Learn. Share. Evolve…

0:00:02 I look in the mirror and I’m like fat and dumb.
0:00:05 And I’m like, if I want to have any chance of doing this, I have to go to the startup
0:00:07 CEO equivalent of the gym.
0:00:10 At that point, I don’t think I could have sold a dollar bill for 50 cents.
0:00:13 And I didn’t know jack about airplanes.
0:00:15 And so I’m like, OK, like I need to become that person.
0:00:18 I feel like I can rule the world.
0:00:20 I know I could be what I want to.
0:00:24 I put my all in it like my days off on the road.
0:00:26 Let’s travel never looking back.
0:00:30 So how does a guy who’s slaying coupons on the Internet become the founder of a supersonic
0:00:31 jet company?
0:00:36 Which, by the way, the one liner of what you’re making is a commercial jet that flies 1300 miles
0:00:38 an hour versus 500 miles an hour.
0:00:39 Right.
0:00:42 It takes you from it would take you from where to where and how much time like just.
0:00:44 Yeah, that’s what actually matters.
0:00:44 Right.
0:00:49 It take you from New York to London and just over three and a half hours, Tokyo to Seattle
0:00:52 and four and a half, L.A., Sydney, about eight and a half.
0:00:53 And that’s version one.
0:00:54 We want to go faster after that.
0:00:55 Amazing.
0:01:00 So my back story was I’ve loved airplanes since I was a kid, but because there was basically
0:01:03 no innovation happening in aerospace, it never occurred to me to have a career there.
0:01:06 You know, so I sort of fell in love with computers, with the Internet.
0:01:10 My first job out of school was Amazon in 2001.
0:01:15 My parents didn’t understand it because that was they were like, hey, we got you a computer
0:01:16 science degree.
0:01:17 Why do you want to work at a bookstore?
0:01:20 But it was an amazing time to be there.
0:01:24 After that, I was part of one of the very early mobile app companies.
0:01:26 And then I wanted to do my own startup.
0:01:31 And so I looked at my resume and said, I know e-commerce and I know mobile, so I should work
0:01:32 on mobile e-commerce.
0:01:34 And surely there’ll be something there.
0:01:40 And we built this like barcode scanning game, which is like if you make a list of like the
0:01:43 most important thing in the universe, the least important, you have to like dig a deeper
0:01:47 hole to find where barcode scanning game goes.
0:01:50 And I would get up in the morning working on that thing.
0:01:52 And I was just like, I was super depressed.
0:01:55 And I would think I’m going to screw this thing up.
0:01:57 All the investors are going to lose their money.
0:01:59 No one’s ever going to hire me again.
0:02:02 I was like really afraid of failure.
0:02:04 And I’m looking at what we’re building.
0:02:08 And it’s like, wait a minute, I’m building an app for people who shop in stores.
0:02:09 And I’m an e-commerce nerd.
0:02:10 I don’t even like stores.
0:02:12 What am I doing?
0:02:17 And so when we had a chance to kind of go acqui-hire the company to Groupon and investors
0:02:23 got a return and I got a little money and I got to like get out of, you know, I basically
0:02:26 got my escape fantasy out of this business that I didn’t love.
0:02:27 It was a huge win.
0:02:32 And I kind of spent my couple of years at Groupon reflecting on that and thinking about
0:02:33 what I learned.
0:02:37 And, you know, one thing I knew was, you know, I definitely wanted to found again.
0:02:40 You know, I’d started my first company in my parents’ basement in high school.
0:02:46 And there’s, you know, the founder bug had bit me, but I hated that waking up in the
0:02:50 morning thinking about, you know, what am I doing and wishing I’d never started.
0:02:53 And I never wanted to do that again.
0:03:00 And a thing I knew about myself is no matter what I was doing as a founder, I was going
0:03:01 to push myself to my personal red line.
0:03:07 And that red line is the maximum I’m capable of, and it’s going to feel the same no matter
0:03:07 what I’m doing.
0:03:12 But what won’t feel the same is what I’m doing and how motivated I am by it.
0:03:19 And I wanted to pick a startup idea where I would never regret starting, no matter how
0:03:19 hard the day was.
0:03:25 And so it led me to sort of organize all my ideas by how happy I would be if they worked.
0:03:27 And I’d had such a passion for flight.
0:03:29 At this point, I’d gotten my pilot’s license.
0:03:33 You know, there’s kind of all I knew about airplanes as to how to fly a single engine one
0:03:33 for fun.
0:03:37 And I never understood why no one had picked up where Concord had left off.
0:03:42 And I felt like, okay, I got to look at that and get it out of my system and then move on
0:03:43 to the next thing.
0:03:50 So before we tell that the boom story, what were the other ideas on that brainstorm of making
0:03:52 a list of possible things to go do?
0:03:55 We asked Palmer Luckey this question before he started Anderil, and he was talking about
0:03:59 how he was going to make like the food version of Diet Coke.
0:04:00 He’s just going to make like calories.
0:04:04 You could just like calories that things that tasted good, but had no calories.
0:04:05 And he was working on like synthetic food.
0:04:07 He’s like, uh, actually, all right, never mind.
0:04:08 I’m gonna make weapons.
0:04:11 Well, his other idea was actually pretty amazing.
0:04:12 It was a prison.
0:04:17 It was a private prison where you only get paid if the inmate gets out of prison and never
0:04:18 comes back.
0:04:19 Right.
