Podcast: Wander CEO John Andrew Entwistle discusses young entrepreneurship and revolutionizing the vacation rental experience

In this episode of Fintech Thought Leaders, QED's Head of Early Stage Investments Bill Cilluffo speaks with John Andrew Entwistle, CEO of Wander.

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Show notes

Bios

Bill Cilluffo joined QED as a Special Advisor in the fall of 2014 and became a Partner in 2015. He is currently Head of Early Stage Investments after six years as Head of International, leading QED’s Investment teams in Latin America, Europe and Asia.

Prior to joining QED, Bill spent nearly 20 years at Capital One, spanning several roles and leading several businesses. He spent the first 6 years of his career leading Marketing, product development and credit policy for Capital One’s subprime credit card business; ultimately having overall P&L responsibility, and growing the business to become the most significant player in the market. He moved on to spend 2 years in various new business development roles, spanning the telecom, medical finance and small business finance industries. Bill spent 3 years as Deputy Chief Credit Officer for the bank, playing nearly every role there was to play in the central credit function, after helping build the department from scratch in 2002.

Bill then pivoted his career to general management, leading Capital One’s Canadian, and ultimately International businesses, over the course of 6 years. Profitability of the business grew significantly under Bill’s leadership, through new product and channel introductions, acquisitions, and significant cost take out. During Bill’s last 3 years at Capital One, he led its Co-Brand and Private Label credit card business, building the business nearly from scratch to one of the top few players in the US market, through a series of acquisitions, most notably including leading the acquisition and post-merger integration of HSBC’s US credit card business, which closed in May 2012.

Bill graduated with a BA in economics from the University of Michigan, and competed the SEP program at Stanford GSB.

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Bill Cilluffo:

You're listening to the FinTech Thought Leaders podcast from QED Investors, your deep dive into the world of venture capital and financial services with today's digital disruptors. QED is a global venture capital firm focused on investing in FinTech companies all the way from pre-seed to IPO. FinTech Thought Leaders brings together the most talented entrepreneurs tackling today's biggest problems. If you're looking to learn more about what motivates our founders and team members to succeed, you're in the right place.

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Hello and welcome to the FinTech Thought Leaders podcast. I'm Bill Cilluffo, head of Early Stage Investments at QED Investors. Today on the podcast, I'm excited to be joined by John Andrew Entwistle, founder and CEO of Wander. John Andrew, welcome to the podcast.

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John Andrew:

Thank you so much for having me. Stoked to be here and talking with you obviously.

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Bill Cilluffo:

Nice. Well, I'm looking at John Andrew at his apartment in Sausalito, and looking out his back window at one of the most beautiful views I've ever seen. So if I look like I'm ogling you, it's your view that I'm incredibly jealous of.

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John Andrew:

Listen, I'll take it. Did my hair this morning, so I'll take the compliment.

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Bill Cilluffo:

Nice, nice. Well, look, we're going to get into Wander a little bit later in the podcast, which is the company that you're currently CEO of. But just to orient the audience, I wonder if you can give us about a 60 second elevator pitch on what Wander is and what you guys do.

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John Andrew:

So I think a lot of people have rented a vacation rental, right? Say Airbnb or Vrbo, and had a bad experience, whether it be the place didn't look like the photos or the beds were uncomfortable or the internet was bad. And so the whole idea with Wander is to verticalize the vacation rental industry to really own the distribution and the operations and effectively have all of the homes be consistent, the same beds, linens, views, amenities, those different pieces. And obviously there's a lot of verticalization behind that infrastructure from ownership to operations and beyond. But the real idea is for the customer to have this really incredible consistent experience where you can go to wander.com, book any of the properties, and know that you're going to have an incredible time.

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Bill Cilluffo:

No, that's awesome. I've certainly heard from many, many people how amazing that experience is and I keep looking to book my trip, but I spend so much time overseas. I haven't been able to get to one of them domestically yet, but I'm looking forward to checking it out.

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John Andrew:

We'll fix the overseas problem soon. You can be in charge of launching our international markets.

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Bill Cilluffo:

That's perfect. But look, as a start, I'd love to get into your entrepreneurial journey. Wander's not your first rodeo. It's either your third or fourth, if I'm not mistaken. And I believe you actually started your first company at age 13. So I'd love to go all the way back and hear about what that company was, but more importantly, what is it that really drew you to entrepreneurship at such a young age?

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John Andrew:

Yeah, it's actually a pretty deep question. I was raised by a single dad, lawyer. When I was pretty young, I walked downstairs and I saw him working at his computer. It was like five in the morning, I had woken up in the middle of the night, and all of a sudden it really clicked for me the sacrifices that he was making and watching him work to support me and my sister and then somehow take us to school and then go to work during the day and then do it all over again at night. And so I think a lot of it was I wanted to work like dad candidly. Then I was like, okay, well I need a computer. And so built my own, which he was supportive of. Then from there you have this young kid who has access to the internet and all the things around it and I just became incredibly passionate about software and design and product. And in terms of that first company, I think a lot of young entrepreneurs, it started with video games.

