Zero to $80M in 4 years with John Andrew Entwistle of Wander

When you start a company, you're effectively signing up for a pretty meaningful life chapter. Think, when are we going to get to the point where it's like easy for me? And he said, John Andrew, it will never be easy for you. You are always going to have to try. And so when it comes to building startups and companies, your odds of success are exceptionally low. And so you have two choices. You can either be very, very thoughtful and strategic about what am I going to do, how am I going to do it, or you can just like be like, I'm going to wing it. Things were a mess. There was a ton of work to do. And I remember being there with the team and saying, no one is coming to save us. And so when you pair those two ideas together, that everything matters and that no one is coming to save you, then you feel this sense of agency and responsibility that hopefully can build a beautiful company.

Welcome to Just Go Grind. I'm your host, Justin Gordon. On today's episode, we have John Andrew Entwistle, the founder and CEO of Wander, previously the CEO of Coder.com, as as well. He's been a Thiel Fellow, a Forbes 30 Under 30, and he's only 27 years old. His latest company, Wander, is essentially a luxury home rental company. It's like an Airbnb competitor. It is incredible. You can book a Wander with inspiring views, hotel-grade amenities, dreamy beds, top-tier cleaning, and 24/7 concierge service. It's a vacation home but better, and their slogan is "Find your happy place." Wander has grown like crazy over the last few years. They're only a few years old and they've grown absolutely insane, which is why the perfect sponsor for today's episode is Ro. Every founder knows how painful of an experience it can be to work with a bank, but Ro makes it easy. Just like how Wander makes it incredibly easy to book a home, get an amazing luxury vacation rental, Ro makes it easy to have a business bank. They have a single pane of glass you can use to run and scale your business from day one. That's bank account, corporate cards, expense management, bill pay automation, and accounting to help you move fast as you scale, just like a company like Wander has. Row is trusted by thousands of companies ranging from 2-person YC startups to brands like Perplexity, Cal.com, Splitwise, and more. And the big thing with Row, every customer has a person at Row that's 24/7 customer support, phone, text, email. They will be with you every step of the way at every critical milestone in your startup's journey, just like how Wander is with you every step of the way in your vacation rental. To learn more about why startups choose Ro, visit ro.co today. That's R-H-O.co today to get started. Let's get to the episode with John Andrew Entwistle, the founder and CEO of Wander. John Andrew, welcome to the show.

Thank you so much for having me. I'm super stoked to be here.

There is a lot to talk about. I want to go back to the beginning, though. How did you become an entrepreneur in the first place?

Wow. We're getting right, right into it. I started my first company when I was relatively young, 13, 14. Did well, low six figures in revenue. Meant that I was not focused on my homework, as you would imagine. I think when I'm asked the question of why, why did, why did you start the company? My pop was a single dad, a lawyer. He took incredible care of me and my sister, always providing. And I think that I just wanted to work like Dad. You know, I saw him at his computer working long hours. And that entrepreneurial spirit, that work ethic was always, always there. I think that a more interesting question now being on, you know, the second large startup is why do you keep doing it? And it's interesting. I think that what I've, what I've narrowed it down to is about pride, like I love to make our customers proud. I love to make the team proud. I love to make myself proud. And I think that that's ultimately why I wake up every day and I'm so excited to get to work there.

I know you said at one podcast you had this like 80-page document or something like you like go through to evaluate ideas to like months and everything. What are some of the things in that document in terms of what you use to evaluate an idea? Because you've started multiple companies now, like Tell me more, more about that.

Yeah, so I think the first thing to understand is that when you start a company, you're effectively signing up for a pretty meaningful life chapter. Think at minimum, if you really see it through, so you don't quit early, call it 4 or 5 years. If it fails, you can even have some circumstances where it fails at like the 10 or 15 year mark. And so you want to be really, really careful. The other thing is that I've had this idea recently. I've started to get chess lessons from this grandmaster. And to be clear, I'm not very good at chess, but I did find that like— Yeah, not yet. But I did find out that you can get lessons from grandmasters. And I'm like, what a cool experience to like train with someone who's at the top of the game. And I was going through this puzzle with him and I was like, "So when is it going, when are we gonna get to the point where it's like easy for me? Like when everything's easy?" And he stopped and he said, "John Andrew, it will never be easy for you. You are always gonna have to try." And I began to think about this idea that there are certain things, endeavors in life, so bringing everything back together, that are these long chapters until you find out what the outcome's gonna be. And there are also initiatives or endeavors that are very, very low probability of success. And so what that means is, is that number one, you have to try, which means you have to be strategic and thoughtful. If you just wing it, then you're not going to have a successful outcome. You're going to fail. And so when it comes to building startups and companies, your odds of success are exceptionally low. And so you have two choices. You can either be very, very thoughtful and strategic about what am I going to do, how am I going to do it, you know, what is my strategy, my customer acquisition strategy, my growth, you know, what are the potential failure points? Or you can just like be like, I'm going to wing it. Ironically, I think that so many founders and for whatever reason in our current culture, we celebrate this idea of like, just wing it, like, just get started, just do it. And for me as a founder with so much scar tissue, I'm like, no, like, like, don't, please don't. Yeah, don't, don't just do that. Like, I want you to go and I want you to start something and pursue your passion, but please be thoughtful and strategic about what it is that you're building. Because even if you're exceptionally thoughtful and smart and, and see the future beautifully, you're still probably going to have tons of ups and downs, tons of challenges, tons of pivots. And so regarding your point, one thing that I did when I was starting Wander was create this sort of pre-mortem document. People are familiar with the post-mortem process, which is something fails and then let's figure out why it failed. I wanted to start it with this idea that, you know, I was 23 at the time. I had just left my previous company and I wanted to make sure that this next chapter was going to be successful. And so I created this document. Effectively, it starts to look like a business plan where you have all the different risks in your business, in your idea. And what you do is you start working on paper through them, and ultimately you reach the point where hopefully, if it is a good idea, that you need to go out into reality to find out if it actually does play out the way that you think, which is great. But with a lot of ideas, you can actually kill them on paper. And I think that killing your idea on paper is way better than saying like, let's wing it and waking up in 5 years broke and tired and being like, shit, like if I had just been slightly more thoughtful, I could have saved a lot of pain and a lot of money.

What were some of those things with Wander in terms of obviously you had to think through that as in the early days of starting Wander that could maybe kill this or you want to do?

