Building a marketplace from scratch

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ALYSSA RAVASIO: I really had a good understanding of scale and the internet, but then it was about combining that with nature and the outdoors. I did not have clarity on how we were going to make money or how we were going to build a company.

JEFF BERMAN: When did you know it was working?

RAVASIO: I remember waking up that morning and opening up our backend systems. I think we’d gotten four or five people to sign up at that point, and then there were hundreds. I got to scroll through, and I started crying.

BERMAN: I bet.

RAVASIO: Yeah, because you’re like, “Oh, people want this.” I would get really angry letters from people saying, “That’s the last place I could still go without six months’ notice.”

BERMAN: Oh, they were gatekeeping.

RAVASIO: They were gatekeeping, but it was also genuine scarcity.

The biggest challenge has been managing my own health and energy. 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. You’re way too young for shingles. Can we talk about your job? What’s going on?”

BERMAN: Because they knew this was stress-related.

RAVASIO: Absolutely.

BERMAN: With us today is Alyssa Ravasio, who is the founder and CEO of Hipcamp, which, if you are camping, is the way to book your spot, with, I think, over a half-million locations now and millions of trips booked. This is a really interesting scale story.

Welcome to Masters of Scale.

RAVASIO: Thank you for having me.

RAVASIO: Excited to be here.

Copy LinkWhy a broken booking system sparked Hipcamp

BERMAN: Thrilled to be here with you. Why this problem? Why was this the problem you wanted to take on?

RAVASIO: I was really lucky. My family went camping a bunch growing up. My childhood is filled with memories of making mudslides, catching frogs, and rekindling the fire in the morning from the little embers that were left over. That’s how I think of growing up. And 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, fragmented, and difficult that process was. At a moment when you can order any food, a car, or a hotel with the click of a phone, why does getting outside still feel like we’re in the ’80s? The idea was just to make it simple to get outside, in hopes that would get more people outside.

BERMAN: You started Hipcamp in 2013. Is that right?

RAVASIO: Yes, it’s been a little over a decade.

BERMAN: So it’s post-launch of Airbnb.

RAVASIO: Yeah.

BERMAN: If my math is right.

RAVASIO: Yeah.

BERMAN: Was part of it, “Let’s just do Airbnb for camping,” or did you have a different vision for what this would be?

RAVASIO: Yeah, it was a different vision to start. 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.

The fragmentation was really crazy. On this trip in particular, after planning for hours and choosing a campground, I found out once we arrived: We walked up to the campground, everyone had surfboards and wetsuits, and I was like, “What’s going on?” We walked out to the coast, and there was a beautiful surf break.

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.

BERMAN: Oh, you’re so bummed.

RAVASIO: I was so bummed. So the first version of Hipcamp, which was 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 what’s good to know about each campground. The first version of the problem was that I wanted to put the existing campgrounds on a map, and it actually took a few years until we realized the problem had a much deeper layer.

Copy LinkTurning founder frustration into company conviction

BERMAN: 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?

RAVASIO: I wanted it to be a business because I didn’t want to go get a job. I’d worked at a couple of start-ups before Hipcamp, and I’d learned a ton, but I’d also learned during that time that I really wanted to run my own company and be my own boss.

BERMAN: Can we click in on the couple of jobs that you had?

RAVASIO: Yeah.

BERMAN: What did you learn there that said to you, “This is not for me. I’m going to go start my own thing”?

RAVASIO: The biggest thing I learned is that when I figure something out, it’s really hard not to 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. Things like that really led me to decide, even though I was 23 at the time, that it was time to start a company. It was time to do things in the way that I thought would be best and feel 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.

BERMAN: Baller.

RAVASIO: Yeah.

RAVASIO: It was Spiral Films Production.

RAVASIO: We made movies. My sisters were my employees. I paid them in mac and cheese.

BERMAN: Awesome.

RAVASIO: Yeah, because I was the only one who could use the stove.

BERMAN: Right. Well, there you go. That’s leverage.

RAVASIO: 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. For me, it was about solving a problem that I thought was worth solving and worth the years and energy it would take to solve. I really had a good understanding of scale and the internet and how this new technology could totally change, and would totally change, how the world works. Then it was combining that with nature, the outdoors, and the passion I have for getting people to basically reconnect with the biosphere and nature. It was those two things together that made it worth going all in on.

Copy LinkLearning to code and finding early demand

BERMAN: How did you actually get Hipcamp off the ground? How were you financing it, and how did you get a website or an app in consumers’ hands?

