Cycling Legend, Investor, and Podcaster - Lance Armstrong

Let me give a brief introduction about Lance. He started cycling at the age of 15, and ended up in the Olympics very, very early on. He began gaining popularity and then immediately got cancer, which left him out for a period of time. Then he came back, and created the Livestrong Foundation, which was against cancer and raised up to $500 million. And then he came back and won seven Tour de France, which is probably the most grueling event in the world among all sports. Not once, but seven times! And then, in his words, “fell from grace and went from hero to zero”, came back and invested in companies like Uber and DocuSign. Became one of the best investors around the world, and also started one of the most successful podcasts out there. Most importantly, he has a family of five. So, welcome Lance. Let’s get to the origin story. How did you get into sports?

I was born in Dallas but grew up in Plano, Texas. I was raised by my mom who was a single parent, she was only 17 when she had me. And as a Texas kid, I tried the usual sports like football, baseball, and basketball but I had no potential. Anything requiring side-to-side or fast-twitch movements just wasn’t for me. Despite the social pressure, I just wasn’t meant for those sports. I told my mom that I wanted to quit all those sports. She agreed but insisted I choose one sport to stick with. I had friends on the swim team, so I picked swimming, even though I didn’t know how to swim properly. They started me with the younger kids. At the time, I was 12 learning with these 6, 7 year olds at the left most side of the pool and my friends on the other end. It was a bit embarrassing, but I didn’t quit. I loved it and gradually improved, and really, swimming was my first true love. That was my entree to endurance sports and serious training. If you’ve swum competitively, you know what it’s like. Early morning workouts at 5:30 before school and sessions after school, totaling up to 10,000-12,000 yards a day. By age 15, I placed third in Texas in the 1,000 free. I also ran track and cross-country in high school, which led me to triathlons. I got a bike, and the rest is history.

So, your first sport wasn’t cycling. It wasn’t the typical “I started at five years old” story. Yours was like the third if you consider triathlon that has the part of that. Can we talk about your path to cycling and your early Olympic experiences? How did you make it to Barcelona, and what was that like?

My dream was to be an Olympic triathlete, but triathlons didn’t become an Olympic sport until 2000 in Sydney. In the late ‘80s and early ‘90s, I realized I’d have to switch to cycling to reach my Olympic goal. In 1990, I began competing full-time as a cyclist and made the 1992 Olympic team in Barcelona. At the time, the Olympics were primarily for amateur athletes, except for basketball with the Dream Team. Everybody else was amateur athletes. In 1990, competing as an amateur was the highlight of my early career. It was the ultimate. For the professionals, especially in our sport, I don't want to say it's an afterthought or a secondary goal, but the Tour de France reigns so supreme in cycling that if you gave all of those guys, the opportunity to pick between winning an Olympic medal or winning a couple of stages in the Tour de France, the Tour is still the granddaddy.

What did you do when you found out you had cancer? I believe it was a bit later than that. Did your sponsors drop you?

I was diagnosed in 1996, about a month after the Atlanta Olympics. Back then, we didn’t have easy access to information like today. We relied on pamphlets from doctor’s offices or bookstores. It was a scary, confusing time. I had testicular cancer that spread to my brain. It was serious. Cycling is a team sport, so sponsors usually back the team, not individual riders. I couldn’t find a team willing to take me except for the American team sponsored by the U.S. Postal Service. It was my last option, but we built it into a great team, and it was my shot. In the end, it worked out.

Can you paint a picture of why the Tour de France was so difficult? And what is the setup for a team to compete?

The Tour is three weeks long with only two rest days. In our generation, it was about 2,500 miles but now it has gotten shorter around 2,000 miles now. It’s grueling, with no consideration for weather conditions whether it's storms or extreme heat. I think you’d be hard-pressed to find another sporting event that’s tougher. Three weeks is a long time to sustain that level of performance. And, of course, you’ve got the mountains, which everyone knows are difficult, but there's also a lot of time that’s just incredibly boring. Even in the dullest parts, every second counts. You see this every year when someone gets caught in a crash or has a mechanical issue. Time counts, so you have to stay focused, avoid crashes, and be mindful of things like crosswinds, which can be a huge factor in separating the field. It’s not like you can just sit back and wait for the time trials or big mountain stages. For three weeks, you need to be totally focused.

I think you have this maniacal vision in achieving the the win at the Tour. But how did you come to think this way? Can you put us in your shoes—what's going through your mind when you're winning?

That’s a good question. I’m not super proud of the answer. I didn’t love winning as much as I hated the idea of losing. What I truly loved was the process. I loved the off-season, mapping out my training and planning the season. I would say to myself, “This is the process that is going to get me to this place where I’m going to do everything I can to not lose.” After a few years, I came to expect to win, and I would have been devastated if I lost. Looking back, I realize that wasn’t a healthy mindset. Every year in Paris, I’d be thinking, “Alright, time to get out of here.” I didn’t stop to appreciate the beauty of the event or the significance of standing on the top step of Champs-Elysees hearing the national anthem. I didn’t give those moments the respect they deserved. Now, at 53, when I go to Paris, I see how special it is, and I regret not appreciating it more back then.