So, Wander, Wander is an exceptionally complex company that serves a relatively simple customer problem, which is basically when you rent a vacation rental, we want you to have a really great experience. I think everyone has those Airbnb horror stories or bad vacation rental experiences. And so, it's a simple problem to solve. The solution to it is radically complex. You have this idea of building a booking platform, you have to create a strong consumer brand, you have to identify the brand standards, the curation of the underlying inventory, And then you get into this really challenging problem, which is how do I create a customer experience that's 3 times better, 4 times better than Airbnb's, but has the same margin profile? And so you have to build this incredible software layer. And so as I was going through and architecting this in my head, I, I looked like a madman. Um, but that actually is why I fell so in love with the idea of Wander was because I had this childlike excitement and curiosity. And I felt like I was uniquely positioned. The idea felt to me as if it was this gift and like I was the right person to bring it into the world. And so, you know, for Wander, there were tons of failure points. Oh my gosh. I mean, marketplaces are incredibly hard to start. You have a cold start problem. You have to identify your network effects. Even if you think about the brand of Wander, Wander.com, @wander on the social medias. How do you get that?

Yep.

There were so many different risks, but again, I knew how to do it. I knew how to navigate through the solutions and now we're at the point where we've hit product market fit, well over 100 people, scaling very quickly. And so I think that fortunately those early stage risks have played out in my favor and thanks to being highly strategic and agile and of course you also have to adapt in real time to when things don't go well. And now there's a whole new set of risks, which is, you know, scale and continuing to deliver value and those different pieces. And I'd love to say that that document has gotten, you know, all the way to this point, but ultimately we are now in uncharted territory. And so I find myself every day going through that same paranoid process.

I want to go through more of the scaling part because it's incredible what you've done and obviously you keep growing, so it's more problems that come potentially with that. But in the early days too, like going through that document, looking at all these different things you could be doing, you're mapping it out, you're being very intentional about this, very strategic. What are some of the first things that you actually do? Are you like, okay, I know I want to do this idea, I need this like co-founder, I need a founder to do this, I need to raise capital immediately. Like what, where do you even start? Let's just walk through that because I'm really curious.

Yeah, so I'm a solo founder. And so, you know, the co-founder piece was something that wasn't on my agenda. However, building a team certainly is. It's very hard to build a great company alone. And so, you know, when you think about if I was to define like what is a roadmap for a founder who's getting started, how do you actually go and do it? The first thing that you do is you have an idea, maybe you have multiple ideas. The second thing you do is you pick the one that you're most passionate and excited about. And to be clear, No one should ever say like, I want to be a founder and now I'm going to go and search for ideas or whatever else. It should be very much the opposite. Yeah. Which is, I'm curious, I'm excited, I'm passionate, and now I'm going to create a company from whatever that item, that thing is. So the first thing you do is that idea finds you, hopefully, and it compels you to the point at which you are ready to spend 5+ years of your life building this thing that may not work out. And that is, again, a very, very important thing to know is that the idea, the calling should be so compelling that you're willing to risk it all. And when you find that, then you start all of the classic checklist things, which is, okay, I know that I'm going to need to register. I know I'm gonna need a domain. I'm gonna need to set up my G Suite and my bank accounts and all these various things, the basic infrastructure, payroll, et cetera, which nowadays is very, very easy. I could name 5+ random providers that can do all those services for you. I'm sure that some of them should sponsor this podcast.

Thank you, Ro, for being a sponsor.

Yeah. And so, and then it's a question of, okay, what— when I look at my premortem document or my plan, you know, what, what are the key risks and what are the things that I need to start building to prove them? And when, you know, for Wander, literally my first question was Does anyone want what I'm building? And so what we did is we created a website that, and this is very common, well before you have anything where, you know, you talk about what you're building and whatever else and see if you get signups. But I took it a step further and I wanted to know if people would actually pay me to see if they were going to be interested. And so we had a section of the waitlist which was $100 and you would get a Wander hoodie and first access to the platform and $100 in credit. So it wasn't like the money was evaporating, but yeah. You had to trust us. And we did $200,000, $300,000 in revenue in like the first month or two that that was live. And that's when I knew that we were really, really onto something. Like this was like, okay, like here we go. Then you get into, you know, for us, we needed our first homes and, you know, all the chaos, of course, around that. But again, if you go back to this idea of planning, which I think is super underrated, you should have really incredible clarity on what are the things that I need to do? How do I need to de-risk this business? How do I get from here to there to there? And as you go, you also need to understand that action will, will create clarity. And so as you move forward, if there's something that's unclear, as you walk towards it, you may get slightly more clarity on, you know, the step after that and beyond.

How did you guys go to market?

Yeah, so we have two. When you say that, do you mean how do we launch or how do we get our customers?

Even in the early days when you mentioned you had like a couple hundred thousand in revenue. From like even like the 100 hours, how did you even just, let's test some Facebook ads, let's test some Google ads, like take me through that.

Yeah, so the first thing you start with is very, very low scale, which it should just be your Twitter or X. You should just start talking about what you're building and tweeting things and hype and quotes and whatever else, screenshots of your product, and see if like you get any likes, even if it's like just some like random friend or whatever else. As you go, you should start to feel some type of signal, some type of movement. And, you know, from there for Wander, you know, the thing just kind of caught fire a little bit. I knew the low-cost channels to create, you know, some levels of excitement, you know, create a launch video and those different pieces, which is again, what I would recommend is you start on Twitter, then you have a company Twitter, you release a launch video and you see what the reception is. And we see that all the time. We see new products launching on Twitter all the time. And if you launch it and people are like just super unexcited, then, you know, there may not be idea-market fit. And that's not to say that your company and your product can't be successful. There are tons of stories of people who had ideas that everyone thought was dumb, that no one wanted to do. And it took years and years and years until the timing caught up with them. You know, for Wander, we were building the right product at the right time. So we had a recipe for success. But to be clear, that does happen a lot with founders and startups is that you actually have the right idea and you are the right founder to build it. You're just starting it 5, 10 years too early and you have two choices. You can either have conviction and stick it out or, you know, you can abandon. I think abandoning is really tough because in 5, 10 years you'll see someone become a billionaire on that same idea, which of course are probably a lot of, a lot of listeners with stories like that.

