Founder Of $14B Startup Calls Stripe and YC The 'Mob Bosses' Of Silicon Valley

My motivation here was to open people's eyes to what goes down in Silicon Valley, where it's not all sunshine and rainbows. It is very fierce, and there's fierce competition, and there's also games that are played with powerful institutions and, you know, groups of people who, you know, help each other out.

Don't chickens have two wings?

But it's not their actual wing. Hey, what's up, Ryan?

What's up, Sean? Sam?

What is it?

Dude, you can settle this for us. So, Sam, this is Ryan. He's the founder of Bolt. And we're having a— we're just going over this detail. Are chicken wings actually the chicken's wings, or are they just like the ribs of the chicken?

I think they're the wings.

What's a drumstick?

You think they're the actual wings? I feel like they're not the wings.

Yeah, this is like, this is like a such a stupid conversation. Of course they are. Like, what's a drumstick? Isn't drumstick a leg?

Powerful young Ben. Ben, look that up. See, you see if I'm right. I think, I think I'm right. Um, all right, so we should, we should switch gears. Uh, okay, so Ryan's here. I met Ryan in, uh, where are we hanging out? LA. Okay. I was in LA. I'm at this dinner and, um, and Ryan's across the table from me. And at this dinner, everybody kind of like dressed up because it was at, uh, the dinner was at the owner of an NBA team's house. And, um, you know, so most people are pretty dressed up. I see this one guy who looks like, I'm like, is this a TikTok star? Like, who's this guy? He's got earrings. He's got this like tie-dye shirt on. He looked totally different than every other kind of like business schmuck at this thing. And I was like, oh, what's up, man? Like, what's your— I was like, like, I'm literally in my head, I was like, this guy's definitely a TikToker or a YouTuber. He's got this like charisma about him. I feel like that's who he is. And he's like, no, I'm Ryan. I, you know, I started a payments company. I was like, oh, what is it? Bolt. And I was like, oh shit, I know Bolt. That's amazing. And we ended up becoming friends, ended up investing in the company, and you ended up getting Twitter famous over the last few months, my friend. And I wanted to have you on to talk about a couple things that you've done some pretty impressive stuff at a young age. I want to talk about— I want to give people the background of that. And then you currently have some spicy Twitter shit going on. I want to get your take on some of those things. Welcome to the show. I don't know if you've ever listened, but we have a very casual business show.

Yeah, it's a pleasure to be on, Sean. I've been looking forward to doing this, and I think we picked the perfect time.

And Sam, what do you know about Ryan besides what I just told you?

So I was Googling you. So I saw your Twitter come out of out of nowhere about a month and a half ago. And Sean told me all about Bolt and he told me about this dinner that he had. And so Bolt is a payments company, uh, that is at like $11 or $14 billion in market or valuation. So it's a huge company. What I know is that you look incredibly young and on your bio, maybe on LinkedIn or something, or maybe Twitter, it says that you've started 2 or 3 companies that are worth about a billion dollars, including a bunch of crypto stuff. And when I was Googling you today, One of the first images that comes up, it's beautiful because you're tweeting about mobs and mafias. You're— the Forbes headline is Meet the Stanford Bitcoin Mafia. And it was a picture of you with like 3 friends. And so I know that you've got your hands in a bunch of stuff.

So Ryan, what's the, what's your claim to fame? So this is the part you don't have to be humble. Just give people the, the reason why they should be listening. Who is this cat? Uh, what have, what have you done? What's your claim to fame?

Well, my claim to fame is I think I've, you know, I operate pretty fearlessly and I've, you know, done a lot of things that I think I've been told I shouldn't be doing. So I think it's business. I've been told by many people I shouldn't be doing, that would never be possible. And, you know, we've written the framework on culture Uh, on conscious.org, people are like, who are you to write about culture? Now we have close to 100 companies pledging that culture. We've written books, done 4-Day Work Weeks. So, you know, I think we're thinking differently, myself and the whole Bolt team. And, um, very proud of that.

And so walk us through, um, the, I, I don't wanna go too far into what Bolt is. I'll give kind of like the TL;DR on, on, on the, I'll, I'll oversimplify it. You might cringe a little bit as I oversimplify, but basically Um, the way we pay for things online is, uh, you know, some people shop at Amazon and Amazon says, hey, one click checkout, we got your stuff saved. And then you have Shopify and Shopify has a bunch of stores. Now Shopify has Shopify Pay, which says, hey, you've shopped at a Shopify store before. You can check out that way if you want. Apple's got Apple Pay. They let you pay at some places. And what you've done is you went to like, you're like, hey, you know, even though those, those companies are huge, they're monstrous. The internet's a lot bigger than that. There's a whole bunch of stores that aren't on Shopify. There's a whole bunch of platforms like, uh, Pinterest, uh, where people go and they find products they love and they love to be able to check out. And as somebody who owns an e-commerce store, you— I felt this pain many, many times, which is you can look at how many people just drop off at the checkout because they don't want to type in their name, their first name, last name, address, credit card, you know, zip code, blah, blah, blah, every single time when they're on their phone and they're on the go. And I just see how like that's the biggest drop-off in our whole store. It's like, shit, what could I do about that? Like, wouldn't it be amazing if there really was a way to just check out at any store, have your information saved? It would make a merchant like me more money because my drop-off would be lower. It would make the consumer experience easier because I don't have to type in the same shit over and over and over again. And it has this like network effect where the more stores who use something like Bolt, The more shoppers have a Bolt account, now every single store benefits because that account can be used on all these different stores. Amazon is gonna work on Amazon and Shopify's gonna work on Shopify, but the world is a lot bigger than that. All right. How did I do outta 10? Did I, did I, did I get it or what?

I missed Sean. That was like pretty epic. Uh, we need to put you in customer calls.

Yeah, there we go. I'm, I'm down. So, um, so that, so you create Bolt and you're saying at the beginning people told you don't do this or it can't be done. What, what's an actual story that happened there where somebody kind of told you, look, look, man, it's not gonna work. Okay.