0:04:21 And so it was like, Ooh, that’s actually a good idea.
0:04:22 I like that one.
0:04:25 It’s like the stuff on the cutting room floor is pretty good too.
0:04:25 Yeah.
0:04:27 So like, it was like three.
0:04:31 And then, you know, the third one was Anderil, but it was like three, like pretty epic things.
0:04:36 And by the way, his brainstorming process, he said he had like a house where he created
0:04:40 like a padded room where he could just like build things that had like, would like explode.
0:04:40 And he’s like, cool.
0:04:42 This is just walls that can take explosions.
0:04:47 So I’d love to hear, you know, your process might not be quite as crazy, but what were the other
0:04:49 ideas and how did you actually brainstorm them?
0:04:54 Well, the, um, looking back, I think the, the alternate ideas I had then are not as good
0:04:55 as the alternate ideas I have now.
0:05:00 Uh, like, I think I had something that was like a rental car company that would pick you
0:05:00 up like an Uber.
0:05:06 Um, you know, I still sort of wish that existed, but I don’t, you know, but I don’t, but I don’t
0:05:07 think that thing has long legs.
0:05:08 Right.
0:05:11 I don’t think it’s actually a good idea, even though the small number of times I want a rental
0:05:12 car, I really wish I had that.
0:05:19 Um, the, uh, you know, I think the, the other, one of my general premises, uh, especially
0:05:25 I’ve been reflected on the boom story is there are a lot of great unsolved problems that are
0:05:27 hiding in plain sight that nobody’s working on.
0:05:30 And I think it’s, I think it’s an artifact of the bystander effect.
0:05:35 And so if it, for anybody who doesn’t know that term, that the bystander effect is this
0:05:39 effect that like, uh, let’s say someone falls over having a heart attack on the street and
0:05:40 you’re the only one around.
0:05:44 You’re highly likely to run over, call 9-1-1, take care of them, make sure it’s okay.
0:05:45 Be there until the ambulance comes.
0:05:46 That’s what people do.
0:05:52 Uh, but if the street’s crowded, everyone tends to think, I’m sure the people who need
0:05:55 to know already know, and it gets ignored.
0:06:00 And, and the paradoxical effect is there can be a hundred people and the guy having a heart
0:06:01 attack is completely ignored.
0:06:08 And, um, I think this plays out in, in the business world, like in the Valley, like we tend
0:06:13 to get told if your idea is any good, there are already other, several other good teams working
0:06:13 on it.
0:06:17 And, and if there, no one else is working on it, there’s probably something wrong with
0:06:17 the idea.
0:06:22 But if you, if you really play that thinking out, what it, what it means is unique things,
0:06:26 um, tend to get left hiding in plain sight.
0:06:30 And actually the more compelling they are, the more likely they are to be ignored because
0:06:33 the more everybody assumes that somebody else would already be doing it if it were possible.
0:06:35 Like supersonic flight is like this.
0:06:37 Supersonic flight would obviously be good.
0:06:39 Nobody’s doing it.
0:06:42 It must be impossible or a bad idea, you know?
0:06:44 And there are other things in that category, like traffic.
0:06:49 I don’t think I am unaware of anybody attacking traffic in the right way.
0:06:51 And it’s a very solvable problem.
0:06:52 It could be a trillion dollar company.
0:06:56 It’s funny because, uh, the only other person that the person who comes to mind who I think
0:06:59 attacks these problems hidden in place site is Elon.
0:07:00 Yeah.
0:07:03 Um, you know, I was talking to an investor who knows Elon and he was like, you know, the
0:07:09 thing I always admired about Elon was that he, he just saw the trillion dollar idea on
0:07:11 the floor that the rest of us were walking by.
0:07:16 Very similar to what you described with the, he goes, he goes, any of us, a lot of people
0:07:18 who grew up like fascinated with space.
0:07:23 The idea of, of rockets that go to Mars was not a secret.
0:07:27 It wasn’t a, it wasn’t something nobody had ever thought of, but we all just sort of were
0:07:28 blind to it.
0:07:31 We assumed either it must be somebody else must be doing it.
0:07:33 You know, NASA must be doing it or it’s too hard.
0:07:33 It’s too expensive.
0:07:35 Either can’t be done.
0:07:36 He’s like, we all just ignored it.
0:07:41 And, uh, Elon also has a sort of bone to pick with traffic with the, I think he’s doing,
0:07:44 he’s trying to do with the boring company, which sounds like you might disagree with the
0:07:45 approach there.
0:07:48 How would, how would you approach the traffic problem?
0:07:52 I think boring company solves half the problem, but there’s another half the problem.
0:07:58 And, uh, so imagine for a second, if grocery stores work like roads do, meaning you pay for
0:07:59 them with your taxes.
0:08:05 And once you’ve paid your taxes, you feel you’re entitled to use it whenever you want,
0:08:06 as much as you want.
0:08:08 So what would happen to grocery stores?
0:08:14 There’d always be a line out the door and the shelves would always be empty, right?
0:08:16 That’s what we’ve done with roads.
0:08:21 We pay for them once with our taxes, and then we feel entitled to use them as much as we
0:08:22 want, whenever we want.
0:08:24 So they’re always oversubscribed.
0:08:29 What you need for roads is a price system and you need a dynamic price system.
