I dropped out of high school…Now I’m building the SpaceX of airplanes
01:12:23 Share

I look in the mirror and I'm like fat and dumb. And I'm like, if I want to have any chance of doing this, I have to go to the startup CEO equivalent of the gym. At that point, I don't think I could have sold a dollar bill for 50 cents. And I didn't know jack about airplanes. And so I'm like, okay, like I need to become that person. I feel like I can rule the world. I know it'd be what I want to.

So how does a guy who's slaying coupons on the internet become the founder of a supersonic jet company? Which by the way, the one liner of what you're making is a commercial jet that flies 1300 miles an hour versus 500 miles an hour. Right? It takes you from, it would take you from where to where and how much time, like,

Yeah, that's what actually matters, right? It takes you from New York to London in just over three and a half hours, Tokyo to Seattle in four and a half, LA, Sydney about eight and a half. And that's version one. We want to go faster after that. Amazing. So my backstory was I've loved airplanes since I was a kid, but because there was basically no innovation happening in aerospace, it never occurred to me to have a career there. So I sort of fell in love with computers, with the internet. My first job out of school was Amazon.

in 2001. My parents didn't understand it because they were like, hey, we got you a computer science degree. Why do you want to work at a bookstore? But it was an amazing time to be there. After that, I was part of one of the very early mobile app companies. And then I wanted to do my own startup. And so I looked at my resume and said, I know e-commerce and I know mobile, so I should work on mobile e-commerce. And surely there'll be something there. And we built this like

barcode scanning game, which like if you make a list of like the most important thing in the universe, the least important, you have to like dig a deeper hole to find where barcode scanning game goes. And I would get up in the morning working on that thing. And I was just like, I was super depressed. And I would think I'm going to screw this thing up. All the investors are going to lose their money. No one's ever going to hire me again. I was like really afraid of failure. And I'm looking at what we're building and

And it's like, wait a minute, I'm building an app for people who shop in stores and I'm an e-commerce nerd. I don't even like stores. What am I doing? And so when we had a chance to kind of go acquihire the company to Groupon and, you know, investors got a return and, you know, I got a little money and I got to like get out of, you know, I basically got my escape fantasy out of this business that I didn't love. It was a huge win. And I kind of spent my couple of years at Groupon.

reflecting on that and thinking about what I learned. And one thing I knew was, I definitely wanted to found again. I'd started my first company in my parents' basement in high school and the founder bug had bit me, but I hated that waking up in the morning thinking about what am I doing and wishing I'd never started. And I never wanted to do that again. And a thing I knew about myself is

is no matter what I was doing as a founder, I was going to push myself to my personal red line. And that red line is the max I'm capable of, and it's going to feel the same no matter what I'm doing. But what won't feel the same is what I'm doing and how motivated I am by it. And I wanted to pick a startup idea where I would never regret starting no matter how hard the day was.

And so it led me to sort of organize all my ideas by how happy I would be if they worked. And I'd had such a passion for flight. At this point, I'd gotten my pilot's license. You know, that's kind of all I knew about airplanes is how to fly a single engine one for fun. And I never understood why no one had picked up where Concorde had left off. And I felt like, OK, I got to look at that and get it out of my system and then move on to the next thing.

So before we tell that the boom story, what were the other ideas on that brainstorm of making a list of possible things to go do? We asked Palmer lucky this question before he started Andrew and he was talking about how he was going to make like the food version of diet Coke. He's just gonna make like calories. You could just like calories that things that tasted good, but had no calories. And he was working on like synthetic food. He's like, uh, actually, all right, nevermind. I'm gonna make weapons.

Well, his other idea was actually pretty amazing. It was a prison. It was a private prison where you only get paid if the inmate gets out of prison and never comes back. Right. And so it was like, ooh, that's actually a good idea. I like that one. It's like the stuff on the cutting room floor is pretty good, too. Yeah. So it was like three. And then, you know, the third one was Andral. But it was like three, like, pretty epic things.

And by the way, his brainstorming process, he said he had like a house where he created like a padded room where he could just build things that would like explode. And he's like, cool, this is just walls that can take explosions. So I'd love to hear, you know, your process might not be quite as crazy, but what were the other ideas and how did you actually brainstorm them? Well, looking back, I think the alternate ideas I had then are not as good as the alternate ideas I have now.

Uh, like I think I had something that was like a rental car company that would pick you up like an Uber. Um, you know, I still sort of wish that existed, but I, but I don't, you know, but I don't, but I don't think that thing has long legs. Right. I don't think it's actually a good idea, even though the small number of times I want a rental car, I really wish I had that. Um, the, uh, you know, I think the, the other, one of my general premises, uh, especially I've been reflected on the boom story is there are a lot of great unsolved problems, uh,

that are hiding in plain sight that nobody's working on. And I think it's an artifact of the bystander effect. And so for anybody who doesn't know that term, the bystander effect is this effect that like, let's say someone falls over having a heart attack on the street and you're the only one around. You're highly likely to run over, call 911, take care of them, make sure it's okay, be there until the ambulance comes. That's what people do. But if the street's crowded...

Everyone tends to think, I'm sure the people who need to know already know. And it gets ignored. And the paradoxical effect is there can be 100 people and the guy having a heart attack is completely ignored. And I think this plays out in the business world. Like in the Valley, like we tend to get told, if your idea is any good, there are already several other good teams working on it.

And if no one else is working on it, there's probably something wrong with the idea. But if you really play that thinking out, what it means is unique things tend to get left hiding in plain sight. And actually, the more compelling they are, the more likely they are to be ignored because the more everybody assumes that somebody else would already be doing it if it were possible. Like supersonic flight is like this. Supersonic flight would obviously be good. Nobody's doing it. It must be impossible or a bad idea.

And there are other things in that category, like traffic.

I don't think I am unaware of anybody attacking traffic in the right way. And it's a very solvable problem. It could be a trillion dollar company. It's funny because the only other person, the person who comes to mind who I think attacks these problems hidden in play site is Elon. Yeah. I was talking to an investor who knows Elon and he was like, you know, the thing I always admired about Elon was that he just saw the trillion dollar idea on the floor that the rest of us were walking by. Very similar to what you described with the bicycle. He goes-

He goes, any of us, a lot of people who grew up like fascinated with space, the idea of rockets that go to Mars was not a secret. It wasn't something nobody had ever thought of. But we all just sort of were blind to it. We assumed either somebody else must be doing it, NASA must be doing it, or it's too hard, it's too expensive, either can't be done. He's like, we all just ignored it. Right.

Elon also has a sort of bone to pick with traffic. I think he's trying to do it with the Boring Company, which sounds like you might disagree with the approach there. How would you approach the traffic problem? I think Boring Company solves half the problem, but there's another half the problem. And so imagine for a second if grocery stores work like roads do, meaning you pay for them with your taxes. And once you've paid your taxes, you feel you're entitled to use it whenever you want, as much as you want.

So what would happen to grocery stores? There'd always be a line out the door and the shelves would always be empty, right? That's what we've done with roads. We pay for them once with our taxes, and then we feel entitled to use them as much as we want whenever we want. So they're always oversubscribed. What you need for roads is a price system, and you need a dynamic price system. I think there's a technology element of this, which I think is about smart traffic lights.

and the ability to actually do smart routing such that, you know, imagine you open up your phone and you open, you know, the Maps app and you put in your destination. And not only are there sort of different routes and different times, there's basically different times and different prices. And you can have fast and expensive or slow and cheap. And I think what we've seen, New York did like a baby experiment with this. And like, you know, the simplest way where they put like a, you know, $8 or $9 fee to go into Manhattan. Are you familiar with that, Sean? Yeah.

