David speaks with Jason Shen, a three-time founder, writer, executive coach, and NCAA gymnastics champion. Jason Co-founded 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:

🚀 The realities of startup founding and pivoting

🤝 Navigating co-founder relationships

🌱 How early experiences shape entrepreneurial paths

💡 The power of focus in building successful businesses

🧭 Coaching founders through critical challenges

🚧 Choosing your path as a founder


This is just one part of a longer conversation, and it's the second part. You can listen to the earlier episode here:

Part 1: 🎙️Passion, Competition, and Drive with Jason Shen (Episode 130)

🎙 Listen in your favourite podcast player

The Knowledge with David Elikwu - Podcast App Links - Plink
Podcast App smart link to listen, download, and subscribe to The Knowledge with David Elikwu. Click to listen! The Knowledge with David Elikwu by David Elikwu has 29 episodes listed in the Self-Improvement category. Podcast links by Plink.

🎧 Listen on Spotify:

📹 Watch on Youtube:

👤 Connect with Jason:

Twitter: https://x.com/JasonShen

Website: https://www.jasonshen.com/

The Path to Pivot: https://amzn.to/4iFFRfh

📄 Show notes:

[04:13] The Journey Begins: From Immigrant Roots to Stanford
[05:53] First Steps in Entrepreneurship: The Stanford Spirit Book
[06:32] Early Ventures: Nonprofits and Competitions
[08:01] The Y Combinator Experience: A Golden Ticket
[13:43] Startup Challenges: Lessons from Ride Sharing
[21:52] Bootstrapping vs. Venture Capital: Historical Perspectives
[25:22] Building vs. Working: Insights from Both Worlds
[29:48] Navigating the Ecosystem as a PM
[30:04] The Importance of Being on the Right Projects
[30:08] The Reality of Internal Team Success Rates
[31:40] The Political Nature of PM Roles
[32:22] Building in Competitive Spaces
[34:11] Challenges of Internal Company Culture
[37:50] The Concept of Founder-Market Fit
[40:06] Coaching and Personal Growth
[48:20] Common Struggles of Founders
[52:54] The Value of Coaching and Mentorship

🗣 Mentioned in the show:

Stanford University | https://www.stanford.edu/about/

Y Combinator | https://www.ycombinator.com/about

Etsy | https://www.etsy.com/

Burning Man | https://burningman.org/about/about-us/

Boston University | https://www.bu.edu/admissions-overview/

Kelly Wilde Miller | https://kellywildemiller.com/

Ray Kurzweil | https://www.britannica.com/biography/Raymond-Kurzweil

Paul Graham | https://en.wikipedia.org/wiki/Paul_Graham_(programmer)

Jessica Livingston | https://en.wikipedia.org/wiki/Jessica_Livingston

Sam Altman | https://en.wikipedia.org/wiki/Sam_Altman

Christopher Columbus | https://www.britannica.com/biography/Christopher-Columbus

Nassim Taleb | https://en.wikipedia.org/wiki/Nassim_Nicholas_Taleb

Richard Dawkins | https://en.wikipedia.org/wiki/Richard_Dawkins

NVIDIA | https://www.nvidia.com/en-us/

East India Trading Company | https://en.wikipedia.org/wiki/East_India_Company


👇🏾
Full episode transcript below

👨🏾‍💻 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

📽️ Youtube: https://www.youtube.com/davidelikwu

📸 Instagram: https://www.instagram.com/delikwu/

🕺 TikTok: https://www.tiktok.com/@delikwu

🎙️ Podcast: http://plnk.to/theknowledge

📖 EBook: https://delikwu.gumroad.com/l/manual

My Online Course

🖥️ Career Hyperdrive: https://maven.com/theknowledge/career-hyperdrive

Career Hyperdrive is a live, cohort-based course that helps people find their competitive advantage, gain clarity around their goals and build a future-proof set of mental frameworks so they can live an extraordinary life doing work they love.

The Knowledge

📩 Newsletter: https://newsletter.theknowledge.io/

The Knowledge is a weekly newsletter for people who want to get more out of life. It's full of insights from psychology, philosophy, productivity, and business, all designed to help you think deeper and work smarter.

