Mental Flexibility: How a Tour de France Cyclist Adapted to Silicon Valley ft. Dylan Casey

Mental Flexibility: How a Tour de France Cyclist Adapted to Silicon Valley ft. Dylan Casey

Authored by Zhill Olonan and Geoffrey Woo • 
June 11, 2019
 • 57 min read
cyclingtechcognition

You've heard the popular saying, "You can do anything you set your mind to."

This mantra was key to Dylan Casey's success.

Dylan is a retired professional cyclist who rode alongside Lance Armstrong on the US Postal cycling team. After winning multiple championships, Dylan then switched career paths and began working up the Silicon Valley tech chain. From joining Google when they only had a few hundred employees to becoming a Senior Director of Consumer Platforms at Yahoo, Dylan not only built himself a storied career, but a varied one.

What was his secret? Determination? Intelligence? Hustle? Privilege? Luck?

Join us as host Geoffrey Woo explores Dylan’s journey and learns about the characteristics that enabled him to reach the top of two completely different industries.

In this episode, you'll discover:

  • How mental fortitude was key for Dylan to overcome career obstacles and switch industries
  • The state of endurance sports science during the late 90's and how the US Postal Cycling Team was ahead of the curve
  • Leadership, Purpose, & Diet: How to inspire a team (& yourself!) and what Dylan eats to stay on top of his mental game

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Transcription

Geoff

Hey, Dylan. Welcome to the program.

Dylan C.

Thanks, Geoff. You've created this great platform, this show, which is something that I've really benefited from. Having the opportunity to actually be a participant in that overall community of helping each other is actually why it's so much fun. So, I appreciate it.

Geoff

Thank you for the kind words. No, that's really generous. To lay out the background here, you and I met at a conference in Aspen-

Dylan C.

That's right.

Geoff

... about a year ago now. I think we became pretty decent friends, catching up and chatting over ideas around human performance, elite performance. But I think what is interesting from you, from a professional cycling background, is that you quite early pivoted into a tech career as a early project manager at Google, and then became executives at companies that we've all heard about, Yahoo and unicorn startups. That puts you in a very unique, maybe rarefied territory, for you were a elite world-class athlete and also an elite world-class tech executive and company-builder. Maybe to set the frame for yourself, what do you think of yourself? How do you describe yourself? Or is that just too complicated, like you can't label yourself?

Dylan C.

In kind of like looking inward, I have a completely different perspective than someone who may be reading my resume and establishing what it means. Because, for me, I'm just kind of like chasing the dream. Whether that was as a professional athlete or working in the tech industry, which was also, for me, something that I was always very passionate about. It's kind of like I don't feel like there's anything special about me.

Geoff

The narrative for yourself is that you were always pursuing the dream, which is, I guess, this broad definition that you want to be the best possible version of yourself, or some iteration of that.

Dylan C.

Yeah.

Geoff

That dream evolved from cycling with Lance and the U.S. Postal Service team to working with the early Google employees, building out the top five companies in the world, to now working at leading big product organizations at top tech companies, to ... I mean, obviously, that vehicle has shifted a lot. But I guess, from your perspective, it's like-

Dylan C.

I never set out to do those things. They weren't goals. Of course, the contradiction is that I love goals. I love the process around achieving goals. I love the work. I love the feedback mechanism, which is really how I discovered cycling and how I became so passionate about it was because I found this thing that, when I did work, there was this very tangible and objective result, which is I got faster. That was incredibly addictive for me. Almost an, actually, like addiction. I just loved that whole feedback mechanism.

But there were a lot of things that happened before that. For those that don't know my story, I came into the sport much later relative to my peers. The guys that I went on to become teammates with on the U.S. Postal Service had all mostly started when they were young children, especially the Europeans. They didn't go to college. I went to college. I didn't discover cycling until I was in college. It was kind of a hobby.

Back to the idea of, I've just been chasing my dreams. When I graduated from school, I went to work for a consulting firm in Philadelphia. I remember sitting there and kind of staring out the window and saying to myself, "All I really want to do is ride my bike. That's all I really want to do right now. If I don't go do that, I'm going to spend the rest of my life regretting it." I was like, "Okay, my life mission is to never have regrets," and so, I just kind of followed that mantra. I was like, "Okay, I'm going to go try. I'm going to throw myself 100 percent into this and see what happens." That was really what I did. Every year, I would get a little bit better.

Then, I started setting these goals for myself. If I can get here, I'm going to keep going. Then, the next year, if I can get here, I'm going to keep going. In fact, I wasn't even ... the U.S. Postal team seemed so far out of the realm of possibility for me, I was trying to get on another, like a bigger pro team here in the U.S., and the U.S. Postal Service came along, and I think I actually got turned down by the pro team that I wanted to go on. Because I was dating this girl, and the thought of going to live in Europe was scary, and the thought of competing on this world stage, I didn't think I was good enough. I didn't get the job with the local team, and I got an offer to go race in Europe, and I took it.

Geoff

Wow. How old were you at the time?

Dylan C.

I was, I think, 26.

Geoff

Wow!

Dylan C.

25, 26.

Geoff

Especially in the context of elite sport, because that's super rare, right? I guess you started just cycling as a hobby when you were in your early 20s, late teen, like 19, 20, 21.

Dylan C.

Yeah.

Geoff

It was in five years, you were competing at the highest level. As you were saying, and especially in this day, where people start optimizing their kids when they're like five.

Dylan C.

Right, right.

Geoff

So, there was some talent there, I guess, in terms of your genetics or some disposition. Did you play sports in high school? Soccer, or-

Dylan C.

Not really.

Geoff

No?

Dylan C.

I mean, I did a couple things. I was, actually, mostly into riding my skateboard.

Geoff

So, like a skater punk kid.

Dylan C.

I grew up in Walnut Creek, California, after living in Oakland as a young child. But I think, ultimately, in hindsight, I just didn't have anything that I was super passionate about in school. In fact, the only reason I went to college is because all my friends were going. I figured, well, I guess I should go. Again, back to what I said earlier, I didn't really have any of these goals, which is so weird for me to say out loud.

Geoff

Because you've done a lot of stuff.

Dylan C.

I've done a lot of stuff, and really, the key to a lot of the success that I've had is by setting these goals. I knew right away, especially when I got to the elite level, that I wasn't as physically gifted as people like Lance and George Hincapie and Christian Vande Velde and all these guys that I ultimately went on to become teammates with.

Geoff

In what way? Just in terms of, what, VO2 max, in terms of power output? What? Just like size?

Dylan C.

Yeah. You just know your limits. You know where the limit is.

Geoff

Okay, these people are putting out some power and speed. It's a little bit foreign to me.

Dylan C.

Yeah, I just knew it. I still had my success. I had things that I was good at. I won races, and on that day, was better than everybody else. I won the national championships a couple of times in the time trial and the pursuit. I won races in Europe and beat guys that were better than me. In fact, maybe that was one of the reasons that I really loved bike racing is because you didn't always have to be the strongest to win. Now, you got to be the strongest to win the Tour de France or other races like that. But it was just something that came to me and I was so motivated and so passionate about it.

Geoff

Which is incredible. As you're doing your consulting job, I mean, was there a point where it was like, okay, I'm going to just go full-time train?

Dylan C.

Yeah. I was like, "Okay, that's it. I'm moving back to Palo Alto." My girlfriend was going to Stanford at the time.

Geoff

You just like left your job.

Dylan C.

Yeah.

Geoff

You were just going to live out of a couch, or just live off your savings?

Dylan C.

I was living off of prize money. I didn't have any money. I had a student loan to pay back.

Geoff

Damn, okay.

Dylan C.

I remember a race, I think it was in Pennsylvania, in Altoona. There was a really big prize money race in Seattle the next weekend. I didn't have any money to get from Altoona to Seattle, so I looked on the prize list for the race the next day in Altoona to find out which place I needed to get in order to pay for the plane ticket to fly to Seattle.

Geoff

To keep the ball rolling, yeah.

Dylan C.

