Mark Gainey, Strava Co-Founder on Entrepreneurship, Life and Sport

Like many of the things born in Silicon Valley, you might say Strava, the favorite app of millions of athletes, is a happy accident. Strava’s co-founder Mark Gainey, set to run cross-country as a freshman at Harvard in 1986, was sidelined by an injury. This led him to the crew team, where a junior rower named Michael Horvath took him under his wing.

Fast-forward three decades, and Mark and Michael have been at the center of two of the internet’s big eras as friends and business partners. Still in their 20s when they founded Kana Communications in 1996, they saw the first dot-com boom up close as Kana’s valuation hit north of $10 billion in 2000.  

Then, in 2008, their passion for sports came full circle with the launch of Strava. It’s one of the few apps still featured on the home screen of my phone years after downloading it.

Mark Gainey and I met a few years ago, when a good friend heard me rambling about my latest fitness idea and said there was someone I needed to meet. Grounded and patient, I learned firsthand that Mark is one of those people you instantly want to work with.

Prokit co-founder and CEO David Swain (@swain) sat down with Mark at his home to discuss his journey. Our conservation has been edited for brevity. 

Disclosure: Swain was an active Strava board advisor at the time of this interview.

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Growing Up in the Biggest Little City in the World

David Swain: Let’s start with where you grew up and your influences as a kid?

Mark Gainey: Born in Denver, Colorado, but raised in Reno, Nevada. My dad was a general surgeon. My mom was a stay-at-home mom. I was the oldest of three. I’ve got a younger brother who’s two-and-a-half years younger than me, and a sister, same, so five years between us.

Reno’s one of those funny places. It’s called the “Biggest Little City in the World.” I used to joke there are two cities there. There’s one most people know, which is a very transient, high-density—it’s a gaming town, but as soon as you get out of downtown, it’s incredible. Reno, for anybody who likes the outdoors, starting in first grade, we had PE at the local ski resort. They’d bus us off to Mt. Rose Ski Resort, and we’d ski all winter long. In order to verify the traveller’s identity online, they proposed a video identification system that automatically verifies electronic and physical security features of identity documents. This ID verification software combined with biometric identification allows to ensure that the traveller is entitled to book a flight.

My first summer jobs were at Lake Tahoe pumping gas and grinding the bottoms of boats at a local marina. For a kid who enjoyed being outdoors and playing soccer up until high school, when I switched over to cross country, it was a fantastic place.

What drew your parents to Reno?

It was Dad’s job. He had an opportunity to come out with a partner and take over someone’s practice. Both of my parents grew up in the Bay Area. My dad’s a San Francisco native, born and raised in the city, and my mom was on the Peninsula. Dad did his residency in Denver, and I think they fell in love with the Rockies, and so the opportunity to be in the mountains, but closer to family, was compelling. They’re still in Reno. They love it.

How long did your father work?

Well, he’s 82 years old. I really don’t have a primary care physician, so thankfully, my dad still takes my calls. He was in private practice into his early 60s. Then he had a really interesting career where he left his private practice, but went to work at the Veterans Administration, where he became much more of a mentor instructor. In Nevada, the VA is where a lot of the medical students get their training and do their residencies. He’s got very funny stories about moving into that mentor role, and about working with the vets. I think it was a great way for him to end his career.

Did you have extended family in the area?

We’d come and visit extended family here in the Bay Area, but no, we were a close-knit family. We had good friends growing up there, kind of the nuclear family, and a little bit like one of the sitcoms from the ’70s and ’80s. We lived that, and it was pretty good.

Your love for sports and the outdoors—did your parents pass that down to you?

Less so, but it’s not that my parents weren’t active. They were just willing to invest in our activities. Whether it was making sure we could join the local ski program early on, or supporting my love for soccer as a kid, and traveling all over the West Coast, they were always behind me.

When I graduated from high school, the graduation gift was a mountain bike. My parents gave me a great choice. This was 1986. I could go to Australia to watch Dennis Conner regain the America’s Cup, or I could have a mountain bike. To this day, I’m not really sure why I chose one and not the other, but I did, and no regrets. I had a Ritchey Ascent mountain bike from 1986. It was a beautiful machine.

