How Wander Raised $50M to Reinvent Luxury Travel

33:10Like, what do you want that to look like? And ultimately, we made the decision that we just didn't have enough money to have two different development teams and we couldn't support, you know, different versions. So we wanted to have in-use frameworks that were compatible across all platforms. And we also made the decision that, you know, building in TypeScript to have a little bit of continuity between front-end and back-end teams, which to be clear for all of you who are going to like roast me in the comments or whatever else, like, yeah, like there is definitely a more performant way to build.

33:45But, you know, in the early days, you know, it's like you have like one or two engineers. And so you have to make those kinds of decisions. And I think that probably the most interesting thing about Wander from a software perspective is that you have the booking engine and the booking platform. And that's the only thing that we surface to guess. But underneath, you have what we call Wander OS, which runs 100 % of the property management tasks related to all the properties on the platform. So 100 % of all the operations are being coordinated remotely with third-party vendors actually doing the underlying tasks.

34:25And I think that one of the most interesting things about Wander is that we don't actually have any local property managers. People think that, oh, we must have a bunch of like on-site property managers that are employed by Wander taking care of these homes. And it's actually all done with software. Obviously, there are vendors who are onboarded onto the software who are completing these tasks. But everything that you can think of from intelligent pricing, vendor communication, coordination, logistics, guest vetting, guest communication is all done through WanderOS. And then there's really three or four core ideas from an agent perspective, whether it's, you know, communicating with the guest or automatically creating tickets and assigning them to the different vendors or actually communicating with the vendors through WanderOS, you know, directly to their phone.

35:19And so I'd say that, like, up top, you see this, like, really beautiful guest experience, this great booking platform. You stay. Everything's perfect. But underneath is this massive amount of software and automation and this thesis that property management was really just a software problem. Obviously, you just have a lot of logistics and coordination, and we felt that that can largely be automated. I'd say today we probably have about a 60 % deflection rate where the items and the tickets and the coordination and communication is being handled by these agents. but I see a path to what I would define as full deflection, meaning like 95 % of these tasks being done by AI probably in the next like 12 to 18 months.

36:03So do you guys take Brex? The credit card? Yeah. Yes. Wander accepts Brex, absolutely. So you can potentially book a corporate stay there? Yes, with Brex, who I believe is the sponsor of this show. Thank you, rex for sponsoring this show and um so i guess going back to your background how did we get here like you founded coder how did you start coder you have a really interesting founder background yeah i i became fascinated with computers and software at a pretty young age um and so i started my first company when i was pretty young 13 14 my first venture back to company i started when i was about 17, 18.

36:47That was coder.com. You know, it was interesting, like my college years were not spent in college, or, you know, partying or anything else. It was spent like building enterprise software and learning all the hard things about building a company. And I feel very fortunate in that my peer group was the most intelligent, fascinating, kind people that you could ever pray to be associated with at, you know, 18, 19, 20, 21. I still feel that way today. Like I feel so lucky to have so many smart people around me and, you know, helping to create who I am. But it was a, it was a really incredible experience.

37:32And it's wild to say that, you know, now at 27, I've been a venture-backed CEO for a decade is a pretty, pretty crazy statement. And you got involved in Teal Fellows? I did. I was a, I was part of the 2019 class of Teal Fellows. It's one of the most like remarkable things. You know, as a, as a young founder, it can be a little bit lonely. Especially as, as the CEO, you are responsible, at least this is how I felt about it. You know, I'm responsible for the mortgage and livelihood of, you know, a hundred plus individuals who are all relying on me. And am I making the right decisions or the wrong ones?