I was like, "Okay, third place or better. I got to get third place or better to have a ticket to go to Seattle." I was getting third place or better, no matter what. I mean, it was literally three laps to go, and I was like, "I'm taking this guy to the curb, because no matter what, I'm getting third place or better." Sure enough, I think I got second, so I had a little extra money. But it was just that mentality that I think has really stuck with me. I've been able to use that experience in a lot of the things that I've done in the tech industry. It's very similar.

Geoff

Yeah, no. It just reminds me. Obviously, Jeff Bezos has the famous regret minimization framework where he talk about optimizing for minimizing regret, and I think that's a pretty popular concept. It sounds very similar to how you approach some of these problems. I think it sounds like, so there's almost a bit of a greedy algorithm, and I use it in the sense of a computer science term, not like someone physically greedy. In terms of getting second place or third place and better, which is the most important immediate problem that you needed to solve to get to Seattle, and you went 100 percent, 120 percent into that.

Dylan C.

Right.

Geoff

It's kind of this interesting balance of, you have this long arc of minimizing regret, but it sounds like, as you pursued that minimization of regret, you were very thoughtful of the next step, the next step, the next step. It sounds like you were able to stack up a lot of these next steps.

Dylan C.

Yeah.

Geoff

Which, was that kind of that dichotomy of long-term and short-term optimizations?

Dylan C.

Yeah. It's where I really truly understood and appreciated the concept of micro and macro and how they're correlated. Because in that year of, or in that week of like, okay, I got to get to the next race, I also had a big picture of what I was trying to accomplish, which was, okay, get enough results to get a bigger contract or get onto a bigger team and have more opportunity. That really narrow focus actually helped me to be successful. In fact, I think it's something that stuck with me throughout my entire tech career, which is like having a super narrow focus and just being ruthless about execution. Almost in a way that is not necessarily always positive. You know what I mean? You can be so focused and so ruthless about what you're saying no and yes to, that there's collateral damage. You got to be willing to tolerate that.

Geoff

But I feel like, in this generation, in this day and age, I think people want to be too generalist. I think you're talking about really, really focusing, I feel like with a younger generation, there's this notion that everyone wants to be a generalist or a manager or product manager or all this stuff. They don't want to get their hands dirty being really, really expert and focus on one specific aspect of the task. Which I think we should talk about in more of the tech career. I don't want to skip between the U.S. Postal Service journey. When you were 26, you get signed to the U.S.P.S. Team. These are some of the, I guess, now, some of the most famous cyclists, period. What was that story like? I guess, what year was this?

Dylan C.

1999.

Geoff

Was that before or like after the hay days?

Dylan C.

It was before Lance won the tour. Even though we were a division one team, world tour team, pro tour team, whatever the nomenclature is now, we were really kind of the Bad News Bears of Europe. The team had some success. It was kind of the underdog American team. We had 16 riders on the team. There's eight riders in a race, and so, we were running dual programs at the same time, so all 16 guys are racing at the same time, because in Europe, there's oftentimes multiple races happening every weekend. Just the fact that we made it through the whole year was a miracle. Like, injury. Most guys didn't get injuries. Everybody wasn't sick at the same time. There were a bunch of impossible odds that we overcame to accomplish that.

Geoff

Yeah, a lot of logistics. I mean, it was like AB team or just switch people over?

Dylan C.

It depended on the race. Obviously, the only thing that mattered to the team was winning the Tour de France. So, there were some guys that were on the long team for the tour. You would kind of get lumped into that program and you would do races that were meant to build up for that program. Then there were the classics. It was very complicated. In a lot of ways, we were trying to figure it out along the way. But that's where really getting focused on testing and optimizing was critical. I think thinking about, of course, now, analytics and growth and this is such a topic du jour for the tech industry, and actually for what you guys are doing here in human with human optimization, we were doing that 20 years ago. We were so focused on metrics and so focused on feedback and so focused on data. In fact, it was our competitive advantage in that particular sport is that we were really focused on the details.

Geoff

I'd love to talk more about that in the sense that, okay, 1999, which is, I guess, 20 years ago now.

Dylan C.

20 years ago, yeah.

Geoff

I mean, sports science is probably just up and coming, I think, just talking to folks in this field. I mean, there was no such thing as sports science. There was just like physiology, biology. Then, there wasn't even that much money in professional sports, so there was not a science around it. But I guess in the late '90s that probably was just starting to come up. I'm also curious to hear about that snapshot in time where, really, I would say the U.S.P.S. Team made cycling, especially in America, a thing. Right? I don't know what it was like. I was probably, what, like 10 at the time.

I want to just set our listeners back into that time. What was it like in terms of the sport, in terms of the perception of U.S.P.S. Team? I mean, obviously, if Lance hasn't won his first tour, he was not a global phenomenon yet. In terms of the state of the actual sport, the metrics, the tracking, curious to hear about the sophistication there. Obviously, we had ... I remember this ... a blog post about the history where the earliest Tour de France is, people would be drinking beer at stops.

Dylan C.

Yeah, and smoking cigarettes because they thought it opened up their lungs.

Geoff

Exactly, and then it became more and more sophisticated. Curious to hear the snapshot in 1999.

Dylan C.

Yeah. So, I really kind of like grew up on the local domestic scene. I had a couple trips with the national team to Europe, but I really didn't race in Europe a lot until I went over with the Postal Team. I think Americans, in general, were a little bit more advanced than Europe, than the Europeans, for sure. I remember when I went over there, they were still telling us things like, "You can't eat warm bread because it will grow in your stomach. You're not allowed to have ice in your water." All these weird kind of like urban legends that just didn't make any sense. Even Postal, when I went to the team, was still a little bit, in my mind, antiquated. The staff was very European. There was still a lot of the European mentality.

But Lance and, actually, Johan Bruyneel, who was the director at the time, had a different approach. We were one of the first teams to start using power meters as a team. I think individuals had used it, but as a team and really build our entire program around the power meter methodology and the concept of power zones. Of course, I think that was an evolution of heart rate training and heart rate zones, but really understanding lactate threshold, understanding response to training, looking at a lot of the stress markers that your body produces.

Geoff

So, you're getting like the CO2, O2, like breath tests and tracking your heart rate. In 1999, you guys were doing that.

Dylan C.

Oh, yeah. We were doing VO2 max test, we were doing lactate threshold tests. We were also really looking, again, at a lot of the markers of stress in our blood tests. You could identify, okay, wait, you're over-training. You need to back off. We were starting to adopt a lot of the principles that today are just kind of like breathing. It's like so standard and basic.

Geoff

What markers were popular at the time? Cortisol?

Dylan C.

Cortisol, I think a bunch of the liver enzymes.

Geoff

AST, something, okay.

Dylan C.

Exactly. Obviously, we were super focused on-

Geoff

Put some of the amino acids or protein breakdown, maybe, for over-training?

Dylan C.

Exactly. All the teams had extensive medical staff and trainers that were starting to become pretty sophisticated. What's crazy is that, in the last 20 years, it's become orders of magnitude more sophisticated. Just when you think that the races aren't going to get faster, or anything, they do. If you look at the times on the track for the pursuit, or team pursuit right now, they're going sub-3:450, three minutes and 50 seconds for four kilometers from a standing start. Which is, in my mind, super human. You know what I mean? We were going in the mid-four minutes.

Geoff

That was world class.

Dylan C.

That was as fast as you could go, but it's because they're being so methodical about the approach and so focused. Now there's way more tools available. But we were really focused, and it wasn't just about nutrition, it wasn't just about understanding the response to training stimulus, but we were focused on our equipment, we were focused on traveling and sleeping and jet lag and a lot of the things that now are kind of in the bio-hacking community. It's one of the reasons I'm so excited about the time that we're in right now is because all of the stuff that I was thinking about 20 years ago as an athlete is becoming so mainstream. It's not just about excelling at sport, but it's just excelling at life. For me, that's why this is such an interesting time.

Geoff

I think it's also the tools are much more ubiquitous, right? At the time, you needed a physiologist and professional medical staff to administer the stuff for you.

Dylan C.

