Steadcast
Masters of Scale cover art
Masters of Scale

Building a marketplace from scratch, with Hipcamp founder Alyssa Ravasio

October 8, 202632 min · 7,364 words

Show notes

Alyssa Ravasio loves using ‘coyote trickster energy’ to get more people to put down their technology. Her camping marketplace, Hipcamp, has grown into the largest source for booking campsites on public and private land. She talks with host Jeff Berman about scaling the company, learning to prioritize your health as a founder, and more.

Highlighted moments

I did not have clarity on how we were going to make money. How are we going to build a company? What was that going to be? And especially when all these people were so upset if we were marketing anything that wasn't booked.
12:23
“it was only through that lens that private land just jumped off the map because we would have created a whole new way to get outside, changed outdoor recreation, solved the root of the problem, right?”
13:00
“Before we had a policy like that we could share with our landowners, it was almost impossible to get anyone to sign up.”
16:55

Transcript

Introduction

0:00The very best founders I know are brilliant at building systems. They connect teams, they remove bottlenecks, and they eliminate single points of failure. And yet, when it comes to their own wealth, most are running a disconnected stack. A tax accountant here and a state attorney there, a wealth manager who doesn't talk to either one of them. Creative planning was built to fix exactly that. One integrated team of tax professionals, state planners, investment specialists, all coordinated by a dedicated wealth manager who sees your full financial picture and keeps every piece working together. Proactive tax efficiency, state strategy, investments all under one roof. Creative planning, where wealth works together. Learn more at creativeplanning.com slash mastersofscale.

0:52We've all spent money on something that seemed incredible, but didn't live up to the hype. A kitchen gadget, a car. When it doesn't deliver, the disappointment is real. Marketers suffer from this too, chasing metrics that look great, but don't translate into revenue. LinkedIn calls that bull spend. Invest in what matters and reach the right buyers with LinkedIn ads. You can target by company, industry, job title, and more. LinkedIn ads. LinkedIn ads also generates the highest ROAS of all major ad networks. Spend $250 on your first campaign on LinkedIn ads and get a $250 credit for the next one. Just go to linkedin.com slash scale. That's linkedin.com slash scale. Terms and conditions apply.

1:39AI is full of possibilities. But then it was combining that with nature and the outdoors. I did not have clarity on how we were going to make money. How are we going to build a company?

2:16When did you know it was working? I remember waking up that morning and opening up our, you know, backend systems. I think we'd gotten like four or five people to sign up at that point. And there were hundreds. And I got to just scroll through. And I started crying. I bet. Yeah. Cause you're like, Oh, people want this. I would get really angry letters from people. That's the last place that I could still go without six months notice. Oh, they were gatekeeping. They were gatekeeping, but it's also genuine scarcity. The biggest challenge has been like managing my own health and energy. I got shingles at one point.

2:49I feel very lucky. I went into the ER that day and the doctor took one look at me and said, this is shingles. You're way too young for shingles. Can we talk about our job? What's going on? Cause they knew this was stress related. Absolutely.

Why Camping Booking is Broken

3:07With us today is Alyssa Rovasio, who is the founder and CEO of Hip Camp, which if you are camping is the way to book your spot with, I think over a half million locations now, millions of trips booked. This is a really interesting scale story. Welcome to Masters of Scale. Thank you for having me. Excited to be here. I'm thrilled to be here with you. Why this problem? Why was this the problem you wanted to take on? I was really lucky. My family went camping a bunch growing up. My childhood is filled with memories of making mudslides, catching frogs, rekindling the fire in the morning from like early little embers that were left over. Like that's how I think of growing up.

3:49And when I started trying to have those experiences more as an adult, trying to book a campsite for myself, I really couldn't believe how broken, how fragmented and how difficult that process was. You know, at a moment when you can order any food, a car, a hotel with like the click of a phone, like why, why is getting outside still feel like we're in the 80s? And the idea was just to make it simple to get outside in hopes that that would get more people outside. You started HIPCamp in 2013. Is that right? Yes, it's been a little over a decade. So it's post-launch of Airbnb.