In many sports, staying on top is extremely difficult. Most people might win once, but you won seven consecutive times. What does it take to be so consistent?

It’s a lot of things. You need a lot of luck to–avoid crashes, an amazing team, and you have to be prepared. Seven years is a long time, especially with the months of preparation leading up to each Tour. My motivation never dipped–although that motivation was really about not losing. If I knew I had a hard training day ahead, even in the rain, I’d just put on my raincoat and go, while others might have postponed. I never struggled for motivation.

You went from the top of the world to being banned for life from cycling. Most athletes might give up in your position. How did you come back?

I’m proud of how I handled that chapter of my life. A lot of my peers who were disgraced it crushed them. Killed some of them. I’ve lost 5 or 6 chief rivals to drugs, alcohol, and all those habits. I could have gone down that path, but I chose to accept that this sucks, this is going to be brutal and I waited it out. I focused on my health, my family, and started trying new things when the time was right. Just like all of you founders, you learn to pivot and try different approaches. If something doesn’t work, you try something else. I don’t want to make it sound easy; there were plenty of days where I thought it might not work out. I was determined, though, and I didn’t quit. Fortunately, the world passed me back the ball and I tried to make the most out of it. Thanks to the times we live in, I was able to create my own content and connect with an audience again. My podcast started about seven years ago, and it’s been a huge part of my comeback. Had this fall happened 10 or 20 years earlier, none of that comeback would have been possible.

You have one of the most top performing funds out there. Can you share the story of your early investment in Uber through Chris Sacca?

Sure. I met Chris Sacca in Aspen, and we struck up a friendship. Later, he told me he was raising a fund, and I invested. I didn't ask a lot of questions. I was betting on the man. And if it was Christine Sacca, I would have been betting on the woman. Point is, I'm betting on the person. I didn’t even know he’d invested in Uber until years later when we were talking, and he told me about it. And Uber had just raised a new round at what we thought was a crazy valuation at the time, I think $17 billion. And he started telling me about the stake in Uber. And I was like, wow, that's crazy. I was like, what was the valuation we got in at? He said, $3.7 million. I said, whoa. All right. So I gave him $100,000 for Lowercase One–which you guys can figure out that ended up being a lot, which is awesome. The reality is without that chance encounter at that restaurant, bar, and Aspen, without betting on the man, and as my life unfolded and the lawsuits piled up and endorsements completely evaporated without that encounter at that place in Aspen, I don't know what I would have done for my family during that tough time of the meltdown. If you made me get up here and explain to everybody what Terra does, everyone would get up and leave. I couldn’t do it, it’s not my jam. But if you asked me about Kyriakos, I could talk all day here. Moral of the story is bet on people that pick good people and surround themselves with good people. It’s been a good run. It holds true on the angel investor side.

You have two successful podcasts. What does it take to make a good podcast?

It depends on the topic, but generally it starts with consistency. If you say you're going to release episodes regularly, stick to that schedule. Whether it’s once a week or a series, people need to know when to expect it. Beyond that, you have to be interesting and ask questions that people want answers to. I didn’t originally want to talk about cycling on my podcast, but we eventually added a cycling show because there was demand for my opinion on it.

Many founders struggle, and there are similarities between that and the Tour de France. What advice would you give to entrepreneurs?

Look, I’m not a founder so I might not be the best to ask. But I’ll go back to it and say I think it's all about people. Surround yourself with a good team and supportive investors. For me, I also try to support the people I believe in. Whatever Kyriakos needs or wants, I'll do it. I really will. I was out late last night with our headliner was Chris Stapleton and I said, that's okay. I'll get up early. I'll be there. But you go long and you go deep on the ones that you have the most conviction with and you fit in that bucket. And so, I love it. Just keep building, and we’ll be fine.

I would never in my life expect that. It's crazy. Thank you! Switching gears, can you share what you think the future of the Tour de France should look like? What should be changed or kept?

I think cycling is old school and continued to stay that way. I don’t think that will change for a long time. A single family owns the most dominant event, and they’re not letting go. Until there’s a fundamental shift in how the sport is structured, monetized, and who has a stake in the upside, which right now is primarily that family things will remain the same. If I asked my younger kids to watch a stage of the Tour, they wouldn’t do it. It’s too long for their attention span; they’d ask to fastforward for highlights or crashes. To reach a younger generation, cycling and many sports need to be reimagined. There’s a lot of activity in investment in sports—media rights, team ownership, and league ownership—especially now with more attention on women’s sports. The WNBA and women's soccer are gaining traction, following the path paved by tennis athletes like the Williams sisters. There’s so much money here as you can imagine. But here in our sport, have, I can only imagine how many times that family has been called to sell the event and they will not sell it. So, it's theirs.

You were an endurance athlete who put in countless miles. You start to crave all these kilometers like all day. You want to be all day doing more and more and more. How do you manage your training now?

