:30 Wow!

Adam Guild 23:30 It wasn't, like, twenty back to back to back.

Jack Altman 23:32 Yeah, I'm sure he replied and-

Adam Guild 23:33 Yeah, yeah.

Jack Altman 23:33 Yeah.

Adam Guild 23:34 We, we-

Jack Altman 23:35 But still

Adam Guild 23:35 ... 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, 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 ten people in the company that are in extremely impactful roles now that I've persisted with for over a year before they joined us.

Jack Altman 24:02 Do you have other people that you're currently persisting with on a, like, a multi-year timeframe like this, that hopefully one day you'll get, you know, whether it's in six months or twenty months?

Adam Guild 24:11 Yes, even if it takes years.

Jack Altman 24:12 Mm.

Adam Guild 24:12 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, 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.

Jack Altman 25:05 What's the, like, net of all of this in terms of, like, hours per week, let's say, that you spend recruiting?

Adam Guild 25:10 I do time audits every week, and thirty percent 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 thirty percent of my time-

Jack Altman 25:24 And that's researching references, interviews, all the rest of it?

Adam Guild 25:27 Yeah. One of the really inspiring things that I heard at, 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 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 could have in the business.

Jack Altman 26:21 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?

Adam Guild 26:27 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 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 the centers of excellence, which he defines 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. 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. 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.

Jack Altman 28:41 Kyle, actually, um, that, that's another good topic. So Kyle, the, the C, 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, you know, 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, for, for Owner.

Adam Guild 29:21 Hiring big company executives that have only done big company work is always an unmitigated disaster.

Jack Altman 29:27 Disaster.

Adam Guild 29:28 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.

Jack Altman 29:50 Talk to me about the investor updates, because they are, like, works of art. Like, what's going on with those investor updates?

Adam Guild 29:55 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, I get, 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 and insight into how we're operating, not only to make sure that they feel continuously confident in and apprised of the decisions we're making, but also because ultimately, I want these relationships to last for life, for, for many decades. And I want to invest in them every single month in a way that I would feel confident that we'll still be friends in twenty or forty or fifty 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.

Jack Altman 31:39 It's a really nice way to live, and I actually think, um, one of the interesting things, you know, th- m- without sort of, you know, no judgment about it, but I think as Silicon Valley has gotten more, um, professionalized, let's say, and as it's become, you know, just much more, um, 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, and 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.

Adam Guild 32:21 One hundred percent 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 e- 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 of our investor relationships and making sure that I am doing everything in my power to give them as much information and clarity as possible on how the company's doing, on where they can help. And one of the magical things that happens when you do that-

Jack Altman 33:08 You get more help

Adam Guild 33:09 ... 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, and give you clarity on what we're doing, because you've done a ton for me.

Jack Altman 33:38 It's funny you say that, 'cause it was, uh, it was... I think mo- uh, all of your investors probably feel like we were the, 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. Um, but I do also think that one of the things that's happened because of the way you've 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 s- 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.

Adam Guild 34:14 I appreciate you saying that.

Jack Altman 34:15 One of the

Jack Altman 34:16 things that, uh, you mentioned is, uh, that you know quickly, you know about candidates, and so this is gonna be, like, a funny change in tone. There was a time that you, uh, interviewed a candidate, um, a few years ago, and you quickly realized that they weren't for you. And, uh, you shared about that story on Twitter. It's funny 'cause 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 have 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, I have a couple other questions about it?

Adam Guild 34:55 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 the 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?" 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 fifteen 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 gonna s- say very kindly, "I appreciate you finding the time this morning. Just to let you know, I don't think this is gonna be a perfect fit, 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, uh-... bringing in tons of great energy, so I, I really appreciate it. I've heard great things about you, and you're gonna be super successful in whatever you do, I'm sure, but it's just not gonna be the perfect fit at Owner.

Jack Altman 36:44 So it was a minute. It was a, like, one-minute conversation kind of thing?

Adam Guild 36:47 It was less than a minute, and he was very angry, and I was, I was very surprised by, by how angry he was. And so I, I called up my co-founder, Dean, and I'm like: "You would not believe the, the past two minutes o- of what just happened. I, 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 gonna be a great fit for Owner.

