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SPEAKER_06
Hey, welcome to another episode of My First Million, best of the week edition. This is Ben Wilson. This is just some of the best clips from our episodes throughout the week.
If you've already listened to every episode, there's nothing new here, but it's just bringing out some of the best content in case you didn't get to listen to every second of every episode this week. We got a great one for you today. We had some really great guests on this week.
To start off with, we're hearing from Ryan Breslow. Ryan is the founder of a payments company called Bolt. He has been in the news for writing a Twitter thread where he called out Stripe and Y Combinator, and then we had him on the show the day that he resigned as CEO of his company, Bolt.
And here's what he had to say about the whole controversy.
SPEAKER_04
Cool, and so let's talk about this Twitter thing. So 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, and there's the normal business challenges, and then there's the challenges of the powers that be. And in Silicon Valley, there's two very powerful, and in most people's minds, I think you pick to fight with people that very few people have bad things to say about Y Combinator and Stripe, right? Stripe is probably like the most beloved startup in Silicon Valley, respected, beloved, whatever.
And YC is also the most powerful sort of like brand. It's like basically if you were gonna pick on a college, you'd pick on either Stanford or Harvard if you were going for the top. And you basically told the story about them being the mafia, and so I want you to kind of quickly, can you quickly bullet point what your argument was for people who aren't nerding out on Twitter and aren't seeing it, because the audience we have here is not gonna have seen it.
So bullet point that, and then I got some questions for you.
SPEAKER_01
Yeah, so the point is my motivation here was to open people's eyes to what goes down in Silicon Valley, where it's not all sunshine and rainbows. It is very fierce, and there's fierce competition, and there's also games that are played with powerful institutions and groups of people who help each other out. And so if you're starting a company, especially in payments, you've likely failed.
There's, the only ones that have been successful have been internationally. And we probably should have failed five times over with investors pulling out of term sheets when we were about to run out of money. And so we, I'd say Bolt, almost didn't exist because of the powers that be, the powers that be.
And I think there are a lot of other companies that would have existed today if it wasn't for the powers that be. And so now I don't blame these institutions.
SPEAKER_05
But 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-
SPEAKER_04
Well, let's separate out, right? There's fair business games, which is like we're competing against somebody, that's fair, they can compete with us fiercely. There's investors just deciding this space is too competitive or Stripe's gonna win, I'm just gonna back away, right? So a perception thing, that's kind of like, nobody would say that that's unfair. Talk about the specifics of what you felt was unfair or where, you know, some, there was some heavy handedness to it.
SPEAKER_01
Yeah, so when we would be pitching investors, they'd get interested, they'd say they wanna invest, and then they would talk to somebody at Stripe, someone related to Stripe, and either be told they can't invest, or they shouldn't invest, or somehow the conclusion was, they were dissuaded from investing.
SPEAKER_04
But how do you know that that's what happened? Many of them- They might just come to you and say, we're not interested.
SPEAKER_01
Told me, Stripe would always come up, somehow in that conversation. So many of them pulled me directly. I have investors say directly, I got a call by Stripe, and they told me I can't invest in you guys.
SPEAKER_05
Is that bad though? I mean, what if they were already an investor of Stripe? I understand that. I have a conflict of interest.
SPEAKER_01
But Stripe has all the big names in Silicon Valley invested in them. And so they would intentionally put every single tier one firm on their cap table, and they even stuffed them with small checks. They're like, everybody's on their cap table.
SPEAKER_04
Right, and so- And then they say you're conflicted out. That's a competitor of ours, you're our shareholder, don't it?
SPEAKER_01
Right, exactly. And I didn't even consider ourselves a direct competitor at the time, but I think they're very guarded about anything in their periphery. So I've heard the same story from companies doing card issuing.
I've heard the same stories from companies doing subscription payments. And then Stripe would roll out their own product next. So it's almost as if they have these feelers out, anything that's tangential, they make sure that it doesn't get off the ground, and then they go and build it.
SPEAKER_05
And so- Is there any side of you? So the way that you're phrasing it, and I would like to figure out what my opinion is, I don't have an opinion yet, is like, that's unethical. But one maybe could argue and be like, well, that was just a savvy- Strategy. Strategic move to get everyone on board.