Of course. And with Wander as well. So with your previous company, you had raised a bunch of venture capital, had been pretty successful with that. Did you have that same kind of prep doc for that, that you then, okay, I'm just doing the same thing, or like, was this a lesson learned, repeat founder now?

Yeah, so I started my first venture-backed company, Coder.com, when I was, you know, 17, 18. And as much as I'd love to say that 17, 18-year-old John Andrew Entwistle was as thoughtful as I am now, I was not. I certainly had a ton of, raw intellectual horsepower. Yeah, but I did not have any level of experience that I do today. I've been a venture-backed CEO now for a decade, which is a crazy— that's wild— statement. And so a lot of that was the learnings and lessons through, unfortunately, a lot of scar tissue building my first company and knowing that, you know, in that first company started at 17, 18, you know, I grew it all the way through growth stage, you know, massive customers, Vanguard, Goldman Sachs, Palantir. I ended up stepping down as CEO when I was 23. And like, that was 5 years of my life and 5 years all-encompassing of my life. And so I knew that, you know, the risks when you do go and start something new because it flies by and success again is not guaranteed.

Yeah. And that's so crazy to go at such a young age, too. And with the Thiel Fellowship, so with that as well, I know at that young age you don't have many peers. There's not many people around you at that age that are like building venture-backed companies. Is that why you became like part of Thiel Fellowship? Tell me more of that side of it too.

So the Thiel Fellowship, for anyone who's not aware, is a program that was put together by Peter Thiel where effectively his original thesis was that you had all these young individuals who had great ideas and great capabilities who were kind of getting sucked into this societal engine of going to college and going through through this motion. And he believed that if you gave them capital and you gave them an opportunity, that you could have a proof point that you don't need to go to college, you don't need to go through school to end up building something successful. To be clear, whether you go to college or not go to college, I think that debate is not one really that should be had. Like, I think it's great. You're a founder, you're an entrepreneur, you're learning. Everyone has their own pace. Like, it's very exciting. We should all be in this together. You know, but, but for me, I started Coder while I was in high school. I knew that I wasn't going to college, and that was a very, very contrarian idea at the time. I think that, you know, nowadays you have some proof points where you have some acceptability of, oh, you're not going to go to school. Like, you know, there's some communities that embrace that. Yeah. But for the most part, back then it was not loved. And certainly today still it's not loved. I think there are probably lots of founders and entrepreneurs who have parents that that idea would never be acceptable. And I was super lucky that my pop was very, very supportive. And so the Thiel Fellowship was really nice for me because, you know, when I joined, we probably had 30 or 40 employees. I was, you know, 21 maybe, and I was very alone. Like, I was building this company. My peers were far older than I was. And I felt the weight of that. And the Thiel Fellowship was really special to me because it was the first time that I met kids who were my age building incredible things, who were in a similar phase of life.

Yeah, I love that. And coming back then to Wander, so you had this experience before of another venture-backed company, used that, you're way more prepared this time around. It's still gonna be hard though.

Totally.

Take me through some of those early days in terms of, okay, we got to find the homes. What locations are we going to choose?

Where?

How much funding do we need to do this? Like that piece of it, I'm very curious about.

Yeah. So we had the idea and then we needed the first few pieces of inventory and it was as unscalable as getting in the car and going and looking at houses. And I knew that from a speed perspective that the fastest way for us to kickstart would actually be to own the first few assets on balance sheet. Which to be clear is an exceptionally capital-intensive idea and very, very unscalable. There's a classic, you know, YC quote, which is do things that don't scale. And I thought that it was the fastest way to basically create this ultimate experience and see if these paying customers on the waitlist would actually pay for a product, because that was the next thing that I wanted to know, right? It was basically like, are they going to pay for the product? And then I'll figure out how to scale it. But like, let's go down these these, these levels of problem solving. And so, like, when you think about this idea, I had gone from, you know, growth stage CEO, you know, having raised $50+ million at 23 to pre-seed starting Wander. And literally, like, when we were launching those first houses, I was there 24 hours a day scrubbing the floors, like, understanding the cleaning crews, trying to think through how the software would work. While also raising capital. You know, my early, early team members have photos of me walking around random gas stations in the middle of nowhere with my laptop, taking, you know, VC calls and pitching them as compellingly as I can and then immediately turning around and like solving what were really small fires at the time relative, but were the fires that would burn down, burn down the company. Obviously, like, things scale really quickly. You go from 1 or 2 locations to, you know, 10 to 30, and then, you know, all of a sudden you're at 1,000 plus, and, you know, who knows what's next from here.

Oh, it's gonna keep growing. Do you think, I guess I'm curious on why you think it hadn't been done before in this particular way, because you have the Airbnbs out there, you have other ones that are doing a different angle of it. This vertical kind of integration of doing everything, What do you think about in terms of why it hadn't been done?

I think that it's really hard. And so, like, what do I mean when I say that? First, you have to build a booking platform that's an incredible user experience that rivals really great companies that have spent literally billions of dollars building their platforms. So Airbnb, VRBO, you know, Booking.com, etc.

Yeah.

Then you have to create a brand. So, you know, I knew that brand was going to be one of the limiting factors in building this company. And so I had to find and invest in one that would scale, that wouldn't be a bottleneck. And so we ended up getting wander.com, @wander on the social platforms. That's an incredibly difficult challenge to build a really beautiful, meaningful brand. And then you end up with the supply problem. So the go-to-market, how do you get the supply onto the marketplace? And then you, you take it a step deeper and you say, how do I enable a margin profile that is really scalable, that scales at the speed of software. And for me, I had this vision that property management was effectively this, this logistically heavy, human-heavy business that could be done by software. And so we wanted to build this agentic property management software that we called, now that it's fully built, WanderOS, that actually coordinates all of these vendors, cleaning crews, you know, handymen, does intelligent pricing. Calendar management, chat management, all the things around it. And so, like, if you imagine me pitching you this idea as a pre-seed investor, you would think that I am absolutely nuts, like 100%. And I was like, the only people who backed me were previous investors of mine. Redpoint had seen me build a coder. They let our pre-seed, you know, I had friends who had seen me build, other founder friends, they had invested in me. But candidly speaking, I don't know if I would have been able to convince anyone to back me if it was my first time. It was such an ambitious idea. So I think that's why it hasn't been done, because like it is crazy. And candidly speaking, like, I don't think that most founders have the skill set that can cross between software and hospitality and go-to-market. And those experiences are something that it's not like I just came out of high school with. A lot of them I borrowed from the growth that I had at Coder.