Is your 1986 Ritchey still in the garage?

No, it was stolen here on the Peninsula. It was chained to a fence, and I went off to work. When I came home, it was gone. To this day, I check eBay and other places looking for a vintage Ritchey to get back to my roots.

What got you into competitive sports in high school?

Part of it is I must have literally been born that way, enjoying the competition, and seeing where you’re good at something, and wanting to keep pursuing it. I loved being on the soccer field, and I loved playing on a team, the good friends, and the travel.

Through soccer came running. I was pretty good during the soccer warm-ups when we were running laps. I’d be the guy at the front running those laps. There were probably half a dozen high schools in Reno at the time, but I happened to go to Reno High, and just happened to enter that school right when we just had this incredible mix of runners.

I was there my sophomore year through senior year, and we won the state championship as a team all three years. Most of my competition was on my own team, so when you’re living that six days a week, and you’re literally racing in practice, it makes it pretty easy to go out and win races. That was what drove me, but I think it was also the great coaches, Ray Hays and Peter Duffy. They inspired us and were good runners in their own right. And just being surrounded by a bunch of other guys who, frankly, on any given day, could kick my butt.

Do you keep in touch with any of your running teammates?

I’ve lost touch with most of the guys. One was in my wedding years ago, and so we’ve stayed close. Ironically, it’s through Strava that I have more interaction with him. We’ll give Kudos to each other on a fairly frequent basis. After graduating college in 1990, there was a brief period when I was back in Reno trying to figure out what to do next. It was pretty clear it was going to be hard for me to build a career there, so I left Reno. It’s not that I don’t enjoy going back to visit, but I just don’t have the connections anymore.

An Unexpected Detour

Talk about your journey from Reno to Harvard.

It’s funny, full disclosure, I was not applying to Harvard when I was in high school. What happened was a very nice coach sent me a handwritten note in the fall—it would’ve been fall of 1985. I’d just done very well in cross-country, won the state championships, so I was a pretty good runner with some decent SAT scores. Nothing to write home about—by no means a perfect score, but good. He wrote this note saying, Hey, we saw your results. Have you ever considered Harvard? I’d love to introduce you to our program.

I laughed. I said, “No way am I going to go, this kid from Reno, not even an interest.” It was my father who was like, “You do not have to go. You don’t have to get in, but you’re going to be a decent person, and you’re going to reply to this. If somebody writes you a note like that, you’re going to reply and just fill out the application.” I did, and lo and behold, I got in, and visited, and figured, What the heck? It was worth a shot.

Did you run in college?

I was recruited to run cross country and showed up with a stress fracture, so I was unable to run my freshman year. Then, in the process I got recruited by the crew coaches. They were pretty clever back then, and would recruit from the other athletic programs. At that point, it was a pretty easy choice, just the opportunity to be in that boathouse with a national-caliber team, and to learn a new sport.

Have you read Boys in the Boat? That’s my only experience with rowing, but it was impressive.

I’ve got Boys in the Boat on my bedside table. The one I always recommend is called The Amateurs by David Halberstam. Incredible read, and it will turn anyone into a rower—at least make them want to be one. I understand Boys in the Boat’s the same.

What did you study?

Technically, my degree says “General Studies.” I had enough credits in art history—fine arts is what they call it at Harvard. I started as a history major, but found art history was a great way for me to learn history. Don’t take me to the museum. Don’t ask me to identify an artist. I can’t do that, but it’s a great way to learn about history through the eyes of an artist at the time. That was the academic side of it.

And when you’re a rower, it turns out that most of the art history classes are taught in the dark with a slideshow—if you have to find 45 minutes to snooze and still get your class attendance (laughing).

My degree should say “Crew” because that’s where I spent the vast majority of my time. I am being sincere: I can’t begin to tell you how valuable that experience was, from the friendships that have become lifelong business partnerships. We’ll talk about Michael Horvath, I’m sure. He’s been my business partner for 25 years.