RAVASIO: Yeah. Originally, I had to learn how to code. I had this idea, and I’d tried to start a couple of other start-ups, maybe at different moments in different parts of my life, and the big blocker was always finding a software engineer who wanted to build it. I found that it was just time to be able to do that on my own, so I went to DevBootcamp, which had just started at the time.

BERMAN: Right. This is before vibe coding.

RAVASIO: Oh, gosh. Yes.

RAVASIO: I don’t regret learning to code, but things would have been a lot faster if I’d had Codex. That would have been great, but I didn’t, so I learned how to code and ended up enlisting my sisters again, my first employees. And a couple of friends, actually, to build this very early version of the site that got some traffic and got people using it early on. We got traction. I think we were getting close to having one of the biggest search engines for camping.

BERMAN: How did you find those customers early? How did they find you?

RAVASIO: A little of everything. This was an era where I was going to every meetup I could. I would just walk around with my laptop, handing out stickers.

Big sticker fan. I brought stickers.

BERMAN: Nice.

RAVASIO: So I would 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 I’d open the laptop. “Do you see that place to put your email in? Put that in there. Oh, good. It’s working.” Big shoutout to REI on Brannan. They let me sit at a little card table I’d bring and set up in front of their door.

BERMAN: Wow.

RAVASIO: So I did a lot of that.

BERMAN: Really hand-to-hand marketing.

RAVASIO: Yeah.

BERMAN: Yeah.

RAVASIO: It wasn’t even just marketing. It was also feedback, right? It was also this idea that we’re going to build this product in collaboration with the community. I’m going to get input and understand what they’re looking for, what I have that they love, and what I don’t have yet. One of our big break moments was a digital version of that, where I got a customer support email from someone suggesting we add a filter for pets.

We were working on that, and I was like, “Great.” I wrote back right away: “Great, yes, thank you for your feedback. We’re working on that. I’ll let you know when we ship it.” Then suddenly I started getting traffic notifications from Google saying, “Your traffic’s spiking.” I was like, “What’s going on?” It turned out the person I had emailed back had a big Twitter following.

BERMAN: Wow.

RAVASIO: They liked my response, and they had tweeted out, “Go check out Hipcamp.” We got that first big traffic burst, and I got a bunch of emails. One of them was from Dave Morin, who ended up investing a quarter-million dollars later that month. It was kind of crazy, right? A customer support email led to a tweet, which led to our first funding round. And yeah, Dave’s been a great champion and partner ever since.

BERMAN: Well, I love that story about the customer feedback and your response because, one, it clearly shows a commitment to serving your community. But two, if you treat every customer, every community member, like a VIP, you just never know.

RAVASIO: Totally.

BERMAN: And —

RAVASIO: Zeus’s law, right?

Copy LinkWhen customer backlash revealed a supply problem

BERMAN: Right. OK, so you’re getting traction, you’re going, you’re building a real following, a real community, but you’re at this point really sort of a guide and a search engine. You’re not a marketplace.

RAVASIO: Right.

BERMAN: What happens?

RAVASIO: Crisis.

BERMAN: Never let a good one go to waste.

RAVASIO: No, I mean, it was existential at the time. Our mission from the beginning has been to get more people outside, and we really mean the more, right? We want people to connect with nature and get out there more often. We had this great search engine and directory, and we were getting lots of cool reviews. But what was happening was, every time I would find a campground that wasn’t fully booked and put it in an email or, God forbid, put it on the homepage, I would get really angry letters from people.

BERMAN: Why?

RAVASIO: “That’s the last place that I could still go without six months’ notice.”

BERMAN: Oh, they were gatekeeping.

RAVASIO: They were gatekeeping, but it was also genuine scarcity.

BERMAN: Yeah.

RAVASIO: I remember one email I got where someone was explaining, “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.”

BERMAN: Wow.

RAVASIO: I was like, “Oh my gosh. How are we going to make our mission happen if the existing infrastructure, in many cases, is already at capacity?” I’ll always remember this. I went to 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.

BERMAN: Especially North Beach.

RAVASIO: Yeah.

It’s like a big whiteboard at your table. I started writing down potential business models. Now, keep in mind, we’d 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 were we going to build a company? What was that going to be? Especially when all these people were so upset if we were marketing anything that wasn’t booked. We literally wrote down everything from advertising to a cool gear delivery service to private land.