I heard about, I heard they were doing, this was recent, right? It's pretty recent. It was super controversial. I,

I'm here right now. And so basically, I think it's $12. So I think it's between the streets of 60th on down. And it actually shows you the map on Google. So if you type in like, you know, if you're on 70th Street and you got to get somewhere to 50th Street, it would say, here's the threshold. And right when you cross through, boom, your bill, $12. And I'm walking around here downtown right now. It is so much quieter than it ever was. It's so much quieter and there's so much less traffic. Like the other day, like...

The day after it happened, I was downtown, and I remember standing in the middle of the street, and I'm like, where is everyone? Right. It's so much better. So I feel like this would be so effective, but also I would have guessed this is really unpopular to implement. But once it's implemented, maybe people see the benefits of it. Who got that through? That's kind of amazing to me that nobody's talking about this –

really important experiment happening in New York, not some fringe like tier five city. Was that unpopular? Oh, it's hugely controversial. Dude, even Trump was like, you're not going to do this. It was kind of like, dude, you're like the president. You don't really, I don't know why you're getting involved in New York City, but like Trump was like, we're yanking this. The governor got involved in this. Yeah, it's a huge ordeal. That's right. And I think the reason it's struggling is because they kind of solved half the problem, but not the other half. And they also did a very like,

the most coarse grained way you could possibly do it. Meaning they put in place a usage fee, but they didn't rebate the other taxes. And so there's a whole argument that says, hang on, I paid for the roads already. Why are you charging me twice? This is a tax increase. And especially as the world kind of moves to EVs and some roads are paid for with like licensing fees and some roads are paid for with gas taxes. Like now is the perfect time to fix this.

to go to usage-based pricing, but you got to get rid of the other taxes. Otherwise, you've given every populace in the world a good reason to say no to it. And the other sort of mindset, I did think a bit about how you would sell this. I think the go-to-market challenges are way bigger than the product challenges. There's some fun AI things about how you build AI traffic lights and how you optimize a network and don't need a bunch of traffic engineers to do it. It should be fun. I think it's way easier than self-driving, way more impactful. Yeah.

But the I think the go to market matters, you know, because it's like, you know, it's like there'll be this envy element of like, oh, all the rich people are passing me. But I think what you could do is basically rebate money from the people who are paying for fast to the people who want cheap. And so, you know, so think of it as like that asshole Elon cut me off. But every time he does it, he has to pay me.

Right. So I think there's a way to effectively there's like cash flow from the people who want who are willing to pay for the highest access to the roads to the people who actually value the cheapest access to the roads. And then there's a technology layer. There's an operating layer on this. And then, you know, whoever builds the system should get 10 percent off the top for building it and running it.

And that ends up being an enormous business. By the way, if somebody wants to start this, I will be your advisor. I will be your champion. I will help raise money for it. I desperately want someone to build this. So Boom has raised $700 million. You guys are... I think you just had a flight in the past year where you built... One of your engines broke the sound barrier. Huge deal. And so...

You know, we've had a few people like you, but you're like a legend potentially in the making. Take us back. Like, what was the original question in your mind? Like, why isn't there a supersonic flight? What was the actual initial question in the first couple weeks? So it was like, why did Concorde fail and what would you have to do for it not to have failed?

But were you on Wikipedia and you just came across that or you're just a flying fan? Well, I was a flying fan. And then, yeah, you know, I go to Wikipedia and I read stuff. And, you know, the extensively the facts make it obvious. Here's here's a hundred seat airplane with a hundred uncomfortable seats and adjusted for inflation at twenty thousand dollar fare. And you can't fill the seats. You can't make any money.

Okay, that's obvious. The next question was, this turned out to be like the key question. Why was Concorde so expensive? The answer is poor fuel economy. And that kicked off a vicious cycle that led to high fares, that led to the low utilization, the lower utilization, the higher the fares have to be. There's a whole vicious cycle to it.

But the root of it was poor fuel economy. And the next question was, well, how much would you have to beat Concorde's 1960s technology by in order to match the fuel economy of a flatbed and business class? The thought was, well, eventually it'd be great to do this for everybody. But as a starting point, business class is huge. And you don't need the bed if the flight's not long. You can have a better bed than one at home. And so how much did you have to beat Concorde by? And it turned out the answer was like less than 10%.

to match the total economics of a flatbedded business class. And I was like, what? Like head explode emoji? Like, I don't really know anything about airplanes, but can we really not do 10% better than 1960s?

Give people a point of reference. How much did you know about planes and calculating the fuel economy and all of that when you started this idea? Yeah. Aren't you a high school dropout? Yeah, I'm a high school dropout. I did actually graduate from college, but my degree is in computer science. And the closest thing I had to an aviation credential is a pilot's license. But this stuff isn't actually that complicated at this level.

Like the fuel burn data is all in Wikipedia and you can calculate fuel burn per seat mile, which turns out to be like the key metric. And it says, okay, what was Concord's fuel burn per seat mile? What's the fuel burn per seat mile of a flatbed in business class? And again, you can just go pull on seat guru. You can see the map. You can like measure on your screen how much of its business class, how many seats are there, how much floor area is in their whole airplane allocated out.

And then it was like, oh, great, you'd have to do about 10% better than Concorde to match the total economics. If you wanted to match the fuel burn per seat mile, it's a bit more than that. But there are all these other utilization benefits from speed. And then the next question was, well, how much better is Boeing's latest airplane versus the one that came before it? And the answer was something like 20%. I'm like, wait a minute, you can't find 10% over 50 years?

Like, I don't, you know, I don't know anything about the details of the technology at this point, but it seemed, it seemed plausible in the face of it. And so at this point I was like, okay, hang on. You said there's a, there's a fact here that has caught my attention. That's right. I'm going to spend a bunch of sleepless nights questioning this. Yeah. Well, or actually I'm going to spend a lot of,

days trying to get smart on it. And so I was like, this seems plausible in the face of it, but I'm on the far left side of the Dunning-Kruger curve. I don't even know what I don't know. And so I sort of imagined myself, I imagined in the future, it's 2050, I'm retired, I'm sitting on the beach, I'm sipping Mai Tais, I had nothing to do with supersonic flight, but I'm just reading the aviation history books. And what do I think they say? Do they say, you know, we're still flying subsonic? I really hope not.

Hopefully they say we're going supersonic now and they tell the story of how it happened. And how do I think that story goes? Does it go after 150 years of not building a supersonic jet, Boeing finally did?

Like, no, business history never goes like that. Right? Like, big companies don't suddenly get enlightened and build disruptive things. So what's the more plausible history? More plausible history is it was a startup that did it. The startup founder would not have come from the entrenched industry where everybody believed it was impossible. Right?

or a bad idea. They have to be an outsider. And what would that outsider have to look like in order to be successful? They'd have to have built a dream team so that to be really good at attracting great people, they'd have to be able to be a great storyteller. They'd be great at persuasion. They'd have to be technically deep in order to be credible with all the audiences that would matter. And I sort of look in the mirror. I'm like, is that me? I've got the like outside the industry box, but like the rest of it's no.