My Favorite Tools

🎞️ Descript: https://bit.ly/descript-de

📨 Convertkit: https://bit.ly/convertkit-de

🔰 NordVPN: https://bit.ly/nordvpn-de

💹 Nutmeg: http://bit.ly/nutmegde

🎧 Audible: https://bit.ly/audiblede

📜Full transcript:

Jason Shen: [00:00:00] 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, 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 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 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.

This week I'm sharing the second part of my conversation with Jason Shen, who is a friend, someone that's had a really incredible [00:01:00] career, going from being a national championship winning gymnast at Stanford to being a serial startup founder, starting multiple companies, pivoting, exiting, eventually becoming a product manager at companies like Etsy and Meta.

He had, you know, really an incredible journey now being the CEO of Refactor Labs, where he works as a coach to outlier founders and senior leaders helping them to build conviction in their next chapters.

So if you haven't listened to the first part of our conversation, I'd highly recommend you go back and listen to it, but it's not necessary to get a ton of value out of this episode.

You're going to hear Jason and I talking about some of his early influences as a startup founder, how he got into that world, what made him seek this life of entrepreneurship, and some of the really incredible stories from his early days as a founder. We talk about what it was like applying to Y Combinator with his roommate, and what it was like to meet Paul Graham and Sam Altman and Jessica Livingston back in the day.

[00:02:00] And then we talk about, I think two things, first some of the common pitfalls that young founders can fall into and early stage founders in particular, but then also this idea that there is a unique difficulty when things might seem to be going well on the surface, you're starting to get PR, the business looks to the outside world as though it's doing well. But under the surface, there can be tension, there can be difficulties, there are things that often go unacknowledged and things that people don't always talk about on, on the surface.

So you're going to hear Jason giving the behind the scenes on a lot of what those early days are like as a founder, having been through that journey multiple times.

We then also talk about the history of Venture Capital, what makes it such an interesting industry, what makes good VC's and some of Jason's best advice for either young founders or young people that want to be product managers. Essentially, you know, people that want to build things either on their own or as part of a larger organization. As someone that's been through those hoops multiple times, Jason really shared a lot of interesting stuff [00:03:00] there.

And then finally, in line with his latest book, he's written two great books, Path to Pivot and Weirdly Brilliant. But the latter is really about what it takes to succeed as a misfit, as someone that might be highly competent, highly talented, but doesn't seem to fit cleanly into all the boxes that are presented in front of them, and you know, what does it take to navigate the world in that way, how can you make the most of your career, how can you make the most of the opportunities, how can you pick the right opportunities to pursue and this idea of founder market fit. We talk about that a lot.

So this was a really great episode. You can find jason online @jasonshen on twitter and also on other platforms you can go to his website. Jason shen. com. We'll have all the links to all of his stuff and all his books in the show notes in the description below.

You can get the full show notes, transcript and read my newsletter at thenowledge. io.

And if you love this episode, please do share it with a friend. And don't forget to leave a review wherever you listen to podcasts, whether it's on Spotify or Apple podcasts. Let me [00:04:00] know what you think. Let me know how you found this episode or what you've loved so far. It helps us a lot to make more episodes that you love, to have the guests that you love, and to reach other listeners just like you.

The Journey Begins: From Immigrant Roots to Stanford

David Elikwu-1: 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, [00:05:00] pretty much his whole career. So government, 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. 2004, 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, 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 on my own. The sort of two things that happened.

First Steps in Entrepreneurship: The Stanford Spirit Book

Jason Shen: 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. [00:06:00] 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. I got it 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, 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. 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.

Early Ventures: Nonprofits and Competitions

Jason Shen: 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 like a finance loan 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 had them.

So that was sort of like the initial group of people. And then, [00:07:00] 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 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 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, 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? And he was like even traveling at that point for six months. So I was renting out his room, [00:08:00] but we were like, why not? Let's see what happens.

The Y Combinator Experience: A Golden Ticket

Jason Shen: And we kind of brainstormed some stuff and applied and we got it. I kind of like stumbled into 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 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. something that you can be a part of, even if you're not an engineer.

David Elikwu-1: 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 [00:09:00] wasn't. 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. My first real job, I ended up like executing a series of layoffs and head count salary reductions for everybody, including my own salary. So it was sort of like, tough introduction to business, but in some ways like.