Private land was a very niche idea. I’d gotten a couple of 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. I ran an exercise where I said, “If this business model was wildly successful 10 years from now, 20 years from now, what impact would we have had?”

It was only through that lens that private land jumped off the map, because we would have created a whole new way to get outside, changed outdoor recreation, and solved the root of the problem, right?

BERMAN: Yeah.

RAVASIO: The root of the problem was that there weren’t enough great campsites. There wasn’t enough supply. In doing so, we would have created this amazing model that could scale recreation for conservation. It was really through that lens that we chose private land. But I had a lot of question marks at the time. It wasn’t a sure thing at all.

BERMAN: Well, I love this for so many reasons, not least of which is that you had real customer feedback, which I think for a lot of entrepreneurs would have been exasperating. It’s like, “I’m trying to do good. I’m trying to provide a service here.”

RAVASIO: It was.

BERMAN: “I’m sorry it’s harshing your situation, but it’s a net good.” And really, what you realized was that there was a supply-demand problem.

RAVASIO: Yeah.

BERMAN: There was a different way to attack it. Can we just go back to this North Beach Italian restaurant? Were you there alone? Were you there with your team?

RAVASIO: I was there with my husband.

BERMAN: With your husband.

RAVASIO: Yeah.

BERMAN: Was it intentional? Were you thinking, “We’re going to go here and we’re going to work on this”?

RAVASIO: Yes.

BERMAN: Or was it…

RAVASIO: “We’re going to solve the problem tonight.”

BERMAN: Okay. Gotcha.

RAVASIO: A lot of intention.

BERMAN: With or without wine, definitely with red sauce.

RAVASIO: Definitely with wine, too.

BERMAN: 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?

RAVASIO: It was the start because, with a lot of business models, you ultimately end up helping people trade money for time.

BERMAN: Yeah.

RAVASIO: 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. It would solve the root cause.

BERMAN: Yeah.

RAVASIO: It could switch this system that’s in so much scarcity into abundance. Okay, that’s worth working on.

BERMAN: Yeah.

RAVASIO: Oh, and by the way, if it works, multi-billion-dollar company. Okay, I’ll go that direction. So it wasn’t until I looked at it through the longer-term lens that I saw the potential. But I think the real aha was the next morning. I emailed our entire user base, and I said, “I will give you five hundred dollars if you introduce me to a private landowner who lets people camp on their land.” And I got a lot of responses, so I spent the next week going and visiting places. One of the first ones I visited was called Mendocino Magic. It’s still on Hipcamp today. It’s an incredible spot. It has, I think, the largest private lake in the state of California.

BERMAN: Oh, wow.

RAVASIO: I was walking around this lake with Mackenzie, the landowner, and I just thought, “People would love to camp here.” 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 similar mission, and I looked around and said, “This is going to work. We can do this together.”

Copy LinkBuilding a marketplace around private land supply

BERMAN: How did you approach the scaling of the private land component of Hipcamp?

RAVASIO: We kind of used the existing public campgrounds, which were public data, as a way to bootstrap supply. We were like, “Ah, we have supply,” and then the demand showed up, right? As we added private land, it was really just about more supply, better supply. This supply you can book.

BERMAN: Yeah.

RAVASIO: This supply is beautiful and private. So it was pretty seamless, actually. And I think one of my other big learnings is most people want to camp somewhere beautiful and somewhere private.

Whether it’s managed by the Forest Service or California State Parks or Mackenzie, it’s all good. It started working pretty quickly. I think that’s one of the benefits of having the demand ready to go.

BERMAN: 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…

RAVASIO: Yeah.

BERMAN: On both sides here.

RAVASIO: Yeah.

BERMAN: How did you approach that?

RAVASIO: Getting insurance was one of the turning points for the company. We now have a really great general policy where all of our landowners are covered. We’re covered. There are all sorts of different layers to that. Before we had a policy like that, which we could share with our landowners, it was almost impossible to get anyone to sign up.

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BERMAN: 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?

RAVASIO: 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 a good alternative to a hotel or a house to rent. It’s just a different use case and a different brand. While there’s some overlap in customers, it really is a different way for people to think about what they’re looking to make happen in the world. So, of course, they could — not to tempt anyone here — but I think it would be very difficult and very hard. It would require different branding, a different setup, a different product, all of that.

BERMAN: Also, you’re at a scale now where the build-buy-partner analysis for Airbnb would be very different than it was then.

RAVASIO: Yes.

