Ryan King, founder of Bolt (valued at $14B), joins Sam and Shaan to explain why he publicly called out Stripe and Y Combinator as the “mob bosses” of Silicon Valley — accusing them of pressuring investors to avoid funding Bolt. He shares how eight years of fearless decision-making, from dropping out of Stanford to launching a four-day work week to publicly naming names, has shaped his leadership philosophy. Sam and Shaan debrief after he leaves, debating how much of his case is true and why they’re both firmly team Ryan anyway.
Speakers: Ryan King (founder of Bolt, executive chairman), Shaan Puri (host), Sam Parr (host)
Introduction and Chicken Wings Debate [00:00:00]
Shaan: Don’t chickens have two wings — but it’s not their actual wing?
Ryan: Hey, what’s up?
Ryan: What’s up, Shaan? Sam?
Sam: What is it, dude? You can settle this for us. So, Sam, this is Ryan — he’s the founder of Bolt. 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?
Sam: I think they’re the — wait, what’s a drumstick? Do you think they’re the actual wings?
Ryan: I feel like they’re not the wings. They’re like — this is such a marketing position.
Sam: Of course they are. Like, what’s a drumstick? Isn’t a drumstick a leg?
Shaan: Ben, look that up so we can see if I’m right. I think I’m right.
Sam: We should switch gears.
Shaan Introduces Ryan [00:00:45]
Shaan: Okay, so Ryan’s here. I met Ryan — where were we hanging out? LA?
Ryan: Yeah.
Shaan: Okay. I was in LA, at this dinner. Ryan’s across the table from me. Everybody was pretty dressed up because the dinner was at the owner of an NBA team’s house. I see this one guy and I’m like, “Is this a TikTok star?” He’s got earrings, he’s got this tie-dye shirt on — he looked totally different than every other business schmuck at this thing. I was like, “What’s up, man, what do you do?” In my head I was like, this guy is 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 and I was like, “Oh — I know Bolt! That’s amazing.”
We ended up becoming friends, I ended up investing in the company, and 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 that background, and then you currently have some spicy Twitter stuff going on and I want to get your take on that. Welcome to the show. It’s a very casual business show.
Ryan: It’s a pleasure to be on, Shaan. I’ve been looking forward to this and I think we picked the perfect time.
Shaan: Sam, what do you know about Ryan besides what I just told you?
Sam: So I was googling you. I saw your Twitter come out of nowhere about a month and a half ago, and Shaan told me all about Bolt and told me about this dinner. Bolt is a payments company valued at like $11 or $14 billion — it’s a huge company. What I know is that you look incredibly young. On your bio it says you’ve started two or three companies worth about a billion dollars, including some crypto stuff. When I was googling you today, one of the first images that came up — it’s beautiful — you’re tweeting about mobs and mafias. The Forbes headline is “Meet the Stanford Bitcoin Mafia” and it’s a picture of you and three friends. So I know you’ve got your hands in a bunch of stuff.
Ryan, what’s your claim to fame? You don’t have to be humble. Just give people the reason they should be listening. Who is this guy? What have you done?
Ryan’s Claim to Fame [00:02:30]
Ryan: Well, my claim to fame is I think I operate pretty fearlessly. I’ve done a lot of things I’ve been told I shouldn’t be doing. In business, I’ve been told many things would never be possible. We’ve written a framework on culture at conscious.org. People were like, “Who are you to write about culture?” Now I have close to a hundred companies pledging that culture. We’ve done the four-day work week. I think we’re just thinking differently — myself and the whole Bolt team — and I’m very proud of that.
Shaan: So walk us through what Bolt actually is. I’ll oversimplify it, you might cringe a little, but the way we pay for things online — some people shop at Amazon, and Amazon says “one-click checkout, we’ve got your stuff saved.” Then you have Shopify, which has Shopify Pay: “you’ve shopped at a Shopify store before, you can check out that way.” Apple’s got Apple Pay. And what you’ve done is said, “Even though those companies are monstrous, the internet’s a lot bigger than that. There are whole stores that aren’t on Shopify, whole platforms like Pinterest where people find products they love and want to check out.”