Oh, yeah. Just with the ordering and then the ability to see HRV and the readiness score and just kind of the correlation between behavior and how it impacts your sleep. I mean, I wish I had that when I was racing, because it would have totally changed my approach.

Geoff

It sounds like, even at '99, so you guys were at the cutting edge of sports science. That, you would say, is what, like the main edge above other teams? It sounds like, obviously everyone was optimized. I mean, one of the main things I like about sport is that everyone's trying to find some advantage over everyone else.

Dylan C.

Yeah, totally.

Geoff

That's competition.

Dylan C.

I think, in that particular point in time, one of the advantages that we had as a team, above and beyond the fact that we had some of the best cyclists in the world, and Lance obviously being one of them, is that we had a very unorthodox approach. Everybody else was basically operating the same way that cycling teams had been operating for decades. I even remember my first training camp, sitting down with Johan and the other general manager, and we're kind of just like preparing what the schedule was going to be that year, like what races was I going to do. I remember asking them, "Well, when do I get to have my time trial bike?" They're like, "What do you mean, when do you get to have your time trial bike?" I'm like, "Well, I need to have my time trial bike at home so I can train on it." They looked at me like I was crazy, right? Because this is just something that people didn't do back then. You got your time trial bike 10 minutes before the time trial started. I had always prepared meticulously by training on my time trial bike all the time.

Geoff

Makes sense, right? Like-

Dylan C.

Totally makes sense!

Geoff

... what's the ... prepare for how you're going to fight.

Dylan C.

Exactly. So, that was just such a foreign concept. Of course, we changed it. Eventually, everybody got a time trial bike that you got to have at home and you could train on it and you could prepare on it and get very focused on all these little details about the equipment. That was something that we did that nobody else did. Of course, now everybody does it. The other key thing is, Lance and Johan were famous for previewing the course ahead of time. That was something that they didn't do. Now, of course, every team does it.

Geoff

You got to visualize the whole thing.

Dylan C.

Everybody does.

Geoff

I remember watching some documentary. There's like driving the route.

Dylan C.

Yeah, yeah, yeah. I think a lot of it just had to do with the fact that we challenged the status quo all the time.

Geoff

I mean, it makes so much sense in retrospect, but just like what brilliance is, right? Something that's obvious in retrospect.

Dylan C.

Well, you have to-

Geoff

You guys were professionals, is basically what it was. Of course, you're going to race this route. You know what the route is. Take a look to see exactly what the route is.

Dylan C.

It seems obvious, but when we were in the middle of it, it was scary. We were going against the convention. Challenging the status quo took a lot of courage because it would have been much easier to do what everybody else did, right? Because then you're kind of limiting your exposure to blame. If we had done all these things and failed-

Geoff

It's like, oh, yeah, you guys change all this stuff and you guys suck.

Dylan C.

Yeah, you guys didn't follow the rules. You guys didn't follow the normal convention. It's actually one of the things that really appreciated about the tech industry. Especially when I got into it in 2003, 2004, is because this was like the land of breaking the rules or not following convention.

Geoff

Yeah, let's fast forward-

Dylan C.

So, I loved it.

Geoff

... in time a little bit. When did things change for you in the Postal Service? Obviously, I imagine after the first tour win, was there a pop-off, an interest, an excitement and a hype? I mean-

Dylan C.

Oh, all of a sudden, we went from-

Geoff

What was that like?

Dylan C.

... being nobodies to being total rock stars. A lot of that had to do with Lance because, I mean, not only did he win the Tour de France, but he was just so ... I mean, people just loved him. The sport loved him, and every ... and from a business perspective, the sport loved him. I mean, talk about changing an entire industry. We went from being at the races in rented motor-homes to being at the races in a huge bus. The profile of the team completely changed. It was a great experience. It was literally like a dream come true.

Geoff

Was it added motivation, or was it a distraction? I mean, did it become like a rock star lifestyle, where it's like-

Dylan C.

Not really.

Geoff

... you got fans, or was this like, okay, now we have more pressure?

Dylan C.

Yeah, it was more pressure. It was more pressure. You know what I mean? It wasn't like, after the races, we were hanging out at the hotel partying. We were like, "How do we get home as quickly as possible so we can recover and start training the next day and prepare for the next race?" But for me, personally, it was hard. I think it's especially hard for Americans and Australians and just people that have to go and live in Europe and travel so far from home. I just had a lot of different things in the back of my mind that were kind of nagging me about what I was going to do after cycling. I think I had this feeling that I didn't want to work in the bike industry after my cycling career was over. I just felt like I had other things I wanted to do. It wasn't a total conscious decision to retire and start a new career. It was kind of a series of events that happened in the perfect sequence. I was in just the right place at the right time that it happened.

Geoff

Yeah, tell us that story. I mean, so, it sounds like 2003, 2004, you retired and you wound up at Google, which in terms of timing is-

Dylan C.

Well, you know-

Geoff

... pretty damn smart.

Dylan C.

Oh, I mean, in hindsight, it was like the biggest grand slam, lottery, whatever you want to call it, of all time. In fact, my teammates give me the most credit, not for races I won or races I helped them win, but for leaving the sport and-

Geoff

At the right time.

Dylan C.

... at the right time and starting at Google.

Geoff

I guess see if, what they call the bombshell, obviously, off in the room there.

Dylan C.

Yes.

Geoff

With the doping, and then I guess you entered in a-

Dylan C.

I did.

Geoff

... very early stage with the-

Dylan C.

Yeah, I was very fortunate to avoid a lot of that, even though I was a part of that whole program. I take full responsibility for the decisions I made and whatever consequences I had to pay or have to pay as a result of that. That's a tough conversation, especially now that I have kids that are getting into sport. My older one is ... he knows what ... or he's starting to get a sense of what happened, and he knows the story. But for whatever reason, I woke up one day and made the decision to leave the sport and start at the very bottom in an entirely new industry. My girlfriend at the time was working at Apple, and she managed to get me an interview. In fact, it was funny because a recruiter called me one day. This was over the Christmas holiday, which is the off season for professional cycling. I was at home during a time that I would always be home, and all of a sudden ... and I hadn't quite made the decision to retire yet. I got a call from a recruiter at Apple. I was kind of caught off-guard by it, but all of a sudden the idea got planted. Like, oh.

Geoff

That's pretty random, right? Like, you're a professional cyclist.

Dylan C.

Well, but my girlfriend had submitted my resume.

Geoff

Oh, they referred you for something.

Dylan C.

Yeah, yeah, exactly. She referred me for this position.

Geoff

But your resume was like cycling dude.

Dylan C.

Yeah, exactly. I think that planted the seed, this idea that, okay, maybe I could make this transition. I went to do the interview and I was so excited about the job and so excited about Apple, having been an early adopter. Obviously, my first laptop was a PowerBook 160, or something like that. Ironically, all the guy wanted to talk about in the interview was Lance and the team. I was so annoyed because I was like, "Wait, I've done all this preparation for the interview to tell you why I'm the best candidate for this role."

Geoff

He wants to talk shop, cycling, yeah.

Dylan C.

Yeah, he just wanted to talk shop, and I didn't get the job. In parallel, so, during that whole process, I had a friend that worked at Google, and he helped me get the interview. It turns out that the only reason I was given the interview was a favor to my friend. It was like one of those things, like fine, we'll interview him. There's no way. He doesn't make the paper cut. He didn't go to Stanford or doesn't have computer science degree. He does not fit the template. They gave me the interview, and I learned later that I just out-interviewed everybody.

Geoff

Damn.

Dylan C.

I just got in. Once I got my foot in the door, I was in.

Geoff

What was the first title? Was it a product role?

Dylan C.

No. I started in the marketing department. Maybe marketing coordinator, or something like that. I mean, it was literally the proverbial mail room. You couldn't start any lower at Google than the position I was in.

Geoff

In that time, how big was Google at the time?

Dylan C.

I think we were maybe three or four hundred at the most-

Geoff

Damn.

Dylan C.

