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

Ryan Breslow

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

Sam Parr

don't chickens have 2 wings

Shaan Puri

yeah but it's not their actual wing hey what's up ryan

Ryan Breslow

what's up sean sam

Sam Parr

what what is it

Shaan Puri

Dude, you can settle this for us. So, Sam, this is Ryan. He's the founder of Bolt, and 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?

Ryan Breslow

I think they're the wings

Sam Parr

what's a drumstick

Shaan Puri

you think they're the actual wings I feel like they're not the wings yeah I feel like this

Sam Parr

This is like a... such a stupid conversation. Of course they are like, "What's a drumstick?" Isn't a drumstick a leg?

Shaan Puri

**Pow! Powerful young Ben. Ben, look that up. See if I'm right; I think I'm right. Alright, so we should switch gears.** **Okay, so Ryan's here. I met Ryan in... where are we hanging out? LA? Okay, I was in LA at this dinner. Ryan's across the table from me, and at this dinner, everybody's kind of dressed up because it was at the owner's house of an NBA team. 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 wearing this tie-dye shirt, and he looks totally different than every other kind of business schmuck at this thing. I was like, "Oh, what's up, man? What's your...?" I was literally in my head thinking this guy's definitely a TikToker or a YouTuber. He's got this charisma about him.** **And he's like, "No, I'm Ryan. I started a payments company." I said, "Oh, what is it?" He said, "Bolt." I was like, "Oh, shit! I know Bolt! That's amazing!" We ended up becoming friends, and I ended up investing in the company. You ended up getting Twitter famous over the last few months, my friend.** **I wanted to have you on to talk about a couple of things. You've done some pretty impressive stuff at a young age. I want to give people the background on that, and then you currently have some spicy Twitter stuff 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.**

Ryan Breslow

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.

Shaan Puri

and sam what do you know about ryan besides what I just told you

Sam Parr

So, I was Googling you, and I saw your Twitter come out of nowhere about a month and a half ago. Sean told me all about Bolt and he mentioned this dinner that he had. So, Bolt is a payments company that is valued at around $11 billion to $14 billion. 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 $1 billion, including a bunch of crypto stuff. When I was Googling you today, one of the first images that came up was beautiful because you're tweeting about mobs and mafias. The Forbes headline is "Meet the Stanford Bitcoin Mafia," and there was a picture of you and like 3 friends. So, I know you've got your hands in a bunch of stuff.

Shaan Puri

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

Ryan Breslow

Well, my claim to fame is that I think I operate pretty fearlessly. I've done a lot of things that I've been told I shouldn't be doing. In business, I've been told by many people that what I'm doing would never be possible. We've written the framework on culture at Conscious.org. People are like, "Who are you to write about culture?" Now, I have close to 100 companies pledging to that culture. We've written books and implemented four-day work weeks. So, I think we're thinking differently—myself and the whole Bolt team—and I'm very proud of that.

Shaan Puri

And so, walk us through the... I don't want to go too far into what Bolt is. I'll give kind of like the TL;DR on it. I'll oversimplify it; you might cringe a little bit as I oversimplify it. But basically, the way we pay for things online is... you know, some people shop at Amazon, and Amazon says, "Hey, one-click checkout! We got your stuff saved." Then you have Shopify. Shopify has a bunch of stores, and 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 has Apple Pay; they let you pay at some places. What you've done is you went to... like, you're like, "Hey, you know, even though 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 Pinterest where people go and they find products they love, and they love to be able to check out. As somebody who owns an e-commerce store, I felt this pain many, many times. You can look at how many people just drop off at the checkout because they don't want to type in 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. I'm just seeing, like, that's the biggest drop-off in our whole store, and 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 they don't have to type in the same information over and over again. And it has this network effect where the more stores that 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 going to work on Amazon, and Shopify is going to work on Shopify, but the world is a lot bigger than that. Alright, how did I do out of 10? Did I get it, or what did I miss?

Ryan Breslow

Sean, that was pretty epic! We need to put you in customer calls.

Shaan Puri

Yeah, there we go. I'm down. 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's an actual story that happened there where somebody kind of told you, "Look man, it's not gonna work"?

Ryan Breslow

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

Sam Parr

What were you doing before this? Before Bolt, I want to hear all about that.