That— yeah, there's a lot to unpack and a few different things. Like, obviously, a repeat founder is very helpful in this particular case. Like, you needed to be a repeat founder who had that skill set to then have it and have the desire to want to build this company for it to work out. And obviously it's worked out. You put a lot of work into that. One thing you talked about before is the brand piece of it and needed to get that right. I want to unpack that a little bit. What were some of the aspects that you thought of? Obviously getting the domain name. Just tell me, take me through more of that, like how you thought about, okay, do we need to bring someone on board to kind of help this? I want to know more about that side of things.

Yeah, so a brand is effectively a promise to your customer. That's what it means. And so when you think about that promise, you have to be very explicit in terms of what do I stand for, what do I want people to think and to feel? And that can sound very wishy-washy, like this idea of like, well, what do I want people to think or feel when they hear about my company? But you really do want to be very deliberate. And when you think about that, then things like your name, your logo actually come from that idea. Like for us, obviously we're building a travel company, but I didn't want to call it like travel.com. Like there's no feeling in that. It's like you are, you to wander, like is such a beautiful word. It's so great. And I wanted to build a company that would also honor the beauty of that word, like from a soul perspective, that like, that is such a beautiful word. It's a beautiful meaning. And the feeling that you get, like we needed to deliver on again that brand promise. And so, you know, then you get into the logo and it's like, well, how do I want people to feel? And I remember as a kid spinning the globe in class with all of this childlike curiosity and excitement about where am I going to go? And so I knew that that was going to be the logo, which all of our designers, everyone— well, we didn't have lots of designers. We had one contractor at the time, very early stage, was like, it's not going to look good. It's not going to look good on mobile. It's not going to be scalable. You should go with what everyone's doing for the mainstream. And I was like, no, like, this is how I want people to feel. I don't care if it's going to be more complex. And ultimately, I think that, like, I do love our brand. I do love our logo. It has stayed the same from starting the company to now, 4 years later. And I think that it looks classically strong enough that it will hopefully, you know, stay, stay very strong 100 years into the future. But that's how I think about, how I think about branding.

I mean, it seems like the branding is perfection. Like, you see it on, you see it anywhere on social. Okay. The images, even like having like the moving background now on the app, like that addition too.

Oh, I'm so glad that you like that. That was like me. Yes. I was like, I'm, I am very in the weeds. I'm very product and design oriented. And so on some of the properties, not all of them, but on some of them, when you hover over the image on the property page, you'll see the sky move, you'll see the trees move. And so you— I was inspired, um, because I think we all watched Harry Potter as a kid, and there was that scene where, uh, the newspaper would like come to life. And I was like, how cool would it be if you're on this website and all of a sudden The image comes to life. Like you're not expecting it. It's a little, a little piece of delight. So it makes me really happy to hear at least one user likes it because it's like, that's one of those things where like you have this crazy product founder who's like telling like the team and designer like, hey, like I have this idea and it's like not going to generate any revenue at all, but maybe it'll create some type of delight. So that makes me very happy.

But it is literally a talking point. I mean, I looked at, I obviously do a ton of research for every episode and I'm looking through more more and more of Wander. And I've followed along for years, so I have seen the progression a bit. And then seeing that, I was like, wait a minute, that seems like it's new. Little touches matter. And obviously you're an experience company. Like, this is at the end of the day what it is. So like every experience from the beginning to someone seeing you, to them booking and then having to stay, and then they're done. Like everything matters. And that touch is one of them.

Yeah. It's funny that you say that, that term, everything matters. So that's actually one of our virtues in the company. Is everything, everything matters. And when you, when you have that philosophy, everything from any unhappy guests to optimizing your expenses to designing a beautiful user experience, you end up with this level of focus and love for your, for your product and for your company that I think is really special. I think that one other virtue that I would recommend any founder who's pursuing that idea to align it with is is we have a virtue, which is no one is coming to save you. And what does that mean and how did it come about? When I was in the first house and we were gonna launch in 24 hours, things were a mess. There was a ton of work to do. And I remember being there with the team and saying, "No one is coming to save us." like if we don't do it, no one else is going to do it. Like there's no saving grace. There's no, like, no one is coming to save us. And so when you pair those two ideas together, that everything matters and that no one is coming to save you, then you feel this sense of agency and responsibility that hopefully can build a beautiful company.

Well, it reminds me too of Izzy Sharp from the Four Seasons and him saying, like, you know, excellence is the capacity for taking pains. Like, that is exactly what that type of detail at Wander reminded me of. And so I read the book recently, his book, which is phenomenal.

It's on my reading list.

I haven't read it. Oh, based on the company you're building, that is like the perfect— because every detail they go through and how they progress and everything is phenomenal.

I'm really looking forward to it. Yeah, I think it's literally on my bookshelf. So it's—

that's amazing. Sitting on my desk, actually, in my apartment. And I loved it because like it is all about details with them. And how do you build Four Seasons, for instance, like this massive conglomerate?

Like, totally.

But it's all in the details. And that was how they stood out. One thing is you mentioned with kind of owning the homes, obviously, like the first couple of ones you bought, and then you want to see if people will pay for that. And yes, they paid. But take me through more of that, like first reaction when you actually had the homes. What was some of the feedback you were getting? And you're like, okay, were we right within this hypothesis? Were we wrong? Like, tell me more of that.

So Wander, Wander did something very unconventional, which is that we built the most extreme version of the customer experience. At the start. And then as we needed to scale, we kind of pulled it back a little bit while making sure that we didn't see a big degradation in the Net Promoter Score. And so when Wander launched, every possible epic thing you could imagine existed. Like you could control the entire home right through the app. And so like turn on and off the lights, unlock the front door, like turn on the music through the Wander app. You could unlock the Tesla in the garage.

Crazy.

You had all of this, all this beautiful design architecture. At the time, you could ask concierge to do anything. You could say, hey, like, book me these experiences in a private jet and whatever else, and concierge would do it as if it was your personal executive assistant. The reason why we decided to do this, and to be clear, this was with a team of 10 people, so this wasn't like, oh, we had 100 people. This was like, I wanted to show the world what we were capable of, what things could look like. Now, to be clear, those systems were super, super janky. It wasn't like we built this like hyperscalable smart home tech system. Like we built a wrapper that like janked through the API of like SmartThings as an example. And with the Tesla integration, that was actually like pretty, pretty well built because, you know, someone from Tesla like gave us access or something along those lines.