... in Mountain View, and maybe we had a couple hundred in sales offices in other parts of the world, but it was really small, and it felt really small. It's funny. You know what? I read this quote the other day, and I actually had to copy it so that I could remember it, because it's become so representative of a lot of the things that have happened to me and the story that I'm telling you now. But I'll read it for you. "There are things out of our control that sort of redirect us to outcomes greater than we would have initially chosen for ourselves." This was one of them. I didn't necessarily say, "Oh, I'm going to retire from being a professional cyclist and go work at Google." It just kind of happened.

Geoff

In retrospect, do you feel like there's some destiny, or you just, you think that's like you're dumb lucky, or-

Dylan C.

I, well-

Geoff

... you created that luck?

Dylan C.

I believe 100 percent that a significant part of the success that I have had has been due to luck or serendipity or being in the right place at the right time. And at the same time, being open to those opportunities, like listening to the signal. I have a good friend of mine who is an engineer, and we used to ... we made up this concept of the vector field. It's this concept that you're kind of headed in a direction, and you bounce off of things along the way.

Geoff

Kind of some bigger vector, bigger currents.

Dylan C.

Exactly. We would joke that ... I remember this one time when we were in Florida for something, and we had no idea where to go to dinner. We just looked at each other like, "Well, let's ask the vector field." The vector field in that particular case was like, we're sitting at the bar, we ask the bartender, "Okay, and you please tell us where we should have dinner tonight?" You know what I mean? And he was the vector. We would just follow it. It turns out that if you really paid attention and if you asked the right people the right questions, you'd end up where you're supposed to go. Anyway, it's this kind of intrinsic appreciation for serendipity that I think has served me well.

Geoff

At the time, so, very, very early at Google ... I think Google now is like, what, couple hundred thousand employees worldwide now.

Dylan C.

Yeah.

Geoff

Just basically, I guess, it's one, two percent first employees over at Google. Did you know that it was a special company? It sounded like-

Dylan C.

Not really.

Geoff

... you kind of knew you wanted to maybe retire from cycling, listen to this vector field a little bit, bounce around, got a favor to interview, got into kind of the ground floor. Was it like, okay, Google, maybe I kind of know about the search engine at the time. Were you thinking, oh, maybe I should go to Microsoft or another company at the time?

Dylan C.

It's so funny. I feel like I'm telling the same story over and over because I didn't. I mean, I knew about search engines and I kind of understood why they were important. I remember using Gopher to get around the web when I was in college. This is stuff that predates-

Geoff

Ask Jeeves?

Dylan C.

No, I don't think Ask Jeeves was around.

Geoff

I remember using Ask Jeeves first.

Dylan C.

I mean, literally, this is how I was getting around the various internets that were available to university students. But I knew enough, and I had been paying close enough attention to what was happening in Silicon Valley, having ... I was a resident a month or two out of the year. But I knew that Google was on to something. I just remember when I met people there and I was going through the interview process, that they were so focused on results and it was so objective. There was no subjectiveness. It didn't matter what I wore to the interview. Clearly, the people that were interviewing me weren't focused on what they were wearing, just as a illustrative example. But it was all about, "Okay, how are you going to respond to this situation, this question? If I ask you the classic, how many ping pong balls fit in a 747, are you going to crumble?" I just appreciated that focus on the actual substance as opposed to, did I wear a suit and a tie? Did I ask the right questions? Did I follow up with the 'thank you' emails, and stuff like that?

Geoff

Which probably felt really familiar to professional sport.

Dylan C.

That's right.

Geoff

Just like results. You win the race, get the job.

Dylan C.

Again, being bold enough to say, "I've never worked at a company, but I know I can be successful here." I went in and I said that. I said, "Look. I have all these trophies and medals on the wall, and they're 100 percent transferrable to what I'm going to do here at Google."

Geoff

Which is not obvious.

Dylan C.

No!

Geoff

But you're like, "I'm going to do it."

Dylan C.

Yeah, I said, "I can do this." I'm like, "There's nobody better on the planet than me for this job. I will just out-work everybody." It's interesting, of course, I remember in my first couple of performance reviews with my manager, he would tell me that, "Dylan, your confidence is really intimidating." I thought that that was so bizarre because I was so insecure relative to everybody that I was working with, because they were all Ph.D.s and just wicked smart computer scientists. The inventor of XYZ standard or language or ... you know what I mean? I just felt like such a small person. To get that kind of feedback was really fascinating, but I think it's also, there's a story I love to tell about athletes, and you'll hear this. Go to any start line of any race and you'll hear people talking about how they didn't sleep well the night before, or how they ... "I haven't been training as much as I wanted to." What they're doing is they're just basically self-disqualifying.

Geoff

Yeah, they're sandbagging themselves.

Dylan C.

They're just giving them-

Geoff

So, if they have a bad race, like, ah, I didn't try enough.

Dylan C.

Yeah, and I remember just being really curious about that because I had remembered points in races. These races are like six, seven hours long in some cases. In your mind, you go through so many different emotional states. I can remember being in races where I was like, "God I wish I could get a flat tire right now." Or like, "I don't want to be here. I don't feel good. I want to quit." Any reason to quit that you could somehow attribute to outside yourself. I got a flat or my chain broke, or whatever. Then, I just started, like what I would do is when I got into that moment, I would just say, "Dylan, remember your goals. Remember your goals. Remember your goals." I would repeat it to myself like a mantra. For literally 15 minutes, I'd be sitting there saying, "Remember your goals, remember your goals, remember your goals," and it worked. A couple of times it worked, so then I remembered every time, okay, when you start feeling like crap in a race or you're at the start line and you want to start complaining about how things haven't been going right, just say, "I feel great. I'm going to crush it today. I'm going to kill these guys." Even if you don't believe yourself, if you just say it, it actually works.

Geoff

That self-talk works, yeah. I think all of us have felt that situation before, where you just want an excuse to tap out. You need to rationalize an excuse that feels like it's honorable to be like, okay, I give up, or this was my day. You just need to have that extra fortitude, that extra bravery or courage to like, no, not today. I'm going to push through that. I think it's refreshing to hear from someone who obviously had a lot of success both in sport and in tech, that it is kind of like, okay, I just have that extra courage to say, no, I'm not going to tap out to an excuse.

Dylan C.

Yeah, that's probably the number one factor that has been part of my success in this second career is just having courage. It's super hard. It is really hard, and discipline, and focus, all those things. I still make huge mistakes. I'm so hard on myself, but I think as an athlete, the difference between the people that are successful and aren't, I think has everything to do with how you handle setback. You are going to have setbacks. How you deal with those setbacks has a bigger influence on your overall success than how you deal with the good days. I think that that's true for anything.

Geoff

I feel like, for myself, I am more forgiving on mistakes because I think there's a realization that you make a lot of decisions with incomplete information all the time, and you're going to make some bad calls at some point. If you just forgive that there will be some bad decisions, you've ... I feel like that's a more resilient, more sanguine outlook on life. Because if you just beat yourself up so hard for one mistake and you just crush all your momentum, that stops you from progressing forward. I'm curious, obviously, you need to be tough on yourself to be world class anything. How do you balance that, or how do you articulate that to yourself? How do you have that discipline to be hard on yourself, because you want to aspire to the top levels, but not be so hard or not have any forgiveness where the first time you mess up, you're like, I am a terrible person. I cannot do it. I give up.

Dylan C.

Probably some of it comes from my childhood, where my coping mechanisms were just to move on, like just forget about it. You know what I mean? Probably in an unhealthy way, honestly, right? Where it was like something bad would happen to me or I would be disappointed with something, and instead of dealing with it, or instead of wallowing in it, I would just put it out of my mind and move on. It was like I would just start over. In fact, my wife will probably tell you that I am such an optimist to a fault because I just have this innate ability to only remember the good things. You know what I mean? It's probably some sort of mental self-protection circuit breaker. But then, the flip side of that coin is-

Geoff

You're unstoppable. You won't quit.

Dylan C.