Ryan Breslow

Sean mentioned that I dropped out of school, so let me share a little bit about my background. My first job was bagging groceries, and I did that for three years. Then, I started going to the internet to make money. I began some websites and online businesses, and I ran a web development agency, working for a lot of other customers. That's where I learned everything there is to know about e-commerce. I was lucky to get into Stanford and started the Stanford Bitcoin Group with some friends in early 2013, many of whom have gone on to do amazing things. I dropped out of school in 2014 to focus entirely on crypto. I believed that crypto was going to change everything about payments, which I still believe. However, about a year in, around mid-2015, I thought, "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 and important shopper network payment network on the planet. This was a vision I couldn't unsee, so I decided to really learn about the space. The more I learned, the more I realized this was an opportunity. So, we started building, and yeah, that's the story.

Sam Parr

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

Ryan Breslow

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 have a little bit of crypto, I mean, you know.

Sam Parr

but you you you you didn't become you know f you rich

Ryan Breslow

No, not at all. I had to bolt. I had to make it. I was couch surfing; I didn't have enough money to even rent a place to stay. So, I was...

Sam Parr

A friend texted me before this podcast and he said, "Ask him how wealth is like." Well, he already got really wealthy from Bitcoin. Is that why he's like so brash now? You've kind of just answered that question; you weren't...

Ryan Breslow

Weren't. At Bolt, I started off with a $40,000 salary, and for about 5 years, it never got higher than $60,000. I was living paycheck to paycheck. I wanted every dollar to maximize Bolt's outcome. Just recently, I sold a very tiny amount of shares just to kind of pay for some expenses. But up until a month ago, I hadn't sold a single share in almost 8 years into the journey.

Sam Parr

what about your other businesses you you didn't sell any of those either

Shaan Puri

Also, I helped start Eco Right, now known as Eco. Your buddy runs it, I think. What's the name?

Ryan Breslow

and he's super

Shaan Puri

Like, impressive as well. Yeah, and I don't want to go too much into ICO because your Twitter stuff's frankly just more spicy right now. But basically, you kind of helped with the vision of that or the initial strategy of that.

Ryan Breslow

Yeah, so what I can't take credit for is that I helped build an awesome team of founders and inspired some of the ideas. However, they have really manifested Eco into what it has become today. The founders there have driven an amazing vision. They are the ones who are on the ground every day, and they've executed. So, I've played a part in the journey, but Andy Bromberg is one of the CEOs I have the most respect for on the planet. Henry Alt, Ryan Sachs, and Joey Krug have done miracle work.

Shaan Puri

Cool. So, let's talk about this Twitter thing. You came out the other day and you basically said, "Look, you're like Bolt. We’ve become successful now, but it wasn't without some challenges." There are the normal business challenges, and then there are the challenges of the powers that be. In Silicon Valley, there are two entities that are very powerful. In most people's minds, I think you chose to fight with people that very few have bad things to say about: Y Combinator and Stripe. Stripe is probably the most beloved startup in Silicon Valley—respected and beloved, whatever. Y Combinator is also the most powerful brand. It's like, if you're going to pick on a college, you pick on either Stanford or Harvard if you're going for the top. You basically told the story about them being the mafia. So, I want you to quickly bullet your argument for people who aren't nerding out on Twitter and haven't seen it, because the audience we have here is not going to have seen it. So, bullet it out for us.

Shaan Puri

That and then I got some questions for you

Ryan Breslow

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

Sam Parr

But, yeah, what I... you're... 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... like, what does "institution" mean? And, are you able to, like, actually...?

Shaan Puri

Well, let's separate this out. There are fair business games, which is like we're competing against somebody that's fair. They can compete with us fiercely. Then there are investors just deciding, "This space is too competitive," or "Stripe's gonna win, I'm just gonna back away." That's more of a perception thing, and nobody would say that that's unfair. Can you talk about the specifics of what you felt was unfair or where there was some heavy-handedness to it?

Ryan Breslow

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

Shaan Puri

but how do you know that that's what happened right they might just come to you and say we're not just

Ryan Breslow

The stripe would always come up somehow in that conversation. So many of them pulled me directly. Other investors said directly, "I got a call by Stripe and they told me I can't invest in you guys."

Sam Parr

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

Ryan Breslow

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

Shaan Puri

and then they say you're conflicted out right that's a competitor of ours you're our shareholder donut

Ryan Breslow

Right, exactly. I didn't even consider ourselves a direct competitor at the time, but I think they're very guarded about anything in their periphery. I've heard the same story from companies doing card issuing. I've heard the same stories from companies doing subscription payments. Then Stripe would roll out their own product next. 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.