0:08:32 Like I think there’s a, there’s a technology element of this, which I think is about smart
0:08:37 traffic lights, uh, and the ability to actually do smart routing such that, you know, imagine
0:08:42 you open up your phone and you open, you know, the maps app and, uh, you put in your
0:08:46 destination and not, not only are there sort of different routes and different times, there’s
0:08:50 basically different times and different prices and you can have fast and expensive or slow
0:08:50 and cheap.
0:08:55 And I think what we’ve seen, you know, New York did like a baby experiment with this and
0:08:59 like the, you know, the simplest way where they put like a, you know, eight or $9 fee
0:09:00 to go into Manhattan.
0:09:02 Are you, are you familiar with that, Sean?
0:09:05 I heard about, I heard they were doing, this was recent, right?
0:09:06 It’s pretty recent.
0:09:06 It was super controversial.
0:09:08 I’m here right now.
0:09:11 And so basically I think it’s $12.
0:09:17 So I think it’s between the streets of 60th on down and it actually shows you the map on
0:09:18 Google.
0:09:21 So if you type in like, you know, if you’re on 70th street and you got to get somewhere
0:09:22 to 50th street, it would say, here’s the threshold.
0:09:26 And right when you cross through, boom, you’re billed $12.
0:09:28 And I’m walking around here downtown right now.
0:09:31 It is so much quieter than it ever was.
0:09:34 It’s so much quieter and there’s so much less traffic.
0:09:38 Like the other day, like the day after it happened, I was downtown and I remember like standing
0:09:40 in the middle of the street and I’m like, where is everyone?
0:09:41 Right.
0:09:42 Like it’s so much better.
0:09:47 So I feel like this would be so effective, but also I would have guessed this is really
0:09:51 unpopular to implement, but once it’s implemented, maybe people see the benefits of it.
0:09:52 Was that, who got that through?
0:09:56 That’s kind of amazing to me that nobody’s talking about this really important experiment
0:10:00 happening in New York, not some fringe, like tier five city.
0:10:01 Was that unpopular?
0:10:04 Oh, it’s, it’s, it’s, what’s hugely controversial.
0:10:07 It’s even Trump was like, you’re not going to do this.
0:10:09 It was just, it was kind of like, dude, you’re like the president.
0:10:12 You can’t, you don’t really, I don’t know why you’re getting involved in New York city,
0:10:14 but like Trump was like, we’re, we’re yanking this.
0:10:16 The governor got into involved in this.
0:10:16 Yeah.
0:10:17 It’s a huge ordeal.
0:10:18 That’s right.
0:10:21 And I think that, I think the reason it’s struggling is because they, they kind of solved
0:10:23 half the problem, but not the other half.
0:10:27 And they also did a very, like the most coarse grained way you could possibly do it.
0:10:34 Uh, they, they put in place a usage fee, but they didn’t rebate the other taxes.
0:10:38 And so there’s a whole argument that says, hang on, I paid for the roads already.
0:10:39 Why are you charging me twice?
0:10:40 This is a tax increase.
0:10:46 And, uh, especially as the world kind of moves to EVs and some roads are paid for with like
0:10:49 licensing fees and some roads are paid for with gas taxes.
0:10:53 It’s like, now is the perfect time to fix this, to make, you know, to go to, go to usage-based
0:10:55 pricing, but you got to get rid of the other taxes.
0:11:00 Otherwise you’ve given, you know, every populace in the world, a good reason to say no to it.
0:11:03 And the, the other, the other sort of mindset, you know, I did think a bit about how you would
0:11:04 sell this.
0:11:07 I think the go-to-market challenges are way bigger than the, the product challenges.
0:11:12 There’s some fun, like AI things about how you build AI traffic lights and how you optimize
0:11:14 a network and don’t need a bunch of traffic engineers to do it.
0:11:15 It should be fun.
0:11:19 I think it’s way easier, the self-driving way more impactful, but the, uh, I think the
0:11:22 go-to-market matters, you know, cause it’s like, you know, it’s like, there’ll be this
0:11:25 envy element of like, oh, all the rich people are passing me.
0:11:32 But I think what you could do is basically rebate money from the people who are paying for fast
0:11:34 to the people who want cheap.
0:11:40 And so, you know, so think, think, think of it as like that asshole Elon cut me off, but
0:11:41 every time he does it, he has to pay me.
0:11:43 Right.
0:11:49 So, so I, I think there’s a way to, you know, effectively there’s like cashflow from the
0:11:54 people who want, who are willing to pay for the highest access to the roads to the people
0:11:57 who actually value the cheapest access to the roads.
0:12:00 And then there’s a technology layer, there’s an operating layer on this.
0:12:05 And then the, you know, the, the, whoever builds the system should get the 10% off the
0:12:06 top for building it and running it.
0:12:08 And that ends up being an enormous business.
0:12:12 By the way, if somebody wants to start this, I will like be your advisor.
0:12:13 I will be your champion.
0:12:14 I will help raise money for it.
0:12:16 Like I desperately want someone to build this.
0:12:18 So you, so, all right.
0:12:20 So boom has raised $700 million.
0:12:26 You guys are, uh, I think you just had a flight, you know, in the past year where you built one
0:12:28 of your, one of your engines broke the sound very huge deal.
0:12:34 And so, you know, we, we’ve had a few people like you, but you’re like a legend potentially
0:12:35 in the making.
0:12:37 Take, take us, take us back.
0:12:39 Like, what was the original question in your mind?
0:12:41 Like why, what, why isn’t there a supersonic flight?