38:20And you just feel alone. And I don't want to use the word like scared because that makes it seem a little bit like too emotional. But I think it's something that, you know, unless you're a total psychopath, which I mean, to those who don't feel anything like, you know, god bless um but for me personally like i i feel it like i feel the weight of it um and so the teal fellowship was really special to me because it was the first time that i was able to meet people my age who are in a similar position and that just allowed for i mean candidly speaking like the first like true friends that I that I had um because there was like some level of level of understanding and I think that that word like fellowship was was very very real so yeah something I'm grateful for I'm not sure many founders are that open and honest about it but there is a tremendous weight and emotional experience to it especially if you're locked in and you're building something and you're not going the traditional path that everyone is swimming and you're constantly fighting that tension and you're doing it younger than people would have expected.

39:33Maybe you get treated differently, that kind of thing. But do you have any advice for young founders that might be going down this path? You know, what I would say is that I think that nowadays there is a culture of

39:52of celebrating, you know, young founders, young entrepreneurs. And so I wouldn't say that you actually have that much going against you. In fact, I would almost say a little bit of the opposite, that like if you are someone who's, you know, further along in their life, that there like may actually be some discrimination, which is, you know, terrible. And something that I think like Silicon Valley should actually like very much fix. You know, I'd say that, so I'll actually give the advice more so to like any new founder and entrepreneur as opposed to just someone who's young, you know, which would be that like it is very hard.

40:34It's going to be difficult and very, very painful. um and the you know ultimately like not to become like numb to that idea um like but to understand that like the feeling that feeling is like just you being like a good human um and then obviously like you need to continue to work through it like you can't let it paralyze you but don't like don't forget it, I guess. How do you keep your mind clear while you're scaling so rapidly and so many opportunities pop up and you just have to be dedicated to the mission? You know, it's funny. I'd say that I actually don't make like a great dinner guest, especially in periods like this, where like we're scaling so quickly, we're going through our series B, you know, I'm dealing with you know, all of the chaos that comes with that.

41:27And so like, if you're talking to me at dinner, I'll just start staring off like into the distance and one of my buddies we were at sushi in New York we just I just signed the term sheet and you know that was like to celebrate um and he's like you know John Andrew like you just didn't talk for like the last five minutes which I think is also like that I was sleep deprived but you know I would say that like Wander was actually built for that idea. Like I started Wander after stepping down from Coder and I started it because I wanted to get away and the experience that I had like wasn't good. And so, you know, I think that getting out into nature, going on a walk, you know, spending time with loved ones and candidly speaking, like going and staying at a Wander where you can be in this beautiful new place and have an experience where like everything's taken care of for you and you can think and process and transition.

42:26It's actually, we have quite a few customer stories where people send us very special, meaningful notes that talk about how they were making some really hard life decision and they ended up having the moment of clarity, you know, at one of our homes. And so I do think that that is really, really special. But I would say that, you know, one really difficult thing is that when you are in a mental space where you've had 10 hours of sleep and you're super stressed and like everything is going wrong and the world's all against you, it's hard to even know how to fix it, what decisions to make to feel better.

43:07And you almost have to be really prescriptive with yourself and say like, as silly as it sounds, like, okay, my head hurts. I should try drinking water. And I'm feeling really stressed. Even though I don't feel like going on a walk, I should go on a walk. And so you have to find those things for you and almost prescribe yourself as if it's medication. I'd say that that's been a really useful mental framework for me. Given your experience and how much you've scaled the company how big is the team who makes up it how how has this evolved so today we're about 100 people but a little bit more the team looks rather normal today where you have different department leaders sales marketing product operations and we have really phenomenal leadership i think that that That's something that I feel very lucky for.

44:10It is a relatively flat organization today. We do try and limit the number of sort of middle management that exists. And if there is middle management, it has to be leaders who actually are the best at said task. I don't believe in the idea of having someone run, let's say, a product team who doesn't actually know anything about product. You know, I think that as Wander goes through this next phase, you know, I had dinner with Nigel Morris, the founding partner at QED, and we were actually talking about how should I be thinking about organizational structure as we go from Series B to Series C.