Sam Parr

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

Ryan Breslow

I've never pulled a single investor. You can't invest in somebody, right? To me, everything is fair competition. If someone wants to invest in a company tangential to me, I tell them, "Go for it." We've even invested in tangential companies. I've invested in tangential companies because I think innovation is good. I have a very long-term perspective. So when you're calling and saying you can invest in this company, even if they're not on the Stripe cap table, there are investors who are not on the Stripe cap table. To me, that's just not how I would do business. I also want to help found the next generation of founders to go into building with their eyes wide open. I invested eight years of my life into this business without knowing about the games that go on. The most important thing I'm exposing here is that if you're coming to Silicon Valley with an idea, quitting your job, and putting a lot on the line, get ready for war. It's serious, and there will be people who do not want you to exist. You're going to need to be ready to battle that.

Shaan Puri

And so, one of the things you say is that they basically hurt our ability to fundraise by playing a good game of theory. They got every big investor to get a little piece of Stripe because every investor wants a piece of Stripe. Then they said, "Cool, now you're conflicted out of investing in our competitors." Some might say that's shady. I personally, as an investor in you and a fan of yours, would just say, "Okay, there's nothing unethical about that." You may not like it, but that's competing. It's a strategy—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 you get bonus points of respect from me for that, but I also don't think you did anything illegal or completely crooked. You copied something that was copyable. Okay, fair enough. The second thing you said is that Y Combinator, which has a huge stake in Stripe, controls Hacker News. They own Hacker News, and on Hacker News, people would be posting about Bolt. It would get some play and go up the ranks, but somehow there are some 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 higher. You posted some examples of that. Now, I think that's the summary of what you said. As that was happening, did you have a suspicion, or are you like, "I know that that's what happened"? Sure.

Ryan Breslow

That's what happened, you know? Because we had some posts, one in particular that I had written catered to the 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 one and held there. We had a ton of comments on it—just very active people, very interested. You can go read all my comments. Then, Stripe's post, I don't know if it was there before, but it seems like they said it got posted technically before. Anyway, after it got to number one, theirs started to rise and ours just started to fall and then disappeared. I don't know if it was editorial. There's also this downvote functionality, so you can 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.

Sam Parr

Right. The guys who started Stripe, the Collison brothers, I don't know them, but they seem, from the outside, like good dudes. Do you think that is the case?

Shaan Puri

do you know them

Sam Parr

and is that is that a character characterization that you'd challenge

Ryan Breslow

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.

Sam Parr

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

Shaan Puri

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

Ryan Breslow

so stepping up into executive chairman

Shaan Puri

I like it. I like it. Nice! That's interesting.

Sam Parr

you like come up at the shower and at bed at night you write it down

Ryan Breslow

you know that was actually the truth and

Shaan Puri

I know you

Ryan Breslow

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

Sam Parr

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

Ryan Breslow

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

Shaan Puri

right you're

Sam Parr

you're crazy I like it

Shaan Puri

Yeah, I respect that. I also respect the move, not the CEO part. Alright, great. That's fine. I don't know anything about that, but for the content that you're putting out... So we've talked before about how to pick a fight. In fact, there's a passage from a book called *Rework* titled "Pick a Fight." It's a marketing strategy, and it's like a two-page thing. I remember earlier on the pod, I literally read it word for word because I was like, "This is a great idea." I think this is when the guys from 37 Signals were picking a fight with Apple, saying, "You know, this is not right." Or Epic Games from *Fortnite* was picking a fight with Apple. We talked about how there's an art to doing this. First, you can't just completely make something up, right? You have to have an 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 whoever holds the power. When you do that, you're going to get this groundswell of attention, support, and other stories will come out of the woodwork that will make you seem even more credible. You'll get your name out there. So, you know, I don't know how many people knew about Bolt before this. Checkout technology is not the most in-your-face; it's not Snapchat. It's not like a product everybody uses. But a lot more people know about it now. How conscious were you? I mean, how strategic was it that you were thinking, "You know what? I think if we come out with the story, yes, I'll be helping people understand how the game is played, but I think this will be good for Bolt too?"

Ryan Breslow

Yeah, I mean, I think doing what you believe to be right will always pan out in the end. So, I stand by this decision. I think it's great for both. 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. What I wrote to my team when I was doing this was, "Just because our company is worth $1,000,000,000, I'm not going to become a sellout founder." 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. For me, it was a way of telling the world who I am as a leader. I'm trying to set an example of fearless leadership for the next generation of founders because I think we lack it. I can't find too many leaders in this country who are truly fearless and who stand up for what they believe in. I think a lot of leadership is fear-based, and I think we have to kill that.