Talk about what you learned in crew that you’ve applied in life.  

Michael was class of ’88. I was ’90. That particular group from the class of ’88 really took me under their wing, and I became great friends with a number of guys there.

There was just an intense work ethic that’s hard to describe. At one point somebody did the calculations—the number of hours we put in training for the few minutes that we actually raced in the spring season, because these were 2,000 meters long and six-minute races. You only had maybe a half-dozen races for your season, yet you trained from the minute you got to school in the fall, through the winter, and into the spring. You had to do it other than just to race, and really appreciate the journey.

“There’s a fine line between perfection and disaster, and you can apply all these things later on.”

The teamwork. Everybody thinks of rowing as somewhat of an individual sport, but you have to figure out how to mix in effectively with eight other people—seven other rowers and a coxswain. When you have that right, there’s no more powerful feeling. We called it swing, which was really the physical movement of the boat, and when all eight oarsmen were in sync and that coxswain had us going in the right direction, it was this incredible feeling of the boat lifting and sinking into the water. There just isn’t anything like it. When it’s off, it’s miserable. You get injured. People get thrown out of the boat, which is called crabs, or you injure your hands on the oar. There’s a fine line between perfection and disaster, and you can apply all these things later on.

From Dialing for Deals, to Becoming a Dot-Com Hit

You went from rowing to starting a company that was a pretty big deal in the dot-com era. How did that happen?

There’s an important sequencing. As I was graduating, I had not applied for any jobs. I wasn’t thinking about working. I wanted to continue rowing lightweights (there are lightweights and heavyweights in rowing). Lightweights had just been added to the Olympics, and the first opportunity was going to be in ’92, I think, in Barcelona. I had dreams of, Could I make one of those lightweight teams? I had a great coach, a guy named Charlie Butt at Harvard, who now has the whole program.

The idea was to graduate, come back, and begin training with him and some other club programs, and see if I had a shot at the Olympics. Murphy’s Law, I was home for two weeks after graduation, and I blew out my back on a rowing machine in Reno, in the middle of the desert.

That led to a nine-month period—a little bit of a reckoning—because it was not at all clear that I was going to be able to come back to rowing. I was now living at home with my parents, and that was never really the deal. You’re going to graduate from Harvard with a degree, and you should go off and find your adult life. They were kind enough to let me figure that out. Pretty quickly, it was clear I wasn’t going to be rowing again, and I needed to move on to a new chapter.

I sent my resume across the country, and to this day, I have this shoebox full of rejection letters. I have this funny way of keeping all the rejections in my life, whether it’s venture firms who turn us down, or people who never gave me jobs. It keeps me humble. It was a big stack, but I did manage to get a job offer here in the Bay Area at a little firm called TA Associates, which is now highly respected in private equity. I was hired to dial for deals, to basically call entrepreneurs looking for investment opportunities. They had a very unique model in that they always found established, entrepreneur-owned, growing, profitable businesses—the exact opposite of what you actually find in Silicon Valley.

I’d show up on a Monday morning with 50 newspapers on my desk. This was pre-internet, so I’d get all these newspapers, and I’d pull all the want ads out of the Sunday papers from around the country. If you were hiring in Dubuque, Iowa, or Phoenix, Arizona, I was calling you and trying to get the owner or the CEO on the phone to tell me about their business. I did that for almost five years.

It was a great job. I like to joke that I got paid to go to business school because I’d basically get case studies all day long talking to these guys. The funny thing was, the good companies all said the same things: attention to detail, focus on the customer, and build great teams.

Did you get any good wins through this?

Oh, I got a couple wins and a couple where we should have won, but didn’t. The firm did very well. Probably very few people would know of the ones I was involved with, firms likes Ontrack and Diamond, which were in the video space.

I had one of the best calls and visits we ever had. I got on the phone and called Jim Jannard, the founder of Oakley Sunglasses. He started telling me his story, and to this day—he doesn’t even know this—he is one of my key mentors in life.