So I have a pretty extreme story. I went to one of the, you know, tier 1, uh, Silicon Valley firms, someone who is a PayPal led, you know, not PayPal, sorry, of payments legend. Um, not PayPal mafia, but a payments legend, big firm, big name. And, uh, I went in, I told them about what we're doing. And they spent the entire conversation telling me why this couldn't be done. And that, you know, they actually got mad during the conversation. And then after the conversation, they saw one of the people on our team, 'cause we were recruiting top people, was at another company they were involved with, spent 3 hours trying to convince that person not to join us. And to join other portfolio companies. And so it's amazing, you know, I think everybody coming from the payments space, the OGs, they have real, you know, they've been in the sausage factory, they see how hard it is. But I think there was a little resistance to the fact that there could be something this disruptive that's this obvious. And we just, you know, decided to go ahead and do it.

What were you— and I want to hear all about that, but what were you doing before this, before Bolt?

Sean had mentioned I dropped out of school. So a little bit about my background. First job was bagging groceries, did that for 3 years, and then I started going to the internet to make money, started some websites, online businesses, ran a web development agency working for a lot of other customers. So that's where I learned everything there is about e-commerce. And then I was lucky to get into Stanford, started the Stanford Bitcoin Group with some friends in early 2013, many of which have gone on to do amazing things. And I dropped out of school in 2014 to focus entirely on crypto. I'm like, crypto is going to change everything about payments, which I still believe. But about a year in, so mid-2015, I was like, wait a second, why has nobody solved this checkout problem? If you create a checkout and all the users who go through your checkout enroll in Shopper accounts, you could create the most powerful, important Shopper network, payment network on the planet. And so like, this is a sight I couldn't unsee, and I decided to go you know, realize, like, learn about the space. The more I learned, the more I realized this was an opportunity. And so we started building. And, and yeah, so that's, that's, that's the story. Did you, did you, did you—

you dropped out before. I mean, you're probably what, 21, 22? You dropped out at a young age. Did you, did you just like knock it out the park with crypto to the point where like money You fix money's good, you're good, now you're gonna go and start things. Did it happen at that young of an age?

Unfortunately, it did not. I had this mentality that I was going to build things in crypto, not invest in it, which was a very costly mentality. I had like a little bit of crypto, I mean, you know, but you, you didn't become, you know, F-you rich. No, I'm not at all. Um, so I had to, uh Bolt had to make it. I was couch surfing, like I didn't have enough money to like even rent a place to stay. So I was couch—

a friend texted me before this podcast and he said, ask him like how wealth— like, uh, be like, well, he already got really wealthy from Bitcoin, is that why he's like so brash now? And so you've kind of just answered that question. You weren't—

weren't— and at Bolt, I start off at a $40K salary And for about 5 years, it never got higher than $60K. So I was living paycheck to paycheck. I wanted every dollar to maximize Bolt's outcome. And just recently, I sold a very tiny amount of shares just to kind of pay for some expenses. But up until about a month ago, I hadn't sold a single share almost 8 years into the journey.

What about your other businesses? You, you didn't sell any of those either. So you also helped start Eco, right?

Uh, or now known as Eco. Uh, your buddy runs it, I think, uh, who's also, what's his name? Andy Bromberg. Super like impressive as well. Yeah. And, uh, I don't wanna go too much into Eco cuz your Twitter stuff's frankly just more spicy right now, but basically you kind of helped the, what, just with the vision of that or the, the kind of the initial strategy of that?

Yeah. So I, what I can take credit for is I helped build an awesome team of founders and inspire some of the ideas, but they have really manifested Eco into what it's come, become today. Uh, the founders there have drove amazing vision, the ones who are on the ground every day and they've executed. And so I've played a part in the journey, but Andy Bromberg is one of the CEOs I have the most respect for. The planet. Henry Alt, Ryan Sachs, Joey Krug there have done, uh, miracle work.

Cool. And so let's talk about this Twitter thing. So you came out the other day and you, you basically said, look, um, you're like, Bolt, uh, you know, we, we've become successful now, but it wasn't, uh, without kind of some, some challenges. And there's like the normal business challenges, and then there's sort of the like the challenges of the powers that be. And in Silicon Valley, there's two kind of like very powerful— and in, in most people's minds, you, I think you picked a fight with people that very few people had bad things to say about— Y Combinator and Stripe, right? Stripe is probably like the most beloved startup in Silicon Valley, respected, beloved, whatever. And, uh, and YC is also, you know, the most powerful sort of like a brand in, you know, it's like basically if you're gonna pick on a college, you pick on either Stanford or Harvard if you were going for the top. And, uh, and you basically told the story about them being the mafia. And so I want you to kind of quickly, uh, can you quickly bullet point the, the, what your argument was for people who aren't nerding out on Twitter and aren't seeing it? Cuz this, the audience we have here is not gonna have seen it. So bullet point that and then I got some questions for you.

Yeah. So the point is my motivation here was to open people's eyes to what goes down in Silicon Valley. Where it's not all sunshine and rainbows. It is very fierce, and there's fierce competition, and there are also games that are played with powerful institutions and, you know, groups of people who, you know, help each other out. And so if you're starting a company, especially in payments, you've likely failed. There's You know, the only ones that have been successful have been internationally. Um, and we probably should have failed 5 times over with investors pulling out of term sheets when we were about to run out of money. And so we, I'd say Bolt almost didn't exist because of the powers that be, the powers that be. And, you know, I think there are a lot of other companies that would've existed today if it wasn't for the powers that be. And so, You know, now I don't blame these institutions, but, but what I—

you're, you're— I, I, I don't know if you're doing this on purpose to be kind, but you're kind of being vague. Is it possible that you could like— what does institution mean? And game— are you able to like actually— let's separate out, right?

There's, there's fair, fair, uh, you know, fair business games, which is like we're competing against somebody. That's fair. They can compete with us fiercely. There's, um, investors just deciding, uh, this space is too competitive or Stripe's gonna win, I've just gotta— I'm just gonna back away, right? So perception thing, that's kind of like nobody would say that that's unfair. Talk about the specifics of what you felt was unfair or where, you know, some, some, uh, some— there was some heavy-handedness to it.

Yeah, so when we would be pitching investors They'd get interested, they'd say they wanna invest, and then they would talk to somebody at Stripe, someone related to Stripe, and either be told they can't invest or they shouldn't invest, or somehow the conclusion was they were dissuaded from investing.

But, but how do you know that that's what happened?

Many of them, right?