As somebody who owns an e-commerce store, I’ve felt this pain many times. You can watch people just drop off at checkout because they don’t want to type in their name, address, credit card, zip code every single time when they’re on their phone. That’s the biggest drop-off in our whole store. And if there was a universal network where your information is saved and you can check out at any store, it makes merchants more money because drop-off is lower, it makes the consumer experience easier, and it has this network effect where the more stores use it, the more shoppers have that account — and every store benefits. Amazon only works on Amazon. Shopify only works on Shopify. The world is a lot bigger than that. How’d I do, out of ten?
Ryan: That was pretty epic. We need to put you in customer calls.
Sam: I’m down.
Being Told It Couldn’t Be Done [00:04:45]
Sam: So you created Bolt, and at the beginning people told you it couldn’t be done. What’s an actual story where somebody said, “Look man, it’s not gonna work”?
Ryan: I have a pretty extreme story. I went to one of the tier-one Silicon Valley firms — a payments legend, big firm, big name. I told them what we were doing and they spent the entire conversation telling me why this couldn’t be done. They actually got mad during the conversation. And then after the conversation, they saw one of the people on our team — we were recruiting top people from another company they were involved with — and they spent three hours trying to convince that person not to join us, to join other portfolio companies instead.
I think everybody coming from the payments space — the OGs — they’ve been in the sausage factory, they see how hard it is. But I think there’s 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 anyway.
Ryan’s Background: Groceries to Stanford to Crypto [00:06:00]
Sam: What were you doing before Bolt?
Ryan: My first job was bagging groceries — I did that for three years. Then I started going online to make money, started some websites, online businesses, ran a web development agency working for a lot of customers. That’s where I learned everything about e-commerce.
Then I was lucky enough to get into Stanford. I started the Stanford Bitcoin group with some friends in early 2013 — many of whom have gone on to do amazing things. I dropped out to focus entirely on crypto. I still believe crypto is going to change everything about payments. But about a year in, mid-2015, I was like, “Wait — why does nobody solve the checkout problem?” If you create a checkout where every user who goes through it enrolls in a shopper account, you could create the most powerful shopper network and payment network on the planet. Once I saw that, I couldn’t unsee it. So I decided to go build it.
Sam: Did you drop out and then knock it out of the park with crypto — like money’s good, you’re set, now you’re going to start things? Did that happen at that young of an age?
Ryan: 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 mean, I had a little bit of crypto, but I didn’t become, you know, truly wealthy.
Sam: So you weren’t rich.
Ryan: No, not at all. I had to make Bolt work. I was couch surfing — I didn’t have enough money to even rent a place to stay. A friend texted me before this podcast and said, “Ask him — he already got really wealthy from bitcoin, is that why he’s so brash now?” You’ve just answered that: it was the opposite. At Bolt, I started at a $40K salary, and for about five years it never went higher than $60K. I was living paycheck to paycheck. I wanted every dollar to go to maximizing Bolt’s outcome. Just recently I’ve sold a very tiny amount of shares to cover some expenses, but up until about a month ago I hadn’t sold a single share in almost eight years.
Eco and the Twitter Controversy [00:08:30]
Sam: You also helped start Eco, right? Your buddy runs it?
Ryan: Yeah. What I can take credit for is helping build an awesome team of founders and inspiring some of the ideas, but they’ve really manifested Eco into what it’s become today. The founders there drove amazing vision. Andy Bromberg is one of the CEOs I have the most respect for on the planet — Henry, Ryan Sacks, Joey Krug have done miracle work.
Sam: Cool. Let’s talk about the Twitter thing. You basically came out and said, “Bolt has become successful, but not without some challenges — and not just the normal business kind. There are challenges from the powers that be.” And in Silicon Valley, you picked a fight with two people that very few people had bad things to say about: Y Combinator and Stripe. Stripe is probably the most beloved startup in Silicon Valley. YC is the most powerful brand — it’s like if you were going to call out a college, you’d pick Harvard or Stanford. And you basically told the story of them being the mafia.
Can you bullet point what your argument was for people who haven’t seen it? This audience isn’t going to have seen it on Twitter.
The Stripe and YC Accusations [00:10:00]
Ryan: So the point is: if you’re starting a company in payments, you’ve likely failed. The only ones that have been successful have been international. We probably should have failed five times over — investors pulling out of term sheets when we were about to run out of money. Bolt almost didn’t exist because of the powers that be.