Yeah, I won't quit. I won't quit. Maybe I'll pause for a while. Maybe I'll do something else and ... but the things that I really, really want, I just feel like I'll get it, and I'm just determined. But a lot of that, it's tricky, because now I have kids. I have a 13-year-old boy, Cole, and an eight-year-old daughter named Sloan. I look at them as they struggle and they kind of deal with the various challenge that they're confronted with, and I try to think of like, okay, how do I help them learn that they're going to experience setbacks? It's the tools that you create to manage that setback that are going to be the major influences and determinations on their future. It's hard. It's so hard, because even in my own story, I don't know how to recreate it. I see these parents of kids, they're all trying to make them into the next pro whatever, and I think to myself, I'm like, I couldn't recreate myself, like my path. I couldn't.

Geoff

But over-optimizing or overprotecting, you might just reduce their ability to cope and actually be resilient.

Dylan C.

Right.

Geoff

I mean, I don't have children, but I think it is an interesting concept. How would you re-culture, almost reorient your own personality, right? I think one of the things that I think more people should be open to is that you can kind of retrain your thought patterns and evolve how you think. I think it's interesting, as you have children, or you're building a community, how do you pass along some of those principles down? I think it is interesting that to hear in common discussion that, with a lot of professional athletes or folks in military, that it feels like culture is softer, or people are, I don't know, weaker than they used to be. I don't know if that's something that people always talk about the next generation, but I think there might be something to that, where I think especially as people go to Stanford, you hear people talking about helicopter parents. People are optimizing the hell out of their kids. I mean, I guess, college people are bribing their way into school, protecting kids from actual setbacks.

Dylan C.

When I think about the criticism for the things that we did as professional cyclists and the scrutiny that we came under, which was warranted, but I mean, look at what people are willing to do to get their kids into college.

Geoff

I know.

Dylan C.

You know what I mean? It's both scary and I think illustrative of where we are right now.

Geoff

I didn't know there was like 20 years in jail for like, you made the comment, like oh, man. But you could assault people and not get that much time in the cell. So, I don't know how to think about all of that stuff. A tangent. But I think my main point I was getting to was that, so, as you ... I mean, it is something that you're still figuring out, but how do you translate that resilience? Because it sounded like you were able to work through a lot of resilience. I don't know if you had mentors or your parents or guidance with friends to help you process that resilience. Or was it something that was sort of self-taught? You just hit stuff and punch through. From that, how do you translate that?

I think, to me, you have to eat pain to realize a real lesson. Maybe you have some sense of this, as well. There's so much startup business books and just Paul Graham essays around what you should think about when you hire. Hire slowly, fire quickly, don't burn money, to build something people want. It's like obvious. You read it, like, that makes sense. Then you're just like, I don't know how to actually ... I don't know what it actually means, because you never did that wrong thing. I think there's actually like real meat and juice to actually doing the wrong thing and messing it up, that you actually learn what that very simple statement actually means.

Dylan C.

I have this saying that suffering has purpose. Suffering, the way that I think of it, is very positive, but the word I don't think has very positive connotations to it. There's this place that you go to, and I think this is especially true for endurance athletes, where you're just by yourself in your own head. Your only limits are the ones that you have that you've set for yourself. There's this real zen state that you get into when you're in this mode of suffering and you persevere through it, because there's a goal, there's objective.

I think that that's one of the things that I aspire to try to teach, whether it's my children or the people that I work with. Or now that I'm responsible for a team of people, how do I inspire them to push through their own limitations? How do I help them persevere through their obstacles? Because I don't think I'm going to be successful by telling people what to do or by handing them tasks. I think my greatest success is going to come from inspiring people to achieve more than they think they can do on their own.

In fact, that's what I did as an athlete. I figured out a way to achieve more than I thought I was capable of. That was it. Then I learned over the years in the tech industry, going from an individual contributor to a manager, that my role now, kind of my superpower now is, how do I get teams to exceed their own limits? A lot of that is just through a lot of these different tools that I've acquired, which, to your point, seems so clear and like, of course that makes sense.

Geoff

Yeah, you see that Paul Graham picked these things. Oh, yeah, self-evident.

Dylan C.

Prioritize and, like I said earlier, narrow focus and focus on execution. Oh, there's a million good ideas, but it ultimately comes down to the teams or individuals that know how to execute and operate. Of course, that makes sense, but it's so hard to do. It's the hardest thing to do. I came up with this other ... I think it's going to be on my tombstone, but-

Geoff

This better be good.

Dylan C.

I think I kind of created it in my head in these moments of being in races in Europe where I was off the back, not even in the race, and just surviving to get to the finish line. It took me a while to come up to it, but here it is. The sweet taste of victory is afforded to those who can eat bitterness. I'm being very repetitive in a lot of the stuff that I'm saying, but I totally believe in it. It's my North Star. I think, to the degree that I can try to inspire others to kind of go to that same place, it's super rewarding to me.

Geoff

One of the things that I've ... As I've been talking to folks like you and working with folks that are very elite athletes, I definitely sense the fact that when you're doing something like an endurance race by yourself for a couple hours, three, four hours, it is very lonely. It's like constant chattering in your own head.

Dylan C.

Yeah.

Geoff

Some of the advice that I've gotten is that you have to either trick yourself or brainwash yourself or self-talk yourself into liking that bitterness, liking that pain. People call it the pain cave, you could enjoy being in that pain cave. Obviously, you figure out ... what are your tips to enjoy that pain or enjoy that bitterness? Because I think there's absolutely ... that's the difference between someone who cuts through. It's like, okay, you were able to eat that pain and taste the sweetness of victory. Everyone just can't push through. Is it genetic?

Dylan C.

Well, I think it's like systems theory. There's so many inputs and the system is ultimately looking for equilibrium. I think that's kind of a geeky way to describe it, but for me, I found satisfaction and reward in the feedback loop. I think it was because it was like I have control. If I do the work, I'll get this response. The podium was just the result. That was the thing that validated the feedback loop. It wasn't the end result. That wasn't the reason to do it. The reason to do it was because I really thrived in this feedback loop. I think the way that that translate is to really find out what makes you feel good. You know what I mean? What makes you feel rewarded?

One of the ways that I try to connect with people when I'm working with them Is I try to figure out, what do you really like? Why are you doing this? What do you really want to get out of this? What makes you excited in the morning to come to work or to do whatever it is that you're doing? Because it's always something else, other than, I want to get a promotion, or I want this job, or I want to win this award. While those things are true, I don't think that that's the main motivation for most people. I think there's something more intrinsic. If you can figure that out, you can really help people focus on it.

In my last job, I had this incredibly smart, ambitious, talented person on my team. He would be so upset in our one-on-ones about the fact that other people weren't working as hard as he was. He was working crazy hours, and everybody else was going home at 5:30. I asked him, I'm like, "Well, tell me why that matters to you so much. Why is it so upsetting to you? Do you want to work less? Do you feel like you're picking up the slack? What's the deal?" He said, "No, no, no. I just really need this company to be successful so that I can make a lot of money." He's like, "Because otherwise, it's not worth it. I'm killing myself. The only thing that matters is how much the stock is going to be worth."

I was like, "Whoa. Okay, let's hit the reset button. Pretend for a moment that I'm not your manager, I'm just a friend telling you some wisdom, if you will." I'm like, "If the only thing that matters to you is what the stock price or what the financial outcome of all of this work that you're doing, you're going to be incredibly disappointed when you get there. I believe you're going to get there, but you're going to be super disappointed."

I'm like, "The thing that you should focus on the most right now and that you will care about the most in 10, 15, 20, 30 years looking back are the experiences that you have right now and the story and the anecdote that you're going to get to tell from the story. Now, whether it's in your next job interview or it's when you're sitting around the campfire with your grandkids, this is what's going to matter to you. Think about that. Think about the story that you're going to get to tell." I honestly believe that. It's like funny, early days at Google. We weren't allowed to look at the stock price. You know what I mean?

Geoff

It's like banned on the computers?

Dylan C.

It was. It was. There was no stock tickers anywhere. It was like, don't focus on it. That's not the thing to think about.