4:21Yeah. Math is right. Was part of it like, let's just do Airbnb for camping or did you have a different vision for what this would be? Yeah, it was a different vision to start. So originally we were totally focused on public campgrounds. I had a trip I'd planned in particular where I was looking for a campsite on the coast to show my boyfriend how beautiful it was. And when you want to camp on the coast in California, that could be a national park, a state park, a forest service park, a county park, maybe even a private park. That's like 15 different websites. Like the fragmentation was really crazy.

4:54This trip in particular, after planning for hours, choosing a campground, I found out once we arrived, we walked up to the campground. Everyone had like surfboards and wetsuits. And I was like, what's going on? We walked out to the coast and there was a beautiful surf break. And I love to surf and I had left my board at home because even though I'd done hours of research, no one had mentioned that. Oh, you're so bummed. I was so bummed. So the first version of Hip Camp, which is called California Camping, by the way, was really just about pulling together that fragmented information and creating a space for campers to help each other learn about what's good to know about each campground.

5:31And so the first version of the problem was I wanted to put the existing campgrounds in a map, but it actually took a few years until we realized the problem had a much deeper layer. Alyssa, did you envision it as a business at first or was it more a coding project to solve a problem for you that might be helpful for others as well?

Early Career and Starting Out

5:48I wanted it to be a business because I didn't want to go get a job. I had worked at a couple of startups before Hip Camp and I'd learned a ton, but had also learned as part of that time that I was really wanting to run my own company and kind of be my own boss. Can we click in on the couple of jobs that you had? What did you learn there that said to you, this is not for me, I'm going to go start my own thing?

The biggest thing I learned is that when I figure something out, it's really hard to not act on that. I found myself in situations where I had to do something that I didn't think was the right thing to do. And that killed my soul. I couldn't do it. It was just like, this is not what I want to put energy into. This isn't how I would approach the market.

6:26Things like that that just really led me to decide, you know, even though at the time I was, you know, 23, like it's time to start a company. It's time to get to do things in the way that I think will be best and feel, I guess, most exciting to me. I've always liked starting things and leading teams. So my first business cards for my first company, I got my dad to print when I was, I think, 10. Baller, walking around. Yeah, it was Spiral Films Production. We made movies. My sisters were my employees. I paid them in mac and cheese.

6:56Awesome. Yeah, because I was the only one who could use a stove. Right. Well, you know, there you go. That's leverage. I had a resource locked down. I needed the right idea. I knew I didn't want to just go start something to start something and see if I could make some money, right? For me, it was about solving a problem that I thought was worth solving, right, and was worth the years and the energy that it would take to solve that. I really had a good understanding of scale and the Internet and how this new technology can totally change and will totally change how the world works. But then it was combining that with nature and the outdoors and the passion I have for getting people to basically, you know, reconnect with the biosphere and nature.

7:35It was like those two things together that that was that was worth going all in on.

Learning to Code and Finding Traction

7:40How did you actually get Hip Camp off the ground, both from a how were you financing it and how did you get a website or an app in consumers' hands? Yeah. So originally, I had to learn how to code and I had this idea and I tried to start a couple other startups, maybe like in between different moments at different parts of my life. And that it always required like the big blocker was finding a software engineer who wanted to build this. And I found that it was just time to be able to do that on my own. And so I went to Dev Boot Camp, which I just started at the time.

8:12Right. This is before Vibe Coding. Gosh. Yeah. Yes. Yes. I don't regret learning to code, but man, things would have been a lot faster if I had had Codex. That would have been great, but I did it. So I learned how to code and I ended up enlisting my sisters again, my first employee.

8:31And a couple of friends and actually, you know, building this very early version of the site that actually got some traffic and got people using it early on. And we got traction. We got people. I think we were getting close to having probably one of the biggest search engines for camping. How did you find those customers earlier? How did they find you? A little of everything. I mean, this was an era where I was going to like every meetup I could. I would just walk around with my laptop handing out stickers. Big sticker fan. I brought stickers. Nice. And so I would just ask people, do you like to camp? And if they made the mistake of saying yes, I was like, well, let me show you this and open the laptop.