0:12:45 What was the actual initial question in the first couple of weeks?
0:12:47 So it was like, why did Concord fail?
0:12:49 And what would you have to do for it not to have failed?
0:12:52 But were you on Wikipedia and you just came across that or you’re just a flying fan?
0:12:57 Well, if I was a flying fan and then, yeah, you know, I could go to Wikipedia and I read stuff
0:13:00 and, you know, the extensively it’s okay.
0:13:01 The facts make it obvious.
0:13:07 Here’s, here’s a, um, 100 seat airplane with a hundred uncomfortable seats and adjusted for
0:13:10 inflation at $20,000 fare and you can’t fill the seats.
0:13:11 You can’t make any money.
0:13:12 Okay.
0:13:13 That’s obvious.
0:13:17 So the next, the next question was, this turned out to be like the key question.
0:13:19 Why was Concord so expensive?
0:13:21 The answer is poor fuel economy.
0:13:26 And that kicked off a vicious cycle that led to high fares that led to the low utilization,
0:13:28 the lower utilization, the higher the fares have to be.
0:13:29 There’s a whole vicious cycle to it.
0:13:32 But, uh, but the root of it was, was poor fuel economy.
0:13:37 And the next question was, well, how much would you have to beat Concord’s 1960s technology
0:13:42 by in order to match the fuel economy of a flatbed in business class?
0:13:46 The thought was, well, eventually it’d be great to do this for everybody, but as a starting
0:13:51 point, business class is huge and you don’t need the bed if the flight’s not long.
0:13:53 You can have a better bed, the one at home.
0:13:55 And so how much do you have to beat Concord by?
0:14:01 And it turned out the answer was like less than 10% to, to match the total economics of
0:14:03 a flatbed in business class.
0:14:04 And I was like, what?
0:14:05 Like head explode emoji.
0:14:10 Like, I don’t really know anything about airplanes, but can we really not do 10% better than 1960s?
0:14:13 Give people a point of reference.
0:14:19 How much did you know about planes and calculating the fuel economy and all of that when you started
0:14:19 this idea?
0:14:20 Yeah.
0:14:22 Aren’t you a high school dropout?
0:14:24 Yeah, I’m a high school dropout.
0:14:28 I did actually graduate from college, but my degree is in computer science and the closest
0:14:30 thing I had to an aviation credential is a pilot’s license.
0:14:34 But this is, this stuff isn’t actually that complicated at this level.
0:14:39 Like the fuel burn data is all in Wikipedia and you can calculate fuel burn per seat mile,
0:14:41 which turns out to be like the key metric.
0:14:45 And, and says, okay, what was Concord’s fuel burn per seat mile?
0:14:48 What’s the fuel burn per seat mile of a flatbed in business class?
0:14:52 And again, you can just go pull on seat guru and you can see the map.
0:14:56 You can like measure on your screen, how much of its business class, how many seats are there,
0:14:59 how, how much floor areas in their whole airplane allocated out.
0:15:01 And then, and then it was like, oh, great.
0:15:05 You’d have to, you have to do about 10% better than Concord to match the total economics.
0:15:08 If you wanted to match the fuel burn per seat mile, it’s a bit more than that, but there
0:15:12 are all these other, you know, utilization benefits from speed.
0:15:16 And, and then the next question was, well, how much better is Boeing’s latest airplane
0:15:17 versus the one that came before it?
0:15:20 And the answer was something like 20%.
0:15:21 I’m like, wait a minute.
0:15:24 You can’t find, you can’t find 10% over 50 years.
0:15:29 Like, I don’t, you know, I don’t know anything about the details of the technology at this point,
0:15:32 but it seemed, it seemed plausible in the face of it.
0:15:33 And so at this point I was like, okay, hang on.
0:15:37 You said there’s a, there’s a fact here that, that has caught my attention.
0:15:38 That’s right.
0:15:42 I’m probably, I’m going to spend a bunch of sleepless nights questioning this.
0:15:43 Yeah.
0:15:47 Well, or actually I’m going to spend a lot of days trying to get smart on it.
0:15:51 And so I was like, this, this seems plausible in the face of it, but I’m on the far left
0:15:53 side of the Dunning-Kruger curve.
0:15:54 I don’t even know what I don’t know.
0:16:00 And, and so I, I sort of imagined myself, I imagined in the future, it’s 2050.
0:16:01 I’m like retired.
0:16:03 I’m sitting on the beach.
0:16:03 I’m sipping Mai Tais.
0:16:07 I had nothing to do with supersonic flight, but I’m just reading the aviation history
0:16:07 books.
0:16:08 And what do I think they say?
0:16:12 You know, do they say, you know, we’re still flying subsonic?
0:16:13 I really hope not.
0:16:17 Hopefully they say we’re going supersonic now and they tell the story of how it happened.
0:16:20 And how do, how do I think that story goes?
0:16:24 Does it go after 150 years of not building a supersonic jet, Boeing finally did?
0:16:28 Like no, business history never goes like that, right?
0:16:32 Like this is a big, big companies don’t suddenly get enlightened and build disruptive things.
0:16:36 So what, what, what’s the more plausible history, more plausible history is it was a startup
0:16:42 that did it, the, the startup founder would not have come from the entrenched industry where
0:16:45 everybody believed it was impossible or a bad idea.
0:16:46 They have to be an outsider.
0:16:49 And what would that outsider have to look like in order to be successful?