Sam Parr

I agree with you. I'm entirely on board with you. I think the... I don't actually think this is my stance, but in fact, it's not my stance. At first, it was, but it's changed a bit. I don't know if what you're saying is necessarily true. I saw a lot of people who used to have your position, like Sam Altman and Gary Tan. They're not underdogs anymore; now they're like "the man," you know, the folks in charge. But they're saying, "This guy Ryan is lying. He's false. He's just full of it." So it's 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 cool kid group, and it's always fun to stick it to that cool group.

Shaan Puri

Kid group, honestly, the things you said that they did—this is actually credit to you. The things that you said they did are not even that bad. 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 gonna know how to prove it. It kind of doesn't really matter. I think you pointed out the overall power dynamic, and that's what was important. Then you just got your story out there about who you are and what your point of view is. Whether people agree with you or not, that's their choice. But I think it actually emphasizes how brilliant the tactic was. 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 accusations are true, it's not. But it got so much play because, A, you're a good writer, and B, everybody is so afraid to say a word against them. I got one of my most viral tweets when I came out and said, "Clubhouse is gonna fail, and here's why I think it goes down." 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 it was. 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, all you could talk about is the product, it's gonna fail. I got privately a bunch of messages from high-profile people who were like, "Dude, I can't retweet this to show support for this just because of, you know, politics, but I totally agree with you." Or like, "I'm glad somebody fucking said it. I don't believe in this shit at all." I had one person—these are all blue check marks—saying, "Dude, people must be smoking crack if they think that this thing's gonna work." So did you get like the DM backchannel support of people who are like, "Look, I can't come out, and I don't wanna get YC on my bad side, but dude, you're so right. 100%. You know exactly."

Ryan Breslow

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. A hundred founders reached out to me, thanking me. Many of them shared their stories with me about what encounters they've had. You know, this stuff has happened; this stuff is rampant. So yeah, I had all of those messages.

Shaan Puri

all all you were missing you needed a movement people could could rally behind and

Ryan Breslow

say a hashtag

Shaan Puri

yc has done this to me also

Sam Parr

and the

Ryan Breslow

problem is why is everyone so afraid right

Sam Parr

well why are you asking that question you know the answer

Shaan Puri

right you

Sam Parr

You already said the answer, which is you'd be significantly more financially successful if you just were to shut up. So that's why I asked you that question: Are you already very financially successful on paper? Just on paper, you're set. But that's why I was asking: Do you have this like crazy Bitcoin stash? Did you have this other stuff?

Shaan Puri

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

Sam Parr

but that's what I was asking

Shaan Puri

I I wanted to know

Sam Parr

I wanted

Ryan Breslow

to know

Shaan Puri

Focus on Bitcoin. When Bitcoin was nothing at that time, that was fearlessness. Starting a payments company to compete in one of the most vicious fields, where everybody tells you—everyone who's smart and that you respect—tells you that this isn't going to work. That's fearless. Number two, going on the four-day work week, basically saying, "We're only going to do four-day work weeks because I believe in X, Y, Z" in terms of company culture, coming out against Y, Z. Right? So that's actually several of these, kind of like... you know, it's like when I invest in something, I look for a breadcrumb trail. It's like, "Oh, actually, I see a trail of this person doing really bold things or clever things or hacking different systems." I think their next thing is just going to be more of that. And so, you know, I think that's pretty cool. I wanted to switch gears a little bit and ask you... you are an idea guy. In fact, when we were driving home from dinner, you were telling me about different ideas. I was like, "How'd you get the idea for Bolt? How'd you get the idea for Eco?" I just kind of got the sense that you're an idea guy, but you've been fully locked in for eight 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?

Ryan Breslow

I brought some

Shaan Puri

Okay, fire them off and we will react to them. So, you give us the quick pitch and we'll react.

Ryan Breslow

This is a big one. I think a lot of people are going to 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.

Shaan Puri

okay

Ryan Breslow

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 Y Combinator (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 the company that's being introed.

Shaan Puri

you're a serial number

Ryan Breslow

Literally, somebody needs to do this. That's what I do personally. I've probably done that for 200 companies, which is half the size of a Y Combinator (YC) batch. For founders, it doesn't take very much time. If you have the contact list and those people trust you, you can do it with one email and then a bunch of follow-up introductions if investors are interested. It may take about half an hour to 60 minutes with the founder, making sure their materials are good and giving them some feedback. So, I think there needs to be an investment bank for all stages of company building.

Shaan Puri

That's actually a really good idea. How would you... where would you... 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?

Ryan Breslow

I mean, you take far less than 7% of the company. You maybe take a certain percentage 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 digits of the capital raised, and then I would take a little bit of equity. And that's it.