9:06And, oh, do you see that place to put your email and put that in there? Oh, good. It's working. Big shout out to REI on Brannon. They let me sit at a little card table I'd bring and set up in front of their front door. Wow. So I did a lot of that. Really hand-to-hand marketing. Yeah. Yeah. Because it wasn't even, it was marketing. It was also feedback, right? It was also this idea of we're going to build this product in collaboration with community. I'm going to get input and understand what they're looking for, what I have that they love, what I don't have yet. And actually kind of like our, one of our big break moments was a digital version of that where I got like a customer support email where someone was suggesting we had a filter for pets.

9:44And we were working on that. And I was like, great. I wrote back right away. I was like, great. Yes. Thank you for your feedback. We're working on that. I'll let you know when we ship it. And then suddenly I started getting traffic notifications from Google. It was like your traffic spike. And I was like, what's going on? And it turned out the person I had emailed back had a big Twitter following. And they liked my response and they had tweeted out, you know, go check out Hip Camp. We actually got in that first big, you know, traffic burst and I got a bunch of like emails. And one of them was from Dave Morin, who ended up investing a quarter million dollars later that month.

10:18But like, it was kind of crazy, right? That like a customer support email led to a tweet, led to, you know, our first funding round. And yeah, Dave's been a great champion and partner ever since. Well, I love that story about the customer feedback and your response, because one, it goes to clearly a commitment to serve in your community. But two, if you treat every customer, every community member like a VIP, you just never know. Totally. Zeus's law, right? Right. Okay. So you're getting traction, you're going, you're building a real following, a real community.

10:50But you're at this point, really sort of a guide and a search engine. You're not a marketplace. Right.

The Scarcity Crisis and Private Land

10:56What happens? Crisis. Never let a good one go to waste. No, I mean, and it was existential at the time. So our mission from our origin has been get more people outside. And we really mean the more, right? We want people to connect with nature and get out there more often. And we had this great, you know, search engine and directory and we're getting lots of cool reviews. But what was happening was every time I would find a campground that wasn't fully booked and I would put in an email or, God forbid, put it on the homepage, I would get really angry letters from people.

11:29That's the last place that I could still go without six months notice. Oh, they were gatekeeping. They were gatekeeping, but it's also genuine scarcity. Like, I remember one email I got where someone was explaining, you know, I need to be able to get outside on the weekend if I've had a hard week. This is the last place I can do that. Please don't ruin it. I was like, oh, my gosh, how are we going to make our mission happen if the existing infrastructure in most cases, many cases, is already at capacity?

12:00I'll always remember this. I went, it was an Italian restaurant in North Beach with paper tablecloths, which are amazing. If you're having a really hard time, go somewhere with paper tablecloths. Especially North Beach. Yeah. It's like a big whiteboard at your table. And I wrote, I started writing down potential business models. Now, keep in mind, we've raised money at this point. Bryce Roberts from OATV had led a seed round. Dave Morin had invested. I had great investors. And I did not have clarity on how we were going to make money. How are we going to build a company? What was that going to be? And especially when all these people were so upset if we were marketing anything that wasn't booked.

12:34And so we literally wrote down everything from advertising to, like, a cool gear delivery to private land. Private land was, like, a very niche idea. I'd gotten a couple emails from landowners who had suggested it. I hadn't really been to much private land on my own, so I was kind of dismissive of it. And I ran an exercise where I said, if this business model was wildly successful 10 years from now, 20 years from now, what impact have we had? And it was only through that lens that private land just jumped off the map because we would have created a whole new way to get outside,

13:07changed outdoor recreation, solved the root of the problem, right? The root of the problem was there's not enough great campsites. There's not enough supply. And in doing so, created this amazing model that could scale recreation for conservation. And so it was really through that lens that we chose private land. But it had a lot of question marks at the time. It wasn't a sure thing at all. Well, I love this for so many reasons, not least of which being you had real customer feedback, which I think for a lot of entrepreneurs have been exasperating. It's like, I'm trying to do good.

13:38I'm trying to do a service here. I'm sorry it's, like, harshing your situation. But, like, it's net good. And really what you realized was there was a supply-demand problem. There was a different way to attack it. Can we just go back to this North Beach Italian restaurant? Is it you alone? Are you there with your team? I was there with my husband, though. With your husband? Yeah. Was it intentionally, we're going to go here and we're going to work on this? Yes. Or was it, yes. We're going to solve the problem tonight. Okay. Gotcha. A lot of intention. With or without wine. Definitely with red sauce.