And 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.
SPEAKER_01
I've never pulled a single investor, you can't invest in somebody. Right? So to me, like, everything is fair competition. And if someone wants to invest in a company tangential, to me, I tell them, go for it.
We've even invested in tangential. I invested in tangential. I think, you know, innovation is good.
I have a very long-term perspective. So when you're calling them, I say you can't invest in this company. Like, even if they're not on the Stripecap table, it's investors too that are not on the Stripecap table.
To me, that's just not how I would do business. And I also want found the next generation of founders to go into building with their eyes wide open. Because I invested eight years of my life into this business, not knowing about the games that go on.
Right? And so the most important thing I'm exposing here is if you're coming to Silicon Valley, you have an idea, you're quitting your job, putting a lot on the line, like, get ready for war. Like, it's serious. And there will be people who do not want you to exist, and you're going to need to be ready to battle that.
SPEAKER_04
And so one of the things you say is that, which is they basically hurt our ability to fundraise by telling, first, they kind of played good game theory, right? They got every big investor to get a little piece of Stripe, every investor wants a piece of Stripe. And then they said, cool, now you're conflicted out of investing our competitors. OK, some might say that's shady.
I personally, I'm an investor here, right? I'm a fan of yours. I personally would just say, OK, there's nothing unethical about that. You may not like it, but that's competing.
It's like a strategy. It's a hard strategy. OK, fair enough.
In the same way that, like, I don't think it's cool that Mark Zuckerberg just copied stories or whatever. I don't think that's like, you don't get bonus points of respect for me, but I also don't think you did anything illegal or completely crooked, right? That's you copied something that was copyable. OK, fair enough.
The second thing you said is that YC, which has a huge stake in Stripe, control they own Hacker News. And that on Hacker News, people would be posting about Bolt. It would get some play.
It would go up the ranks. But that somehow there's some editorial shenanigans behind the scenes where all of a sudden, the post about Bolt would disappear or get deranked. And then a post about Stripe would be up higher.
And so you posted some examples of that. Now, I think that's the summary of what you said. As that was happening, did you, is that a suspicion? Or you're like, I know that that's what happened?
SPEAKER_01
Pretty sure that's what happened. You know, because we had some posts, one in particular, that I'd written catered to YC audience. It was an unraveling of how we do fraud detection better and guarantee it with your payments, which was radical and new at the time.
It had organically gotten to number one, held there. We had a ton of comments on it, just very active. People were very interested.
You can go read all my comments. And then Stripe's post, I don't know if it was there before. It seems like they said it got posted technically before.
But anyway, after it's got to number one, they're starting to rise, and ours just started to fall and then disappeared. And so I don't know if those editorial, there's also this downvote functionality. And so you can also just have a bunch of your employees going downvote or have a bunch of your friends.
So whatever it is, they're able to get us off of there pretty quickly.
SPEAKER_05
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 that?
SPEAKER_04
Do you know them?
SPEAKER_05
And is that a characterization that you'd challenge?
SPEAKER_01
Yeah, I mean, that's exactly what I'm doing. So they don't meet my standards for good dudes. And so good dudes is not what you say publicly.
It's what you do privately.
SPEAKER_05
Yeah, I just think that right now, you're a loose cannon. And I love it. And I find it incredibly refreshing.
Because from the outside, you've raised money from amazing people at a $14 billion valuation. You are the guy right now. And I think it's cool.
And I'm shocked, but I think it's cool that you've just said that. I think that that's I've never heard that before.
SPEAKER_04
Me and Sam both have definitely like a rebellious streak in us. And we've told some stories on the pod about situations where we're.
SPEAKER_05
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SPEAKER_04
We do kind of like not keep it muzzled.
SPEAKER_06
All right, next up, we have a segment from an interview with Nathan Berry. Nathan is the founder and CEO of ConvertKit, an email marketing platform. He was telling us about billion dollar creators, how to become one, and how to just do a better job of monetizing your audience.
SPEAKER_04
So you basically have these four rules of building a billion dollar audience. So I guess like first, why did you even want to do this? Like kind of like, what got you interested in this? And then let's walk through the four.