As I’ve gotten older, I don’t focus on distance. That would be demoralizing compared to my peak. Now, I don’t look at miles I only look at vertical gain. If I can cover 3,000 feet or 1,000 meters in 90 minutes, I’m satisfied. The other way I look at it is through time. I’m fine if I train for one to two hours a day and focus on strength and resistance training, which is the best thing I can do at my age. Like I train at high rocks in New York, or in the pool in Austin as the most sustainable thing for me. You just have to have a different lens. If I think back to the number of miles I did before, I can’t do without 2 or 3 days without breaking down. Training for a marathon or triathlon won’t help me at 80, but strength and flexibility will.

How do think about balancing or focus with your love for many different sports and activities? And how do those map into entrepreneurship or other things that you want to do in life?

I've talked about all these endurance sports and sports that are, we would all consider sports, but my favorite sport to do in the world is golf. I love golf more than anything. This has to do with investing. Every decision on the course, from choosing clubs to navigating hazards, involves weighing risk and reward. It’s a math game. I love to play the game, but I also love to manage the risk of the game. Which is also certainly what we have to do as investors.

I'm fascinated by your reflections on motivation—how the hatred of losing drove you more than the love of winning, and how you've reconsidered that perspective over time. Have you found anything that fuels you in the same way but isn't driven by fear of failure or being underestimated?

No, nothing has replaced that feeling, but I’m okay with that. I'm a realist. I know that in my experiences as one of the most famous and influential athletes in the world weren't just on the bike, they were off the bike and they were incredible experiences. I'll never have those ever again. I mean, if Kyriakos sells Terra for $6 billion, is that going to feel the same as winning my sixth Tour de France, which broke the record that nobody had ever done? No. No offense, Kyriakos. I mean, for Kyriakos, it will be. We'll all be doing this little get together on his yacht in the Mediterranean off of Cyprus at some point. But no, it's just different. And that's okay, and I'm fine with that. Now my transition wasn't forced upon me, but it was impressed upon me. And so I had to think on my feet. People ask me all the time, “if you had to do it all over, would you do it again?” I say, “Listen. What are you talking about? Nobody gets do-overs. I know I have to do with what I'm doing right now and manage the situation. The only thing I ever cared about, once it's all melted down and I realized I was going to have to reimagine, recreate and reassess, I only had one goal: to support my family. The only thing I cared about. So if I can do that, I'm good. If I can't do that, I'm really not good.

You mentioned that you loved the process in preparing for the Tour de France, and your motivation was not so much winning as it was not losing. I'm curious how your thinking has changed as you've transitioned into venture capital where oftentimes a lot of losses can be offset by one big win. Could you talk a little bit about that?

I approach venture capital with eyes wide open. A couple things to keep in mind is how we allocate our time is really important and be realistic. The nature of this game is–at least the way my brain operates–start with a fund returner and that could be your grand slam. For us, Oura is a fund returner. After that, the LPs have been paid back, and now we're tracking the Kyriakos's of the world, the Vasu's at Vital Bio of the world, the Robins at outside, etc. You start to go down the list and then you're in the money. That's gravy. And that’s all part of the process. Now that’s very different from the other thing you asked about. Winning the Tour de France is just a six month process. Who wouldn’t love that? Like sign me the hell up for a six month process again. No, this is a 10 year process. This is very different. The way I view it, that just means you have to be more patient, more disciplined, and just let this process play out. My life and its relationship with six month processes is over. So this is a longer game. I mean, we've been at this jam for three or four years. That's already much longer than six months. But with that, it just requires patience.

Lance, You mentioned betting on the man. What are some character traits that you index on most heavily that people might not expect and things that are very positive or things that flag to you that there's a reason not to bet on somebody?

I’m not a “woo-woo” person at all. Just basin this on my track record there is this spidey-sense when talking to somebody. Virtual meetings make it harder, but in all of the winning bets I've ever made, I just sat with someone said, “I'm gonna support this person”. And it wasn't because they went to Harvard. I didn't necessarily call around and get four different references, although I do think reference checks are important and powerful. It sounds “woo-woo” but there is this feeling.

You said something that struck me, which is that you never struggled for motivation. Was there something in your childhood that made you this way? What is the mindset that you have when you're low and need to go back up? What's the mind model that you follow?

I think we learn a lot from our parents. My mom was 17 when she had me. So when she was pregnant at 16, she immediately got the words, “You're not going have that baby, right? You're not going to stay with this guy. You're only 16.” And my mom never wavered. She said, “No, no. I'm having this baby.” So I'm already absorbing that as somebody who's in the womb. And I do think that's a big part of it. When I grew up, my mom didn’t stand around and say, “Hey, you have to be motivated!” She never did that. I was blessed to have that. The other thing I've been blessed with is there's not a lot of days where I suffer from a dip or a lack of motivation. There are times of the day that I know that I'm better and I know I'm more motivated, whether that's a workout or a Zoom call, it doesn't matter. I'm a morning person. If you want to get the best Lance, you catch it in the morning. If I get past noon and I haven't worked out, I probably just won't because I know that's not my time. So, I know those things and sort of stick to my rules. So far so good.