RAVASIO: Scale is the ultimate moat for a marketplace, right? Network effects are amazing, and it’s so fun to build a business. 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. That scale, that network effect, is what’s so exciting about the business model.

Copy LinkThe moment host demand proved the model

BERMAN: When did you know it was working?

RAVASIO: We partnered with a really large, I think, regenerative or organic farmers association.

RAVASIO: We had them email their newsletter and say, “Hey, if you want to host camping, sign up.” We didn’t know: Do people want to do this or not? I remember waking up that morning after they’d sent out the newsletter and opening up our backend systems. I think we’d gotten four or five people to sign up at that point, and then there were hundreds. I got to just scroll through, and I started crying.

BERMAN: I bet.

RAVASIO: Yeah, because 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. We’ve got the perfect…” I remember a strawberry farm on an island, and they were like, “But we couldn’t afford the insurance.”

BERMAN: Huh.

RAVASIO: “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. I knew we had demand. That’s never been the problem. Now we have supply.

BERMAN: What incredible signal. Will you situate us in the journey when this happens?

RAVASIO: It was probably 2017 or so.

BERMAN: Okay.

RAVASIO: Yeah.

Copy LinkNavigating regulation and protecting founder energy

BERMAN: What are some of the biggest challenges you’ve had to tackle that you didn’t foresee that night in your North Beach Italian restaurant?

RAVASIO: I think helping people think through infrastructure and the right thing is important. Probably regulations are another one.

BERMAN: Same one.

RAVASIO: Are you familiar with AB 518?

BERMAN: I am, because I prepped for our conversation.

RAVASIO: Okay. Just last year, California passed pretty amazing legislation that creates a new regulatory framework counties can opt into. It allows people who have bigger parcels, mostly targeting farmers, ranchers, land trusts, and things like that, to have up to nine campsites without needing to get the really onerous permit that is required for an RV park.

Before, there wasn’t a separate lane for these lower-impact types of campsites. That has totally changed the game. It’s been amazing to see the coalition around this. It’s everyone from the Farm Bureau to the Nature Conservancy. When’s the last time all the farmers, all the conservationists, and all the small rural businesses agreed on something? Outdoor recreation is such a powerful economic engine. 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. That’s really created, I think, a groundswell of support around regulations to better support more outdoor recreation.

BERMAN: Alyssa, what’s been the biggest challenge since you incorporated private land and Hipcamp really took off?

RAVASIO: I think, for me personally, the biggest challenge has been managing my own health and energy.

BERMAN: Say more. Why is that?

RAVASIO: I’m a pretty obsessive person, and very passionate, and I believe so much in what we’re doing that it can get really easy, especially 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. These little things, each one on its own, feels justified in the moment, but over the course of a few years it 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. You’re way too young for shingles. Can we talk about your job? What’s going on?”

BERMAN: Because they knew this was stress-related.

RAVASIO: Absolutely.

BERMAN: Yeah.

RAVASIO: Absolutely. I think learning to build the right systems and the right habits is important. There’s no glory in becoming unhealthy in pursuit of this mission. I’d say the real unlock is knowing that your body and mind are worth taking care of, and that if you’re really solving a problem and building a scaled organization that’s going to help shape culture for decades, you’ve got to take care of yourself. You are worth taking care of. So many times, I’ll talk to early-stage founders who are 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 against a challenge, and instead of getting curious about how to get around it, it feels like drama and stress. It feels like it’s the end. I think that’s actually probably been the hardest part of all of this for me.

BERMAN: How big is the company now?

RAVASIO: Close to a hundred.

BERMAN: A hundred people?

RAVASIO: Yeah. We’re now the largest search engine for public land. We’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 that all the existing campgrounds can also 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. It’s really those three pillars together that have created the Hipcamp of today.

BERMAN: Alyssa, is the company remote, hybrid, or in person?

RAVASIO: 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.

BERMAN: How do you do in person?

RAVASIO: 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.

BERMAN: So you do on-sites at campsites?

RAVASIO: Sometimes, yes.

BERMAN: And what do those look like?

RAVASIO: Generally, it’s like we’ve identified a really important problem. There are 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 till we do.”

BERMAN: And it’s one thing to bring everyone into an office.

It’s another thing to bring everyone to Mendocino Magic or 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?

RAVASIO: I think for us, being at a Hipcamp 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 we create more great campsites. Our number one objective has been, for a long time, to actually get to go walk the land. So recently we had an onsite out in Stinson.

