Starting & Scaling Leland With John Koelliker | EM Group Chat #219

Welcome back to Everything Marketplaces, where we talk with founders and leaders from today's marketplaces. This is episode 219, which is a group chat that I just had with John Colliger, who is the co-founder and CEO of Leland. Leland is a leading career platform that helps individuals and teams build AI skills to achieve their career and educational goals. They've raised over $20 million in capital from top investors like Forerunner Ventures, FJ Labs, and as a disclaimer, we also back them through our fund Marketplace Capital. So this is a great chat with John. We went back to the founding story and first steps of starting Leland as a coaching marketplace. John walked us through how it's evolved and scaled. We did a deep dive into his leading career platform today, how they're leveraging AI. John shared lots of tips for founders, and we also had a great group Q&A. We did unfortunately run into some Zoom issues and had to make a few edits, but I know you'll enjoy this conversation and find it a great watch to the end. So John, you've of course been a community member since the very beginning when you were first starting Leland. So it's cool to fast forward to today and have you join us here for a group chat. We have a lot that we're going to dive into with your journey and Leland. But I thought it'd be great if you can start off by briefly sharing your background for those here that might not know you.

Good to be here. I'm John, CEO and co-founder of Leland. My background has been in tech in all sorts of different roles and companies, but there's a theme that's kind of emerged accidentally, which is marketplaces. So big, big fan of what you guys have built here. I interned at Uber in 2016, ended up joining LinkedIn and worked on their sales and talent marketplaces. And then joined a startup called Curated, which was another marketplace that connected people to experts who could help them shop for different products. And on the side, I'd been doing some experimentation in this like coaching content world and realized there was an opportunity to build a marketplace in this world and combine my side hustle, which was this kind of experimentation, and my day job, which was building marketplaces for a decade. And so started Leland about 5 years ago. And yeah, we've raised $20 million in Series A stage, growing quickly. We're happy to share a little bit more about what Leland is, but we're, we like to say we're building the home for ambition in the age of AI and, you know, help people with all sorts of different career and educational goals. And in 2026, AI has become everyone's career and educational goal. And so we spend a lot of time in AI as well. So that's a quick overview.

That's a great background and helpful overview. So I did want to go back to, you know, to the very beginning. So, you know, what was the founding story for Leland and what were the first steps that you took to start it?

I was actually a student. I was getting my MBA and was planning to spend the entire time while getting my MBA building a company. And so I was kind of juggling a few different things at the time. We actually had our second kid my second week of school. Started working on this startup. So I wouldn't recommend trying to do all of these things at the same time, but it was, I think it is wrapped up in our founding story for sure. We had people based in the Bay Area, in New York, in LA, and now we are, we all moved to Utah. So we're all based here now. But in the early days, we, you know, we had, I had this little side hustle helping people with applications to deferred MBA programs, which is a very small niche. And felt like the only way that I could really scale the impact of what we were building was through a marketplace model because of the dynamics of being able to drive prices down to serve a lot more types of people in different niches with different goals. And so built an MVP, took me a few months to find some engineers that I had worked with at LinkedIn. and convinced them to help me build on the side. This was kind of in the middle of COVID And so I think that was helpful to get people to have a side hustle because they weren't going into the office at the time. And we ended up launching and just did one category and that it was a very, very small niche. But we felt like that was the best way to kind of get supply and demand liquidity and everything and drive resonance in that category. And so we did that, raised a million-dollar pre-seed right when we launched, and then the marketplace grew pretty quickly. And so we ended up raising a $4 million seed round shortly after that. So that was kind of the first year of the company.

That's really cool to go back and hear the founding story again. And in the very beginning, marketplaces, as we all know, face the cold start problem. So how did you solve for that? And then what were some of those early challenges that you faced?

The best way that I think, whenever I talk to marketplace founders, I think a lot of marketplace founders think they need this really robust platform. Like the marketplace will only work when my product works as well as Airbnb, And I think the best way to do it is to just fake one side of the marketplace. And so for me, that in the early days, that was the supply side. We felt like, okay, if we can create, if we can drive demand, we can go to supply and find the right person. And so really my pre-Leland side hustle, I was doing coaching, I was selling content, and every time I didn't have capacity, I started to build a little network of people that I could refer clients to. And so I basically had built a marketplace and I was just the platform that passed people along. And so when we decided to go build the platform, it was really easy for us to feel confident that it was going to work because I was already doing it in a very inefficient way. And so I think that's my best advice is to fake one side of the marketplace and to try to drive revenue before you even build anything. And then Because the reality is like everything that we built was wrong anyways. And so it was nice to have some degree of confidence that it was going to work, but not overbuild it. And then, you know, we build it and it wasn't perfect. We could fix a few things here or there, but we had a lot of conviction that it was going to work at some point. We just needed to kind of get it off the ground. So I think that that's how we solved the cold start problem, which is focus on customers and kind of fake the supply side.