And then, 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 digital Ad sale platform. So, [00:10:00] 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 it made me think, well, he can, he can do this. Like, why can't I, right. 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. 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, broadly speaking there's certain things that [00:11:00] in restaurant, you'd be like, just stay for the, get the clef, you know, like you're already there. Just do it.

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. 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 past things and Facebook memories like, Apple's like album sort of like videos, all that stuff is sort of like in that it was in that mix. That was the concept. And 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. 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 printed photo albums that we would sell the people off [00:12:00] of the images that maybe were collected through this algorithm. And 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 Altman 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. If we don't get this, like, how many weeks 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 [00:13:00] get this phone call and Paul Graham's like, do you want to, you know, join? And 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. 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.

Startup Challenges: Lessons from Ride Sharing

Jason Shen: 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 [00:14:00] typical 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 the ride sharing. 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 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 [00:15:00] 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 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 [00:16:00] now I hear a lot of people say, Oh, we watched what's that film? The film about Mark Zuckerberg.

Jason Shen: Oh, social network, the

David Elikwu-1: Yeah, the social network. I watched that last year. Like, I did not see. Yeah, like, so I missed that one. All the inspiration. Yeah. I missed out on,

Jason Shen: Not to me necessarily, but like it, it like inculcated a whole generation. It was like the wolf of wall street of startups.

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, actually. It was a charity. I wanted to send used school books to Nigeria and I had started 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.

So I think because I had that start, [00:17:00] 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 yours, but 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 ride joy journey. I think I know, I heard you mention at some point, the idea that I think even in the gap [00:18:00] between, so there was the picture that you guys have with you know, all the YC group

Jason Shen: Yeah.

David Elikwu-1: And I think, yes, 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 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 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 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 had launched you know, a couple of years earlier, we were like, we're in that same boat. We're going to do the next [00:19:00] 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 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 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 there were some rides made from that, but it's like, it dilutes your focus or dilutes your energy and hurts your [00:20:00] 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, and you forgot to 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 be covering the whole country at once. 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 [00:21:00] 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 sort of, some of the youth and inexperience and naivety that I had.

And I think now as a coach, a lot of it is like 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.

You know, there was a lot and I wrote a whole article about why I don't think it worked out.

Bootstrapping vs. Venture Capital: Historical Perspectives

Jason Shen: But 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 [00:22:00] employee at, probably hired an executive assistant at some point, but 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 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, trading companies, right? The East India trading company. Various ships like Magellan, like they went to, you know, Christopher Columbus went to 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. 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. And you're going to get to name this place [00:23:00] to and other stuff.

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, you know, 1600's, 1700s. But it requires a high risk high reward, high failure rate thing. It's a venture. 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 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, 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 [00:24:00] time you're going to lose your shirt doing this.

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, Amazon and Netflix or what have you. And, you know, the individual entrepreneurs or explorers who fail and die or go bankrupt or whatever, that's just the cost of getting to those great things that we now have.

[00:25:00]

David Elikwu-1: I am interested to hear more about the lessons that you've learned.

Building vs. Working: Insights from Both Worlds

David Elikwu-1: 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, 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 [00:26:00] 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 [00:27:00] 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 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? [00:28:00] 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 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 that's one thing it's like narrowing in so that you can actually be a lot better than the existing [00:29:00] alternatives, leaning into places where people already spend money, you know. 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 building things.

For being a PM.

Jason Shen: 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 [00:30:00] known. Get sort of information early. Be on the right projects.

The Importance of Being on the Right Projects

Jason Shen: So much of being a PM is being on the right projects that actually take off.

The Reality of Internal Team Success Rates

Jason Shen: I would argue that the rate of success of internal teams inside larger companies is similar to venture, right. 10 percent of them do really well. 20 percent of them do okay. 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 grinded their way to the Ray Bans and like the headsets that still aren't killing it, right. That's in the 20 percent of being okay. And before that, what they had stories like reels, and then there's a million other projects that like

David Elikwu-1: And the TV, I still remember that, that's completely

Jason Shen: portal that, you know, gone, you know, like, shops on Instagram or whatever, gone. 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, [00:31:00] gone. But some people got promotions out of that. But like, for the most part, it's 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 runs. 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 yeah, it is a somewhat different skill set.