What we learned from him over a two- or three-month period were a lot of the lessons I just told you about from crew. The grit and determination and persistence. I often refer to them now as the three P’s: patience, persistence, and perspective. Jim had this amazing story. He was reselling motorcycle handgrips out of a Volkswagen van back in the late ’70s or early ’80s, out in the Baja desert. He saw all these guys coming in on their motorcycles with cracked goggles, and he was like, “There’s got to be a better way.” Long story short, he ended up with this amazing business that, at the time we talked to him, had better margins than a software company.

That business was minting money, but Jim did it by bringing everything in-house. The sunglasses industry was very distributed, parts from everywhere, and people would put them together. Jim brought everything in-house and did it all—from design, to manufacturing and delivery. He was maniacal about the quality, maniacal about his distribution. Even when I knew what it cost to manufacture a pair of sunglasses, at the time I had no problem paying these exorbitant rates for a pair of sunglasses because they were that good. It was a great product.

Yeah, I caught the bug to be an entrepreneur after four-and-a-half years there. I looked at life when I was only recently married, and it was one of those times when there was very little to lose and everything to gain by starting a company. Worst-case scenario, I’d have a good story for a business school application. Best case, I’d start something that would sustain my family, which was the mission, just enough to put food on the table and pay the rent.

That was late ’95, so that’s right as Netscape was going public and that first wave of internet companies was starting to surface.

It was around that time you launched Kana. Was it you and Michael from the beginning?

Michael’s trajectory was a little different. He graduated in ’88 and studied economics. He went off and got his PhD from Northwestern, and ended up here in the Bay Area as a professor of macroeconomics at Stanford. He was teaching while I was working at TA Associates.

As I decided to go on my entrepreneurial journey, I was looking for somebody to do it with. You and I’ve talked about how lonely entrepreneurship can become, so I was looking for a partner, a co-founder. There are a number of guys I tried to recruit who did not pull the trigger. They were probably wise, but they didn’t do it. Michael was willing to sit with me and spend time on this.

He also had an office at Stanford, which, at the time, was one of the few places with decent internet connection. I used to joke, the reason he’s my partner is because he had great internet connection. He was such a good partner because he was the yin to my yang. You’re not going to meet a more ethical person. You’re not going to meet a person who’s more humble, who works harder, and he also just understands things about business that, frankly, I don’t. That worked out really well.

This was ’95. When we started Kana, he stayed in academia. He was busy raising a family. He and Anna had four children in a pretty short period of time, and then he found himself, largely for family reasons, leaving the Bay Area, staying in academia, and ultimately ending up in Hanover, New Hampshire, where he taught entrepreneurship at the business school at Dartmouth. But he was always my co-founder and engaged at Kana.

What was that like for you, still in your 20s, to watch a company grow that quickly?

When I left Kana in the summer of 2000, we had about 1,200 employees and a market cap north of $10 billion on the NASDAQ. It was good business. We were generating hundreds of millions in revenue, but yeah, it was also during that period—the first dot-com boom was pretty unique.

What did you learn during that period?

The power of team. I talked about how much fun I had on the crew team at Harvard. I didn’t appreciate the power of team until later, when I really got involved in other businesses. I was incredibly fortunate for the people willing to come and join me on the ride. This wasn’t just Michael, my co-founder. Paul Holland ran sales for us. He’s now a partner at Foundation Capital and has been very successful there. Michael Wolf ran engineering for us and is a world-class entrepreneur. He’s had two major wins since Kana.

I could keep going. Guys like Bill Felch, who ran services, and others who were really a critical group that happened to come together and bond over the vision of what we were trying to do—that’s what makes or breaks any company. I don’t care whether it’s a software business, or you’re manufacturing paperclips, or soccer balls, or running a restaurant. It’s all about the people you bring together. I was really lucky that group was willing to come together when it did.

Thinking about the people was a huge takeaway as we built Strava. We take a lot of time to bring people on board, but I think it pays dividends.

