John Andrew Entwistle - How to make the right decisions in the most crucial times!

There are 2 types of decisions. There are reversible and non-reversible. And if it's a reversible decision, you wanna take all the data and make it quickly. If it's a non-reversible decision, then your accuracy is far more important. And I find that humans are one of the few creatures in the world that can see the future. The thing that I would recommend to anyone listening, looking for some type of action to take out of this, is start tracking your accuracy in your decision-making. So one thing I started a long, long time ago is I would write down The decisions that I made and then retroactively see if they were correct or not in hindsight. So if I said, this is how we should do it, and it was wrong, then I will go back and say, okay, like that was incorrect. And then I'll literally have an accuracy score for that day, for that week, for that month. Mm-hmm. And it doesn't need to be something that's like super intensive. Like you don't need to, you know, kill yourself over it. But the idea is, is that you'll realize for a lot of people that you're saying things in absolutes, you're thinking about things like so concretely and saying it, and then it turns out that you were wrong. I think a lot of people would be surprised, like what their actual percentage was.

Welcome to the Undefeated Underdogs Podcast, where I unpack and narrate stories of ambitious people who turn obstacles into opportunities. My goal for this podcast is to create a platform to narrate underdog stories and maybe play a small, teeny tiny role in inspiring you. I intend to highlight the underdog mentality and make authentic conversations with people who play the long game, take action with a chip on their shoulder, and convert obstacles into opportunities. Buckle up as I'll be bringing some authentic founders, VCs, community builders, and content creators who got underestimated their whole lives, and yet they beat all the odds to become insanely successful. Now today I want to tell you a little bit about our awesome sponsor, acquire.com. Selling a business is as tough as building a business. As someone who went through this process once, selling my own startup, I know the pain it takes to get to the end zone. This is where our sponsor shines. Imagine this, you're a founder who's built a solid SaaS product, acquired customers, and generating consistent monthly revenue. The problem is you're not growing forever for whatever reason— lack of focus, lack of skill, or just plain lack of interest— and you feel stuck. What should you do? The story I'd like to hear is you buckle down, somehow reignited the fire, get past yourself and the clichés, and start working on your business rather than just in the business. You start building an audience, move out of your comfort zone to do sales and marketing, And in 6 months you tripled your revenue. The reality isn't as simple. Situations may be different for every founder facing these crossroads, but too many times the story ends up being one of inaction and stagnation until the become business— the business becomes less valuable or worse, worthless. If you find yourself here or your story is likely headed down a similar road, I offer you a third option. Consider selling your business on acquire.com. Capitalizing on the value of your time is a smart move. Acquire.com is free to list and they've helped hundreds of founders already. Go to try.acquire.com/shirath and see for yourself if this is the right option for you. Now let's get into today's episode. King the Wander hoodie.

The hoodie is looking great, dude. It's a great vibe. I love it.

Ah, thank you, man. I appreciate all kudos to Wander. Welcome, welcome folks. Welcome to the Undefeated Underdogs Podcast. You just got a sneak peek of who I'm interviewing right now. Without further ado, John Andrew Entwistle, the CEO of Wanderer. Welcome to the show. How are you feeling, man?

I'm feeling great. Life is good. Sun is shining. World is spinning. I'm on with you. Super appreciative to be here. So, yeah, stoked.

Thank you. And for folks who are watching this video, I'm actually rocking Wanderers hoodie. It's one of my favorite hoodies. It's cozy. It's like that, like, you know, John was selling. It has that vibe, you know, the Gen Z vibe, which I required as a millennial. But

looks great. Yeah, you look good in it. It's a good color.

Yes. So the— I was one of the, I think, founding members, I guess, uh, when you guys launched the $100 membership. Yeah. So I just quickly—

there's not many of those. There's over 200,000, well, close to 200,000 users on the platform. And sub-2,000 founding members. So it's a pretty special group.

Wow. Okay.

We'll be doing an event soon, so we'll have like a big event at one of the properties and everyone's going to be invited. It'll be a great time.

Awesome.

Yeah.

Awesome. Yeah. Looking forward for that. For folks who don't know John, let me give you guys like a brief intro. John is a dynamic founder CEO of Wander, a venture innovating the short-term rental space, delivering quality, high-quality experiences, I would say, for travelers who want change, who are fed up with the hotel system, all the Airbnbs and whatnot. The beautiful thing about Wander is Wander owns all the properties, so they have this amazing human touch and the detail, attention to detail, and the care they put in all these properties make it you know, unique, right? He's also— he was the co-founder and CEO of Coder, a venture back in the day, made strides moving the development workstation to the cloud. So I want to talk about that experience as well.

Yeah.

And he was featured on, you know, Forbes Under 30 in 2019. That's a massive feat. And he received prestigious Thiel Fellowship, which 100% I want to talk about in the episode. taking a break from traditional, you know, college path, spending 2 years honing all skills that you're kind of mastering right now. John, what an inspirational journey so far. I'm pumped, excited, fascinating entrepreneurial journey, I would say, you know. But right off the bat, let's talk about Coder. Like, you were kind of with, I think, other 2 founders. You've build this platform. What happened? What is the transition like coding the software SaaS, like, you know, all that world to real estate? That's a big leap, right? So talk to me about that journey.

Yeah, absolutely. I can sort of give like a little bit more context because obviously, you know, there's like a little bit of a jump from just like your daily life into starting what turned out to be a pretty decent sized venture-backed company. I've always been passionate about computers and software and building. I really attribute a lot of that to my pop. He was a single dad and constantly working. And as a kid, I would watch him work and be like, I want to work like him. And so I ended up starting a few companies when I was a kid, 13, 14, that did pretty well, like low 6 figures in revenue. I always joke meant that I wasn't focused on my homework much after that. But it was really that experience, right, and getting to build and to fail and to learn at such a young age that really kind of just made me obsessed and passionate about building companies and product and brand and what that could mean. As you can imagine, when you're a kid, this idea that you can have outsized impact by collecting all these people and working towards this shared vision. It was just really empowering. And so that's sort of why I fell in love with it. In terms of starting Coder, so during those years, I met my co-founders, Kyle and Amar. Amar was one of the system administrators. Kyle was an engineer. And we would spend dozens of hours just talking on Skype and working together and building these things. And the idea for Coder was actually Kyle's. I remember the Slack or the Skype message like it was yesterday. He was like, I have an idea. And my initial response was like, I'm in. Like, it wasn't like that with our relationship back in the day. It was like, let's just do it. We were, you know, kids just building companies. Yeah. So yeah, we ended up moving down to Austin. You know, I didn't, didn't go to college. You know, we already, we started Coder while I was in high school, which I was doing online. So that gave me a lot of extra time and freedom. Which is something that I definitely recommend to young entrepreneurs. If you're in high school and building a company, talk to your parents about potentially having some flexibility. I'll warn you that socially it's a little bit more difficult, but yeah, having that freedom and time as a kid is really special. And so, yeah, started the company, ended up doing pretty well. We raised about $45 million, now has a bunch of massive enterprise customers and Ran that as CEO through ages 18 through 23 and all the way through Series B. So,

wow. So that's, first of all, at the age of 18, kids are spending in beaches, right? Like they're spending spring breaks and doing all sorts of nonsense, most majority of them. But it's so fascinating to see that you have a You have a set of clarity and a straight path that you want to achieve. So talk to me about at that age, you're prone to distractions, right? Like, you're kind of— there are so many things you can go— it can go wrong in many ways. So how did the hell John, the 18-year-old John, stayed in the path? Like, okay, this is what I want to do for the longest continuous of time. Like, what driven you? Do you have mentors? What— who helped you, like, push you if you're taking, like, you know, bad decisions or making wrong moves?