14:08Definitely with wine, too. Yeah. And so as you're using the paper on the table as your whiteboard and you list out private land, was that the aha moment or was that the start of the unlock? It was a start because a lot of business models, you ultimately end up helping people trade money for time. Yeah. Right? They're models of convenience. That wasn't super compelling to me. The aha moment was realizing this would change the way the world works for the better. This would solve this problem I've been obsessed with.

14:40It would solve the root cause. Yeah. It could switch the system that's in so much scarcity into abundance. Okay. That's worth working on. Yeah. Oh, and by the way, if it works, multi-billion dollar company. Okay. I'll go that direction. And so it wasn't until I looked at it through the longer term lens that I saw the potential. But then I think the real aha was really the next morning. I think I emailed our entire user base and I said, I will give you $500 if you introduce me to a private landowner who lets people camp on their land. And I got a lot of responses. And so I spent the next week going and visiting places.

15:13And one of the first ones I visited, it's called Mendocino Magic. It's still on Hip Camp today. It's an incredible spot. It has, I think, the largest private lake in the state of California. Oh, wow. And I was walking around this lake with Mackenzie, the landowner, and I just, people would love to camp here. And she was, her parents were talking about maybe having to sell the land. She was looking for a way to keep it in the family, keep it protected. It's got a lot of redwoods. If she sold it, it was going to get logged. The owls were going to lose their home. The foxes were going to lose their home. So she was really on a really similar mission. And I looked around and said, this is going to work.

15:45We can do this together. How did you approach the scaling of the private land component of Hip Camp? Yeah. So we kind of used the public existing campgrounds, which were public data, as a way to bootstrap supply. We were like, oh, we have supply. And then the demand showed up, right? And so as we added private land, it was really just about more supply, better supply. This supply you can book. This supply is beautiful and private. And so it was really, it was pretty seamless, actually. And I think one of my other big learnings is most people, they want to camp somewhere

16:16beautiful and somewhere private. And whether it's managed by the Forest Service or California State Parks or McKenzie, it's all good. It started working pretty quickly. I think that's one of the benefits of having the demand ready to go. So I am a lawyer by training and I still practice a little bit. This is not my area of expertise. But I will tell you that the lawyer in me is starting to think about all the liability issues on both sides here. How did you approach that? So getting insurance was one of the turning points for the company.

16:47We now have a really great general policy where all of our landowners are covered. We're covered. There's, you know, all sorts of different layers of that. Before we had a policy like that we could share with our landowners, it was almost impossible to get anyone to sign up. Hey all, Reid here. We're pausing briefly to share some exciting news. Masters of the Scale Summit returns October 20th to 22nd in San Francisco. If you've joined me at Summit before, you know how different it feels from other business or tech conferences. Van Jones calls it the highest concentration of heart with smart you're ever going to find.

17:22Every element of fascinating business insights, curated audience of founders is designed to spark ideas that transform your business. The impressive lineup of speakers for 2026 may be the strongest yet. Leaders like Netflix's Reed Hastings, Repplet's Amjad Massa, journalist Kara Swisher, Noble Lore, Maria Ressa, Walmart's John Furner, and Cloudflare's Matthew Prince. Be in the room this year and walk away feeling it's possible to scale your next great idea. Join us. Visit mastersofscale.com slash summit to learn more.

17:54Stripe Treasury is your new financial operating system built for what's next. With Stripe Treasury, the place your business accepts payments is also where you can store balances, move funds, and pay vendors worldwide. If you're building for global scale, get a business bank account that lets your money move instantly whenever and wherever you need it. Learn more at stripe.com slash treasury. Stripe is not a bank. Banking services provided by Fifth Third Bank, National Association member, FDIC.

18:30We all know the disappointment that comes when a grand gesture falls flat, something that seemed impressive in the moment but didn't deliver the results you expected. Marketing budgets too often fall into that trap, aiming for big impressions, big reach, but without the revenue to back it. LinkedIn has a name for it, bull spend. LinkedIn ads generate the highest ROAS of all major ad networks. They target by company, industry, job title, and more. Spend $250 on your first campaign on LinkedIn ads and get a $250 credit for the next one.