Nice.

But, and Concierge was like, you know, some of those requests were like me, like handling whatever it was. But what I wanted to do again was gain, you know, this understanding. And so, what was really cool about that is we started at the extreme, we found product market fit, we found idea market fit, we found something that people were willing to pay for, and then we entered into that next question of like, how do you scale supply, what pieces scale, what pieces don't, and then we walked back from there.

The WanderOS that now you can call it WanderOS, early on obviously you're figuring out more of these things. Like, how do you even like begin? Because you think about the cleaning and everything to organize. Obviously in the early days it was not, that was not the case. You didn't have it like fully fleshed out, but you probably had an idea of what you wanted to get to in terms of that.

Totally.

What was the timeline or even like just the progression of that to get to that point?

Yeah, so I viewed this idea of having to achieve a very high margin profile, having to have it scale at the speed of software as a have-to in the business. And so then the question is like, well, how does it work? What would the system be? And you kind of work backwards from there, very like first principles thinking. And so what I saw was effectively logistics management and coordination, which is I need to get a cleaning crew to come at this date, at this time, and complete this list of things. And there's no reason why that can't be software and AI, which very early on was a hypercontrarian idea. I mean, now everyone has a thesis about how AI is going to do everything and you can coordinate you know, all these things. But when I was first starting, it was seen as like impossible, insane. And I still think a lot of folks feel that way. And so, you know, we got to work and I would say that it took us, obviously we've been building software the entire time. It's, you know, my background and our CTO is fantastic. But now we've reached the point where 100% of tasks are coordinated through WanderOS, which is a pretty meaningful, meaningful thing. And we have about a 60% deflection rate with AI agents, which means that 60% of those tasks are being coordinated and handled automatically via these agents. So think scheduling a cleaning crew, dealing with a payment, responding to a guest. And so reaching 100% deflection rate, or let's be realistic, like a 95% deflection rate is something that is now possible. And it's what enables our margin profile. We have, you know, 70% plus gross margins. In a business that absolutely shouldn't. We're able to grow 20-30% month over month in a business that should be growing 20-30% a year. So, you know, that idea ended up working out. And candidly speaking, if I had failed in that endeavor or if I didn't know how to build or whatever else, then Wander wouldn't exist as it does today.

Well, it reminds me of a George Mack essay he just wrote about high agency. He's like, does it defy the law of physics? And if the answer is no, then it's possible.

That's so funny. So I wrote that in my first investor update 3 years ago that wander was a big idea and ultimately it doesn't defy the laws of physics, so it should be possible. That's literally in my first ever investor update. So that's great to hear.

It also reminds me, 'cause I've done a lot of research on the kind of world-class founders, like Jeff Bezos mentioned one time, he was saying like, when people come to him with ideas or like something for products that can't be done or can't be done, They come to him basically saying, we need to do this thing. He's like, show me a magical product and how we get there. Don't give me problems on that. It's like, what is the magical experience? And then we'll figure out a way to make that happen.

Yeah, it's like working backwards. Even like you think about some products work backwards from cost, which I think is also really cool too. Like this idea of like, what is the customer experience? Or like for Costco, they work backwards for like, what is the price that someone would pay for this and work backwards? And so I think it's all, I think it's very interesting to think about working backwards which comes back to how we started this podcast about planning, which comes back even further into the idea of like planning backwards from your death. Like, yeah. And so I think that it's a really important idea. It's like founders should be working backwards. They should know what they want to do. And ultimately, like, that will help you conquer the maze a lot faster.

With those first few homes, how are you deciding on locations?

Yeah. So the first home I knew I wanted to be outside the Bay Area, and that was purely strategic, like tech was all in the Bay Area. And so, like, you know, I wanted to establish Wander as this, like, new, exciting startup that was coming to light. The third location was a little bit north, about 200 miles north, and then we immediately went across the United States all the way over to New York. The reason why I did that was because I wanted to prove this idea that Wander didn't need any type of geographic density to operate the units. I wanted every piece of software and system that we built to be unit dependent, independent, because I knew that hopefully one day that we would be adding 200, 300, 1,000 homes a month. And if the systems weren't based on the individual units, then I would end up with having to re-architect the company every single time we hit a new milestone. And so that's how we thought about locations originally. Now, today, you know, we'll probably add 200, 300 homes this month. You know, it really is about curation, data science, you know, a lot of very technical ideas. But soon, you know, we'll be well beyond the US into Europe and the rest. And that's something I'm so passionate about is to fulfill like the logo's like quote unquote prophecy, right? Like the logo is the globe and it would be really beautiful to actually have locations all across the globe.

What complexities come into play?

With international—

yeah, international.

So international expansion is very expensive, and I learned this during a talk once where a founder was looking to expand into Europe, but they were expanding at the tail end of their Series B. So they had raised all this money after their Series A, you know, and then they start building, and then they're like, okay, we're going to approach our Series C, let's expand into Europe ahead of our Series You'll see, it'll be a great growth story. What ended up happening is they didn't have enough capital to, to conquer Europe and ended up having to pull back. And so they wasted all of this money. They killed their growth story. And that left them in a very dangerous position where ultimately they had to make major cuts and whatever else. And they still have not expanded into, into, into Europe. So you're looking at a mistake that ended up costing them at this point, probably 4 or 5 years from a momentum perspective, from a fundraising perspective, from a customer perspective. And what I learned was, you know, listening to him talk about this experience was that when you go into international expansion, everything is going to cost twice as much as you think it's going to cost. And you need to go in with an absolute war chest with the idea that, like, we are going to conquer it, we're going to be able to prove it out. And if it fails, that the company is still going to be okay. I'm not going to have to pull out from a place of weakness. I'll pull out from a place of strength. And there are plenty of stories in this. When you look at Facebook, Facebook has never been able to get into Russia. Mm-hmm. Uber was never able to get into China. They were able to get everywhere else, which is of course amazing. But even the biggest companies failed to get into some of these key regions and they had massive war chests. Yeah. And they still failed to do it. So, when I hear, you know, young founders or founders who aren't well capitalized talk about, you know, international expansion as their growth tactic, that's a lot harder than you think. There's a lot of expense, a lot of complexity, a lot of legal, a lot of administrative that just will cost you far more than you think and take twice as long. And not to say that it's not a great way to think about the future, but you need to do it from a place of strength.