Yeah, no, it's definitely helpful tips. And I agree as far as their tendency to overbuild in the very beginning. So And, you know, Leland has, you know, evolved since you first launched. So can you walk us through, you know, how it's evolved and scaled before we kind of dive into it as a marketplace today?

Yeah, and it's still evolving. I feel like we're going to be evolving forever. I think so. We told everyone in the early days, hey, you're going to, you're going to have friends and family that are going to wonder what on earth you're doing building this like hyper-focused niche marketplace. And that's just going to be what we have to do to earn the right to go to the next category. And it's funny because investors will always They always want to know what's your big vision here? And they almost punish you for being really focused. But the reality is like every good marketplace is very focused in the early days and niches down because it's just hard to have liquidity in all the different geos or categories you have. So we just, we did MBA admissions as our first category. We felt like it had some unique dynamics that allowed us to get off the ground quickly, but also would allow us to scale. And expand really quickly. Within about 6 months, we had a lot of supply that wanted to offer services in other categories. And more importantly, we had customers wanting to buy from them in those other categories. And so in about maybe a year into the marketplace, we expanded into other career categories and we let people start to list in other places. And again, It's always been very, we hear a lot from supply, but it's always very demand driven. We always want our demand to be the ones that are telling us where to go because it's hard to go to supply and they're gonna tell you what they want, but it doesn't actually matter what they want. You have to figure out what the customer wants and then you can go to supply. And at the end of the day, supply really just wants to earn money. They want to provide for their families. And so if you can give them the path to doing that, they're willing to do different things, even if it's different from what they might think or want. And so that was kind of the model is we'd launch a category, find customers, go back to supply and we're, you know, again, we're sort of faking it as we go until we have the right supply and then we would go and blitz that and add a lot more supply. And we've done that across several different categories. So now Leland today is a marketplace where you can go to find an expert across hundreds, if not thousands of categories and subcategories. Everything kind of within the realm of professional career educational goals. So this could be applying to schools, applying to jobs, taking tests. And now, you know, obviously the, what I mentioned before, the biggest and most popular category, fastest growing we've ever had is learning AI. And AI is obviously such an interesting category because it cuts across everything, but it also is a category itself where people are just trying to learn how to build with agents. And so we, you know, we've launched a lot of different things to serve customers in that vein. And that's kind of pulled us into becoming more of a B2B marketplace because now we are, now we're serving customers that are actually enterprises that are trying to roll out AI at their companies. And so now we're helping businesses with their, I guess, professional goals, if you will. And so I would imagine that continues to grow and then you start to see the professionalization of supply. And so you have to enable businesses on the supply side, right? So I think The evolution continues to happen and there's additional things that we're going to do to build for customers that will, I guess, add to the evolution and make Lela more of a platform and kind of destination than just a transactional marketplace like it is today.

You mentioned lots of topics that we'll probably get into during the group Q&A because they come up. But one specifically was around the B2B offering. That's very common for, you know, consumer marketplaces to, you know, look at launching a B2B offering. So, you know, what are some kind of— well, I guess like first off, you know, what led to that? And then what are some of your learnings from, you know, launching B2B?

Being a consumer marketplace, you have to be really scrappy, right? It's like, well, how did you get your first customers? It's like, I'm doing everything. I'm posting on LinkedIn, I'm DMing people, I'm hunting Reddit. I'm like, I'm doing everything to get our first customers. And, you know, obviously the bar for a consumer to open their wallet is high and our customers spend a lot of money. They spend, you know, the average customer on Leland spends over $1,000. And so, you know, that speaks to kind of the desperation consumers feel, but turns out a lot of businesses had been funding what consumers were purchasing. We just didn't really know about it in the early days. And so I think once you start to see, oh wait, like this business, this person is expensing what they're buying, they're buying this AI coaching. We actually said there was a sales team at Anthropic that started to buy coaching individually for sales development and learning how to be better at selling from a couple of our experts. And it's like, okay, great. Well, we probably should just go straight to Anthropic and say, hey, what if we rolled out a program that was across your whole team? And that happens all the time. And so I think a lot of it is observing customer behavior that's already happening and then figuring out how do you kind of go have those conversations or even have your actual customers introduce you. We now work with a lot of universities You know, we work with USC or Northwestern, Harvard, Oxford, a bunch of them. And they all started because a bunch of students were using us and then they introduced us to their career centers who said, hey, you know, we have dozens of these students, if not hundreds already paying out of pocket, maybe that's a perk we could provide. So I think the best way to become a B2B marketplace is if you start as a consumer is to try to understand who is funding that consumer behavior. And do they all belong to a similar organization that also is aligned with their, their growth or their, you know, their investment? And so that's, that's how we've thought about it.