They might just come to you and say, we're not interested.

Told me. Stripe would always come up somehow in that conversation. So many of them pull me directly. I have investors say directly, I got a call by Stripe and they told me I can't invest in you guys.

Is that bad though? I mean, what if they, if they were already an investor of Stripe? I, I understand that. I have a conflict of interest.

Right.

But you know, Stripe has like all the big names in Silicon Valley invested in them. Right. And so they've intentionally put every single, you know, tier 1 firm on their cap table and they've even stuffed them with small checks. They're like, everybody's on their cap table. Right. And so, you know, from—

and then they say you're conflicted out, right? That's a competitor of ours.

You're our shareholder. Don't— right, exactly. And I didn't even, you know, consider ourselves a direct competitor at the time, but I think they're very guarded about anything in their periphery. So I've heard the same story from companies, you know, doing card issuing. I've heard the same stories from companies doing subscription payments, and then Stripe would roll out their own product next. So it's almost as if they have these feelers out, anything that's tangential, they make sure that it doesn't get off the ground and then they go and build it.

And so is there any, is, but is there any side of you, so the way that you're phrasing it, and it, I would like to figure out what, what my opinion is. I don't have an opinion yet. Is, is like, that's unethical. But one maybe could argue and be like, well, that was just a savvy strategic move to like get everyone on board. And you know, that's just like, that's just like, that's a, that's fair. Is, do you, do you see that side of it at all? Or do you think that like the way they went about it, their intentions were— the intentions matter here.

Yeah, I've never told a single investor you can't invest in somebody. Right. And so to me, like, everything is fair competition. And if someone wants to invest in a company tangential to me, I tell them, go for it. We've even invested in tangential. I've invested in tangential. I think innovation is good. I have a very long-term perspective. So when you're calling, you can invest in this company, like, even if they're not on the Stripe cap table, investors too that are not on the Stripe cap table. To me, that's just not how I would do business. And I also want found— the next generation of founders to go into building with their eyes wide open, because I invested 8 years of my life into this business not knowing about the games that go on, right? And so the most important thing I'm exposing here is if you're coming to Silicon Valley, you have an idea, you're quitting your job, putting a lot on the line, Like, get ready for war. Like, it's, it's, it's serious. And there will be people who do not want you to exist and you're gonna need to be ready to battle that.

Ready to battle. And so one of the things you say is that, which is they basically hurt our ability to fundraise by telling, first they, they, they kind of played good, good game theory, right? They, they got every invest, every big investor to get a little piece of Stripe cuz every investor wants a piece of Stripe. And then they said, cool, now you're conflicted out of investing in our competitors. Okay. Some might say that's shady. I personally just— I'm an investor in you, right? I'm a fan of yours. I personally would just say, okay, there's nothing unethical about that. You may not like it, but that's competing. It's a strategy. It's a harsh strategy. Okay, fair enough. In the same way that I don't think it's cool that Mark Zuckerberg just copied stories or whatever. I don't think that's like— you don't get bonus points of respect from me, but I also don't think you did anything illegal or crooked, completely crooked, right? That's, you copied something that was copyable. Okay, fair enough. The second thing you said is that they, that YC, which has a huge stake in Stripe, control, they own Hacker News, and that on Hacker News, people would be posting about Bolt. It would get some play, it would go up the ranks. But that somehow there's some, you know, editorial shenanigans behind the scenes where all of a sudden the post about Bolt would disappear or get deranked and then a post about Stripe would be up higher. And so you posted some examples of that. Now that's— I think, I think that's the summary of what you said. As that was happening, did you— is that a suspicion or you're like, I know that that's what happened?

Pretty sure that's what happened. You know, because we had some posts, one in particular that I'd written catered to YC audience. It was an unraveling of how we do fraud detection better and guarantee it with your payments, which was radical and new at the time. It had organically gotten to number 1, held there. We had a ton of comments on it, just like very active people, very interested. You can go read all my comments. And then Stripe's post, I don't know if it was there before, It seems like they said it got posted technically before. But anyway, after it got to number 1, theirs started to rise and ours just started to fall and then disappeared. And so I don't know if it was editorial. There's also this downvote functionality. Right. And so you can also just have a bunch of your employees go and downvote or have a bunch of your friends So, you know, whatever it is, they were able to get us off of there pretty quickly.

Right. The, the guys who started Stripe, the Collison brothers, I don't know them, but they seem, um, from the outside, like good dudes. Do you think that is that? Do you know them? And is that an, is that a character characterization that you'd challenge?

Yeah. I mean, That's exactly what I'm doing. So, you know, they don't meet my standards for good dudes. And so, you know, good dudes is not what you say publicly, it's what you do privately.

And so, yeah, I just think that like right now you're like a loose cannon and I love it and I find it incredibly refreshing because from the outside you've raised money from amazing people. At a $14 billion valuation, you are like the guy right now. And I'm just— I think it's cool and I'm shocked, but I think it's cool that you're— that you've just said that. I think that that's— I've never heard that before.

Me and Sam both have definitely like a rebellious streak in us. And we've told some stories on the pod about situations where, where we do kind of like not keep it muzzled. And, you know, sometimes that works to our benefit. Sometimes there's some, you know, collateral damage or some, you know, some blowback from it. Uh, I gotta ask you, news came out, I don't know, yesterday, today, day before, you're stepping down as CEO of Bolt. Okay. Uh, did you get in trouble?

What happened here? So stepping up into executive chairman. I like it. I like it.

Uh, nice.

That's one of those things that you like come up in the shower and at bed at night you write it down.

Aha. You know, that was actually the truth. And I know it's— but yeah, the stepping up worked well on Twitter. And I promoted Manju because this guy is like, he schools me on execution every day of the week. So he started off running tech and product. They gave him COO, like 60% of the company reports into him. And just like my, it's not my superpower. My superpower is creativity, is vision, is culture, is landing epic deals for the company. So now I get to spend 100% of my time on that. So this is something I've—

Yeah, but the timing is weird, right? Everyone, a lot of people online, even though it's not true, they say Ryan got fired because of what he said.

