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Robin Thurston is an energetic person who began life in sports. First as a skier, and then as a professional bike racer who competed internationally before switching to business after a major accident. His rise in the business world has been plutonic ever since, carrying lessons from each part of his life to build better. His venture, Outside has raised more than $180M from top-tier investors like Sequoia Heritage, Jazz Venture Partners, Zone 5 Ventures, and Next Ventures.

In this episode, you will learn:

  • How to segue from sports to business
  • The value of teamwork in reaching company goals
  • How to take advantage of new platforms for success
  • How to adapt to new roles and work in a team
  • Robin’s book recommendation
  • His top advice before starting a company

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    About Robin Thurston:

    Robin Thurston is the CEO of Outside.

    Outside’s diverse, premier active lifestyle brands and products share a singular mission: inspire people to do the sports and activities they love.

    Outside is the place all types of active lifestyle participants call home. Outside partners with our communities at every stage of their journey by creating the world’s most personalized experience. Content, Experiences, Utilities, Community, and Commerce that improves knowledge, training, nutrition, events, and motivation by understanding our customers better than any other platform in the world.

    Our 38 brands are the active lifestyle industry’s most trusted sources for event news, training tips, nutritional plans, event experiences, travel, and trusted gear recommendations. Our brand leaders thrive on educating readers and sharing authentic stories to help inspire them each and every day.

    We are the world’s leader in the active lifestyle category across Content, Experiences, Utilities, Community, and Commerce but we are just getting started.

    Before joining Outside (previously Pocket Outdoor Media), he ran a consumer genetics company called Helix in Silicon Valley before returning to his home state of Colorado. Prior to Helix, Robin co-founded and built MapMyFitness into one of the world’s largest open fitness tracking platforms.

    Following the acquisition of MapMyFitness by Under Armour, he joined the innovative sports apparel organization and served as Chief Digital Officer, where he led the overall strategic direction of the company’s Connected Fitness and eCommerce business.

    Robin spent the first ten years of his career building a mutual fund classification and rating platform at Lipper (a Thomson Reuters Company), as well as a risk and compensation platform at both American Century Investments and Wellington Management.

    He graduated with an MS in Finance from the University of Colorado at Denver and lives with his wife and three children in Boulder, Co. He is a lifelong cyclist who started riding and racing in the early 1980s.

    Specialties: Leadership, Entrepreneurship, Product Management and Development, Interactive Marketing, Financial Modeling, and Statistical Analysis.

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    Connect with Robin Thurston:

    Read the Full Transcription of the Interview:

    Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we have a really incredible entrepreneur. I think that we’re going to be learning a lot from his journey, a lot from adversities, especially with some of the ones that he had to face as a professional cyclist. I don’t want to make you guys wait any longer, so without further ado, let’s welcome our guest today. Robin Thurston, welcome to the show.

    Robin Thurston: Thank you for having me.

    Alejandro: Originally born in Denver, Colorado. How was life growing up there?

    Robin Thurston: It was good. I would say that I spent so much time away, I always found myself wanting to get back. So now that I’m back in Boulder, I’m very happy to be here. I was fortunate to grow up here, I think.

    Alejandro: You were growing up there on a bicycle. That’s how you were raised, so tell us about the upbringings of being on a bicycle.

    Robin Thurston: I was fortunate. We had this program when we were in school, where they would take you up skiing, so I got into skiing very young. We had a fairly warm winter one year, and a friend of mine convinced me to get a bicycle. We had an event here in Colorado called the Red Zinger Mini Classic. I was nine years old when I first competed in that and was fortunate that I did well. Some people took notice and said that maybe instead of ski racing, I should be a bike racer. So I got into cycling very early. I feel like it has crafted and shaped my entire path and my life. So many people that I know and so many of the experiences I have had have been on the bicycle.

    Alejandro: Eventually, you become a professional cyclist. You go to Europe. During one of those times, there’s literally one event where you were jumping off of a cliff. What is that? What happened?

    Robin Thurston: [Laughter] I had many crash events, but there was one in France, where I was following—there were five or six guys off the front. I was maybe the third or fourth guy back. I was following them down this hairpin sort of cliff. You give so much trust in the person in front of you in cycling that you’re literally following their wheel. One of the riders just went straight off the cliff, as if they just didn’t hit their brakes at all, and there was no guard rail or anything. I followed him right off the side of the cliff and fell probably 20 to 30 feet. I got very fortunate. I fell into a big grassy patch. He did not get so lucky. I’m actually not sure what happened to him. I know he broke his hip and had a pretty bad concussion at the time. I was fortunate. I crawled back up on top, and I finished the race, and then I passed out at the finish because I had a sharp rock hit my elbow. I had about 45 stitches in my elbow, but I had lost a lot of blood over the last 30 to 40k of the race. I passed out when I was up on stage. You know, funny events like that—I had another one when I went through the back windshield of a team car, which I would say was the ending of my career. I say, look, I was a good cyclist. I wouldn’t say I was one of the greats, and I think that was the realization for me at the time. I had been racing for 15 years and frankly was tired and had some of these things happen to me. Yet, I say that serendipity drew me back to the U.S. I went back to school for finance and was able to create a new path and a new career, which, unfortunately, many cyclists have a hard time making that transition. I was at the right time, the right place, and I got a job with my first startup, which was a company called Lipper, which was acquired by Reuter. It was all serendipitous timing.