0:16:51 They, they, they’d have to have built a dream team.
0:16:55 So that to be really good at attracting great people, they’d have to be able to be a great
0:16:56 storyteller.
0:16:57 They’d be great at persuasion.
0:17:01 They’d have to be technically deep in order to be credible with all the audiences that would
0:17:02 matter.
0:17:03 And I sort of look in the mirror.
0:17:04 I’m like, is that me?
0:17:08 I’ve got the, like outside the industry box, but like the rest of it’s no.
0:17:13 Um, and so I’m like, you’re like, what would it take to attract this?
0:17:17 Like 10 out of 10, like the smoke show, like they probably need to be good looking.
0:17:19 They probably need to have a great personality.
0:17:20 They need to be funny.
0:17:22 They probably should have like really nice teeth.
0:17:23 That’s right.
0:17:24 That’s me.
0:17:25 I can do that.
0:17:29 I mean, so I, I, I look at the mirror and I’m like fat and dumb.
0:17:32 And I’m like, if I want to have any chance of doing this, I have to go to the startup
0:17:34 CEO equivalent of the gym.
0:17:38 Cause I don’t, at that point, I don’t think I could have sold a dollar bill for 50 cents.
0:17:41 And I didn’t know Jack about airplanes.
0:17:43 And so I’m like, okay, like I need to become that person.
0:17:48 My mental model for myself is, you know, we’ve probably seen those, like how it’s made videos
0:17:51 with pasta and there’s like pasta extruders.
0:17:56 And there’s this like big mound of dough in this gigantic, like press that’s pushing the
0:17:57 dough through this tiny little hole.
0:18:00 There’s like noodle, it gets extruded out the other side of the hole.
0:18:01 I’m like, okay, I’m the dough.
0:18:06 There’s this hole and I need to like extrude myself into the right shape to actually be able
0:18:07 to do this.
0:18:11 And, and so I went back and I started taking remedial calculus and physics because I hadn’t
0:18:12 had any since high school.
0:18:16 And I, and I didn’t know how to get through an aerodynamics textbook without way more math
0:18:17 and physics.
0:18:20 And then I read the aerodynamics textbooks and I did the problem sets.
0:18:23 And if I couldn’t figure them out, I threw them out and I got a different book and did
0:18:23 those problem sets.
0:18:25 You were not working at this point.
0:18:26 Is that right?
0:18:27 You had left Groupon.
0:18:31 How long was that not working time and how much money were you able to save up in order
0:18:32 to kind of do that?
0:18:35 Were you like rich, rich, or you’re like, I got two years where I don’t have to have
0:18:35 a job.
0:18:37 I had one year where I didn’t have to have a job.
0:18:37 Okay.
0:18:39 So you had what, like $250,000?
0:18:41 It was a little bit better than that.
0:18:47 I had sort of, in my mind, I had budgeted for like two failed startups before I would have
0:18:49 to go get a big company job.
0:18:52 I was like, let me give, I’ve got two shots on goal before I’m working for the man again.
0:18:54 You’re like, cool.
0:18:55 So I’ll definitely fail on the plane thing.
0:18:58 And then I’ll try to do that, that mobile app.
0:19:00 And then I’ll go give up, give up and go back and get a job.
0:19:02 That was kind of the thought process.
0:19:06 And I budgeted like, here’s, you know, here’s my salary replacement money.
0:19:10 And, um, here’s, here’s the, the seed money that I would put in the company myself.
0:19:15 And I had, I had, I had enough savings to do that twice before I needed a job.
0:19:22 And, you know, at the time I was married, I had three young kids, um, like three under
0:19:22 18 months.
0:19:23 Oh my God.
0:19:24 Yeah.
0:19:26 I got to do some math, huh?
0:19:27 Oh, you have some twins?
0:19:27 What are you, what are you doing here?
0:19:28 I had twins, yeah.
0:19:30 Okay.
0:19:33 And then did you, what, would you like kiss your kids goodbye in the morning?
0:19:34 And you’re like, all right, I got to go read.
0:19:36 And you just go, go into the other room.
0:19:38 You just, you just go with them to school.
0:19:40 You just go to the library with them, the lunchbox.
0:19:41 It’s funny.
0:19:42 No, I mean, you, you say that tongue in cheek.
0:19:43 That’s kind of how it went.
0:19:48 Like, you know, I had a, I had a office in the basement and I, I, I’d give them hugs
0:19:52 and kisses and I’d go downstairs and I’d sit at my desk and I, and I’d read and do problem
0:19:53 sets all day.
0:19:58 And you’re, you were telling your friends for that year, they’re like, what are you working
0:19:58 on?
0:20:02 And you’re like, I’m kind of toying with this idea of launching a commercial jet company.
0:20:03 Right.
0:20:05 And you could just watch the eyeballs roll back.
0:20:06 Yeah.
0:20:07 This was 2014.
0:20:11 My, my wife said, okay, honey, you’ve got a year to screw around with this.
0:20:12 And then I expect you to get a job.
0:20:13 Yeah.
0:20:17 Um, by the way, this is like before startups were cool.
0:20:20 Like now, if you say you’re working on like that, you can just go on Twitter and post about
0:20:22 it and people are like, oh, that’s awesome.
0:20:28 And 2014, that it still was a little bit, uh, uh, startups were cool then, but, but not hard
0:20:29 tech startups.