44:55and he talked about this beautiful idea which is you know very obvious to I think a lot of people who had gone to business school or whatever else which is this idea that as you scale as a company at some point you switch from functional teams to business units where you have some specific tasks some specific KPI some specific item that needs to be done where you have a team that is obviously, you know, multifunction, you have your business leader, you have your salesperson, you have your product person, and it exists in this sort of separate function, as opposed to being like, okay, we have people from marketing and sales and whatever collaborating together.

45:34And so I think that that's, you know, something that I'm really excited for, for Wander to, you know, go into that next phase of being like a larger, larger company and switch from, you know, at first, everyone reports to you to the second layer, which is you have a really great executive team to I think this third idea, which is that you have business units that sort of like operate on their own, basically companies inside of companies. Wow. Yeah. So what do you exactly look for in hiring? Is there like a magic secret sauce? Is there an element? Are you looking for the dog in them? My answer is actually like ironically the opposite of that.

46:14So I think that beautiful companies have a have a soul um and the reason for that is that companies are just groups of people and people obviously like have a soul and so the soul that you want your company to have has to be the type of soul that you you know i ideally have in the types of people that you hire and so you know when building wander i was very very focused on alignment of ethics and virtues, along with, of course, the quote unquote dog in them or their skill set or whatever else. I wanted these to be like really good people, because I think that if you can have an environment where folks aren't fighting with one another, where there isn't drama or, you know, a lot of the things that can exist in some, you know, sort of more toxic cultures, that it would actually be a more productive outcome, even if, and this is a pretty contrarian statement, I think, you know, if I have two individuals who are making a decision and one of them is 10 out of 10 in the skill set that I need, but they are like just not a culture fit, meaning that they're like just a bad, aggressive, you know, sort of like person, then I will take someone who is a nine because I know that at least I'm going to be able to collaborate with the nine.

47:37At least I know that the nine is going to be able to collaborate with others. And as long as they have that work ethic and the drive to get to a 10, I think that, um, you know, at the end of the day, like those will be better hires and make you excited to show up to, to work. Um, and so I think that that's actually something I'd really recommend is to define the culture and the ethics and the type of people that you want um and be like very um you know sort of strict in in that are your business strategies with this first off before we get to that are you hiring yeah absolutely what are you hiring for everything yeah there's there's lots of open roles all right we'll link we'll link the careers page just i think it's on wander.com forward slash about perfect yeah apply now the fourth wall breaking is so funny to me have to do her part yeah i like it um so yeah i just so back back to your point about everything is moving really fast you saw your recent announcement on x itself yeah you know and and uh the new promo video and your cmo kyle tweeted this out and I thought this was so interesting because it will we'll get to this but I want to know more about like how strategies are shifting as you go to this next stage you mentioned talents going to the next stage thinking about hiring now that you're getting into the series b range so Kyle tweeted out that uh with the promo video the team used no creative agency it was all done internally there was no production crew it was just a single director filmed and edited and it was low cost you spent 35 less than original 2021 launch so like what kind of incentives are you giving the team or navigation to to be more efficient or is this all internally driven first of all i think that frugality is a critically important idea and mindset when building a startup particularly seed series a series b you have the classic story of amazon on building desks out of doors.

49:54And I'm sure that they don't do that today, but it is that like cultural idea. I think that one thing that we do is we're a very budget focused company where each department has their budget. And then inside of that, they can generally allocate the way that they would like, knowing that if you spend too much on a launch video, then that's a hire that you're no longer able to make. and I think that that's very different than most startups I think most startups say like okay how much do we want to spend on this launch video and whatever else there's no real incentive for them to spend less than the allocated budget it becomes almost like this idea of like we're going to spend right up to the budget and so you know at Wander I constantly encourage the team to think about efficiencies you know doing things ourselves doing things with like scrappy individuals in the same way that you would in your own life like in your own life you wouldn't spend you know uh money the way that i think that a lot of companies do and so you know the net result of that is is that when you when you look at wander and you think about all the things that we've accomplished and the rest you know it is only only possible with that idea if we had if we had a different culture i mean the company would have run out of money long ago what other demand generation taxics are you using?