Sam: You’re kind of being vague. What does “powers that be” mean? Let’s separate things out. There’s fair competition — that’s fine. There’s investors deciding the space is too competitive and Stripe’s probably going to win, so I’m backing away — that’s a perception thing, nobody would say that’s unfair. Tell me about the specifics. What did you feel was unfair, where was there real heavy-handedness?
Ryan: So when we would be pitching investors, they’d get interested, say they want to invest — and then they would talk to somebody at Stripe or someone related to Stripe, and either be told they can’t invest, or somehow the conclusion was they were dissuaded from investing.
Sam: But how do you know that? They might just come back and say they’re not interested.
Ryan: Stripe would always come up somehow in that conversation. Many of them told me directly: “I got a call from Stripe and they told me I can’t invest in you guys.”
Sam: But is that bad? I mean, if they were already an investor in Stripe, there’s a conflict of interest, right?
Ryan: But Stripe has intentionally put every single tier-one firm on their cap table. They even stuffed them with small checks — everybody’s on their cap table. And then they say, “You’re conflicted out. That’s a competitor of ours, you’re our shareholder.” I didn’t even consider us 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, from companies doing subscription payments — and then Stripe went and built their own product in those areas. It’s almost as if they have feelers out: anything tangential, they make sure it doesn’t get off the ground, and then they go build it themselves.
Sam: Is there any side of you that thinks — the way you’re phrasing it sounds unethical, but maybe someone could argue that was just a savvy strategic move? Getting everyone on board and keeping competitors out — isn’t that just fair? Do you see that side of it at all?
Ryan: I’ve never told a single investor “you can’t invest in somebody.” To me, everything is fair competition. If someone wants to invest in a company that’s tangential to me, I tell them go for it. We’ve even invested in tangential companies. Innovation is good. I have a very long-term perspective.
When you’re calling investors and telling them they can’t invest in this company — even investors who aren’t on the Stripe cap table — to me that’s just not how I would do it. And I want the next generation of founders to go into building with their eyes wide open. Because I invested eight years of my life into this business without knowing about the games that go on. The most important thing I’m trying to expose is: if you’re coming to Silicon Valley, you have an idea, you’re quitting your job and putting a lot on the line — get ready for war. There will be people who do not want you to exist, and you’re going to need to be ready to battle that.
Hacker News and the YC Angle [00:13:30]
Sam: One of the things you said is that YC has a huge stake in Stripe, they own Hacker News, and that when posts about Bolt would go up and get traction, somehow through editorial shenanigans they’d disappear or get deranked — while posts about Stripe would be up higher. You posted some examples of that. Was that a suspicion or do you know that’s what happened?
Ryan: Pretty sure that’s what happened. We had one post in particular that I’d written for the YC audience — an unraveling of how we do fraud detection and guarantee it with payments, which was radical and new at the time. It had organically gotten to number one. We had a ton of comments, very active, people very interested. And then a Stripe post — I don’t know if it was posted before ours technically or not — started to rise and ours just started to fall and then disappeared.
There’s also a downvote functionality, so you can have a bunch of your employees or friends go downvote something. Whatever it was, they were able to get us off there pretty quickly.
Sam: The guys who started Stripe — the Collison brothers — I don’t know them, but they seem like good dudes from the outside. Is that a characterization you’d challenge?
Ryan: Yeah, that’s exactly what I’m doing. Good dudes is not what you say publicly — it’s what you do privately.
Shaan: I just think that right now you’re like a loose cannon, and I love it. I find it incredibly refreshing. From the outside, you’ve raised money at a $14 billion valuation, you are the guy right now, and I’m just shocked and think it’s cool that you’ve said this. I’ve never heard that before. Me and Sam both have a bit of a rebellious streak and we’ve told some stories on the pod about not keeping it muzzled — sometimes it works to our benefit, sometimes there’s collateral damage. I’ve gotta ask: news came out that you’re stepping down as CEO of Bolt. Did you get in trouble?
Stepping Up to Executive Chairman [00:16:00]
Ryan: Stepping up to executive chairman.
Shaan: Nice.