You're like, what would it take to attract this 10 out of 10 smoke show? They probably need to be good looking. They probably need to have a great personality. They need to be funny. They probably should have really nice teeth. That's me. I can do that. I look in the mirror and I'm fat and dumb. And I'm like, if I want to have any chance of doing this, I have to go to the startup CEO equivalent of the gym.

At that point, I don't think I could have sold a dollar bill for 50 cents. And I didn't know jack about airplanes. And so I'm like, okay, like I need to become that person. My mental model for myself is, you know,

You know, we've probably seen those like how it's made videos with pasta and these like pasta extruders. And there's this like big mound of dough in this gigantic like press that's pushing the dough through this tiny little hole. There's like noodle. It gets extruded out the other side of the hole. I'm like, OK, I'm the dough. There's this hole and I need to like extrude myself into the right shape to actually be able to do this.

And so I went back and I started taking remedial calculus and physics because I hadn't had any since high school. And I didn't know how to get through an aerodynamics textbook without way more math and physics.

And then I read the aerodynamic textbooks. I did the problem sets. And if I couldn't figure them out, I threw them out and I got a different book. And you were not working at this point. Is that right? You had left Groupon. How long was that not working time? And how much money were you able to save up in order to kind of do that? Were you like rich, rich? Or you're like, I got two years where I don't have to have a job. I had one year where I didn't have to have a job. Okay. So you had what, like $250,000? It was a little bit better than that. I sort of, in my mind, I had budgeted.

Um, for like two failed startups before I would have to go get a big company job. I was like, let me give, I've got two shots on goal before I'm working for the man again. You're like, cool. So I'll definitely fail on the plane thing. And then I'll try to do that, that mobile app. And then I'll go give up, give up and go back in a job. That was kind of the thought process. I budgeted like, here's, you know, here's my salary replacement money. And, um, here's, here's the seed money that I would put in the company myself. Um,

And I had enough savings to do that twice before I needed a job. And at the time I was married, I had three young kids, like three under 18 months. Oh, my God. Yeah.

I got to do some math, huh? Some twins? What are you doing here? Twins, yeah. And then would you like kiss your kids goodbye in the morning? And you're like, all right, I got to go read. And you just go into the other room. You just go with them to school. You just go to the library with them. They're lunchbox. It's funny. No, I mean, you say that tongue in cheek. That's kind of how it went. Like, you know, I had an office in the basement and I'd give them hugs and kisses and I'd go downstairs and I'd sit at my desk and I'd read and do problem sets all day.

And you were telling your friends for that year, they're like, what are you working on? And you're like, I'm kind of toying with this idea of launching a commercial jet company. Right. And you could just watch the eyeballs roll back. This was 2014. My wife said, okay, honey, you've got a year to screw around with this. And then I expect you to get a job. Yeah. Um,

And this is like before startups were cool. Like now, if you say you're working on like that, you can just go on Twitter and post about it. And people are like, oh, that's awesome. And 2014, it still was a little bit. Startups were cool then, but not hard tech startups. Like there were no hard tech startups to a first order. Like there was SpaceX and that was it.

That was like the era of like Airbnb for blank, Uber for this. That's right. That's right. Yeah. And the only thing that was out there as a reference point for anything like this was SpaceX. And it was still pretty early. Like SpaceX had gotten to orbit and they were working on the Falcon 9. And I remember thinking like, wow, you know, that guy went from PayPal to Rockets. Rockets, you know, Rockets sound harder than airplanes. So this must be possible. It turns out I think actually airplanes are harder than Rockets.

because you have to have, safety is an issue from day one.

versus rockets, you can blow them up and iterate. And you can't do that to an airplane with a person on board. So, but I didn't, I was, you know, what's that old phrase? Like, I'm not doing this because it was easy, but because I thought it would be easy when I started. Yeah, the best motivational poster of all time. Right? And I didn't actually think it was going to be easy. But, and people often ask me, like, if I knew how hard it was going to be, would I still start? And they assume the answer is no. The answer is definitely yes.

I still would have started even knowing how hard it turned out to be. So how do you describe this way of thinking? Because, you know, you talked about this, the pasta dough and the whole, and you're like, what kind of, what noodle do I need to, I need to shove myself through that hole to make myself the noodle that I want to be. So there's, you have that. And you talked about like, I just imagined I worked backwards from the end. I'm retired. I'm reading a book about the history of flight.

And what does that say? Does it say nobody invented fast planes? No. Does it say that Boeing invented the fast plane after showing no evidence of wanting to do so? No. What do you call this, like...

I guess, do you have a frame or a phrase for that way of thinking? Because I think that's very, sounds simple, but it's very rare. I don't do that. And I want to do more of that. So teach me about that. It's first principles thinking. It's super, super important. And it's like the most, I think there are two mental skills that are really valuable. One is first principles thinking. And the other is knowing when you're confused versus when you're clear. And if you have both of those, you can do anything.

Explain both of them. Yeah. So first principles thinking is like looking to get it. Let's take a math analogy here. You know, are there a bunch of data points and I'm going to like draw a line through them and extrapolate? Or am I going to go understand the equation that led to those data points being where they are? Am I pattern matching or am I understanding causality?

And going to causality is really important. And most people don't do it. They operate on rules of thumb. And rules of thumb are fine so long as you're like doing things that have already been done before or not too far from them.

But if you want to do anything new or different or if you want to break from conventional wisdom, you have to understand what's really happening. So for example, the pattern matching is Concorde failed. People weren't willing to pay more for supersonic flight like on Concorde. Therefore, it doesn't work. It was an economic failure. You could find that in a zillion articles on the internet. But like hang on. What was really going on?

What were the actual economics? What's the actual passenger preference? There's a whole, like, don't accept a qualitative answer to a quantitative question here. And so as I was doing this— I saw you say that quote, by the way. I actually think that that quote is kind of more profound than the time that you just gave it. What exactly does that mean? People make all kinds of claims about issues that are measurable without measuring anything. Like, to pull on this example—

supersonic flight costs more. Passengers prefer cheaper flights. You have to solve sonic boom to be able to fly over land in order for the market to be big enough. Therefore, you can't do any of this. And like every single thing in there is some qualitative claim about a thing that's actually measurable. Well, okay, supersonic flight costs more. Well, how much?

What would the fares have to be? How many people are already paying those fares? I mean, like, obviously people pay to save time. Well, how much do they have to pay and how much time is saved? And, you know, OK, is there a market without supersonic flight over land? I don't know. Go get the traffic data, build a freaking database and like start to make some assumptions about costs and time savings and look at how big the market is. That's what I did in 2014. I had a spreadsheet and some JavaScript code that went and did all that.

And it turned out the actual answers were not what anybody claimed they were because nobody else had done the math.

Yeah, it seems like my dad taught me this thing. He goes, he's an Indian dad. He likes to ask for discounts and somebody would say no. And he would ask again. Yeah. And I'd be like, they said no, dad. And he'd be like. Didn't your dad, didn't you say your dad just goes, no, you're going to give me this. Oh yeah. Well, yeah. Sometimes he'll just be like, so we'll get a discount, right? And he'll do that type of thing instead of even asking for the discount. But when he, when somebody says no, he would ask again or he'd ask somebody else. And he would tell me, he would say, don't take no from a person who didn't have the power to say yes in the first place.