Jack Altman 37:09 Mm-hmm.

Adam Guild 37:09 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, if you know it's not gonna be a great fit. So then I went into our morning leadership meeting, 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, 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, and wasn't really paying attention. And then after I ended the leadership meeting, right before I hop into another meeting, I check my phone-

Jack Altman 38:02 And you were getting canceled.

Adam Guild 38:03 And I'm not exaggerating, the tweet had more than 100,000 organic impressions, and I had, 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?"

Jack Altman 38:23 And what year was this again? Remind me. 20-

Adam Guild 38:25 This was 2021.

Jack Altman 38:28 2020?

Adam Guild 38:29 2021 or 2022.

Jack Altman 38:30 Okay.

Adam Guild 38:31 And I was so taken aback to how angry people were by this. It, it really escalated when... Apparently, there's a community on Reddit called the Antiwork Community. I didn't know about them before this.

Jack Altman 38:42 Hmm.

Adam Guild 38:42 But we got posted to the Antiwork Community subreddit, which has a lot of active people, apparently, and they were just-

Jack Altman 38:50 Just riffing

Adam Guild 38:51 ... railing on me in this thread. All these crazy conspiracy theories about how, of course, Peter Thiel's 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, that it had evoked such an angry reaction. I, 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 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. [chuckles] And 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, have stuck to my intuition on whether somebody's a great fit, but the wrong decision to, to publicly share it.

Jack Altman 40:12 Yep. Yeah. So if you were facing that situation again today, you'd still end the interview, but you'd keep it to yourself?

Adam Guild 40:18 Definitely. I would end the interview, and I would share it with our team, transparently, and anybody that was curious.

Jack Altman 40:24 Yeah.

Adam Guild 40:24 It's not, like, a secret.

Jack Altman 40:25 Would you go out of your way to share it with your team just to, like, reinforce anything about the values or the hiring practices, or would that- that wouldn't be important?

Adam Guild 40:32 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.

Jack Altman 40:40 Like, we hire about... against them.

Adam Guild 40:42 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 wanna build-

Jack Altman 40:51 Yeah

Adam Guild 40:51 ... why would we spend 30 minutes of their time and 30 minutes of ours evaluating them in all these different dimensions if it's truly a non-negotiable?

Jack Altman 40:58 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 a- and it doesn't, it doesn't feel bad. It's what you wanna be doing.

Adam Guild 41:18 Yes, I agree with that to some degree, and I would delineate between different roles and the necessity of that.

Jack Altman 41:25 Yeah.

Adam Guild 41:25 Are we asking our customer support reps to work 100 hours a week? Absolutely not, nor is that an expectation or even a m- 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. 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-

Jack Altman 42:18 I love that

Adam Guild 42:18 ... 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

Adam Guild 42:41 of it themselves.

Jack Altman 42:41 One of the things I-... didn't appreciate the wisdom of until later is YC 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 YC and I, you know, you start, you know, work-- You start a comp-- 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. 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. Um, like, a couple examples are, like, I remember you once told me that you don't drink caffeine 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?

Adam Guild 44:03 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. 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.

Jack Altman 45:22 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, 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?

Adam Guild 46:00 It started from a place of insecurity, even before I'd met really special founders personally, and being really worried that all the people that told me that I was ruining my life, that I was making a very stupid decision, that I-

Jack Altman 46:21 Mm

Adam Guild 46:21 ... wasn't going to amount to anything when I dropped out of high school.

Jack Altman 46:24 Ah. It's almost like because you sac-- 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.

Adam Guild 46:33 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 passed 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. I promised myself that from that point forward, I would do everything in my power, [chuckles] everything in my power to scale as a person and as a leader. 'Cause 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 a hundred million dollars 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, which is just super inspiring to me and, 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.

Jack Altman 48:21 That was a powerful note to end on, Adam. This has been really fun to do this with you, and, uh, 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.

Adam Guild 48:30 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 shitshow in many ways, and the company was still a shitshow 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.

Jack Altman 49:06 Well, it's very nice of you to say. I, uh, I, I think I learned more from you than you do from me, and it was easiest bet of my life, but, but thank you, and thanks again. [upbeat music]