Geoff

That reminds me, like that very much a similar philosophy I have. I articulate it in a little bit of different way, but I think about it, process over outcome. It's really refined mastery around your skillset and what you want to be world class at, and have the outcome be the side effect. If you're chasing a goal, and oftentimes that goal is not controllable, like a stock price, or beating someone in particular, you cannot control their life and what they're doing, but what you can control is your own process. The second part I want to respond to is, I think we're relatively lucky that we can choose to spend our time to something that we want to have mastery of.

I'm just wondering, and I know some people will be thinking in the back of their head, well, what if they need to just make money? Right? I don't know if I have a good answer about that, because I've been thinking about this kind of more macro. Maybe we zoom out a little bit, and more philosophical and socially. But it's like, I would say that probably most Americans and most people, in general, just probably don't even like what they're doing. That just might be a fact of society's kind of messed up. We're not going to solve this in this conversation, but curious to at least open up that can of worms around, okay, you have to be relatively lucky in terms of even having a way to be able to focus on the process. Most people just got to get the money to pay the bills.

Dylan C.

Yeah, you're 100 percent right. We are, and I consider myself to be incredibly lucky and fortunate. I feel so rich because I have choices. I can make choices, and I think that that's the ultimate reward. I think there are lot of people that are in really hard circumstances, and it tugs at my heartstrings all the time when I see people that are in tough situations. I get a lot of inspiration from people that, for example, they don't have as many options. They don't have as many choices, and they do have to work a job that they don't like and they don't get any personal satisfaction out of it. But then, you look at the effort that they go through to have a huge barbecue with the family on Sundays, right? Or the fact that they're trying to play on the local softball team at the park at 10:00 p.m. on a Thursday night because that's so important to them. I really appreciate it when I see people doing that because I think it's just another example of chasing after something that you're passionate about or that you need and it's important.

Geoff

That makes sense. Doesn't necessarily have to be the passion is your job, but I think that makes sense that there are circumstances where that passion can be and maybe is more optimally channeled in other aspects of one's life.

Dylan C.

Yeah. It's the person who has a standard 9:00 to 5:00 job in an office, but then plays music in a band with his friends or her friends on a week night. I think we have to figure out a way to support and celebrate that, above and beyond just whoever's working at XYZ unicorn company or tech company. We definitely live, especially here in Silicon Valley, in such an echo chamber. I think that's one of the things I really appreciated about having the opportunity to travel around the world, or even just around the United States and see so many different perspectives and different people.

Geoff

That just reminds me, some of the comments we get on our podcast is like, you guys ... and Zhill will remind me of this, our producer, but you use too much tech lingo. There's too much Silicon Valley business talk here. I appreciate that because it is ... there is a language, a culture around tech and startups and financing, adventure capital, and building companies, and changing the world. I think that's starting to come to a head with the broader discussion on politics, where I think we were talking about this before we turned on the tape, around regulation, pushback, is tech too big now? Obviously, as you've been at Google, Yahoo, some of the unicorn startups, what are your thoughts there? Obviously, you've worked with some of the most prominent people at Google, Yahoo, all these name brand companies. Maybe you could help maybe unpack that or maybe reaffirm that these are super evil people, they're good-hearted people. Maybe help translate what the New York Times will write versus what you actually see on the inside, knowing these people as people.

Dylan C.

Yeah, wow. That's a big question. We could have a whole podcast just on that topic, itself. But Silicon Valley is a unique place, and it has pros and cons. For me, this was my home. I grew up here. I love it here. I've really thrived from being around people who really set impossible goals for themselves, and have benefited as an athlete, and then also as somebody that's been a part of this community in the tech industry. I think we have a responsibility as this community to do the right thing for the rest of the country and the rest of the world. Google was probably a good ... Google and Yahoo, for sure, but Google had this mantra of, don't be evil.

Really, the story behind that, and I think it's pretty well-known, but ultimately, that was a group of people sitting in a room trying to make a decision around how to treat advertising results relative to organic search results. There was a lot of debate, and everybody had a different point of view. Ultimately, somebody said, "Hey, don't be evil. We should just not be evil. That should be the principle by which we make this decision, because it's the right thing to do." I wasn't at Google when that happened, but obviously it was part of the culture. It's ironic that now it's used against them, almost to paint them out as like, hey, you guys said don't be evil. You're being self-righteous now.

The scary thing is, having been on the inside and read those New York Time articles and knowing the truth and the delta between the truth and what's written, it's ... I mean, first of all, just, I'm not a fan of journalists. I am not a fan of journalism, in general. I mean, I don't think that ... Journalism was supposed to serve this purpose, especially in the American culture and government of like checks and balances. It was supposed to be the barometer or the limit, set the limit on things. I don't think that that's the case anymore. Maybe the tech industry is partly responsible for that, by measuring clicks and performance. Maybe there's a discussion to be had around that. Maybe that's the discussion that should be front and center with regards to politics and Facebook and Google and data and privacy and all of that.

But it's interesting, with thinking about Google, I know how much information and data they're storing about people because I was there and I've seen the logs. Ironically, I was part of the Google Plus team, which had to figure out a way to build an entirely new logging system that actually stored personalized information about you. Because up until then, Google was all about aggregated, non-personalized information and data. So, that completely changed. But I had to become aware of the fact that even people in my own family are uncomfortable with how much information Google has, and Facebook, and other companies.

I think that that's what we all need to focus on. It's like, I can't even convince my own family members that Google really does want to do the right thing and wants to be very mindful and cognizant about what it does with their data. There's things that I saw and experienced that have formed my opinion, formed that opinion, and unfortunately, I can't share some of those things because they're confidential. And the New York Times won't write about it, or won't write about it in a way that is actually altruistic. They'll write about it in a way that gets the most clicks.

The funny thing is, I went through the same experience with U.S. Postal and Lance. The whole thing about taking Lance down, there was no positive outcome for anybody except for Travis Tygart and some of the government. The only reason that we even know who Travis is, is because he's the guy who took down Lance. The only reason that we know who Ken Starr is, is because he's the guy who took down Clinton. There's a whole different agenda going on there. The funny thing is, I hated ... I was in races and I would read the race report from a journalist after the race, and I'd be like, "That didn't happen," or like, "No, that's totally wrong."

So, I started writing my own race reports, because I was like, "I'm going to tell the real story about what happened inside. In fact, I'm going to give you a different angle and a different perspective, which I think is actually more interesting." Which is this company that Lance and I started called We Do, which is the answer to the question, who wants to run 100 miles today? He has two podcasts, one called The Move, which is basically a post-race commentary, and the whole intent of that show is to say, "Here's what we saw really go down today. Here's the insider perspective," because I think that that's interesting from an entertainment perspective. But from a journalistic perspective and how it relates to politics and the tech industry, what we really need to be asking ourselves is, how does that relationship actually occur in a way that benefits society and not just benefit either lobbyists or advertisers or the companies, themselves, with regards to what their stock price is? That would be a conversation I would love to have. And nobody's having it.

Geoff

I think you hit the good point, which is the incentive of the journalist to win a Pulitzer. Which basically means it's got to be juicy, meaty, got to have some blood sport in it. I think that's where there's that, I think, that cloak of, are we objective, are we biased? I think that's the hard part, where I think that's the complication right now. Because can you have that objective media? If not, then do we just assume everyone has this opinion and everyone's going to be biased? I think it's like, if you're a human, you're kind of biased. I'm biased, I'm-

Dylan C.

Totally. 100 percent, I am biased about Google. There's no question. I'm sure people will listen to my comments, or if people ... I would have a conversation with people and they would just, they would call me out.

Geoff

Google paid him off, whatever.

Dylan C.

Yeah, yeah, exactly. But look, I have a set of experiences. Those experiences formed my beliefs, and that's the point of view I have. Now, like I said, I have people in my family who have a completely different point of view, and I'm okay with that. I think the opportunity is, understand why they have a different point of view. I just want to know. Tell me why you think that this company is really out to cause you harm or is not genuine or not ... isn't actually doing something in your interest. Because I want to know about that. Especially if I worked at Google, I'd really want to know about that, and Facebook, as well. I think those are the two companies right now that are really in the cross-hairs of this whole debate. But having been on the inside of those companies, and I was inside Yahoo, and right in the middle of the very well-known, famous data breach, which at the time, was the largest data breach in history. It's been a couple of years since that happened, but now it's like everyday news. It's no big deal, right? But the delta between what was written about that and the truth about what was going on inside is huge. Unfortunate, there isn't a way to actually make that known in a way that ... because everybody's in CYA mode.