You know, I've always, I've always been very goal-oriented, you know, constantly moving towards what your objectives are. And thinking in pretty massive time increments. Speaking more personally, candidly, it's a little bit of a flaw of mine. It's like I'm 25 and I spend so much time thinking about and building the future that a lot of those distractions I just skip, which isn't necessarily a good thing either, right? I think it's hyper important to go out and spend time with your friends and these events and those different things. So it's actually something that I actively have to work on is saying like, okay, like go and have some adventure, go out like and do something with your friends or otherwise, as opposed to like just being focused on the company. Like if you look at my calendar for just the last week, because we're recording this on a Friday, it's like I've had 7 flights this week. Like I've been all over the place. That's why like my background and hair and everything is a little bit of a mess. So people have to excuse me because it's been

No, no, no,

it's been a rough one. You

look like a million bucks, man.

Thank you. I appreciate it. So, yeah, I mean, for me, I would say that it's just a part of who I am. And I'd say that got instilled in me at a pretty young age. I sort of set rules for life, what I wanted to do, who I wanted to be as a person, what I wanted to accomplish. And I'm a firm believer in this idea that Like, there's only a few things that we know to be true. And one of them is, is that we only get one life, or at least that's what it seems like, depending on your religious beliefs. And I just want to make the most of it. Like, I want to have as few regrets as possible. I just want to be a good person. I want to treat people right. I want to be kind. I want to accomplish as much as I can, help others accomplish their goals. And yeah, it forces you to take a pretty zoomed out— point of view, which when you think that way, it can make it hard even to enjoy the little things to a certain extent. But yeah, it's a double-edged sword, I guess, is what I would say. But for people who struggle with the opposite, I would say to really zoom out and think about your life as sort of this book that you're writing each and every day and to think about your chapters and what you're going to be focused on and work backwards from your goals. And if things aren't moving at the pace that you want, then You may have to be a little bit more focused, but I highly recommend balancing it all. And also, of course, working on something you love. Like work-life harmony, I think, is a really important concept, you know, where your work and your life are so intertwined that you can't tell the difference.

Yeah. So for some, I think mostly people who are very passionate about building something for themselves and putting it out and finding people like themselves. everybody loses the touch of, or at least which is what, which is life, what is work, right? Because it's all in the background. We all constantly think about what about this feature, what about this experiment.

Totally.

So that hustle mindset is always like on. But why do you think about— when you said it's not a good thing. Elaborate. Like, do you have any regrets in your—

Yeah, certainly.

Past? Past? Like, you know?

Yeah, I mean, I didn't go to prom because like I was too busy working on my companies. Like, you know, like I put off like dating and like seeing friends and going out. I mean, like, you know, most kids are like going out and partying and Like, it's like I wasn't going out and drinking. If you looked at my weekends, and this is still true to this day, like my weekends I spend working. And so it's, you know, the flip side to that, of course, are the adventures that I've had and, you know, like the, at least the accomplishments on paper. I still don't view myself as successful, even though I realize that that can sound weird. And so, you know, it's one of those things where you, there are certain moments and times and memories that you'll never get back. Like, I will never be able to go to prom again, right? It's like that chapter is closed. And if I did, it would be weird, right? And so there are certain moments too, like when you have a kid, right? That kid gets older no matter what you do. And so you can never get that time back with them. And I realize that that's a popular opinion specifically for older entrepreneurs. where they advocate the importance of not losing track of those moments. But it's something that I'm even cognizant of today. And that's not to say that I am not working literally every single day of the week, but I find it very important. And this is even something that my board advocates to me is like, they'll be like, John Andrew, are you getting time to go and do the things that you're also supposed to be doing? Which theoretically also makes you a better operator, you know, getting a little bit of a breath. So it's certainly a challenge. I think a lot of people, you know, probably suffer with it one way or the other and finding that balance. But yeah, I can say that I have certain regrets where I closed certain doors in pursuit of my goals. And for the most part, 90% of those doors were good to close. But there should have been a few that I was more open to.

And how do you handle regrets?

Yeah, so I actually love fixing them. Um, like, if, if it is fixable, like, I will go back. Like, a funny, a funny story. Um, so one of my— the other day I was out to dinner and I was talking about, like, my childhood with, you know, whoever it was, and this memory popped into my head that One of my friends was having a birthday party and so was another one of my friends. And so I was like, okay, I'm going to split the time. I'll go to one and then go to the other. What ended up happening though was that a lot of people ended up going to that second person's party. So there were far fewer at the first ones. And I recognized that and I wish that I had been like, okay, I don't need to go to this second birthday party. I'm just going to stay here with my first friend because there's less people here and that's more important, that's more meaningful. And so that was always a regret of mine, which sounds stupid, right? The types of regrets that John Andrew has are relatively silly in that context, but it bothered me. And so I reached out to him, haven't talked to this kid in 15 years or whatever. And I was like, hey, dude, I wish I'd stayed at your party. And of course he's like, oh, don't worry about it, whatever. But yeah, I just like, I like to make things right if I make a mistake and fix them. And not even if I make a mistake, but if I, if I wasn't like great.

Mm-hmm.

And if, if there are times too where I can't go back and fix it, it's like recognizing it, apologizing for it, and then again, doing what you can to make it right. Or if not, making sure that you never make that type of mistake again. Because obviously we're not perfect. I mean, we're all super far from it, but I think the pursuit is important.

We're all work in progress. Nobody's perfect. We're all like this book that never ends till our last breath. So what you said is true. The best way to handle regrets is having closures. And for some things that you can't go back in time, You just have to find peace with it. You just have to sit with yourself like that. The prom thing you said, you just have to make yourself like comfortable with it by not being there, you know, at that age, going to that event, whatever it is, that particular, you know, in this season, right? Yeah, absolutely. I think closure is such an important thing. I do practice that, and sometimes it's hard. Because it not only makes you uncomfortable, it is weird, right? Like, you, you kind of are welcoming or digging in to these memories that, that really hurt you, right? And it takes a lot of courage. So I appreciate, appreciate you for, you know, sharing, sharing those things, you know, on this show.

I think the big thing that I would advise to people too, to whoever's listening is to also be cognizant of minimizing regrets as you make decisions. Like, a regret minimization framework I find is super important. And what I found is, as I get older, candidly, I have very, very few regrets. I mean, maybe it'll be like, you know, one at one once a quarter, as opposed to, like, you know, when you're a kid, it's, it's far more frequent. And again, those regrets, like, the regrets that I have are like very, like, small potatoes. Like, I'm very self-reflective. I'm like my own worst critic. And so I'm constantly striving for it to be the best that I can be and handle every situation perfectly. And that's obviously not easy, but to recognize and look through that lens and really focus on your accuracy in your decision making, I think is a really important thing, especially for young people. You'll notice that if you do that over the course of months, years beyond, that all of a sudden your life just becomes like a lot smoother.