Ryan: Yeah, that was actually the truth. But the “stepping up” worked well on Twitter. I promoted Modu because this guy schools me on execution every day of the week. He started off running tech and product and they gave him like sixty percent of the company’s core functions. It’s just not my superpower. My superpower is creativity, vision, culture, landing epic deals. Now I get to spend a hundred percent of my time on that.
Shaan: But the timing is weird, right? A lot of people online are saying Ryan got fired because of what he tweeted.
Ryan: This is the start of our fiscal year — January 31st to February 1st. This was timing we’d planned for a while. And then I had some people saying, “Don’t you think we should wait? People are going to think it’s related to the tweets.” I used to have fear about those types of things. This recent episode has just locked me into my fearlessness even more. I’m like, eff 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: You’re crazy. I like it. I respect it.
I also want to say — I’ve talked before about how to pick a fight. There’s a passage in a book called Rework called “Pick a Fight” — it’s a marketing strategy, a two-page thing — and I literally read it word for word on the pod once. It’s about 37signals picking a fight with Microsoft, or Epic Games picking a fight with Apple. The art of it is: you can’t just make something up, you need an actual reason. You punch up — at whoever holds the power. When you do that you get attention, support, and other stories come out of the woodwork that make you seem even more credible.
I don’t know how many people knew about Bolt before this. Checkout technology is not the most in-your-face consumer product. But a lot more people know about it now. How conscious were you? How strategic was it? Were you thinking, “Yes, I’ll be helping people understand how the game is played, but this will also be good for Bolt”?
The Strategy Behind Going Public [00:18:30]
Ryan: I think doing what you believe to be right will always pan out in the end. I stand by this decision. I think it’s great for Bolt. It shows the world who we are as a company — that we’re going to stand up for what’s right no matter how controversial. That’s literally what our entire product is about: standing up to the big guys. What I wrote to my team when I was doing this was: just because our company is worth billions of dollars, 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. 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 point to too many leaders in this country who are truly fearless, who stand up for what they believe in. I think a lot of leadership is fear-based, and we have to kill that.
Shaan: I’m entirely on board with you. But I’ll steelman the other side — not my stance, but it was my first reaction, and it’s changed. A lot of people who used to be underdogs, like Sam Altman or Garry Tan, they’re not underdogs anymore. They’re the man. And they came out saying this guy is lying, he’s full of it. It’s really hard to take a side because of the he-said-she-said. Even though I totally agree that they are the cool-kid group and it’s always fun to stick it to the cool kid —
Honestly, the things you said they did are not even that bad. If they did it, it’s not the worst thing in the world. If they didn’t do it, nobody can prove it, so it kind of doesn’t matter. I think what you did was point out the overall power dynamic — that was the important thing. And then you got your story out there about who you are, what Bolt stands for, what your point of view is.
And that’s actually what made the tactic brilliant — the accusation doesn’t even have to be a Theranos-level scandal. It got so much play because you’re a good writer, and because everybody is so afraid to say a word against them.
I had one of my most viral tweets when I came out and said Clubhouse is going to fail. At the time, Clubhouse was the darling — every VC was fighting to get into the deal, everyone was on it every night. And I got a bunch of private messages from high-profile people: “Dude, I can’t retweet this because of politics, but I totally agree with you. I don’t believe in this thing at all.” Did you get that DM backchannel support?
Ryan: Hundreds. Exactly. If I had any nervousness beforehand, the outpouring I got afterwards gave me all the conviction in the world this was the right thing to do. Hundreds of founders reached out thanking me, sharing their own stories about encounters they’d had. This stuff is rampant.
Sam: You’re missing what you needed — a movement, something people could rally behind. But why is everyone so afraid?
Ryan: You already said the answer. You’d be significantly more financially successful if you just shut up.
Why Ryan Can Say What Others Won’t [00:22:00]
Sam: Are you already very financially successful? I know it’s on paper. That’s why I was asking about the bitcoin stash. Even in this short interview I’ve heard four or five examples: dropped out of Stanford — that takes guts when you don’t have something else that’s working. Started a payments company to compete in one of the most vicious fields where everyone who’s smart tells you it ain’t gonna work. Fearlessness number one. Gone on a four-day work week because you believe in it. Fearlessness number two. Coming out against YC. So there’s this breadcrumb trail of someone who keeps doing really bold things. When I invest in someone, I look for that trail. I think the next thing is just going to be more of that. That’s pretty cool.