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So the first thing I did was download a few different video games and so excited to explore and have fun and all that fun stuff, but very quickly I wanted to play with other people. And of course back then you had to go and set up servers for everyone to go and join, and then you get exposed to the early cloud and hardware and then before you know it, had a little company that was really all designed around hosting and allowing people to play together and those different aspects. So that first company was really around hosting game servers and allowing people to play together and obviously built a lot of infrastructure around that as well and kind of exposes you in the early days to a lot of really cool dynamics of the internet. But yeah, that first company did fairly well. We were doing low six figures in revenue, so always joke I was not focused on my homework at all.

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Bill Cilluffo:

That was probably the right call judging by that number. So look, you had a little nonchalant statement in there that you kind of passed over, but I've got to go back to. So age 13, hey, I wanted a computer so I just decided to build one. Probably not something that most 13 year olds are thinking about. How did you have the confidence or decide to jump into that? Is it something you had been doing as a hobby before or was this just completely out of the blue?

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John Andrew:

Candidly, building a computer is not that difficult. So to any parents who are listening, if your kid wants a new computer, definitely try and get the parts together for them to build it themselves. I think definitely with adult help, it's pretty easy.

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Bill Cilluffo:

Probably not with my, you know, Bill Cilluffo's adult help, but...

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John Andrew:

Yeah, I shouldn't say easy. I don't want to offend anyone. No, it's really doable. Anyone can do it. For me, I wasn't allowed to play video games growing up, wasn't allowed to watch cartoons or those different things, not in a super strict household sense, more of the sense of, hey, we live in a beautiful world, go out and explore it. That kind of vibe. And so I had grown up tinkering with RC cars. That's how I got my exposure to electronics, was building RC cars and the motors and all that fun stuff. And so it was like when I wanted to access the internet, I already had the core understanding of components and how to put something together and I think more so just an ethos of if you don't know it, look it up, follow the manuals, read, ask people. There's a lot of great information out there to discover. And so I think that's what let me do it at a young age. And of course also an incredibly supportive Pop. It's like before I had any money, someone bought those initial computer components, which he gets massive credit for.

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Bill Cilluffo:

You had this video game business, sounds like that was doing pretty well. But flashing forward a few years, you actually started your first really substantial company that was less out of a hobby called Coder. I wonder if you can just talk a little bit about that journey of how you came upon that and a little bit of the Coder story.

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John Andrew:

So I had enrolled in high school online really to spend time with my Pop. He would travel all around the world trying cases and beyond, and I figured why not, which also gave me a lot of free time because I was able to do a year's worth of schoolwork in 30 days. It was really useful. And so during that time, me and my co-founders, we started Coder, which essentially moves the development environment where software engineer writes code to an organization's cloud infrastructure, really with the vision of bringing the productivity of a startup to the enterprise, basically enterprise security and speed and all that sort of fun stuff. And so I started that company when I was 17, 18, so still in high school, and we wanted to get an office. So we moved down to Austin, I was in New York, Kyle was in Saskatchewan, Canada, which is very far away, and Ammar was in Alabama and moved down to Austin to start that company.

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The product was incredibly technical, very difficult to build, took a lot of time in engineering power, but when we launched we saw incredible reception and we also at that point had a small team and we're certainly also running out of money. So I'll never forget being 18, 19, cold emailing VCs, didn't even have a LinkedIn at the time saying, "Hey, I have this company and this product and it's starting to grow and it has a ton of potential. Can I please pitch you?" I think a lot of early entrepreneurs wonder, how do I get in contact with VCs? How do I raise money? Those different pieces, and it's certainly easier if you can get warm intros or otherwise, but one thing that happened as that company started to grow was that people just started to take notice because your cold emails now had metrics and progress.

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I didn't have a resume but my company and how awesome it was was starting to be that resume. We went on to raise our seed that was led by Redpoint and Uncork along with Founders Fund joining and a few others. And then shortly after we raised our series A and then eventually our series B and now Code Server is one of the most popular open source projects in the world and our enterprise product powers dozens of Fortune 500 companies. So if you've ever streamed a TV show, a lot of them write their software on Coder. If you've ever sent a wire transfer, a lot of the banks build their software on Coder. So yeah, ran that company as CEO from 18 to 23 and was an incredible experience.

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Bill Cilluffo:

That's amazing. So your first business really stemmed out of a hobby. You played video games, you wanted to play people and take a few steps forward and it becomes a business. This one seems extremely different. Many business ideas come out of personal experience. I don't know if you had personal experience from your first startup. How did you even come up with the idea of doing this?

