Starting & Scaling Wander With John Andrew Entwistle | EM Group Chat #210

Welcome back to Everything Marketplaces, where we talk with founders and leaders on some of today's top marketplaces. So this is episode 210, which is a really great group chat we've had with John Andrew Amosil, who's the founder and CEO of Wonder. Wonder is a marketplace for luxury vacation rentals that offers hotel-level amenities and convenience. It's a breakout marketplace that's scaled over 1,000 locations. They've also raised over $100 million in capital from top investors like QED and Redpoint Ventures. So it's a really great chat with John Andrew. We went back to the founding story and first steps to starting Wonder, some of the early challenges, John Andrew walked us through how it's evolved and scaled. We did a deep dive into it as a leading marketplace for luxury vacation rentals today, how they're leveraging AI. We got to learn about their growth, what the fundraising journey has been like, and we also had a great group Q&A. I really enjoyed this conversation. You're going to find it a great watch to the end. So, John Andrew, I wonder— has been coming up in the community for a while now. You've been highly requested on Group Chat Cast, so it's great to have you join us here today. I want to start off by saying huge thanks for taking the time to do so in advance. We have a lot that we're going to dive into with your experience starting and scaling Wonder, but I thought it'd be great if you could start off by briefly sharing your background for those here that might not know you.

Yeah, for sure. And thank you so much for having me and the community you've put together. It's like, it's truly extraordinary. And honestly, if you're a marketplace founder or candidly any type of founder interested in these dynamics, I mean, I think it's like an absolute no-brainer. So thank you for creating this like jewel on the internet. Yeah, in terms of My background and story. I've been a founder for a very long time. I started my first little internet company when I was 13, 14, and haven't looked back since and was not focused on my homework. I always tend to joke my dad was a single dad and a lawyer, and I think I always just wanted to work like him and help the family out. And so he was on his computer and I figured I might as well go on mine. I started my first venture-backed company when I was 17 called Coder.com, which moves the development environment where a software engineer writes code to an organization's cloud infrastructure. That company did very well. We raised over $100 million. I think now totals is close to $200 million, powering well over a million software engineers at companies like Vanguard, Goldman Sachs, Palantir, Netflix. So I ran that company as CEO from ages 17 through 23. So not your typical college years experience, but it was a total blast. I got to work with incredible mentors and venture capitalists and the team. I was learning every single day from the people around me, which I think has instilled a constant learning motion for me as a leader. So I stepped down as CEO of that company in 2021. Company was growth stage and brought in a professional CEO. And, you know, I was 23 at the time and I'm like, what's next? And was fortunate that all of Coder's VCs were adamant about working together again, though I don't think they expected me to start a travel marketplace. So I told them the idea for Wander. I'd spent my high school years traveling all around the world building small internet companies and just something I'm super passionate about, the infrastructure and experience layer. And so started the company with really this vision to verticalize the industry, this idea that if you could own the software and the, and the quote unquote hardware, the physical experiences, the digital layer, that you'd be able to deliver something really differentiated. And then as we of course grew, there were a lot of components of the business that just ultimately don't scale. And I think that's, you know, one of the classic YC mantras, uh, is, you know, do things that don't scale. But then you ask the question of eventually you have to do things that scale because you're scaling, um, which, you know, makes for an interesting You know, chapter as a founder is that you're literally recreating your business like every 6 months. And so that's been the journey of Wander. Wander today, we're scaling very quickly. You've hit me in a very heavy growth month where we're going to, you know, 2x the number of locations on platform month over month this month. We've raised about $100 million to date, backed by QED, Redpoint, Starwood, bunch of really, really wonderful VCs. And yeah, very happy to be working away. 28 now, live here in San Francisco across the bridge in sunny Sausalito. And yeah, that's my story.

No, it's a really great background. I'm sure we could have an entire kind of group chat on your early learnings with iCoder as well.

Totally. Yeah, that was quite the phase being 17 and selling to Goldman Sachs. We have a bunch of big government customers. And so I like, learned to tie a tie for the first time, you know, ahead of one of those meetings. And it's just, it was that kind of fast-paced life.

Certainly. And then we're gonna get into, you know, Wonder, but I did wanna go back to the very beginning, you know, so what were the first steps that you took to start Wonder at the time?

Yeah, it was really interesting. So Coder was obviously enterprise developer tools. So, you know, a very, very like B2B different type of business. And, you know, there I was at, you know, 23 at the time, deciding what I wanted to do next. And I had had the idea for Wander and was fortunate that all of my investors had basically said that they would fund any idea that I would come up with. And some had given specific terms to like, you know, different ideas, AI CRMs and, you know, otherwise. But I didn't want to build an AI CRM. I really wanted to build Wander. And so it really started with sort of like quick back of napkin math in terms of, you know, how many units would we need to get to? What would it need to look like? And very quickly it turned into what I would describe as like a postmortem, where effectively I wrote down, you know, my plan to scale and all the different reasons that the company was going to die, really trying to kill it on paper as often as I could. And then thinking through what the solutions would be. It reached the point where it was probably this like 80-page document that ultimately, um, I, I, I just couldn't kill it on paper and everything else had to be tested in, in reality. And I also knew that it was a company that I wanted to spend the rest of my life working on, something that was like truly, truly interesting. And so that, that was the first phase of starting Wander was an idea that just infected me, uh, and then a very long postmortem on all the reasons it would die and, and trying to ensure that There were answers to it before it actually came to reality.