Sam Parr

you do this ryan does

Ryan Breslow

this I do this

Sam Parr

how much how how how much money have you raised for other companies

Ryan Breslow

a ton of money I mean

Sam Parr

I don't know what that means a 100,000,000 or a 1000000000 or a 10,000,000

Shaan Puri

through one company can be yeah

Ryan Breslow

I mean through intros that I've made 100 of 1,000,000 of dollars maybe upwards

Sam Parr

and they've given you a percentage of that cap not

Ryan Breslow

I know I don't take a percentage of capital raised. I used to, and sometimes I 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 adviser shares. It's usually less than 1%. It's usually less than half a percent.

Shaan Puri

actually a great idea it's actually a great idea

Sam Parr

Yeah, I think it's a good idea too. But here's the thing: I used to run this conference business, and it was fun and everything. However, the crappy part was that the more successful the conference got—meaning the more events you do, or the more people come, or the more money you charge—the worse it got. So, with this, if you're doing this, would it be like that? Where the bigger it got, the less your... like, "Oh man, he promotes everything," or "this brand promotes everything." You know what I mean?

Ryan Breslow

Yeah, totally. You have to be picky with who you work with, right? You can't work with 400 companies every quarter. Sure, a company could do this. You could start your own firm, team up with people, or do it as an individual founder. You can approach this in many ways. I think there are many different models here, so this is just a seed of a thought.

Sam Parr

How did you build that reputation as both a) the guy who knows the investors and the investors trust, and b) the guy that has his fingers on the pulse of early-stage companies? So much so that you're helping them raise money.

Ryan Breslow

Well, the secret that I'd share with any investors is to **treat founders really well**, and they'll refer other founders. Some do that early on, then they have a brand, and then they form an ego. They forget how that brand was generated in the first place. The firm that continues with that ethos and holds on to that ethos forever is going to build one of the greatest next-generation firms there is. I developed a reputation from founders for being somebody they could call about literally anything. They don't have to mince their words; they can trust that I have their back completely. My only wish is that I had more time, which is kind of the challenge. But every ounce of available time, I've tried to dedicate to the next generation. It's the most rewarding thing I could possibly do.

Shaan Puri

I like it! So, let's give it a try. I think that's a good idea. I've said this for a while: venture investing is going into a couple of big categories. I think there are the big brands that, you know, their stamp of approval means a lot for you. Whether they're good or bad investors doesn't really matter. They're like the Harvard, Stanford, and Sequoia, Y Combinator, Andreessen, and Benchmark of the world. Then, there are niche specialists who say, "Oh, I know robotics better than anybody, so I'm going to see all the robotics companies. I'm going to help them." Even if they get a Sequoia to invest in them, they'll also want the robotics expert in the deal. The last category is basically venture services. This is about whether you can serve the founder in some way. If you can help them raise their next round, I think that's a smart way to get yourself into the right companies, as long as your filter is pretty good. Alright, what else you got? Give us another idea.

Ryan Breslow

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.

Shaan Puri

And why is a VCDAO better than either individually investing or starting a traditional fund? Why is a VCDAO better?

Ryan Breslow

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 an up-and-coming aspiring investor or VC, it's way easier. You don't have to spend five 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.

Shaan Puri

right what have you have you heard of orangedao

Sam Parr

no what is orangedao

Shaan Puri

So, OrangeDAO is basically what Ryan is describing, but against his enemy of the month, which is Y Combinator (YC). Essentially, it is a DAO, which stands for Decentralized Autonomous Organization. This is the crypto version of a company. What it does is create a space where only YC alumni can enter, and only YC companies can get funded. It is an organization whose mission is to fund YC companies, and all of the investors are YC alumni. It started off with about 10 or 20 members, and now there are 1,000 YC alumni involved. They provide the capital, deal flow, diligence, filtering, and whatever else is needed to fund YC companies. If you're a YC company, you can take money from OrangeDAO in addition to other traditional funds. With this, you're getting access to these 1,000 people. I believe the DAO votes on the deals. So, when someone proposes, "I think we should invest in this company," the DAO holds a vote. It might come back with 70% saying yes and 30% saying no. Then, they decide to invest. It's a group investment fund structured like that.

Sam Parr

So, I actually like Y Combinator. I think that the work of Paul Graham is great; I love reading his work. 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." It's just a... it's a circle jerk that is never-ending, and that frustrates me. I don't want to feel like I guess it's definitely part envy of, "Well, I'm not in that crowd, therefore I miss out." It's also part of the David versus Goliath type of thing.