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John Andrew:

So the original idea for Coder was actually basically a consumer IDE. It was like we wanted to write code in the cloud. That was the whole idea. In the same way that you use Google Docs to edit, whatever, an essay or whatever else, we wanted it to be so that you could open your browser and code in the browser, which is now there are lots of products that do that, but back then there wasn't anything. As we launched that product, what we saw was we turned on monetization, we had like 60,000 users. We had just raised our seed and no one wanted to pay. I think we made $20 and I immediately told the team and alongside my co-founders and said, "Guys, this isn't going to work. We have 60,000 users. This is the best way to monetize. No one's willing to pay for it. The product has issues but it's relatively stable. We're going to have to pivot."

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Which after building a product for two years and having a team and just raising a seed and you feel like you're on top of the world, people think you're a little crazy and it certainly feels that way to you as the founder, but that's what we decided to do. And with it we created our open source project Code Server. We released that alongside effectively an enterprise page that said, if you're a company and you like this technology, sign up and give us a call. And Code server, when we released that, basically the engineering community was ecstatic. It became the fastest growing project ever, and with it thousands of companies, and I was on the phone with all these massive Fortune 500 companies pretending that Coder was bigger than it was and trying to understand exactly what they wanted, and eventually we built that product for them and obviously landed some pretty massive initial contracts.

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To answer your question in terms of how did you come up with the idea, it started almost with a technical vision of the future and an inevitability. We thought that software development was eventually going to move to the cloud, but the end business model radically shifted as the market sort of told us what to do.

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Bill Cilluffo:

No, that makes sense. I mean, it's an interesting flavor on a freemium model. Come up with this open source product to get all the engineers hooked, and then when the engineers have jobs and the companies need it, then you can monetize that way. It's a pretty cool little hack there.

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John Andrew:

Yeah, the business model is called open-core, which obviously we did not know at the time, but it's pretty popular. There's a lot of big open source projects like HashiCorp and various databases, et cetera that follow that model.

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Bill Cilluffo:

Such a successful company. You talked about all the different people on it. What made you make the call to leave Coder, decided to not be CEO? And then we'll talk about what comes next with Wander here shortly, but what caused you to take that leap?

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John Andrew:

I had been running the company for the last five plus years and had a pair of two other incredible co-founders and ultimately at different stages in the company, you have to look at what the company needs and who's potentially best to do it. And we made the decision together that it was going to make most sense for my co-founder, Ammar, to step into the role and for me to explore and see what was next. And it's always a difficult moment when you step away from something you've built for so long. If I think about it, I think building that company was like 40% of my life. Let's say that you become conscious at 16, so then it would be the vast majority.

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Bill Cilluffo:

You started a company at 13, so we'll rewind the clock further for you.

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John Andrew:

It's always difficult, but at the end of the day, you do what you think is the best job possible and it's always a transition. I think anyone who's gone through it will probably understand why I'm having difficulty putting words around it, but it was a really lovely thing. I stayed on the board for about a year afterwards and Wander started very quickly after, and so I had my hands full. But yeah, Coder was an incredible experience.

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Bill Cilluffo:

Is there a way to point to the single hardest part about it or is that too challenging?

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John Andrew:

I'll never forget my last all hands. I knew that I wasn't even going to be able to think through it live, so I ended up just being like, okay, I'm going to memorize exactly what I'm going to say, because you see all these faces and people who you deeply love. I think that's one thing for me as a founder that I don't think people truly understand is that I feel such a sense of protection and love for the team, for our shareholders, for the company and the product for our customers. And so it's just difficult. So I memorized that one and blacked out and went through the spiel, but yeah, that was probably the most difficult piece. And then of course after when your phone stops buzzing and emails stop flying in and there's just silence, it is a pretty trippy experience, then you're like, I'm starting from scratch.

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Bill Cilluffo:

You mentioned that you first started playing around with electronics through RC cars. I know that electronics wasn't the only thing to stem from that. The car piece became a pretty important part of your life. I'd love to share with the listeners your auto journey and kind of what that's all about.

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John Andrew:

It's definitely, I think, something that's less covered. I have a passion for vehicles and motors and going fast. And when I was a kid, I think around 15 or so, my Pop took me to this racing school out in Arizona to get my first taste of not just driving a car but also how to do it responsibly and on a track and in a setting like that. I absolutely fell in love with racing cars and that whole world. And at the end of their lessons, they had a car called the Formula Mazda, which is a Formula car, but powered by a Mazda engine, and that's when I fell in love with Formula racing. Very quickly ended up joining a team out of Dallas, and so raced Formula cars, Formula Mazdas all across the country in amateur races and ended up finishing second in Nationals in my second year doing that.