    Alejandro: One quick thing here before shifting gears to the next chapters in your career is that in cycling, the team effort and the strategies are really big deals. How have you gone about applying some of those learnings to building and scaling teams?

    Robin Thurston: Most people don’t realize about cycling how big of a team sport it is, but I think, for me, if you think about the roles that there are on the teams—yes when you think about something like the Tour de France, or you think about something like the Giro, there’s a definitive leader. But the truth is that you get opportunities as an individual rider on the team sometimes. If you’re in some of the strongest riders where there might be a specific stage or a specific individual day of racing where the team gives you the ability. That’s something that I certainly have learned in building my teams is that sometimes, it isn’t about how much spotlight is shown on you; it’s a lot about giving people opportunities on your team to shine in certain situations. The other thing I would say is camaraderie. When you spend years and years in vans and busses with your teammates, you learn that celebrating and that time and connectivity that you have together is a lot about what builds the team and allows you to operate in these very stressful situations. For me, I think we tried to do that. I often say we don’t celebrate the wins enough. I think that’s true of so many entrepreneurs, but I try to raise up and reward people in our teams when they do well because I think those are rare opportunities to build that camaraderie on the team.

    Alejandro: As you were saying, you were lucky to shift gears. You got your degree. You went to work for different companies. Eventually, here you are in Europe. You find yourself having some drinks or lunch with some friends, and then a very interesting conversation sparked what became your first baby as a company. Tell us about that discussion, and how things came about, and the sequence of events toward bringing your first company to life.

    Robin Thurston: It goes back to these moments of being on the bike and being with people that really understood that journey. I was in a small town in Switzerland called Andermatt on this cycling trip with some Americans and some Europeans. Literally, one night at dinner, somebody said, “It would be cool if I knew the roads that you know here in Switzerland without your being here.” That kicked off the idea for MapMyFitness, MapMyRide, MapMyRun, MapMyHike, and all of those sites. I knew there were travel books. I knew there were places where you could get these routes, and you can look for certain things, but they weren’t personalized. It wasn’t like you, and I know each other, and I make a route for you, specifically, because I know what type of cyclist you are and maybe where you want to go. Or you tell me you’re going to Switzerland, and I could send you something. I happened to be working on a project where I was working with a very early version of Google Maps API. I thought, “I wonder if I could use that to build this mapping tool?” We kicked off the project. I met my co-founder, Kevin Callahan, who was living in San Diego. He was an engineer from Johns Hopkins. We got together, brainstormed, and came up with how we were going to put this whole thing together. I thought it was going to be a small lifestyle business. I didn’t actually think at the time that it was going to become something that big until the app store launched, and we were fortunate enough to build two of the first hundred iPhone apps with MapMyRun and MapMyRide. By November of 2008, when the markets were melting down, we had AT&T featuring us in those full-page ads because they were the exclusive iPhone partner in the U.S. We had them featuring us as one of the apps on all of the advertising nationally. I don’t want to say the rest was history, but man, it was a sharp up and to the right curve. The downloads exploded. We were seeing usage across the board. Obviously, the use case and the product/market fit were really good. I left my finance job. We didn’t take funding in 2009. We kept building the company because we had about $3 million in revenue. Then Austin Ventures, down in Austin, approached me. We took a Series A from them. We moved the business, the largest portion of it, to Austin. In 2013, out of the blue, Kevin Plank called me from Under Armour and was like, “What are you doing with the company?” I said, “I’m trying to build a big digital sports brand.” We had about 20 users there, and we were doing about $20 million in revenue—mostly advertising, some subscription, a little bit of B2B, SaaS platform, development for healthcare companies. Kevin was like, “Come see me.” I met with Kevin, and 90 days later, Under Armour acquired us. It was a really quick deal and a really great outcome for the shareholders and for the employees. Then I stuck around at Under Armour for three years.

    Alejandro: Why do you think it was the right time to sell at that point?