That's really cool to hear. And, you know, as marketplaces, you know, we all face the, you know, chicken or the egg or the kind of cold start problem when getting started, right? So, you know, how did you solve for this with Wonder and what were some of those early challenges that you faced?

The first question that I always worked from is, you know, obviously we talk about like product market fit, but before that you have idea market fit. And I wanted to validate like how strong was the idea market fit for the end guest and customer. And so my solution was exceptionally capital intensive. I would not recommend it. But it was literally to go and buy the first few locations. I figured that if I could, you know, have control of that inventory, control the guest experience, control the digital layer, I wouldn't have to worry about integration scalability. I wouldn't have to worry about any third parties. I could just purely validate, was there idea market fit? And then would we be able to deliver a high, high NPS experience? So pretty much the definition of do things that don't scale. And that's exactly, that's exactly what we did. So the first version of the Wander app, we would slide the property sideways in a carousel. There were just like 2 or 3 locations. They would, you know, scroll in the loop and we announced it. And that was the number one customer complaint was like, why do you only have 3 locations? Meanwhile, the people who got access to the platform thought it was like the greatest thing since sliced bread. And it was those proof points that then unlocked The next phases of fundraising, which is sort of how it works in venture capital, is very much peeling back layers of the problem and saying and showing progress that, hey, like we have idea market fit, we have early economics, you know, here's our plan to scale, here's what it's going to look like. And so that's how we solved the Cold Star problem, which is literally controlling the inventory. I think there's a lot more managed marketplaces nowadays. I know that's starting to turn into Sort of a bigger and bigger idea. But again, exceptionally capital intensive, only something that you can unlock with having an existing relationship with investors who, you know, have faith in you as a proven founder. You know, if I was forced to start Wander again without access to that capital, I would probably go up a level into the next supply type, which would've been, you know, operating the properties. So more of the property management layer. Is how I would've gone into that, which of course is where Wander evolved to after ownership and then after operating, going into more what looks like an Airbnb. So again, various levels of the cold start problem. I think the cold start problem candidly kind of shows itself over and over as you grow your marketplace.

I'm glad you mentioned as far as, you know, taking like the more kind of managed approach, you know, early on that looked like, you know, actually kind of owning the homes and then kind of, you know, changing from there or evolving, I guess. But could you maybe share a little bit more about, you know, some of the considerations that kind of go into that as far as like on that supply strategy and that management, then how that also kind of like impacts, you know, your ability to kind of, I would say, you know, grow supply?

Yeah, totally. I mean, it is as radically complex and hard as you would imagine and very, very slow to scale. But what it does is it gives you this exceptionally intimate understanding of your customer, which ultimately unlocks a complete understanding of the industry, which as a founder strategically has enabled us to kind of, I think, navigate consistently to Like very high-scale paths. And so as an example of this, when we first owned the homes, like I can tell you every inefficiency in the, like, you know, home buying space. I can tell you everything about like analyzing vacation rentals and what that looks like. I can tell you everything about the insurance layer and then into the management, everything about vendor operations, payouts, margin, technology stack, you know, anything and everything related to it. And then of course, when you own the distribution channel as well, You know, can talk through what it means to build that platform and brand the backend infrastructure. And so what I think it has led to for Wander and sort of like the real benefit is that Wander as a company understands the vacation rental market end to end, both as like a vendor and also literally being our own customer. And that means that we can launch into any vertical, any marketplace, with an intimate understanding of the problem, that just means that we can sort of hit idea market and product market fit very quickly. Then as a founder, you need to choose what you do. And for us, we've decided that like where we're very strong is on the guest experience and on the distribution. So we really do want to just be at that marketplace layer in terms of people finding and booking incredible, incredible homes. As opposed to some of the other opportunities and more operational sides.

We did kind of touch on the supply side some, right? And that kind of strategy around there. But if we jump over to like to the demand side and that customer experience, you know, can you walk us through what it's like, you know, today on Wonder?