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And then moved up to Formula 4, so the entry into the Formula 1 series, and ended up joining this incredible father-son team and raced with them and I raced with them up until I ended up breaking my back racing at the Indianapolis Motor Speedway. And at that point, of course, also Coder was happening. I was still building Coder, so I was like 17, about to turn 18 or maybe I'd just turned 18. And after I broke my back, two weeks later, I was with my back brace, setting up the desk setups, surviving on whatever the rest of the prescribed painkillers were that the hospital gave me, setting up the office for the team. And so that was sort of my racing journey. I still raced cars after the back healed up, would race trophy trucks down in Baja, and that kind of cool stuff. Certainly got much more dialed back, and I never viewed it as my future like I was going to become the next Max Verstappen or something, which I appreciated.

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I'm glad I had that foresight at a young age, but certainly made the most of it, which was pretty cool. And obviously you get to learn a lot of other things about life beyond just business. You learn about competitiveness and team dynamics and a whole different world, and of course characters, how do you deal with this 50-year-old man who's pissed that you beat him? Those different things were really interesting. But yeah, I was extraordinarily grateful and it was a really wonderful childhood, and got to see a lot of the country, which was cool.

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Bill Cilluffo:

It's fascinating doing this series how many of our entrepreneurs have pretty cool background stories that you just don't really know about. Are you a huge Formula 1 fan today or is it kind of hard given that you know you were in it and ended with a probably not so pleasant experience?

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John Andrew:

I'm a fan of Formula 1. I think they've made the cars and the tracks quite a bit safer. But I do think though that how dangerous it is really isn't properly shown to the audience. And I think people forget that. I think nowadays a death is pretty rare, but you flash back even 20, 30 years and people were dying every season. And of course the other piece is these drivers are trained to not crash in a way that they're going to kill themselves, which I know sounds weird, but it's like they're going to try and hold onto that car as long as they can. And so I do wish that they showed that piece, just how dangerous it is so those young kids like me watching who think they're invincible are sort of reminded that they're not. But yeah, I certainly love Formula 1, the engineering behind it, the team dynamics, the logistics of taking this 500 person team all across the world. It's pretty incredible.

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Bill Cilluffo:

Yeah. Super cool, super cool. You had left Coder, you were kind of thinking about what to do next. You made it sound like Wander came pretty quickly, but that's a very, very different business than cloud coding infrastructure. What is the origin story around Wander?

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John Andrew:

So after I stepped down, I'd rented this cabin out in Colorado to sort of get away, think about the world, quarter life crisis. And when I got there, the place just didn't look like the photos. Beds were uncomfortable, internet was bad. And so I opened up my little notepad and put the idea for Wander next to all the other ideas that were not similar at all, and candidly had no intention of building the company. Had the idea and closed the notebook. And then the rest of that week, which is how long I wanted to give myself to transition, I was supposed to just relax, read a book, get my head straight. But the idea for Wander just ended up keeping me up at night. I couldn't help but think about it and want to work on it. And so after I left that cabin, I just started working and thinking about all the reasons why this company was going to die and why not to start it.

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At that point, I wasn't ignorant to this idea that whatever company I started next, I would spend eight plus years on at the minimum just to ... and all the torture that comes with building a company. And so you want to make sure that it's right. You want to make sure that it could work, and you also want to make sure it's something that you want to do. And so I spent about three months working on the idea, crafting it, thinking through the different models, what would happen if plan A failed, what's the fallback, what are all the adjacencies? Because at that point too, I also wasn't ignorant to the fact that your first idea inside of the space tends not to be the one that becomes the multi-billion dollar outcome. There's always that little adjustment that takes place. And so yeah, just reached the point where I loved every single second of working on it.

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I felt happy again and I couldn't help but start the company and was really fortunate that a lot of people had seen me work and seen who I was and wanted to do it all over again. And so we raised our pre-seed and seed that was led by Redpoint who led Coder seed in series A, and so got to work with Alex Bard over there all over again. And it's wild. He's been on my board since I was 18, so it's like the story continues.

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Bill Cilluffo:

It's always good when you do one startup and the firm wants to lead your next one. That's always a great sign. So look, you talked about almost knowing upfront that whatever you came up with the first time wasn't going to be the exact thing that you wound up doing. I'm assuming that when you started the company you did not assume interest rates were going to go from zero to 5% in the matter of a couple months and change the world of real estate so dramatically. I wonder if you can just talk through a little bit of from the original idea to where you are now, how was that impacted by the crazy landscape that you wound up building this into?

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John Andrew:

A lot of people who have a heavy real estate background, they sort of have the context of how wild the current transition and times are versus for me it's like, I'm just like, okay, this must just be normal. You have 300 year old banks collapsing and all this sort of crazy stuff. When we started Wander, one dynamic that exists with marketplaces is called the Cold Start Problem where you have to have supply to have demand and you have to have demand to have supply, and therefore you end up in this Cold Start Problem. And so the idea with Wander was could we kickstart that demand by effectively owning our first few assets, building on balance sheet, and what would that look like? And as we were exploring that model, obviously we were in a historically low interest rate environment and the capital markets were far more open than they are today obviously.