Right. That's a great phrase. She couldn't have said yes, so why do I care if she said no? Like she didn't have the authority to give me the discount. So I'm just going to keep asking until I get to the person who at least could say yes. Let's start that. And what you're saying is like don't accept a qualitative answer. Don't take a narrative when numbers would be there. That's right. And I see this all the time in my companies. It's like, yeah, those didn't perform well. Well, how well? How bad was it? How does that compare? Are we sure that – and once you start to dig in, you realize –

People are not operating from a place of fact, and definitely a team is not operating from the same set of facts. But how do you get people, Sean, not to think like that, though? Well, I'll tell you how I do, but I would like to hear maybe Blake do it because it sounds like he's probably a little further ahead on the curve there. Go ahead. I just get very blunt about it, but go ahead. Yeah, I mean, I ask a lot of questions. Like if it's an engineering thing, if someone's telling me something's not possible and they can't explain it in terms of Newtonian mechanics, I just don't believe it.

The other thing is... That was Sean's answer. That was his answer, too. I got a C in physics, by the way. I had to retake it during the summer at Duke. So I'll give you two little tips that have worked for me. And I stole these from when I worked at Twitch. Emmett, the founder of Twitch, and now the CEO, Dan, they both had these great ways of doing this. So both of them, I think...

wanted this. They wanted people to give more substantiated, dug in, detailed answers that were based on fact rather than either opinion or hearsay or just narratives in the company, whatever. And so what they would do is they would say things like, hang on, I just want to make sure I understand this rather than saying, I don't think you understand this, which would make the person feel off text. Hang on, wait, wait, wait. Sorry, I need to ask you this question because I want to make sure I understand this. Yes. You said this

Is that because blah, blah, blah? And so they would break it down that way. They would take them off the defensive. And Dan did this great thing. He would say, oh, you said something interesting there. What he really meant was you said some bullshit. And then he would say, you said that this didn't work. Now explain this to me. It could be that this didn't work because A,

Or it could be that we measured this and we saw this and it could be B. Is it A or B? And then people would have to walk through their logic and they would see where their own logic had potholes, where they were taking huge leaps of assumptions or they'd say, I'd have to go look it up. And then he would either pause and be like, let's see if we can get that data. Do you think you can get that data in the next two minutes? And he'd be like, because if we just continue talking without that data, then I guess the data didn't really matter.

Or he'd say, let's come back with that data. And what I'd be really curious of is A, B, C, D, and E. And it'd be the logic chain that he wants them to go do. And you do that two or three times, you undress people sort of two or three times this way, they start to anticipate it. And they come into the meeting now with that because they know he

He's always going to pause me. I can't just, I can't get away with just saying some bullshit in here. I can't just say it well. It doesn't matter if you say it well. It's what are you actually saying? That's right. So I think that's brilliant. And we built it into our interview process. Like my favorite interview question is teach me something. And it starts a conversation exactly like what you're describing. So hang on. I didn't understand what you said. Why is that? Can you walk me through that?

Like a story about this. At one point I was interviewing for like a head aerodynamicist and like aerodynamics is like the super hard, very mathy, very techie end of aerospace. It's the hardest, technically the hardest part. And this guy shows up and he's got this star-studded resume and he claims to be an expert in hypersonic engine intakes.

And I'm like, teach me something. He's like, oh, like what? I'm like, I don't know. Your resume says you know about hypersonic intakes. Like I barely know what hypersonic is. Teach me. And he launches into this thing and he's like, oh yeah, you really want to use a stream trace design because that minimizes the cowlip angle. And I'm like, hang on, slow down. You went way over my head. What's the cowl? What's the cowlip? What angle are you talking about? And why does any of that matter?

And it turned out the answer was, I don't know. Right. But he had a soundbite that turned out to be true. And we had this whole conversation. And by the end of it, I felt like I had actually been able to reverse engineer some understanding. It was very obvious he didn't have it. And the thing I love about that question is even if you know it, I don't mind sharing this on the podcast because you can't cheat on the question. Even if you know it's coming, you have to actually understand something. You know, what's funny is back when you were getting going in like 14 and 16 and 18, you

I don't know about Sean, but like I was definitely up and coming and I didn't have like a lot of money. I didn't have like enough money to make angel investments. And for some reason, like I got sent your deal, not like, you know, I wasn't in anybody. It was just like, you know, this crazy guy has started this thing. And it was almost as if I'm like, well, if I'm seeing this, then that must mean that all like the cool guys have passed on this. Right. And I remember like reading about this company boom and I'm like,

"Oh, this person's insane. How is anyone taking this seriously?" And obviously that's how a lot of great ideas start.

It didn't seem like you had an easy going when it came to the fundraising if like a guy like me was even able to come across the deck. Oh, it was definitely not easy. But by the way, notice, you know, unpack the thinking there. That's an example of bystander thinking implied to investing. Sure. That's why I'm not – that's why I didn't invest in it. And that's why a bunch of my really smart friends did. Yeah. No, I mean the fundraising piece of this has been extremely difficult. I think some people have said there's no venture in venture capital.

And it's kind of true. And what didn't work for us is going to VCs and trying to raise money. And I think there are a bunch of reasons for that. The superficial reasons are like, oh, the timelines for this are longer. It's not a natural fit for kind of fund life cycles where you want to show a mark quickly and then use that mark to raise the next fund. You know, anybody who's focused on that is going to run from a business like Boom or

But I think the bigger dynamic is like a principal-agent type dynamic. And it took me a long time to realize this because I sort of naively thought VCs are the people with money and their job is to invest it to make more money. But that's actually not what VCs are. VCs are money managers.

Remember that thing that would go around the valley like 10 years ago about Facebook being free and people would say, if the product is free, then you're the product. But by the way, if the product gives you money, then you are definitely the product. Right? And the VCs are in the business of selling startups as an investment class to LPs. And who are the LPs? Many times, if you're lucky, those are wealthy people who have their own money. But many times it's like the endowment fund of Harvard.

And it's like, by the time you trace that dollar back to anybody who actually owns it, you have to go many, many levels back. And, and the dynamics, like the incentive dynamics in that money, in that sort of like chain of money managers is to be able to like raise the next fund and keep going.

at a relatively short time period relative to the investment payoff of most startups. And so what it does is it drives a, there's an incentive to go invest in things that look to LPs like smart investments quickly. And Boom might actually be an amazing investment. I think, you know, there's no guarantee of this. We could totally, you know, at this point we've done enough stuff that impact is guaranteed. You know, I just really don't want it to be a crater, right?

But in success, this is going to be a trillion dollar company because people are going to fly more on flights or supersonic than subsonic. This has to be bigger than Boeing if it works. So it could be a great return, but it will take a long time for it to be clear that it's going to be a great return, which means anybody whose career is based on raising the next fund from their LPs isn't going to like it.

And I wish somebody had been an Oracle and whispered that to my ear in 2014. I could have saved myself an enormous amount of pain. You did end up raising money. And I remember the first time that I heard about you guys, it was, hey, a YC demo day, some guy got on stage and he waved a piece of paper and basically said, we have $100 million or something of LOIs or pre-orders for our supersonic airplanes that we're going to build from, I think, Virgin and one other company. Yeah, it was actually 5 billion in LOIs.

Five billion. It was five billion dollars. I still remember Sam Altman's tweet. He's like, boom, had five billion dollars at LOIs at Demo Day as a record that probably won't be passed soon. Well, exactly. So how the hell does that happen? Is that bullshit? Yeah. No. I mean, so I'll tell you the story, and it involves a story about bullshit. So we do YC, and Sam had been in our seed round.