And, you know, I did want to transition to talking about AI because that's something that, you know, we're always discussing today. So, you know, as a starting point, can you share, you know, how you've approached this like big shift with AI at Leland and then maybe walk us through, you know, how the even like the product offering has changed and, you know, how you're leveraging it today?

For us, it's 2 different I guess themes there. One is what have we done internally? And then 2 is how have we kind of enabled that with our customers? And they're very related. I think, you know, as every founder has been kind of in this journey since ChatGPT launched, you're kind of always playing the game of when do we really invest? We're always experimenting, but when do we like back up the truck and change how we do things? And for us, that came early this year. I think similar to a lot of companies, there were, you know, some model improvements that just made it, Opus 4.6 just made it too powerful to ignore any longer. And maybe not ignore, ignore was the wrong word, really like back up the truck and go all in on it. Because before that, there was just a lot of like bullying you needed to do and a lot of like wasted time and effort. So we actually re-architected our codebase to be able to move faster. We built coding agents on top of it. We've you know, we've done a lot, but on the software engineering side, we've re-architected how the organization itself works and organized into very small teams so we can move faster and unblock people quicker. So there's like organizational structure, they're developing principles to help people understand, there's equipping people with tooling, and then there's the training and enablement. We started to see a lot of our employees ask for credits to go and buy coaching from our own expert pool. And we were, you know, we were like, of course, you're happy to do that. It's a perk. We provide that. But it started to happen enough to where we're like, okay, well, if if our, if our own company's getting value here, why, why don't we offer this to our customers? And we, we did, but it wasn't really, we weren't, we didn't have a concentrated go-to-market there. And so that, that kind of gets into the second part, which was how do we actually help our customers learn and develop these skills and start to build with AI? So we ended up developing the AI Builder Program, which is a live content-led program taught by experts that are in our community. helping people go from kind of wherever they're at in the AI journey to building automations and agents that kind of scale themselves and their teams. So that's a really like robust program and that's been our fastest growing product we've ever had. But then we also recruited thousands of amazing experts that have AI experience that can help with different roles and functions. And so that's been, you know, that, that's obviously been, been really transformational for us as a business, helping, being able to help people learn AI, and it's changing so fast that the joke is that you have to be unemployed in order to keep up with AI. And I think that people feel that, right? They're trying, they're experimenting all the time and trying to figure out what's real and what's not. And so us having a team and a network of thousands of experts helps us kind of stay up on that and be a place that people can trust. So there's, yeah, that's been a little bit of our story there.

Yeah, you got some, some head nods with the mention of trying to stay up to speed on things. So, you know, I did want to go a little bit deeper on some of the examples of how you're using within the product and kind of customer-facing. So there's a few specific examples you can share on that so we can see what it looks like in practice.

There's so many, and a lot of them are like somewhat tactical. As an example, we've known we want to do universal search for a long time because we've had different versions of our search experience in our marketplace that we don't love. And we've been using Jev as a newer model that's actually been really valuable for us to do, to handle lots of different types of queries at scale because we have lots of different types of products. We've also started to use Jev for content moderation because we have a lot of UGC that's being created and being able to flag, okay, which categories it's associated with in a cheap way is really powerful. We do a lot of, we summarize all of the coaching sessions that happen on our platform and provide kind of insights so that people don't have to have Granola and their Leland account. You know, we can really start to understand users and build a real deep understanding of what their goals are because we're pulling data from all these different sources. So I think a lot of it stems from good data foundations that all go back to trying to help the customer reach what they are trying to achieve. I think we're trying to avoid AI for the sake of AI. I think there, there are use cases that just don't make sense to use AI still, and, and, or could be better or faster in, in a different type of approach. But there are so many little things that we've done for customers on the, and then on the inside, there's You know, I think a lot of it is helping everyone at the company identify what they do every day and focus on the areas where they still, we still need the human in the loop. We have, as an example, we built this, we used to have a team of salespeople that were communicating via email all day, every day with customers helping them close because it was an email-driven sale. And we basically built a team of agents. There's a pricing agent, there's an SDR agent, there's like a closing agent, there's a few other agents that all talk to each other and coordinate and they work across different products and different categories. So they're kind of figuring out which products are best to sell. And that team of agents is now managed by an entry-level employee at about 15-20% of his time. And it drives over $1 million in sales every year and is growing and does it all night, all day, all weekend. And so I think a lot of it is just being able to leverage it in our go-to-market teams and our engineering. I mentioned our kind of coding agents we have, Coding agents have spit up the first version of most, most of our products at this point. So yeah, it's, it's, it's a constant challenge to figure out, do you build things faster or do you build the system that builds the things faster? And I think a lot of us are stuck there because AI, AI makes all of us so much faster that we just want to go and execute. And the reality is we're actually better off at this point spending time on this, on tinkering on the system itself. And when the output's wrong, instead of fixing the output, go fix the system and see if it spits out the right output the next time. So that's been kind of the journey we're on right now.