And I think most of the regrets happen because we tend to make decisions that, that reason, you know, that might feel like good in that moment, but, you know, in retrospect it feels bad, right? And talk to me about like your decision-making. Do you have any frameworks that you use now that you're a You're a quite successful founder, right? It's not, it's not your first endeavor. You've built so many companies, you've raised millions of dollars, you hired so many awesome talent working with you. So it's a tough job. So that means tough job means tough decisions, and sometimes you have to make it quickly. So explain or elaborate your decision-making process.

Yeah, so there are 2 types of decisions. There are reversible and non-reversible. And if it's a reversible decision, you want to take all the data and make it quickly. If it's a non-reversible decision, then your accuracy is far more important. And I find that humans are one of the few creatures in the world that can see the future, right? There's this idea, and I'll give an example, that if you have a lot of time to think about a problem, you're more accurately able to predict the outcome, right? So if we were to use like a math equation, for example, if I was to ask you like, what is 46,399 divided by like the square root of like whatever, like that's a complicated thing that you can't like do in your head off the bat, right? Or at least I certainly can't.

No, I can't.

But if I gave you an hour and a pen and paper, then you could. Right. And if I gave you a month, then you would've triple checked it 1,000 times and you would have certainty. And so it's this idea that in certain problems, especially ones that are complex, when you have the right tools and the right amount of time, you can be fairly accurate. Now, of course, things change in a startup very quickly. There are all these external variables. It's not as black and white as a math problem. And so you have to redo the problem multiple times. You have to check and make sure that everything you assumed is correct. and those different pieces. So that's sort of how I think about it, is this problem reversible or non-reversible? And if it's non-reversible, how important is it that I get it right? And then I'll allocate the appropriate amount of time. Now, I won't reach this point of being paralyzed in my decision-making, but as you get further into your career, and this is something that Jeff Bezos is famous for, It's the importance of being correct as an executive. One of Amazon's virtues is that we're right a lot, and I think that that's a really important idea. The thing that I would recommend to anyone listening, looking for some type of action to take out of this, is start tracking your accuracy and your decision-making. So one thing I started a long, long time ago is I would write down the decisions that I made and then retroactively see if they were correct or not in hindsight. I would look at were the things that I said accurate? So if I said, this is how we should do it and it was wrong, then I will go back and say, okay, like that was incorrect. And then I'll literally have an accuracy score for that day, for that week, for that month. And it doesn't need to be something that's like super intensive. Like you don't need to, you know, kill yourself over it. But the idea is, is that you'll realize for a lot of people, that you're saying things in absolutes, you're thinking about things like so concretely and saying it, and then it turns out that you were wrong. I think a lot of people would be surprised, like what their actual percentage was. Mm-hmm. So I really strive to be as accurate as possible now, and I'll even express like how sure I am because I hate being wrong, like in that context. I shouldn't say I hate being wrong. It's just like something I strive not to be. And so I'll say, like, I'm 80% sure. And then even giving the team that variable and saying, I'm 80% sure, but there's a 20% chance I'm wrong, then they'll be like, okay, that's enough wiggle room for us to go and hedge progress, for us to go and explore other options so that if this ends up not working out, then we know what we're going to do and how we're going to pursue in the future.

I love the way you framed your answer. It seems like you solve it as a problem, everything that comes your way, right? I love that because when you put it in an example saying, if I give you 1 hour, the outcome is different. If I give you this tool, the outcome is different. If I give this much time, the outcome is different. Oftentimes in startups, and I think you can chime in here as well, people miss those variables. Everybody wants to solve a problem, but what they lack, including myself, most of the time is I have to give enough time for myself to solve this or find enough tools or resources or people. To actually contribute to that problem so that we can solve together, you know, if it's a team or individually. And that is really important. I love the way you framed, and when people approach decision makings through problem solving and put it in a way with added resources at a time, probably like, you know, the accuracy bit will improve over time. One curious question, you said You will state the accuracy when you communicate your team or, you know, when you make addition. Couple of questions. When were you 100% sure about addition? Can you explain? Can you all— can you share some of the moments that you are like, wow, this is like bang on? And you look back like 10 years ago and like, okay, these are the 100%. And talk to me about which went wrong too. Like, yeah, I'm 100% sure, but the outcome is not 100%. So yeah, 2 questions there.

Yeah. So I would say first of all, that 100% certainty is exceptionally rare. That only happens on things that are black and white. You know, getting to high certainty and having them work out well is actually like a pretty common occurrence. I can look at Like the team, the branding decisions that Wander has made, like all of those different— I mean, there are so many. Candidly, building a successful company. And to be clear, again, like, I view myself and my career and my companies at such early stage that, like, I would never say that they're successful, especially, like, when you consider, like, the ones that truly are. So I want to make sure that everyone like understands that within, within the context.

So one thing I have to, I have to tell people as well, you're very modest. You can tell, uh, John, because you've done— and the resume itself is so impressive. So, uh, I just want to acknowledge that you've done phenomenal work, but I will, I will, I will, uh, work with you in, in the, in that topic that you're still early, but to me, I think, you know, you're, you're at least for me, like, you know, 5, 6 steps ahead of me.

Well, yeah, I appreciate that. And you're, yeah, you're gonna, you're doing phenomenal things as well. So, um, yeah, so anyway, like what I was saying, there are very few decisions that are 100%. The majority are high 80s, high 90s, and those tend to work out well, and they tend to be pretty pivotal. Right. Talking about whatever domain or handle, like, to pursue a certain strategy that everyone says will not work, but you've done the math and you think that it will. I think the ones that are always unfortunate is that when you have a pretty high conviction that you're correct, yet you end up being incorrect. And so it's really important to constantly, again, reevaluate if the decision you made was correct, and then if not, what variables changed? You asked me what decisions I've made historically where I thought I was doing something correct and it was just wrong. All of them had to do with external variables that ended up turning against my favor. I've had it countless times where I'll interview users for a new product and all of a sudden, over the course of 5 months, there's some type of massive shift in consumer behavior or the macro or otherwise that now the idea doesn't work. And that's why you hear a lot of founders and VCs talk about this idea of timing. Timing is also something that's so critical and also why speed is really important as well. I'll give you a great example, like starting a crypto company. I mean, gosh, however many years ago, like back in the early days of crypto, Right? Could be a great idea. Maybe you'll build the Coinbase, right? There's so much blue ocean starting a crypto company today, especially let's just say it's like a wallet company or something. It doesn't really make any sense. Like, there's so much competition, the timing's terrible, there's no VC funding. And so, and like, the users aren't as passionate about it in the current macro. And to be clear, like, this is not a hit on crypto. Like, I'm a huge fan of blockchain as a technology and beyond, but— Right. I was just giving an example of like how timing really affects things. Right. So I'd say that those are the big ones, is that the sand began to shift underneath my feet and I wasn't paying attention fast enough. And so I was still obviously like very quick in adjusting course, but I would say that that's really the big thing to watch out for is are things changing? Are the variables changing? And then candidly, the best way to do it is just make the decision again. So like, you think about it, like, I'll give, I'll give an even better example. Like, ask yourself, would I hire this person again? Like, they can be at the company, they can be working for you, they can be doing great things, and just ask yourself the question, like, would I hire this person again? And if the answer is no, then obviously something changed and you need to make those adjustments. Mm-hmm. And that goes for product decisions, branding, marketing, all that sort of fun stuff. So I, I, I think it's good to to ask yourself the hard questions over and over and over again as time passes and variables change.