Ryan Breslow

Yeah, I can't stand clubs. I have that same feeling, Sam. There's just something about it that doesn't feel right. 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. It's also in your self-interest not to do it. I could've obviously gotten the benefits of them, but now look at where I am. I'm free to do what I want and to speak up how I want. I don't want to owe any favors to anybody.

Sam Parr

but you are are are you free though why are why are you free to do this

Ryan Breslow

because

Shaan Puri

Because he's not in a tribe. He didn't basically go into a tribe which has certain rules.

Sam Parr

That you've got to divide. He's got 600 employees who he doesn't want to completely screw over. You know, like if something bad happens to Ryan, that could negatively impact some of his people. He's got some investors to fill out. I mean, I don't...

Ryan Breslow

I have accountability maybe

Sam Parr

you're single though

Ryan Breslow

To my employees and my shareholders, right? To make them successful and better off. I think that's enough. I don't need all these other groups that I'm accountable to in addition to that, which basically makes it impossible to say anything. So, I consider myself fairly free.

Sam Parr

where were you raised

Ryan Breslow

miami florida

Sam Parr

and what did your parents do for work

Ryan Breslow

My mom worked a local secretarial job, and my dad had a small business. So, I grew up very middle class. I was very lucky to attend Stanford on almost entirely financial aid. I grew up without much money and went to a big public high school in Miami with 4,000 kids. I grew up in a very diverse environment, which led me to get into breakdancing and stuff like that. When I came to Silicon Valley and Stanford, it was like the biggest culture shock ever because Miami and Silicon Valley couldn't be more opposite.

Sam Parr

not anymore

Ryan Breslow

that's true

Shaan Puri

alright did you have any other ideas you wanted to share with the with the audience

Ryan Breslow

Man, I have a general theme I want to discuss. I'll reference Bolt for a second, and then I'll talk about it broadly. Everything is getting decentralized. If you think about commerce, Amazon was phase one, right? It brought network effects, economies of scale, and data, but all on one domain: Amazon.com. Then, phase two is Shopify, which has all that power—network effects, economies of scale, tech scale—but on one end-to-end enclosed platform. Now, Renzo Bolt represents the network effect, the data, and the tech economies of scale in a fully decentralized way. It's completely unbundled, completely headless, and completely tech stack agnostic. That's why we're such a powerful force for commerce. Right? That's why Maju, our new CEO, centralized commerce to Amazon for eight years. All the logistics came to us because he saw it getting decentralized and thinks they have the best approach to decentralizing commerce. I believe every industry is getting decentralized. In purchasing, you're going to see a tidal wave of purchasing platforms that help you buy from your neighbors and purchase food locally. I think the consciousness of our society is raising. We want to buy and purchase things that are good for society—things that are sustainable and recycled—more than things that are flashy. I think more people are going to start wearing T-shirts. So, I know it wasn't a specific idea, but that's how I think about things.

Sam Parr

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

Ryan Breslow

just might be

Sam Parr

so what are you gonna do

Ryan Breslow

To be announced. 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. I have confidence that better systems will be created, not just by myself, but for others who may see this as an opportunity to go build.

Sam Parr

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 disagrees with you—I would say, "Oh, well, he's talking shit because he's launching a competitor." So, what percentage, what motive, how are they each playing into this? It's like, I genuinely feel this way and also I have something up my sleeve.

Ryan Breslow

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

Sam Parr

And they, being Y Combinator, 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 it. I wake up in the morning and I'm like, "Man, I'm getting a lot of hate." That type of energy just bothers me. Where's your energy right now? I like Sean's thing about Clubhouse. It kind of wasn't like a career maker, but it wasn't that far from that. He was getting a ton of hate, and I don't know, I didn't ask him, but maybe there was some nervous energy in the morning.

Shaan Puri

It's just like I didn't like how much I started looking at my mentions in the next 24 to 48 hours. I was like, "Oh man, that's two days of my life." I kind of let my main focus be on what people's reactions to this were. It was very hard to look away from that for me personally, and I'm pretty strong-minded about this sort of thing. 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 replies or whatever, or the heart likes, that's a flood of stuff you can go look at. It's about people talking about me, people saying things to me. What are they saying? People hating me? Do I need to defend myself? It was a bit of a distraction for me.

Sam Parr

Yeah, so where's your energy right now? Are you nervous, happy, or uptight? Where are you?