Geoff

Yeah, and it's funny because I think you see this pop up in all sorts of domains. People say like, yeah, the paper record doesn't actually match reality.

Dylan C.

No.

Geoff

But I think you talk to a journalist, and I know personally a lot of journalists. I think they try to do their job. I think it's just that ... I think it's just hard.

Dylan C.

I do, too.

Geoff

I'm sure you know a lot of reporters and journalists. I think they are trying to do their best possible job, but maybe it's like this kind of arbitrary notion of objectivity that is kind of like you have to project what does mainstream think is objective, and then maybe a lack of actual first-hand experience in the full, full context I think just makes that very hard for someone who kind of drops in.

Dylan C.

The thing that I think has been so core to being a good product manager, which is, you're ultimately trying to build an experience for a user for a purpose. That's it, in a nutshell. I think, for me, I've always been able to do that by having empathy. Much in the same way that I said that getting to understand somebody's real motivation is really important in getting teams to work well together or just working well one-on-one, I think that's the same, that level of empathy and understanding, even if you don't agree, is what we should be doing right now as a society with regards to politics and the news and companies and Wall Street and how that relationship ...

I think the smartest people or the most effective people with regards to how this relationship is getting managed between companies and press and journalism are the ones that are able to sit down and say, "Hey, look. You have an agenda, I have an agenda. Let's just be very clear and explicit about what that agenda is, and then figure out a way that we could work together in such a way that we're actually providing real value to the person who's reading your article and to the person who's using my product." If we can do that, we may not agree on everything, but at least we're doing something that's valuable. We're actually making some sort of forward progress.

But if you can't have that level of empathy for the journalist, and to some degree, I regret saying I don't like journalists or I don't like journalism, but the reality is, you really just have to work harder. You have to really set aside your own ego or your company's ego and say, "Okay, you have a purpose here. You have a goal or an agenda, and I do, too. Let's figure it out together." If we can do that, then there's real symbiosis here. There's a way that this whole ecosystem works together.

Geoff

Yeah, I mean, I think you hit it on the head in terms of just like ... I think about it like full band of communication. Let's just talk about it for real. Like the subtext and the language and its actual meaning. I think it's like, it's hard to know when you can communicate, at what level, to which people.

Dylan C.

Well, have you ever heard two lawyers talk to each other, especially opposing lawyers? It's so interesting. I remember the first time I heard it, I was so caught off-guard because they're so matter-of-fact. Like, "Oh, hey, how's your kids? What baseball game are you going to this weekend?" Then like, "Okay, here's how this is going to go." Then they get down to business, and they're kind of like, "Look, this is how this is going to play out." It's a very clear, structured set of rules about how this is going to be interpreted. Here's my point of view, you disagree. Let's negotiate. They walk out of the room with an agreement. It's the craziest thing I've ever seen. Right? It's almost like, okay, that particular industry has figured out how to do it right. I think there's a nuance there. If we can figure out how-

Geoff

That's actually an interesting analogy, because it is a brutal situation, but I think that's just their job. They're used to it. They know that, hey, there's some-

Dylan C.

Yeah, they're dealing with, in some cases, a person's future life, like whether or not they're going to spend the rest of their life in jail or not. They kind of use their experience, they use the context, they're unemotional, they're very objective about it, at least to the degree that they can be objective.

Geoff

Like, "Here are your points, here are our points." Obviously, with any kind of dispute, there's some points on both sides, but have some credit. It's like, okay.

Dylan C.

Right, right.

Geoff

Get this resolved.

Dylan C.

I was so excited when I came in here, Geoff. Now, I'm bummed out. No, but I think there's a lot of opportunity here. That's the way I see it. I think if we focus on those things, if we prioritize that particular part of the conversation, we're going to come out in a much better place than if we get stuck in this, yeah.

Geoff

Well, I think it's actually kind of a good pivot point to go back into human performance and mindset, which is that that transparency and that level of communication and honesty to the counterparty. It kind of pulls full circle. You have that counterparty or that ... you need to be as honest and brutally honest with yourself in terms of self-talk or you're doubting yourself. Okay, how do you buffer yourself back up?

Dylan C.

It's funny. One of the reasons I've been such a huge fan of the work that you guys are doing, and I think there's a lot of other companies and individuals that are using a very similar approach, which is, let's look at the data. Let's look at the science. Let's take the subjectivity out of it and let's be as real and genuine and authentic with our customers and the people that we're trying to appeal to, because that's a much better ... it's a more convincing, more persuasive approach than, you know, what celebrity you pay to use your product, which is the traditional path. Or the anecdotes that come from people that are basing their experience on science and data and the structure that comes from that, it's just such a refreshing approach. For me, it resonates because I feel like that has been the approach that I have always been attracted to, even in early days as an athlete.

Geoff

Yeah, thank you. Yeah, I don't think it's even being smart. It's just like what ... I think what you and I have both cut out in terms of the cloth, it's like, I don't want shit that doesn't work. Let's just be real to what the data says and what the evidence says. I don't know. I think you got to credit it to the customer. I think people are smarter.

Dylan C.

Totally, and they're willing to do the work. I think that there's such ... Like I said, this time is so exciting for me because now it's not just about athletes that are trying to live the best or be the fastest. It's really around, how do we live the best life? How are we the best parents that we can be, the best friends, the best employee, the best manager, the best person, the best member of our community?

Geoff

Yeah, I'd love to talk about that. Obviously, you were very metrics-driven and you are athletic career. Now, with more and more technology ordering we mentioned, what are you optimizing now? I think there was a New York Times article about how Jack Dorsey is this influencer in terms of dictating lifestyle, just as much that Hollywood celebrities are dictating lifestyle choices. Now there's bio-hacking Jack Dorsey, who's Twitter CEO, and other bio-hacker types who are setting lifestyle culture. Curious to hear, are you applying some of these techniques in your personal life? What are you measuring? What are you tracking?

Dylan C.

Totally.

Geoff

What are you up to these days?

Dylan C.

For me, it's the same pursuit. Just really trying to get the most out of what I have. I think, with technology, there's all these tools that give us a better feedback mechanism, trying to understand the difference, or identifying the difference between correlation and causation, which again is so critical to when you're building a product and you're trying to figure out, okay, why did this happen? Or when we did this, did it do what we expected it to do? I think the crossover there is so clear to me. But yeah, I think I obviously don't compete at the same level that I did before, but I still love competing. I love the experience of competing.

Geoff

You still racing, cycling?

Dylan C.

No, not racing as much formally. Although, last year and the year before, got together with a couple of my former teammates, Lance, George, and Christian, and we did a 24-hour mountain bike race in Tucson. It was like a relay. It was fun because we felt like juniors again. We were all nervous and excited. We trained really hard. We prepared, and we're like, "What kind of tired are we going to use?" We got into all the details again. But, at the same time, we were there just to have fun.

Geoff

Did you guys just crush it, or is this like a super pro event, or?

Dylan C.

Well, no. It's more of what I would call a participant event, kind of like Iron Man or a marathon. You have people that are there that are at the very, very top of the sport, and then you have people that are there, just like, I just want to finish this thing. It's actually what made this event and many events like this very, really exciting and fun for us. Because we could compete however much we wanted to, but then, at the same time, we could stop at the whiskey-

Geoff

Enjoy the experience, yeah.

Dylan C.

... thing and take a shot of whiskey and enjoy the whole experience. I still love to do that, but I love ... I've completely become a morning person because it's generally the only time that I have to work out, and I have to work out. I love working out. It's my church. It's where I solve all my problems.

Geoff

Waking up at, what, 6:00? Are you like-

Dylan C.

5:00.

Geoff

5:00, okay.

Dylan C.