Well, our, you know, this is, this is the start of our fiscal year. Ends basically January 31st, starts February 1st. And so this was the timing we had planned on for a while. And so then I had some people saying, you don't think we should wait? People are going to think it's related to the tweets or whatever. And I used to have fear about those types of things in the past. And I think this recent episode has just locked me into my fearlessness even more. I'm like, eff it. Let's just do it. And as everyone's going to gossip and, you know, interpret in their own way, and I actually think that's great.

Right. You're, you're crazy.

I like it. Yeah, I respect that. And also, um, I respect the move, not the CEO part. Right. Great. That's, that's fine. I don't know. I don't know anything about that, but, uh, for the, for the content that you're putting out. So, um, we've talked before about about how to pick a fight. In fact, there's a, there's a passage from a book called Rework called Pick a Fight. It's a marketing strategy and it's like a 2-page thing. And I remember earlier on the pod, I had literally read it word for word cuz I was like, this is a great idea. And I think this is when, um, the guys from 37signals were picking a fight with Apple, uh, and saying, you know, this is not right. Or Fortnite, you know, Epic Games from Fortnite was picking a fight with Apple. And, um, and we talked about, you know, there's a, there's an art to doing this. Like first, you know, you can't just completely make something up, right? You got to have actual reason to pick a fight. But then you want to pick a fight not when you're punching down. You want to punch up at, you know, the whoever is the sort of like the power. And when you do that, you're going to get this groundswell of A, attention, B, support, and C, other stories will come out of the woodwork that will make you seem even more credible. And, and you get your name out there. So like, you know, I don't know how many people knew about Bolt before this because it's like, okay, you know, Checkout technology is not the most like in-your-face, you know, it's not Snapchat, it's not like a pub, like, like a product everybody uses. Um, but a lot more people know about it now. And so how conscious were you? I mean, how strategic was it that you were, uh, you're thinking, you know what, like, I think if we come out with this story, yes, I'll be helping people understand how the game is played, but I think this will be good for Bolt too.

Yeah. I mean, I, I think doing what you believe to be right will always pan out in the end. And so I think this was— I stand by this decision. I think it's great for Bolt. It shows the world who we are as a company. It shows that we're going to stand up for what's right, no matter how controversial that may be. We're going to stand up to the big guys, which is literally what our entire product is about. And what I wrote to my team, you know, when I was doing this, I said, just because our company is worth billions of dollars, you know, I'm not going to become a sellout founder. Like, it's worth way more financially for me to go become buddies with all these guys, right? But every cell in my body, my spirit won't let me do that. And so for me, it was a way of telling the world who I am as a leader. And I'm trying to, you know, set an example of fearless leadership for the next generation of founders. Um, cuz I think we lack it. Like I can't point to too many leaders in this country who are truly fearless, who stand up for what they believe in. And I think a lot of leadership is fear-based. And I think we have to kill that.

I agree with you. I'm entirely on board with you. I think the— I don't, I don't actually think this is my stance, but I— in fact, it's not my stance, but at first it was, but it's changed a bit. And that's that. Like, I don't know if what you're saying is necessarily true. And I saw a lot of people who used to have your position where they're the underdogs, like Sam Altman and Gary Tan. They're not anymore. Now they're like the man, you know, the folks in charge. But in there, like, this guy Ryan is lying. He's false. He's just full of it. And so it's like really hard to take a side right now because of this he said, she said, even though I totally agree with you that they are this like cool kid group and it's always fun to stick it to that cool kid.

Honestly, the things you said that they did, this is like actually credit to you. The things that you said that they did are not even that bad. Like the he said, she said doesn't even really matter. Because it's like, if they did it, okay, even if they did it, it's not the worst thing in the world. If they didn't do it, nobody's going to know how to prove it. Kind of doesn't really matter. I think you pointed out the overall power dynamic and that's what was important. And then you just like got your story out there about who you are, your— what your point of view is, whether people agree with you or not, that's their choice. But I think it's actually— it actually emphasizes how brilliant the tactic was that it's not even like the most scandalous You know, Theranos, does this work? Is it a giant fraud? Is it deception at the highest levels? No, it's not. Even if the accusation is true, it's not. But it got so much play because of A, you're a good writer, and B, um, everybody is so afraid to say a word against them. Like, I got one of my, my most viral tweets was then I came out and said that Clubhouse is gonna fail, and, um, here, here's why. I think here's how I think it goes down. And, uh, it is because at the time Clubhouse was the darling. Every VC was fighting to get into the deal Everybody was on Clubhouse every night talking about how great Clubhouse is. That was the only topic they knew what to talk about. And that's why it faded quickly, because if you go on the product and all you could talk about is the product, it's going to fail. And so, and I got privately, I got a bunch of messages from high-profile people who are like, dude, I could never, I can't, sorry, I can't retweet this to like show support for this just because of, you know, politics. But dude, I totally agree with you. I like, or like, I'm glad somebody fucking said it. I don't believe in this shit at all. I had one person, you know, these are all blue checkmarks. Do people must be smoking crack if they think that this thing is going to work? And so did you get like the, the DM backchannel support of people who are like, look, I can't come out and I don't want to get YC on my bad side, but like, dude, you're so right. Hundreds, you know. Exactly.

If I, if I was, if I had any nervousness about doing it beforehand, the outpouring that I got afterwards just gave me all the conviction in the world that this was the right thing to do. Because hundreds of founders reached out to me thanking me, many of them sharing their stories with me about what encounters they've had. And, you know, this stuff is happening, this stuff is rampant. And so, yeah, I had all of those messages.

All you were missing, you needed a movement people could rally behind. You needed a hashtag. YC has done this to me also.

The problem is, why is everyone so afraid?

Right. Well, why are you asking that question? You know the answer, right? You already said the answer, which is you'd be significantly more financially successful if you just were to shut up. And so that's why I asked you that question. Are you already very financially successful on paper? Just on Bolt, you're very— you're set. Uh, that's on paper, but that's why I was asking, do you have this like crazy Bitcoin stash? Do you, did you have this other stuff?

I think even in this tiny version of the interview, you've actually heard 4 or 5 examples, like dropped out of Stanford. That takes some guts to do that when you don't have something else that's working amazing.

Yeah, but that's what I was asking. I want to know.