It's very interesting and things have changed rather radically. I'm sure you all are experiencing like this as well. When we first launched the product, it was very much just like, Hype, brand marketing, create accounts, and then like lifecycle. And then as you grow, you switch into sort of understanding your like per transaction unit economics. And at Wander, we're very fortunate to have an exceptionally high AOV. We have about a $5,000 AOV. And our take rate is about 20 to 30%, depending on the transaction. So we have a lot of room to play with, but as you would expect, the marketing costs to drive that kind of transaction can be high if unoptimized. And so, you know, from that perspective, we shifted from sort of platform and brand marketing into like, could we create a repeatable base through performance? And then as we scaled supply, we saw our CAC drop really dramatically, you know, on the scale of, you know, those initial paid bookings would cost $1,000. So, you know, as far as anyone would be concerned, that's like instant payback and like good, and you'll get them on the next one. But for me, like, I believe in like profitability on a per transaction basis as early as possible as a company. And I think for this month, it's like $200 to $300, something like that on the first transaction. So not even counting the full lifecycle of that customer, which our LTVs are, you know, in the hundreds of thousands of dollars with repeat guests. And so, you know, as a company, it's very interesting. It's like, You sort of start with brand and excitement for your early adopters. Then you go into scalability, more specific channels, performance marketing. And then once you reach a certain scale, you go back to brand and platform marketing because, you know, you're able to direct the traffic yourself into the specific types of supply. So that's been our journey and it took us a long time to reach this. Again, I'd say we hit it in like January of this year where we could switch back to more brand and platform marketing. And the marketplace itself, like the wander.com marketplace, hit profitability in January. So it took a very long time. It took, you know, 4 or 5 years. But, and in that, the last thing I noticed in that process, you have to be willing to switch your KPI from growth to profitability and then understand what drives profitable growth after. So for Wander, it was trimming back on performance spend, increasing the supply count, and hitting this very, very profitable transaction layer where then you just scale what's driving that, which is supply for us. So we are a supply-driven marketplace. And then the final, final thing I would note, which again, like I can talk to any of these topics for hours, is like you have to have a frictionless user experience. Like you really do need to make sure that your technology and user journey are not anchoring you because marketplaces are like, they're like a Formula 1 engine where like if there's one component that's off, the whole thing's gonna explode versus like when it's all working perfectly, you know, you can go 200 miles an hour. So that would be the other thing, which is much easier said than done. Like I can't emphasize the importance of user testing. more. And I don't just mean like hopping on with your users. Like, I mean, like the programmatic forms of user testing are very, very, very good. There's nothing like someone using your platform and then, you know, complaining on it in like a TikTok-like format that motivates you and you and the team to address the issues.

Certainly. You mentioned lots of topics that we're probably going to get into during the group Q&A as well. But, you know, I want to transition into talking about, you know, how you're leveraging AI because you've been sharing on social about, about it, you know, with your recent growth and how it's been an unlock. So, you know, so like as a starting point, you know, how have you approached leveraging AI? And then we can get into how you're, you know, some examples of how you're doing so in more detail.

I think that there's 2 forms. There's internal automation and then obviously like for your own marketplace. From an internal perspective, Wander is a little over 100 employees. And I noticed that everyone was effectively acting as middleware between applications and that that was grossly inefficient. The knowledge layer was completely dispersed. And so I actually worked with some old buddies of mine from, from Coder to stand up this product called Adapt that basically interconnects a company's entire, entire knowledge base tooling, basically merging remote compute environments and agent environments, and obviously then deployed it on Wander. And so that's how we run our business is that there's this, you know, software called Adapt that you can go ahead and ask any question to, you can interact with. And it's now like publicly available as well. So it's not like, you know, some secret thing we see. We, I think we all see like Ramp and others posting about their internal tools. I did not want that to be like isolated for us. And so, yeah, that's very interesting because like if I see a problem, I can just tell it to go and fix it. If there's questions, it can go and answer it. It has access to all of our internal systems, customer records. So it can do anything across the company, which sounds a little bit trippy from like an AGI perspective. But it's here. And so from an internal perspective, like the way you build companies has shifted forever. You no longer need humans to act as software. You no longer need, you know, massively bloated headcounts. You can be radically operationally efficient, which is really interesting. And then also a little bit scary as an operator and just in terms of how fast things are evolving and always asking the question of like, am I doing the right things and thinking about it the right way? From a core marketplace perspective, again, it replaces all the humans as software. So I think all of us have probably seen there are parts of the business that were impossible to be automated, whether it was, you know, purchasing or permitting or curation or who knows what dynamics required, you know, headcount and sort of needed to bake that into your economics and were obviously hard to scale. We've replaced all of that with agents, everything from property page descriptions, curation, You know, owner communication and then, you know, beyond. And of course, you know, from an engineering and otherwise, like it's all deeply automated. But, you know, I would say that breaking it into those 2 categories is important. And yeah, Adapt has turned into our centralized knowledge tooling interconnected agent. And then, yeah, in terms of the customer, there are lots of different toolkits you can use to build out those internal agents.

That's really cool to hear. I guess if we could go a little bit deeper on some examples, you know, maybe from like an operational kind of efficiency, can you share a little bit more about how you're leveraging it specifically there?

So like, as an example, now anyone inside the company can understand the entire codebase of the product. So for example, one of our folks on the finance team, one of our controllers, Lauren, is now acting as basically an end-to-end product manager and builder where she can understand the payment services, how they all flow to the end customer, using that, go ahead and create a spec, Adapt can pull our internal design kit and spin up a development environment, write the actual software and push it for code review, all from, you know, someone who's a CPA by default. And then of course, anything from data analysis to like, you know, is this user going to churn, anomaly detection, literally anything that your company is doing behind a computer, it can like help sort of remove friction, which has been very, very powerful.