    Robin Thurston: It’s always easy in retrospect, as you know, to look back and say, “We should have held onto that for another five years. Look what we could have done.” But I think there were two things for me: 1) the competition in the market, there was a lot of it in terms of the number of running apps and cycling apps and things of that nature. I really felt Under Armour gave us a chance to build something bigger. We really wanted to add on commerce as a big piece of what we were doing. While they were a single brand with a single eCommerce site, we felt they were a really good marriage. Then the other thing I would say is I thought about the user data, and I felt like Under Armour was very authentic in terms of how they were thinking about it. They were going to use the data to sell people better and more product. I thought the users would understand that. Let’s say we had sold the company to a healthcare company. I don’t know that they would have understood it as well what we were doing with it.

    Alejandro: Yeah. What was the amount that was reported?

    Robin Thurston: This was $150 million to Under Armour.

    Alejandro: Got it. I’m sure that at that point, you were able to be in a position to buy any bike that you wanted.
    [Laughter]

    Robin Thurston: Yeah. That’s for sure.

    Alejandro: I’m sure it was life-changing, so good stuff. At this point, you become the Chief Digital Officer of Under Armour. I’m sure that was quite a shift because here you go from building your company, going full-motion, speed ahead, and now you are part of a big organization, which moves at a different type of speed. So how was that adjustment for you?

    Robin Thurston: As you said, Kevin Plank and Under Armour changed my life, and I feel tremendous loyalty to Kevin and the team. I love sports. I’m not just a cyclist. I’m a huge football fan, soccer, Formula 1, basketball. For me, going to Under Armour was like being a little kid in a candy store. It was everything I possibly—my first month there, I was at the Super Bowl and a boxing match in Vegas. I went to the National Championship in College Football. It was a really unbelievable time to be there, and the brand certainly was on fire when I first got there. The stock was at a peak. That whole time and the comradery that the team had, I felt was really incredible, and frankly, was a unique situation for me. Sometimes, as a newcomer inside of an organization like that, it can be really hard, but I felt like everybody, from Kip Fulks to Kevin to Henry Stafford, all welcomed me into the group. It was certainly a big deal. And, as well, they needed a digital strategy. That’s what we put together. We bought a total of eight other companies. We put them all together under Connected Fitness and unified that to grow the eCommerce business. It was a venue for us to be able to do that, and frankly, it really worked out. I think the connected fitness strategy was the right one. They’ve made some significant changes since then, but at least by the time I had left in June of 2016, I felt it was the right strategy for the company.

    Alejandro: In this case, you decide to leave. You ended up running another consumer company. But in this moment during this journey is where you find a segue to launch your next thing, which ended up being acquiring companies during COVID. You did like ten acquisitions during COVID. Why don’t you tell us about this latest baby that you are working on and what was that process of coming up with the concept and executing on it?

    Robin Thurston: What I would call Outside 2.0, we acquired Outside Magazine and Outside Television, and we rebranded the companies when we acquired them to Outside. When we started, my view is what has been missing from the healthy lifestyle category or the active lifestyle category is what I would call the true definitive home of this person. Where do they go every day, not just to find inspiration and training and things like that? But where do they go to take action to register for the next event or where they’re going to travel to next, or what gear they’re going to buy? There wasn’t just one place where all of those things came together. When we started, I would say it was a little bit more modest than that. We started in the endurance category. We were able to acquire the first brands, Triathlete Magazine, VeloNews, Women’s Running, and PodiumRunner, back from a competitor group that sold to Ironman. They own the Rock ‘n’ Roll series marathons. We own some cycling events in Colorado, and we started building this personalization platform that would unify that experience. But we knew from the previous data at Under Armour that 60% of the audience did at least three activities a year, and over the course of a lifetime, this year you might run and ski and do a little bit of yoga; next year, you might switch and say, “I’m going to ride my bike more. I’m going to start doing some hiking. I’m going to do some other activity.” You might totally change the picture of what you’re doing. There isn’t anyone that’s evolving with you that’s saying, “This is great what you’re doing now. Here’s everything you need to do that.” But how do we guide you toward the next thing you’re going to do. People change activities for all kinds of reasons. You might have a friend who says, “I don’t really like to run. Do you want to ride a bike with me?” And you’re like, “Sure. I’m going to give that a shot.” Or you might have a group of friends going on a big hiking adventure. You go do that, and after that, you’re really into hiking. There’s a whole number of reasons why people switch from category to category, but we wanted to build a place that wasn’t just for one activity, but it was about thinking about how you can participate and activate in all of those categories, and also, as we think about lifetime value because we are very focused on membership. Our new membership is called Outside Plus. We’re focused on that membership because we want to evolve with you and not have a lifetime value of our membership of a year or two years. We literally want to be with you for your lifetime as you ebb and flow through that journey.

    Alejandro: How much capital have you guys raised to date for Outside?

    Robin Thurston: A little bit over $180 million.

    Alejandro: Got it. Now, as you’re thinking about what’s going to be the future and what’s in store for Outside, if you were to go to sleep tonight, and you wake up in a world where the vision of Outside is fully realized, what does that world look like?

