David speaks with Jason Shen, a three-time founder, writer, executive coach, and NCAA gymnastics champion. Jason cofounded Ridejoy, a ridesharing platform backed by Y Combinator, and later built Midgame, an AI gaming company that was bought by Meta. As CEO of Refactor Labs, he helps founders and teams build successful companies. He wrote The Path to Pivot and Weirdly Brilliant, sharing lessons on resilience, leadership, and reaching your full potential.
They talked about:
✨ How consistency creates opportunity
🎭 The impact of cultural identity
🤸♂️ The discipline behind gymnastics
🏅 What sports teach us about strategy and resilience
🌟 The joy of purpose-driven projects
🔥 The power of self-imposed challenges
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📄 Show notes:
[00:00] Introduction
[03:36] How early passions shape who we become
[06:04] How consistency creates opportunity
[09:10] How early struggles fueled Jason’s competitive edge
[11:21] The challenge of being an outsider in a competitive world
[14:45] How gymnasts push beyond limits
[23:45] The mental struggles of a serious injury
[26:30] Why sports injuries aren’t just physical
[28:40] Winning alone vs. Winning together
[33:26] Measure success by purpose, not by size
[37:35] Learn to separate passion from profit
[40:18] Winning isn’t everything
[42:49] Winning is about surpassing your own limits
[45:18] The only finish line is proving yourself right
🗣 Mentioned in the show:
Future Stars Program | https://usagym.org/men/future-stars/
ADHD | https://www.nimh.nih.gov/health/topics/attention-deficit-hyperactivity-disorder-adhd
Simone Biles | https://en.wikipedia.org/wiki/Simone_Biles
Stephen Nedoroscik | https://en.wikipedia.org/wiki/Stephen_Nedoroscik
Levon Karakhanyan | https://www.linkedin.com/in/levon-karakhanyan-0841b437
Frederick Richards | https://en.wikipedia.org/wiki/Fred_Richard
Stanford University | https://www.stanford.edu/
Stephen Curry | https://en.wikipedia.org/wiki/Stephen_Curry
Michael Jordan | https://en.wikipedia.org/wiki/Michael_Jordan
Kobe Bryant | https://en.wikipedia.org/wiki/Kobe_Bryant
Tom Brady | https://en.wikipedia.org/wiki/Tom_Brady
George St-Pierre | https://en.wikipedia.org/wiki/Georges_St-Pierre
The Way of the Fight | https://amzn.to/400RO7U
👤 Connect with Jason:
Twitter: https://x.com/JasonShen
Website: https://www.jasonshen.com/
The Path to Pivot: https://amzn.to/4iFFRfh
👨🏾💻 About David Elikwu:
David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.
🐣 Twitter: @Delikwu / @itstheknowledge
🌐 Website: https://www.davidelikwu.com
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📜 Full transcript:
David Elikwu: I think that you have had a really interesting background. In particular, I think sometimes when I talk to people, they say to me, it seems like I've had, I've lived several lifetimes or something like that.
And I think you are also one of those fellow people that have, you know, lived, lived a few different lifetimes. And some of them for, for both of us overlap. Mine, I think, actually, yeah, most of our cycles have overlapped. Mine probably less successful in each domain than yours. But,
Jason Shen: No, no, come on. Don't do that.
David Elikwu: But, yeah, so I'd love to, I think we could probably just jam on a bunch of these things.
I probably want to start with, you started, gymnastics training from when you were like six and I think competitive from, from eight. So what was that process like? And what, you know, what were you thinking at the time? Cause I think for a lot of people, maybe you get involved in sports. This could be a uniquely American thing, in which case you can definitely educate me on that.
But I can imagine, let's say here, I'm not even sure if you're fully cognizant of the distinction between competing and not competing or, you know, like, did you have a particular vision in mind of this is exactly where I'm trying to go with this thing? And this is, did you have a lot of, you know, mental stuff attached to it? Or was this just, Hey, this is something I like doing and it's fun and I want to spend time doing it.
Jason Shen: So it's a couple pieces to this. I was a really rambunctious kid, you know, I was diagnosed with ADHD at some point. I was making trouble even in preschool in China moved to the United States and I was three years old to join my dad and my mom. We grew up in Boston. My mom was a gymnastics competitor herself in China. And then she sort of majored in like, sports physiology. And so she was like, teaching at our local university in China, various physical activities. And so when she came to the United States, she like had a cashier job at one point, but then she started teaching gymnastics. You know, I was kind of going crazy in the playgrounds and she didn't really want me to do gymnastics at first. She felt like, it's a tough life, you know, she's thinking about a time in China, you know, injuries can occur. And so she kind of wanted to keep me out, but then she saw me trying to do like a backhand spring and like from some kid who was doing gymnastics in school. And I was trying to do it and she's like, Oh my God, you know, this is, if you're going to do it anyway, you might as well do it in a safe place. Plus it's more affordable when your mom works there. You love with a employee discount, just kind of stick you in a class, right? Like no extra sort off the back and just goes by. So it fit a lot of checked a lot of boxes.
I settled down, right? Like having that physical activity exertion was really good for me. You know, for the first two years, I was just playing. I was just having fun. You know, you're six. The thing about gymnastics is that it takes a long time to start doing interesting things. I mean, you can just kind of like jump in the pit and roll around and that's fun, but you're not really doing gymnastics, you're just kind of playing on a playground effectively. And, you know, it takes time to learn how to play basketball, play football or, you know, soccer, what have you, all these sports, but, you know, after a while, kids can, if you can run and kick a ball, you're playing soccer, right? Like, kicking is not like that crazy.
So with gymnastics, First two years was just like, all right, can you learn the basics? Are you even good enough to do this? Do you have the flexibility, the strength to do this? It takes like, years to even build up some sense of like error awareness physically, where are you in space? You know, knowing all these things, understanding all these things is important, so I didn't start competing till I was eight. And you know, people just go out to competitions and you have these small routines that you put together. And I think for the first year or two, it was like, I wasn't anywhere in particular. I was sort of in the mix. Like sometimes would place in a meet most, you know, top five or six, or sometimes even eight. We get a medal on that. Maybe I'd get on one event. There are six events I would medal on, or not even metal, but ribbon on one of them, right. Cause you'd have like top three, get a medal and then like top eight, get like little, little color ribbons.
But you know, I think between the ages of nine and 10. I started to get a little bit better. And then between 10 and 11, a little bit more, I went back to China at one point over the summer, my mom kind of like put me up with some of the, I went back to China several times actually. And my mom kind of like hooked me up with some of her old teammates who are now coaches and I would like train in China and do a lot more like, form execution, basic technique. And so those summers would always like, help me get better. And so when I turned 11, though, I participated in a program called future stars, which is meant to be talent development right now. You understand what it is. So you're like, Oh, okay. So we've got these sort of top tier folks. You've got the national team, got the junior national team, but they wanted to do what they call the junior developmental national team. So, that was like 11, 12. 13 year old kids. And so it was a special program. You had to like, learn certain routines and train those. And I ended up placing and getting into this like developmental national team program.
So that was sort of like the first sign of like, Oh, I'm competing nationally against other kids all across the country, flying to competitions to sort of do that. Now, granted, there aren't that many male gymnasts, right? Like, to be the fastest runner in your state is like, a big deal, right? But, you know, there's just not that many people who are doing gymnastics. So the pool is smaller, but, you know, it's still notable that I got the chance to do this. And this was like a special program. You had to like, spend time training for this. So again, but it sort of put me in that place where I'm like, Oh, I am pretty good. I could do this and yeah, I'll stop there. But that's sort of like the progression into competitive.
David Elikwu: And I want to keep going with that story, but there's two other bits that I'm interested in just thinking about your progression so far. One, like this is obviously one lane where you're finding some very clear competence where the more you do it, the more you're realizing, okay, this is something I'm actually good at. This is something I could pursue meaningfully and, you know, regardless of the number of other people competing in this sphere, this is something that could be uniquely your own. Were you also doing well? Like in school, in other, other domains. I know you mentioned getting in, in trouble early on. Was it something that, Oh, actually I'm generally quite competent, or was it like, this could be the one thing.
And then also, I don't know the extent to which this connects, because you mentioned getting in trouble. I know that for me, so I was also a first generation immigrant. We came from Nigeria and I think that was also a connection as well. It might be more on the education side specifically, because I remember being ahead when I first came here and we moved around a lot, you know, you're
Jason Shen: How old were you when you first came?
David Elikwu: I was something like seven or So
Jason Shen: So you had already done some school? Yeah.
David Elikwu: Yes. Yeah. Yeah. So I'd already started school. And I think that was what was frustrating me because I was learning stuff I'd already learned. And then also when you're moving around, sometimes they will put you like, I remember we moved from South London or Southeast London to North London. And then they made me sit out the rest of that school year because it was like, Oh, you don't want to join a whole new thing in the beginning of this year, why don't you just join at the beginning of next year? And then the next year that I joined. They were like, Oh, and you should also be with your age mates. So now I'm doing for almost the third time, this exact same thing that I've learned. And I was just bored.
So from that point on, I don't think I barely paid any attention. So I'm interested in like, from your perspective, especially because you were going back and spending that time in China. Do you feel like you Instantly integrated.
Cause most of the Asian Americans that I know are actually second generation, like very few, just again, maybe it's a limited sample bias, but of the ones that I know, most of them are second generation where their parents came. And so they do feel this connection even to each other where it's like, Oh, we're all growing up here. Like I was born here. This is my life. But because you didn't, and then you're still going back, do you feel like there was some outsider or misfit energy there as well?
Jason Shen: Yeah, it was like a, it's like a half step, you know, I wasn't born in the United States and I was very clear that, you know, even with a lot of these things, it would be like, oh, you're, you're on this national program, but technically you're not, or like, if you. They started to become more aware of that, and they've had like little stars next to your name to kind of indicate like, okay, but if somebody else is behind you, and they would qualify the national team, like, they'll get it before you, you know, because you're not technically a citizen.
So that was something that was made aware for me. But on the other hand. I don't really have a lot of memories of China as a kid, as a three year old, you know, that just wasn't really available to me, but going back certainly kind of like reintegrated me into Chinese sort of culture to some degree. You know, I think even being seven or being 10 like, it's different. And then some people who like, I have a client who lived in Asia until college, you know, and so it's like, 10 years later, she still doesn't feel like she's American, even though he's been in the country for quite some time as an adult.