19:04Just go to linkedin.com slash scale. That's linkedin.com slash scale. Terms and conditions apply. When you've built substantial wealth through your business, it's often tied up in a single equity position. The upside is real, but so is the risk, and knowing when to act isn't always obvious. Creative planning works with business owners to build a strategy around concentrated equity, when to diversify, how to manage tax risk, and how to protect what you've spent years building.

19:36Creative planning, where wealth works together. Learn more at creativeplanning.com slash masters of scale. I imagine being on your board or an investor in your company and asking the question, what happens if Airbnb wakes up tomorrow and says they're going to do the same thing? Yeah. Every time we raise money, that is a big question. What I have said to that in the past is that when you want to get outside, that's such a different mindset than when you're looking for, you know, a good alternative to a hotel or a house to rent.

20:08It's just a different use case and a different brand. And I think while there's some overlap in customers, it really is just a different way for people to be thinking about what they're looking to make happen in the world. And so it could, of course, you know, not to tempt anyone here. They could, maybe. But I think it would be very difficult and a very hard thing that would require different branding, you know, different setup, different product, all of that. Well, and also you're at a scale now where the build by partner analysis for Airbnb would be very different than it was then.

20:38Yeah. I mean, scale is the ultimate moat for a marketplace, right? Like network effects are amazing. And it's just, it's so fun to build a business that I couldn't imagine feeling this level of enthusiasm for the business we're building if I didn't understand and see every day how every unit of supply we add makes it better for every camper and every camper we add makes it better for every host. Like that, that to me, that scale, that network effect is what, you know, that's what's so exciting about the business model. When did you know it was working? We partnered with a really large, um, I think it was like a regenerative organic farmers

21:11association and we had them email their, their newsletter and say, Hey, if you want to host camping sign up, we didn't know, do people want to do this? Do people not want to do this? I remember waking up that morning where they'd sent out the newsletter that morning and opening up our, you know, backend systems. I think we'd gotten like four or five people to sign up at that point. And there were hundreds and I got to just scroll through and I started crying. I bet. Yeah. Cause you're like, Oh, people want this. And my inbox was full of notes from people who were like, we've been talking about doing this for years.

21:41We've got the perfect, I remember like a strawberry farm on an Island. And they were like, well, we couldn't afford the insurance, but we couldn't figure out how to market it. We couldn't figure out how to reach people. And I was like, Oh, this is going to work. When I knew we had demand, that's never been the problem. Now we have supply. What an incredible signal. Will you situate us where in the journey you are when this happens? That was probably 2017 or so.

Managing Health and Personal Burnout

22:00Okay.

Managing Health and Personal Burnout

22:01Yeah.

Managing Health and Personal Burnout

22:02What are some of the biggest challenges you've had to tackle that you didn't foresee that night in your North Beach Italian restaurant? I think helping people think through infrastructure and the right thing is important. Probably regulations are another one. Are you familiar with AB 518? I mean, I am because I prepped for our conversation. So just last year, California passed pretty amazing legislation that creates a new regulatory framework counties can opt into that allows people who have, you know, bigger parcels, mostly targeting farmers, ranchers, land trusts, things like that, to have up to nine campsites

22:33without needing to get the really onerous permit that is required for like an RV park before there wasn't like a separate lane for these lower impact type of campsites. That has totally changed the game. So it's been amazing to see the coalition around this, right? It's everyone from, you know, the Farm Bureau to the Nature Conservancy, right? Like when's the last time like all the farmers and all the conservationists and all the small rural businesses all agreed on something? Outdoor rec is such a powerful economic engine.

23:04Like outdoor recreation means trails. It means boat ramps. That's not just going to bring in visitors. That's great for the people who live there as well. And so that's really created, I think, a groundswell of support around, you know, regulations to better support more outdoor recreation. So what's been the biggest challenge since you incorporated private land and HIP camp really took off? I think for me personally, the biggest challenge has been like managing my own health and energy. Oh, say more. Why is that? I'm a pretty obsessive person and very passionate.