51:15Yeah. So about 35 % of our bookings come from higher cost channels. So think like Google and Facebook, the rest are all lower cost. So SEO, influencer marketing, word of mouth, our repeat podcasts, podcasts, powered by Brex, this one, this podcast. Oh, God. And so, you know, I think that like our repeat booking rate is very high. That obviously drives a lot. You know, Wander has a pretty incredible LTV to CAC. Our over a three-year period, so our like 2022 cohort, 2023 cohort, it has over a$10 ,000 LTV, which means that basically folks are booking once a year. Yeah. Which is phenomenally high.

52:06you can imagine what that LTV looks like over a 30, 40, 50 year period, which is also why as a company, I take customer satisfaction so, so seriously is that these customers aren't worth just one trip. They could be worth, you know, 20, 30, 40 trips over their lifetime. And they're also going to tell 20, 30, 40 of their friends. And so it's really critical that you nail that. But from a marketing perspective, I think that as you go from seed to series A, series A to series B, that you have multiple profitable channels because otherwise you are going to fail to scale. You're going to find out that that one profitable channel that you had can only reach a certain number of people and that that certain number of people obviously isn't enough to get you to that next phase.

52:53And so I think that de-risking that from a marketing initiative perspective during your Series A is really important to show growth investors that we have five, They have 10 different channels at a very low CAC that we can put money into and that will actually improve as we grow. How do you then match the demand with the rapid increase in supply? You mentioned you're going to be onboarding like 200 to 300 new properties. How do you scale that? So going back to the dinner that I had with Nigel recently, Nigel Morris, for those entrepreneurs who aren't familiar with him, he is one of the clearest thinking, most interesting, passionate investors that I've ever met, Midas List investor.

53:39And we talked about this idea that Wander has about 400 ,000 users on our platform. and so it was less a question of how do you grow your user base and more of a question of how do you activate them and i think that that subtle difference in framing is could be really valuable to a lot of different startup founders out there which is this idea that you already have all of the customers that you need they're in your wait list they're signed up to your product They're following you on Twitter, whatever it is. And you don't have a growth problem. You actually have an activation problem. And so the question is, how do you activate?

54:20How do you encourage? How do you light a flame under those users to go and make the leap with you, to go and try your product for the first time? And if you have a really high MPS product, you should be off to the races. I think the same could be true of a podcast audience. You think about, I don't actually need to grow my subscriber count. It's more a question of how do I activate that community? How do I activate them? And so that's currently actually my focus is less so about growing the number of users on platform, but activating a larger percentage of them. And there are, of course, various different ways to do that.

54:54But I think that that framing is probably a useful idea for a lot of listeners. How does the business model work? So it's primarily a marketplace. You're taking a percentage off of each booking. That's correct. Maybe a percentage off of each vendor from chefs to maybe your private jet. Could you explain more on that? Yeah. So Wander works as a take rate on gross revenue. So when someone makes a booking, we take a fee of that booking and then we also charge a fee to the owner on the underlying revenue. We don't actually mark up any services. We don't charge any type of payment processing. fee when it comes to vendor payouts or coordination or anything like that.

55:40We like to align ourselves as much as possible with the homeowners and with the guests, which is that we're creating value and providing you this place to stay. And it's going to be a really great experience. And to the owner, we're going to bring you this customer that you wouldn't have had. And so I think that sharing in that is a really good way of ensuring that your MPS ironically stays high is that if you align your monetization with what's important to the customer and what's important to the owner, what's important to both sides of the marketplace, then that is ironically the only way that you're going to be able to deliver a high MPS.

56:17The moment that you start to have conflicting monetization incentives, you could run a pretty serious risk. And since this used to operate as a REIT, do you still own any properties? I know you're moving to asset light as well what's the shift there yeah so wonder all of our scales asset light um you when you think about the quantum of capital the 300 you know 200 300 homes that we'll add this month is about 1.5 billion dollars of real estate um and so having any percentage of that even one percent um wouldn't wouldn't be possible unless we were partnered with with a large uh capital provider.