So, yeah, I think I was somewhere in the middle in terms of that. In terms of my whether I was good at other things, I did reasonably well in school. We grew up in a, you know, my parents fought really hard to try to be in a suburb that was considered investing in their school systems. So I went to public schools, but they were reasonably good public schools and I never understood why it was such a big deal that my dad was, I was talking about public school versus private school, and then it was like, Oh, and a lot of other places like, people just go to private school because of the public schools aren't that good depending on where you're coming from. So for me, I went to public school, and I was like in some of the early advanced math classes, but I struggled in some of the other areas. At one point, we were even talking about me skipping a grade, but they felt that my social skills were not quite there, and that would be where I would suffer. And whenever I told people that, I would put social skills in quotes, and everyone would laugh. I now realize it's like, that proves your point, right? That you're dismissing this thing that like really is important.
So yeah, I did recently go on school. There was some pressure, like I wouldn't call my parents like full on tiger parents, but they certainly had high expectations for me and had sometimes extra work for me or over the summer. They like, really want to make sure I was like, still like, engaging in educational activities. And so worksheets and booklets and all that stuff. So, so, yeah, academics was really good. I also like saying chorus, you know, I started playing the violin. And I was doing karate for a couple of years. But you know, in that 10, 11 time frame is when I started to like, narrow in and say, you know what? Like gymnastics seemed to be my thing, dropped out of the chorus. I think I was still playing violin, but like less seriously, just didn't have time with all the classes and you're ramping up your training, right? Like you're going to the gym, maybe like three times a week for two hours. And then it's like, four times a week, five times a week, six times a week. So Monday, Tuesday through Saturday and so Sunday off. And so by the time I was like 12 or 13, I was doing like, four hours a day, five, five, six days a week, you know, like three and a half, you know, so it's like 20 to 24 hours a week. That's a lot of time in the gym. But that's sort of what it takes to kind of refine your skill and be able to perform at a high level and perform safely,
David Elikwu: Were there anything in particular that you found difficult about it? Because, I mean, this is me as an outsider, when I look at gymnasts and some of the things they do, it looks incredible. And, I mean, you get incredibly strong, you become incredibly flexible.
Does it ladder up intuitively in terms of, okay, if you get your flexibility, right. And you learn these basic things, then you can then do these things. Or does it still feel like there are certain things where there's actually a step function in difficulty, because it's very easy, everyone sitting at home watching Simone Biles or watching, you know, some of these people, I forget the guy's name, but the guy that had the glasses that was doing
Jason Shen: Stephen Nedoroscik Yeah.
David Elikwu: Yes. Yes. And you know, there's a sense in which you can watch it looking at from, from home and the amount of perceived difficulty there is to, Oh, what is that actually like, when you're there in the moment?
Jason Shen: The idea is that you try to make it feel effortless, right? And there's no one else affecting you, you know, one of the things gymnastics kind of instills in you is that like, it's on you, you're in control, you know, it's about sort of like how you feel as you're doing the movement. Unlike other sports where you have to like, react to what your opponent or the other team or whoever is doing something right. So it's not totally just whatever you want to do.
For me, I think it was a couple of things. I had great flexibility naturally, strength was important to me. To get stronger, you have to do a lot of conditioning. Conditioning is annoying and painful and kind of boring. So didn't feel like doing a lot of it. You have to good technique and this is often where my mom harped because she felt like the coaches that are working with often didn't have the strongest grasp of the best technique. And so they were kind of getting you to learn the skill, but you're not learning with the best form. I mean, I think when we look at basketball, for instance, like there's a lot made of Steph Curry's like, arm angle and like how high his shoulder lifts and all of these things and how he sort of like does it the same way every single time. Consistency.
So technique, consistency. And then I said form already, but there's also the form of like pointing your toes, straightening your legs, opening your shoulder a hundred percent, hitting top, you know, the handstand position. So that's where you see all these like tiny little deductions like, that looked perfect. Well, I was like, well, but he split his foot a little bit on that one move and he didn't quite get to the handstand he got like, five degrees past handstand. So those are all little marks that come out, you know, as you get higher and higher. And so like early on the form doesn't matter so, so much, but the further up you go, the more they're looking for those tiny little deductions.
And so, yeah, I think I struggled with the strength aspect of it. At one point I switched gyms and I switched to a new gym because our voice program had moved and my mom used that opportunity to like, look around for new because it's like, it's not just the one that's right near our house anymore, right? So why don't we look around. And ended up working with this other gym with an Armenian coach who had come from Armenia, where he's on the national team. He was in Brazil for a number of years, coach there and then he moved to the United States. 32, you know, like pretty young, still quite active, pretty short, short guy. His name was Lavon Krakenian. And he actually coached Frederick Richards the, one of the other men's team members who, you know, was on the team in Paris. So that's phenomenal for him. He is now an Olympic, trained Olympians who have competed. But you know, I was in the first or second year that he was in the country. And so he was very intense, very on your ass, great form, lots of focus on strength. I got leaps and bounds better in that year is my sophomore year in high school.
So that was, you know, an example of where like the right coach who puts the right program in place can really put a leap into your development.
David Elikwu: So to, to my understanding, you know, you go to Stanford as a gymnast, you're on this team, first of all, that by itself. Very incredible. But then, a few more things, one, eventually winning a championship, although you didn't actually got to participate in the final of that. And so I'm really interested to, you know, there's a lot of emotional nuance in that specifically of, okay, you managed to be on a championship team. You win this title, but you specifically don't get to feel everything that goes into it, even though you were there on the journey. And then the other part also getting, I think, two world, world records, which is pretty incredible as well along the way. So yeah, like tell me which parts stand out the most as like, these are the really important points along that journey.
Jason Shen: Yeah. So obviously there's so much to go into and I, we have lots of topics to cover, so I'll say a few things.
First of all, I don't think I would have gotten into Stanford without the gymnastics success not only just because, oh, it's a demonstrated ability, but it's like the sports program. We now see more and more how legacies, dean's list and athletes get special treatment in getting into these programs. And so I was recruited to multiple schools. All the other schools were like, yeah, if you want to come here, you're in, you know, it's just a formality of that. You just have to commit to us and give you this much scholarship. Stanford is the only one that actually made you apply, so there was still like a bar that you had to hit. But I think it was relaxed for those athletes. So I'm grateful for the opportunity to have use my athletic ability to get there into Sanford. And I know I'm a smart person, but there are a ton of like really, really smart. People at Stanford that you're like, damn, if I didn't have this going for me, this, I don't know if I've been able to cut it.
Being part of a team, up until then, I was only an individual competitor. Yes, you had other guys that you trained with in your gym, but you compete with them. You still are sort of like, going head to head with them. In college gymnastics, you're mostly focused on the team performance. Yeah, there are some all around sort of like records and things like that, but that was like secondary, you know? And so learning to be part of a team, doing team bonding activities, going to camping, all these things. Like, I think I learned a lot about how to act in a masculine sort of male testosterone culture from sports.
And, you know, up until then being Asian American, I wasn't as, I had some groups of guys that I was part of, but we didn't have that kind of like, back slapping bro nut sack tapping culture that like most a certain kind of, Western male American culture has. And that was important for me, even though, you know, there was a lot that I struggled with as well in that.
And then the last thing I'll say is yes. I injured my knee in a sort of very severe injury in my junior year. I was out for, dislocated my knee, tore all four ligaments, had multiple reconstructive surgeries, unclear if I would return to competition. Eventually did, but only on the pommel horse and the parallel bars. Re-injured my knee, going into the sort of week before the finals. So I was actually out. I mean, it would have been on like one or two events had I stayed in and I would have been the first guy up, which means that like, you're really setting the bar for the following guys to do better scores than you. But yeah, it was, it was bittersweet to win. I wouldn't have been able to be part of that team if I hadn't injured myself because you get an extra year. It was also a year where I got to start a nonprofit with a number of folks at Stanford that I still stay in touch with that have all gone on to be really interesting things. So it's like a lesson in resilience. I'm a big one. Like, things can be taken away from you very quickly. You know, I never did another vault again. I never did another high bar dismount that I loved again. You know, that was it. It was over in an incident.
The recovery was, I was sort of earned the respect of my teammates in a way that I hadn't had before because they saw me dedicate myself to the recovery and to support them throughout the my own time when, even when I wasn't competing. And it opened the door for other things for me to, to do that I wouldn't have had time to do had I been only in the gym all the time. So you sort of learn all of these things and you have to recognize that like, You have to appreciate what you have. You don't know when you lose it. And I see this in other people, they don't necessarily, my clients, people in my family, if you don't have that kind of experience, it's easy to take things for granted or be frustrated.
Like, why can't I get this next thing? Or like, it's unfair. It's like, Yo, you don't know, like, it can just be over, right? And sports, in particular has that thing going for you. And yet, when you have something difficult happen to you, it can open doors to a lot of other possibilities.
David Elikwu: Yeah. I would love to know what you learned both from the injury and then also from. I guess sports in general, at least in the context that you did it, because I mean, again, I'm not a gymnast specifically, but it's a bit weird in that it's a kind of a team sport, also kind of not a team sport, at least when you're on there. Because from what I see, usually you're on there by yourself. Whereas I played, so I played football early on, like soccer, then basketball and then American football. And so, you know, there's a lot that I might have learned from playing American football, you know,
Jason Shen: did you play American football in college?
David Elikwu: Yeah, university. And also after university as well.
Yeah.
Jason Shen: That's interesting, like, like a recreational football league is not something I hear as much about, right. Because of, you know, the injury and just like, no players, you need to feel to like play, but that's great. Yeah.
David Elikwu: Yeah. I was going to say, I think my year was the first year we had a proper team. So we were just, we got the beginning of it and yeah, it was a great experience, but I think, okay.
Two more connections to your story. One, I think we're both captains, at least what me from my second year and you in your final year. And then the other thing is that. I also had an injury and I think this is why I was specifically asking you about your injury because I don't know if you'd been injured before you had the knee injury, but I never had
Jason Shen: Some injuries, but yeah, nothing so serious. Yeah.
David Elikwu: a serious injury before. And genuinely I cannot explain to you I did not take it very well. And it's a bit shameful in retrospect, but it was seriously depressing to me. Like, I think in my head, the self image that I had was, and especially American football, you know, it's quite rough. You run around, you hit people and I played defense. I was a cornerback. So this idea that I can just do stuff and it had just never happened that I just could not, you know, did
Jason Shen: I'm strong. I'm powerful as a default. That's just it.
David Elikwu: I just could not play. And I had GB trials, which I then couldn't go to a GB as in like, for the great Britain, the great Britain, like a university level team. And I just couldn't go. And I had this cast on my leg. I'd never had a cast before. First I had a plaster cast and then they changed it to an air cast.
And because it's a plaster cast I lived at the time, I was renting this tiny little place with a friend and it was like above a chicken shop. So it's upstairs and it was raining a lot and the entryway to get up there is outside. So basically I could barely leave the flat because of the rain, like I can't get this thing wet. So I had, I was just inside and it was just such a miserable time. And I don't think I responded well at all. It wasn't like, Oh, I just bounced back and I was like, Oh, I can't wait until I get back out there and you know, whatever I was just, just a mess.