And when those— first of all, that's an amazing answer. I love the way you said, you know, you are right in a way, but the variables are wrong, meaning, you know, the timing is wrong, the people change, behavior changes, and all that. How do you handle such moments? Like, when you put so much effort, this is a lot of people give up there. I don't know if you can see, uh, this is a little blurred.

Yeah, I can recognize it from the blur. The—

you are here. Yeah, this is like, this is pointless. This is one of the famous, um, things Jack Butcher did, one of my favorite creators. He's the number one guest on this podcast, grateful for that. I love that because around that point where, you know, it's like kind of like a boiling point, right? Like if you push yourself a little bit, you will make it, right? People give up because they surrender to external constraints or, you know, variables. So how do you handle those situations? You know, how do you pivot so fast, adapt to the situation? Where do you find that energy and courage?

Yeah, so I guess the first thing that I'll say is that like I have a remarkably like high pain tolerance. Like I just like, I just can't quit. Like I would have to like, you know, be dead or like paralyzed to like stop working, especially on something that I believe in. In terms of that being said, if you're working on something that is a wrong idea or the wrong strategy, just trying to power your way through it won't get you where you need to go. It's just going to be extra painful, an extra amount of time, and it may not work. If you think about it, does it make more sense for me to go and dig a hole with a shovel or go and find an excavator? And a lot of founders will just go and start digging with a shovel. And it's like, that's where you need to be a little bit thoughtful. You need to plan, you need to do all those things and really strategize. It does take a lot of— I mean, courage is the right word for it. I actually found myself reading a book about the importance of courage to reestablish that in myself. As you continue along, right? It's like when you're running a company, of course, again, you're wrong some percentage of the time and that can cause you to lose courage. And so it's like you have to figure out that balance and ensure that that core piece of yourself stays true. But to tell a little bit of a story, and I'll never forget this, at Coder, we spent probably close to 2 years building our first product. It was a consumer IDE. We built it ourselves. It was in the browser at the time. It was groundbreaking, right? Because You have to remember that like the stuff didn't really exist and we had just launched and we saw users start to skyrocket. We had raised our seed round from Redpoint and Uncork. It was like a $4 million seed. And again, at the time I was like super young, like I couldn't even drink. And we turned on monetization and no one paid. 60,000 users, no one paid.

Wow.

And I remember looking at that, looking at this 30-person team and talking with my co-founders and saying that this is the best way to monetize and that if this doesn't work, it's not a matter of refining the product or whatever else, it's just, it's not working. We need to pivot, we need to adjust. And Even though we had plenty of cash in the bank and the like, within, call it a week, we made the decision to start the pivot. We explored 3 options, ended up going down the enterprise route, moving enterprises' development environments to the cloud, which ended up being the right decision. And ended up having to let go of some incredibly talented people who were working on parts of the company that were no longer relevant. And so we did that all in a very short amount of time, a lot of which was because when you're losing money, when your company is losing money, time is not your friend. And so for us, it was just all about the speed of execution. And it certainly was scary and it sucked, and the morale was terrible inside of our little office. I mean, I even like remember buying an office cat to try and like cheer people up. Like, wow. It's like, you know, like that kind of like silliness. Yeah. It's like the vibe was super down. It's like we worked so hard on this product and we are shutting it down.

Right.

And when I say work so hard, I mean 14-hour days plus every single day, including weekends. And that was for the team. Like that wasn't even just for me as the founder. That was like the entire team. People like gave their, like, you know, their soul to pushing. And we ended up building something that was incredible, but it certainly wasn't something that people were willing to pay for. And then, you know, 3, 4 months later, we got through that, you know, like those moments. We ended up launching CodeServer, which is now one of like the most broadly used developer tools out there. It's like millions and millions of downloads and all that sort of cool stuff. And then, you know, now it's like you have all these massive Fortune 500 companies that like write their software on Coder. But it's, yeah, it's hard and it sucks, but you have to be very candid with yourself. I think, yeah, you need to have some courage and you need to push through.

And what was the book? I'm curious, what was the book you read?

I can't remember it off the top of my head. I'll pull it up while we While we chat. I promise I won't like start doing emails or something on you.

No, no, it's fine, it's fine. Uh, you— that's, that's amazing.

Courage is literally in the title, which is fine.

Courage to Be Disliked? I, I think it's,

uh,

because it's, it's one of the famous books. Uh, I was—

Courage Is Calling: Fortune Favors the Brave by Ryan Holiday.

Yeah, awesome.

Yeah, great book. I recommend it.

Yeah, first of all, let me tell you this. It's really, really amazing to hear that story. You know, all of your answers are so amazing because you have like a— you have an innate story behind it, and I love the way you kind of like, you know, bring them to life.

Yeah, every— everything that I've learned is through experience. And of course, too, I'm very lucky to have some incredible mentors. I mean, if you think about it, on Coder's board, you have legendary investors. Alex Bard, Glenn Solomon, Andy McLaughlin. Imagine having those people around you. Those are the people you're hanging out with as an 18-year-old, 19-year-old kid.

Wow.

And then your employees, right, are massively tenured. They've lived whole other lives beyond where you are. Those are the people that I was hanging around with. And so I'm very cognizant that who I am today is very much a reflection of just how fortunate I was to be surrounded by such incredible people. And that's why, too, I always try and just remember that and learn as much as I can from everyone around me. Like, I'm one of those people who, like, when I meet someone new, it's like, I want to understand who they are and what they think and what I can learn from them, regardless of who they are, how, quote unquote, successful they are or not. Because obviously, like, everyone has something to teach us. But yeah, I can say certainly that, like, who I am is just a lot of, like, blood, sweat, and tears and being incredibly fortunate to be surrounded by such amazing people. And then also, of course, to be born in such an incredible country that gave me those opportunities to have a father who was willing to raise me, like, on his own. And then also, too, when you're handed this kid who wants to not go to high school and, like, wants to not go to college and doing all these things to support that. I mean, yeah, I am so incredibly lucky and And yeah, I think that— I think it would be ignorant to think otherwise.

Oh no, no, I appreciate you for, for telling that as well because a lot of pieces should come together, right? And I think this is, uh, this is a quote— not a quote, I might, might butcher this— Fred Rogers said this quite, quite many times, and I kind of reminisce, you know, once in a while. You're, you're the kind of you're the output of the people surrounded by you, and, and, and a lot of pieces should come together, meaning a lot of people should help you so that you make your dreams come true. It's not— so it's always— it's not an alone journey, it's like a together journey.

So yeah, no one, no one, no one can get here. Like, no one can get to this earth without the help of others. Like, if you think about it like that, it's like you can't even— you can't even be born Without the impact of others. And so, yeah, I think recognizing that is really important. And of course, too, it's not like life rolls out a red carpet for you. You have to increase your surface area of getting lucky, and obviously you have to work incredibly hard in that. And of course, too, I've had a lot of very unfortunate things happen in my life in early childhood as well. But it's recognizing, like, yeah, it's just recognizing, like, how fortunate you are and making sure that you don't waste that opportunity, I think, is super important.

Gratitude is a fuel, right?