56:57And so, you know, from that perspective, most of our original homes have all been, you know, sold to third parties. They've all stayed on the platform. You know, they were investors or whoever else who wanted to own them. We still do own one or two from a more of like a strategic perspective, like being able to have that control and understanding is actually pretty useful. And of course, like you can sell the asset in the event that you need to from a capital perspective. um but everything you know to to your your question is asset light at this point we've covered so much i have like two more topics to get through i hope you're okay with that absolutely i'm excited we'll just keep going um you've raised a tremendous amount of money to date could you share how much you've raised i know the debt facility was part of it um you can take that in take it out however you want to do it but who have you raised from um and what was the total yeah so i i don't i don't like to include debt in like the total figure um and to be clear like that facility you know happened and then it didn't happen um and so it's not like you know wander as a company it's like 100 million dollars in debt or something um you know we we raised i think i mean gosh with this round i mean it'll probably end up being over$100 million.

58:20We're backed by some really, really remarkable investors, QED, Redpoint, Briar Capital. I mean, there's a long list of folks. Paki is an investor in us. You know, I think that like raising capital tends to be something that is really celebrated, you know, in the startup community. But I think, and as it should be, like it's, you know, it is at the end of the day a representation most of the time hopefully of building a good company but i i think that like um it would be cool if we liked the headline of like wander you know achieved like a 85 mps this month and like that was like the big news um but yeah we've we've we've raised we're very fortunate especially after this round to be super well capitalized and so it feels really good as a founder to know that what i'm building is going to be around a little bit longer and hopefully build a actually build an enduring company i was talking with someone about that idea of like google is only 20 25 years old um you know apple the same you even tesla and so it's like i think people don't even know like what it actually truly means to build an enduring company like something that's around for 100 years like coca-cola or whatever else and And so I think that that's something that I'm really excited for is to spend the rest of my life building this company.

59:46If I'm so fortunate, obviously, I don't know how the world will turn out, but that's something I'm excited for. What do you look for in investors? I know you mentioned QED a bunch of times. Yeah. I think that the first thing is that they share your ethics and that there is a certain level of protection and trust. You know, when you bring on a board member, you're effectively giving someone a vote in how your company is ran, the allocation of capital. And it has a real effect. Like board meetings decide whether or not like a certain feature gets removed or if the company cares about net promoter score or whatever else.

1:00:34And so if you bring on the wrong investors, you can totally destroy your company. Yeah. Yeah. And so, you know, what I focus on is this idea of trust. Like my hope is, is that like, I'm going to do my best each and every day. I'm going to ensure that, you know, the employees are taking care of, our customers are taking care of, that I'm a good fiduciary. And my ask is, is that, you know, as an investor that you are a good actor, that you also, you know, fulfill your fiduciary duty as a board member to the company, as opposed to, you know, sort of prioritizing your own gain. And that is a really difficult balance.

1:01:12You obviously have the stories of VCs, you know, firing their founders and, you know, acting badly and giving predatory terms and bridges and all these different things. And so, you know, at the end of the day, I'd say as a founder, like, make sure that they match your ethics, make sure that they, you know, have a certain level of their own control. That also is something that can happen a lot is that you can bring on a firm and a partner where that partner may be great, but that firm may direct them in a different way. And also vice versa, you can partner with a name brand firm that has a great reputation and partner act in a bad way.

1:01:51And so I think that it's, I mean, candidly speaking, it's risky. If you are bringing on external capital, you now have shareholders, you have a boss and that boss can fire you they can change the direction um and so like you you should you should do your best to ensure that they're aligned with with what you're trying to accomplish yeah it's very sound wise advice and you've been doing this for a while 10 years plus yeah it feels like i've lived many lives at this point i have heard that you do run by some really strong life philosophies could you share more on that when when i was when i was younger um i i became self-aware like a pretty young age like um i remember being like eight and laying on the grass and doing my homework and like stopping for a second and saying like life is never gonna get better than this moment like you are eight years old buddy and soon you're gonna to be 30 and 40 and 50.

