Outdoorsy Co-Founder Lived With Her Customers for Outreach | Leveling Up (Ep. 2.2)

So today we're going into Outdoorsy, which is a ride-sharing marketplace for RVs. So let's go in and learn their story. When you started the business, you know, when we talked about it before, you didn't just decide to start it and it wasn't just an idea. You actually did a lot of legwork around it. I think a lot of people don't understand how much goes into, like, what you put into it to build this thing. So can you talk about that story?

Yeah, absolutely. And I'm glad you brought it up because I I think a lot of entrepreneurs and young people can be enamored by some of the tech success stories and they think it could be a little bit more simple or easy. But it's really important to focus on your customers and all of the stakeholders in your market. So for us, what we did was we sold our houses and we actually bought a trailer. We bought an Airstream, we bought a Denali truck, and we moved into it. Burn the ships. Yeah, exactly. It was a commitment, but it was definitely worth it. We hit the road and we lived in an RV and we lived in RV parks for just about 8 So we made sure we talked to like hundreds of people and of all different types. So we talked to people renting RVs, people that owned RVs, the owners of RV parks. We asked people to tell us what were the things that mattered. If you were going to rent an RV, would you want one-click checkout to include your insurance and roadside assistance? We talked about the details of what you needed to provide and communicating the difference between a towable and a motorhome.

How'd you know what to ask?

You know what, we just started off by asking, kind of like this, this, you know, this format here. It's a conversation. You just have to get in and you've got to know more and you've got to ask more questions to be able to find the features that really matter and to be able to find the elements of where you're actually addressing a need. Because I think a lot of good businesses are solving a problem that exists. So you've got to be able to talk to everybody and identify what that problem is, and then you can go about setting and building out the product.

Google the keyword customer development. You have to do customer development. Jen just went hardcore on it to sell your homes and actually do it for 8 months. That's hardcore. That's actually the most in-depth I've ever heard of before in my life. For those of you building out software, it's probably a little easier for you, but you have to do customer development or else you're gonna be screwed. So what are some struggles you faced while growing this business? And you started in, was it 2012?

No, we started— so the idea first came to us, or the concept first developed in 2014.

Okay, 2014.

We launched the site in 2015, and we did a significant pivot in 2015, going from focusing on the consumer marketplace to focusing on professionals. And the professional side of the marketplace. And so this year really makes our very first calendar year for business, and it's done really well.

Got it. And so why did you decide to make that pivot?

Right, so that's a great question, especially I think for entrepreneurs. What we found in marketplaces, and we went through an incubator called NFX, which was just a fabulous place to be able to start incubating our idea and really figuring out what were the important things for driving growth in the business. And one of the things that came out through that whole process is that a lot of marketplaces are initially massively successful because they professionalize the marketplace. So, you know that the concept may solve a need or address a problem before, and you know you've got a large total addressable market.

Mm-hmm.

But in order to really get it off the ground, you need to work with the people that are really serious, that have done this work before. And in our case, professional RV rental companies and/or people that had small rental businesses, they were the guys that were out there, and the girls that were out there, really focusing on, you know, building, you know, building out their inventory and finding trailers that were popular and people wanted to rent, making sure the whole customer experience was already bedded down in terms of what needed to be included, how the vehicle needed to be cleaned, pickup and drop-off, the key exchange moments. So, what we did was we pivoted from just focusing on the consumer marketplace to working with pros and saying, hey, what extra features do you want in your software? Do you want to be able to Show breakdowns in like your revenue? Do you want to be able to have, you know, one-click insurance options in your checkout process? So we worked with them, we figured out what software they were looking for, and then we focused on building out the software and the needs for the professional side of the marketplace first. And that gave us the fastest path to actually getting a product that was soup to nuts, professional grade.

So it sounds like, you know, you went into a little bit and then the data told you that these customers were probably the better ones to work with in terms of growing the business faster.

Yes. also in terms of learning the most from what makes sort of the best, like, consumer experience for us. So that was our big pivot. So then we, we brand— we built out that product called Wheelbase, and we message and we market it slightly differently. We focused on that. That was our first big pivot. And once we, once we hit the big milestones on that side in terms of signing on all of the big RV rental companies in the United States focused in, big huge states like Arizona and Texas and Florida and California. Then we came back to center and started to build out the private RV owner and the consumer marketplace.

