I recently went one on one with Jeff Cavins, the founder and CEO of Outdoorsy. Outdoorsy is the largest recreational vehicle and outdoor travel marketplace in the world, with millions of rental days and nearly a million users, operating in fourteen countries. Jeff is a technology veteran who was involved in designing and developing the instant replay system in the NFL . 

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Jeff: Some might be surprised to learn that I’m not really just a business guy, although my bio might convince you otherwise. I’m actually an engineer at heart. When I get into any new business, I immediately start to see problems. The biggest thing I’ve ever learned in my career is you always look for the “bleeding from the neck” problem — the thing that’s just killing customers and consumers. And then you tackle it head on. So my career has been a series of roles at completely different kinds of companies where I’ve uncovered problems and worked to find innovative solutions to them.

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas?

Jeff: My co-founder, Jen Young, and I have been inseparable for years, in business and life. In a board meeting one day, we decided that it was time to get away from life surrounded by four walls, spent under the glow of fluorescent lights. We sold our homes, moved into an Airstream towed by a Denali truck, and spent the next nine months traveling across the U.S. We were on a fact-finding mission to learn about the RV lifestyle from travelers we met at campgrounds, coffee shops, gas stations, music festivals and the like — and over 1,200 interviews later, we concluded that there was demand and a business opportunity out there on the road.

From that point on, Jen and I left our long-standing careers so we could do something purposeful and fun. We spoke to our network of friends and families about this desire to build a marketplace that revolved around our passion for road travel and being outside and that’s how Outdoorsy was born. 

Even before the birth of Outdoorsy, Jen and I were outdoor enthusiasts and loved disconnecting from our busy lives to hit the beach or spend time in the mountains. Leaning into this love for time spent outdoors was the catalyst to getting Outdoorsy off the ground and promoting the wellness benefits tied to getting outside and disconnecting from our day-to-day confines continues to be the backbone of our business today. 

Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea?

Jeff: It would be remiss of me if I were to say that we were successful from the get-go. We hustled our butts off and, quite literally, hit the ground running. We uprooted our lives, moved into an Airstream and traveled across the U.S. to talk to everyone and anyone who was willing to talk to us. We made over 1,200 personal phone calls to RV owners we found on Craigslist and we walked up to campers, knocked on their doors and sat with them hours interviewing to learn as much as we could. We talked to them about our concept and listened to their feedback and what their pain points were. After speaking to countless travelers in the RV community, we began to see a trend, a growing consumer movement, of people from all over the world who were craving more accessibility, affordability, and unique experiences in the outdoors. 

Initially, investors balked at our idea for Outdoorsy — we quite literally got laughed out of a few meetings — so we funded the business ourselves in the beginning. That gave us a lot of control to build out our vision and, eventually, attract the attention of investors.

Adam: What are the key steps you’ve taken to grow your business? What advice do you have for others on how to take their businesses to the next level?

Jeff: Back in 2014 when we first had the idea for Outdoorsy, we were eager to share our vision with friends who would listen and investors who would take a meeting. No matter how much we finessed our pitch or how short and sweet we made our spiel, we were repeatedly met with disinterest. Some critics called Outdoorsy a "small market opportunity." I would go pitch a VC and they would cut the meeting short. Usually they give you about an hour to do your pitch, but they were cutting me short at about 15 minutes. They called it an “unintelligent idea.” I had one guy stop the meeting right as I was clicking to Slide 2 on my presentation deck and he goes, “What? You’re doing a marketplace for RVs? That’s ridiculous. Any business that’s old, male, and stale, we want nothing to do with.” That’s what he called it — old, male, and stale.

They claimed that the majority of people didn’t like to travel in vehicles. They argued that road travel was a forgotten past time, and emphasized that a concept revolving around road travel didn't stand a chance at becoming a successful online marketplace. “No one will care,” one person told me. “There will be no users and no activity. There will be nothing but crickets chirping on your website.” 