So I'm interested to know from your perspective, what that was like for you. And then also, I guess within the context, generally, very often people say, Oh, you know, if you play team sports, translates very well to success in work or in business, and there's loads of lessons that you can learn.
Jason Shen: So injury wise. Yes, it's one of the reasons why I think sports is important as a developmental thing for kids is like, you learn that you are can't win all the time that you do lose. And you know, injuries can happen, other things can happen. Stuff is not always in your control and it's very clear when someone's like, way better than you're just like, okay, they're really good, right? And that's an important lesson to learn.
For me, the injury because I had other injuries, I knew and I had teammates who had shoulder surgery, even in high school. So I can consider myself quite lucky that I'd never had a serious injury that required surgery. So when I actually did injure my knee, I was like, Oh, you know what? This is my time. This is when it was going to happen. You know, like this, I've been lucky up until this point and now, the bullet did hit me. And I was a hundred percent committed to coming back. I sort of, I don't know, watched enough sports movies or like experienced enough of that where it's like, okay. I was immediately like, all right, I'm on the comeback train now and like, people are going to say stuff and this is going to be like, the inspirational lifetime movie that they're going to play about my life later.
So I really went in with that mentality and, and to some degree, I was a little bit too gung ho, I did some stuff that like probably wasn't great for me. I like did a charity walk and in my knee brace and like, sweated into. My stitches and then like, got infected and, you know, that probably set my, you know, return back by some time.
So for me, I don't know, I was already kind of like, in the mindset of like bad things can happen. And when you do, you have to really like work to like recover from it. So that was my mindset. And I know that that's not everybody's mindset, but that helped me a lot. But it is a risk for athletes to get depressed. That's definitely a thing that can happen and does happen do, especially if it's chronic and they can't be like, they never sort of get to quite the same place, but it's sort of like, not a clean break. I had a very, I have a video of it. You know, it's like, very clear, like, something happened, you know, so that's what I'll say on the injuries front on the sports front.
I have this theory that there are sort of 4 types of sports, but really kind of like 3 major ones. It's side by side versus head to head. And then team versus individual. So side by side versus head to head like, weight lifting is like gymnastics. There's no other person, everybody goes up and there's maybe some minor strategy around like, how many weights you're going to do. Cause they did this or whatever. But you're just going up and lifting as much weight as possible. Pole vault, Shot put all, you know, a lot of the track things. Then you got like, running where there's like, a little bit of strategy on like when you're going to pace your, so there's sort of like, it's a spectrum. It's not like a clean cut.
So that's all sort of side by side. Then you've got head to head, the boxing, tennis, wrestling, there's like you and another person. And it's like very explicitly clear fencing, you know, whether you are facing off somebody else. And now it's about strengths and weaknesses and like, avoiding your weaknesses, hitting their strengths and like, adapting to what's going on and changing strategies mid way through the competition to sort of respond to things. So there's like, certain things you get from that.
And then there's, of course, team sports. And so most team sports are head to head, you know, you're playing soccer against another team. And so the ball and so now it's about team cohesion and like, how much you have your own personal strategy. It almost, sometimes it matters what they're doing, but to some degree, it's also like, can you just execute your own strategy really well and not devolve into, like, who's supposed to have the ball and, you're not doing the right thing and like, if you can just crisply execute your own play, kind of like, doesn't really matter until it does.
Well, you got synchronized swimming, you know, like, I can't think of too many other sports that are like, you do a thing as a group and then they do a thing as a group. Cheerleading maybe, I don't know, like some, something like that, right.
But with individual side by side, it's really just about you. And you feel like you're in total control. You almost teach yourself to ignore what other people are doing. It doesn't matter what they're doing cause they don't affect you. Now in, in the business world, like what other people doing does affect you, and it's not to say you should get overwhelmed by that and get to focus on the competition, but like you exist in an ecosystem of the other players and you need to understand that. Like, how are you going to fit into that existing system. You're not just a floating entity, right? And you also don't really have to adapt to other people. It's just about you. Again, like, when things change, you have to change with it. And so I think there's a lot that I learned about stepping up when you are afraid, the importance of doing the sort of behind the scenes work to kind of be able to perform at a high level. A lot of practice and training and like the idea that you, coaching is valuable and like having someone who can even see what you're doing and tell you what you're doing. Your head is out here. It doesn't feel like it's out, but it is out, watch the videotape, your heads out.
So there was a lot of that and like, even when you think you can't do it, you can do it, at times, like we had, one of the things Lavon would do is at the end of long workouts, he'd have us do what he called max circles, or we had to do at least 73 you know, and a typical pommel horse competition may only have to do 30. But you know, you're also doing these complex maneuvers. It's harder than just doing 30 circles. But we'd have to do 73, that was his number. And sometimes you'd be really tired but if you missed it, you'd have to start over and do it again. So you're like, I really want to do it on the first try. And you like, play all these mind games with yourself to psych yourself into doing it and you're like, okay, 40, it's like, easy 50, you know, like you're just trying to bring yourself to it. And there are times where I was so exhausted and yet I was able to do it. And that teaches you something like, wow, if you can really dial it in and bring it, even when you are sort of dead tired and beat, you can still rally. And that's really powerful.
So I think I apply a lot of those into my work as a founder and now as a coach. But there were also some things that kind of helped me back the idea of not adapting of looking at the competition. And sometimes, sometimes in business, the way is to kind of like hack the system and to kind of cheat, right? And cheat using, you know, I use loosely like you can sort of shortcut things. There's this great advertisement that when Tommy Hilfiger was coming out and this guy made an ad that was like the five most important men's designers. And there's Ralph Lauren like, calvin Klein and he had like little blanks and so it's like you have to like, fill in the blank and then the last one was like Tommy Hilfiger. And nobody knew who Tommy Hilfiger was at the time, but they all of a sudden he got put on the map right? And you know, one of the like, ralph Lauren came up to the ad guy later and was like, you know how many it took me like two decades to like build that reputation. He's like, well, sounds like you did, you know, the wrong way, right? If you can just jump to the front of the line.
So I do think that in sports, you sort of sportsmanship and doing it fairly and all these things that there's sometimes in business where you do play a little dirty or you do just sort of like, say like, Oh, wow, that's, that gets you to the end result sooner. Uber was just like, we're gonna ignore a bunch of laws, rack up the fees, and renegotiate with the city once we're so popular that, it would look bad for us for them to fine us that much. That's not something I would have ever thought of doing.
David Elikwu-1: Yeah, that makes sense. I have something, I'll share two things. I'm interested to know if you can diagnose me with something, but I'm interested to know if you have noticed any difference in founders that have played those different types of sports, like between side by side and like, competitive, face to face, like me against you. Only because there are some contexts in which I do see a difference, but actually in business, maybe not. So for example, I was just thinking of different examples, just as you were talking, with running, it's quite funny. I started running this year. Like casually, I did not run before I can do sports that have sprinting running very fast, but not running for a very long time. And I've not done that at all up until this year, just a few months ago. And so that's been new. And it's been good. It's been really incredible seeing my body adapt, even just within the first three runs or so. There's some runs I did not think I could do, or I was not able to do at all. And I'm still not running very far, mind you. So it's not like I'm running a marathon anytime soon, but I think I did a few weeks ago, like just over 7k for the first time. And I was like, wow, you know, it's, it's pretty cool. You know, it feels like some growth, some progress. But what is interesting is sometimes people say, oh, are you going to do a marathon? Are you going to join a run club? Something like that. And it's so strange to me that I have no idea. Like there is zero interest anywhere in my body in doing that, because why would I go and join a run club if I'm not going to win? Like I wouldn't do it unless I knew I was going to be in the first, whatever the first group or cohort of people. And not because, Oh, I have to win, but just because. Like I, why would I do it so I could be like in the middle of the pack, you know, it sounds terrible when I, when I say it, but I think that was genuinely the thought that was in my mind. Like, why would I, I could just do it by myself. There's no difference. It's different from maybe tennis where it's like, you have to play with other people in order to get better. You can't just do it by yourself. With running, I can just run by myself. When I know, like, I'm not going to sign up for a marathon until I know I can run a marathon. Like I'm, I will have already done it before and got a good time. Then I will come and do it in public and get a good time. You know, why else there's no other, it doesn't make sense to me any other way.
So there's a sense in which just as you made that distinction, it made me realize a connection there where I was like, Oh, perhaps it's because I play competitive sports where it's like me against other people. Not that I am intentionally thinking that way, but maybe there is that connection there, but I do find that actually in business. I don't know if I always think like that. I've run a lot of the businesses that I've run that have not been like, big startups have all been small businesses. And I've been quite happy with that.
I remember I was interviewing for a role or something at one point and someone asked me, like, they noted, Oh, some of these businesses that you've run, they said something like you know, but they failed or they didn't work or something like that. And I was like, No, they didn't. All of these businesses did just fine. Like, every single one of them, a few of them were six figures businesses, but they all did exactly what I needed them to do. I had a travel business. I wanted to travel the world for free. That's exactly what I did. There was no, I wasn't trying to turn this. I mean, eventually I did try and pivot it to being a tech platform and then the pandemic happened. So that didn't work out. But up until that point. This was just, I want to travel for free and I'm going to organize some trips. People are going to go, you know, that was great for me. And then I ran like a coffee and wine business and things like that. That was more like social impact. So it was specifically because there was a story we were trying to tell about farmers in Africa. So we sold a coffee from around Africa.
And again, like, that's all I cared about. I don't care about. Oh my gosh, this has to be every time people kept asking me, am I going to raise money? Am I going to do and I did a pitching competition thing and people were like, oh, you know, you should speak to this investor. Like I don't care. I have zero interest in doing all of that stuff. So, yeah, point being it's interesting that actually in a business context I don't think i've always had the mentality that every single thing I do has to be some rocket ship startup, but I can do a business for fun I just do it because I like doing it or there is a goal and as long as it achieves that thing. I don't really care about it doing anything else.
Jason Shen: Did you have any engagement with the arts? Like, creative practices. Did you have any of those growing up or in your life now?
David Elikwu-1: Yeah, mostly like now just writing. But I also did used to do some arts when I was younger as well.
Jason Shen: What kind of arts?
David Elikwu-1: I mean, not, not great art, but just like some painting and sketching. So I would draw, draw a lot. I probably still have some, some sketchbooks somewhere down there. And also, I guess, design, because that was actually my first job. I self taught design when I was like 13, 14. So then I would design stuff online and then that would lead to making websites and stuff, and then now also photography.