And he had sort of like, you know, this is back when Sam was running YC. And he had sort of like been telling me I need to do YC. And I'm like, well, isn't YC for like mobile social? You know, I don't know that it's for supersonic jets. They kept saying you have to do it. You have to do it. And eventually I was like, OK, my biggest risk is I never raised enough money to actually build anything. YC claims that they'll help with that.

I'd rather try it and it wasn't useful than not try it and fail and not having given it every chance to succeed. So I did YC. And early on, the group partner's like, well, you need to show up with demo day with sales. And I'm like, this is like a 10-person company that just moved out of my basement.

Like I'd be lucky to, my customer pipeline is like Lufthansa, United. I'd be lucky to sell airplanes in eight years, let alone eight weeks. And what am I going to do? And so it's like, okay, there are two things that are possibilities here. One possibility is a startup airline. But if I look at an established airline, the only one that could conceivably do this quickly is Virgin. And only if I get to Richard. And so I went after both of those paths and we actually got a startup airline to do it.

Um, we got them to, uh, there was a startup called Odyssey was going to do an all business class service from New York to London city airport. And I was like, this is great. They're doing the, you know, flying to London city, which is like the little airport in the center of London. That's the best thing you can do short of being supersonic, um,

These guys probably get speed. And so I met with the guy and he was willing to like give me an LOI on like actually a different corporate entity letterhead. And I'm like, woohoo. And now this LOI was for 15 airplanes at $200 million each. So it's a $3 billion LOI. Explain what an LOI means in this context. Because LOIs can range from

Non-binding, hey, sure, sure. I'm interested in taking a look to a binding LOI with hard money. There's a range. That's what I was saying with Bolshevik. When you're talking LOI, what were you talking at this time? So this LOI was a piece of paper. And, you know, he started asking questions about it. It's from a startup airline, which, by the way, hasn't flown any airplanes yet.

Like this, you know, this was a PDF and it wasn't worth the paper it was printed on. This was the equivalent of I have a girlfriend. She just goes to another school. Trust me. It's, you know, basically. And so I'm doing the practice demo day pitches. And like Michael Siebel, bless his heart, that guy's got the – I think one of the brilliant things about PG is he's built a culture at YC where people just tell you what they really think. It's one of the best things about YC.

Um, and so I'm doing practice demo day and, uh, Michael Siebel looks at my slides and my pitch and he's like, Blake, do you have anything that's real? Cause you sound like you're completely full of shit. Um,

And, you know, it was bitter tasting medicine, but it's what I needed. And so I kept working on retooling the pitch to be focused on what hardware we really had at that point in time. And also trying to figure out this customer thing because I knew that LOI was flimsy. And so we've been working on Virgin and there's a whole other set of stories I could tell at length about how I got to Branson. But I did get to Branson. Well, tell us. We like the hustle stories. Give us one.

So Mark Kelly, who is now Senator Mark Kelly, shuttle commander, you know, human extraordinaire in a bunch of ways. Astronaut Mark Kelly. Astronaut Mark Kelly, yes, was on our advisory board. And he hung out with Richard. And I sort of discovered I could ghostwrite emails from Mark Kelly to Richard Branson and he would send them. And so I did.

And this was, so this was like February, March of 2016. So Virgin Galactic is about to roll out their second generation spaceship. Branson's going to be in the Mojave Desert for that event. My chief engineer had actually got invited to go because he was connected to those circles. I hadn't been invited. And so the pitch to Branson from Mark was,

Hey, the boom guys are going to be in Mojave for your spaceship rollout. You should really meet with them while you're there. And he said, okay. And so we got a 15-minute meeting, and it was me and my chief engineer and Richard and Richard's mom. I actually never got invited to the rollout. I had to crash the rollout.

But I managed to talk my way into it. And I had this 15 minutes with Richard and he kind of, you know, he asked us if we want anything to drink. And I said, no, I've already had lots of coffee. And I realized a couple of minutes into the pitch, he's drinking scotch. It's very early in the morning. I love Richard. You failed the cool guy test. Apparently. Maybe the pitch would have gone better if I had more scotch. But at any rate, he's like, guys, this is brilliant. Like, I love what you're doing. This all makes sense.

And then he kind of leans back on his chair and he's like, oh, but I'm already doing Virgin Galactic. And that's a lot. And I don't, I don't know if I've got two of these things in me. And I said, Richard, we're not asking you for money. We're asking if when this works, if you'd like the first few airplanes to be for Virgin, if you want them. Because if you'll raise your hand and say, I want these, the product makes sense. Then I'll go get all the money elsewhere.

And that turned out to be the thing that worked. How did you think to say, instead of saying, you know, invest in us or advise us or whatever, just say, do you want the first ones to say virgin on the tail or do you want them to say Lufthansa? Yeah.

Because the world is a lot cooler place if we write Virgin on it. It was really Virgin versus BA. And if you know anything about the history of Virgin, you know that Richard – Oh, he hates BA. He hates BA, right? What does Richard – Richard cares about PR and he hates BA. And when he tried to buy Concords, which he did, he tried to buy BA's Concords. I mean they were shutting it down and they wouldn't sell it to him because they didn't want to get embarrassed. So what does this look like? Basically, Sean, I don't know if you ever read his book or the listener.

BA and Virgin, British Airlines, they had a battle in the 90s and early 2000s where BA was trying to shut down Virgin. And so he went on this whole campaign. I think he brought like, is this when he brought a tank through London where he rolled over like a fake model plane? Like it was like a whole PR campaign of the little guy Virgin versus the big guy BA.

Oh, it's great. The stories are great. Right. And he very specifically tried to beat B.A. with supersonic and he lost. Right. And so so he wants to do this and he cares about PR and he cares about his brand. And so I'm like, why don't I let you stick it to B.A.?

So it turned out, you know, so then the meeting ends and there's no deal. And I'm sort of like working it through my friends at Virgin Galactic at this point, trying to get something done. At this point, YC, the way YC was structured, demo day was spread across two days. And the company might not exist if we hadn't been on day two.

So what happened that week is – so Wednesday is our demo day, demo day two. Monday we were like launching the company out of stealth mode. And we'd gotten Ashley Vance to write the launch article for Bloomberg. And if you don't know Ashley, he was like Elon's first biographer. We let him and the Bloomberg team come out to Denver and interview me and take all the pictures they wanted to take. And in my head this was brilliant because the story is going to be boom is the SpaceX of airplanes. Yeah.

But I had no self-awareness about how darn early we were. And I let the photographers take a picture of me on a plastic orange chair climbing into a cardboard mock-up of an airplane. And Ashley actually wrote a nice story, but his editor picked the picture and wrote the headline. And the headline said something like, this Colorado company thinks it can build a supersonic jet.

And then there's my like fat ass climbing into a cardboard mock-up. And so that's Monday. I know it's so bad. So bad. And it's, and then it's, then it's a top of hacker news.

And they photoshopped a helmet on your head. It was so awful. The comments were like, what an idiotic company. Don't they know airplanes aren't made out of cardboard? And what idiot runs marketing at that company? Because who would name a supersonic jet company Boom? And it's brutal. And I'm like, we are so screwed. We're going to be the laughingstock at Demo Day.

And so that's Monday. Tuesday, I'm sitting at my desk working on the slides and up pops this email from Virgin that says, we're in for the first 10 airplanes. You can announce it tomorrow. And I like read the email like three times because I'm like, there is, there's like no way, there's like no way this says what I think it says.