The Political Nature of PM Roles

Jason Shen: 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. PMs in particular have to be really skilled in speaking to a lot of audiences, helping a lot of people [00:32:00] building a deal, right? Like a coalitions, like a bill where, like, everybody has to have their thing that it kind of like, can get cleared and get all the check boxes and pass through.

It is a pretty different skill set. There's relevant thinking and 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: How do you navigate?

Building in Competitive Spaces

David Elikwu-1: So for example, when you were talking about building things as a founder. the idea of, I think 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 I went on a journey with a startup that I was a co founder of, which had been its own [00:33:00] incredibly interesting journey. But essentially 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. 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 [00:34:00] 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.

Challenges of Internal Company Culture

David Elikwu-1: 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 well, you know, say it's Google that they use some of their own infrastructure internally, like their cloud infrastructure. So if you [00:35:00] were to hire someone from Amazon or this other company, they are actually better because they use their thing. 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 one 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 yes, you need to adapt. 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 [00:36:00] 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 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. So that was tough for him. 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 [00:37:00] 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 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 shift, but I do think in the end like, 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 going from one big company to another.

The Concept of Founder-Market Fit

Jason Shen: In terms of focus on specific narrow domains, one of the other related things I think that's relevant is this, I have this understanding [00:38:00] 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 people like, you know, sisters, a venture capitalist dad, worked in accounting. Mom was like a trader early in NVIDIA. So he's doing like a crypto trading app. 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 like for it. 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, sign a deal because of your background and just like what, your age, I mean, he's pretty [00:39:00] young, like there's just certain things where like, that's not gonna work for you.

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, 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 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 there are certain [00:40:00] advantages that you have in certain ways of your experience being relevant to what you do now is important.

Coaching and Personal Growth

David Elikwu-1: 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: 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.

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 [00:41:00] 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.

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 create value on its own. You have to figure that out and you have to prove to [00:42:00] people and show to people that you can create value, that they can trust you, that your goals are aligned with theirs.

And, 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, 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, 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 [00:43:00] ways, but I have a sort of like tight 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 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 not playing by the rules side of [00:44:00] me.

David Elikwu-1: Maybe one of the last questions I'd ask is, you can decide the extent to which this relates to your book, but it's also relating to 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 one great thing about coaching, you know, to the extent that I do it as well, you know, I, I do 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 that seem different in each [00:45:00] 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: So I have a sort of triangle that I've, that I've identified recently. So I'll talk about that. I'll do the 45 minute sort of pitch because I think that that's you're curious. And I think now that I've sort of said it out loud, I can't like not say it, right.

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 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 hard work and coaching. And I got a scholarship to Stanford and that opened my eyes, right? Silicon Valley was like a [00:46:00] 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 B2B tech hiring tools and working at places like Etsy and Facebook, and I had a ton of hard lessons.

I 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 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 [00:47:00] 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, 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 [00:48:00] 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 to help round out myself along with my professional experience.

Common Struggles of Founders

Jason Shen: And then in terms of the common themes, I would say the common themes include I think there's a triangle for a certain type of founder, like a year to two years after Y. C. 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 [00:49:00] 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 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 very common for a lot of founders that I work with at a certain stage in their business where 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 restart your growth. And 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 [00:50:00] 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, 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 10x 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 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 [00:51:00] 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 it, it requires a sort of willingness to understand, listen and try to adapt.

And then the 3rd point of like, or now being disappointed. It is a lot about setting expectations, [00:52:00] 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 common. The key thing is making good decisions going forward. You know, you're never really back at square one even if you build a 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 I think that helps people not get so down on themselves.

David Elikwu-1: 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.

The Value of Coaching and Mentorship

David Elikwu-1: We've had conversations, but then also, you know, from your background, obviously you have a lot of [00:53:00] 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 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 [00:54:00] 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 in San Francisco Mission Bay.

And, 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 plenty of them, definitely more than the majority of them were not. 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 [00:55:00] 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 past alums have a free pass to do it again. So, if you keep that in mind, and there are definitely some who are recycling and going through, it's really steep competition.

So 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: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next [00:56:00] time

Share this post