We talked a little bit before about timing. Why is the timing now in terms of expansion and why not a year ago? Why not a year from now? Like, just tell me anything more of that.

So I think that, you know, Wander was born in 2021 where you had obviously the COVID was sort of, you know, in full sweep. People weren't staying at hotels and everyone was staying at a vacation rental. And what that meant was, is that literally almost the entire world had a bad vacation rental experience at some point. And And so you had this massive growth in the industry, you know, great occupancy, et cetera. But then you also had everyone kind of develop a little bit of a distaste. And so you had that, I think, you know, from a customer and demand perspective, but then you also had a very early special moment in time when it came to technology, when it came to, you know, this intelligence, you know, from an AI perspective that just didn't exist before. And we started leveraging it exceptionally early. We were, we were using it very early. I saw what the curve was going to look like. Like now today I think that everyone is like, ah, yeah, it's so, so obvious. But it was a very, again, a very, very contrarian statement. And I'd say that those two things, those two why nows are really has been what has allowed for Wander to exist. But to be clear, I think that a lot of it is again, just that like even if someone had the idea for this company, that it is so radically hard to put together. That I have always felt again, like the idea was like bestowed upon me as this like thing to build and to protect, like almost like it is a privilege of mine as opposed to something that is or was my creation. Like I imagine it just floating around in the universe and I just like got picked with it.

I mean, to that point, do you feel like this is your life's work or do you believe in that? Like tell me more.

Yeah. So it's a great question. So my, I've recently gone through this like reflection, you know, I just turned 27 and you have to ask yourself like, you know, what, why am I here? What am I doing? And I decided that my life's purpose was like massive good. Like that's what I wanted to align myself on. And I may fall short of that, but that was the idea. Like I wanted to create massive good in this world. And so, you know, you have a personal perspective with that. And then you also have obviously like, your work as part of, you know, who you are. And, you know, when I think about Wander, like Wander is like my heart and joy, it's my entire soul. Like I have the logo, you know, tattooed on my wrist. Like I love this company and I love the people in it. I love our customers and I'm so grateful I get to work on it each and every day. And so it would be an honor to be the CEO, to take it all the way from here to IPO and hopefully from IPO to you know, being one of those like really large legendary companies. But ultimately, like, that is a privilege, not a right. I have to work each and every day to improve, to, to stay in that seat. Um, and so that's, that's how I think about it.

When did you get the tattoo? How early?

As soon as the logo was completed. Um, I got the tattoo. I remember getting the design file while I was driving up Northern California. I was with our chief of staff. Who was sitting in the seat next to me, and I was like, you know what we should do? We should like commemorate this moment. Pulled off into some random tattoo parlor in Northern California and got it done. You know, I think that I saw, which is hard to believe, but I saw where this company was going and I wanted to wake up each and every day and like be reminded of that and my dedication, you know, to it. You know, I don't necessarily advise people getting tattoos of their company logos, to be very clear. So I don't want this to be like romanticized because it can definitely— you could end up with a bunch of tattoos of things that didn't work out. Here's all the companies I started. Yeah, but candidly speaking, I was like so compelled and so in love And still, still very much am.

So you mentioned massive good. Where does that come from, you think?

I think that, you know, in my life, early childhood, etc., like I had a lot of difficult things and those difficult things ended up allowing me to see the world either through two lenses. One of, you know, everything is terrible and the world's against me and whatever else. Or I could see it through the other lens, which would be like, the sun is shining, the world is spinning, you know, like I'm alive. And what ended up happening is like, I have brainwashed myself so much into this state of like gratitude and joy that I find myself just like wanting to, to, to do good, like, onto, onto others. And, you know, at the end of the day, like we do, we do all die. Like there's no question about that. And so you can't take your money with you. You can't take your fancy car. You can't take your private jet. Like what, what, what, what do you do? And I think that you should work because you're passionate and you can, you can also work for like those fun things. It's great to have a goal. You know, if you love cars, like go get, go get a great car. But I think that like for me, the most fulfilling thing is like doing good, like trying to do good for fellow man, for the world. It's a very like abstract idea, but I think the fact that it's so abstract is something that'll keep me busy for a long time. A goal that is impossible to achieve.

Yeah, no, I like it though. It's nice. I think, and one of the things I wanna go back to, we kind of have this whole story of Obviously, it's been crazy, like, to the growth of Wander over time. And we talked before the interview kind of started about how much you've grown and the capital coming up too, as well, which is going to be exciting. The funding this business, we— you have a massive idea. You're a repeat founder. You're young, but you like know what you want to build. Funding it, you had the pre-seed. They believed in you. Couple companies. You obviously then had to grow from there.

Totally.

What was the next round? Take me through more of the funding side of it. When did you like get the proof points where you're like, okay, we can actually continue this thing. Like, tell me more about the funding.

Yeah. So the way to think about funding is milestone-based. And what you're trying to demonstrate to investors is that you are able to execute and the idea is working. It's those two, two pieces. And so there are different milestones at every round of funding. They're generally relatively prescribed. So you don't even need to guess. You know, at the pre-seed, people are looking for your company to have a name, they're looking for a really good pitch deck, and some proof points of idea-market fit, and maybe an early prototype. Those are the things that they're looking for. The second phase, your seed round, you're looking for a platform that exists, that has users, some level of progress, and some level of customer love. Maybe just like one or two customers who are willing to pay, who are really excited. Okay, great. And to be clear, you still have to go, you have to to pitch, you know, all that sort of good stuff. But okay, you have unlocked your seed. Now you have to get to your Series A, which typically is milestone-based from a revenue perspective. So, you know, it used to be $1 million in ARR, you know, now it's more like $2 million. And for certain companies like, you know, e-commerce, etc., it can be, it can be much more. And so then you have to get to that phase, which again is not easy. And I'm sure there's a whole bunch of other pieces that allow you, but it's typically revenue-based. The Series B is your growth round, the start of your growth round. So, you've found product market fit, you're anywhere between $5 to $15 million in AR. It used to be $5 was the Series B milestone, now it's more like $10 to $15 is generally what I would say. You know, to be clear, if you're a founder with $5 and you're going out for your Series B, then you may have more difficulty, but you could get it done. You know, and that round is the round where between your B and your C, the thing that you're figuring out is your You're absolutely dialing in your unit economics, you're taking all the recipe for success that you have and you're bringing it together, and you're proving to the world that this is going to be a real company. Your C is basically taking something that's real and tripling it, quadrupling it, and then you're going to go an IPO. So, the Series B, I think, is probably the hardest round. It's actually certainly the hardest round. I think that I've slept, you know, I got 6 hours of sleep last night, so I'm feeling pretty great. But gosh, this last week I was running on 10 hours of sleep cumulatively. Oh, and it was so, so rough. But I'm so, so lucky. I have a great team and fortunate that people have enjoyed the progress that we've had and, you know, and believed in me and believed in me getting through this next phase. But, you know, that's sort of how to think about the stages, you know, quote unquote, like peeling back layers, peeling back proof points, you also have to remember that you have to prove that you can execute. So it's not just getting those pieces, but that you can do it in a certain time period. So you'll see a lot of like the $0 to $100 million in ARR, like rocket ships that happen in a short period. Realistically, I'd say like pre-seed to seed should be about 6 months to a year. You know, seed to Series A, probably also about a year, year and a half, maybe 2 years. Series A to Series B can be anywhere between a year and a half to 3 years, and then, you know, it should go from there. It's sort of the level of progression that like VCs are looking for to show that I can give you money here and you're going to IPO in call it 8 to 10 year window.