    Robin Thurston: The thing I would say about the active lifestyle category is, you will go through a lot of friction because you are so engaged. I take a category like healthcare, and you build these incredible applications for people, and they don’t really use them that much. I think that’s really a bummer. Whereas, in the active lifestyle category, people will put up with so much friction to register for an event, or to buy a piece of gear, or to find the content that they’re looking for in the training side. My future vision is that all of this stuff is much easier for the consumer and that it’s helping guide their next decision. Think about how good a job Netflix does in putting the right content in front of you through AI as you go and watch one program after the next. They understand that here’s what they might want to watch next. Amazingly, when you pull it up, you’re like, “Yeah. That’s super interesting. How do they do that?” Well, that doesn’t exist in the world of active lifestyle. My view is, it’s all user-driven, and there is a lot of friction. The future state world, to me, is it’s not just about you self-discovering gear and content and events; it’s how do we drive and put the stuff in front of you in real-time that matters and will drive you to go do that activity because we fundamentally believe the world is a better place if people are more active and outdoor doing the things that they love to do. We want to make sure that flywheel is going at a future state is where that’s all happening very automatically, and you are inspired to do more and more activities because it’s so seamless for you as a user.

    Alejandro: As you’re now executing on Outside, what is something that you experienced with MapMyFitness when you were building the business that was a lesson that you absolutely knew that you were going to apply to Outside?

    Robin Thurston: First, I would say the investment—we being Outside, in my view, we are a product and technology company first. Secondarily, we’re trying to build the absolute best and most authentic content and services that plug into that platform. I think my experience at MapMy is that in some ways, I feel like we lost at times, maybe because we didn’t build the best product in the market. I think we had a great product, but I don’t think we necessarily had the best product. It was because we didn’t invest in much in engineering, design, product management as we should have. I think, here, one lesson is we are overinvesting in that area to build this very holistic, personalized product for the consumer because we absolutely believe it will resonate with them over time. The other thing I would say is how you take care of your team and think about diversity are things that I think we did okay at MapMy, but that we could have done a lot better. I would say I’m hyper-focused on building the greatest team and the most diverse team so that we ultimately can get the benefit of what that means from an organizational perspective.

    Alejandro: To expand on this, imagine that I put you into a time machine, and I bring you back in time to that moment where you literally were stepping up from the conversation at that restaurant in Switzerland. There you were, thinking about launching a business. Imagine that you were able to grab that younger Robin and say, “Hold on a minute.” And with all the knowledge and everything that you know today, you’re able to give yourself one piece of business advice before launching MapMyFitness. What would that have been, and why based on what you know now?

    Robin Thurston: I would have grabbed that person and said, overinvest in your team, whether that’s the type of people that you invested your time in hiring. The diversity of the team that we would have hired and how well you treat them from everything from compensation to equity to other benefits. I really would have said to do more because I think the outcome might have been different. I’m not saying it was a bad outcome. It was a great outcome, and I’m certainly very happy with where MapMy ended up. But I think it would have been a different outcome.

    Alejandro: Got it. In terms of books, what would you say is a book that you wish you would have read earlier?

    Robin Thurston: It’s funny. I’m reading a book right now called Product-Led SEO by Eli Schwartz. I read half of it this weekend, and it’s an extraordinary book. I would have read that earlier because one of the things we did not invest enough in was essentially what I call product development on the SEO side for MapMyFitness. It took us a long time. Once we got it right, we started getting an enormous amount of traffic from that very early, sort of mid-way through building the company, and I wish it would have been earlier. I’m trying to think of another book that I absolutely believe every entrepreneur should read. I’m big on this idea that you really have to motivate your team. If you don’t work on motivating your team, you simply aren’t going to get there. I know there are a lot of books that try to inspire you around motivating your team, but I think it has to come from you. It has to be really organic. You have to believe in what you are building in order for your team to respond to that, and then you have to make sure that you’re telling them. Any books in my mind that help the entrepreneur do that are going to ultimately help you craft a better story and message for your team.

    Alejandro: That’s amazing. Yeah, I think without motivation, having that alignment, and having the team with a sense of ownership is quite tough to achieve great things. Robin, for the people that are listening, what is the best way for them to reach out and say hi?

    Robin Thurston: LinkedIn is a great place. I would say I always respond to people on my LinkedIn profile. I certainly try to respond on Twitter as a secondary. I use Facebook and Instagram more for my personal stuff, so not a great way. I don’t do a lot of direct messaging on those channels, but those are probably the two easiest ways to get a hold of me are Twitter and LinkedIn.

    Alejandro: Amazing. Robin, thank you so much for being on the DealMakers show today.

    Robin Thurston: Hey, my pleasure. Thanks for having me.

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