1:02:54And like, this is what's up, like, enjoy, enjoy it. And so when I was young, I made this, this set of rules, um, to help me live, live a good life and to help, to help me decide, uh, in what I thought were challenging circumstances and ideas. Um, and so the, the, the four, the four rules are, and the first one is rather morbid for a kid to come up with, um, is that the worst thing that happens is you die. And for me, what that rule or that mentality enables me to do is it enables me to walk into situations with a level of almost comfort that, like, hey, like, you can do this, you got this, like, you know, the worst thing that happens is you die, right?

1:03:41So it's like, which, of course, like accepting death is a really like, you know, crazy idea. Um, you know, the, the second one was about urgency. Tomorrow is a lazy man's today. Uh, which was if you want to live a fulfilling life, like you can't just delay things. Like you should try and get it done now. You should, you should take that shot. You should take that chance. You should, you should, you should really go and, um, try and accomplish it. Uh, the third, uh, was live with it or fix it, which was because I felt like, and had seen a lot of people end up in circumstances where they were almost stuck.

1:04:19Like, this thing really bugs me and I don't know what to do and whatever else. And for me, the framework was you have two choices. You can either live with it, which is totally fine, or you can fix it. And once you decide which one of those you're going to do, then like, great, you're now out of this sort of purgatory of indecisiveness. um and the fourth um was that as i was was getting older as i was you know becoming like a teenager mid-teens i found that i started to say no a lot to um different things that were happening in favor of work uh like i would be working really hard and you know some people would invite me to go, you know, do something.

1:05:04And I would say, I would say no. And, um, I came up with the rule of always saying yes to adventure, which is rule number four, which is this idea that if you want to have a life that also balances, of course, your ambition, that going out and experiencing the world and having adventures and, um, you know, that, that dynamic is really, really important to living a happy and fulfilling life. So those were my four rules that I sort of came up with when I was younger and they've served me well. And yeah, I'm very grateful to have had them along the way. Yeah. John Andrew, those are beautiful. that is like a beautiful way to wrap up the conversation too um i like to end on a positive note that's a pretty positive note but to extend that because you're just so good i'm gonna keep you here all day what are you most looking forward to this year gosh that is a fascinating question because you have two you have two sides right you have the personal side and the company could be both well it's funny like one of the things that i'd like to say i can't because it would spoil the surprise for her um i think even saying that probably does she probably won't even listen to this who listens to their boyfriend's podcast right um no i think it's it's fine um it could be it could be a trip it's probably a trip who knows we're gonna cut that or leave it in okay we'll leave it in um you know from a from a company perspective i think that wander has reached the point where we have a lot of the ingredients for success you know we're through this round will will be well funded we have a great brand we have a great team we have customer love.

1:07:05And it's about taking all these ingredients and bringing them together, sort of having the company enter into that next stage. And so I think that I have a very good path and idea on how to get us there. And ultimately, we'll certainly try our best. But Wander has now hit the point where if it doesn't work if you don't see you know hundreds of thousands of locations and a big global company and hopefully a lot of happy customers um that it won't be because the idea shouldn't have existed it will be because like i failed to to make it happen and i am very dedicated to not failing like i think that the world will be a little happier with wander in it And I think that that's a good thing.

1:07:58Find your happy place. Yeah, exactly. Well, John Andrew, it was a pleasure to have you on. Thank you so much. Thank you. Thank you for having me. Hey, it's Molly. If you enjoy our interviews, check out our newsletter, sorcery.vc, where we deliver a once a week top deals and tech headlines email and also go deeper on our podcast interviews. Subscribe to Sorcery today. And don't forget to subscribe to the podcast on YouTube, Spotify, Apple, or wherever you listen. Link in description to sign up.