You know, I think the third takeaway is making sure that you set some kind of ideal client profile. You start to understand more data around your business. Now, I do want to back up a second to maybe get a story about a time where you struggled a lot starting this business or getting to where you're at right now. So it sounds like the pivot was one of them, but is there anything else that sticks out?

building a startup is a constant struggle. I mean, that's part of the culture of startups, right? In order to be successful, you've got to 100% commit to speed. And if you're committing to speed, then you are going to constantly struggle every day. Because what it means is you're going to throw up landing pages, you're going to try out new product features, you're going to build, you know, prototypes for potentially the wrong customer group. But the point is, you're out there and you're throwing up work and you're seeing if it actually sticks and if it's what you need to continue to invest in. So mistakes, in most cases, 80% to 90% of those decisions will not be the right ones. So you're constantly living in this like environment of like failing or making mistakes or not finding the right way and struggling.

Mm-hmm.

But I think the big point there is to just know that that's the culture that makes a really great startup in terms of migrating it to a good mature business. And we still do that today. We still trial out programs and features and a lot of elements that don't necessarily hit the ball out of the ballpark for us, but it's just the way we operate.

So what are some numbers you can share around Outdoorsy?

The most exciting number for me just in this calendar year is that Outdoorsy will have booked over a quarter of a million nights booked on the platform. Wow.

And that's in—

Hundreds of thousands. That's just in 2017. Wow.

Okay.

This year. Which I think is a really great nod, obviously, to the platform being the perfect solution for both renters and owners, solving a need, and also addressing that there's, you know, big demand out there for people wanting to be able to rent RVs and take more experience-based trips and travel. You know, in our world, you take your hotel with you.

That's a good— that's a good line. You should definitely use that in ads. I want to go back to the story where you, where you burned the ships and you and your partner basically said, okay, let's sell the house. Let's, let's move out, let's go out on our own and do this. You know, what was going through your mind emotionally? I mean, how were you feeling about this?

You know, it's funny because now when I look back on it, I'm so much more terrified about what we did than when we were in the moment. And I bet a lot of entrepreneurs probably feel the same way. We were so passionate about this idea because we had the basic, you know, total addressable market numbers, and we did the basic math, and we thought there is a market here and there is a problem that technology and software hasn't solved. Plus, we knew— I felt in my heart that there was a really passionate community, and you need to have that as well to be successful in, obviously, marketplaces. So we had all of those things there, and I think it's just a little bit of just commitment and hard work and maybe a little dose of ego, like, we can do this, we can do this. And I remember back in those days, it was— that's all it was about. I mean, we eat breathed and slept outdoorsy and road travel. We still do that now. I'm not gonna lie, we still do that. But back then, when you're building something, that's what you obsess about is how to build it and how to get the right insights and how to get it going. Now I look back on those period— that period of time and I'm like, we must have been crazy.

Mm-hmm.

We sold our houses, we moved into a trailer, we, we just crisscrossed all of these streets and we had conversations and we were building something. Without any 100% guarantee that it was going to be a huge business, which we needed it to be to justify obviously complete change in our lives and direction.

That's nuts. So I'm imagining, okay, like for me, I sell my house, I move out, but so what is, what is your day-to-day change into? What did it morph into?

What were you doing?

We did a combination. So what we tried to do is not spend all of our time driving, because the bottom line is even when you're doing user testing and you're trying to get insights from your consumers and your users, that can take up a lot of time and you have to be really careful about making sure that you're spending the right amount of time talking and pulling the insights you need, but the right amount of time also building something, getting it out on the internet, testing it, trialing it, see if it sticks, see if people wanna use it. So we tried to— and we got a lot better at it as the months went on that we were on the road— but we tried to develop good conversations on the road, focus groups, then build out a prototype, get it going, get some insights, go back and test out some more work. So we tried to split our time. At the very beginning, it was probably 50/50 driving and parks and just absorbing everything we needed to. And then towards the end of the 8 months, it was a lot of just like, you know, power up in the trailer and just like, you know, fingers bleeding on the keyboard every day.

Wow, that was incredible. What a cool story. I love Jen. I love her story. And if you're a business owner, you're trying to level up your business, watch this episode again, or even better, go to the next episode in the playlist. If you enjoyed this video, make sure you subscribe, leave some comments, let us know what you thought. If you like this, if you were inspired and you want to go out and start your business, go for it, and we'll see you on the other side. Take care.