Absolutely.

And once you have that mindset, it will never go away. Once you start thinking about what you have and what you want really fade away, you know, the desire to get what you want will slowly fade away because of what you have. And of course, we have to, we all have to, you know, chase some dream, chase an ambition, inspire others, and all that is on paper is really good, amazing. But personally, I think I like your mindset. One thing, how do you start from zero? Like when you set about, you build this incredible product at Coder, Spent 2 years, 30-people team, no output, nothing happened, none of the needle moved. You have to start from zero, you know, in a way. Talk to me about that, the transition, like, you know. Yeah. In that— at that age, What were some things that really worked for you that you want to pass on to others?

Yeah, starting from zero is difficult, but candidly, it's not the most difficult thing that you'll do. Really, I would say starting— I mean, people have quotes like back and forth on this, right? Like, because it sounds good, they're like, starting is the most difficult thing you can do. It's like, no, like, starting is the easiest thing. Like, building something is really difficult. And the other piece of advice I'd give to any founders or people working at early-stage companies is that it never gets easier. Like, point blank, never gets easier. Like, the problems just get bigger and more challenging. And the other thing to recognize is, if you're the CEO, there is a literal funnel of all of the most difficult problems in the company that make their way to you. Like, by definition, I work on the things that other people don't want to work on or can't. Right. And so like, you know, that's why like, you know, when I was a kid, like the people at Coder would call me like the shovel, because it's like I would just shovel whatever it was that needed to be shoveled. And so, you know, starting from, starting from zero is difficult. I think it's more scary than anything else. But like, I think a positive attitude and then building momentum is so key. Like momentum begets momentum. Like just get started, get like grinding, start working on it. Like, and again, plan beforehand is like the big thing I recommend. Again, like humans can see the future. Spend some time planning before. Like, let's say this, if it's going to take you 4 years to build a product, then like you should probably plan a little bit and like try and forecast if people actually want it. So that's my advice is like plan ahead of time. Then get to work, build the momentum, go quickly, have massively positive energy, and just check things off that list. Like, you'll make a list in the early days and check things off. And if it works, great. And if it doesn't, then adjust quickly, keep going.

Momentum. I think that's the key. That's the key takeaway. Momentum, I think, is the oxygen for any startup, right? If momentum dies, basically you're dead. Oh,

growth is so critical. I mean, and there's actually even like very logical ties to the public markets that you can draw on why, like how it's actually valued. Like you can assign a dollar value to the growth rate of a company. You'll have one company that's doing $1 billion a year in revenue that's growing at 10% year over year, and it'll be valued at $2-3 billion. Or you can have another one that's doing $1 billion a year, but it's growing 2x year over year, and it'll be a $10 billion company. And so it's not just like, oh, it's really important for team morale and all these things and the customer. It's like there's an actual enterprise value creation with your speed and rate of growth in a startup. Now you have to make sure that you're not growing to your death, right? You can't scale negative unit economics. And hire a bunch of overpaid people and all those different things, which is really hard, especially again, as your board is pushing you and things look good and all that fun stuff. You can't do that, right? But yeah, growth rate is super important. And there is a shift where it goes from creating an idea, finding idea market fit, to building a product, finding product market fit, to then for a founder, you end up making this transition to managing to the metrics. It's this idea of managing the back book. And that's something that obviously isn't talked about very often because so few companies actually reach that stage. There's so much content about the early days of a startup and all that fun stuff. I feel like there's a lot of founders who reach this point where, okay, now I need to scale. Things are going well and they're all left with no books, no guidance, No, like there's far fewer mentors, right? If you think about it, how many people like started a startup versus how many people exited something for like a great outcome. So yeah, it shifts. As you can imagine, your priorities shift, your job shifts, and the faster you do it, I mean, you're effectively like hiring yourself out of a job every like 3 to 6 months.

Right. Oh man. I have so many questions, but I definitely want to be mindful about the time. Talk to me about the Thiel Foundation. You know, how did you get into it? What kind of impact it made in your life?

Yeah, so Founders Fund invested in Coder's seed round, so that's how I had that connection. That was, that was something that The first person I met at Founders Fund was actually Peter himself, and he immediately kind of passed me on to the rest of the partnership. And they're incredible, by the way. What a 10 out of 10 firm in every respect, candidly. They're really solid. I mean, obviously I know that they're a little bit controversial, so not diving into politics, but—

Right.

They are a very good firm. And so I got pinged effectively from them saying, hey, there's this, the Thiel Fellowship thing, which I was aware of, but you should hop on the phone with this woman who is absolutely incredible and talk through it and see if it's something you want to do. Typically it's an application process. So I'm a little bit different in that capacity. Typically you apply, it gets reviewed, interviews, et cetera. You know, for me it was a little bit more like recruited. Hmm. But I went and did the interviews in LA. That was one of the last years that they did the interviews in person. And you get to interview with incredible people like Dylan Field, right? Which like, this was before Figma like exited. And so getting to like talk and hang out with him and Josh Browder and All these like really remarkable people. And you'll have to excuse my pups in the background.

No worries.

And so yeah, you know, it's like, went through it, was lucky enough to be picked. They pick about 20 kids every year out of, you know, they don't share the public numbers, but it's far, far a far lower acceptance rate than the top universities. Wow. Like by like a pretty massive amount. And I would say too, like the thing for us, like when I got in, we were just closing Coder Series A, so we just got on our Series A term sheet and we're closing that. And I'd say the most valuable piece was Just the fact that I wasn't alone. Like, as you can imagine, being like 18, 19, 20, 21, 22 and building a company is super lonely. Like, all your friends are going to college or like, quote unquote friends, because realistically, there's no founders who, like, young founders are putting their day in, day out who have many friends by definition, because you're giving it all to your company. So it's like, I should say all the people, you know, are going to college and doing all these things. And like, you're building this company and the stress and the problems you're dealing with are adult problems. And it's like, I have, you know, 30, 40 people, 50 people that if I fail, like they can't pay their mortgage. Like that's a big fucking deal.

Right.

Or at least I think it is. I know a lot of founders don't care about that stuff, but like I do. And so the idea that the Teal Foundation put together the 20 other kids in the world who are exploring and experiencing those same things at various stages, obviously, some were earlier than me, for example, was really cool. And some of those kids have ended up being truly great friends of mine. So I'm very grateful. I think that without it, I'd have— yeah, I would go from an already small group of friends to an even smaller one.

Wow. One decision or one bet, I would say, can change people's life, right? What are some bets you took in your founder career that actually changed people's lives?

I mean, gosh, I mean, all I do is take bets, right? Like starting Coder, certain product decisions, like accepting certain partners in terms of investors, scheduling meetings, like all those different things. It's constant who to hire, like all these different changes, strategy and directional shifts. I mean, yeah, I mean, who I am and where I am today is a collection of the positive bets that paid off, and then obviously subtracting the ones that didn't.

Of course.