Yeah, that definitely sounds very powerful. So we'll have to check it out in a little bit more detail with some examples maybe sometime. So, and you mentioned that earlier as far as growth and expansion, but how have you approached growth and expansion kind of now at the later stages for Wonder?

Yeah, it's very interesting. So we recently welcomed, now I think this is less so specific to marketplaces and more so specific to the founders behind it. You know, I've been, I've been working on Wander for the last 4 years. We're about to turn 5. And I think by like any measure, we've had like really good growth under my leadership. But I felt like it was very important to have like a change at the highest level inside of the company. And so we recently hired a president and COO who was an ex-founder, had scaled his business, had a sort of operating framework lens and candidly like style Very different to mine. Like, I'm very, what's the word? Maybe like a little bit too like gentle, so to speak. And, you know, he operates in a very different way. When he joined the company, you know, we had gone from, you know, whatever, like very good month over month growth, call it like 30% month over month growth. And he came in, he ripped everything apart in the first 2 weeks. And like I said, we're now going to double month over month. And it was very obvious to me that the company had a ton of potential energy that ultimately having been working on it and having my blinders on it for so long, even though it was growing exceptionally fast by any type of startup measure, it had so much more there that an outsider who's now an insider could bring to the table. And so, you know, with that, I would say that like, If you feel that your business is like a good business, but like it's starting to kind of stagnate, it may be time to like evaluate almost bringing in like a quote unquote co-founder level person, like someone who has the experience and viewpoint and can really shake things up. Of course, that hire may work and may not, it may be like a disastrous hire. So, you know, time will of course tell from that perspective. But, um, you know, that's, that's, that's what I would say is like probably the most useful thing in terms of answering the question, like how I think about scale is that like we were growing very quickly, but it just felt like something was off. And like that one force multiplying hire placed at the highest point in the company besides myself really, really did unlock it. You know, I think now just to talk in terms of like total size, like we're, we're going after the entire, entire TAM. I think like, you know, these other booking platforms have about 7 million total units. You know, we're pacing now to add about 10,000 units-ish this month. You know, I think that, you know, on the order of magnitude of 50,000 units a month is certainly very like possible for us across both like our WanderOS and wander.com products. And so that's really what we're going after. Like we're chasing the mission statement of being like The the infrastructure layer for travel, and of course that's going to be really hard and suck and take a lot of time. And I'm sure it'll feel like the company's going to die multiple more times, which of course it has felt in this journey. I also want to make that very clear for the founders here that like Wander may look very shiny, but it has certainly felt like it was going to fail. Multiple times. And that was actually really great advice that I got a long time ago when I was starting Coder. I pitched to this serial entrepreneur. I was 17, pimply, like, you know, just starting my life. And the first question he asked me was, are you sure that you want this life? Which was a very profound question. And I said, yes. You know, I'd been building companies since I was 13. Like I had decided that this was my life path. The next thing he told me is that there would be 3 times, at least 3 times, if the company was going to be successful, that it would feel like the company was going to fail, that you would be certain it was going to fail. And that created a ton of comfort for me, creating Coder, creating Wander, because now I like, I count them on my hand. I'm like, okay, like this is number 2, like cool, like we'll keep going. I think now I've passed 3 with Wander. So like now I'm starting to question like, okay, how many are, are there? Like, is this actually comforting? But I think that's very good for a founder to just feel a little bit of comfort in is that like it is exceptionally hard. It is going to feel like it's going to fail multiple times. And I think that like Paul Graham advice of just like be a cockroach and Like, survive is very valuable.

Definitely what we need here. See, these are the type of conversations as founders.

Yeah, it's miserable for sure.

Cool. So I want to transition to talking about the topic of fundraising right before we get to the group Q&A, because, you know, you've raised, I believe, over $100 million in capital from some top investors like QED and, you know, Redpoint Ventures. You know, so what has the fundraising journey been like and what are some of your key fundraising learnings?