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And so that was an avenue that we were able to pursue and I think we were able to pursue it pretty far, not just beyond our first few assets, but call it our first 15, which candidly was I think although difficult to scale, really incredible for honing in the actual product, building out the underlying operations, those different pieces because we understood not just what it was like to be the platform and the distribution, but we also understood what it was like to be the actual property owner and the operator and all those different components that come with it. As interest rates began to rise, obviously it becomes less feasible, the cost of capital begins to rise, and at that point we had already had a brand, we had I think over 150,000 users and it was really time to ramp up scale, and so we began to explore adding third party properties into that mix.

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And candidly, I wasn't expecting the reception that we saw there. I think in November we're on track to add 10 new properties, which is pretty incredible for us given how old the company is. And so things transition and change, but as a founder you sort of have to look at what's happening. Is the ground shifting underneath your feet? What's working, what's not? And candidly have a little bit of courage and be unafraid to make those adjustments. I think everyone wants you to grab onto an idea and run it into the ground and it's like no, the purpose is to build a truly valuable and important company, and there are going to be adjustments and changes along the way. The pivot may not be as drastic as going from a video game into Slack or Instagram going from a hotel booking company or whatever it was into Instagram, but there are always going to be little pivots along the way.

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I actually think that every founder knows that who made it to the end. And so that's the one thing that I would say to any founders listening is that if what you're doing isn't working or things are changing, pivots and adjustments and evolutions are not a bad thing. I'm sure in your seat you've seen hundreds of them along the way and the good companies tend to do it very well and in a way where they don't skip a beat.

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Bill Cilluffo:

Yeah, I mean Nigel likes to joke that out of 200 investments Acuity's made, two ever have sort of hit their numbers the whole time straight through, and I'm pretty sure even those two have had lots of movements and changes along the way. So it's probably literally a hundred percent if you actually get underneath the covers.

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John Andrew:

Yeah, I'm sure if you asked those founders, there would be mid-quarter panics that took place.

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Bill Cilluffo:

Yeah. For sure, for sure. Your original idea that led to wander was, hey, I stayed at an Airbnb. This Airbnb kind of sucked relative to my expectations. So one of the early days of Wander is, hey, I'm going to own the inventory so I can control it and I can do whatever. Now you're going to a bit of a third party thing. Does that bring back the Airbnb problem? How do you deal with that? I mean, is it still kind of the core idea? I mean, that sounds like a pretty important change given the origin story of the firm.

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John Andrew:

The key dynamic was taking control over the underlying asset. This idea that when Wander would come in that we controlled everything end to end, from the furnishings to the beds, the operations of the property, the maintenance, all those different pieces to effectively the point where the only difference was where the underlying real estate capital came from. And so in that context, when we began to test it, guests didn't even know that these properties were owned by a third party, which makes sense obviously because if it's branded like a Wander and looks like a Wander and everything's the same, who owns the actual real estate on paper? It doesn't matter to the end customer. What was really cool though, and I think something that isn't realized is that Wander's strategy of building a brand and building our own distribution results in pretty dramatic outperformance relative to the broader market, very similar to sort of the big hotel chains, how they outperform some mom and pop hotel. And that dynamic we found people were willing to pay for within the short-term rental world.

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And so that's what I think has allowed us to scale and start scaling as quickly as we have is that we can very quickly show that Wander leads to a 30 plus percent beaten occupancy, 30% plus B in ADR, and obviously in terms of your gross revenue on a T12, that's pretty meaningful.

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Bill Cilluffo:

Yeah, that's awesome. How many properties do you have on your platform now?

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John Andrew:

It's changing pretty rapidly now. We'll finish November with over 40 and we're targeting 50 by the end of the year, which is exciting.

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Bill Cilluffo:

That's awesome. Because as a vacation brand, obviously the broader the depth is the more different people you'll attract. So there's probably a nice positive flywheel too as you get that number up.

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John Andrew:

Oh, the flywheel that's starting to kick off is something that I hoped for and probably was in the thesis that a lot of VCs had when we started the company, but seeing it start to really kick off now is pretty remarkable. We have guests who stay in New York who then go to Malibu, guests who stay in Calistoga, then go to Cave Creek, and all of a sudden as that network builds, you have this flywheel of people just exploring all these destinations. They have their accounts, so you're remarketing and distributing to them. It's really speeding up. I'm very grateful the pace that Wander's now operating at and the clarity of the potential we have. I recognized how rare it is and I'm super grateful to be building it.

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Bill Cilluffo:

Very cool. Well, very early on in this chat we talked about international and sort of your desire for international expansion. Wondering if you can talk about your views on that.