Ryan Breslow

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 opinions out there in the world. I want people to update how they think about these things. I've been faring with it pretty well. I do yoga and meditate every day, every morning, and I stay pretty calm and grounded. I feel more empowered than ever. I've received so much love in the last few days—it's been 95% love. Then, there are all the people I expected to blast with hate who came out of the woodworks, right? It was like Sequoia VC, Paul, Sam, YC. That was unexpected. I was actually kind of surprised at how crazy their messages were and how hostile they were. Generally, I think they'd be wiser, being older and all.

Sam Parr

What did they say? What did they say? Like, "I'm gonna... I'm gonna... I'm gonna fuck you up." Are they gonna fight you? What did they say? I mean, like, what would they say?

Ryan Breslow

Paul nitpicked on a tweet of mine about Stripe Publishing. Basically, he said that because I focused on that, this is mania. You know, [he implied] I was manic or something like that. And then Sam... like just commented something, and then he corrected my spelling, which is like, you know, someone in... yeah.

Sam Parr

I saw that why he he he well not even your spelling he said white commator it's 2 words not white

Shaan Puri

right yeah exactly most most arrogant most arrogant type of company you could do I thought that

Ryan Breslow

Proved my right. It's like, that's what you do in middle school, you know?

Shaan Puri

then like they might as well have just said I know you are but what am I yeah exactly and then

Ryan Breslow

Sean was just like, you know, calling it... he used just horrifying words. And just, you know, this guy.

Shaan Puri

The guy from Sequoia, he basically was like this, you know, he's making it sound like everybody was against him. But the truth was, their numbers just went down.

Ryan Breslow

Yeah, he started commenting on my metrics, like, you know, it's the only thing he could. First of all, VCs aren't supposed to comment on metrics. Second off, what he said was a blatant lie about our metrics. So, another complete low blow. Everybody who messaged me was like, "All of those comments validated what you were saying. 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."

Sam Parr

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

Shaan Puri

natured loose cannon I like that that's a great addition

Sam Parr

Yeah, because 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?

Ryan Breslow

Well, I have people close to me, and everyone's super supportive. They're like, "Dude, you're doing what no one else was afraid of doing." I find that if you're doing things that other people are afraid to do, you're generally on the right track. For me, that's a marker that I'm on the right track. And yeah, they're very supportive.

Sam Parr

have you read the book 48 laws of power

Ryan Breslow

I haven't but I want to I heard it's epic

Sam Parr

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

Ryan Breslow

alright I'll go pick it up

Sam Parr

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

Ryan Breslow

Well, I read a lot of spiritual texts, and that has given me the fearlessness to make first principle decisions. When you're grounded in spiritual reasoning, you're not grounded in mainstream reasoning. That drove conscious culture and the four-day work week. I'm like, "Why are we working people to death? That's not healthy." Our health, spiritually, is very important. Sustainability is an important spiritual concept. We have to push for the four-day work week. You know, certain monks, the higher they are on the spectrum of wisdom, the longer their sleeves. People are like, "Oh wow, it's because they're more docile." That's not the case. It's because they're actually more combative when they see something wrong in the world. For me, I found that the further I've gone in healing myself and those around me, and going inward, the more fearlessness I've had externally. This is one manifestation of that.

Sam Parr

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

Shaan Puri

Yeah, exactly, dude. I mean, thanks for coming on. 28... 28, right? 29?

Sam Parr

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

Ryan Breslow

we're looking forward to it fight the war cool

Shaan Puri

Let's go! Alright, so people should go follow you on Twitter. I think that's the best spot. What's your handle? It's like King Ryan or something.

Ryan Breslow

the ryan king

Shaan Puri

the ryan king why why is that your name

Ryan Breslow

I think it's fitting

Shaan Puri

Oh my God, this is awesome! Okay, there's a great meme. I don't know if you saw it, but you posted another thread about the mob and the YC mafia. Then you posted another thread on why YC isn't worth it. One of the first replies I saw was this meme of a wife asleep, and the husband is reaching over to her. He goes, "Honey, wake up! The Bolt guy did another thread." I thought it was so funny! So, people should follow you.

Ryan Breslow

That handle, actually, my grandparents always used to call me the "Ryan King." So, they called me that growing up, and I was just like, "Oh, it's a great handle. Let's go for it!"

Shaan Puri

I love it dude thanks for coming on appreciate it and good luck with all the all the stuff going on

Ryan Breslow

thanks guys thanks sam sean such a pleasure see you

Shaan Puri

see you

Sam Parr

alright ryan just left

Shaan Puri

alright what'd you think

Sam Parr

That guy's so... like, let's separate this. Currently, do I think he's right or wrong? I haven't investigated him. I think he's right... maybe. But I don't hold that that strongly. As a person, this guy is a killer. I'm team Ryan, just in life. Yep, this guy is so unique.