SPEAKER_02
Yeah. So the article asks a question, like the whole premise of it. And that is, what is the most profitable place to direct attention? Right? So everything we do, right? We're recording a podcast now.
Whatever you're doing on TikTok, or if you're a movie star, everything else, right? You have attention. And brands want it. They're willing to sponsor, you know, all of this stuff.
And so it's like, OK, you have the opportunity to point that attention somewhere. What's the most profitable way to do that long term? Because you look at people, you know, maybe who are taking sponsorships, right? Five grand to sponsor the newsletter, or 500 bucks for a sponsored Instagram post, or anything like that. And that's actually not that profitable.
And when you dive in, you learn that the most profitable thing to do is to create your own product and to drive that attention to something where you actually build equity long term. So it's like a longer article talking about that. But like the richest movie stars, you know, like, take Jessica Alba, for example, right? She has made a lot of money from movies.
But the bulk of her wealth is from starting a company using, you know, being the spokesperson for her own company. And then my other favorite example would be Ryan Reynolds, who, you know, right? He's doing ads for other people and probably getting paid. A million bucks here, $10 million there, you know, that kind of thing.
And at some point, he goes like, forget that. I'm going to buy my own companies with Mint Mobile and Aviation Gin, and I'm going to be my own spokesperson. So I don't get cash, I get equity.
And so, you know, you just watch this process of people doing it over and over again. And that's actually my hypothesis with ConvertKit, right? Of I have attention on the internet through running a blog and a newsletter and all of that. How do I want to monetize it? Sponsorships, eBooks, membership, a bunch of things? And I'm like, nope, I want to monetize it through ConvertKit, building a SaaS company.
Like that's my version of the billion dollar creator. So that's the whole premise of the article. So you have a couple examples.
SPEAKER_04
So, okay, so rule number one is you have to build more than a personal brand. So what does that mean? You give the example of Jessica Albright, Mark from Primal Kitchen. So what is the nuance here? It's like, it's not just your face, your name.
You need to actually create a brand around, around your lifestyle or your interest is that it?
SPEAKER_05
By the way, Sean, Primal Kitchen is the sugar-free ketchup company that I like. So this guy named Mark, he's like, kind of looks like the 65 year old version of me, but like even more jacked. And he like has a health blog and he starts selling ketchup and he sells that for like $300 million.
SPEAKER_02
Yeah, so I mean, what Mark did with, I mean, his blog was called Mark's Daily Apple. And it was like the leading, you know, like Paleo, kind of health blog in that space. And a blog like that, you know, when he was doing this, 2006, 2010, that kind of thing, you can make a million bucks a year off that blog and he was, right? But you play that forward.
And that's, it's all about him, all about his name, all the, right, his name is in the name of the site. But you can build substantial wealth that way. What he didn't said is he started Primal Kitchen, you know, Kickstarter, this whole brand by saying, like I have the most popular site in the space.
Let me, you know, make these Paleo friendly ketchup, mayonnaise, that kind of thing.
SPEAKER_04
You know how big his audience was? You know, a few years later. He had at the time or...
SPEAKER_05
It wasn't huge, huge.
SPEAKER_02
Like there's no bigger than ours. Yeah, a hundred thousand subscribers.
SPEAKER_04
A hundred thousand was the kind of like audience size to kick off this thing.
SPEAKER_02
Yeah, you gotta remember, audiences were a lot smaller. Like even just 2015, 2012, like that kind of timeframe. But yeah, then he sold it to Kraft for $200 million.
You can't sell a blog to, like a blog doesn't sell for 200 million, you know? Like all of these things. And the crazy thing is he still owns the audience, right? The thing that, that kickstarted this whole product, he still owns, he can sell off the, that whole brand, talking to him at a conference, you know, he's just onto the next thing, figuring out what he wants to do next. He didn't have to sell his name and whole identity with it.
And Kraft is...
SPEAKER_04
Kylie Cosmetics is the world's brother and brother person. The biggest one that people know about because you have tons of attention through Instagram, TikTok, whatever, the TV show, whatever. And instead of just saying, hey, you can pay me, because people will use to say, wow, you have to pay $25,000 for a tweet from Kim Kardashian or that was $25,000, then it went up to like $250,000.