I want to switch gears. You’re an idea guy. When we were driving home from the dinner you were telling me how you got the idea for Bolt, how you got the idea for Eco, and I got the sense you’re an idea guy who’s been fully locked in for eight years on one thing. I want you to pull out that list of other opportunities you see but don’t have the time, energy, or interest to chase. Did you bring any ideas?
Ryan: I brought some.
Sam: Oh, fire them off. We’ll react. Give us the quick pitch.
Idea #1: Investment Bank for Early-Stage Startups [00:24:00]
Ryan: Okay. This is a big one. I think someone needs to start an investment bank for early-stage companies where they help introduce you to a bunch of investors, sanity-check your deck and materials, and blast off a bunch of intros — which is honestly ninety-nine percent of the value that YC has. And YC doesn’t even do personal intros. You’re one of 400 companies. You’re a serial number.
Somebody needs to do this. I personally have probably done this for two hundred companies — half the size of a YC batch — personally. 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 intros if investors are interested. Maybe half an hour to sixty minutes with the founder to make sure their materials are good and give them feedback.
Sam: That’s actually a really good idea. What’s the business model? Do you take a percentage of the raise? Equity? A referral fee from the VCs?
Ryan: You take far less than seven percent — maybe a certain percent of the amount raised, and then a little equity. That’s what I do for earlier stages. I take anywhere from a few percent to high single-digit percent of capital raised, and then a little bit of equity.
Sam: You do this?
Ryan: I do this. How much have you raised for other companies?
Sam: A ton of money. I mean — hundreds of millions? Maybe upward?
Ryan: I don’t always take a percentage of capital raised. If I like a founder I sometimes do it for free. Other times I take a little bit in advisor shares, usually less than a percent, sometimes less than half a percent.
Sam: This is actually a great idea.
Shaan: It really is. Here’s the thing though — I used to run this conference business, and it was fun, but the crappy part was the more successful it got, the worse it got. Would this be like that? Where the bigger it gets, the less valuable your name is because you’re promoting everything?
Ryan: Totally. You have to be picky with who you work with. You can’t work with four hundred companies every quarter. A company could do this, you could start your own firm, you could team up with people, you could do it as an individual. There are many ways to skin this cat.
Shaan: How did you build that reputation as both the guy investors trust and the guy with his finger on the pulse of early-stage companies?
Ryan: The secret I’d share with any investor is: treat founders really well, and they’ll refer other founders. Some do that early on, then they build a brand, and then they develop an ego and forget how that brand was generated in the first place. The firm that holds onto that ethos forever is going to build one of the greatest next-generation firms. I developed a reputation with founders for being somebody they could call about literally anything, that they could trust completely, that had their back. My only wish is I had more time.
Shaan: I like that idea. I’ve said for a while that venture investing is going into a few big categories. There are the big brands — Sequoia, YC, a16z, Benchmark — where their stamp of approval means a lot. Then there are niche specialists: “I know robotics better than anybody, I’m going to see all the robotics companies, and even if they get a Sequoia check, they’ll also want the robotics expert in the deal.” And then there’s basically venture services: can you serve the founder in some way? Helping them raise their next round is a smart way to get yourself into the right companies as long as your filter is good. What else you got?
Idea #2: VC DAOs [00:28:00]
Ryan: I think DAOs are going to change the world. There need to be more VC DAOs — where you invest as a DAO. Why is a VC DAO better than individually investing or starting a traditional fund?
Shaan: Why is a VC DAO better?
Ryan: It relies on the collective intelligence of a group. It’s transparent in how it makes decisions. You can raise capital more publicly, and your actions are on a public record. And frankly, the best reason: if you’re an up-and-coming aspiring investor, 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 the DAO, and that track record will attract more and more capital.
Sam: Have you heard of Orange DAO?
Ryan: No — what is it?