And funnily enough just as I think about it, I would also say that these are things I have learned not to do for money anymore, because I did, and it sucked because any time. I do it and unless I would just have to charge a lot. If I can't charge a lot and I'm charging even a reasonable amount, it would just feel like pain because it's something I do for fun and I just enjoy doing it. It kind of perverts the thing that I'm trying to do.
Jason Shen: It can be challenging to find that balance. Yes. I ask because I think sports is only one of the many lenses that we have in the things that we do, right. And of course, the more involved and engaged in like part of your life. That was the more that may shape how you think. I do think people do come in with natural temperaments of being more competitive and wanting to beat other people or not versus beating yourself or what have you?
And I think what you talked about with your businesses feel more like creative pursuits, right? Like you have a vision for what you wanted to take a picture of or draw or what have you. And when you do that, you're satisfied, right? When you make the travel business allow you to travel around the world, you're satisfied, you know, like, I think it's not activating the sports part of your brain because it's just like, it's more about the creative expression of your business skills. That's what I would say on, on that front.
As a amateur diagnosis, you know, and then on the running front. Yeah. I mean, there's something about this idea that you know, whenever you're in a group, maybe you are competing versus training together, right? And the idea that like, hey, you don't have to be the best. And in fact, it's better to be in a group. That's where you're not the best because that's where you learn more, right? So there is a sense of there's like a performance culture or like, if I'm with others, I'm always performing versus like, this is a place for me to learn and grow and be okay with not being the best. Or maybe I go and then this helps me become better. And then I go somewhere else and I stunt on everybody. So I don't know, I think those are some things that like come to mind when I hear you describing what you've done. Yeah. Or where, where your mind's at on those fronts.
David Elikwu-1: Yeah. That's a useful diagnosis actually. And I think you're right because when I run by myself, it is more like, oh, I just do it for myself and I compete with myself and that's fun by itself. If I was to go and do it in a different context with other people, then it would become this other thing.
Now like, either I'm going to be good at it or I'm not going to be good at it. Whereas by myself, I can just have, I just try and beat my own times. And I enjoy that game a lot more. I don't want to turn that into, there's no marathon. There's no, I'm not doing any of that stuff. Unless, I already, I've run several marathons by myself and I know that I can just do it. And then, and then I will go and do it with other people.
Jason Shen: Right, right. Yeah, I don't know what that is because I mean, even with your various sports teams, I don't think were you the best player at all times on all the teams that you're a part of? Or
was that
David Elikwu-1: Probably? not. but there was still the I would want to be, you know, like I, I want to be like at my position among the best to the extent that I can, or at least I'll train with that,
with that intent.
Jason Shen: Yeah, yeah. No, I it's it's fair, right? And I think some people really enjoy beating others. They need an opponent or a rival to kind of like egg them on. And as soon as that's gone, they're sort of not in it.
And other people that's not necessarily as motivating, you know, I think of, so two examples, Michael Jordan. Famously sort of like, and even Kobe too, and even Tom Brady, as he's talked more post retirement, they're fueled by resentment and being like, oh, and I took that personally, you know, like, the whole joke was like, everything is Michael Jordan taking things personally and then like wrecking somebody else, right? It's like, dude, I, I just said, nice job. So that obviously worked for him and also as a challenge for him in other ways. And then, if you look in MMA, which is like clearly a fighting sport where you are literally trying to beat the other person in the submission. I think of like, one of the best fighters, George St. Pierre, a Canadian fighter. I read his memoir, you know, I saw him in retirement. He loves the sport for as a sort of like, in the beauty of it. And he sort of doesn't love the competition of fighting. He loves training. He loves, you know, he's still training. He's still learning and but he's just like I don't need to keep fighting or come out of retirement to like beat somebody in particular. Like, sure. I'm sure he's had, he's had his rivalries, he's had his opponents but it was more about like, the art of being a martial artist as it were.
So obviously, you can do any sport and kind of have different mentalities that come out of it.
David Elikwu-1: Yeah, it's interesting. Just as you were saying that, I was trying to think of, you know, how some of that applies to me. I would definitely say, as the caveat, I think I care, I don't really care about beating other people. I don't care about whether you lose. I care about me not losing. Like I, yeah, I don't want to lose. I like, you know, winning or just doing things. Well, if you do things while you do things to a certain level, that's the most important thing. I don't really, whatever happens to you or to someone else, you know, unless we're on the same team. I don't really think about that. I just think about us and what we're doing and whether we achieve the things that we want to achieve.
Jason Shen: Yes. and to come back to the records thing that you asked me about the world records, like, I don't consider myself actually a very competitive person. Although then it's like, well, what are you talking about? Like who, who goes and sets for records. But it's like, for me, it is like, being the best I can be. If that ends up being the best in the world. Awesome. You know, it's more of like, I don't care that other people are worse. I just want to be the best, right? Like kind of what you're saying, right? It's not, it doesn't matter to me that, that I beat the previous record holder, I don't care about him at all. Like, good for you. You know, like, I just wanted to do this to do my best. And if my best is also the best in the world, like that's, that's meaningful to me. Personally, it gives me something for my ego, you know, especially I think the fact that I didn't get to be in the finals may gave me a lifelong desire to continue to prove my physical prowess in other ways.
I did train and start running and I did run a marathon, you know, not very well, but I did it, you know, like I compete in CrossFit, you know, I challenges world records. Like I had a CrossFit challenge in my gym where we were doing a bunch of pushups every day. And at the end it was like eight minutes, as many pushups as you could.
And I was really frustrated because I worked out earlier in the week pretty hard and I was still not fully recovered from that. So I'm doing it on that day. I was like, this is not my best come on. And I was really disappointed with my, with my result, which was like 170 pushups. And I was like, just going to send us in a little embarrassing.
And then it turned out like the winner got 180, you know, so I was like, not that far off right now, max. I'm like, if I was on a fresh day, whatever, I probably could have done that. But you know, that's just me. Yes, I do want to win, but it's not about beating somebody. It's just like, I would have liked to do better for myself. And if that ends up being everybody else sweet, right.
David Elikwu-1: Yeah.
I want to get into some of your startup stuff, but I'll share one more story just from, from my side, just because it resonates with what you were sharing and I think you'll, you'll understand.
So the, probably the closest I've come to doing a marathon and it's funny because when I tell people, they just assumed that I was doing it as part of a groups, like some organized thing. So one day, honestly, this is maybe just revealing how psychotic I am, but I was reading and people were like, Oh, you should do 10,000 steps a day. And I have no idea exactly what the thought process was, but at one point I was just like, what if I did a hundred thousand steps and then I tried to look.
Jason Shen: What?
David Elikwu-1: Yeah. I tried to look online and see, okay, have people done this? And I couldn't find, I found maybe three examples, like on Reddit or somewhere where people had done it, but never. consecutively. So I saw one person that had done it where they were doing like laps and they would just do a certain number of laps through the day, but they were doing it in between doing other things. So as long as they came back out and did like another, like two or three laps, then over time through the day, then it would accumulate to the a hundred thousand steps. And I saw one other person that did it, but they did it in different modes. So they would do it like some on a track and then some walking like, outdoors and then some at the treadmill at the gym. So again, like lots of different modes. And I was like, there's no one just done this like nonstop. Just like you leave your house and you just do it and you come back.
So I was like, okay, so that's what I'm going to do. So I kind of figured out a map and the hundred thousand steps is roughly like 80 kilometers, 81 kilometers. So it's, it's basically like two back to back marathons, but walking. Yeah.
Yeah. 50 miles. And it was not fun. It was probably one of the worst things that I've done and I only gave myself four weeks to do it. I don't know. I just picked a day and I think I'm also the kind of person where, once the thought has entered my mind, I am now, I will just bully myself into doing it. Like, I, I will know if I back down. Like, nobody even knew at that point. Like, but the thought has come into my mind and I now know that I
Jason Shen: Then you walk around being like chicken.
David Elikwu-1: Yeah, exactly.
Like, that's how it would feel. Like, I thought about doing this and I probably could have done it and I just didn't I decided not to do it That would eat eat me up. So I said I'm gonna do this thing I'll use it to raise some money for charity, but I was mostly just doing it because I wanted to do it. And I just did it, yeah, completely by myself. And it's so funny when if it ever comes up and people were like, oh, is this part of some you know big thing? I was like, no literally just by myself for almost 18 hours. Just
Jason Shen: David, I, we are, we are on some spiritual level really connected because I, I just feel that. So, but I, I find that story so funny. So, but should we, should we change gears? Should we change
David Elikwu-1: Yeah, yeah, exactly.
Because I wanted to ask about how you got into building and like where, what was the first seed of you then building something, I know you mentioned the charity thing, but the idea of, I don't think it comes naturally to everyone, especially to some immigrants in a sense, you know, you do get some prototypes of immigrants coming in and they're builders and they have small businesses and things like this, but then you also get.
The other type of prototype, which is find a stable job, find a stable career, especially, you know, even if you go off to some sports, okay. If it's not going to be sports, go work at some bank or a law firm. I worked at a law firm, you know? So what was that part of the journey like for you?
Jason Shen: Yeah. So some context, like my parents, my dad worked in education. He got a degree from Boston University. He worked for the Department of Education in the state of Massachusetts, pretty much his whole career. So government, you know, servant civil servant, my mom, gymnastics coach, teacher, education, you know, sports kind of thing.
So neither of them had really business experience or tech experience. So coming to Stanford was like, eye open. Right. And we were sort of recovering from the. com period, just like 2008. Yeah. Right. So we're still kind of coming out of dot com and like seeds of things. Facebook was happening. There were a lot of nonprofits being founded on campus.
And I think, you know, in retrospect, there are a lot of like, wealthy, privileged kids who had like access to I'm like, how are you funding this? You know, it's crazy raising all this money. But I would say a couple of things. So one, my, my business understanding was like zero. Like I didn't start any business in college or in high school or anything like that.
And I, I, you know, money was sort of like this, like, Ooh, a little bit. And distance, you know, and that was the culture my parents had growing up with me. So I had to learn a lot from, from on my own. The, the, the sort of two things that happened. One was I had this idea to write a book or to create a book that was like, I was going to call it a Stanford identity or the Stanford spirit.
And I collected these quotes, like I'd written to some columnists in the daily who had, you know, I tried to partner with her. She ended up not being super involved. And so I ended up just doing it on my own. Yeah. I got it, you know, printed and sold copies to the Sanford bookstore. So that was the first time I was like, Oh, I just had this idea.
And I like got people to submit. And then I like, you know, use like print on demand. And I got a check from them for 50 copies. I was like 300, you know, something dollar. I was like, this is amazing. You know? And I was so excited. So that was sort of like the first seed of like, you can just think things and then do them.