23:34And I believe so much in what we're doing that it can get really easy. And especially, you know, maybe a few years ago to start talking yourself into making sacrifices that don't make sense. Sacrifice sleep. Sacrifice a workout. Sacrifice a healthy dinner, right? Like these kind of little things that each one on their own feels like justified in the moment. But over the course of a few years really starts to pile up. I got shingles at one point. I feel very lucky. I went into the ER that day and the doctor took one look at me and said, this is shingles.

24:06You're way too young for shingles. Can we talk about our job? What's going on? Because they knew this was stress related. Absolutely. Yeah, absolutely. And so I think learning to build, you know, the right systems, the right habits, there's no glory in like becoming unhealthy in pursuit of this mission. So I'd say the real unlock is more knowing that like your body and mind are worth taking care of. And that if you're really in solving a problem and building a scaled organization that's going to help shape culture for decades, you got to take care of yourself.

24:38And like you are worth taking care of. And so, so many times I'll talk to early stage founders who are just really struggling and they're exhausted. It's like, okay, let's try to take care of that first. Because the second you're tired, you lose your creativity. You lose your problem solving. You come up to a challenge and instead of getting curious about how to get around it, it feels like a, you know, a drama, a stress. It's the end. And so I think, yeah, that's actually probably been the hardest, the hardest part of all of this for me. How big is the company now? Close to 100. 100 people? Yeah, we're now the largest search engine for public land.

25:13We're the largest search engine and booking engine for commercial campgrounds, which we haven't gotten into yet. But one of the benefits of scaling this company through private land is now all the existing campgrounds also can benefit. They can join. And I think we're sending more bookings now to commercial campgrounds in the U.S. than any other platform by nearly an order of magnitude. And then, of course, we're the largest search and booking engine for private land, which is a category we essentially created and have really been able to scale. And so it's really those three pillars together that have created the hip camp of today.

Remote Work and On-Site Culture

25:44Alyssa, is the company remote, hybrid, or in-person? So we're mostly work from home, but we do a lot of in-person work. So I'm happy to talk about that because that was a whole journey. How do you do in-person? Lots of ways. We have a space in San Francisco we go to sometimes, but then we do a lot of on-sites where we bring everyone together. Not everyone, but the right group of people. So I'm working with people in-person probably almost every week, every other week. And then we do bigger company camping trips and campouts. So you do on-sites at campsites? Sometimes, yes. And what do those look like? Generally, it's like we've identified a really important problem.

26:16There's just certain problems I think are really hard to solve on Zoom. And when you feel that, you just fly everybody in and you're like, we're solving this. We're not leaving until we do. It's one thing to bring everyone into an office. It's another thing to bring everyone to Mendocino Magic or another one of the campsites with which you work. What drives you to bring people out into nature to one of your partners and set up on the land and work there? I think for us, being at a hip camp means you get to see the product in action. And it's just deeply inspiring. It's so much more meaningful if we're talking about how do we create more great campsites.

26:50Our number one objective has been for a long time, if we actually get to go walk the land. So recently, we had an on-site out in Stinson. We got to go walk around Slide Ranch, which is a beautiful hip camp and nonprofit that has a mission to get more kids rooted in nature. And they have great campsites. And they use that revenue to fund scholarships. We got to walk around, hear from the host about those scholarships, about the direct impact our work is having on helping her organization go from being in a pretty serious deficit to being in the black. And then we got to walk through the campsite and see the people who were like setting up their tents.

27:22And we're going to camp on the edge of the Pacific Ocean for the night and seeing people having these moments of exhale and peace and being like, that's what all of our hard work is making possible. When we talk about having our core company, North Star, as nights outside, that's our core KPI we're always tracking and working towards. And when you get to the millions, it can start to feel abstract. And then, you know, getting to walk by a campsite and see, I did this just last night. I saw a mom with her son setting up and I was like, that's one. They're going to have a magical night. He's going to remember that forever. It was an eclipse.

27:53The sun was setting into the ocean. It was great. That's one. Yeah. That's one night outside. And I think kind of keeping that connection to the human reality of what we're doing is really motivating. And part of why we like to, as often as we can, meet at a hip camp and see that in real life. Alyssa, what's the insight for other business leaders who don't have campsites in the core of their business for how to make an off-site or an on-site, how to tie it directly to the mission of the company and make it more impactful?