We got to walk around Slide Ranch, which is a beautiful Hipcamp and nonprofit that has a mission to get more kids rooted in nature. They have great campsites, and they use that revenue to fund scholarships. We got to walk around, hear from the host about those scholarships, and 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. Then we got to walk through the campsite and see the people who were setting up their tents and were going to camp on the edge of the Pacific Ocean for the night. 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 our core company North Star, it’s nights outside, right? That’s our core KPI we’re always tracking and working toward. When you get to the millions, it can start to feel abstract. Then getting to walk by a campsite and see, I did this just last night, a mom with her son setting up, 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. The sun was setting into the ocean. It was great. That’s one night outside.

BERMAN: Yeah, it was an eclipse.

RAVASIO: That’s one night outside.

BERMAN: Yeah.

RAVASIO: I think 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 Hipcamp and see that in real life.

Copy LinkBringing teams closer to mission and customers

BERMAN: Alyssa, what’s the insight for other business leaders who don’t have campsites at the core of their business? How do you make an off-site or an onsite, tie it directly to the mission of the company, and make it more impactful?

RAVASIO: I think a couple things. One, 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 onsite. We’re going to all get together in person. Maybe it’s in San Francisco, maybe it’s at a Hipcamp, 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. Then from the 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, that’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. 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.

BERMAN: Your passion just comes right off of you.

RAVASIO: Yeah.

BERMAN: 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.

RAVASIO: Thanks.

BERMAN: We don’t always get to sit with founders who are this excited about what they’re trying to solve.

RAVASIO: I’m really excited.

BERMAN: It’s awesome.

RAVASIO: I’m very excited. And there are lots of layers to that, too, right? I just love technology. I find it endlessly fascinating.

BERMAN: What do you love about it?

RAVASIO: 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 such a force for change. 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, and I want us to protect and conserve all of the open land we have left. So this is a model that allows me to do all those things at the same time. There’s nothing I’d rather be doing. I think of it sometimes as coyote trickster energy: how can we use technology to get people off of technology? That’s what we’re doing.

BERMAN: You have these moments in the evolution of Hipcamp where there are inflection points, right? I have to imagine that, much like for Mackenzie 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, and the positive effect that that’s had. Is that right?

RAVASIO: Yeah. There’s actually a very specific moment I can remember where that happened very concretely. It was super early on, probably in our first few months of sending bookings to private landowners. We were moving bookings, and I really 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 want to go say hi, walk around the land.”

I drive up to this ranch. It’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. 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 like, “Hi, great to meet you.”

BERMAN: Feedback is a gift.

RAVASIO: I mean, yeah, feedback’s a gift. What’s with the paper? And she goes, “I want you to have this.” And she hands 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, ‘We would love to buy your land. We’re going to develop it. You’d get a lot of money. 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. This would be destroying everything we’ve dedicated ourselves to. Our goal here is to leave this land better than we found it. This would be a failure.”

She said, “But I’ve been having to hold onto 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 Hipcamp makes it junk mail now.”

BERMAN: Wow.

RAVASIO: “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.” 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 I was nervous to hand down to my son into an asset.”

BERMAN: Where does that Salmon Creek Ranch letter sit right now?

RAVASIO: Behind my desk.

BERMAN: Oh, great.

RAVASIO: Yeah, I look at it every day.

BERMAN: What a beautiful reminder of the impact you’re making.

RAVASIO: Yeah. And how important it is to keep scaling it out, too.

BERMAN: Alyssa, I noticed that you have some tattoos on your fingers.

RAVASIO: I do.

BERMAN: Can you tell us about them, please?

RAVASIO: Yeah. These are the final words from the absolute last Whole Earth Catalog. Are you familiar?

BERMAN: I am familiar.

RAVASIO: Yeah. This is, “Stay hungry, stay foolish.” The spirit of these words, and why I got them, is that I got them after leaving my first job. 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, and feeling that 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. So I put them on my hand so whenever I’m typing, I have to see them. It’s kind of like, “Never settle.”

BERMAN: And when you see those tattoos right now, what do they make you feel or think?

RAVASIO: Proud. Yeah, proud that I’m doing 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, with a lot of belief that with a great team, we can do that. We can have that impact.

BERMAN: I’m so proud that we get to have you on Masters of Scale telling this story and using technology to make people’s lives better on both sides of your marketplace, and to give people the opportunity to use technology to put technology away, connect with each other, connect with nature, and build better lives and a better country. It’s wonderful having you on Masters of Scale.

RAVASIO: Thank you. Thanks for having me.