Dropped out to focus on Bitcoin when Bitcoin was nothing at that time. That's fearlessness. Start payments company to compete with in one of the most vicious fields where everybody tells you, everybody who's smart that you respect tells you that this ain't going to work. Fearless number 2, going on the 4-day, basically saying we're going to only do 4-day work weeks because I believe in XYZ in terms of company culture, coming out against YC, right? So that's actually like several, uh, of these kind of like, you know, it's like when I invest in something, I've looked for like a breadcrumb trail. It's like, oh, actually I see a trail of this person doing, you know, really bold things or, uh, you know, clever things or hacking different systems. I think they're gonna— the next thing is just gonna be more of that. And so, you know, that's, I think that's pretty cool. I wanted to, to switch gears a little bit and ask you, um, you, uh, you are an idea guy. In fact, and when we were, uh, driving home from the dinner, you were telling me some different, like, I was like, how'd you get the idea for Bolt? How'd you get the idea for Eco? And I just kind of got the, got the sense that you're an idea guy, but you're fully, you know, you've been fully locked in for 8 years doing one idea. So, I want you to get out that little note sheet of other opportunities, other things that you see that you don't have the time to do or the energy to do or the interest in doing, but you think that these are opportunities that exist. Did you bring any ideas for me? I brought some. Okay, fire them off and we will react to them. So you give us the quick pitch and we'll react.

Okay, this is a big one. I think a lot of people are gonna do it if they hear this, so I hope they do. I think someone needs to start an investment bank for early stage companies where they help introduce you to a bunch of investors. You know, they sanity check your deck and materials. They blast off a bunch of intros, which is 99.9% of the value that YC has, right? And they don't even do that. They don't even send personal intros. You're one of 400 companies, right? So now you're, you know, the company that's being introed. You're a serial number, literally. And so, um, somebody needs to do— so that's what I do personally. I've probably done that for 200 companies, half the size of a YC batch. I've done this for personally. So for founders, it doesn't take very much time, you know. If you have the contact list, if those people trust you, right, you can do it with one email and then a bunch of follow-up intros if investors are interested. And, you know, maybe half an hour, 60 minutes with the founder, making sure their materials are good, getting them some feedback. So I think there needs to be an investment bank for all stages of company building.

That's actually a really good idea. How would you, uh, where would you, well, what would be the business model for it? So would you take a percentage of the raise? Would you take equity? Would you take a referral fee from the VCs who want this deal flow?

Would you, yeah. And you take far less than 7% of the company. You maybe take a certain percent of the amount raised, right? And then maybe a little equity. So that's what I do for earlier stages. I take, you know, anywhere from a few percent to high single-digit percent of, of the capital raised, and then I would take a little bit of equity.

And that's— you do this? Ryan does it?

I do this.

How much, how, how much money have you raised for other companies?

A ton of money.

I mean, I don't know what that means. $100 million or a billion or $10 million.

One company could be—

yeah, I mean, through intros that I've made, hundreds of millions of dollars, maybe upwards.

And they've given you a percentage of that capital?

I know I don't take a percentage of capital raised. So I used to— I sometimes do this voluntarily for free. If I like a founder, I don't take anything. And then for some, I take a little bit in advisor shares. It's usually less than a percent. It's usually less than half.

It's actually a great idea. This is actually a great idea.

Yeah, I think it's a good idea too. But here's the thing. So I used to run this conference business and it was fun and everything, but the crappy part was the more successful the conference got, meaning the more, I mean, you go, you either do more events or you have more people come or you charge more money. But the more people who came and the more successful my event got, the worst it got and it sucked. And so with this, if you were doing this, would this be like that where the bigger it got, the less you're like, oh man, he promotes everything or this brand promotes everything, you know what I mean? Yeah, totally.

You got to be picky with who, you know, who you work with, right? You can't work with 400 companies every quarter. And so sure, and a company could do this. You could start your own firm, could team up with people. You can do it as an individual founder. You can do this. So I think there's many ways to skin this cat and many different models here. So this is just a seed of a thought.

How did you build that reputation as both A, the guy who knows the investors, A, and the, the investors trust, and B, the guy that gets his fingers on the, has his fingers on the pulse of early stage companies so much so that you're helping them raise money?

Well, the secret that I'd share with any investors is treat founders really well and they'll refer other founders, right? And so some do that early on, then they have a brand and then they, you know, form an ego, right? And they forget how that brand was generated in the first place. And so the, the firm that continues with that ethos and holds onto that ethos forever is gonna build one of the greatest next generation firms, um, there is. And so I, I developed a reputation from founders for being somebody they could call about literally anything, that they don't have to mince their words, that they could trust, that has their back completely. And so, you know, my only wish is I had more time, which that's kind of the challenge, but every ounce of available time I've tried to dedicate to the next generation. And it's, you know, it's the most rewarding thing I could possibly do.

I like it. So let's give, uh, I like that idea. I think that's a good one. I've, I've said this for a while, which is that, uh, like venture investing is going into like a couple big categories. I think, I think there's like the big brands that are like, you know, their, their stamp of approval means like a lot for you, whether they're good or bad investors doesn't really matter. They're like the Harvard Stanfords of the world. That's Sequoia, YC, Andreessen, whoever else, uh, Benchmark, whatever. And then there's niche specialists that are like, oh, I know robotics better than anybody. And so I'm gonna see all the robotics companies, I'm gonna help them. And even if they get a Sequoia to invest in them, they'll also want the robotics expert in the deal. And then the last one is basically like venture services, which is, can you serve the founder in some way? So if you can help them raise their next round, uh, I think that's a, a, a smart way to basically get yourself into the right companies. If, as long as you're, as long as your filter is pretty good. All right, what else you got?

Give us another idea. Well, I think DAOs are going to change the world. So in continuation of the spirit of investing in VCs, there need to be more VC DAOs where you invest in things as a DAO.

And why is a VC DAO better than a normal, you know, either individually investing or starting a traditional fund? Why is a VC DAO better?

Because it relies on the collective intelligence of a group. I think it's transparent in terms of how it makes decisions. I think you can raise capital more publicly, and I think your actions are more kind of on a public record. So, you know, I— and frankly, the best reason is I think if you're up-and-coming aspiring investor or VC, It's way easier because you don't have to spend 5 years building relationships with LPs. You can start a public track record investing within your DAO, and that track record will, you know, talk for itself and attract more and more capital.

Right. What— have you heard of OrangeDAO? No.