And then there was this like week long competition that was happening to like, you know, use Post it notes in a creative way. And so somebody sent out an email and I was like, I want to be involved in this in some capacity. And so we use the Post it notes to like raise donations for. And, and we ended up like winning one of the awards for the competition because we got like several thousand dollars worth of like commitments.
Of course you have to follow up on those commitments, but we, we had them. So that was sort of like the initial group of people. And then, so we'd seen the prototype of like, oh, you can start a nonprofit and like, there's all this momentum and you're like, maybe we should start a nonprofit and we started to work on that.
And we started, we built our own challenges. So. I think that was like the first real seed of like, I ended up being the executive director and we hired her an external board and, you know, like ran challenges at various colleges. And so again, there's sort of this activity, although we didn't raise enough money and have the sort of scale and momentum to like go full time or have full time, you know, executive directors and, and all of that.
And so eventually kind of. Fractured, but I ended up starting moving in with one of the people that I started that nonprofit with with a third person and we all lived together in San Francisco post graduation. And he was an engineer and the third person was also an engineer from Berkeley. So we were three Asian guys all working at different startups.
I was in like sales and marketing. And then we were like, And this guy, this guy, Calvin has sent me multiple emails. I've changed my life. One of them was the, the gumball thing. The other one was like, should we apply to Y Combinator together? You know? And and he was like even traveling at that point for six months.
So I was renting out his room, but you know, we were like, why not? Let's see what happens. And we kind of brainstormed some stuff and applied and we got it. So that really, like, I kind of like stumbled into like a golden ticket in a lot of ways. And I think that I still didn't know something, you know, I so much, I didn't know so much that was still like wrong.
With how I approached startups at that time, but that's how I got into it. And, and of course, you know, people, tech companies are starting to emerge. And so it just became more and more of a thing like, Oh, this is happening. This is possible. You know, something that you can be a part of, even if you're not an engineer.
David Elikwu-1: Okay. That makes a lot of sense. Two quick questions. One, were you working at the time when you applied to YC
Jason Shen: Yeah, I was working at a startup.
David Elikwu-1: Okay. Yes. Yeah.
Yeah. Cause I thought that's what you had said. So I'm also then interested in like, yeah, like why a startup and what were you doing and how did you get into that? And then the other question was actually going to be what idea did you have when you joined YC was that for ride share or what was that for? Oh, right. Joy.
Jason Shen: Yeah, no, yeah, no, it wasn't. So, so yeah, quickly ran out of school. I was debating whether to go to teach for America or like, do this like civic fellowship. And then I ended up taking this job as a one year sort of business manager for the Stanford daily newspaper, which was like a postgraduate job that was on campus and it's technically a nonprofit.
So it's sort of like. It did a bunch of different things. One of my mentors was like, being in charge of a P& L so early in your career is like really valuable. Nobody really understands what the job is, except other people who've done it, because it's so weird. But yeah, we were in charge of like, you know, raising advertising dollars managing the print and distribution.
We had employees, and then we, you know, it was the recession, so we actually had Cut a lot of my first real job. I ended up like executing a layout, series of layoffs and, you know, head count salary reductions for everybody, you know, including my own salary. So it was sort of like, that was like a, you know, tough introduction to business, but in some ways like.
And then, yeah, I, after that, I wanted to work in something business related, and I think I was interested in startups at the time. So, this was like a 7 person company. They were doing ad sale, digital ad sale platform. So, selling to publications. So there was sort of like an angle in which I was appropriate.
I think the founder was like, A Stanford gymnast athlete who's done some media stuff like he can sell and do some marketing for us. All right. That was his mindset. He was also this 23 year old white dude who was tall, had a deep voice, a goatee, looked older, acted and talked like he had been in the business for 10 years, even though he was the same age as me.
And I think that also was like, you know, irked me a little bit and kind of also you know, just, it made me think, well, he can, he can do this. Like, why can't I. Right. And so we ended up, I ended up leaving like 11 months into the company and he was pretty mad because he was like, you're not even going to vest your, like, one, like I told him I was quitting when I got the interview, not even when we got in, when we got the interview, I was like, I'm out.
And he's like, you didn't even get in. I'm like, yeah, but you know, I just, I don't want to be here anymore. You know? And he's like, what about the, and I'm like, I'm out. It's whatever, you know, I can't say I've had the best luck finding, you know, he did sell this company. I don't think I would have made a lot, but like, you know, broadly speaking yeah, it's, it, there, there's certain things that in restaurant, you'd be like, just stay for the, get the clef, you know, like you're already there.
Just do it. So, Yeah, so that's sort of like how I think that was the question, right? The what were you doing? Oh, and then what we were playing with. We brainstormed a ton of different ideas. It was tough to get something that we all agreed on, which, you know, in and of itself is not a great sign and was a problem later on for us.
But we ended up applying with, we had a ride sharing concept at some point, but we didn't end up applying with that. We ended up applying. With something we call re love it, which was sort of like time hop. It was meant to like resurface old photos or pictures or things you'd like, things you'd saved, kind of like rediscovery of, of past things and Facebook memories, like, you know, Apple's like album, you know, sort of like videos, all that stuff is sort of like in that it was in that mix.
That was the concept. And yeah, You know, I think they, they did like a pre interview with us where they were like, who is going to be the customer for this? How are you going to get distributed? We're like, everybody's going to want this. And they're like, wrong answer. And try it again. And we ended up saying we had a week to like come up with something else.
And we ended up coming up with this idea to do photo printed photo albums that we would sell the people off of the. Images that maybe were collected through this algorithm and, you know, Paul Graham was in my interview, Jessica Livingston, Sam Altman, some heavy hitters in this like interview and. It didn't go super well.
They were kind of like asking these questions, but they weren't like super excited at one point, you know, Sam Alton was like, Oh yeah, you know, who could have used this as like, yearbook editors. I mean, we were, you know, I was editor in chief of my yearbook and we could have used that and Paul and Jessica were like, Oh, you were the editor of your yearbook.
Oh, wow, Sam. That's so cool. We, I didn't know, you know, now they're having a little family moment. We're just like. Yeah, this is happening. What's going on? And so I didn't come out of this thinking that like, we went that well, you know, and we're sitting around my friend's house in Saratoga. I just kind of like, I was like, shit, I quit my job.
You know, if we don't get this, like, how many weeks do I, can I like, can you live in San Francisco before I have to move home and work at target? I was like, starting to spiral a little bit. And then we get this phone call and Paul Graham's like, do you want to You know, joining them were like, Oh, yeah, you know, like, of course I think that's like one of the few most exciting like moments where like your life, you know, your life is changing in an instant, right?
Like, so everything else kind of like sneaks up on your like, slowly happens. It's ever bad things, right? But like, good things rarely just happened to you. Like, mostly bad things. dramatically happened to you. When you're a kid, you get surprise birthday parties, you get like surprise, we're going to Disneyland.
When you're an adult, like nothing is ever a surprise. That's good, right? Only bad surprises. So that was one of the last, like good, like, I don't know, surprise, like you did it kind of moments in my life. And it was, it was very exciting. We got in there and we immediately wanted to change our idea to ride sharing.
And We found out later, there's a journalist who was following our batch and like wrote a whole book called the launchpad about our class of YC. And we're in the first page of that book talking about like our, we're like a prototype, typical, you know, YC company, 23, 24 year old guys from Stanford and Berkeley.
But we wanted to change immediately and we immediately started looking through different ideas and then we felt the pressure demo day. So like three weeks in, after cycling through a bunch of ideas, we ended up on that. Which Paul Graham was like, this is a bad idea. You know, I think you should keep looking.
Only poor people are going to want to care about sharing rights. You know, we're like, no, like you're wrong. Like, you know, of course. And so we pushed through, but it turns out the journalists told us this later that they had written like in the notes for us, super enthusiastic founders. Fund for the new idea.
And he even told us that at one point, which I thought he meant the new idea that went, that we pitched them. But it was actually code for, they will come up with a new idea in YC and we're funding them on the basis of like whatever next thing they come up with. Which is both of them and they were correct.
And then we ended up coming up with a new idea. So, you know, it was an unbelievable experience in retrospect. Like I, I didn't even fully appreciate what I was. Experiencing and getting, because I, you know, now I coach clients, some of whom have gone through YC, some of whom are like applying for the fourth time to YC, right?
And it's just like, dang, this is like such a a mark now that at the time was still kind of like a, Interesting experiment that Paul Graham is running.
David Elikwu-1: Yeah, that makes a lot of sense. And it's funny how, just as you were sharing that, I was realizing even some things for myself, but it's so interesting how our environment and the things I, you know, you, you've probably come across the mimetic theory and this idea that, Oh, how you build your desires, but just this idea that. By seeing things and experiencing things and being in a certain context, that's kind of how you can then develop ideas. And it's funny, just contrasting that to some of what I was mentioning before, which is some of the businesses that I had run, you know, particularly when I was younger, and I think it makes a lot of sense now in context, because I hadn't really come across Silicon Valley much at all. I know that now I hear a lot of people say, Oh, we watched what's that film? The Startup. The film about Mark Zuckerberg.
Jason Shen: Oh, show us your network, the
David Elikwu-1: Yeah,
The social network. I watched that last year. Like, I did not see.
Jason Shen: For the first
David Elikwu-1: like, so
I missed that one. All the
Jason Shen: That was extremely influential. Yeah.
So not to me necessarily, but like it, it like inculcated a whole generation. It was like the wolf of wall street of
David Elikwu-1: exactly.
Yeah. And I completely missed that.
I could have got all this inspiration and thought about trying to build a startup. But no, like me building businesses, the very first one that I did was actually importing electronics from China. It's because I tried to stop a non profit, a non profit, actually. It was a charity. I wanted to send used school books to Nigeria and I had started that. doing that. And then I realized it's extremely expensive with zero budget to send like heavy books in big cartons, you know, across the Atlantic. And so it just, it was really difficult. And I was like, where am I going to get capital? So I have to start a business. I have to do something else and sell something to get money. And so I started this other business. And then, so I think because I had that stock. All the other businesses that I mentioned to you have been bootstrapped. I just didn't even think of, why would I be raising money? Why do I need, you get the money by selling the stuff, right? Like I make the stuff,
I sell the stuff, you give me the money.
That's kind of how it works. And, you know, I have run some venture backed startups now, and that actually feels like a worse idea because it's harder. And, you know, I know that you are going to empathize with this experience and I'll let you share some of, some of yours, but, you know, even, even for me in that experience, I think you end up on this cycle of you, you raise some money. Now there's this pressure of, okay, you need to have this growth and within this timeframe. And it's not just, I mean, originally you might have, Your own impetus of, I want to grow this and I want it to do well, but now it's connected to, I've taken this money and there's a tech crunch article and people are looking and, you know, people are expecting that everything's going to grow and everything's going to do well, so you can probably start from the, the, the ride joy journey.