It's crazy, the things I've— I think Coder has raised now $200 million, most recently a $90 million Series C. Wander has raised over $100 million and then Adapt has raised like $10-ish for their seed. So certainly very familiar with the world of venture capital. You know, I do want to note that like raising venture capital is not actually like a good shiny thing. Which I realize is like very much the opposite of what all these gurus say. But that's also because I am not a guru. I think that like your goal should be to raise as little money as you need to build your company. And like those constraints are really, really important. You also need to have like product market fit with the investors. Like they do need to believe that you're chasing a $100 billion type outcome. Otherwise, it's, you know, the return dynamics and mechanics don't necessarily work. So I guess I would say this, raising venture capital is not success in any way, shape, or form. Like when you guys hear those numbers, like to me, they're non-impressive in the sense of like, they don't actually matter. Like happy customers matter, positive unit economics matter, like flywheels and network effects, those matter. Like capital is just a tool to achieve them. So I think disconnecting that is super, super important. And then I would say the second thing is, you know, making sure that you're only raising what you need to get to that next stage, which may or may not be expensive. I'd also say the cost of achieving growth has dramatically reduced, like on the order of 10x reduction versus when I was first starting to build, you know, Wander. I mean, you know, to give you an idea, we were building The backend infrastructure, the application, like just all these different pieces, Airbnb level complexity that required an engineering team. Um, now, you know, you're, you're looking at being 10x more productive on a per engineer basis. Like you just do not need as much capital. If I was to build Wander again from scratch, my guess is it would require probably a third as much capital as we have raised. Um, just because of the shifts that have happened with AI. And so I think that's also important to recognize. Yeah, in terms of the process, it's really as simple as like defining your vision and TAM and ultimately starting those conversations with VCs. You'll understand if you have like product market fit in terms of raising capital, like relatively quickly. And then I, again, I'd say like definitely disconnect that raising venture capital means success. And then I'd also say too, if your competitors have raised venture capital, Like, again, that is completely disconnected from success. In fact, a lot of times it can kill those types of companies because they'll go ahead and spend tens of millions of dollars on performance marketing that gets eviscerated and never have actually solved like the core underlying pieces. So yeah, I guess that would be the piece, but we could probably spend like 4 hours on like the tactical, like how do I raise my seed round? How do I raise my pre-seed round? The final thing that I'll note actually on this topic is that how fundraising works changes every 6 months. Like how you raise a pre-seed today, you know, 2026, it's very different than 2021. And so like you'll find a lot of very outdated information and advice. And I would actually say that like the fact that I have gone into market or like had founder friends that were in market every you know, 6 months is very, very useful. So if you are going to fundraise, my advice is to take advice from someone who just fundraised, not someone who fundraised in 1990, because they're going to give you terrible, terrible advice. So someone who just raised a seed round will give you better advice than I would give you, um, you know, however many years since it's been.

So lots of great points. You got some awesome head nods with that also. So we're gonna get into the group Q&A, but right before we do, what would be your top tips for a founder starting a marketplace today?

I think I'd actually probably start with like the advice that I got, which is like, are you sure? Like, are you sure that it's what you want in life and what you want to do? Because you're committing to a chapter. You're committing, when you start a company, you're committing to a 10-year chapter in life. And it is just that. It is a commitment and a very, very meaningful chapter. And one that ultimately you won't find out if you failed at or not until the end, definitionally. And so, you know, I think that that's probably the first piece. I'd say the second piece is to kind of redraw how you build and how you operate with how technology has shifted in the last 6 months. I'd also give this advice to anyone who has an at-scale company. I have been working to completely rebuild Wander in the lens or through the lens of If I started the company yesterday, what would it look like? And I think that that's a really important exercise. I see a lot of, you know, folks on Twitter going through that same existential crisis as an operator, literally recreating their business. And it's like stressful and painful, but I think it's very, very important. And then I'd say to just focus on your economics, focus on your product. You know, don't force growth through things like performance and unnatural actions. Just force growth to the point that you get the information that you need. And once you have the information you need, focus on fixing those issues and then continuing. So I'd probably end it there in terms of like listing things out, 'cause again, I could go for a while, but I'd say like the most important thing is to like redraw your framing on the art of possible with this technological shift. and be efficient and focus on like the core sort of laws of physics when it comes to building a business, which is like basic unit economics and financials.

Those are really great, great tips. So, well, cool. So we're going to get to the group Q&A, but I wanted to help ask a question that was added in advance to kick things off here. And it was around the, you know, concierge. So, you know, what led to initially kind of launching this? And, you know, are there any initial learnings, you know, from this that maybe led to even like, you know, different product or kind of offerings as a result?

So the Wander Concierge, Launched very much in the theme of all things Wander when we first launched, which was do things that don't scale and go way over the top. So like to, to again articulate this, when Wander first launched, it was 3 properties, fully owned, a full digital experience. We had built out our own smart home tech that interconnected the app to the actual home so you could turn on and off the lights. There was a Tesla at every home that was also connected through the app. I like reached out to some director at Tesla for like a direct integration. Like we went crazy and it would, but it was all MVP, right? So it wouldn't scale to 1,000 properties or 10,000 properties. It would only scale to 3, which is why we were able to ship it so quickly. Concierge was no different. So there's a basic number of like human beings that you need to have 24/7 concierge. I think the answer is something like 12 if you take into account like time zones and weekends. And we only had like 3 guests at any given point in time. So I was like, hey, like let's deliver that true 6-star experience and have them literally do anything they need. And there are some stories from the early days that are just like absolutely beautiful. Like a guest forgot their suitcase and the concierge team like had a courier pick up their suitcase and like bring it to the property. Or like someone's favorite board game was missing and like we found it through some like vendor in like Japan. It was like the, like truly the art of the possible. Like very much the definition of the book, like unreasonable hospitality. And through that, the purpose was to learn, right? Like I wanted to learn like what was necessary, what wasn't, like deliver this 100 MPS experience and then like draw it back as we like started to scale. And of course, over time, like the wander concierge eroded into what feels a little bit more like a high-end customer support function as opposed to this like digital, you know, assistant that takes care of absolutely everything. And then, you know, as you would expect in the age of AI, you can start to walk it back towards something that does scale. You can start to think about, you know, does everyone have this like agentic travel agent in their pocket and what does that look like and everything else. Though interestingly, and this is, you know, probably the opportunity for, you know, another startup, though to be clear, like Wander will certainly, you know, certainly pursue Is that now at our scale, like, you know, spinning up persistent agents per customer with this like living travel agent is hard to scale still technologically. Now it's like technologically possible, but very hard to scale still. And so we're still in the form of like automating as much of our support as possible while still delivering that high NPS experience. But it's very clear what's going to end up happening next is that you can bolt on services to your marketplace using these AI agents that ultimately feel like magic and like very, very luxurious. And I think that that is what is clearly going to be the monetization path for marketplaces is going to end up being like bolted on services that are powered by AI agents that operate on top of the infrastructure of your underlying storefront slash marketplace.