What is OrangeDAO?

So OrangeDAO is basically as is what Ryan's describing, but against, you know, his enemy of the month, which is YC. So basically what it is, is it's a DAO, which means it's like a, if people don't know, it's a decentralized autonomous organization. Basically in the crypto, it's the crypto version of a company. And so what it is, is basically they made it where only a YC alumni can enter and only YC companies can get funded. So it's a, it's an organization whose mission is to fund YC companies and the, all of the investors are YC alumni. So basically it started off with like 10 or 20. Now there's 1,000 YC alumni that are in this. They provide the capital, they also provide the deal flow and the diligence and the filtering and whatever else. And then they fund YC companies. And, um, and so if you're a, if you're a YC company, you could take money from Orange DAO in addition to these other traditional funds. And with it, you're getting these thousand people. And the, and the, I think the DAO votes on the deal. So the, so somebody proposes, I think we should vote, I think we should invest in this company. And then the DAO holds a vote and it'll come back, you know, 70% say yes, 30% say no, let's invest. And it's like a, a group, group investment fund like that.

So I actually, I like Y Combinator. I think that the, like the Paul Graham, I love reading Paul Graham's work. I, I like a lot of that guys. But when you're describing this, Sean, I understand. I am also frustrated. I'm like, oh, so the rich get richer even more and more. Like, it's just a, you, it's just a, it's a circle jerk that, that is never ending. And I, that frustrates me. I don't want to, I feel like, I guess it's definitely part envy of like, well, I'm not in that crowd, therefore I miss out. And it's also part like David versus Goliath type of thing.

Yeah, I can't stand clubs. And so it's— yeah, I have that same feeling, Sam. It's just something about it doesn't feel right. And even if I was inside of it, you know, I've had the opportunity to join a lot of these clubs and I won't do it because you— it's also in your self-interest not to do it. You know, I could have obviously gotten the benefits of them, but, you know, now look at where I am, like, I'm free to do what I want and to speak up how I want. And I don't owe any favors to anybody. And so people—

but are you free, though?

Why are you free to do this? Because he's not in a tribe. He didn't— he didn't basically go into a tribe which has certain, like, rules. Yeah, but you've got—

he has 600 employees who he doesn't want to completely screw over, you know, like Some, if something bad happens to Ryan, that could negatively impact some of his people. He's got some investors looking out. I mean, I don't, I have accountability.

Maybe you're single though, to my employees and my shareholders, right? To make, make them successful and better off. And I think that's enough. Like, I don't need, I don't have all these other groups that I'm accountable to. In addition to that, that, you know, basically makes it impossible to say anything. And so I consider myself fairly free.

Where were you raised? Miami, Florida. And what did your parents do for work?

My mom worked a local secretarial job. My dad had a small business. So I grew up very middle class. I went to, you know, very lucky again to Stanford on, you know, almost entirely financial aid. So grew up without much money, went to a big public high school in Miami, 4,000 kids, grew up in a very diverse environment. So I got into breakdancing and stuff like that. So when I came to Silicon Valley and Stanford, it was like the biggest culture shock. Ever, because Miami and Silicon Valley, it's like, it couldn't be more opposite. Not anymore.

That's true. All right, did you have any other ideas you wanted to share with the audience?

Man, so here's my general theme is, and I'll reference Bolt for a second, then I'll talk about it broadly. Everything's getting decentralized. So if you think about commerce, Amazon was phase 1, right? Network effects, economies of scale, data, everything, but on one domain, amazon.com. And then phase 2 is you have Shopify, which is all of that power, network effects, economies of scale, tech scale, but on one end-to-end enclosed platform. Renzo Bolt is the network effect and the data and the tech economies of scale in a fully decentralized way. Completely unbundled, completely headless, completely tech stack agnostic. And that's why we're such a powerful force for commerce, right? That's why Maju, who's our new CEO, he centralized commerce at Amazon for 8 years, ran all the logistics, came to us because he saw it getting decentralized and thinks they have the best approach to decentralizing commerce. So I think every industry is getting decentralized. I think purchasing, you're going to see a tidal wave of purchasing platforms that help you purchase from your neighbors, purchase food locally. I think the consciousness of our society is raising. I think we want to buy and purchase things that are good for society, that are sustainable, that are recycled more than things that are flashy. You know, I think more people are going to start wearing t-shirts. And so I know that wasn't a specific idea, but those are, those are how I think about things.

And with your, with this whole new, like with you kind of coming out and doing this Twitter thing and accusing these people, it, it like a smart move. And you seem like you definitely are incredibly smart. It's like, you know, I'm mad at that this system exists and it just so happens I'm working on a solution. Um, is that what you've got up your sleeve?

Just might be.

Uh, so what are you going to do?

To, to be announced. Um, I've been working on ideas for a while. I think there are much better systems that could be created if you think creatively about incentive alignment. And I have confidence that, you know, better systems will be created, not just by myself, but for others who may see this as an opportunity to go build.

Well, you realize I agree with what you're saying. I think what you're doing is smart. But like, if I was a hater, If I was Sam Altman or whoever is like disagrees with you, I would say, oh, well, he's talking shit because he's launching a competitor. And so what, what percentage? What motive? How are they each playing into this of like, I genuinely feel this way and also I have something up my sleeve?

I wouldn't be doing this if I wasn't so distraught with how they operate. So. you know, if they were like a bastion of positivity, good advice, um, and, you know, if they were super pro-founder, I wouldn't be doing this, but I fundamentally do not think they are.

And so, you know, and they being Y Combinator. And are you are you happy right now? Or do you have like a nervous energy in the morning because of what's going on? I mean, like, I know sometimes when I do something that I like, I'm happy that I did, I wake up in the morning, I'm like, man, I'm getting a lot of hate though. Like this type of energy just bothers me. Where's your energy right now? Like Sean's thing about Clubhouse, it kinda, it wasn't like a career maker, but like, it wasn't that far from that. But like he was getting a ton of hate and like, I don't know, I didn't ask him, but maybe there was some nervous energy in the morning.