Going Full Circle with Strava

Going back to the three P’s, when I met you one of the things I noticed was the word patience. Your patience and deliberateness while building the Strava brand and community are unique. Where did that come from?

We face a constant tension at Strava around this. I understand the need to move fast and to be willing to break things—to not seek out perfection. Side note: The three P’s used to include perfection. It used to be patience, persistence, and perfection, but I realized perfection was leading to a bunch of bad behavior we didn’t want, so we threw it out. We do want to experiment. We want to fail fast, so perspective was all about keeping things in perspective as we try to move forward. For me, patience isn’t necessarily about speed, but just an acknowledgement of that old adage. The best things in life, they don’t come easy. They come hard.

“Our vision was always to support the global community of athletes, regardless of what sport they’re in. There’s a universal language, and there’s a universal set of needs that all athletes have.”

With Strava, to this day, sometimes I’ll hear, “Oh, the clever little cycling company.” You can go look at our early business plans. We had a go-to-market strategy that said we were going to focus somewhat maniacally on the cycling community, but don’t confuse go-to-market with vision. Our vision was always to support the global community of athletes, regardless of what sport they’re in. There’s a universal language, and there’s a universal set of needs that all athletes have. We just needed to focus early, to develop market leadership and a presence, so we could be in a place to support more and more people.

We took a lot of cues from the grand brands Michael and I admired, and set out to see if we could go do something similar. Those are not brands that were built overnight. In fact, a key takeaway from the dot-com era, internet 1.0, is from this funny phrase: “Oh, yeah, what a rocket ship.” I used to remind everybody, “Yeah, and what happens to rocket ships once they run out of fuel? The trajectory tends to be straight up and straight down.” So in Strava’s case, at the risk of not going fast enough, if you can build a trajectory that feels sustainable over a long period of time, you end up at the same altitude, but now you’ve got incredible lasting value.

One of the other things I’ve heard you talk about with Strava is authenticity. Would you elaborate on that?

That word gets used a lot, and I know it can be abused. At Strava, we’ve literally put it on a coin. Authenticity is one of the five core values inside the business. There’s an A, a B, and three C’s, and the A stands for authenticity. It comes from a simple thesis—let’s go build for our customer. If you’re clear on who your customer is, and you can understand their needs, even if you’re a raw startup, you can be successful.

I’ll take it all the way back to my days working at TA Associates. There were two key takeaways:

1. Pursue things you’re genuinely interested in. Ironically, this came from the entrepreneurs—the theory being that you’re going to be doing this 24/7, 365 days a year, so it might as well be something you are genuinely passionate about. Otherwise it’s a really hard slog. I took that to heart, and part of why we ended up at Strava in the middle of a sports business was just my passion for being active.
2. Solve real problems. The partners I worked for, even though they were venture investors and not entrepreneurs, gave me another piece of really important advice, which was to solve real problems. In some ways I would equate this to authenticity in business. If you can solve the real problem regardless of your size, your scope, and your sustainability, people will listen.

You can go back to our roots around serving cyclists to see how that authenticity surfaced. Michael and I, neither of us are particularly good cyclists. That’s not our background, and so you heard running, and rowing, and so forth.

I love to ride my bikes. I love to ride in the dirt, but by going out and talking to the cycling community, we found we could be very focused. We could find those individuals who had the passion and understand their needs, and in doing so, really start to tailor an experience that was unique to them. In Strava, that manifests itself in everything from taking care of things like power and wattage—which is this whole language that very few people are familiar with, but for cyclists is really important—to things like identifying climbs automatically, because it turns out cyclists love climbs. Cyclists know every hill and every grade they’re on. Building that into the experience was about being authentic with them.

Did you have a core group of early users giving you feedback?

We did. I can name the very first guy who was ever on Strava. His name was David Belden, the commercial customer, and he’s still here in the Valley. I believe he still works at Google. He’s a great guy.

We have tens of millions of people on Strava today. I think we add a million people every 30 to 40 days, but I remember the first 10 that we put on Strava, and the first 15, and the first 20. They were buddies that had worked with me at Kana, friends in the venture community, a bunch of cyclists in the venture community. If we could find a cyclist willing to listen to the story and willing to experiment, then we would bring them on.