So it's, yeah, I mean, I would say that like, it is literally thousands and thousands of decisions that I have had to make from everything from like, little product design to distribution and marketing strategies to approvals for spend or everything else, even what books that I read. And when I pick a book to read, I don't just go like, oh, what's a good book? I don't just go through a list of like, here are the 20 books that an entrepreneur needs to read. I'll think about what I'm struggling with and then hunt for whatever resource can help solve that. Again, we talked about the courage piece. I felt like That was something that I needed to re-up and that's a natural trait of mine, but I needed to remind myself of it. And so even that is like a bet, right? It's like I'm betting that it's worth spending the time for me to read this book and that it's going to have some positive output. So I know it's not a very concrete answer, but it's just there are so many bets that you have to take every single day. I mean, I've probably made like just today alone, like we finished probably like 6 hours of team meetings and budget reviews and goal reviews and all that sort of stuff. Because we do it on Fridays instead of Mondays because we like to work over the weekend. Like, again, like not work over the weekend, don't want to like stress people out. But like, I find it useful for me to do those reviews on a Friday so that I get to spend some extra time And like make that transition. So in any event, um, yeah, I've probably made like 100 decisions today already. That's, that's an overstatement. Maybe it's like, maybe it's like 10, 10 good ones, hopefully. So.

Wow, it's amazing. If you want to pinpoint, um, one other decision today, just today, that'll change again Not to reveal much, but—

Yeah, I mean, I can name one. So like I mentioned, as a startup, you transition from just finding product market fit to scaling, right? And you run into this idea of, again, like managing to your metrics. This is something that the Wanderboard, Alex Barton from Redpoint, and then Chucky Reddy from QED have been really exceptionally helpful with. And Basically, you have what you call plan, right? So it's like your pace of scale. So for Wander, it's homes onboarded, you know, like occupancy, like all these, all these numbers, users, et cetera, et cetera, et cetera. And so you have to, as a founder, basically like set and analyze that plan alongside finance. It's basically like the quote unquote boring stuff, right? Like, but it impacts the rest of the company because if I say, hey, I want to go from 10 homes a month to 25 homes a month by the end of, call it Q2, then what is that hiring impact? And then what's that burn impact? And then of course you need to ensure that those are all great people. And so a lot of the decisions that were made today was managing to those hyper-specific metrics and numbers and basically me Trying to forecast and set the future and say, okay, here are all the things that this company needs to do. And then the time that I spent was aligning the entire leadership team around that so that everyone knows exactly where we're marching and why we're marching. And then after this interview, just to walk you through the phase 2 of that is I'll go and record a video for the rest of the team because obviously I won't be able to talk to them all one-on-one. And we love async, so we don't like doing, you know, all hands where everyone needs to like ruin their day. So I'll record a video and explain exactly what we're doing, why we're doing it, the importance pieces to focus on.

Hmm.

And gain alignment. So, you know, it's one of those things where like, if Wanderer, yeah, I mean, effectively it's like the decisions that I'm making today are will determine like, is Wander fundable for a Series B in 6 months? And what scale is it? And did we expand internationally? And how many homes do we have and locations and all that fun stuff? So yeah, it's pretty important. And it's important I get it right too, like make sure that I do all of that within the constraints of the capital that we have and all those different pieces. Right. So

let's talk about Wander. First of all, that's amazing. Thanks for revealing that. Uh, let's talk about Wander. From coder to Wander, it's 2 different worlds. You're, you're dealing with 2 different things completely, like quite different spectrum, uh, at the end of different spectrums. So, A, why, why, why can't you just start another coder or be in the same space to maximize your impact with minimum effort and do even a great job like building some other developer tool or whatever it is? Number 2, why real estate? It's such a messy thing. It's like, do you have experience in that or how did you fit in?

Yeah. So Wander is obviously very different from Coder in terms of the end product, in terms of the customers. There are, of course, lots of similarities running one startup to the other in terms of the importance of team and culture and quality and brand and all those different pieces that do transfer regardless of what industry you're working on. I think that you can look at some great founders, and to be clear, I'm not comparing myself to them, But you look at like Elon, right? It's like Zip2 to payments company, which like you would say that's a big shift to then like SpaceX, like that's an even bigger shift. And then like electric cars. And it doesn't make us— it doesn't really make sense until you learn who that person is, right? And it turns out that Elon loved electric cars and wrote papers on them and as a kid would read books about space and sci-fi. And all of a sudden it starts to make a little bit sense. You know, like for me, like I would travel around with my pop everywhere and like I've been to, you know, every state, dozens of countries, like all before like I grew up. And that made me fall in love with hospitality and travel and like all these different pieces. And so when I, you know, when I stepped down from Coder, I was like, what do I want to build? How do I want to spend the rest of my life? Now, candidly, the idea for Wander was not something that I expected to build. It just happened to keep me up at night. I just couldn't ignore it. I had that idea shortly after stepping down from Coder alongside a lot of enterprise B2B type software companies. And Like I made an explicit choice that like after trying to kill the idea on paper for 3 months, that this is what I wanted to build and how I wanted to spend my life. Because I thought it would have an impact and make it more interesting. And I was certainly right. I mean, again, like, you know, I started, it's like this week, this week was San Francisco to Portland, Portland to Boulder, Boulder to San Diego, San Diego to Seattle, Seattle. Wow. I'm in Austin and then it's like, I'm here for the next like 2 days and then it's like on the road again. And it's like, what a great adventure. Like, so I think that, you know, it certainly is different than like what I had built previously, but also like building great software, building a great user experience, certain cultural dynamics or things that are just like who I am. And so when you look at Wander, when someone goes to wander.com, if they're ever wondering like, who is John Andrew? Right. It's like this company is a reflection of me in every respect. And it's obviously like not entirely perfect, but I'm certainly trying to make it so. And yeah, I feel incredibly lucky to be working on this company every day with the team. And we got very lucky that this idea turned out to be something that people wanted.

And it's again, like, real estate is such a traditional thing, I would say. Like, not many tech folks solved it, like, apart from, you know, the Airbnbs of the world. When you entered, do you know that you can't do it alone. Number one, you have to hire people, and I think you need capital and you have to raise money. How did you convince investors when it comes to like credibility for this particular problem that you want to solve? What was like your pitch and how did, how did you get their buy-in?

Yeah, I mean, I was fortunate that all of really all of Wander's early investors to some extent had seen me work before Encoder. They had observed how I execute, the teams that I build, how quickly I move. And I was very fortunate that that was something that meant that they wanted to work with me again. So that's probably not really actionable advice for a first-time founder, So I'll go earlier in my life to me raising my seed round for Coder. And it's actually very similar in the context of, you know, we didn't even have— I didn't even have a LinkedIn. It was like super young, like in my teens, still had no connection to Silicon Valley, knew no investors, knew no one. And of course, was also in Austin, which is not San Francisco, where like you can throw a rock and hit a VC. And so what I did was, is we kept building the product and I just started cold emailing people and I was like, this is what we're building, please talk with me. And what ended up happening was, is that it wasn't that they took the meeting because of who I was or my credibility. They took the meeting because the product was so radical and intense and real. And the branding was real and that there was clearly like this monstrous amount of work and effort that had been put into a company that hadn't been funded. And so when they saw that, when they started having the conversations and then obviously understood who we were as entrepreneurs and founders, then things very quickly shifted. And then as the product started to gain traction, then obviously it was a completely different story. So that's my biggest advice is like, show people who you are, show them how great you are, show them the output. And I promise you that a VC's job is to find high potential individuals and to fund them. And so you have to be relentless and show the world Like just what you can do and who you are. And then if you talk to them and show them from the time we started the conversations with those investors to the time that we closed the round, Coder had gone from like 0 to 60,000 users. It was like a product that was like people were massively excited about. And again, turned out that the monetization didn't work in that variant, but that's where like, who did you invest in also comes into play. And like the investors, you know, like they asked me, they said like, what are you going to do if you run out of money?