Sam: So Orange DAO is basically what Ryan’s describing, but against his enemy of the month, which is YC. It’s a DAO — for people who don’t know, a decentralized autonomous organization, the crypto version of a fund. What makes this one specific is that only YC alumni can enter and only YC companies can get funded. It started with ten or twenty people. Now there are a thousand YC alumni who provide capital, deal flow, diligence, and filtering. And they fund YC companies. Someone proposes, “I think we should invest in this company,” the DAO votes, it comes back 70% yes, 30% no — let’s invest.
Sam: I actually like YC. I love reading Paul Graham. But when you describe this, Shaan, I understand why I’m also frustrated. The rich get richer. It’s a circle jerk that never ends. Part of it is envy — I’m not in that crowd, so I miss out. And part of it is the David vs. Goliath thing.
Ryan: I can’t stand clubs. I have that same feeling, Sam. Something about it just doesn’t feel right. Even if I was inside one. I’ve had the opportunity to join a lot of these clubs and I won’t do it. And honestly it’s in my self-interest not to do it. I could have gotten the benefits, but look where I am now — I’m free to do what I want, to speak up how I want, and I don’t owe any favors to anybody.
Sam: But are you free though? You’ve got six hundred employees. If something bad happens to Ryan it could negatively impact some of his people.
Ryan: I have accountability to my employees and my shareholders — to make them successful and better off. And I think that’s enough. I don’t have all these other groups I’m accountable to that make it basically impossible to say anything. So I consider myself fairly free.
Ryan’s Background: Miami, Miami [00:31:00]
Sam: Where were you raised?
Ryan: Miami, Florida.
Sam: And what did your parents do?
Ryan: My mom worked a local secretarial job. My dad had a small business. I grew up very middle class, went to a big public high school in Miami — four thousand kids, very diverse environment. I got into breakdancing and stuff like that. So when I came to Stanford and Silicon Valley it was the biggest culture shock ever. Miami and Silicon Valley — they couldn’t be more opposite.
Sam: Not anymore.
Ryan: That’s true.
Idea #3: Decentralization of Everything [00:32:00]
Sam: Did you have any other ideas you wanted to share?
Ryan: So here’s my general theme — and I’ll reference Bolt for a second then talk about it broadly. Everything is getting decentralized. Think about commerce. Amazon was phase one: network effects, economies of scale, data — all on one domain, amazon.com. Phase two is Shopify: all of that power, but on one end-to-end enclosed platform. Bolt is the network effect, the data, and the tech economies of scale in a fully decentralized way — completely unbundled, completely headless, completely tech-stack agnostic. That’s why we’re such a powerful force for commerce. That’s why Modu, our new CEO, centralized commerce to Amazon for eight years and then came to us when he saw it getting decentralized and thinks we have the best approach.
I think every industry is getting decentralized. Purchasing — you’re going to see a tidal wave of platforms that help you purchase from your neighbors, purchase food locally. The consciousness of our society is raising. I think we want to buy things that are good for society, that are sustainable, that are recycled — more than things that are flashy. More people are going to start wearing t-shirts.
Sam: And with this whole Twitter thing — a smart move is “I’m mad at this system and it just so happens I’m working on a solution.” Is that what you’ve got up your sleeve?
Ryan: Just might be.
Sam: So what are you going to do?
Ryan: 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. And I have confidence that better systems will be created — not just by me, but by others who may see this as an opportunity to go build.
Shaan: You realize if I was a hater, I’d say, “Oh, well, he’s talking trash because he’s launching a competitor.” What percentage is genuine and what percentage is strategy?
Ryan: I wouldn’t be doing this if I wasn’t distraught with how they operate. If they were a bastion of positivity and good advice and super pro-founder, I wouldn’t be doing this. But I fundamentally do not think they are.
Ryan’s Inner State During the Storm [00:35:00]
Sam: Are you happy right now, or do you have a nervous energy in the morning? I know sometimes when I do something bold, I’m happy I did it, but then I wake up and I’m getting a lot of hate. When Shaan did the Clubhouse thing — it wasn’t a career maker or breaker, but he was getting a lot of heat. I didn’t ask him at the time but I bet there was some nervous energy. I started looking at my mentions that next 24-48 hours way too much. Twenty million impressions, fifty thousand replies — who’s saying what about me, do I need to defend myself? It was a distraction even for me, and I’m pretty strong-minded about this stuff.