0:20:32 Like there were no, there were no hard tech startups to a first order.
0:20:34 Like there was SpaceX and that was it.
0:20:38 That was like the era of like Airbnb for blank Uber for this.
0:20:39 That’s right.
0:20:40 That’s right.
0:20:40 Yeah.
0:20:43 And like the, the only, the only thing that was out there as a reference point for anything
0:20:44 like this was SpaceX.
0:20:46 And it was still pretty early.
0:20:50 Like SpaceX had gotten to orbit and they were working on the Falcon nine.
0:20:55 And I remember thinking like, wow, you know, that guy went from PayPal to rockets, rockets,
0:20:56 you know, rockets sound harder than airplanes.
0:20:58 So this must be possible.
0:21:03 Uh, it turns out, it turns out I think actually airplanes are harder than rockets, uh, because
0:21:08 of, because of, you have to have, uh, I guess safety is an issue from day one versus
0:21:12 rockets, you can blow them up and iterate and you can’t, you can’t do that to an airplane
0:21:13 with a person on board.
0:21:16 So, but I didn’t, I didn’t, I was, you know, what, what’s that old phrase?
0:21:21 Like, I’m not doing this because it was easy, but because I thought it would be easy when
0:21:21 I started.
0:21:22 Yeah.
0:21:24 The best motivational poster of all time.
0:21:25 Right.
0:21:30 And I didn’t actually think it was going to be easy, but, um, and people, people often ask
0:21:33 me, like, if I knew how hard it was going to be, would I still start?
0:21:34 And they assume the answer is no.
0:21:36 The answer is definitely yes.
0:21:40 Uh, I still would have started even knowing how hard it turned out to be.
0:21:43 So how do you describe this way of thinking?
0:21:47 Because, you know, you, you talked about this, the pasta dough and the whole, and you’re like,
0:21:51 what kind of, what noodle do I need to, I need to shove myself through that hole to make myself
0:21:52 the noodle that I want to be.
0:21:53 Um, it is.
0:21:58 So there’s, you have that and you talked about like, I, I just imagined I worked backwards from
0:21:59 the end.
0:21:59 I’m retired.
0:22:01 I’m reading a book about the history of flight.
0:22:03 And what does that say?
0:22:05 Does it say nobody invented fast planes?
0:22:06 No.
0:22:10 Uh, does it say that Boeing invented the fast plane after showing no evidence of wanting
0:22:10 to do so?
0:22:11 No.
0:22:12 What do you call this?
0:22:17 Like, I guess, like, do you have a frame or a phrase for that way of thinking?
0:22:19 Because I think that’s very, sounds simple, but it’s very rare.
0:22:20 I don’t do that.
0:22:21 And I want to do more of that.
0:22:22 So I’ll teach me about that.
0:22:24 It’s, it’s first principles thinking.
0:22:26 Um, it’s super, super important.
0:22:29 And it’s like the most, I think there are two mental skills that are really valuable.
0:22:31 One is first principles thinking.
0:22:34 And the other is knowing when you’re confused versus when you’re clear.
0:22:37 And if you have, if you have both of those, you can do anything.
0:22:39 Explain both of them.
0:22:39 Yeah.
0:22:44 So, so first principles thinking is like looking to get, um, you know, it, it, let’s take a
0:22:45 math analogy here.
0:22:50 You know, are there a bunch of data points and I’m going to like draw a line through them
0:22:51 and extrapolate?
0:22:56 Or am I going to go understand the equation that led to those data points being where they
0:22:56 are?
0:22:59 Am I pattern matching or am I understanding causality?
0:23:03 And, uh, and going to causality is really important.
0:23:06 And most people don’t do it.
0:23:09 They operate on rules of thumb and rules of thumb are fine.
0:23:13 So long as you’re like doing things that have already been done before or not too far from
0:23:14 them.
0:23:17 Uh, but if you want to do anything new or different, or if you want to break from conventional wisdom,
0:23:19 you have to understand what’s really happening.
0:23:23 You know, you know, so for example, the pattern matching is Concorde failed.
0:23:27 People weren’t willing to pay more for supersonic flight like on Concorde.
0:23:28 Therefore, it doesn’t work.
0:23:29 It was an economic failure.
0:23:31 And you could find that in a zillion articles on the internet.
0:23:34 And, but like, hang on, what was really going on?
0:23:36 What were the actual economics?
0:23:38 What’s the actual passenger preference?
0:23:43 Um, what, you know, what would people, there’s a whole, like, don’t accept a qualitative answer
0:23:44 to a quantitative question here.
0:23:49 And, and, and so along, as I was doing this, I saw you say that quote, by the way, I actually
0:23:53 think that that quote is kind of more profound than the time that you just gave it.
0:23:55 What exactly does that mean?
0:23:59 People make all kinds of claims about issues that are measurable without measuring anything
0:24:08 like it was to pull on this example, people, supersonic flight costs more passengers prefer
0:24:09 cheaper flights.
0:24:15 You have to solve sonic boom to be able to fly over land in order for the market to be
0:24:16 big enough.
0:24:17 Therefore, you can’t do any of this.
0:24:23 And like every single thing in there is some qualitative claim about a thing that’s actually
0:24:24 measurable.
0:24:26 Well, okay, supersonic flight costs more.
0:24:26 Well, how much?
0:24:30 What would the fares have to be?
0:24:32 How many people are already paying those fares?
0:24:34 I mean, like, obviously people it’s paid to save time.