Right.

And my answer was that I am going to go to McDonald's and I am going to work as a fry cook and I'm going to feed food to my co-founders and we're going to keep this company alive. And they, they're like, okay, that's a pretty wild answer. Like you're supposed to say that you'd raise a bridge round or something. But it's like, we'll take it. And it's like, those are the type of people that you want to invest in, is you want to invest in a great idea led by someone who's never going to quit and this is their life. And yeah, if you want to raise money, you have to be that kind of person too. Obviously, a lot of bad people raise money as well. Sure. Um, but that's also why a lot of companies don't work out.

Right, right. I think, uh, 99.9% success depends on not giving up, right?

Totally. It's that classic Paul Graham essay, right? Don't die.

Yeah, don't die. Uh, I love that. And when you explored Wander, what was like the first initial— is— are you still pursuing the initial idea? Did you pivot? What, what are some lessons you learned? Because it's slightly different from Airbnb. Airbnb lets people come join their platform. It's like a marketplace. But Wander is something that you have that control, you have that end-to-end control, and you offer on top of it. Like, I love the feature. I might try someday. You also have homes with Teslas, right? Like, that's an additional feature which I love. you kind of are giving a whole package for people who want to work, who want to have a good vacation, et cetera, et cetera. Is that the initial idea or did it change over time?

Yeah, I can explain the idea pretty simply and the thesis behind it. And it's really that vacation rentals, short-term rentals are a growing percentage of lodging. So now they're anywhere between 15% and 19% of lodging, depending on which study you read, which is hundreds of billions of dollars of transaction volume, millions of users, like pretty massive amounts of capital and money flowing around, and obviously supporting massive public market caps like Airbnb, which is an obviously like incredible company. And I also think Brian is like super badass. My thesis was that if you look at the rest of hospitality and lodging, you have all these known brands, right? Four Seasons, Ritz-Carlton, Marriott, that users gravitate towards because they know that there's going to be consistency and quality and all of these other things. And that's something that obviously, like, a marketplace typically lacks, right? It's discoverability versus, like, knowing what you're going to get. And so my idea with Wander was effectively, what if we could create a consistent and quality experience across a portfolio of all the most incredible locations and create a strong brand and distribution around that and effectively create this entirely new experience where it was like the hotelification of vacation rentals. And so everything that we do is in pursuit of that big idea, and everything that we do in that vein is also in pursuit of helping our users find their happy place. Right? This idea of, you know, making it so that you can go on this incredible adventure and stay at this incredible home that, like, you know, in this place that you didn't even know exists and have memories with your loved ones and have happiness and joy and all those different pieces. So that's the, that's the big theme behind Wander. And in terms of scale, it's really just like adding as many locations across the US and then, you know, starting in 2024, like across the globe and basically building this like really incredible network of places for people to stay. It's this idea of like the infrastructure to experience the world is like what I want it to turn into. So yeah, that's the company.

And how are you navigating the heavy lifting? Because buying a property, redesigning it or rebuilding it or even aligning it to your values and your standards.

Yeah.

the ones that you promise to the customers, it's a lot of work. Totally. So how are you navigating that with the team? And what are you like, you know, what decisions are you making in those, in buying these homes and making them quality?

Yeah, so Wander has 2 supply-side strategies. So one is ownership, and then the other is when we take control of the asset on behalf of the property owner. Basically like operating the property to our standard, very similar to how a hotel does it, right? These hotels now are entirely asset light. They own very little real estate and they basically operate it to their standard. And another easy way to think about it is like a franchise. And so bringing a home to standard obviously costs money. We're fortunate that in our model, that's something that the owners of the properties pay And yeah, it's basically around operationalizing the logistics. Like, you know, every home is also, you know, unique, but of course, like a lot of things are very similar. And so as you scale and do more and more, the operations become like more unified and less complex and obviously more organized. And so it is certainly a lot of work, but when you actually look at like the value of each location in a Wander model, because we obviously focus on homes that are really special, like it makes a lot of sense. They're all profitable because the costs are offloaded to the owner. They're all profitable within year 1.

And I think I saw this on Wander's website. You also encourage people to buy properties and you help them make a living, right? Like as a passive income, if I'm not wrong.

Yeah. So if someone's interested in basically like purchasing a Wander-type property, like we can surface opportunities to them. And, you know, I wouldn't say in the current rate environment that I would recommend it as like a, like a way to like get rich quick. Like that's not the vibe, but it certainly is an incredible way to invest in real estate, specifically a potential second home. And have the property cover all expenses, if not throw off some free cash flow as well. So

that's very interesting to me because we recently bought a home and my God, it's such a messy thing. It's not straightforward.

It's a full-time job. Absolutely.

Yeah, it's so time-consuming, it's so demanding. But I think I love what you're doing and I would love to see that program expanded to, uh, just home buyers or like second home buyers.

Totally.

Because I think it'll make a massive impact because the— it's like, it's like iPhone when you live in a BlackBerry world.

Yeah, it's, it's really, um, yeah, candidly, like, we, um, yeah, we're very lucky that our users love our products so much. Like our customer satisfaction is like 93%, which, you know, for like context, birthdays in America are 89%. So it's like, people love this product. And that's a real, that's a real like score, by the way. That's not like, that's a, how would you rate your experience on a scale of 1 to 10? Like if it's raining, someone will give us an 8. Like, so it's sort of like, yeah. It's certainly a lot of work, but it's incredibly high moat as well. And I think that that's something that a lot of founders forgot and a lot of VCs certainly forgot, is that if you can build a company to the moon in a year, it's probably pretty low moat. And I think we saw a lot of that, like FTX being a great example. Obviously there was some deep fraud committed there as well. But it's like, you know, that went from like zero to billion dollars plus in revenue in like a year and then it imploded. Yeah. Like, you know, so it's like building something that's really valuable takes time. You're looking for like good compounding growth. You're looking for something that's high moat. And if you think about Wander's moat, it's like we control the properties, we control the distribution, we control the brand. Like it's a platform. It's not just like a marketplace.

It's like a real— Yeah.

That's why Yeah, it's a real platform.

That's one thing I love about Wander is that you have control. Like, it's not like you're overpromising and underdelivering. You promise and you keep that promise, right?

And the cool thing is, is like how you're taken care of as well. Like, if you reach out to Airbnb support, they can't— again, Airbnb being like a different example, but like, the point is, is that people can't solve the problems in the way that we can. Like, we are deeply, tightly integrated. Like, I'm personally looking at every piece of customer feedback and input. Like, we are very much dedicated to building a hell of a product, and it's certainly going to be very difficult and time consuming. But we have this one thing that so few others do, which is people love it. And it's like, if you build something that people love and people want, like, then obviously scaling it is difficult. But that's like, You know, chapter 1 is like, build this classic YC statement, right? Build something people want.

Yeah.

So

I love it. That's

why it looks good.

I appreciate it.

I love it. It really means the world to me. So

yeah, I love the vibe when you guys launched in 2021. I think Kyle Tibbetts, you know, I follow him on Twitter. He's a machine.