Those are lots of great examples. And I guess if we just think about like where it's having the largest impact, like where would you say it is with having the largest impact with the business right now?

Certainly coding is the most noticeable. I think that's probably true across industries, but there are pockets like this, you know, the sales agent that I mentioned that are just dramatic impacts. And so I think it's, it's now spread across everything, but I think there's still, you know, part, part of the, the AI builder program that we do with customers is like, you have to actually help people work differently. It's not just a normal tool that you adopt. It's like, it's like you actually have to approach your job differently instead of coming into work every day and just like looking at my email, I have to go start and whether it's in Claude or in GrokBot, which I've loved playing with lately, if you haven't played with it, like I have this whole, You know, agent team system and starting there every day is really great because it kind of gets a pulse of everything that's going on. And so I'm almost doing all of my work in GrokBot for the day or whatever. So it's like a totally different new way of working. So I guess a lot of it is just the impact showing up everywhere. It's showing up obviously in revenue with our new products, but it's also showing up in the internal stuff. And we, if we're going to sell this to customers, we have to practice what we preach, of course.

And I guess if we kind of zoom out, you know, what do you think like the, you know, future of kind of like career paths might start to look like in coaching? And then, you know, what leads The Leland experience will look like?

It's a good question. The future of the economy and jobs as we know it is obviously, it's a topic that everyone's kind of wrestling with. And there's been prominent people that have said we're all going to lose our jobs in a year and there's been, and then they walk it back and it's just, so, you know, I think the reality is no one really knows. It appears to be that the most valuable people are getting more valuable because of that last 1% or that last 10%, last 5%. If everyone can do the 80% or the 90%, then, you know, the, the person that's managing the, the final piece or creating the agents that are doing all of that work is, are, are especially valuable. And we see that with our customers getting offers or, you know, progressing in their careers in, in really kind of unconventional and aggressive ways. I think I still do worry a little bit about some roles and some maybe low skill, lower skill workers that have, have been able to thrive in the knowledge economy and who knows if they will be able to because of AI and how that's changing and how the value is accruing to the people that are wielding it. But that's also kind of the message that we have. We're trying to be a place for humans to thrive in the age of AI and figure out how do I wield these tools and how do I build an organization that empowers the people that I still do have at the company. So I think a lot of that is important to our mission is it's always been to unlock human potential and that just looks very different right now. We've changed how we structure the company. Now we basically organize the whole company in teams of like 1 to 4 that have what they call pods and they're like hyper-focused on very specific goals and need to have the autonomy to execute fast because their speed is so aggressive that if I had, if we have to like approve what they're doing, it's just a real problem. And so I think a lot of that's what we're seeing. A lot of that too is just re-architecting the actual teams themselves. And there's some companies are pursuing an AI team. Other companies are pursuing AI just kind of distributed across everyone. But we're seeing all of it. And I think from a Leland perspective, we're trying to evolve to help meet that, meet the moment. And I think what that will look like for us as a platform is continuing to double down on people in the AI era, which will involve things like community. It'll involve things like job boards. It'll involve things like you know, more of a destination and an everyday experience, which will probably, you know, look a lot more like LinkedIn over time. Hopefully a LinkedIn for the AI era.

I'm glad you actually mentioned that. As far as that team and work structure, that was something I was going to bring up so we could discuss a little bit of detail in the sense of speed right now as well. So I guess like, how do you think about that with like, it's, you know, being easier to build right now and it's so competitive in the markets?

A lot of it is it comes back to like Okay, how do I enable that speed? That's great. It's already happening somewhat organically, but there's always more you can do to make it faster. And then because it exists, movement without progress is like now the bigger risk because movement and activity is everywhere. And so that we gotta focus on direction. So a lot of my energy goes into prioritization and talent. So if we have the right people, and we can help them work on the right problems, we'll be in a really good place. And then I think it's how do we set the company up to have long-term sustainable moats, which I think marketplaces have unique advantages in. It's actually kind of funny that marketplaces, I would say, are generally like not in vogue. They're not the hot sexy thing right now, which is just so funny to me because like every other, like all these other SaaS businesses are struggling to stay alive and stay relevant. And I think the reason is because marketplaces generally are not token traders. We are not like selling tokens in different forms like many of the fastest growing AI companies are today. And so we don't tend to grow as fast as those token companies, but we are building probably much, much stronger network effects over time that can compound. And so What that means for us is we gotta figure out how to make sure we fund the business because investors like Andreessen used to be a really prominent investor in marketplaces. They used to publish the top 100 marketplaces and for it largely feels like that's no longer a thing, which is fine. But we need to make sure that as marketplace founders, we understand what that means for funding and capitalizing the business. So I think, and then obviously just building those long-term moats. So those are some of the threads that I'm Thinking about right now.