Where’s your energy right now?
Ryan: I’d be lying if I said I don’t care what people think. I obviously do — in fact I’m doing this because I care so much that I want my opinions out there. But I’m dealing with it pretty well. I do yoga and meditate every morning, and I stay pretty calm and grounded. I feel more empowered than ever. I’ve gotten so much love the last few days — ninety-five percent love. And then it’s all the people I expected to blast hate — they came out of the woodwork. Sequoia VC, Paul, Sam, YC. That was actually unexpected. I was surprised at how hostile their messages were. For generally older people, I’d think they’d be wiser.
Sam: What did they say? Are they like, “I’m gonna come after you”? What did they actually say?
Ryan: Paul nitpicked on a tweet of mine about Stripe’s publishing, saying that because I focused on that, I was “manic” or something. And then Sam came out and corrected my spelling — said “Y Combinator is two words, not one.”
Shaan: Oh, most arrogant. That’s middle school stuff.
Ryan: That’s what you do in middle school. They might as well have just said “I know you are but what am I.”
Sam: Yeah, exactly.
Ryan: And the guy from Sequoia basically said it sounds like everybody was against them but their numbers were actually growing fine — started commenting on our metrics. VCs aren’t supposed to comment on metrics. And what he said was wrong. It was an ablated misrepresentation of our metrics. A complete low blow. And everybody who messaged me afterward said, “All those comments validated what you were saying. These are the people you’re putting on your cap table. Imagine when you have a disagreement with them as a founder — imagine how they’d treat you.”
Net-Net Read on Ryan [00:38:30]
Shaan: I actually think this is going to be a net win for you. There’s definitely fear of, “Is anyone going to work with me again?” But being a good-natured loose cannon is typically lovable.
Sam: “Good-natured loose cannon” — I like that name.
Shaan: Because intentions matter. If you’re a loose cannon who just wants to hurt people, that’s one thing. If you’re a loose cannon who genuinely wants to help, that’s another — that’s lovable.
Sam: Are you single? Do you live alone?
Ryan: I have people close to me. And everyone’s super supportive. They’re like, “Dude, you’re doing what everyone else was afraid to do.” And I find that if you’re doing things other people are afraid to do, you’re generally in the right. That’s a marker for me that I’m on the right track.
Sam: Have you read The 48 Laws of Power?
Ryan: I haven’t, but I want to. I heard it’s epic.
Sam: You are doing it. So maybe you should pick it up pretty soon, because you are in the middle of a lot of the strategies the author describes. The author is Robert Greene. He’s also got The 33 Strategies of War, of which you are also doing some.
Ryan: I’ll go pick it up.
What Ryan Reads [00:40:00]
Sam: What have you read that’s made the biggest influence on this whole process?
Ryan: 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, 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 the four-day work week.
And you know — certain monks, the wiser and more ascended they are, the longer their sleeves. People think it’s because they’re more docile. It’s actually because they’re more combative when they see something wrong in the world. I’ve found that the further I’ve gone in healing myself and going inward, the more fearlessness I’ve had externally. This is one manifestation of that.
Shaan: You are so strange. It is awesome. You are so cool.
Sam: I’ve become a fan, Shaan. I understand what you saw in this guy at that dinner.
Shaan: Exactly. How old are you again?
Ryan: Twenty-seven.
Sam: You are the weirdest twenty-seven-year-old I’ve ever met. What a unique perspective. You’re interesting. TBD on whether you win this battle — but you’re definitely going to win some big war. That’s for sure.
Shaan: We’re looking forward to it. Fight the war.
Wrapping Up [00:42:00]
Sam: People should go follow you on Twitter. What’s your handle?
Ryan: It’s @theRyanKing.
Sam: Why is that your name?
Ryan: I think it’s fitting.
Sam: There’s a great meme I saw. You posted the thread about the mob and the YC mafia, and then you posted another thread, and someone replied with this meme of a husband reaching over his sleeping wife: “Honey, wake up — the Bolt guy did another thread.” That was so funny. People should follow you at that handle.
Ryan: My grandparents always used to call me the Ryan King growing up. I was like, it’s a great handle. Let’s go.