I didn't like how much I started looking at my mentions that next 24, 48 hours because I was like, oh man, like that's 2 days of my life. I kind of let my main focus be what are people's reactions to this? It was very hard to look away from that for me personally. And I'm pretty like strong-minded about this sort of thing and very like, uh, I tweeted this out the other day. I want my attention to be very expensive, but I know once you get, you know, 20 million impressions on some tweet and you're getting 50,000, you know, replies or whatever, or the heart likes or whatever, you know, that's a flood of stuff you can go look at about people talking about me, people saying things to me. What are they saying? People hating me? Do I need to defend myself? It, it was a bit of a distraction for me. Yeah.

So where's your energy right now? Are you nervous? Are you happy? Are you uptight?

Where are you? Well, I'd be lying if I said I don't care what people think. I mean, I obviously do. In fact, I'm doing this because I care what people think so much that I want the right, you know, I want my opinions out there in the world. And so, you know, people can update how they think about these things. And I'd say I'm faring with it pretty well. Like, do yoga and meditate every day, every morning, and I stay pretty calm and grounded. And, you know, I think that I feel more, more empowered than ever. Just like I've gotten so much love the last few days. It's been, you know, 95% love. And then it's all the people I expected to blast on the hate who came out of the woodworks. It was like Sequoia VC. Paul, Sam, YC. And so that's unexpected. I was actually kind of surprised at how just like crazy their messages were and how hostile they were. Like, you know, generally older, like you think they'd be wiser. But what did they say?

Where they say like, I'm gonna fuck you up. Were they gonna fight you? What did they say? I mean, like, what would they say?

Paul nitpicked on a tweet of mine about Stripe Publishing, which basically said because I focused on that, that this is mania. You know, I was manic or something like that. And then Sam, like, just, like, said something and then he, like, corrected my spelling, which is like. You know what someone—

yeah, I saw that. Why he— he— not even your spelling. He said, why combinator? It's two words, not one, right?

Yeah, exactly. Most arrogant, the most arrogant type of comment you could do.

I thought he proved my point, right? It's like, that's what you do in middle school, you know?

And then like, they might as well have just said, I know you are, but what am I? Yeah, exactly.

And then Sean was just like, you know, called it like, he's just horrifying words.

And just, you know, this guy, the guy from Sequoia, he basically was like, uh, this, you know, he's making it sound like everybody was against him, but the truth was their numbers just—

yeah, yeah, he started commenting on my metrics, like, just like, you know, that's the only thing, you know, he could point— like, first of all, VCs aren't supposed to comment on metrics. Second off, what he said was a blatant lie about our metrics. And so another just complete low blow. And so everybody who messaged me was like, all of those comments validated what you were saying. Like, these are the people you're putting on your cap table. Imagine when you'd have a disagreement with them as a founder, how they're gonna treat you.

You, um, I actually think this is gonna be a net, net win for you. I think that like there's definitely fear if I was you of like, man, is anyone going to work with me again? But I think like being a good-natured loose cannon is actually a typically a good—

loose cannon. I like that.

That's a good phrase. Loose cannon. Yeah. Cause intentions matter. Intentions matter a lot. So like if you're a loose cannon, but you just want to hurt people, that's one thing. If you're a loose cannon and you generally want to help, that's another thing that's lovable. So I actually think this is going to be a big benefit. For you? Do you— are you single? Do you live alone or do you have a girlfriend or whatever you're into? And what are they saying?

Well, I have people close with and like everyone's super supportive. They're like, dude, you're doing what no one else— what everyone was afraid of doing. And I find if you're doing things that other people are afraid to do, you're generally in the right. So, You know, it's a— for me, that's a marker of like, I'm on the right track. And yeah, they're very supportive.

Have you read the book 48 Laws of Power? I haven't, but I want to.

I heard it's epic.

You are doing it, so maybe you should go read it and try to get it all done pretty soon because you are in the middle of a lot of like different strategies that the author discusses.

Interesting. Alright, I'll go pick it up.

Yeah, and the author, his name is Robert Greene. He's got another one called The 33 Strategies of War, of which you are also doing some of that. But this is very interesting that you're like involved in this. What do you read on a— what have you read that's made an influence on this whole process of yours?

Well, I read a lot of spiritual texts, and that has given me the fearlessness to make first principle decisions. 'Cause when you're grounded in spiritual reasoning, you're not grounded in mainstream reasoning. And so that drove Conscious Culture, that drove 4-Day Workweek. I'm like, why are we working people to death? That's not healthy. Our health spiritually is very important. Sustainability, it's important spiritual concept. We have to push 4-Day Workweek. And you know, monks, certain monks, the more higher on the spectrum, wiser they are, more ascended they are, the longer their sleeves. And people are like, oh wow, it's because they're more docile. And it's not the case. It's because they're actually, you know, more combative when they see something wrong in the world. And so For me, like, I've found that kind of the further I've gone and kind of healing myself and healing those around me and going inward, the more fearlessness I've had externally. And this is one manifestation of that.

You are so strange. It is awesome. You are so cool. I've become a fan. Sean, I understand what you— what you saw in this guy when you had dinner with him.

Yeah, exactly. Um, dude, thanks, thanks for coming on. 27, 28, right?

29, 27. You are the weirdest 27-year-old I've met. That is what a unique— what a unique perspective. It just— you're, you're interesting. TBD if, if, if this battle— I hope, I hope you win this battle, but like, uh, you're definitely gonna win some big war, that's for sure.

We're looking forward to it. Fight the war. Cool, let's go.

Um, all right, so people, people should go follow you on, uh, on Twitter. I think that's the best spot. Uh, what's your handle? It's like King Ryan or something? The Ryan King. The Ryan King. Why is that your name?

I think it's fitting.

Oh my God, this is awesome.

Okay, there's a great meme. I don't know if you saw it, but you posted another— you posted the thread about the mob and the YC Mafia, then he puts another thread why YC isn't worth it. And like one of the first replies I saw was this meme of like this wife asleep and the husband's like, like reaching over to her and he goes, honey, wake up, the Bolt guy did another thread. And I thought it was so funny. So people should follow you.

That handle actually, my grandparents always used to call me the Ryan King. So call me that growing up and I'll just like, oh, it's a great handle. Let's go for it. I love it, dude.

Thanks for coming on. Appreciate it. And good luck with all the stuff going on.

Thanks, guys. Thanks, Sam. Sean, such a pleasure.

See ya. See ya. All right, Ryan just left.