28:25I think a couple of things. One, just never undervaluing in-person time. Our company is a work-from-anywhere company. So for the most part, people get to be wherever they want. But we're very quick to pull the lever and say, we need an on-site. We're going to all get together in person. Maybe it's in San Francisco. Maybe it's at a hip camp. Maybe it's somewhere else. But being really quick to just get everyone together. There are certain problems that are just hard to solve through Zoom. So that's one thing. And then from the, you know, specifically camping angle, for us, that's our product. That's our mission. That's what we're building. I think any time you can bring your team to see firsthand and ideally experience firsthand what you're building, how that impacts people in the real world, that's a source of motivation.

29:03That's a source of energy and also a lot of intelligence, right? When you get to see it and feel it, you can see how to make it better as well. And so I think anything you can do to bring your team close to your customer, that's probably the core insight that we're tapping into there. Your passion just comes, like, right off of you. I mean, it just fills the room. And it's just a great reminder of what happens when you take on something that you really care about, where you are so deeply tied to the mission. We don't always get to sit with founders who are this excited about what they're trying to solve.

29:38I'm really excited. I'm very excited. And there's lots of layers to that, too, right? Like, I just love technology. I just, I find it endlessly fascinating. What do you love about it? I love that it's changing how culture works. I love that it's changing how people live their lives because that's an opportunity to improve things if it's harnessed properly. It's just such a force for change. You know, it's just fun. And then I love nature, right? I want people to get outside. The science around getting outside is completely clear now that it's so good for your health. I want rural communities and economies to be thriving.

30:08And I want us to protect and conserve all of the open land we have left. And so this is a model that allows me to do all those things at the same time. You know, there's nothing I'd rather be doing. I think of sometimes like coyote trickster energy. Like, how can we use technology to get people off of technology? Like, that's what we're doing. You have these moments in the evolution hip camp where they're inflection points, right? I have to imagine that much like for McKenzie at Mendocino Magic, there have been moments along the way where you have seen really concretely the financial impact that you're having on the landowners who are opening up their homes, their properties.

30:48And the positive effect that that's had.

Real World Impact on Landowners

30:51Is that right?

Real World Impact on Landowners

30:52Yeah.

Real World Impact on Landowners

30:53I mean, there's actually a very specific moment I can remember where that happened very concretely. It was super early on, probably our first few months of sending bookings to private landowners. And we were moving bookings. And I was, you know, really, it kind of felt like a scientist. I was like, is this going to work? It looks like it's going to work. And I reached out to one of our new hosts. It's a ranch up in Bodega, Northern California. And they were doing great. I was like, I'm going to go meet them. I'm going to go say hi, walk around the land. And I drive up to this ranch.

31:22It's called Salmon Creek Ranch. It's incredible. It's 600 acres of redwoods and a creek. Just incredible, incredible stewards. And I pull up and Leslie, the landowner, is waiting for me. And she's walking up to me and she has this piece of paper. And I'm like, oh, no. It's a list of demands. It's a list of complaints. It's everything we've done wrong. It's all the problems with the software, all the features we haven't built. So I'm sitting there. I'm like, hi, great to meet you. Feedback is a gift. I need it. Yeah, feedback is a piece. Yeah, feedback is a gift. What's with the paper? And she goes, I want you to have this.

31:52And she has it to me. She said, this is a letter from a financial buyer who sent us this letter trying to buy our land. And we get this letter all the time. They put it on nice paper. It's thick. And it essentially says, you know, we'd love to buy your land. We're going to develop it. You'd get a lot of money. You know, why are you trying so hard? Selling duck eggs. Why don't you just sell to us now? She said, I hate these letters. I hate them. If I, you know, this would be destroying everything we've dedicated.