Kyle is the best CMO I've ever worked with.

Yeah, he's a machine.

If anyone tries to poach him, by the way, from this, like, I will, like, be very angry. Like, that's a hell of an endorsement. Kyle's obviously very, very, very invested in Wander. And also he views it the same way I do. Like, we've seen enough startups to know that Wander has the potential to be something really rare.

Yeah. And really big too. Not just rare. It's going to be very big. I'm bullish on it. I know we're a little over time. I want to have a couple of questions. What's next for Wander? What is the insane, ridiculous dream that you have for Wander that you haven't shared with anyone, not even with your team? That's like one of the things I had in my mind when I was actually going through Wander's website. Feel free to like, you know, shut it down. I think just the way, uh, rental, short rental industry sucks, you know, flighting— the flights suck, man. Like, it's so— it's one of the things I hate. The whole process is so messy. It's still, you know, 40 years backwards. You still have to like do a lot of paperwork and, you know, all the, all the shit. Like, if you lose a baggage, it's shit. I think Wander should make it complete package, meaning literally from your doorstep to Wander's doorstep. I would love to see that. That's, I think, the ridiculous dream I kind of manifest for you guys, but I would love to hear your take.

No, I mean, I love it, right? It's the idea for Wander again, like if you were to say like what's under Wander's scope, The big scope is, is the infrastructure to experience the world. Like, the product and what we're doing today is going to be just one small piece if we end up being a rare and important company of what Wander will be. And the same way that Amazon started by selling books, and then, you know, 20 years later, 30 years later, they're the company that's in front of us today. Yeah. That is what Wander is going to become. We are going to become a multi-pronged, multi-product company oriented around travel and quality and building the first customer-first travel company that exists with a focus on technology and ease. And we'll take ownership of the things that we need to own to ensure that that's true. So you're not, you're not far off. Now, obviously, there are an incredible amount of things that need to get solved between here and there, and it's going to take a lot of years. And I'll probably have very much like less hair when we get there, which I look forward to. I look forward to like, you know, if we're lucky enough to make it, looking back on this interview.

Yeah, we'll see you back. Yeah,

we'll try.

I'll be there for sure. Yeah.

And yeah, I look forward to being bald and full of wrinkles at like whatever, like 20, like 35 or something. But yeah, we'll see. We'll see what happens. But there's a lot of exciting things. I mean, you're going to start to see the early signs of that, right? Like we just rolled out chat in app and on web. We'll be integrating like these large language models into that and then integrating that into the APIs of our own and other companies. So soon you'll be able to ask like, hey, I want to book a flight for these people and stay at this house for these dates and book these activities, and it'll all automatically be done for you. And obviously, like, that sounds so ridiculous, but like, that future is here where everyone can have their own personal travel agent.

Yeah.

Like, there's a lot of really cool things that are in the works. Obviously, we have to build a lot of systems for scale as well. We've recently gone from, you know, doing like, you know, 2, 3 homes a month to now we're doing 5, 6, 7 a month, 10 a month. And that is a remarkable amount of work. And so you have to build a lot of systems for that as well. So I'd say that 80% of our focus is on scale, 20% of our focus and like making everything work in that vein. And then the other 20% is like these like really radical features. And then if you fast forward into 2024, you'll be looking at international expansion and like that same story. And then from there, you're going to look at new verticals being added. I can't tell you exactly which ones they're going to be as it'd be likely to change. I'd have to give like a percentage that would be very low on like what I thought. But yeah, there's so much opportunity. Like no one is over the moon about their travel experience. And like, I think I'd love to solve that for them.

You have so much ground to cover. Let me tell you that, you know, I'm not a frequent traveler, but When I travel, I always have this regret. Why, why can't people make it super simple? You know, you went to—

Even using existing infrastructure. Like, I want my app to tell me, like, arrive to the airport at this time. Like, your car is for you outside. Like, and then it shows me, like, with an arrow, like, where do I go to my gate? Like, all these different pieces, all this again is super technologically difficult. So like all the skeptics who are listening, like, you are absolutely right. This is like years away. But it's, it's still cool to think about, obviously.

No, it's, it's solvable, right? It's, it's, it, I, it is something that you can solve for, right? And we went to SF in July to celebrate my, my little guy's birthday, first birth, uh, second birthday, and we, we boarded United. For whatever reason, flights canceled. We had to stay in Chicago. All this shit happened. They lost our bag. You know what, there is no way to call people of United and ask for the status. You have to wait for a couple of hours to just to—

Oh, I've been stuck in airports overnight many times. Like, it's delayed, delayed, delayed, delayed, and then like 3 in the morning it gets canceled. Yeah,

that's insane. So I would—

again, it's about manifesting. Yeah, I would manifest something.

Yeah, yeah, it's like customer-centric, service-minded leadership is what's lagging in these traditional old-school methods of running companies. Wandris has such an opportunity, I feel, to revolutionize or innovate really like, you know, air travel as well.

Yeah, we have, we have the opportunity to scale what we're currently doing, which we're fortunate that that has product-market fit, and obviously like we need to scale that. But then the cool thing is that you can imagine a few tabs getting added to the platform. You can imagine things like even like home sharing or even like a curated marketplace. You can imagine this AI concierge dealing with all of your travel. You can even imagine longer-term stays and wander urban, hopping from city to city, events and experiences. I mean, there's so much opportunity. And again, like, you know, this all— it's difficult to talk about the future without seeming like super naive and crazy. But, you know, at the end of the day, it's fun. And it's like, that's a big part of it.

That's what I love about building startups, right? Like, we imagine this grand, you know, grand vision.

And I think that that triggers— I think that triggers a lot of people. Like, I think that there are certain people who hope that you fail. because you thought so big. And like, it does— it is likely to fail. I think that's the one thing too that I would say is like, I am not ignorant to the fact that like failure is of course like incredibly likely. But

I think

the key is just to work hard and see how special it can be.

I feel honestly, this is what I believe in. Trying is important. Winning or failing, it's like you said, it's external constraints that will add to that outcome, right? Trying is something that we control completely end to end. You have a vision, you have a dream, try it. Just give it a shot. Forget about working it out.

And whoever's listening who needs to hear it, I am rooting for you. If you're chasing your dream, I personally am rooting for you. So

awesome. Yeah, man, that's amazing. John Andrew, this has been— I can go on and on. I don't know about you, but I have this weird energy on a Friday evening that's not transferable for fun or anything. I want to build something now. You kind of inspired me now. This has been amazing. So many lessons, so many incredible lessons. I love the frameworks. I kind of the problem-solving mechanisms, uh, the way you view startups start from zero, you know, it gets— it never gets easier. And I feel like you have this energy that's contagious. And like you said, the least we can do is to root for someone to win, right? Who has dreams, who have bigger visions, so bigger ambitions. So on that note, thanks, John.

It's been a total pleasure. You've done an incredible job. I'm so stoked for you. And yeah, thank you so much for having me. This has been truly a joy.

Awesome. I think I did my job. Thanks, folks. Thanks, guys, for listening. Appreciate your time and attention. We have awesome, awesome guests coming onto the pod. That's John Andrew, and I'm signing off, Sharath, from the Undefeated Underdogs podcast. Stay healthy, guys. Stay ambitious. Do your thing. Cheers.