So I'm going to help ask another question that was added, and it was around repeat bookings. And they were asking, you know, are there any specific levers that have worked well for, you know, increasing repeat bookings?

Wander has a remarkably high repeat rate. And we've had some customers who've spent, you know, over $200,000 on the platform over the last, you know, 4 years. So they basically just book all their travel at Wanders. That's completely driven by NPS. You know, our NPS, I think for last month was like high 80s. It's very, very, very high. You know, I'd say that there are other things you can do like loyalty and lifecycle marketing, but realistically, if you crush on MPS, you're going to see repeat behavior, word of mouth, et cetera. So that would be my primary advice. I think if you offer a marketplace that does not have the potential to be that high MPS, like for example, Like Instacart is like, it's very hard to say, well, Instacart's actually a little different because like getting your groceries magically delivered is very high NPS. I'm sure there's like some example where it's like a little bit more challenging to hit that high of a net promoter score. Yeah, I would say to like focus on like loyalty, repeat benefits, et cetera. You also have to realize like what the transaction frequency of your marketplace is. So like travel. You know, people will book, you know, our customer will book like 2 trips, 3 trips a year. And so every one of those trips is an opportunity for us to like convince them and capture them, which also goes into supply type. I would put for us is like, you know, we would have a 100% repeat booking rate, 100% capture of our users' travel if we had every type of inventory that someone wants to go and book. Like we don't have locations in Europe yet, as an example, we lose those bookings yet they would totally love to go and book on Wander. So I'd say that's the other thing too, is to understand like inside of your marketplace category, is there inventory you're missing to increase the total number of like repeat purchases? But yeah, I would say focus on the NPS is the first and then probably focus on your like supply coverage is the second. And then basic like lifecycle marketing to stay top of mind and like build that habit, so to speak. Aligning incentives is also exceptionally powerful. That's something that we're going through the process of is I'm about to make a pretty major change, which I don't want to announce here, that will like forever align the incentives of Wander and the end customer in terms of why you should be booking through Wander no matter what. And so if you can figure out that, that's also very powerful and challenging for competitors. So that would be what I would say would be like my order of operations. And then of course there's like infinitely more tactical things, but that at a high level.

That's going to be really helpful. I'm glad you mentioned the importance of aligning incentives. So that's something we're often discussing in the community as well. And you did mention the NPS or having a very high NPS quite a few times. And, you know, so what are like the key ingredients you think that go into that?

I often think about like brand as a, like the promise, brand is a promise that you make to your customer. NPS is the measure of how well you delivered on that promise. So, you know, for Wander, our brand is like, you're going to have a great trip. Our NPS is a measure of like, did we do it? And so, you know, in terms of like how you execute on that, that's obviously specific to everyone's independent business, but I think that is the mental framework that I would have in terms of driving a high NPS. Like, you know, for example, if your brand promise is like the cheapest potato chips in the world, if you deliver the cheapest potato chips in the world, you're probably gonna have 100 NPS for your users. So that's how I would think about it.

Hey, Jeff, saw you raise your hand. Do you want to jump on here?

Johnny, thanks for coming. A million questions for you, but one I did want to call out because I think it would be helpful for everybody is I'm curious, you know, you talked about if you were going to start Wander again now, you'd probably need about a third of the amount of capital to get going and get up to speed and that you've pivoted a few times. I'm curious how you think about defensibility of what you're building in general, especially in the age of AI, especially when costs to build, replicate, and so forth are dropping so significantly, even in terms of like products and features that you, that you're focusing on and offering, like, you know, AI search and things like that. Like those are becoming easier for other people to recreate. So how do you think about defensibility of what you're building? And if follow-up is, you know, if you do talk about speed to market, like how does venture capital play into that for you as a thought process? I mean, Obviously you go down a different road when you raise venture capital. A lot of it is about speed, but, you know, how do you balance something like that?