So we're like, we're like in San Jose and an Airbnb prepping for demo day. Right. And, uh, and so I'm like, I think, I think I just went from the biggest loser to the biggest winner. And I called up the team at YC and I'm like, I need to relaunch my startup. Um, how do I do this? And so I think I stayed up to midnight that night, redoing press pitches under embargo. We relaunched the morning of demo day, uh, with a $2 billion LOI from Virgin done on an email. Um,

And then we're back at the top of Hacker News again. And the comments are like, my favorite comments were like, one, what genius runs marketing at Boom? The ones you punch, that's how you launch a company. And then there was another one that was like, Monday colon, ha ha, Wednesday colon, oh shit. And by the grace of Richard Branson, we would have died that week.

You seem to have a lot of these stories that are what our buddy George Mack likes to call high agency. So you were a high school dropout, yet you got into college. And I think you high agencied your way into college. As I understand it, you didn't just work at Amazon. I think you like kicked ass at Amazon and you got the job in an interesting way. And I think you kicked ass in an interesting way. This whole idea of like, I didn't take at face value why the Concord failed. And I kind of like taught myself the physics and calculus I needed to like

Diligence the idea initially. It seems like you have a lot of these. What's your favorite version of those stories that you think, you know, it's that I think your meter might be like, you don't have the, what's it called? Like the, um,

like the thing that stops a car from going at a certain speed, like an artificial governor, a governor. Yeah. You removed your governor. And so you're willing to go further than the average person would when it looks like the default answer is no, no, no for you. Yeah. Um, well, I want to understand, I guess a couple of things. One is I want to understand things for myself. Um, and maybe that's the most important thing. Like I don't, um,

Funny side story. As I was going through a divorce and fighting with my ex-wife over custody, and I had to go through this weird psychological exam. And I'm going through these multi-choice questions where they ask you a random thing. I could tell there were questions like, I think the experts are wrong and I know better. And I'm like...

I think they're testing for delusions of grandeur. So I'm not going to answer this one honestly, but that's actually what I think. I think the experts are wrong all the time. Anybody who bothers to think about it can figure out differently. And so I have that premise. But I also, I don't know, I feel like I have a complicated relationship with my own ego. It was a really weird decision for me psychologically to start this company. It's like I look in the mirror and I'm like, totally don't look like the guy to do this.

And it was very bizarre to tell my friends I'm going to go build supersonic jets. It's like I didn't look like the person to do it. I didn't actually believe on the inside I was going to succeed. I just didn't want to not try. And I really struggled with that. And I remember thinking about who my business heroes were. And I thought of a lot, but I especially thought of Bill Gates because Gates had said, I think during the 70s,

that his goal for Microsoft was to put a personal computer in every home and on every desk running Microsoft software. And he said that in the 70s, right? And then he actually went and did it, and then some. And what was it like to be Bill when Bill said that? Like, he didn't have a resume for it either. He could have flamed out. And because he didn't flame out, we know who Bill Gates is, and we have those computers.

But if, you know, so I'm like, okay, there must be a couple categories of entrepreneurs. So the people who like go after these big missions and they succeed and we all know their names because it is Bill and it's Steve. And back in the day, it's Thomas Edison and, you know, the greats of the great, right? And then there's probably like the dark matter of founders and the dark matter of founders are the people who go for big things. You set big goals, but it doesn't work.

And, um, would I rather be in the dark matter of founders or would I rather be in the, like, I didn't try and I just had a job or I started another mobile apps company. And I made the conscious decision that I'd rather be a dark matter founder. That's pretty badass. Basically you were willing to lose. I had to be willing to lose. I mean, another, another turn of phrase here is, um,

Oh, boy. I'll tell this through the story of my daughter. When she turned 10, which is a few years ago now, I took her out to ice cream. And it was one of these like low moments where I didn't know how the company was going to survive. And by the way, we have one of those like every year. Like with like regularity, there's like a life and death crisis every year.

Um, and I, I didn't know, I didn't know how we were going to get through this particular one. And I was feeling pretty down about it. And like, you know, it might, I had the self-talk that was like, man, my daughter for her entire conscious life, all her dad has been doing is saying he's going to build supersonic jets. And, you know, and it could totally, the first prototype might never fly. Um, and you know, what the hell is my identity to my children?

And it's just not really a great question, but I had that question. And I, you know, so she's in the back of the car. We've just had ice cream. And I said, Ada, like, what would you think if I failed at Boom? And I'm going to tear up as I say this. She didn't miss a beat. And she said, I'd be proud of you for trying. And that speaks to me very deeply. And that's the view I try to have for myself. Do things I'd be proud to try. Do things I'd be proud to fail at.

And I've always told the team, like, there's no guarantee of success here. We might fail, but if we fail, we're going to fail honestly. And we're going to fail having given it our all and we're not going to give up. And when the, uh, when, when XB1, which is, that's our prototype airplane, the, you know, the first startup to ever break the sound barrier with that airplane, you know, when it landed earlier this year for the last time, um, and I was standing outside the airplane with the team of 50 people that had built it and flown it, um, and

And I said to the team, the reason we get to be here today is we didn't give up. We got here because we're the team that did not give up. It took a whole lot of not giving up. Other reasonable people would have given up. A bunch of reasonable people did give up. And to get Overture, our airliner flying, that's going to require a lot more not giving up. So pick something you'd be proud to fail at and don't give up.

New York City founders, if you've listened to my first meeting before, you know I've got this company called Hampton. And Hampton is a community for founders and CEOs. A lot of the stories and ideas that I get for this podcast, I actually got it from people who I met in Hampton. We have this big community of 1,000 plus people and it's amazing. But the main part is this eight-person core group that becomes your board of advisors for your life and for your business and it's life-changing.

Now, to the folks in New York City, I'm building an in-real-life core group in New York City. And so if you meet one of the following criteria, your business either does $3 million in revenue, or you've raised $3 million in funding, or you've started and sold a company for at least $10 million, then you are eligible to apply. So go to joinhampton.com and apply. I'm going to be reviewing all of the applications myself. So put that you heard about this on MFM so I know to give you a little extra love. Now, back to the show. ♪

That's a great story. I also think that, you know, I'm not in your industry at all. Sean and I make internet stuff.

And I remember seeing this Elon Musk video where his, or the rocket, I don't remember what it did, but it was some threshold that they had never accomplished before where it got to space, something like that. And you see him looking up and you hear the launch control like freaking out. And he actually, I think he like cries. It looks like he's about to cry. And he's like looking up and he's like, it almost felt like he was even in awe or impressed where he was like,

I can't believe it. It worked. And the whole crew, you know, a thousand employees are just freaking out. And I remember thinking like, you know, I don't want to, something like that seems so challenging, man, I couldn't do it. It took 15 years, 20 years to get there. And then you see that video and you're like,

Wow, that's totally worth it. And I'm a little envious. It's sort of like someone like running a marathon and at the end of the marathon, their family is there and they're freaking out or doing some type of like crazy physical task where it takes decades or years to work towards. And then you have this like moment where it's like,

you know, there's a very beginning and a middle and an end to the journey. And I'm very envious of that. And it's really cool that you had that, you know, recently it happened like six months ago. I forget that you guys like had your first flight. Yeah, it was three. It was like three months ago. It was recent. Yeah. Three months ago. And I remember having, I'm like, I have nothing to do with you, but I had this sense of pride just for you. And I remember seeing Paul Graham, who isn't like a very...