I think I know. I heard you mention at some point, the, the idea that I think even in the gap between, so there was the, the famous, the picture that you guys have with you know, all the YC
group
Jason Shen: yeah, the Dropbox founders.
David Elikwu-1: exactly. And I think even in the time it took for that article to come out, the, the business was already not doing as well as it was before, So I'd
Jason Shen: David, you did, you did your research, man. I love this, you know, and I know that that's your, that's part of your trademark, but you know, it's, it's much appreciated. Yeah, this, I mean, there's so much to say about it. I think. I'll, I'll touch on it and then I want to make like a larger point as to the bootstrapping versus venture backed, which is like, you know, we really didn't know what we're doing.
It was such an early time of, of you know, tech can just change the world. We can just make things, people will just use them. And then you can figure out the business model later, you know, like Facebook, Google, a lot of these companies, you know, hadn't quite figured out the business model, but then it seemed like they were starting to make money.
It was still such heady early days. Airbnb. You know, a couple of years earlier, we were like, we're in that same boat. We're going to do the next Airbnb. You know, whenever you're doing the next X, that's always like maybe a counter signal because the next X is not X. It's something else. Right? But in retrospect, we, we started with ride sharing to events like Burning Man, then we were starting to do like the West Coast.
I have met recently met a founder who has spent the last 5 years building a ride sharing company, and it's actually starting to work. And And it's really impressive because he's raised like a series A, which is like, you know, that's a pretty significant milestone. And he stayed in a tiny geographic area.
You know, we should have stuck to SFLA and just, like, crush that route and, like, figured out all the nuances of that before starting to extend to other routes. But, you know, we were greedy. It felt like, you know, you always want to say you're bigger than you are. You want to be like national, you might be everywhere.
And so we, we kind of were like all along the West coast. And then there were some people posting into other parts of the Southeast, but I don't think they, you know, there were some rides made from that, but it's like, it dilutes your focus or dilutes your energy and hurts your brand. Right. It's a lot easier to be like, if you're going to SF to LA, this is the place to go.
People can remember that. I remember having friends who would be like, Oh, I drove to LA the other week. I should have posted on your site. It's like, you are a founder, you know, we have this company, you know, this is what we do, like, and you forgot to, to like put this on there, even though you'd be willing to, you know, it's like so hard.
So I think we didn't focus, you know, I think there's some FOMO to not like, you know, to, to, to not dominating, to, to, to, to not be covering the whole. country at once. I think there was, there was a test that we wanted to run at one point, which was like, What if we you know, there was all these questions, like, why isn't this working as people that want it?
Is it that there isn't enough inventory available? Like one test could be what if once in a while people search something, there's immediately a ton of the best, all these rides going in that direction, different people, they all look friendly. There's like ratings reviews. It's all nice. It's all set up.
Will they book it with that, with that sort of perfect result? Or would they still be like, eh, I need to think about it. Maybe not. And we never pulled it off because it felt deceptive, right? It felt like wrong to sort of do that to people. But on the other hand, it would have answered a ton of questions.
If like people, 90 percent of the time would hit book it. Okay, we got something here. If like 10 percent of the time people still booked it, then you're like, even if we do all this work, People might still not do this. We really gotta get out of this. You know, we never did it. Maybe we didn't wanna know. So there's a lot of like, you just can't help the, the sort of, some of the youth and inexperience and naivety that, that, that I had.
And I think now as a coach, a lot of it is like how help people, they still have to make their own mistakes and make their own decisions and see those through, but also kind of like nudging people in certain directions, giving people some. Sort of like, edge case thoughts to kind of help them make better decisions or more informed decisions.
Yeah, so that's, that's part, you know, there was a lot and I wrote a whole article about why I don't think it worked out. But you know, what I wanted to say more generally about bootstrap versus venture, Back because now I run a bootstrap company. I run a coaching business. You know, I'm the only employee at, you know, probably hired an executive assistant at some point, but, you know, it's, it's really just me.
It's freelance business, but, you know, I see it as like a bootstrapped company. Most businesses are bootstrapped companies, right? Like, historically speaking, most businesses were bootstrapped companies because, you know, you just. It requires credit lending, like contracts, all these things to make a non bootstrap company possible, right?
But on the other hand, venture is also not like invented in the 60s or whatever. Although that's sort of when the term venture capital started to emerge, it goes back to explorers, colonists, you know, trading companies, right? The East India trading company various. Ships like Magellan, like they, they, they went to, you know, Christopher Columbus went to the, the queen of Spain.
Right. And said like, give me money and boats. And I will go and find a bunch of gold and you're going to get a ton of it. Right for the, the, the, the, I'm taking the risk. I may die. You may, I may come back and find no gold, but maybe I will come back and find a ton of gold and that's going to be sick for you.
You know, and you're going to get to name this place to and other stuff. Right. And, and, and like, they've negotiated deals of like, you know, what percentage of the revenue would they get? Like, who would be the governor of this place? Like established routes, taxes, like all of these things were in the contract, just like a term sheet.
You know, they really had all of that stuff worked out in the, okay. You know, 1600 1700s. So but it requires a high risk high reward high failure rate thing it's a venture and and you know, it doesn't Always or usually work whereas more bootstrap companies can work, at least on some scale most venture things.
It's like you're, you're taking the money because you cannot bootstrap this because of the level of, you know, investment needed. Like, I, we need to build a ton of technology. We need to build all these ships, you know, we need to hire all these men. You need to front load a lot of investment. But on the backside of that, you're going to get a ton of return.
Right? And the risk profile has to be that the return has to be so high that it makes up for the fact that a lot of the time you're going to lose your shirt doing this. So, you know, what I think Nassim Talib says this like, Entrepreneurship is sort of like not a great economic gamble for the individual, but it's a great thing for society because society benefits from the entrepreneurs that succeed in and come up with great, you know, tools, whether it's like Google or, you know, Amazon and Netflix or what have you.
And, you know, the individual entrepreneurs or explorers who fail and die or, you know, go bankrupt or whatever, that's just the cost of getting to those great things that we now have.
David Elikwu-1: Okay. I am interested to hear more about the lessons that you've learned. So obviously as a coach, a lot of the, the things that you're able to help founders with and, and execs with come from your experiences and you've had both. And I think this is why it's particularly interesting, both experiences as a serial founder, having built multiple startups Having to learn a lot along the way, having to pivot, having to, and then eventually having some that were acquired but then also as a PM and working within larger companies, work at Etsy Meta or Facebook, et cetera. And so I guess it's, it's kind of two questions. One, I'd love to hear more about, Kind of what you've learned from some of the, the other business experiences that you've had as building startups, but then also the difference between the two. And, you know, now you get a lot of young people that think, Oh, I want to go and build the next big startup.
I want to go and build the next big thing. But I think you're also getting a class of people that are. Like, actually there's an also a very safe and viable route to success, which is just going and being a PM at Meta or just go and be a PM at like any big tech company, whether you're going to get a large total comp, you don't actually have to take the risk of trying to build something. You just have to figure out how to climb from, you know, L4 to L6 or, you know, whatever the leveling system is. And as long as you Collect your RSUs, you can end up becoming quite wealthy. And that's also a pathway that might be viable now. And so I'm interested to know. Yeah. Cause you've had a little bit of both of those experiences, what you've kind of learned from that.
Jason Shen: Building something from nothing is, is very hard because there's already so many alternatives out there. Right. And you know, you're always. Asking yourself, like, even if there are not direct competitors, people have already figured out a way to solve this problem, like every good business solves a need that already exists, right?
Libraries existed to answer knowledge or their other search engines before Google, you know, people could rent DVDs and had other ways of entertaining themselves before Netflix. But that core need of like, I want to be entertained. I want to know stuff. I want to find stuff is always going to be there.
And if you can do it better than, you know, you can get somewhere, but it's hard to do it better than the existing alternatives because the existing alters have had a lot of time to kind of optimize things. So the only way to really do that, that one of the lessons is that focus, that point about focus, like you can't be better than everything else.
You know, for everybody, but maybe for a very specific set of people or specific geographic or specific use case You can be better, right? I have a client who was trying to avoid going up against some major competitor and it was like, but that's where the money is. And that's where all the people are, right?
Like, you know, you don't have to be better than them at everything. But I bet there's a subset of people who are like, man, this is so much money. And I really only use these five things. They don't even do those five things that great. If you could figure out what those five things are, do just those five things better, sell it for half as much, you could make some money, right?
And you can find those people and be like, Hey, do you use this thing? Do you hate how it doesn't do X? Like. This could be for you. Right. So, so it is sort of like lean into competition, lean into like, not to say crowded, but like existing, I just met a founder who was building a password sharing company and was acquired by you know, a large SSO provider.
And it's like, how many more passwords is like, he was like, to be honest, there are more, you know, and he was doing, he was working on young people and like recent grads and college students. That's a sort of. It's own kind of market, right? Be the first, your baby's first faster manager. Right. So, so that's one thing it's like narrowing in so that you can actually be a lot better than the existing alternatives, leaning into places where people already spend money, you know, okay.
So as I made another analogy at one point with a client where it was like, he was trying to get people who didn't use the product to use, His product, which does certain things better. And I'm like, why don't you go to people who already use the existing product? It's like trying to convince somebody.
Who doesn't own a car to buy a Tesla versus someone who owns a Prius or you know, some, a Honda to buy a Tesla. Like what's going to be easier. They've already bought into the idea that a car is valuable, right? You don't have to also convince them like that you should own this thing. And it has like, you have to like take care of it.
And he's parking spot, this is how you can transport yourself. So yeah, competition can be good. Those are some of the thoughts I have on, you know, of many for, for building things for, for being a PM. It's a very, there's some similarities, but it's actually quite different, right? You need to exist in an ecosystem with a lot of other people.
You need to play kind of nice with a lot of other people. Become known. Get sort of information early. Be on the right projects. So much of being a PM is being on the right projects that actually take off. I would argue that the rate of success of internal company of like internal teams inside larger companies is similar to venture.
Right. 10 percent of them do really well. 20 percent of them do okay. You know, 60 percent of them go nowhere. Right. And that's okay. Like the whole thing is that the big successes really pay off for everybody else. Like threads is like the latest big thing that meta is doing. Before that, they grant, they grinded their way to the Ray Bans and like the, the headsets that still aren't killing it.
Right. That's in the 20 percent of being okay. And before that, what they had right. Stories like reels, you know, like, and then there's a million other projects that like
they did a
David Elikwu-1: TV,
I still remember that,
Jason Shen: the TV portal that, you know, gone, you know, like, shops on Instagram or whatever, gone, you know, like so many things that they worked on.