That's going to be helpful in topics that we're always discussing here. So it's good to kind of bring it up. You know, we're going to get to that group Q&A because I know that we had some questions. But I did— before we do, I did want to spend some time talking about fundraising because you, of course, raised over $20 million capital from some top investors like Forerunner, you know, FJ Labs. And we also backed you through Marketplace Capital. So I know a little bit about the fundraising journey, but I thought it'd be helpful maybe if you can share it here for others and then what some of your fundraising learnings are.

Fundraising learnings, I think, vary based on where you're at. I think In the early days, so much of fundraising is just you and it's your vision and really, but they're kind of assessing you through your vision and your presentation. And so I think a lot of that is just like, how do you communicate that vision clearly? How do you communicate strength in you and your team and your co-founders? And then that kind of graduates. I really enjoyed our Series A process a lot more than, I mean, I don't love fundraising, period, but I liked it more than I liked the early days because it felt like I was looking, we were looking at data together. We're saying, look, we're seeing some real movement here and we're, this is happening. You can't debate me anymore. In the early days, you could debate me if this was going to be a thing and it's just kind of my word against yours. And so if that's the case, like it's probably not fit. But in the Series A, we're looking at data and I think that will continue through the Series B. So, you know, obviously the team still matters at every stage. I think it's hard when there's, it's hard to accept the fact that when you get a no, it's a no on you. Like they don't believe in me and that's okay. They don't know me. They may not have any reasons to believe in me. But I think if you start there and understand, look, when they say, oh, our fund size is not, you know, we're not so sure if it's a little too early. It's like all those things, it's just, we don't know if you're good enough and these other things don't add up. And so we're just going to pass. And I think if you really understand that, then it makes it a lot easier to to approach things in the right way. Now, there are still legitimate concerns about market size or whatever that you need to address and have a clear communication around. So I think, you know, how to do that, I think I've gotten a little bit better at. I think the actual process itself too, so many early stage founders are kind of like, yeah, if someone wants to gimme a million dollars, sure, I'm available. And the reality is like, you just have to be, we are not raising, we are not raising, we are not raising, we are not raising until you decide that it is time to go raise capital and then to go and then go run a competitive process. I think that's true even when you get preempted, which I would say preempting sounds amazing until you realize that it's usually just like an uncompetitive process on someone else's terms, which is not good for you as a founder. And so I think some of these things and just trying to understand how do I create competition and find the right partners that are gonna be valuable to me and at the very least not get in the way. And yeah, I don't know. I think there's a lot of themes we could pull on there. Happy to go deeper on any of them.

Definitely. We'll probably save some for the group Q&A. I'm sure it'll come up. But, you know, of course, you're, you know, you're on the forefront of not only marketplaces, but AI right now. So, you know, what would be your top tips for founders starting marketplaces today?

Starting marketplaces, I think the— probably a lot of the marketplace fundamentals continue to be true. Excuse me. I think obviously there is an element of how do I leverage AI to provide a better customer experience? But I think at the end of the day, like marketplaces are a powerful business model because for the same reasons that they've always been really powerful business models and really powerful for delivering customer experiences. So I don't think, I think it probably goes back to fake one side and kind of get some initial traction. I think I would say invest early in moats that will compound. I think market— I always joke with my B2B SaaS friends that like the race to $1 million in net revenue for a marketplace versus a B2B SaaS company is much, much harder. It's really hard to get things going, but once you get it going, they have really powerful compounding effects that other like B2B SaaS companies don't necessarily always have. And so I think there's an element of being patient with yourself. I think starting a marketplace today, I would expect that investors expect us to go further than we used to go. Because of AI. And so, you know, don't think you need the full product experience. The people will work through a lot of pain if they want what you have. And so be— that's a good thing, right? If someone's climbing through the hurdles you're giving them with your terrible product, don't feel like it has to be perfect. Don't feel like that's the reason it's not working, I guess, is the platform itself.

Really helpful tips.

Cool.

So we're going to go ahead and get to the group Q&A. I know, Michael, you had a question. You sent me a message, so we'll kind of get to you. But also, Andrew, feel free to jump on here too. So I know Then we had some questions that founders sent that we could help ask.