So, with Series B, which you're raising now, let's say—

We just signed our Series B term sheet.

Just closed, love it, amazing. So, by the time this is live, we can also—

Yes, you're getting it very live. I am in the middle, I'm in In the middle of the process, just signed the term sheet literally like 2 days ago. And then obviously you have all the chaos that flows, flows around that.

Yeah. So you're still like, yeah, sleep hopefully gets 6 hours. Phenomenal. We're getting closer to 8. Is that ever a goal actually, or?

Yeah, totally. I mean, I am very like, I don't want to endorse this like hustle idea of like, don't sleep. I think it's terrible. I think you should totally sleep. I'm just in a period in the company where I literally don't have a choice. Like if I do not give my 100%, then failure is totally an option.

Well, and also to that point, so with the Series B, let's set the scene. Where is Wander today at the Series B?

Yeah, in terms of—

Like how many locations or like team size, anything you can say.

Yeah, so we just crested 1,000 locations. We've been growing 20-30% month over month, so you have to take the growth rate into account. We have about 100-ish people, a little bit more. Our net promoter score is 85 for Q1. And we should finish out the year at about anywhere between a $70 to $80 million GMV run rate.

Crazy, man. Crazy. Take me through more of the scaling part of it then. I know we're getting towards the end of the interview here. The scaling side of it, you have the early days, your proof points, and obviously you've raised money, you've progressed. 1,000 locations is insane. Take me through some, what has been helpful on scaling, more of that process for you, anything you can say around that.

Yeah, so there's this idea that Nigel Morris, the founding partner at QED, talked about with me recently, which is code cracking, right? You have certain things in your business that you have to unlock to get to your next phase of scale, and that ultimately takes a certain type of individual, your like code cracker, who, as he noted, is not the same type of person who will go and potentially scale it, right? Your code cracker could be different than than the scaler. You know, for Wander, there are so many things. It probably would take us 3 hours to go through all the, the code, so to speak, that we had to crack to unlock this level of scale. I would say that I do know now how Wander can go from 200, 300 homes a month to 1,000 to 5,000 to 10,000. And like, oh, I should say 5,000 to 10,000 is probably a lot. That seems like a lot. Yeah, there's a lot of— there's some code cracking there for sure. So I'll go back to 1,000. Well, 200, 300, 1,000 seems more reasonable. There we go. But yeah, it's a joy. It's something that ultimately like you have to love. Like one of our virtues is we love problems. And that's because at the end of the day, literally we wake up every day and we solve a problem that then creates a new problem.

Like, more customers, great. Then we have to solve it.

Yeah, new problem.

Yeah, exactly. And where does the REIT come into play? So you did one for, I think it was like 2 years or something. Is that part of the bigger strategy when you have to go bigger? Like, tell me more of that.

Yeah, so it's all about the progression on the supply side. So Wander started owning the initial assets on balance sheet to control the experience, to learn very quickly, to understand how the coordination with vendors worked, how, you know, we would need to set up the owner dashboard, all these different pieces, and ultimately to find product-market fit. Then the next question was to start to scale. And so we knew that we weren't ready to have third-party inventory yet, but we needed to have a way to scale without spending our own capital. And so the idea was to basically have investors own a piece of these homes so that we could go and add more of them without losing control. And so that's where the REIT came in, was, was that idea. The REIT ended up scaling to about 35-ish locations, which is actually pretty large on like a real estate— from a real estate perspective, from like a total capital perspective. But at that point, we then had maturity of the system, maturity of the brand, and we started to have these, you know, these owners who owned the homes who were saying, hey, like, I trust you now. I'm willing to give it to you. I'm willing to let you, to let you operate it and to grow. And so, once we had reached that point, then the REIT investors had a very successful exit, you know, 22%, you know, cumulative return, which is great in the real estate world. And we were able to start scaling entirely asset light, which is a requirement to have this level of scale. This is also why I think that it would be very, very challenging for anyone to try and build a competitor to Wander in this context, because solving the cold start problem is like a very, very radically hard idea. Like to go from owned to investor owned to then operated and is just a very complicated piece. But that was the, that was the only way that I saw to post year-over-year growth while still maturing the company and peeling back those layers.

You know, the thing that's interesting, I had Jacob Jaber from Philz Coffee, co-founder of Philz Coffee, and they maybe have like 80 locations now, but he was saying their growth was a lot of pull. Customers pulled it out of them. They had the first location for like 5 years or something. Customers pull it out of them. Take me to the demand side for you then. In terms of then, you obviously know you had to expand, you raise money, you know milestones to reach, but there's this demand piece that has to match up with supply. Take me through the demand side of it in terms of that.

Yeah, so we were always supply constrained in the business. I think we had like 100,000 users and like 5 locations or something. And so Ultimately, we have now reached the point where we've— we now have about 400,000-something users on the platform, and our focus is actually more on activation of those users. This was something that I was also talking about with Nigel Morris, and I think it's such an important idea that you shouldn't only be focused on growing your user base, you should also be focused on activating them. And so, like, to use the example from a podcast perspective, like, the goal is not just to get more subscribers. The goal is to say, okay, I have 20,000 I have 10,000 subscribers or 100,000 subscribers or whatever, how do I activate them? Like, how do I get them to do stuff?