They had a subset competitor at one point, they were paying people to like, write a newsletter on Facebook. Gone, you know, but some people got promotions out of that. But like, for the most part, it's like, kind of like, okay, you know, that that's, we're not going to like send you up the ladder for that one.
So being on the right project really matters. I knew an engineer at Facebook who had been there for years and had never had anything launched fully to production. Like it only existed in their experimental tests. Now that sounds terrible, but he got paid for four years to do that. And some of his tests probably reached millions of people, maybe even tens of millions of people, which many starts will never get to, like even throughout their entire life, even if they are successful, right.
So it's all a matter of scale. So, so yeah, it is a somewhat different skill set. It's, it's more political, which I used to think was so terrible. Now, going back to my concept of social skills, like. I realized it's like everything is political. Everything requires understanding and relating to people for the most part.
And, you know, PMs in particular have to be really skilled in speaking to a lot of audiences, helping a lot of people, you know, like, Building a deal, right? Like a coalitions, like a bill where, like, everybody has to have their thing so that that it kind of like, can get cleared and get all the check boxes and pass through.
So it is a, it is a pretty different skill set. There's, there's relevant, you know. Thinking and, and, you know, design sentiments and engineering, like, understanding technical know how that is helpful in both contexts, but the orientation of the mindset can be quite different.
David Elikwu-1: sure. How do you navigate? So for example, when you were talking about building things as a founder. the idea of, I think the, the thing holding a lot of people back in that context will be, oh, it looks like people are already building things in this space. I want a big sexy idea that looks new. No one's come up with before. And, oh, you want me to build something that looks similar to this other thing? There is a common criticism, which is something along the lines of, oh, you're just building a feature of this other thing. You know, they could kill you overnight if they just build this thing. And interestingly enough, I don't know if this connects directly, but. went on a journey with a, with a startup that I was a co founder of, which had been its own, its own incredibly interesting journey. But essentially, you know, a big part of the premise was we are building something. There are already incumbents in the space, but we're building in a different geography. And yes, absolutely. They can launch in this geography, but there's inherent problems with that. And for now it's not worth the effort for them. So the entire point is, can we build this fast enough that first of all, we get it right. And we do it good. Yeah. But by the time they turn around and they're like, Oh, now we're ready to make an acquisition within this geography, or we're ready to build within this geography, we've already kind of done most of the work.
So then we're a natural acquisition partner. So then it's like, okay, then we'll just, it's better to buy them to compete and to start from scratch against this
business. So that was the premise. The incumbent company ended up going through a lot of struggle and that then affected us, which was ironic because. It was like, we are building this for this other geography, but then now that they are struggling, it's harder for us to raise the next round because it's very obvious that it's actually not working even for them. So it's like, Oh, you want to try the harder version of this thing. And this thing doesn't seem to be doing well. So, so yeah, so I know it goes both ways, but yeah, that's one thing I'm interested in. And then on the other side. You mentioned like being internal within a business. I think even the example you gave shows that you can actually quite easily end up being on a bum project where you get stuck on this thing and you do things that don't ship, or I think sometimes because of the ways certain company, that their culture is, you know, Google is probably a good example where you can do like a dozen moonshot things and none of them will go nowhere. But then the other side of it is. I've heard someone mention recently about the difference between, you know, hiring engineers from one big. Tech company versus another big tech company. So let's just say hypothetically, one is Amazon, one is Google. And apparently I don't even think that Google, well, you know, say it's Google that they use some of their own infrastructure internally, like their cloud infrastructure. Where, so if you were to hire someone from, Amazon or this other company, they are actually better because they use their thing. If, if you are hiring this person to come and build this thing for you, they don't even use it. So they will be terrible to hire to come and help you do this thing. And the analog of that in the context that you mentioned is just that sometimes Because of the culture in a particular place, you might not even be getting skills that would then be useful for you to then leave and go do something else.
Somewhere else, you might just be okay. You you've optimized for getting 400 K total comp, and that is great. But then how do you get out of that? How do you either move up or kind of find a way to make those skills useful somewhere else?
Jason Shen: Okay, I'll start with that 1 1st and then work backwards. I think it is true that each company has different cultures. I think there's like, at least some convergence within like, big tech that that, you know, yes, you need to adapt. But yeah, I mean, you do need to adapt like, that is a reality. There was a guy who spent 25 years at Apple and came to Meta as an engineering, like a senior staff engineer, but he did not understand the need to win people over, to rally people, to convince people to work on his thing.
He had a big, complex, technical project that he wanted to do. Work on, but it was sort of like, what is the business case for this? It's just not enough to do it because it's elegant and better and you're just like experienced. So therefore like people have to listen to you. And he really struggled with like understanding the culture of metas, like more flat, more persuade me.
I don't have to work on this, you know, like, as an engineer, even if you're two levels, three levels above me, kind of, so, so that was tough for him. It's. It's like you won't work on a good project at first for most of the time, like the whole argument is like actually at most projects are filled internally.
So it's only when they can't fill it internally. They go external. So you're almost by definition getting kind of a shit project that no one else wanted to do internally and they have more data than you about what it is. So you have to like, get through that one, earn your way to the next one. Like, I spent 2 years inside of a sort of like more.
Yeah. Yeah. Dusty team inside the company and then like made this leap into Facebook groups, which is so like mid tier, you know, wasn't like the super sexy stuff, but it was like, okay, we're in the blue app. We're in like, you know, and there was a upgrade in, like, the rigor and the sort of complexity of the job.
So even internally same level. You know, theoretically more experience. I'd gotten good ratings. I got like, good ratings throughout my time. And then at the very end, I had like a bad rating because like, I joined this new team and all of a sudden I was like, starting over. So you inside the company can, it can shift but, but I do think in the end, like, there's, there's.
Adaptability is important no matter what you're doing. And I think there's enough overlap that it's more similar than like being a founder versus, you know, going from one big company to another. In terms of the, the sort of focus on specific narrow domains, one of the other related things I think that's relevant is this I have this understanding now that it's like you can't do every kind of business.
It's not like every business idea. There's like, you know, this phrase founder market fit, right? You have product market fit, but you also have founder market fit. I have a founder who. Like comes from a family of finance sort of people, like, you know, sisters, a venture capitalist dad, you know, worked, worked in accounting.
Mom was like a trader, you know, early in NVIDIA. So he's doing like a crypto trading app. It, this is like perfect for him. Right. And he uses his own product a lot. You know, somebody else who's just like, Oh, crypto is hot. And this is cool. And I could build this. Is not going to be like him or his families and his videos and stuff, you know, because they, they like for it, you know, and.
Not everyone can do every business. I have a, I have a client now who's exploring some new business ideas and you know, there's some things that I'm like, I don't know, like I'm, I'm leaving it open, right? Like you, you explore this, but it's like, I don't feel like you're going to be able to come in here and have credibility with this type of customer and like, you know, sign a deal because of your background and just like what, you know, your age, I mean, he's pretty young, like there's just certain things where like, that's not gonna, So, understanding that, you know, you as inherently as a person is going to have certain advantages for me as a coach, right?
Like, people come to me who have a lot of different things that they, they their own background, you know, David, like you and I, we feel that connection. There are also people who are like, I want to do something different and you've done a lot of different things. So like, you know, you can help me like navigate this bridge.
Asian people. I work with a lot of Asian clients. That's just a reality. Some of my best clients have been Asian American men. That, that makes sense, right? Like, and it's just not going to be the same for, you know, a white woman or, you know, what have you doesn't mean that a white woman can't coach an Asian man or vice versa, but just that it's a different kind of experience.
And that's inherent to like. All of this, right? Like my product, even that what I say, how I organize my meetings, all those things, that's like part of it. But half of it is just who I am, which I can't like directly change. And so I think understanding that, you know, there are certain advantages that you have in certain ways of your Experience being relevant to what you do now is important.
David Elikwu-1: Sure. Yeah, that makes a lot of sense. So you're a coach now, you've kind of gone on this journey from athlete, builder product manager or manager in general, and now being a coach, but you've also written some books along the way, which we haven't talked about as much, but the most recent one being about misfits, and I think maybe we can connect those two together.
So. First of all, tell me more about the, the book, this idea of misfits, why that is important, why that is something that you care about or focus on and what the unique challenges are that they face.
Jason Shen: Yeah. So, I mean, I have a copy here. I like to just like, you know, have it on hand. Like I love this, this face, this this guy, this deer weirdly brilliant.
David Elikwu-1: I said, I love it. I love the cover.
Jason Shen: Yeah, cause this could be anybody that, you know, and I think the idea that being a talented misfit, right? Like when you have. I talk in the book about the story of Rudolph, which I first learned of from VisaCon in a talk at Thesis. And he talks about this idea that like, there's a meme that says, deviation from the norm will be ridiculed until it is exploitable.
And so it's sort of like, if you're weird, you know, we're going to reject you unless you have something valuable to add to our group. In which case exploit is maybe a strong word. It seems like Rudolph is somewhat happy and he's not being unduly pressured into being, you know, it's like, we have your family hostage.
If you don't do this, it's over. But, but It's sort of there's a negative side of that and a positive side, which is to say, like, your job is to add value to the community that you're a part of or find a community where you can add value. And in many ways, your differences is what can help you add the value that is missing from that community because they don't have it.
That's why you're different. But it's not automatic that your difference is going to just disappear. Create value on its own. You have to figure that out and you have to prove to people and show to people that you can create value, that they can trust you, that your goals are aligned with theirs. And, you know, sure.
In a world where we would love a world where everyone's embraced and accepted and loved for who they are just right off the bat, and that is a world that we should be striving to achieve. But this is a book about advice for the misfit. You know, given that you can't control how other people are going to slowly become more inclusive or what have you, your job is to make that process easier.
It can feel a little bit like maybe blaming or shaming the victim, but it really is to say like, you know, product onboarding, right? Like if people don't understand how to use the product, they're not gonna use the product. People understand what your story is. I have, you know, one of the there's these five strategies.
The second last one is own your story. It's really to help people make sense of this. Person that doesn't quite make sense to me, right? I have this like little recap story that I say when people ask me like, why did you decide to become a coach? That's a very natural question. You can answer that in so many different ways, but I have a sort of like tight, you know, 45 second thing that I say to that, that helps people see a bunch of different parts of my background and understand like why this is not just some.
Thing that I've like on a whim decided to do or I don't have any other choices and so I decided to do that because that would change how they experience or like consider what i'm doing so those are some of the Like initial thoughts of this book. It was done in a 30 day Brands that we were both a part of.
That's how we met right through Kelly Wilde Miller. So, you know, I'm really grateful that we were both part of that. You're working on a book of your own. I think that is going to come out very soon. And. You know, I had a blast putting it together on Canva, you know, it's a very visual book and very different from the first book that I did that was called Path to Pivot, very research backed, very like evidence driven.