Yeah, just listening in. This is great. I mean, the one thing I did want to double-click on if we have a minute is you talked about the Series A process and some of the metrics and looking at data. Obviously in a world where you're competing against all these AI, or not all, many AI businesses growing on the token sales side, like super fast. What were some of those metrics and what did you like? How did you get people Or Forerunner, whoever ended up leaning into really, you know, what kind of metrics convinced them?

It's a great question. I think the, well, also to be clear, I raised my Series A 2 years ago. So it was a different time. There obviously were still breakout AI companies at that time. I think the, first of all, it starts with finding investors that are still investing in marketplaces or businesses like ours. And so I think Forerunner had been clear that they were interested in these types of businesses and still are. I think their growth is obviously a big deal for us. I think it was at the time we were probably crossing $6 million in GMV and maybe $2 million in net revenue. I think it was around those, those kind of where we were at the time.

Okay.

And, you know, I've grown a lot since then, but I think the inflection that we were seeing was unique. And so I think a lot of it does come down to like just compounded growth. I think there also at the time was, we had sort of accidentally become cash flow positive too because we had grown into it. And that, I think that was really valuable for us to say in the fundraising process, hey, we don't need to be here. We have cash in the bank. We are cash flow positive as a business, but we are here because we see this huge opportunity and we want to be aggressive about it. And so I think investors respect to like, oh, like my downside scenario is really protected here. This company can be efficient if they need to, but the upside scenario is them trying to go get, you know, be aggressive and build something real. I think it's a Series A. The reality is like the metrics still matter a lot less than I would expect them to matter at a Series B or Series C. I guess unless you're an AI company and you, you know, have raising a massive round with very little. But I think that the metrics obviously get more important over time. And in the Series A, they're still really just looking for signs of product market fit. So if seed is like, you know, good team in a big market, Series A is product market fit starting to happen. And Series B is like, you have an engine that we understand and can really scale, step on the gas and scale it. That if that was like kind of the, that's kind of how I've thought about it. And so for me, a lot of the Series A was communicating through data that we have clear product market fit. Sometimes that's customer love, sometimes that's markets opening up, sometimes that is just growth or traction. But I think trying to give them everything they need to feel like, oh, this is a real company that's growing.

That's a great question. Hey, Michael, sorry, raise your hand.

Thank you so much for taking the time here. I had a question. You hear a lot about these personal AI agents for consumers like Instinct, Muse, some of the other ones. As a services marketplace like yours, do you, A, just ignore that noise for now? B, do you try to ready the marketplace to integrate with it so I can text Instinct and say, hey, I— how do I get better at AI? Or C, do you offer a sort of agent-based interface where people can just, you know, chat instead of, you know, use form-based navigation? I'm just curious your thoughts on that, like, down the road.

It's a good question. I think, um, I guess my— I'll tell you my impression, and it may not be the right one, but I think there, there's— I have thought about this a lot. I think at this point, maybe, maybe in the early days, I feel like I was more affected by everything happening in the market because there was just, you know, you're new. And so someone launches a company that looks like yours and you're just stressed like, oh man, it's the same company. This looks so similar to mine. And I'm now seeing, I don't even know, like 50 competitors come and go of different forms. And ultimately, like, I think for me, it all just comes back to the customer. And so if I start to see my customers or hear my customers say, hey, I really need an Instinct integration in order for me to continue to be a customer on Leland. Like that will wake us all up, right? That, that's obviously super important. And, and they won't always come out and say it exactly like that, of course. But, but I think it's really understanding like why, what are they desperate for? What are we providing that's kind of filling that gap? How is it different than, than one of these products? And I think that, you know, when we were, when we were first starting, Web3 was all the rage and we had so much pressure to build Leland on the blockchain, which is like the craziest, in hindsight is like the craziest thing ever, you know? And I'm not comparing AI to, to Web3. It's obviously very different and I think it's, it's clearly here to stay in, in many forms. But I think ultimately it's like our application of AI or how we integrate or how we partner is going to be, is going to come back to what we're hearing and seeing from customers. So, you know, Instinct and Muse and all these are so new that it's, It's hard to say that that's like become core to their workflow and they're still coming to Leland for other stuff. But yeah, if ever, if that becomes like, if everyone has one app on their phone and that app is like their AI personal assistant, then, you know, of course we'll be more aggressive in that. So I don't know, I think that's, it's not really a specific answer as much as it is like the way I think about it is just, it always comes back to the customer.

Hey, uh, Steph, saw you raise your hand. You, uh, want to jump on?