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John Andrew:

Wander as a travel company by definition has to become a global business if it's to reach its full potential. And when you look at the broader short-term rental market, you have Europe and Japan and Australia and just all these incredible places with existing inventory, with existing operations, and of course a user base that's already traveling to and experiencing it. And so the idea for Wander to become a global company, it's sort of ... I mean, that's why our logo is the globe was because I wanted to represent our global ambitions as early as possible, which I think when we had three properties was less obvious than today and hopefully, certainly in a year from now will be very obvious. As you're well aware, there are a lot of complications going internationally from legal, regulatory, even just expense management team, all those different pieces, but the network effects and flywheel that can happen when Wander is a known brand in Europe and Europeans are coming to America or in Asia or otherwise becomes pretty significant pretty quickly.

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And obviously there's quite a bit of travel and tourism in those markets as well. And when you look at the big hotel brands, they'll have locations internationally and so Wander will certainly follow suit. It's something I'm excited for. I also love the branding that's attached to it, like Wander Australia, Wander Japan, Wander Europe, it just kind of flows and feels really good. So yeah, something I'm excited for, but I also recognize that when you expand internationally, you have to do so from a position of incredible strength, otherwise you end up realizing that it's more expensive than it is and you don't have the resources to finish it. But fortunately I have a lot of smart people on the cap table who have experience internationally, so I look forward to using it and using your opinions on that.

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Bill Cilluffo:

Dynamite. I love it. I love it. It was funny, I was having dinner with one of our former portfolio CEOs who had an exit a couple of years ago, and he's actually living in Barcelona and he was telling me Barcelona passed New York as the most visited tourist destination in the world last year, which kind of hard for me to believe, it's so much smaller of a city, but good to see international travel up and running again. I know it took a big dive during the COVID year, so it's great to see. So look, if you look out a year or two years, five years into the future for Wander, you've already talked about one major change, which is, hey, I started as a, I'm going to balance sheet these properties and now I'm mostly focused on non-balance sheeted properties as a way to scale in a more capital efficient way. You've talked about international expansion. Are there other things on the horizon or do you think those two are enough and you'll be focused on those?

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John Andrew:

No, there are certainly other things. I mean, one of the things that I enjoy the most is thinking about the future and all the products and things that you can build. I realize that for a lot of founders you're constantly being told to focus and otherwise, but for me, thinking about the future brings me joy and thinking about new products and otherwise, so I always make sure to allocate a little bit of time to it. One of the really cool things that we just launched is the ability to talk directly with our concierge inside of Wander systems. So through the website, through the app, those different pieces, and we've already begun to add these large language models so the concierge can then say generate responses and all that sort of cool stuff. The next iteration which we're launching in Q1, and it's funny, I'll say Q1 or Q2, so the team doesn't kill me for setting expectations, is integrating the ability for this AI concierge to book things like your flights, your rental cars, different locations, packing lists, all those different pieces directly through the Wander app.

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So when you want to go and stay at a Wander, it feels like you have your own personal concierge that's just purely dedicated to making your trip as incredible as possible. And obviously you can imagine the potential from there where my goal is to make the product so good and so complete that even if you aren't staying at a Wander, even if you're just trying to get back, it's like this is just sitting in your pocket. So I'd say that's the other really big feature that I'm excited about. And because we have the distribution to 200,000 plus people, you sort of have this great feature with a distribution moat, which is sort of the whole power of the platform.

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Bill Cilluffo:

I know company culture is really important to you. I mean, I've heard some interesting stories on frugality as one of the core aspects of it, but I'm sure that's only one of several key aspects to culture. I wonder if you could just talk a little bit about the Wander culture and you've learned from experience building a couple other companies. What are some of the hallmarks that you've tried to instill in the Wander team?

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John Andrew:

We believe in this idea of shared virtues, and I think that that idea really keeps the team tightly aligned. Certain things like tomorrow is a lazy man's today, or we can take a punch or just those different pieces. We don't walk by. If there's trash on the ground, we pick it up. And I think instilling that in the company very early is certainly something that you learn as a second time founder. You sort of learn the importance in your first company and you learn to document it and its importance, but it also sort of sets this tone and the ability for people to run on the same operating system, which is incredibly useful. And so even though Wander is like a remote company and extremely high output, the fact that we can have people from all over the world with different virtues and ethics and ideas have this shared operating language and expectations, I think is why Wander moves as quickly as it does.

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I mean, we're still less than three years old. We're going to turn three in about six months. And I think when you go to wander.com and you look at the company we've built so far, it doesn't feel like that young of a company and I really credit all of that to the team and to the culture we've built around it.

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Bill Cilluffo:

Some of this is you were sort of building in the middle of COVID, but you've chosen to build the company totally remote, spread around the world. Any regrets on that? Is that sort of totally working or are there places where you're like, look, if I was actually all in San Francisco or all in Austin, Texas or pick your location, it would be a lot easier to do what we do?