Paul Graham doesn't seem like a very excitable person. And he seemed very excited about this. And I was like, this is amazing. And it almost felt, it felt very patriotic. You know, they had nothing to, I don't know if there was no like patriotic. It's team ambition instead of team America, right? It's, yeah. I think there's a part of all of us that wonders what's the version of me if I did the most ambitious thing, if I did my version of supersonic jets, right? And when I was little, I wasn't a flight enthusiast. I didn't have my pilot's license. I,

Your thing is your thing, but I think everybody has a little version of that in them. There's some version of that in you, the most ambitious thing, the most you thing you could possibly do.

And you'd probably fail and it'd probably be super hard. And you could probably, if you're smart, you have a lot of easier options if you decided to choose. And it could be small even. That's right. Like be a standup comedian or do a show all the way to go to space. It's the biggest ambition rolled into someone's actual frame and their actual values. Like imagine going back to your five-year-old self and saying, let me tell you, I'm gonna tell you what you're gonna get to do. Here it is. And like, what makes that five-year-old self just like tickled pink? Like, wait a minute, I get to do that?

Blake, have you ever read the Pixar rules of storytelling? They have this thing called the 22 rules and the 22 rules, rule number one, the most important rule. This is Pixar. Pixar who, if anybody knows how to move people, they know how to move people emotionally. Rule number one is you admire the character more for trying than for their successes. And so, you know, the,

the hallmark of every Pixar movie is not the happy ending, right? It's how the character approached the obstacles. And this sounds like super, super obvious, but the reality is like, that's also what, you know, moves founders. It's also what inspires people is not the success. Cause yes, it's amazing. That's like Elon story with the rockets landing. Wow. That's so cool. The rockets landing on their synchronized in the middle of the ocean. That is amazing.

But it's like 10 times more amazing when you know that the first three rockets blew up and that he went all in and that, you know, and that nobody was going to do this if he didn't. That's right. He didn't push forward and continue on in the face of like almost certain failure. Right.

So I think that's like one of the most important rules for founders because it's what will inspire your team. It'll inspire, you know, customers. It'll inspire the audience. It'll inspire investors. In the end, you admire how the character tries rather than their success. I think that's right. One of our OG boom people has a metaphor for this that I found really useful. He calls it the emotional piggy bank. And he's like, every time you're struggling with a problem and you push through, you're putting a quarter in the piggy bank.

And when you finally succeed, you get to break open the emotional piggy bank. And the harder it was to get there, the more joyous the victory. And I think he used it. This guy's been at Boom for nine years. He's one of the few early people that stuck it out. Now he runs our engine program. And I think he was using that with himself a lot. But I've tried to broadcast it to the team. I think it's really true. Yeah.

When do you think you guys are going to be mainstream? When are people going to be flying? Because right now you're at this point in the company where it's like, all right, you've raised $700 million, so obviously you're...

Yeah. 11, we'll turn 11 on paper in September. 11 years ago, I was in my basement reading textbooks. Wow.

Wow. So not that long ago. And now when, what's the next chapter of the story? So you got through a bunch of chapters. You got through the crazy guy in his bedroom to, oh, okay, this is kind of interesting to, oh my God, he made a prototype. This is actually, this is actually potentially serious. Now the next chapter, what's that going to be? And when is it going to be, uh, when are we going to read it? One way to look at this is like, you know, progressive overturning of the skeptics, um,

That's not how I see it on the inside, but that's one way to look at it. You know, the skeptics said a startup could never sell airplanes to airlines. Oh, we did. United bought them, made a deposit. American did. Japan Airlines did a pre-order. Okay, that happened. A startup could never build a supersonic jet. Oh, we did that. Okay, the next thing skeptics say is we're never going to succeed at building our own jet engine. Like, there's a whole class of people who are just convinced that only big companies can build jet engines.

And we're going to find out pretty soon who's right. Because at the end of this year, our full-scale jet engine prototype should be running. And then next year, we'll start building the first airplane. And our goal is to roll the first one off the line in 27, fly it in 28, and be ready for passengers in 29. And there's a good chance that it could take longer than that. But those are the goals. And I believe in...

We've got a lot of learnings along the way about how you set goals and how you set schedules, which I can talk about. But my conclusion is that

ambitious schedules result in the fastest actual execution. And so that's, those are our targets. You know, it's a cliche that I say this at the end of the podcast, you know, it gets to the point where someone says something amazing. I go, man, you're, you're the man. And so I've overused that phrase, but I think that of the people who I look up to, or it's almost,

You're potentially going to be an American hero. And I think that we're honored to talk to you. And I hope that you are because it would be really fun to have you win. It would give us all a huge sense of pride to watch you win. And I think the jet thing is cool. But the cooler thing is that you had a crazy vision and it might actually come to fruition.

You know, I appreciate your saying that. It's a weird, and again, I have a weird relationship with my ego on this, but I think back to like my days in college and I was reading my favorite book, which is Atlas Shrugged. And my favorite character in Atlas Shrugged is this guy, Hank Reardon, who is this sort of combination business technology hero who like invented a new kind of metal. And, but I remember crying and thinking like, man, I don't have it to be somebody like him.

And, you know, I always wanted to be, but I didn't think I could be. And along the way, someone told me that the things we admire in other people are actually our own strengths. And at first that made no sense to me. But as I start to pattern match about it, like my own weaknesses are the things that annoy me the most in other people. And my own strengths are the things I admire most in other people. It's very paradoxical, but it seems to actually be true. And so there's this like,

weird thing where I think we could actually become our heroes. Um, and, and my, you know, of all the various random things that were said about me after we broke the sound barrier, the one that spoke to me the most was where someone who I'd never met, never heard of compared me to Hank Reardon. Oh, that's awesome. Yeah. That's amazing. I always say if you spot it, you got it.

both on the good and bad. If something bothers you about some other people, it's because there's a part of you that recognizes that behavior. And same thing, if something inspires you, there's a part of you that identifies with that behavior, right? You are what you admire. And I think that once you realize that,

You start to get actually, you start to pay some attention to what you choose, what you're choosing to admire because you're actually pointing your little compass in that direction. And, you know, then there's just a question of, are you going to remove the governor? Are you going to leave it in and not actually go chase it all the way? I love this. That's the, that's the happy side of it. And then the unhappy side of it is the things that drive me crazy and other people. Holy shit. I need to have a talk with myself because I'm probably doing it too. Right. Yeah.

I like this quote that you have. You said, if every founder worked on the most ambitious thing, they could get their head around. Everyone would be happier and more great things would get built. You know, there's probably going to be somewhere between half a million and a million people who listen to this episode. Like, I guess if you were going to leave here making your case for that, for why founders should work on the most ambitious thing, what's your case? Can't lose. If you win, obviously it's great.

But I think it's a mistake to start from your resume and it's a mistake to start from what you think you can do. Because I think the only way to find out what you can do is to pick the most motivating thing in the world and run at it. Something that's so motivating that the goal matters more than your own insecurities. That you could do that thing where you extrude yourself into the noodle of the right shape. That's the only way you find your limits. Yeah.