Yes, thanks, Mike. Hi, John. Thank you so much. I want to go back to the early days. I think it's about this intermediation. So once a client finds a coach on Leland in the early days, what actually stopped them from moving off the platform? And you, I know that you started talking about like how demand was super important. So I guess that maybe is related to this question, but I want to hear what else you were doing, like product features, incentives, that worked, which ones didn't, or which rules did you apply to the marketplace to guarantee that that relationship stayed in the platform? And the second one is supply quality at a small scale. So how did you vet coaches enough before the platform had reviews or the coach had enough reviews inside the platform?

So yeah, on the supply side quality, we really tried to vet everyone before. We would let coaches import reviews as like a one-time grace. Like you can do this. We make it clear in the product, this is a review from off Leland. So it's not like we're not trying to steal reviews. It's more like, hey, you can, if you got reviews from this other on Google, like you will or whatever, some other platform, we'll put that this, this review was imported from Google, but it still helps them build some sort of credibility. Like they're not so brand new. But we just sort of like vetted them more aggressively than we would. Well, actually we still kind of vet them all pretty aggressively. But especially in those early days, it was just so important in terms of disintermediation. So there's a lot of things that we've done. It's always some amount of problem here, but I would say this hasn't affected us as much as even really I would've expected. I think a lot of that comes from us telling, well, let me back up. The stick is only so effective in disintermediation. Like the carrot's usually stronger. And so like we will use the stick, we'll say to our coaches, is you cannot take people off platform or you will get kicked off. And we will, if we see that behavior happening, we will tell them that. And we will threat— we will threaten to kick them off. And that does help to some degree, at least so they know. And we're pretty upfront about that in onboarding. But I think you obviously want more of a relationship around like, why do you want to bring more platform, more business to the platform? And so communicating like, hey, look, you're going to show up much higher in search results. We're going to show things like minutes coached on your profile. We're gonna show things like customer favorites. We're gonna show things like top experts, whatever it is. Like we're gonna show a lot of things on your profile. The more you do here, I will say there are some structural challenges with frequent in-person transactions. So if you have a marketplace that falls into that bucket, we don't have that. But frequent in-person, it's like every cleaning, house cleaning marketplace out there, or, you know, you name it. I have a good friend that started a company that has This type of dynamic. And it's like once you meet in person and you become friends, it's just really hard to like overcome that as a platform. There are still some things you can do. There's some platforms that have figured this out. Obviously Thumbtack, the way that they approach it is they actually monetize the lead itself rather than monetize the ongoing relationship. And so if you fall into that bucket, which Thumbtack does, it's like as soon as I meet this lawnmower, I'm not paying Thumbtack again. I'm paying the lawnmower directly. So Thumbtack needs to know that. So they need to say, great, Lawn Mower, I'm going to charge you $200 upfront because I have to make money on this relationship and I know you're not coming back. So I think some of it is just like economic models that you have to play around with depending on the type of marketplace you're building. But in the early days, yeah, it was, I mean, there's a lot of trust. A lot of it was relationship capital. It's like we try to build relationships with the coaches and tell 'em what we're doing here and how we need to, what we need to do to survive. And then also not being too aggressive on take. Until you kind of earn the right. And we have different incentives too. Like we will waive our take rate if they brought the lead on themselves or reduce it dramatically. So there's certain things you can do to try to get the sweet end of the deal.

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

Thanks, Jonathan. Super interesting. And I've looked at Leland, I know it. Quick question. Most people come to Leland, I'm guessing, at some sort of moment, a deadline, right? An MBA application, a job search, a pivot. What have you learned about the kind of the stretches between those moments? Does anyone keep paying when nothing is urgent? How do you get them to join when prior to this event in their lives? Obviously, this is probably the age-old question around these type of services around HR tech.

Yeah, willingness to pay and urgency and desperation just goes way up when there's a deadline or there's some, some clear moment or ROI. So usually the best time to get them in is around one of those times. Like it's hard to get them if it's just like general career growth. Now, I'd say that that's like, if the first 5 years was about winning on those moments, like the next 5 years will be about winning on an ongoing basis. And so a lot of that will be how do we build communities that are always on? How do we build additional value that can help people grow in their career? Even things like this whole learning AI, like learning AI doesn't necessarily have a moment or a category or like a timeline. But has been, you know, something that we've been able to solve. And then I think that also introduces new buyers, right? So if the consumer isn't willing to pay for themselves to learn AI, the business is looking at their goals and saying, hey, maybe we are. And so I think that's, that's been important too, is adding a new business buyer. So it's, I think it's a kind of a combination of providing ongoing value. You have to be able to earn that over time, teaching our customers that we can help them with multiple goals. So we've now seen many customers come back to us You know, even if it is like I come back every year or every 2 years for something over time, like that's a really valuable customer. And then the other thing is like not stressing too much about it because these customers, if you can change their lives and help them get that job or whatever, they will scream your name from the rooftops to the next wave of 50 people that are going to come and try to get a job. So making sure that those referral engines are really healthy too. So even if they themselves aren't repeating immediately, You know, the first person everyone goes to that when they're trying to get a job at Google is like the people that are there at Google that just got the job. And so trying to be, you know, build relationships there. And that also has, that also is related to like how we engage our supply. So supply is often a demand driver as well. And so figuring out how do we engage and leverage supply to drive growth as well has been important.