Then $2 million for an Instagram post from, it got up to that range where it was like, the hundreds of thousands or low millions to get like an actual like endorsement post from one of them. And so then, you know, cool, you can make a lot of money doing that, right? You can stack up quarter of a million dollars at a time, but Kylie Cosmetics was a billion dollar brand. So it was like, well, who wants to pay me to promote their products? Well, it's mostly like skincare products or makeup products or for Kim Kardashian.
It's her shapewear, like, you know, like, and Khloe Kardashian, it was like, you know, fashion or whatever. So Khloe launches true American jeans. Kim Kardashian launches, I think it's called, what was it, skims? Skims, is it like the shapewear brand? Sean, Kylie Cosmetics.
Kanye, Yeezy Shoes, right? Lair is like, they all turned to say, whoever is the most willing advertiser, actually you become my competitor. And I'm gonna launch my own brand, my own equity and have my own equity in this thing. And there's a guy in the NBA who gets made fun of for this, which is this guy, Lavar Ball.
I don't know if you guys know this guy, but basically he has three sons, all three wanted to make it to the NBA. And this guy's this like loudmouth guy, they got like a reality show around them because they're sort of like the like, you know, basketball version of the Kardashians. There's three brothers and like a kind of an overbearing parent who is like architecting their business strategy.
And when they were gonna, the guy was gonna get picked second in the draft and Nike offered him a contract and Ditas. And then instead he created big baller brand, you know, Triple B, he created his own shoe line. And like the shoes kind of sucked and like, you know, he didn't have the full business plan and people were making fun of him for like, oh wow, you turned down a guaranteed $10 million from Nike to like launch this thing, $10 million a year or whatever.
And it's like, actually that was the right move. Now maybe his execution was slightly poor, but that was actually the right move. And a lot of these NBA players would have been better served had they done that themselves.
SPEAKER_05
Well, how's it going?
SPEAKER_04
So the shooting is not going good. Basically the guy they had running it like was like kind of stealing from them. So they fired him.
That was like a black mark on it. The second brother never made it to the NBA. That was like a little bit of an issue.
The first brother kind of underperformed his potential at that time. And actually now that it would have worked because the youngest brother, the one who was like the one who's kind of like, he was kind of like a fuck boy a little bit. He was like, had a goal, like a diamond grill, had like a Lambo at 15 and was like, he was kind of off the reservation.
He actually turned out to be the best one. He's actually a star player. And if they had kind of built it properly around him, it probably would have done a lot better.
SPEAKER_05
So Nathan, you'll get a kick out of this. So like three or four weeks ago, we did this thing where we said, we're going to give five Gs to one or two, three people who take our clips, download it, post it on TikTok and get views. There's this kid who did it.
And I don't remember how many views he got, but like our hashtag, I think got 30 million views in like two weeks. And this guy accounted for a lot of them. And multiple of his videos got a thousand, or sorry, a million views.
One video got so big that we drove 35,000 new members to the subreddit fatfire and they complained. And I was like, reached out to this kid. I'm like, who are you? And he replies back with like, Michael at youmichigan.
org, or something like that, or.you or whatever it is. And I'm like, wait, dude, are you in college? And he calls me and I FaceTime with him and he's in his dorm room.
And he's young. He's still in college. He's in his university thing.
And he's really cocky, not in a bad way, but he's like, he's got a hood spa. And he goes, man, I knew I was going to do this. I wanted to prove to you guys that I could do it.
I want you to pay me money to do this now. And I'm going to do this for other people. And we're going to change the media game.
And I'm going to raise money. And I was like, okay, hold on, dude, hear me out. And he goes, I'm going to go raise money for this thing.
Do you want to invest? I go, bro, listen, you do not want to raise money for this. Here's what you should do. You are so talented at this that don't raise money for this, but get it big and start launching other stuff on top of it.
And if you want to raise money, raise money for that stuff and own all. He owns this thing called like, I forget what it's called, Future, but he's got like eight handles now that have like a million something followers. I'm like, no, no, no, don't raise money for this thing, man.