By the way, you were really young, and I think I read that you reported directly to Jeff Bezos. I can't let you leave without asking you. Do you have any good Bezos stories? Oh, I've got a bunch. I did not report directly to Bezos. One of the most annoying things that happens as the –

as you go through these journeys, is like little bits of bio get turned into better soundbites. And then I feel embarrassed because like people claim I was an executive at Amazon and I was not. Well, someone was like, oh, he worked at Amazon. Oh, so he worked for Jeff Bezos. Yeah, he worked for Jeff Bezos. Oh, he worked for Jeff Bezos. Right. So did every hourly worker in the warehouse. Now, I did get able to do something that Jeff cared about. So I got to work with him a bit.

Um, but that meant that like I was updating them once a quarter and, you know, and if I screwed up really badly, like Jeff would hand my ass to me. And, and the, by the way, there's no better early career experience than to be like 22 working on something that Jeff happens to care about. And when I screw it up, he tells me. And so I found out later that I was the youngest ever manager at Amazon. I don't think I knew that at the time, but I got to build the, um, uh, the thing I got to do was basically do Amazon's first ad buy from Google.

And this, and build the system that was, I think the first automated ad buying system on the internet. This was before we were buying AdWords before there was an AdWords API with like screen scrapers that were like automatically clicking buttons in the background with Perl scripts. And it was, my experience of it was, it was like standing next to a rocket and then the rocket took off and like my like jacket got caught on the rocket and I kind of was along for the ride. Yeah.

But at some point, this thing was driving 7% of Amazon sales and 7% of Google sales all at the same time. And somehow I just, you know, my experience of it was I was like on the precipice of failing and they were about to fire me and replace me with somebody who actually knew what they were doing. And I was like right at that line and never quite crossed it. But it was a great first step.

Go build something from scratch gig. And I got to learn a lot from that experience. And I got to know Jeff a little bit, but like I didn't work directly for him. I was like, what's he like? What'd you pick up from him?

Oh, I really admire Jeff. The stories they get told about CEOs tend to be the ones about how they lose their cool and yell at people and fire people in elevators and whatnot. And one of my favorite things, and I would watch Jeff lose it from people a couple times, but what I found is he never lost it with me so long as I took accountability.

And I remember the very first time I was presenting to Jeff, we had just launched like the MVP of this thing I was describing. And I'm like telling Jeff how we built it and why. And I'm like nervous AF because I'm like 22 or 23 presenting to like this God. And we get part of the presentation and it's going well. And then he says, well, why didn't you do X? And he's got this idea. And I said, well, we didn't think of that.

And he starts laughing. He starts laughing the big famous Jeff Bezos laugh. And he says, that's a great answer. It's true all the time, but nobody's willing to say it. And so what I found was like,

You know, whenever I just told Jeff the truth and took accountability, like there was another time I was in front of the executive team and the temperature's going up in the room. I was like, why did we do this when this other thing was a higher priority? And everyone's getting progressively more pissed off that we've misprioritized. And I just spoke up and said, that was my call. I got it wrong. I misprioritized. I won't do it again. And the tone in the room was, okay.

And the conversation moved on. And obviously I couldn't do that every single time on every single thing. But Jeff, Jeff rewarded straight shooters. Jeff rewarded accountability. Jeff rewarded knowing, knowing your own business, like the back of your hand. And he was, he was tremendously forgiving for learning on the job. And I have huge respect for it. The other thing is like, I'd go in to talk to him once a quarter and he would like, you know, and I felt like I knew my shit and he would hand me like a novel insight in five minutes on the thing that I did every day.

And I think that goes to like being really smart, but also that first principles thing. As you go to first principles, you could actually get to novel insights. That's exactly what Emmett said. Amazon bought Twitch for like a billion dollars, whatever. So he reported to Jeff. And so he would go, I think twice a year, three times a year, go meet him. And he's did the same thing. He's like, he wants you to know your business. He's like, but then within five minutes of sort of reading the document, he's like,

He's like, without fail, he would give me one thing that I thought was kind of impossible. I think about this business 24-7. And he gives me an idea or an angle or perspective, like a novel perspective or a novel idea that I didn't have. And he's like, that's amazing. That is a, you know, that shows kind of the level that that guy's at. He's super smart and he's very first principles. And if you put those two things together, that's what actually, I think that's what makes my experience and Emmett's experience possible is

And it's the thing that enables other leaders to do the same thing. The thing I try to challenge myself to do is any given like management review or working with a team, I try to ask myself, what's the most important question? And many times what I find is no one's asked the most important question. It's actually not hard to find it and not hard to ask it. That's pretty brilliant. What's it? Could you just give us an example of that? Like a situation where you asked that question and it shifted the convo? I got one from yesterday. That's sort of an example.

I called the Overture leadership team together on a Sunday. My spidey sense was firing that we weren't aligned about development philosophy. And we start talking about when to insource and when to vertically integrate. And, you know, the conversation in the room started, I was like, oh, vertical integrations is a goal. So we'll eventually do all these things. And I tried to get the conversation to like,

No, it's not. What we need is the winning strategy. What we need to decide is when do we want suppliers and when do we want to do things ourselves? What are the principles by which we make those decisions? And then so I went to the whiteboard and the room started trying to answer those questions. How do we know whether we should do something ourselves or outsource it? And I don't think we've completely cracked the nut on that, but we at least brought the team's focus not to what are the answers, but how are the principles by which we make those decisions?

And I think if we pull, I think we'll keep pulling on that thread. And ultimately the answer to that question will be part of our success story as a company because we've understood how to think about it. And we've got the team on a set of principles that will then, if they won't need to make every, bring every supplier decision to me, they'll like, they'll, they'll like look, understand the principles and make great independent decisions. Dude, Blake, you're awesome, man. You're a, you're a very unique founder. Um, met a lot of founders. You're a very unique guy and what you're doing is awesome. I really appreciate you coming on and,

I hope, I hope my keyboard wasn't making too much noise. Cause I kept writing down these little quotables that I thought were pretty, pretty great for me. The best episodes, Blake, the best episodes you'll either, you'll see Sean and I do two things. You'll see us do this. And we like are gazing or the other thing that I, that we do is we just, you see us do this. You see us just lean back and cross our arms and like classes in session. Uh, well,

Well, thank you. I had a lot of fun. Yeah. Where should people follow you or follow the journey? Where do you want to direct people who want to kind of stay in touch here? I'm pretty active on X. So I'm at Bscholl, B-S-C-H-O-L-L. That's probably the best place to follow along. I try to give people like an inside view on what's going on at Boom. And then I mouth off about other random things in the world. Yeah.

All right, man. Well, I look forward to flying everywhere in half the time. Thank you for coming on. Thank you for doing it. And all right, that's it. That's the pod.

Hey, everyone. A quick break. My favorite podcast guest on My First Million is Dharmesh. Dharmesh founded HubSpot. He's a billionaire. He's one of my favorite entrepreneurs on earth. And on one of our podcasts recently, he said the most valuable skill that anyone could have when it comes to making money in business is copywriting. And when I say copywriting, what I mean is writing words that get people to take action.

And I agree, by the way, I learned how to be a copywriter in my 20s. It completely changed my life. I ended up starting and selling a company for tens of millions of dollars. And copywriting was the skill that made all of that happen. And the way that I learned how to copyright is by using a technique called copywork, which is basically taking the best sales letters, and I would write it word for word. And I would make notes as to why each phrase was impactful and effective. And a lot of people have been asking me about copywork. So I decided to make a whole program for it. It's called Copy That. Copy that,

It's only like 120 bucks. And it's a simple, fast, easy way to improve your copywriting. And so if you're interested, you need to check it out. It's called Copy That. You can check it out at copythat.com.