Yeah. 5:00 pretty regularly.

Geoff

Alarm clock, or just like your circadian rhythm is just-

Dylan C.

No, I have to use an alarm clock, but I've definitely gotten into ... I am definitely a sleep princess. Ear plugs, eye mask, cold room. I try to get away from my computer and my phone as early as possible. I try to do a lot of those things just to really get the best sleep. Drink a lot more water. I mean, again, it's funny. I wish I would have known all these things when I was an athlete. I think I would have been 10 times better, just focusing on these things, or just understanding the impact and effect on overall things.

Geoff

How about nutrition? Are you looking at fasting, intermittent fasting-

Dylan C.

Yeah. I love intermittent fasting. I cycle between either zero carbs or super low carbs on days where I'm not very active. Then, days where I am super active, I'll-

Geoff

You'll fill up.

Dylan C.

... I'll eat carbohydrates. But I try to focus on really high-quality, clean carbohydrates, which is ironic, given that we used to carry around these boxes of stuff called [Extran 01:18:05]. It was basically straight glucose. We would use it in the last hour of the race.

Geoff

Just downing sugar.

Dylan C.

Just downing sugar.

Geoff

Yeah, yeah, makes sense.

Dylan C.

Now, in hindsight, looking back on that, there's just so much, the nutrition has completely changed. It's so much different. I guess you'd call it targeted keto. While I appreciate the effects that it has on my body composition, because I have to pay a lot more attention to that than I used to, I actually really like the clarity that I get from it. I feel like the words come easier to me. My brain just works better. That's where I really discovered some of your products. Yeah, I just think there's just a lot of interesting things to it. Now, I could go on a whole different rant, and I think a lot of this has to do with the fact that I'm a parent, but just seeing what our kids eat. I was at this soccer game the other day. My son plays soccer. The team before us, the whole teams gets off the field and there's rows and rows and rows of McDonald's Happy Meals and Gatorade and these little Hostess cupcakes.

Geoff

Wow.

Dylan C.

I'm just like, "Oh my God." I just can't believe that. It's so shocking and, at the same time, so depressing.

Geoff

So American, right. That's, yeah.

Dylan C.

You know what I mean? If we can really educate people about what they eat and how it impacts their lives, we have a chance at changing behavior. For example, with my own kids, I've tried to get them to understand the connection between food and performance. My daughter, when she gets upset about the fact that she struggles in math or she feels like she can't do the math problems fast enough, I say, "Well, did you drink any water in the morning? What did you have for breakfast? Did you have pancakes or did you have eggs and-

Geoff

Interesting.

Dylan C.

... "some yogurt?" I'm trying to get them to understand this correlation between what they eat and how they perform versus good food and bad food. Like, oh, that's bad for you. Try telling a kid that a piece of chocolate cake's bad for him. They do not hear what you're saying. They do not care. You know what I mean?

Geoff

You're training to think about, just input the system, versus like, I'm going to give you the automatic sense of random arbitrary rules I don't really understand right now.

Dylan C.

That's right. My son, he wants to play soccer and he wants to be really good at it. I'm like, "Okay, let's go to sleep early. Let's think about what we're going to have before the game. Let's think about what we're going to have after the game." Just trying to arm them with those tools and understand the correlation between what you put in your body and how you perform, there's tons of causal evidence.

Geoff

Yeah, I mean, it just reminds me of like a computer science analogy with machine learning, as opposed to writing rules. Like, AI used to be defined by rules. You do this, or in this case, do this. New math, the statistical math is, you're giving them data points. Then, you don't tell them the rule. The rule is self-evident from all the data that's being ingested. It sounds like you're essentially ... I don't know if this is the way you thought about it, but you're essentially machine learning training them by giving them data points, versus like, don't eat Hostesses, or whatever.

Dylan C.

Yeah, I definitely don't proclaim to be applying a machine learning model to my children. I'm sure if my wife hears that, she'd kill me. But that's my approach, because I'm not going to get through to them with rules. I have to help them, I have to arm them with the tools to understand the correlation or the causation and cause and effect, and all that. I think that the whole movement around functional medicine and functional health is really fascinating to me because it's no longer about treating a disease, and it's all about how do we get you into the best state that you can be in? How do we optimize you? Not only does that personally excite me for my own personal ambition, but I also think that it's going to have a really positive effect on our community and people. I think there's just so much benefit to come from that.

Geoff

One of the last questions I always ask, and I'm curious at your thoughts on is, if you had infinite resources and infinite guinea pig humans, or whatever population you want to study, what would the setup be? What research project would you want to run?

Dylan C.

I would want to do something like ... is it the biosphere? Wasn't there this study that they did in the Arizona desert?

Geoff

Yeah, the little like, yeah, a biosphere, little-

Dylan C.

Where they basically created this self-contained-

Geoff

Yeah, they had to farm their own food and purify their own waste. I remember reading about it. There was a mishap with the production, so there wasn't enough food, so people were calorically restricted. It was an interesting little experiment.

Dylan C.

Yeah, I think I would like to do something like that. I have to spend some time thinking about how to design my experiment. But if I could do something like that, that would then create data and information and anecdotes that people would really gravitate towards and say, "Okay, yeah, this makes sense. I get it. I believe this." To the degree that it could help them understand things like, when you're at the start line of a race, tell yourself how good you feel, even if you feel like crap. Or if you want to do this or that, drink more water. Or if you want to feel better, you want to sleep better, you want ... just if we could figure out a way to get that mindset to be mainstream, I just feel like all boats rise with that tide.

Geoff

Yeah, level up society, right?

Dylan C.

Yeah. Yeah, totally. Level up society. As the product manager, I'd have to think about what the road map would look like. What do we have to launch along the way-

Geoff

Timeline, what resources you need, yeah.

Dylan C.

... to get there, right? Because it's not easy. If it were easy, we'd already be there. But I think there's a lot of interesting things to come in the future, especially as we get better about measuring and storing data. I think, also, I mean, I actually love history now because you can go back and you see these patterns that have repeated themselves over and over and over and over. Can we figure out a way to stop doing the same dumb thing over and over?

Geoff

I don't think so, because people die, and then they don't read history.

Dylan C.

Right, so it has to be a different curriculum, right, or a different way of that vicarious lesson. Who knows? Maybe there's something we should do there.

Geoff

Yeah, no, this is a fascinating conversation. Where do people follow along? What are you up to next? I know you have Twitter. Where do people find you?

Dylan C.

I have Dylan Casey everywhere because I was an early adopter of-

Geoff

For just about-

Dylan C.

... everything. So, whether it's Instagram or Twitter. Yeah, and I'm super easy to get in touch with. Just one quick little story. I broke my pelvis and my collarbone one year in a horrible crash. Bicycling magazine asked me if I would ... I was already contracted to write a bunch of articles for Bicycling, and I was going to be doing some races. It was supposed to be about the races. Well, I crashed, and so, they said, "Well, do you want to just write about your recovery?" I was like, "Sure, whatever," because they were paying me.

I'd write these articles, and the articles were just all totally focused about me and what I was doing to get better and how I was recovering from my training. I was almost angry about it. You know what I mean? I was like, "Oh, whatever." I got this really heartfelt email from somebody who said, "You know, Dylan, I had the same, exact accident. Reading your articles about what you were doing to overcome your accident were so inspiring to me." I was so shocked, because I was like, "What?" I mean, I can do something that is so self-serving and selfish, and help other people at the same time?

Geoff

I want to do this more.

Dylan C.

I thought that that was great. I've really come to appreciate and get a lot of personal satisfaction out of helping people. I wouldn't have gotten here or accomplished the things that I've been able to accomplish if it weren't for a lot of people helping me along the way. So, I really try to help as many people as I possibly can. Anyway, you can reach me. Pretty easy to find. I'm hoping in my next go-around, whatever my next job is, because I'm kind of in between right now on the proverbial beach, gives me the opportunity to do that.

Geoff

This was one of my favorite conversations. Thanks so much, Dylan.

Dylan C.

Yeah. Thank you for having me.

Geoff

All right. Awesome.

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