It’s been five years since we heard those initial discouraging words about our new business idea. In that time, Outdoorsy has welcomed more than 100 million visitors to its website and iOS app, booked more than 3 million days of vacation travel, and our mobile-first platform is now live in fourteen countries including the U.S. and Canada. Since the launch of our platform in 2015, we’ve booked more than $890M in gross sales through the website and mobile app. Despite the initial outside skepticism, it’s clear our instincts about the opportunity were correct!

When investors shut doors on us in the beginning of our fundraising efforts, we went back to the drawing board. We didn’t give up hope. Instead, we decided to bootstrap the company to get it off the ground and brought on two additional co-founders. We made the decision early on to invest in trust and safety because people are giving us their children, their families, their pets and we always need to make sure they are safe and protected. Our first brand value at Outdoorsy is to put the customer ahead of ourselves and our second is to do the right thing and make long-term progress in the world. So any new product launch or feature enhancement starts with us thinking about the customer first — What do they need? What are they asking for? Where are there still pain points in their customer journey and user experience? 

At the end of the day, the relationship you establish with the customer is the investment that matters most. The more you meet with customers and get in front of your audience, the clearer your next steps as a leader and as a business will become and you’ll start to develop more confidence in your concept. 

Adam: What are your best sales and marketing tips?

Jeff:  Listen, listen and listen. And keep moving. Talk to your new, potential and existing customers and listen to what they have to say. Learn from their advice and experiences, and don’t take anything personally. 

Startups are well poised to adapt to change from situations like COVID since they can typically move faster — and run tests more frequently — than larger companies. Whether you are a new company or a well established one, open and honest communication with your customers is critical.

Don’t let perfection get in your way. We’re living in a rapidly changing environment that is completely different from one week to the next, so it’s important to be nimble and flexible.

Think about where you go to learn about something new — let’s say it’s a new restaurant. Is your first step to go try the restaurant or to look at photos of it on Instagram, to read reviews of what people have said on Yelp and TripAdvisor? Always think how the customer would think and meet them where they’re looking for info. We’re always looking for ways to reach new customers who may not know about us yet. 

With an influx of new consumers — RV renters and owners — discovering Outdoorsy through our website and the App Store, equipping them with easy and engaging educational resources will always be crucial to our success and that’s one area we’re constantly innovating and investing in. 

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Jeff: As cliche as it sounds, check your ego at the door. Learn and accept that you’re not the expert in everything — trust and enable your team to teach you and bring their best expertise to the table. 

Adam: What is your best advice on building, leading and managing teams?

Jeff: Your first key hires are going to be the foundation of your organization's staffing strategy, so you want to ensure you hire people who are great leaders and that have talent that follow them. You need to identify mental athletes that have an appetite for solving what they do not know and grow stronger in their pursuit of collaborative excellence. Money isn’t the only factor and will come to those who work with a passion and a purpose. At Outdoorsy, we are bringing diversely different people together in a forum that helps us realize our humanity and strive to be better people. To us, that’s a mission worth fighting for.  

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Jeff: 

1. Having a vision and being excited about something is not enough. Typically people build a solution, looking for a problem to solve. But the best way to understand if you’re going to have something that’s successful is to go find a problem — one that people might not know they have — and then go build the solution. And if you believe in something, make sure you test it, and make sure it’s solving something. 

2. The biggest influence I had in business was my father.  One of the biggest lessons he taught me: It’s never too soon to make the right decision and you’ll realize that, when you do, you’ll wish you did it sooner. You have to be swift and decisive. Your company counts on you for that. 

3. It’s human nature to be negative. Prove the naysayers wrong, but never gloat. You never want to be an arrogant winner — it’s very unbecoming. Even if you’re right, it’s important to be a very gracious winner. 

Adam: What is the single best piece of advice you have ever received?

Jeff: My dad always said, “Show me a good loser and I’ll show you a loser.” Losing should never be something you’re really good at. We’re all going to lose in business, but what that means is you when you lose, you want it to hurt. You want to learn something from the loss.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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