Yeah, I think that that's probably a question that a lot of founders are asking themselves is like, and now in the age of AI, like what is the replication cost of what I'm building? I think that for Wander specifically, it's about like you have to shift your strategy to a certain perspective, right? And I think most marketplaces should be doing this. You know, for Wander as an example, when I saw that the majority or the growing majority of travel search was populating through the LLMs, I thought that it was incredibly important for us to power the direct storefront and to capture like the long tail of inventory. And so that's why we launched the WanderOS product, where now Wander as a marketplace has 2 sides to the coin. One is the direct booking storefront for all of these, you know, vacation rentals and vacation rental managers. And then you also have the core marketplace. You also have to now think about like agents as a customer. And, you know, again, on the, on the point on aligning incentives, you have to think about your, your, your, uh, your monetization infrastructure. Like, you know, does the idea of a take rate on top of every transaction work when you're competing against the ability to find direct storefronts? Um, and to, and to go direct, um, which is obviously like, I think the biggest competition in the idea of a marketplace is, you know, that, that idea of direct. And of course, Wander's answer to that was to just power the direct infrastructure as we went. You know, in terms of like the technological side of things, I mean, at the end of the day, like I should always be able to outcompete anyone, even if they like spin up like Claude code. 'Cause it's like you with Claude code versus like me with, you know, that same infrastructure times 10. It's like, it's no competition in terms of who's going to deliver, you know, higher value, stability, growth. And to our customers, the pitch is very simple. It's like, you know, you partner with Wander and you never need to think about this again, as opposed to, if you're powering your own infrastructure, you're now dealing with the outage at 3 in the morning. So I think that that idea of like replication risk from your end customers is actually not as big as it would seem because like as a technologist, we all know like then you're dealing with your deployments and debugging and scalability and database issues. And like we're a long time from all of that being entirely automated. But I think for us, for the operators, it's incredibly powerful. So I think the larger threat really comes from like upstarts who adopt AI going against, you know, the theoretical incumbent that's not or slower to it. But yeah, so to answer the question, like, very succinctly, you have to reevaluate your entire business model now that, you know, every customer has their own AI agent. You have to align the incentives so that the agent, you, and the customer all want the same thing, which ultimately, if you're tagging on a markup for, you know, research or aggregation, you know, you're going to face, you know, business risk. And then from a technical perspective, if you and your engineering team aren't at the bleeding edge and, you know, there you leave the opportunity for some upstart to come and, and take the spot. That's very dangerous. But yeah, generally I would say that, you know, the, the, the model of marketplaces is gonna sh— the, the model of marketplaces just tagging on a service fee to a transaction with non-exclusive inventory is going to go away. That is like something I firmly believe.

That's a great question. I'm gonna help ask another one that was added. And it was around, you know, they were asking, when did you start to see the initial kind of flywheel kick in for Wonder? And then, you know, network effects started to kind of, you know, shape up.

I would say for us, it was when we passed about 3,000 locations is like when I actually started to see useful like effects, which I measured in terms of a reducing CAC, like a radically, radically reducing CAC. And you know, it's really interesting what that looks like. Just to articulate it is that like you start building your business, you force growth for like information. You kind of continue that until you like, you feel like you have, you know, all of your answers. And then at some point you need to pull back your marketing spend. Like you need to kind of see if the plane is in the air, so to speak. And then you'll get your answer. Like then you'll get your answer in terms of like, okay, like You know, what is our CAC and what does that look like on a per supply basis and everything else? I mean, literally for January, like I just pulled back all of our marketing spend. I was like, cool, like we've done it, we've built it. I'm gonna pull it all back. We're gonna see what happens. And the answer surprised all of us. It was like, sweet, like planes in the air. Like we didn't see like a reduction in terms of our GMV. Our CAC obviously like hit the floor. And then we got the answer, which is like, cool, like at this size, at this spend, at this repeat user behavior, like this is what everything looks like. Now to be clear, most marketplaces do that at a far, far larger scale than us. Like Airbnb did it like literally during COVID is when they finally found out how profitable their marketplace was without huge amounts of spend versus I was, you know, testing it much earlier. But like, have to is a great master through that lens as well. Like, you know, even though it can seem like we've raised a lot of capital, which we have, you know, Airbnb raised billions. And so like, depending on what the theme of the day is and what your metrics are and who you're talking to, that can shift in a very dramatic way when for us as a consumer marketplace, You know, there was a period in time where DoorDash, Airbnb, Uber were raising billions of dollars. Like that was the theme of venture capital. You know, I would say that that has shifted and now ultimately you have to kind of scrape your way to growth stage. Once you're a growth stage company, you know, call it $20 million plus net run rate, you know, the, you have plenty of capital available, but until that level, it can be, it can be challenging.

Like every kind of topic and question we could go super deep on. So Cool. So we'll try to get in on one last question if we can. Hey, Elisa, do you want to jump on here?

Hi, John. Thanks for being here. We're in the process of creating a new marketplace. We're bootstrapping it as a family. But I'm curious about your take because already we have a community of more than a million people that have been nurtured over the past 5 years, and they're all oriented to outdoor recreation gear. So we're creating a peer-to-peer marketplace to allow people to sell, buy and sell the used equipment. And now that we're far enough along in creating, we're using a minimally viable product on Sharetribe, and things are more expensive because we're not going to compete on price. We're really going to be more around The community and the education, because what we, what my daughter and her husband have realized in building out their social media community, education is a really big thing for these folks, learning what to buy and all of that. And so I'm very curious if you have any, if you've seen people build marketplaces more around the community piece versus like the price or being like the lowest price because now that we're into it, we're like, yeah, this is going to be more expensive than if somebody goes and posts on eBay or Poshmark or somewhere else. Um, yeah. And, and I feel like we're really in touch with the things that are most important for these folks, but again, we're not going to compete on like price.