Shaan Puri

**Unique.** Yeah, he's a very unique guy. He's got a very unique style of speaking.

Sam Parr

yes

Shaan Puri

like I I usually have a bias against people who speak slowly

Sam Parr

oh he talks so slow but I loved it

Shaan Puri

And so, I've noticed that about myself. I'll instantly kind of tune out if a person is talking slowly and doesn't have something super interesting to say right away. But when I met Ryan, he was talking really slowly. However, he would say one thing that would just grip me, and I'd be like, "Wait, what?" Then he would say the next thing, and it would be another minute before he hit me with another one, and another one. I was like, "Wait, I think this guy might be one of the more interesting people I've met." I asked him, "How old are you?" He said he was 26 or 27 when I met him. I told him, "You are the strangest 27-year-old I've ever met, and it's awesome." That was my exact takeaway. As I was leaving the dinner, I asked him, "Do you want to hang out more? How about I drive you? Where are you going?" He said, "Oh, that'd be great," and he canceled his Uber and hopped in the car. We just drove around and talked some more because I found him to be a very interesting person, and I really like the stuff that he stands for, which is great.

Sam Parr

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 loose cannon and say whatever he wants." He said that that's not true.

Shaan Puri

yeah and I don't think that that's true

Sam Parr

think he's a liar

Shaan Puri

I mean, but I obviously don't... I'm sure he's doing fine, right? Bolt's a $14,000,000,000 company now, I think he...

Sam Parr

knows then that's what I said

Shaan Puri

He got 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. I also think he didn't say anything bad, and all I think is actually it's a whole bunch about nothing.

Sam Parr

He did say something bad on the pod, though. He said, "I am saying that the Stripe brothers are bad." I asked, "Are you the good dudes?" and he replied, "No, I don't think they're good. I don't think they're good."

Shaan Puri

yeah but that's

Sam Parr

what he I

Shaan Puri

I don't think that's that bad. You're allowed to say, "I don't think these are good, dude."

Sam Parr

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

Shaan Puri

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

Sam Parr

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?"

Shaan Puri

right

Sam Parr

and if the answer is yes that's it

Shaan Puri

right

Sam Parr

if the answer is no then that's it as well

Shaan Puri

Now, I would say, I think the things that he said they did are not that bad at all. Again, I'm an investor in Bolt. I like Ryan and our friends, so, you know, I'm not agreeing with him that they're that bad, even if they did it. But that's okay. He's totally allowed to think that those are messed up things. I think those are pretty much fair play. But I think it's really funny the way that people reacted to it. I think it's really good for him and good for their brand the way people reacted to it. So good on him 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 he did wrong, you know? He's fair to say that, even if my stake would have been 10 feet over to the left.

Sam Parr

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

Shaan Puri

I think that when he was on here, he was trying to do a good job representing what he stands for. I think most people do that. If I get invited onto a podcast, I'm going to try to say all the right things. I think he was definitely doing a little bit of that, but actually having talked to him in private, he was very similar. He was like, "You know, 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 this late-night dinner over two 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." 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 do believe, they'll hedge, or c) they'll kind of be wishy-washy about it. They believe when the lights are on, and then when the lights are not on, they're like, "Why are you applying for a job? I thought you just said this is the company that's going to win." And then they're like, "Oh yeah, just in case..." There's a wishy-washiness to a lot of people, but he has zero wishy-washiness. So, you know, for better or for worse.

Sam Parr

I'm worse, and I'm upset at myself. I judged him as being far different just by looking at his profile picture.

Shaan Puri

what'd you think

Sam Parr

He was not just that. I thought he was what people accuse me of being: this blonde-haired, white bro who had everything in life handed to him. He was going to be kind of maybe not as intellectual, kind of an alpha, right? You know, like this stereotype that it's not an insult necessarily, but I wouldn't be proud of it.

Shaan Puri

of it if

Sam Parr

that would

Shaan Puri

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

Sam Parr

Well, I'm not talking about myself, but with him, I'm like, "Well, because he went to Stanford, he dropped out of Stanford, was in Bitcoin forever, so he 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, fun, fun. I paid you." Yeah, this is like this thing that you're calling life is a game for you, right? In reality, he was incredibly intellectual and very intriguing. I believe him that, like, I understand that you can be very wealthy on paper, but he hasn't sold a lot of stuff. So, like, that's an interesting perspective. I thought he was cool, different than what I thought he was going to be. I enjoyed it.

Shaan Puri

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