Own that forever. And that's your piggy bank and your audience. Raise money for like this other thing that you want to do and funnel it through there.
But don't sell that thing because I raised a little bit of money for my thing, which was like that. And I don't regret it because I got the outcome that I wanted, but I do regret it because it definitely, you're massively handicapped because of it.
SPEAKER_02
Yeah, well, and that's, I think such a good point because you can have that platform to launch whatever you want in the same way that, you know, Mark Sisson can use his platform to then go launch the next thing, right? He probably has contracts that say he can't compete in the exact same space, but he could do a fitness thing or he could do something else. Like, Connor McGregor is, right? You have the ability at that point.
SPEAKER_04
Let's give you an example. Connor McGregor is doing this really really at the UFC. So like the UFC gets knocked a lot because of, they have like low fighter pay, right? Like the percentage of revenue that they give to their fighters is way lower than other sports.
NBA is 50%, NFL is like 50%. UFC is like kind of 15 or 20%. So the fighters are, you know, they go out there, they get their face beaten in and they're, they'll make $20,000 off that fight or $40,000 or $80,000.
And then they only get to do that two or three times a year. So it's like a pretty brutal sport for low pay. What Connor McGregor did was, instead of selling the attention, trying to try to make money as his kind of like service fee, he created a brand around literally every part of his lifestyle.
Like, all right, this thing's gonna get me famous, but then, okay, what am I famous for? People like my suits at the press conferences. Cool, I'm launching a suit brand. Okay, I'm Irish.
I'm gonna launch an Irish whiskey. Irish whiskey, I think just sold for, I don't know if you know, Samless, 400 or 500 million.
SPEAKER_05
He walked away with 100 from the deal.
SPEAKER_04
Cool, I'm super fit because I'm a UFC fighter. My body's amazing. Here's my P90X program.
It's called McGregor Fast. You can buy my program and subscribe to that and you can get fit with me. Oh, you're getting fit and guess what else do I do? I recover.
Okay, here's a recovery spray that I spray on my leg that's like, you know, like makes my leg recover faster after workouts. And the guy is literally just selling like every piece of his lifestyle as a independent brand. Like, you know, I think at one point he was thinking about launching a sports betting exchange.
It's like, what is the best business, like who's wants to pay me? Oh, DraftKings wants to pay me? Hmm, maybe instead of DraftKings is McGregor Kings now. And I'll launch a competitor.
SPEAKER_05
He just opened a bar called the Blackboard.
SPEAKER_04
I had good success. Whiskey, what else do we do? Irish Stouts, okay, I'm gonna, so he bought a bar. Not that the bar is that good.
It's like a bar in his hometown. I think a bar is not gonna make a ton of money. But then he used that bar as the like, basically the backdrop to film him creating a stout.
And now he's gonna sell a stout as a new like alcoholic beverage brand. And it's kind of amazing. The guy's gonna become a billionaire and fighting is gonna be the lowest part of his income stream is my guess, which is insane.
SPEAKER_05
I bet you, I bet you, Conor McGregor,
SPEAKER_04
I bet you he did. Well, he might make a billion, he might lose a billion.
SPEAKER_06
All right, lastly, we're playing a clip from our interview with Ryan Holiday. You might know Ryan from his social media presence on The Daily Stoic, from his many appearances on the Tim Ferriss show, or from one of his many books, like The Obstacle is the Way, Stillness is the Key, or Trust Me, I'm Lying. Here, Ryan talks about why he works with the traditional book publisher and how he manages to stay a top selling author.
SPEAKER_04
From the outside, you know, I think a lot of entrepreneurs fill this way, it's like, oh, publishing, you know, record labels and book publishers, it's all just middlemen and they're, they take advantage and the authors see so little, you know, blah, blah, blah. And someone like you, you have a lot of business sense. B, you now have a track record.
C, you have an independent audience you can sell to. So there must be some reason that you say, you know, actually people don't get it, that you do want a publisher for these reasons. What is that?
SPEAKER_03
I look at it on a case by case basis. You're just, you're really doing the math. Will the, what they're paying for it, plus the royalty, what are you thinking you will earn, you know, in a short amount of time, or, you know, in a certain amount of time.