I guess, and I'll abstract this to something that I think can be like broadly applicable to, to everybody. Um, Yeah, ultimately, like when you're thinking about your user, you have to kind of go down the lens of like what it is that they want. And every customer wants price. In fact, like, you know, like for example, like Jeff's business with like HostGPO, like that is the unlock, right? Is price like that. It's a huge, huge motivating factor. And even what you're hearing me talk about is that in the world of AI agents, they are going out On behalf of the user, you have swarms of these AI agents going out on behalf of the user and price shopping and doing that comparison and doing that evaluation. So that leaves you with kind of 2 choices as a marketplace. You can either have what I define as exclusive supply, meaning that like you can only buy this thing here and then you can charge whatever you want, right? From a take rate perspective or whatever else. But if you don't have exclusive supply, then you end up in this world that the other sort of OTAs, online travel agencies have, you know, look at Booking and Expedia when it comes to hotels, and it's just, you end up with price parity and a pre-negotiated take rate on the host side or on the supply side, but sort of this agreement between you and the supply that they're not going to go and list that inventory somewhere else for cheaper. So that's what I would say is that ultimately, like, if you are more expensive For the same exact inventory on another platform, you, you're just like putting yourself in a position of like a giant uphill battle for no reason. So like if I was in those shoes, I would, I would try and make sure that like my pricing was to the, to the consumer, to be clear, my pricing to the consumer was equal. Ideally, my inventory is exclusive to my platform. And if that cannot be the case, then negotiate a take rate with the host, with the supplier, while keeping the price parity requirement in play. And then you should be in pretty good shape. But yeah, I would not, if I would not have the same, like if a bag of potato chips at store A and store B are 30% different, but it's the same exact product, same brand, same label, then the AI agents are going to compare the two versus back in the day you could get away with like just convincing the human that that's like not the case, which to be clear, 60% of transactions, you'll still be able to do that. Like, you know, AI hasn't become that prolific yet. But it's coming like in the next 3 years, it'll be like definitionally the way that people shop.

Well, it's a great last question, a way to kind of wrap things up. So I know we're almost out of time, but, you know, huge thanks for taking the time to join us today for the, for the group chat, you know, sharing about all your awesome experience and learnings at building Wander and also helping to answer some of the questions that we had. So this is definitely a fun one. And I wanted to ask my usual kind of parting or closing question, which is if you could go right back before you started Wander, what would you tell yourself about marketplaces specifically?

My brain goes like instantly nerdy, which is like, what are the second-order butterfly effects of that conversation? Because ultimately, like, I am very happy with the position that we're that we're in. And I think that, you know, if I just skipped to this, ironically, Wander would fail. Like if I, if I told myself the exact version of Wander, the exact team, the exact people that the company would end up being in, but I didn't learn everything about the industry end to end on the way, then the company would fail. Like I wouldn't be able to run it. It would just be like, which I think is at the end of the day, going back to Jeff's question on like durability. I mean, that's hyper durable. Like no one understands this business like better than you all for your businesses and for us for Wander. And I think that is a competitive advantage. So yeah, I think it would be, I think that it's a very difficult question. Again, I was relatively methodical. I think one of the things that I believe in as a founder is this saying of fast forward inevitabilities, and I would just have done that even more. And what I mean by that and like how to apply that advice is that for each and every one of you, somewhere in your business, there's something that, you know, whether it's an employee that's not working out or a monetization structure that's incorrect, Or something that's just broken and you know that you're going to either have to kill it or grow it or make a change, fast forward that inevitability, even if it's like rather fuzzy. And I think that if I had lived that even just a little bit more aggressively, I probably would've saved myself, you know, an extra 2 years on this journey, you know, if I compounded it. So that would probably be the thing I'd say is that take that rule and Be even more aggressive.

Yeah, that's gonna be great parting advice for us here. So I feel like if we could all save that 2 to 3 years on the journey, that would be super helpful, right?

Amazing.

And then, you know, last but not least, time for a quick plug. Where can we all keep up with you and follow along at?

I mean, I hope that we all just become friends, right? So it's like, you know, I hope people just reach out to me. No, I'm on like Twitter and stuff, but again, I'm not a guru, so don't expect like, you know, anything too crazy there. I just like, I post Wander updates every now and then. That's pretty much it. But yeah, if anyone has a direct question, like, Ask ChatGPT for my email, it'll find it for you and just feel free to shoot me a ping. Like my goal in life is to be useful and good. So yeah, happy to help as much as I'm able.

Well, we appreciate you taking the time to join us here today and paying it forward to help out other founders. So of course that means a lot. So, and yeah, thanks again for joining and thanks everyone for the great questions.