Awesome. We'll try to get in one last question if we can. Hey, Hugh, I saw you raise your hand. Do you want to jump on?

Cheers, John. Thank you very much for coming on. Very interesting. Got an interest, a question around about maybe the early days and how you looked at generating the network effects on the demand side and what marketing channels you found. Like, did you experiment with different marketing channels and then found one that really worked and then doubled down on it? And what was that journey and how that evolved?

Yeah, I wish I could tell you that there was like one marketing channel that just really worked. But they all like, they all kind of contribute. I think word of mouth has always been our biggest channel. So making your customers happy is like obvious, but is, is, has definitely been our biggest and is the hardest to measure and the hardest to game and the hardest to control, but is like the most important. SEO was really valuable for us. It's gotten a lot less valuable over time. So that's, that's too bad. But that's also, I mean, obviously AEO and, and kind of how you integrate with LLMs matters a lot. Organic social has been specifically LinkedIn has been valuable for us. But I would say we're still on the journey of like figuring out how to crack it and scale it. But yeah, I would say it's largely just a combination of all of them that have been valuable and trying to continue to test and experiment and figure out where the ceiling is on each of them. And then when something is working even a little bit, like do that 10 times more before we go try to find the next channel.

Hey, John, I actually want to jump in here and ask a question for a founder. It's somewhat related. It was around community. So can you share a little bit more around the role community plays for Leland?

Community can take so many different shapes. Obviously, I think the— but it's always been really important. I mean, relationships have been at the core of Leland for a long time in the same, you know, same, same reason for us. You know, I know that donuts are bad for me and I still hire a nutritionist to tell me not to eat donuts. Like, there's a lot of, I think a lot of like value in the accountability and the relationships that people have. So that's always been important. I would say that in the next 2 weeks in particular, we're going to make a pretty big bet into community and actually build more of an integrated community on Leland itself because we believe in the power of that. And I think, you know, I obviously learned a lot of the power of that through LinkedIn. Getting that right is super hard. But I think, you know, we've added live streaming on Leland. So people, we have thousands of people joining our live streams every day and week. And so we've invested a lot in that live experience. We're going to invest a lot more in kind of an always-on community experience. And then obviously the relationships were core from the beginning. So yeah, we believe deeply in it. I think we're still figuring out the best and most scalable and impactful ways to implement it.

Well, that's a great way to wrap things up with a preview of that, right? Of the mention. So yeah, you know, so we're almost out of time. You know, huge thanks for taking the time to join us here today for the group chat, you know, sharing all of your experience at building Leland and helping answer some of the questions that we had during the group Q&A. And of course, you know, all big fans of, you know, what you're building and appreciate, you know, paying it forward with the group chat. But I want to ask my usual closing question, which is that if you could go right back to before you started Leland, you know, what would you tell yourself about marketplaces?

Always fun to chat with people that nerd out about marketplaces. It's a— there's a lot, lot to learn. And if we can be helpful in any way, feel free to reach out. Or if the, you know, if the AI Builder Program would be helpful to your organization, definitely let me know. I'd be happy to give you a discount. I think if I could go back to the very beginning of Leland, there's, oh, there's so much. I think there's been times where I've sacrificed customer resonance for scalability and almost all the time that's been wrong. And maybe the other one I would say is constantly checking what I'm hearing from customers and my vision and which, like making sure that those always connect. Because there's been times where I've been so customer focused that it's actually taken us down the wrong path, not because the customer's wrong, but because the type of thing we wanted to build was going to be slightly different and there were multiple ways to go about it. And there's been other times where we're trying to build the vision and we forget to just listen to the customer. I think it's obviously a higher level thing, but I think that's probably been where most of my biggest mistakes have come in, have been not connecting the vision to the customer and the customer to the vision.

Great parting advice. Probably lead to a whole other conversation here as well. But time for a quick plug before we wrap things up. Where can we all follow along and keep up with you at?

Yeah, I'm pretty active on LinkedIn, so feel free to add me on LinkedIn and Twitter as well. But Yeah, that's, that's probably the best place.

Awesome.

Well, I'll be sure to include all the links and also too for the AI Builder Program so everyone can check it out. But no, we appreciate you paying it forward and joining us here for the group chat today. As I mentioned, it's a fun one since you've been part of the community since the early days. And thanks everyone for the great questions.