So I just do the math on each project. So every time I think about a book, just because I have a publisher, if obviously no one was interested in publishing it, there would be a different story. But I, you know, I conceive of what the book is.
And then I take it out. My publisher has a first look deal at my books. And I see what, you know, what they think, what they're willing to pay.
And then, you know, I have an agent. And so we obviously try to get that number up as high as possible. And then once I have that number, then I think, okay, what would this look like if I did it myself? So what would it cost me to do it myself? What am I likely to sell myself? How much work is that going to be? How much of a distraction is that going to be? And 90% of the time, you know, the math, the math tends to go towards traditional publishing in my experience.
The kids book that I did, the publisher just wasn't, it wasn't in their wheelhouse. They didn't totally get the project. So I did it myself.
It's been great and really fun and artistically fulfilling, but also just an incredible amount of work. I mean, like the coins I sell directly from my store, right? The manufacturer makes them, they drop it off at the warehouse, they get shipped. Fulfilling books through Amazon is like, and then also the thousand independent retailers in the United States, plus every international edition, you know, is extraordinarily logistically difficult.
SPEAKER_05
And I remember you gave this talk one time that was awesome where you showed a chart of the sales of your book versus the normal book. So a normal book, you get a peak, and then it pretty much just kind of goes away, but then for some of the classics, you get a peak, and then it goes down a little bit, but then it kind of quickly comes up to the point the word even like it's pretty steady throughout, like a catcher in the rye or something like that, or even sometimes it'll suck early on and just slowly get better. Your books, if I remember correctly, they popped just like everyone else.
They went down a little bit just like everyone else, but then they like raise and were pretty steady with daily sales. And you're like, that's because I make shit that can last a long time. And this was actually for when you were running Perennial Seller, I think you were like proving this point.
Is that still the case? And considering all of your other businesses, is making books still where you make the majority of your income, or are you just using that because you love it and it happens to make money, and you make the bulk of your money from other shit?
SPEAKER_03
Yeah, it's most nonfiction authors make more money from speaking than from books. That's because speaking can be more lucrative, but it's also because most authors don't sell very many books. So I'm in an unusual space where my books do sell consistently and I have a lot of them.
So I make a good living from that, but probably make more money from stuff other than books than books. Dude, that's crazy.
SPEAKER_05
All in. That you're like the man and yet still it's like the other.
SPEAKER_03
Well, that's another reason to traditionally publish. So like your publisher does not take any percentage of speaking, does not take any film or TV adaptations, does not take any ancillary products, any merchandising, anything like that. So really the book is, it's not a loss leader because people pay for books and books have value to people, but like the ideas in the book, everything else is downstream from whether that takes hold or not.
Does that make sense? So if the book doesn't land, all the other stuff, doesn't really matter, but if the book works, all the other stuff happens and then the success of the book is slightly less significant. I think in publishing, there's the front list and the back list. Front list is anything within one year, like the year of release that's considered a front list title, and then it becomes a back list title after a year.
So most titles stop selling when they leave the back list, when they leave the front list and become on the back list, but almost all of the income in publishing is from the back list.
SPEAKER_03
So for me, it's about, I've tried to create that in my own catalog of titles that sell every year, as opposed to a big book that comes out, gets a lot of attention. Then three, four years later, I have to write another new book because the other one is not relevant.
SPEAKER_05
It's like Michael Buble or Mariah Carey running a Christmas song. You want that Christmas hit. You want that annuity.
SPEAKER_03
Yeah. Yeah. So my book, The Daily Stoic, when my agent was like, we should do a page day about Stoicism. And I was like, I don't know.
And he was like, it will be your best selling book. And I was like, there's no way. That doesn't make any sense.
Every new year. Yes, it will. He's like, it will.
The book sold more copies already this January than last January.
SPEAKER_06
All right, that's it for the week. If you have any comments, you can tweet any one of us. Tweet Sean at SeanVP or Sam at TheSampar or me, Ben, at Ben Wilson Tweets.
SPEAKER_00
Thanks, everyone, and have a great weekend.