And they're each kind of representative of a part of me, like a very rigorous, framework driven, you know, analytical side of me, and a sort of like wild, creative, like sort of, not playing by the rules kind of, side of me.
David Elikwu-1: Sure. Maybe one of the last questions I'd ask is, and I think this is still, you can decide the extent to which this relates to your, your book, but it's also relating to your, your coaching. First of all, I'd love to hear the 45 seconds on why you became a coach. But second, I am interested to know what is the most common. You know, one great thing about coaching, you know, to the extent that I do it as well, you know, I, I do work with, work with founders. And I think one of the big benefits is you get to pattern match. So you get to see people working on individual problems that each feel like they're in their own silos. But because I get to speak to five of you, I can actually see, Oh, these are the commonalities.
Here are the things that. You know, you all share that are actually very similar. And so actually my competence compounds, because I get to see this same problem and how it surfaces in this different domain. And in this different context, it might look different originally, but then I realized actually, this is the same thing. So are there maybe a small number, like two to four highly generalizable things seem different in each person's individual context, but that you've seen from your context as a coach, where you get to speak with lots of different people that you're like, Oh, here are some things that lots of different people seem to struggle with or seem to face. That might seem like, Oh, you're on your own and this is a highly specific thing, but actually I can see that lots of people face this thing.
Jason Shen: Yeah. So I have a sort of triangle that I've, that I've identified recently. So I'll talk about that. I'll do my the 45 minute sort of pitch because I think that that's, that's, you know, you're curious. And I think now that I've, I've sort of said it out loud, I can't, I can't like not say it. Right.
But you know, I think that for me, when, when you sort of, if someone asked me like, why'd you become a coach? I would say, look, I was, You know, that weird hyperactive kid from China who was like mostly in books and really didn't had a little bit of trouble, you know, fitting in with my classmates.
Had ADHD gymnastics was sort of my first home where I found a place that I could belong and I could train and I could become quite good and sort of learned the value of, of hard work and, and, and coaching. And I got a scholarship to Sanford and, and, That opened my eyes, right? Silicon Valley was like a brand new place for me.
It was all this stuff about how you could actually change the world. That was the energy that we had at the time. And so, I kind of jumped in and spent 15 years starting companies, working in marketing, working in product. You know, building voice assistance, you know, building a ride sharing platforms, building a B2B tech hiring tools and working at places like Etsy and Facebook, you know, and I had a ton of hard lessons.
I, you know, made some money, lost money, failed a bunch, but eventually when my companies was acquired I kind of made it, you know, but working at Facebook, you know, You know, for a couple of years, it was good money. It was a good time, lots of learning, but I knew I needed to change. Right. And I kind of wanted to start something new, but I didn't know if I wanted to do another venture backed business, at least not right now or any, in the immediate future.
And so I think about my roots, gymnastics, education, you know, my dad was in education and I started like coaching some founders on the side. Cause I've received coaching myself during some of those years and. Or for different people to help me see myself and see what I was doing in a, in a better way. I had a really good time with that.
And I kind of look back on my career and what I'm really proud of is like all the careers that I've helped launch, you know, the people who joined us early on, the people who worked for us, who who've gone on to start their own companies or become senior leaders in the industry. You know, that's what I'm most proud of.
Not the, millions of people were using Facebook groups that I got to work on. So that's how I started to coach and, and I went full time in it about a year and a half ago. Get to travel the world with my wife, who is a contemporary artist. And it's a, it's an amazing job. It's really what it feels like I was meant to do.
And so I, I love it a lot and I continue to learn. Every day. I don't know if that was that was probably a little bit longer than 45 seconds, but you know, you see the sort of arc there. And I kind of hit a couple of the points of like, okay, gymnastics, Sanford, you know, name drop some, but kind of really focus on like, the, the learnings.
And then, like, the shift in a decision to do something different, a full circle moment of, like, going back to the roots. So this is not something that, like, newly emerged. It's actually something where the seeds are planted early on and introducing, you know, my wife is some personal sort of background.
Round out myself along with my professional experience. So yeah, that's, that's kind of that, that intro. And then in terms of the, the, the common themes, I would say the common themes include I think there's a triangle, you know, for a certain type of founder, like a year. To two years after Y. C. I could with pretty good reliability, go to one of those founders and say, look, you're either killing it, in which case, good for you.
You know, you can still hire me as a coach and we could support you through that. But if you're not killing it, which is probably at least more than half of you. There's probably a trifecta of things that are happening. One, you are questioning whether or not this product is, is the right product or you're pursuing the right market, or maybe you've already tried to pivot and you're kind of in the middle of that or, you know, struggling through the pivot process.
Two you may have conflict with your co founders, maybe because of the fact that this isn't working. Now you're questioning each other. You're like, stepping on each other's toes. You disagree about where you want to go forward. There's, there's probably some conflict in your team that you're also working with.
And then the third, Part of this is personal internal. It's like you're questioning yourself. You have self doubt. You're wondering if you can actually do this. If you really belong here, if you know why she made a mistake, if you're an imposter and that's also affecting, you know, you maybe feel burned out.
You're just tired of like everything not working. So that trifecta is is very common for a lot of founders that I work with at a certain stage in their business where Bye. It's just not quite clicking. And this you bounce around between these three points and you can kind of like You have to like find your way out of that, like, gravity.
Well, if you will, to, to kind of, restart your growth and, you know, that's, that's one of the things that I work on and we can talk more about that, but that's sort of like a theme.
David Elikwu-1: Sure. I mean, if you don't mind, I'd love to hear a bit more about that.
Jason Shen: Yeah. So part of it is, is setting expectations, right? So, okay. On the, on the first front. You know, the first advice from the product side, it is like, okay, try to understand your customer better. Try to understand what you're capable of building and like, how can you do that 10 X better thing for a very specific segment of the market or specific use case where you can really dominate and sort of like build from there. Right? And the more focus you can get, the higher chance you have of being able to sort of be so much better than the alternative. That's sort of one dimension, right? There's a lot of parts to that, but that's at least one. The second one is with you and your co founder, right. You know, a lot of it is about respect and admiration, right.
And adapting to what they need and them adapting to you. Like I think in LA, you know, I've played couples counselor and sort of founder therapy in, in that sense. And some of my clients. And it's a lot about understanding, like each of you come from different perspectives. And sometimes you think you're very similar because you, you know, went to the same school, you both are, you know, working in a similar kind of industry, but you grew up in wildly different environments where money was considered differently.
What it means to work hard was considered differently. What is good look like is considered differently. And you're judging each other on your own perspective and not. Sort of taking into account theirs, right? And there is no standard right way to do things. It is a negotiation. It is a contract between the two of you to understand that, like, one person's idea of hard work is you never finish your to do list because there's so much on it.
Another person's is like, I want to have a ambitious list and check it all off and then I want to stop. But I need that list to be able to check it all off or else I won't be motivated to finish everything. Because why, why work so hard if you're never going to finish it anyway? So those are two opposing viewpoints that need to be reconciled to some degree.
And, and it, it requires a sort of willingness to, to kind of understand, listen and try to. And then the 3rd point of like, you know, being or now being disappointed. It is it is a lot about setting expectations, recognizing that, like, actually, this is normal. This is not some some wild fluke and you're like the 1 person who's struggling.
This is this is common. You know, the key thing is making good decisions going forward. You know, you're never really back at square one. Even if you, you know, build a, you know, product and user base and then you decide to pivot and you're starting from square one, you're never really at square one.
I believe that, like, maybe you're occupying the same like X axis, but the Y axis is now different. You have new perspective, you have a new established name in the market. And you just have a new view on things. And so, you're never really at square one, even if you feel like you've backslid. And, and I think that helps people not get so down on themselves.
David Elikwu-1: Sweet, that makes sense. I think that, first of all, lots of people need to read your book, both of them, The Path to Pivot, as well as your most recent book. I think they are both incredibly useful. And then also, I think, first of all, you know, I think you're great. We've had conversations, but then also, you know, From your background, obviously you have a lot of very relevant experience that a lot of people will find useful, but I think more Specifically the idea that more people probably should have coaches and I think this is something that is criminally overlooked And I think that it is a downside of the idea that That is becoming more and more popularized that actually, you know, everyone should be their own Island and you should just go and build things.
And why don't you know what to do or what to change? And I think even as you talked about, for example, with people going into YC, I do think that there is maybe a secret, a secret shame that some people might feel that, Oh, I go into this thing or I say, I'm starting this startup, but I actually, do I really know what I'm doing? And. You know, I see the people in my cohort that do extremely well, but my thing is not really working in the same way. And I think these days you're also getting some people that are even pushing back on the idea of going to YC in the first place. Because some, for a lot of people, there's this idea that, you know, If I don't even get into YC, I think you mentioned someone that got rejected from YC four times, you know, maybe I'm not cut out to be a founder.
Maybe I can't do this. Maybe either my idea sucks or I suck or, you know, there's something wrong and something that can't happen here.
I mean, I don't know if there's anything in particular that you say to people that are in one of those boxes, but I think it's, it's a lot more people these days.
Jason Shen: Yeah. I mean, it's so competitive. It has become a sort of its own sort of weird, like graduate school. I mean, it is an institution. Which they always talked about wanting to be an institution, they've arrived. They are an institution, you know, they have their own campus right on on the, on the in San Francisco Mission Bay.
And, You know, if it, it's, it's certainly, certainly not the case that every great company that's come out in the last 10 years went through YC, you know, some of them did, but, but plenty of them probably, you know, definitely more than the majority of them were not. And. The, the reality is if you're the kind of person who would give up because YC didn't accept you, you weren't going to make it even if you got into YC, right?
And I think that's the attitude to have about it is that everything you're doing is, is about accumulating advantage and moving the business forward. And YC is one of those levers that you can go after. And sometimes you're in a position to take advantage of that. And sometimes, you know, it's just not going to work out for you.
If it helps after going to YC once, I went, I applied to YC for two of the other companies that I worked on and I got interviews, but I never got in. So it's not like even, you know, past alums have a free pass to do it again. So, you know, if you, if you keep that in mind, and there are definitely some who are recycling and going through, it's, it's really steep competition.
So there's, there's. There's often a difference between people who are good enough to make something and people who actually get it and I think that that's really important to acknowledge.
David Elikwu-1: Yeah, I think that's a really good point, but Jason, thank you so much for making the time. I mean, this has been awesome. It's been a really fun conversation hearing all these different
stages of your background. And I think people are going to learn a lot about what it takes to be an athlete, what it takes to be a founder, what it takes to be a great PM, the things that you will learn from a great coach.
And hopefully people will be able to apply a lot of those things to their lives as well.
Jason Shen: Thanks so much for having me on david. Really appreciate it.
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