32:23Our goal here is to leave this land better than we found it. This would be a failure. She said, but, you know, I've been having to hold on to them and put them in a drawer just in case because some months we're not sure exactly how it's going to work out. And I'm giving you this letter because Hip Camp makes it junk mail now. Wow. I know I don't need to call them back. I know I don't even need to save it. You can take it. Take it back with you. I don't need it. Because the income we're getting from camping, that's changed everything for us. And it's been amazing to hear that story again and again. I had another landowner who told me camping's changed this piece of land from a liability

32:55I was nervous to hand down to my son into an asset. Where does that Salmon Creek Ranch letter sit right now? Behind my desk. Oh, great. Yeah, I look at it every day. What a beautiful reminder of the impact you're making. Yeah, and how important it is to keep scaling it out too. Lisa, I noticed that you have some tattoos on your fingers. I do. Can you tell us about them, please? Yeah, so I have, these are the final words from the absolute last Whole Earth catalog. Are you familiar? I am familiar. Yeah, so this is stay hungry, stay foolish. And the, I guess, like kind of spirit of these words and why I got them,

33:29I got them actually after leaving my first job. And even though there was so much about that job that was so hard for me, deciding to leave, seeing what else was out there in the world, feeling that like rush of potential and creativity again, starting to have ideas for companies I could start on my own. That was what these words were meant to remind me of. And so I put them on my hand. So whenever I'm typing, I have to see them. But it's kind of like never settle, you know? And when you see those tattoos right now, what do they make you feel or make you think?

33:59Proud. Yeah, proud that I'm doing, you know, what I wanted to do. I'm taking the most powerful technologies and tools we have available to us and harnessing them for the impact I want to have. And with a lot of belief that with a great team, like we can do that. We can have that impact. Well, I'm so proud that we get to have you on Masters of Scale telling the story and using technology really to make people's lives better on both sides of your marketplace and give people the opportunity to use technology, to put technology away, connect with each other, connect with nature, and build better lives in a better country.

34:34It's wonderful having you on Masters of Scale. Thank you. Thanks for having me. Thanks again to Alyssa Rabassio for joining us. Alyssa is a stunning example of what's possible when you are hell-bent on solving a real-world problem as an amazing entrepreneur. I love how she's been able to prioritize the big ideas. I mean, the really big ideas, such as conserving nature and supporting rural communities alongside her goal for every single camper, which is very simply and quite beautifully more amazing nights outside.

35:07I'm Jeff Berman. Thank you for listening.

35:12Every business hits the same wall. The moment your business outgrows the systems that got you here. Spreadsheets everywhere, five different logins, data scattered across entities that don't even talk to each other. If your finance team spends more time finding data than using it, that's when you need the Intuit ERP. Intuit Enterprise Suite is the AI-native ERP solution that's powerful, painless, and proven, built for businesses scaling fast without the complexity that usually comes with it.

35:44From the makers of QuickBooks, learn more at intuit.com slash ERP.

35:52Humans will never be more intelligent than AI. There's going to be two types of companies. Those are great at AI and those that went out of business because they weren't. How do we build a future that is human-centered? I'm Rana Elkayubi, and on my podcast, Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone. Every week, I sit down with the pioneers shaping our future, and we take you behind the scenes

36:26of the AI that's transforming our lives. Find Pioneers of AI wherever you tune in.

36:59It takes about 10 seconds to find. Just search Rapid Response wherever you listen to podcasts, and hit follow to make sure you never miss an episode. I hope to see you there. Master's of Scale is a Wait What original. Our executive producer is Eve Trow. Senior supervising producer is Tricia Bobita. Associate producer is Masha Makatanina. Video editor is M.G. Frederick. Senior talent executive is Stephanie Stern. Mixing and mastering by the audio boys themselves, Aaron Bestinelli and Brian Pugh with original

37:34music by the remarkable Ryan Holiday. Visit mastersofscale.com to find the transcript for this episode and to subscribe to our newsletter and be sure to subscribe to our YouTube channel.

More from Masters of Scale

Reid Hoffman and OpenAI CFO Sarah Friar on where AI goes from here

Oct 22, 202628 min

REI’s secrets to sustaining a beloved brand and touching grass

Oct 20, 202628 min

Rich Roll’s ‘crash course’ in entrepreneurship

Oct 15, 202635 min

The AI race to save American science and reshape medicine forever

Oct 13, 202627 min

Pioneers of AI: OpenAI’s Tibo Sottiaux doesn’t want humans to be an ‘afterthought’

Oct 10, 202637 min