All right, what'd you think? That guy's—

so like, uh, let's separate this current, like, do I think he's right or wrong? I, I don't— I haven't investigated him. I think he's right, maybe, but I don't hold that that strongly. But as a person, this guy is a killer. I'm Team Ryan, uh, just in life. This guy is so unique. Unique. Yeah.

He, uh, he's a very unique guy. He's got a very unique style of speaking. Uh, yes. Like I usually have a bias against people who speak slowly.

He talks so slow, but I loved it.

And so, um, and I've noticed that about myself that I'll like, I'll instantly kind of, okay, this person's talking slowly. Uh, if they don't like have something super interesting to say right away, I find myself tuning out. But when I met Ryan, he was talking really slowly, but then he would say one thing that would just grip me and I'd be like, wait, what? And then he would say the next, and then it would like be another minute and then he'd get me with another one and another one. I was like, wait, I think this guy might be one of the more, I was like, how old are you? He's like, I think I met him when he was 26 or 27. And I was like, you're one of the weirdest. And you said it perfectly. You, you go, you are the strangest 27-year-old I've ever met. And it's awesome. And that was my exact takeaway. And then I was like, I was leaving the dinner and I was like, um, you wanna just hang more? You wanna, uh, how about I drive you? Where are you going? And he's like, oh, that'd be great. And canceled his Uber and hopped in the car and I just drove him around. We just talked some more because I found him to just be a very, uh, interesting person. And, um, you know, I like the stuff that he stands for. Um, which is great.

In our text group ahead of this, people were saying, oh yeah, you know, he probably has sold a ton of secondary. He probably made all this money on Bitcoin and maybe that's one of the reasons why he's able to kind of be this like loose cannon and say whatever he wants. He said that that's not true. Yeah, I don't think that that's true. I don't think he's a liar.

I mean, but obviously I'm sure he's doing fine, right? Bolt's a $14 billion company now. I think, yeah, that's what I said. Get fired and his equity will still be there for him. You know, that's okay. Like, that wouldn't be, you know, I think that's the safety net. But like I had said in the thing, he's got a track record of just kind of doing things his own way. So I'm not really surprised. And I also think He didn't say anything bad. And I think actually it's a whole bunch about nothing.

He did say something bad on the pod, though. He said, I am saying that the Stripe brothers are bad. I said, I do not think they're good dudes. And he goes, no, I don't think they're good. I don't think they're good.

Yeah, but that's what I don't think. That's that bad. You're allowed to say, you know, I don't think these are— these are good dudes.

I think that's bad, man. I think that's bad. I think that that is a stripper. It's a very simple word, bad and good. But like, what's— it's like to say someone, I don't think he's— I don't think this person's a good person. That's a really strong thing to say.

I feel like we say stronger than that every episode about people we know half as much about.

But like, I, I text you that all the time. I'm like, hey, this person messaged me. I might work with them on X, Y, and Z. Are they a good person? Right. And if the answer is yes, that's it. Right. If the answer is no, that's it as well.

Now, I would say I think the things that he said that they did, I don't think are that bad at all. And again, I'm an investor in Bolt. I like Ryan, we're friends. So, you know, like I'm not agreeing with him that they're that bad even if they did it. But that's okay. Like he's totally allowed to think that those are fucked up things. I think that those are pretty much fair play, but I think it's really funny the way that people reacted to it. And I think it's really good for him and good for their brand the way people reacted to it. So Good on him for, for using them in a way to build the brand of what he's doing and also put his stake in the ground and say, this is what I think is right and wrong. I think they did wrong. You know, he's fair to say that even if my stake would have been 10 feet over to the left.

I, I— this guy's interesting. That was a good find. So I don't know where in the episode this little segment's going to go, in the beginning, in the end. But that's what we think about that guy. That guy was fascinating. I could talk to him for a long time. Yeah. I'm older than him, but I would look up to him. And I think that in his—

when he was on here, I think he was trying to do a good job representing what he stands for. I think most people do. I think most people's default, if I get invited onto a podcast, I'm going to go on, I'm going to try to say all the right things. So I think he was definitely doing a little bit of say the right things stuff. But actually having talked to him in private, he actually was very similar where he's like, I believe in this. I think it's going to be awesome. I think we're going to win. And I'd be like, yeah, but we're just shooting the shit. This is late night dinner over 2 drinks. But he was just like, I said what I said and I meant what I said. I think this is awesome. I think this is the best. I think this is totally going to work. I think blah, blah, blah. So I think he has a very singular-mindedness about what he believes in, and I think that's cool. To interact with because I think most people, A, don't believe anything. B, when they believe, they'll hedge, or C, they'll kind of be wishy-washy about it where they believe when the lights are on and then when the lights are not on, they're, you know, why are you applying for a job? I thought you just said this is the company that's going to win. Oh yeah, yeah. Just in case, you know, like there's a wishy-washiness to a lot of people. I've— he has zero wishy-washiness.

So, you know, for better or for worse. And I, I'm upset at myself. I judged him as being far different just by looking off his profile picture. Uh, what'd you think? He was not just that. He was this, like, I thought he was what people accused me of being, of this like blonde hair, white bro who had everything in life handed to them, who, um, is going to be kind of, um, maybe not as intellectual, kind of a, uh, an alpha, right? You know, like this, this stereotype that it's not an insult necessarily, but I wouldn't be proud of.

Like, they just think I'm just like a good-looking, strong, muscular, successful guy, and I just feel like it's unfair.

Well, I'm not talking about myself, but like with him, I'm like, well, because he went to Stanford, he dropped out of Stanford, was in Bitcoin forever, so was like crazy rich at a young age. He said he's from Miami, so in my head I'm like, yeah, oh, okay, fun. I paid you. Yeah, this is like, this is the thing that you're calling life is a game for you. And in reality, he was incredibly intellectual, very intriguing. I believe him that he, that like, I understand that you can be very wealthy on paper, but like he hasn't sold a lot of stuff. So like, that's an interesting perspective. So I thought he was cool, different than what I thought he was going to be. I enjoyed it. Yeah. Uh, cool.

Let us know what you think. If you want us to do kind of more of these or less of these, uh, you could tweet at us and, uh, you know, we take it into consideration. We don't necessarily listen, but we, we like to know what you think, and then we may or may not do it.