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John Andrew:

Coder was an all in-person company, and so I think a lot of startup founders, they've run in-person companies or they run remote companies. Very few have run both. And I also think very few have run high output versions of both. Coder was an incredibly fast moving startup, very much in line with Wander. I think that there are certain advantages to building remote company. One of the biggest is cost per employee, which I think is a metric that very few people measure. If you run a business that is distributed, in Wander's case, we have locations all across the US, there are certain advantages to having people nearby or just who understand the area. And then the other big piece is if you're going to have a remote company, you have to hire people who work well in a remote setting. If you hire people who are best in person and you ask them to work remotely, it doesn't work, right?

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It's kind of how a lion is not very comfortable in the Antarctic and vice versa. You take a polar bear, you stick it in the Sahara, it's not going to be happy. And so when you build a company, the types of people that we had at Coder, for example, we had many who were best in-person environment and then in Wander, the vast majority are best in a remote environment. It's something that we interview for, certain personality traits, organization, those different pieces. And so I think that a lot of companies that struggle and end up wanting to do hybrid or XYZ, well, a lot of them built in-person cultures to begin with. And so if you built an in-person culture, it went remote during the pandemic, now you have this hodgepodge and it can be pretty difficult. I think a lot of people who try and build a remote company hire people who are best in office, and that also is difficult.

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So I'd say if you're not taking advantage of the benefits, managing your cost per employee and access to global talent and hiring people who are best remotely, then you should 100% be in office. I'm not an either or person. I'm not super remote or super pro in office. I love offices, I love grinding with my team. And then of course I also love working late at night in my apartment, and I can do either. I do think it's an inevitability that Wander at some point needs a real mailing address, but we'll see when that is. Offices are expensive, which kind of comes into the frugality piece of I hate spending company money, and so it's hard for me to justify a fancy office.

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Bill Cilluffo:

You got 50 properties in the portfolio, so maybe you can just have a rolling office when they're not being utilized.

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John Andrew:

Yeah, totally. Yeah, absolutely.

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Bill Cilluffo:

That's awesome. Well, look, you talked about how strong your culture was and how important that is. I would guess that it's harder to establish such a stronger culture remotely. Maybe I'm wrong on that. Having done that in person with Coder and now done that remotely with Wander, how could you contrast and think about learnings on what needs to be different in that regard?

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John Andrew:

Yeah, so with an in-person culture, a lot of it is visual. You see what other people do, how they talk, how they think. In a remote culture, it's very much written. It's written and it's output, which I think is probably the easiest way to think about it. In an in-office culture, you're looking at a lot of input. Are they at their desk? What time did they show up, et cetera. Versus for a remote company, it's really purely output, which I tell the entire team, I will measure you on your output. I don't care how many hours you worked or whatever else, if it didn't get done, then it didn't get done, which can sound pretty hardcore. And obviously anyone who works with me knows I'm an empathetic leader, but it's very difficult to manage people on their input in a remote world.

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And so I would say that's probably the biggest thing is that in-person is very visual, it's very input oriented, and you have to make it an effort to manage to the output. And remote is very much measuring the output and obviously you have to be cognizant of the input.

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Bill Cilluffo:

Cool. How would you articulate your best superpower? And conversely, is there something in particular you can point to that you wish you were better at or you're actively working on?

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John Andrew:

The thing that I'm best at is taking a group of people and aligning them towards a singular goal. I think that's probably the thing that people love the most is the comradery and the teamwork and the excitement and the motivation and this understanding that we're going to get this done and it's going to be incredible. There are of course a lot of other things to that end that I truly love. I love working with the design team. I love working with the product team. Candidly, I love every single aspect of building a company. I love it. There's no piece of building a company that I haven't fallen in love with. One thing as a company scales is as a founder, you need to learn new things. Wander is reaching a pretty significant scale very quickly, not just in terms of people, but also looking at our plan and the fact that we're hitting it.

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If this trend continues, it's a pretty decent sized company in six months, a radically different one than it was six months ago. I mean, for context, it took about a year, a little over a year for us to add our first 13 properties, and it's like now we're going to add that in a month. That's a big shift. The month after that is more, and then it's more after that and it keeps growing, which I know is how it's supposed to go. But what comes with it, and this is something that y'all have taught me, is almost this idea of managing the back book or managing to the metrics. As a founder in the early days, you're so busy at the front of house, talking with customers, designing the menu, cooking all those different pieces, but at a certain point, using the restaurant analogy, you have to go into the back and you have to dive over your financials and dive over your metrics and how many tables turned and if we change this just a little bit, what efficiencies are created over the next year.