Sam: I love it. Thanks for coming on. Good luck with all of it.
Ryan: Thanks guys. Thanks Sam, Shaan. Such a pleasure.
Sam: See ya.
Ryan: See ya.
Sam and Shaan Debrief [00:43:00]
Sam: All right, Ryan just left. What’d you think?
Shaan: That guy is so — let’s separate this out. Do I think he’s right or wrong? I don’t hold it that strongly. But as a person, this guy is a killer. I’m team Ryan, just in life. He’s so unique.
Sam: Yeah. He’s a very unique guy. He’s got a very unique style of speaking. I usually have a bias against people who speak slowly — if they don’t have something super interesting to say right away I find myself tuning out. But when I met Ryan, he was talking really slowly, and he would say one thing that would just grip me. I’d be like, “Wait — what?” And then it’d be another minute, and he’d get me with another one. I was like, how old are you? He’s twenty-six, twenty-seven? I said, “You’re one of the strangest twenty-seven-year-olds I’ve ever met, and it’s awesome.” That was my exact takeaway.
I was leaving the dinner and I was like, “You want to hang more? Where are you going?” He canceled his Uber and hopped in my car and I just drove him around, we talked some more, because I just found him to be a very interesting person.
Shaan: In our text group ahead of this, people were saying, “Oh yeah, he’s probably sold a ton of secondary. He probably made all this money on bitcoin — that’s why he can be a loose cannon, say whatever he wants.” He said that’s not true.
Sam: I don’t think that’s true. I don’t think he’s a liar. But I mean, obviously he’s doing fine, right? Bolt’s a $14 billion company. He knows that’s not going to change — even if things go sideways, his equity is still there. That’s the safety net. But he has a track record of doing things his own way, so I’m not really surprised.
I also think he didn’t say anything that bad. Actually, I think it’s a whole bunch about nothing. He did say one bad thing on the pod though — he said the Stripe brothers are bad people. I said they seemed like good dudes and he goes, “No, I don’t think they’re good dudes.”
Shaan: But I don’t think that’s that bad. You’re allowed to say, “I don’t think these are good people.”
Sam: I think that’s bad, man. “Good” and “bad” are simple words, but to say “I don’t think this person is a good person” — that’s a really strong thing to say.
Shaan: We say stronger than that every episode about people we know half as much about.
Sam: True. I’d say the things he accused them of doing are not even that bad at all. And again, I’m an investor in Bolt, I like Ryan, we’re friends — so I’m not even agreeing with him that they’re that bad. I think what they did, if they did it, is pretty much fair play. But it’s really funny the way people reacted to it, and I think it’s really good for him and good for the brand.
Good on him for using this to build the brand of what he’s doing and put his stake in the ground. I think it actually emphasizes how brilliant the tactic was — it’s not even the most scandalous accusation, but it got so much play. He’s a good writer, and everyone was so afraid to say a word against them.
Shaan: Yeah, that was a good find. I could talk to him for a long time. He’s older than me, but I look up to him. I think when he was on here he was trying to do a good job representing what he stands for — like most people do when they’re on a podcast. But having talked to him in private, he was very similar. He’d say, “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 breeze at a late-night dinner over two drinks.” And he was just like, “I said what I said and I meant it.”
He has a very singular-mindedness about what he believes in, and I think that’s cool to interact with. Most people either don’t believe anything, or when they believe they’ll hedge, or they believe when the lights are on but when the lights are off they’re out applying for jobs at the thing they said was going to fail. There’s a wishy-washiness to a lot of people. He has zero wishy-washiness.
Sam: I’m upset at myself. I judged him way off just by looking at his profile picture. I thought he was this like — because he went to Stanford, dropped out, was in Bitcoin forever, is from Miami — I had a stereotype forming in my head. Like this good-looking strong successful guy for whom life is just a game. And in reality he was incredibly intellectual, very intriguing. I believe him that you can be very wealthy on paper and still not have sold a lot of stock. That’s an interesting perspective.
I thought he was cool. Very different than what I expected. I enjoyed it.
Shaan: Cool. Let us know what you think. If you want us to do more of these or less of these, tweet at us. We take it into consideration. We don’t necessarily listen, but we like to know what you think — and then we may or may not do it.