0:24:37 Well, how much do they have to pay and how much time is saved?
0:24:41 And, you know, okay, is there a market without supersonic flight over land?
0:24:41 I don’t know.
0:24:47 Go get the traffic data, build a freaking database and like start to make some assumptions about
0:24:49 costs and time savings and look at how big the market is.
0:24:50 That’s what I did in 2014.
0:24:53 I had a spreadsheet and some JavaScript code that went and did all that.
0:24:58 And it turned out the actual answers were not what anybody claimed they were because nobody
0:24:59 else had done the math.
0:25:02 Yeah, it seems like my dad taught me this thing.
0:25:04 He goes, he’s an Indian dad.
0:25:07 He likes to ask for discounts and somebody would say no and he would ask again.
0:25:08 Yeah.
0:25:10 And I’d be like, they said no, dad.
0:25:11 And he’d be like.
0:25:14 Didn’t your dad, didn’t you say your dad just goes, no, you’re going to give me this.
0:25:15 Well, yeah.
0:25:18 Sometimes he’ll just be like, so we’ll get a discount, right?
0:25:20 And he’ll do that type of thing instead of even asking for the discount.
0:25:23 But when he’s, when somebody says no, he would ask again or he’d ask somebody else.
0:25:27 And he would tell me, he would say, don’t take no from a person who didn’t have the power
0:25:29 to say yes in the first place.
0:25:30 Right.
0:25:31 That’s a great phrase.
0:25:32 She couldn’t have said yes.
0:25:33 So why do I care if she said no?
0:25:36 Like she didn’t have the authority to say, to give me the discount.
0:25:39 So I’m just going to keep asking until I get to the person who at least could say yes.
0:25:40 Let’s start that.
0:25:43 And what you’re saying is like, don’t accept a qualitative answer.
0:25:46 Don’t take a narrative when numbers would be there.
0:25:49 And I see this all the time in my companies.
0:25:51 It’s like, yeah, those didn’t perform well.
0:25:52 Well, how well?
0:25:53 How bad was it?
0:25:54 What is that?
0:25:54 How does that compare?
0:25:59 Are we sure that that, you know, and once you start to dig in, you realize people are
0:26:00 not operating from a place of fact.
0:26:03 And definitely a team is not operating from the same set of facts.
0:26:06 But how do you get people, Sean, not to think like that, though?
0:26:11 Well, I’ll tell you how I do, but I would like to hear maybe Blake do it because it sounds
0:26:13 like he’s probably a little further ahead on the curve there.
0:26:14 Go ahead.
0:26:16 I just get very blunt about it, but go ahead.
0:26:17 Yeah.
0:26:18 I mean, I ask a lot of questions.
0:26:22 Like if it’s a, if it’s an engineering thing, if someone’s telling me something’s not possible
0:26:25 and they can’t explain it in terms of Newtonian mechanics, I just don’t believe it.
0:26:27 The other thing is-
0:26:28 That was Sean’s answers.
0:26:29 That was his answer too.
0:26:33 I got a C in physics, by the way.
0:26:35 I had to retake it during the summer at Duke.
0:26:39 So I’ll give you two little tips that have worked for me.
0:26:41 And I stole these from when I worked at Twitch.
0:26:45 Emmett, the founder of Twitch, and now the CEO, Dan, they both had these great ways of
0:26:46 doing this.
0:26:50 So both of them, I think, wanted this.
0:26:55 They wanted people to give more substantiated, dug in, detailed answers that were based on fact
0:26:59 rather than either opinion or hearsay or just narratives in the company, whatever.
0:27:03 And so what they would do is they would say things like, hang on, I just want to make sure
0:27:04 I understand this.
0:27:08 Rather than saying, I don’t think you understand this, which would make the person feel of text.
0:27:09 Hang on, wait, wait, wait.
0:27:12 Sorry, I need to ask you this question because I want to make sure I understand this.
0:27:12 Yes.
0:27:13 You said this.
0:27:16 Is that because blah, blah, blah.
0:27:17 And so then they would break it down that way.
0:27:19 They would kind of take them off the defensive.
0:27:20 And Dan did this great thing.
0:27:23 He would say, he said, oh, you said something interesting there.
0:27:26 What he really meant was, you said some bullshit.
0:27:30 And then he would say, you said that this didn’t work.
0:27:32 Now, explain this to me.
0:27:38 It could be that this didn’t work because A, or it could be that we measured this and we
0:27:40 saw this and it could be B.
0:27:41 Is it A or B?
0:27:46 And then people would have to walk through their logic and they would see where their own logic
0:27:51 had potholes, where they would take huge leaps of assumptions or they’d say, I’d have to
0:27:55 go look it up and then he would, he would either pause and be like, let’s see if we can get
0:27:56 that data.
0:27:58 Can you think you’d get that data in the next two minutes?
0:28:01 And he would, he’d be like, cause if we just continue talking without that data, then I
0:28:02 guess the data didn’t really matter.
0:28:05 Or he’d say, let’s come back with that, with that data.
0:28:09 And what I’d be really curious of is A, B, C, D, and E.
0:28:12 And it’d be the logic chain that he wants them to go, to go do.
0:28:15 And you do that two or three times, you undress people sort of two or three times this
0:28:19 way, they start to anticipate it and they come into the meeting now with that because
0:28:22 they know he’s always going to pause me.
0:28:25 I can’t just, I can’t get away with just saying some bullshit in here.