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And that's just something that when you're in the midst of the chaos as a founder, you don't tend to see that you need to go and make that transition. And of course you get to do the rest of the fun stuff, but it's like, hey, you need to spend a few hours in the closet managing that back book. And that's something that having a good board is really useful for because you all have a bird's eye view of hundreds of companies and different stages, and as a founder, you are in it. And so that's one thing that I've really been working on as a founder. And candidly, I've fallen in love with that too, which Chucky finds very entertaining that I reference it like a video game, this idea of hitting plan. But I'd say that that's one thing that I'm really actively trying to master, which I realized too, of course, if this becomes the company that I hope it can be, if we're so lucky, it's really important having that repeatability and making sure that if we eventually went public, that we don't miss our quarters and that kind of fun stuff.

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Bill Cilluffo:

No, it's awesome. I love the introspection there. We had a chance to talk to your CMO, Kyle Tibbits, as part of the research for this interview and asked him the superpower question. And let me just share a bit of his answer. John Andrews is an incredible servant leader. The more you know about him, the more it makes perfect sense that he's building a hospitality company. A couple of years ago after filming a video at one of our properties, I was leaving to head back to my house, which was three hours away. He insisted on driving me himself. We stopped for lunch and had an incredible three-hour conversation. Interesting to hear the kind of hospitality nature given what your business is.

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For what it's worth to the leaders, I had the same exact experience with you where you came and picked me up at the airport, brought me who knows how far away to the number one ranked barbecue place in Texas, and we sat in line for an hour and a half waiting to get in there and had an incredible meal. So kind of that orientation to people that matter is pretty stunning and it's clear you've got an amazing following within Wander, so congratulations on building such an awesome rapport with folks who are working with you.

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John Andrew:

Thank you so much. Yeah, and that barbecue was great.

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Bill Cilluffo:

It was pretty darn killer, that's for sure. It lived up to its ranking. We're getting close on time here. There's probably two questions I'd like to finish up with, one which came from Kyle. So if you had to pick one Wander to live in for the rest of your life, which one would you pick?

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John Andrew:

Gosh, to live in for the rest of my life. It's funny because I'm going to overanalyze the question. It's like, okay, I want kids one day, so it's like how many kids? And then I'm going to get old, so which ones have an elevator? That kind of stuff. I'll simplify it. I'll take all those variables out because otherwise it's going to get too complicated. I would probably say Bandon Beach. You have obviously Bandon Dunes Golf Resort right there, which is absolutely incredible. You have the beach and just the Pacific Northwest and the feeling that you get out there is pretty magical. So I would do that, though once I had kids, that house would get pretty cramped.

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Bill Cilluffo:

Dynamite. If you had to go away for a three-day weekend, which one would you pick?

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John Andrew:

You're going to hate me for this answer but, candidly, they are all spectacular. That is the whole idea. The whole idea is that they're all perfect and it's literally just like what flavor of ice cream do you want? It's all ice cream.

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Bill Cilluffo:

So you can't pick among your children. I can respect that answer, but I've heard from you and Chucky, Bandon is ... obviously have shared the golf course before, so I will definitely get to the Bandon place soon. Last question, and we tend to end all of our interviews with this, hopefully we've got a number of young entrepreneurs who will be listening to this sooner or later. What's one tip from your multi-pronged journey that you would share with a young entrepreneur thinking of starting a business?

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John Andrew:

It's incredibly important to be a good person as you build a company. There are so many moments that you face with difficult decisions, whether it's letting someone go or how you present yourself in a meeting or what investors you work with. And so having a very correct and empathetic moral compass I think is pretty important, which of course, there are a lot of very ruthless business leaders who get through and not saying that you don't need to be ruthless to a certain extent, but you still need to be a good person and conduct yourself well. The other thing is that if you're smart and you're kind and you're working on the right idea and you're unafraid to pivot, you will be successful. It's just a question of how long it's going to take. And obviously I realize there's a lot of variables in there working on the right idea, unafraid to pivot, et cetera. But I think that that's one thing that a lot of people should recognize is that it's certainly possible.

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It's a recipe, and just be kind, work hard, make adjustments, have that courage, and I'm certainly rooting for you. I know that there's a lot of people who, for whatever reason, root against companies to fail. But yeah, for whatever it's worth, I'm rooting for you. And my guess is Bill is as well.

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Bill Cilluffo:

No, that's awesome. I love the advice. Well, look, John Andrews, it's been awesome having you and sharing so many of your stories from the past. I'm sure we could have gone way longer, but I'm sure you're quite busy in the process of building Wander. So we'll let you go and really appreciate you spending the time with us today.

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John Andrew:

Thank you so much for having me. It was awesome.

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Bill Cilluffo:

Perfect. And to all you listeners, take care and thanks for listening.

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This has been the FinTech Thought Leaders podcast, your window into the world of venture capital and financial services with today's digital disruptors. QED is proud to provide the best FinTech advice you can get. To learn more or to read the full show notes from today's episode, check out qedinvestors.com and be sure to also follow QED on Twitter and LinkedIn at QED Investors. Thanks for listening.

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