There was a great piece of advice I got long ago from a Harvard classmate. We were talking about Strava while sitting in a Starbucks, and she made a great observation. She said, “I talk to way too many entrepreneurs who, when I ask them about who their customer is, they say, ‘Well, look, here. Anybody sitting in this Starbucks could be a potential customer.’” I mean, the beauty is anybody who would have a need. She called this the Starbucks phenomenon.

I had the exact opposite. When she asked me, “Well, who’s your customer?” I said, “See those four guys sitting over there in Lycra with their bikes parked outside the window? That’s my customer.” And her eyes lit up because she said that kind of focus—now I could go have a conversation with them. Whereas, if you try to have a conversation with every person inside a Starbucks, you’re going to get 75 different responses to something. That authenticity is pretty critical for the early stages.

You’ve been through a couple startups. You’ve got two sons. What do you do to stay grounded?

I’m probably the worst person to answer this question because this is where I’d say I am definitely not successful. I’ve had my own strategies. I think my balance has come in huge chunks. I tend to obsess in some ways in one area. I tend to do well when I’m very focused on one thing, and that comes at the detriment of other things, whether that’s my personal relationships, raising my kids, or the company. So I tend to focus on one thing, but I know I can only do it for x-period of time. That’s been my strategy.

I admire some of the other entrepreneurs I’ve studied who have figured out a way to be much more balanced on a regular basis.

That being said, starting Kana and Strava were two different experiences. When I was with Kana, I was newly married. My wife Lisa came from an entrepreneurial family in her own right, so she felt like she knew what she was getting into. I don’t think either of us expected that Kana was going to do what it did, and it became all-consuming, but it was just the two of us, and there weren’t kids involved. I didn’t have a lot of other obligations then. I wasn’t sitting on seven other boards, so it was manageable.

Fast-forward to Strava, and it’s a very different situation. I was a single parent with two boys who were seven or eight years old at the time we were starting. Theoretically, I was pretty confident I could manage my single-parent duties along with the startup. The problem is with time you forget all the bad, and you only remember the good. I’d forgotten just how hard startups are and how all-consuming they can be. Strava did that. Strava took over again.

The thing I refer to now—the boys will even joke with me, I call it SOB disease. It used to be KOB disease. Now it’s SOB disease. It’s “Strava on the Brain,” and many an evening when I’d be sitting there with the boys at dinner, or trying to have a conversation, and I’m asking them about their day, they tell me how their day has gone, and I can’t hear them. I own that.

One of the things I decided at Strava was, we see a business we think is only scratching the surface, and we want to keep doing it for the next 20 years. Something I needed to personally change was leadership. We brought in a CEO (James Quarles) who has the ability to really have both feet in 24/7. This has afforded me the luxury, frankly, of being present for Jake and Charlie.

What are some of the traditions and habits you’ve brought to your boys?

I got a compliment just yesterday. My boys met somebody else who happened to be associated with Strava. This was a Saturday afternoon, and the gentleman said afterward, “Boy, they each shook my hand like they meant it and looked me in the eye.” That was good, because I can say it came directly from my father.

We spend a lot of time talking about personal passions. I got to be a kid in Reno. I remember spending afternoons on my little BMX bike, or with a soccer ball, with a football, and playing with other kids. Kids don’t get to do that as much anymore. We spend a lot of time at the house talking about, “What are your interests? How can I help support those interests?”

Frankly, as sophomores in high school, my sons are starting to talk about college. We try to get away from the college discussion and more around, “Let’s figure out what you’re interested in, and that’ll lead to whatever the next chapter is.” I think I owe that, again, to my parents. They weren’t necessarily athletes, but they allowed me to pursue that passion. What I saw in my father as a surgeon was somebody who was incredibly dedicated to his patients, to his work. You never saw him complain about having to get up at 3 a.m. and take care of somebody. That was just the job. Hopefully some of that stuff’s rubbing off.

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