Yeah.

And so, the same can be true of the user base. Like, I'd much rather have 5,000 users who do stuff than a million users who do nothing.

Yeah.

And so, it's a very interesting paradigm shift, which again is very much going from Series B to C is it's not just about user growth, it's about user activation, which is in my opinion, a very like— nuanced idea.

No, it's funny. It's funny you mentioned that. Literally the last like 6 months has all been thinking about, oh, like all these email subscribers, always whatever. Like, how do we do more with them?

Not even just growing the top line. It's not about growing. It's about activating.

So with that, so what are some of the things you've done for that? It's just like literally just sending more emails like, hey, this— like, tell me more.

Yeah. So one interesting thing that we've recently started is effectively, you know, a user will— we have all this beautiful data. User will go, they'll sign up. And maybe they initiate a checkout on a certain set of dates, but they abandon cart. And so my question was, is like, okay, our average order value is very high. It's about $5,200, which for a consumer company is like pretty extraordinary. Yeah. And like, that's a big purchase. And the fact that people right now are just doing it through our website is like pretty high. Like, what if those people just need like a little bit of touch, right? And so a system that we've recently begun testing, which has phenomenal results, is that you go, you abandon cart, and you get this beautiful email that's like, hey, you know, I saw that you checked out for Christmas, you know, at this property at these dates. You know, I think it would be a really wonderful experience. Like, let me help you, like, walk you through the process. Do you have any questions, whatever else? Literally to the point where like our AOV is high enough that we can totally support a sales phone call, like, to that individual and make sure that they get through it. And so if you were to scale that out, like, it gets a lot more like interesting and complicated. But like that's an idea of activating your user versus just saying like, oh, we're just going to email them to death or whatever else. Like that's the, I think the lazier approach. Like there's so much you can do now with data and enrichment of your contact information and all these different things. I mean, you can even like, you know, have the email address, enrich that to a full profile and like, you know, use like a handwritten card service to like have something like You know, there's plenty of low-cost ways that you can really like activate and reach your customer.

Well, and then to your point with the data, it's like, okay, how many of those do you do? And you see, wait, we send a few like handwritten notes, this leads to how much more revenue? Like, it's insane. Exactly, right?

Yeah, and that's the idea too, 'cause again, people get so wrapped up in this idea of like, I'm just gonna spend money on Google and Facebook ads or whatever else. And like, those are really, really, good for getting the account creation, getting that user data. You know, maybe you're paying whatever, $5, $10 for an account creation. But if you're trying to just Google Ad your way through volume to call it a checkout, you could be spending hundreds of dollars from a CAC perspective, thousands of dollars, whatever the product is. And so the way you should be thinking about it from a marketing perspective is like, let me capture that user data. So you're basically buying the user from Google and Facebook. Now you know who they are, you know they're interested in your product. It's your job to activate them. Like, you shouldn't just keep spending your way and hope that, like, you know, the 100% account creation goes down to like 0.001 checkouts. Like, you really need to be focused on conversion. And that's not just like ease of flow, but it's this idea of activation.

To that point, what are the metrics you care about most?

So Wander has quite a few. I'm actually going through redefining them as we go from Series B to Series C, because you have to think about this idea of Wander has all the ingredients for success, but bringing it all together in a beautiful and high-growth way beyond where it is today is going to end up being very, very metrics-focused. And you have to think about what metrics are directly competitive to what other metrics. So like, if you have a high net promoter score, but you want to get your costs down and your margin up, like, well, you can't just reduce the quality of your product because then your NPS— and so you have— and this again was something that that Nigel Morris was talking about. For those entrepreneurs who haven't heard of him before, he is basically like the founder of Capital One, founding and managing partner at QED. He's one of the most brilliant people ever. I highly recommend looking him up. Yeah. He talked about this idea of like keeping things in balance, you know, not having a focus on just one metric, but keeping all these things in line. And that's almost this balancing act that founders have to do. And so, you know, that's my— that's really like my big focus for, for now is, you know, the basic things like MPS and your margin profile and, you know, net present value and all those different pieces. But what is the, um, what is the interconnectivity of all of those pieces, and how do you ensure that you don't lose sight of, um, you know, this one lonely metric over here while you're staring at, like, call it your CAC as an example?

Yeah, and I love the idea of activation. Like, in terms of that That makes so much sense. It's been on my mind so much the last few months and it's like I definitely disregarded it early on.

It is such an obvious, non-obvious thing because we get so focused on growth. And again, that was something, you know, for us, like we've been growing really, really quickly and we're having lots of success. But like, you know, we can take a $5,000 average order value and capture probably $10,000 to $15,000 of total spend around it. We can take an account creation that's just sitting dormant and activate it into a $10,000 LTV over a 3-year period. Like there's like, we don't need to grow. Like it's ironic, like Wander already today, like if we, really interesting stats, so our current total number signed locations and user base and everything else, if I just focused on that, is good for about $150 million a year of GMV. And that's without me adding a single new property or a single new user. Like, and so it's about that, that focus is like this activation of like who exists there today. Obviously you want to continue to grow.

Yeah.

But it's, it's more than that. And ironically, like if you focus on activation as opposed to growth, growth is very expensive. And so you can, you know, still grow, quote unquote, without growing your user base, growing supply. But very, very profitably.

I know we're out of time here. I'm just curious, where does this get to? Like, how big does Wander get, you think?

Yeah. So I guess like, first of all, like, I, I hope, I guess it's like, I hope, like, I can't, I don't want to be like so egotistical or like confident. Like, we're very lucky. We're very fortunate. We have all the right things happening for us. But as any founder entrepreneur knows, it's so much hard work and there's a lot of risks. And I plan on giving my life and soul to trying to get us there. You know, when you think about the market we're going after, it's about 300,000 locations across the globe. It represents roughly about $35 billion of GMV. And so that's our, that's our focus. And then from there, we'll be expanding into other, other products and services. But that's what you'll see from Wander in the short term is continuous aggressive growth across the globe, delighting our customers relentlessly, and then from there offering other products and services, you know, leveraging the distribution mode that we've hopefully created.

John Andrew Entwistle, thanks for your time today.

Thank you so much. It was a joy. Yeah, really excited.