0:28:26 I can’t just say it well.
0:28:29 It doesn’t matter if you say it well, it’s what are you actually saying?
0:28:30 That’s right.
0:28:31 So I think that’s brilliant.
0:28:33 And we built it into our interview process.
0:28:37 Like my, my favorite interview question is teach me something.
0:28:41 And it starts a conversation exactly like what you’re describing.
0:28:44 So the hang on, I didn’t understand what you said.
0:28:44 Why is that?
0:28:46 Can you walk me through that?
0:28:52 Like a story about this, at one point I was interviewing for like a head aerodynamicist
0:28:58 and like aerodynamics is like the super hard, very mathy, very techie end of aerospace.
0:29:02 It’s the hardest, you know, technically the hardest part.
0:29:08 And this guy shows up and he’s got this star-studded resume and he, you know, claims to be an expert
0:29:10 in hypersonic engine intakes.
0:29:11 And I’m like, teach me something.
0:29:12 He’s like, oh, like what?
0:29:13 I’m like, I don’t know.
0:29:15 Your resume says, you know, about hypersonic intakes.
0:29:16 Like I barely know what hypersonic is.
0:29:17 Teach me.
0:29:23 And he launches into this thing and he’s like, oh yeah, you really want to use a stream trace
0:29:25 design because that minimizes the cow lip angle.
0:29:28 And I’m like, hang on, slow down.
0:29:29 You went way over my head.
0:29:30 What’s the cow?
0:29:31 What’s the cow lip?
0:29:33 What angle are you talking about?
0:29:34 And why does any of that matter?
0:29:38 And it turned out the answer was, I don’t know, right?
0:29:40 But he had a soundbite that turned out to be true.
0:29:41 And we had this whole conversation.
0:29:46 And by the end of it, I felt like I had actually been able to reverse engineer some understanding.
0:29:47 It was very obvious he didn’t have it.
0:29:51 And the thing I love about that question is, even if you know it’s, I don’t mind sharing
0:29:54 this on podcasts because you can’t cheat on the question.
0:29:58 Even if you know it’s coming, you have to actually understand something.
0:30:04 Well, you know, what’s funny is back when you were getting going in like 14 and 16 and 18,
0:30:09 I don’t know about Sean, but like, I was definitely up and coming and I didn’t have like a lot
0:30:09 of money.
0:30:11 I didn’t have like enough money to make angel investments.
0:30:15 And for some reason, like I got sent your deal.
0:30:17 Not like, you know, I wasn’t in anybody.
0:30:20 It was just like, you know, this crazy guy has started this thing.
0:30:25 And it was almost as if I’m like, well, if I’m seeing this, then that must mean that all
0:30:27 like the cool guys have passed on this.
0:30:28 Right.
0:30:31 And I remember like reading about this company, boom.
0:30:34 And I’m like, oh, this guy, this person’s insane.
0:30:38 Like why, how is this, how has anyone taken this seriously?
0:30:41 And obviously that’s how a lot of great ideas start.
0:30:45 But it didn’t seem like you had an easy going when it came to the fundraising.
0:30:50 If like a guy like me was even able to come across the deck.
0:30:51 Oh, it was definitely not easy.
0:30:54 But by the way, notice, you know, unpack the thinking there.
0:30:57 That’s an example of bystander thinking implied to investing.
0:30:58 Sure.
0:31:00 That’s why I’m not, that’s why I didn’t invest in it.
0:31:02 And that’s why a bunch of my really smart friends did.
0:31:07 Yeah, no, I mean, the, the, the fundraising piece of this has been extremely difficult.
0:31:11 The, you know, I think some people have said there’s no venture in venture capital and it’s,
0:31:12 it’s kind of true.
0:31:16 And what didn’t work for us is going to VCs and trying to raise money.
0:31:19 And, um, I think there are a bunch of reasons for that.
0:31:23 The superficial reasons are like, oh, that the timelines for this are longer.
0:31:28 It doesn’t, it’s not a natural fit for, um, kind of fund life cycles where you want to show
0:31:31 a mark quickly and then use that mark to raise the next fund.
0:31:35 You know, so anybody who’s focused on that is going to run from a, a business like boom,
0:31:40 you know, but, but I think the bigger dynamic is like a principal agent type dynamic.
0:31:46 And it took me a long time to realize this is like, I, I sort of naively thought VCs are
0:31:49 the people with money and their job is to invest it to make more money.
0:31:51 But that’s actually not what VCs are.
0:31:53 VCs are money managers.
0:31:57 You remember that thing that would go around the Valley, like 10 years ago about Facebook
0:31:58 being free.
0:32:02 And people would say, if the product is free, then you’re the product.
0:32:06 But by the way, if the product gives you money, then you are definitely the product.
0:32:08 Right.
0:32:13 And like VCs are in the business of selling startups as an investment class to LPs.
0:32:16 And, but, and who are the LPs?
0:32:20 Many times they’re some, if you’re lucky, those are wealthy people who have their own money.
0:32:23 But many times it’s like the endowment fund of Harvard.
0:32:28 And it’s like, by the, by the time you trace that dollar back to anybody who actually owns
0:32:30 it, you have to go many, many levels back.
0:32:36 And, and the dynamics, like the incentive dynamics in that money, in that sort of like chain of
0:32:43 money managers is to, to be able to like raise the next fund and keep going relative, you
0:32:49 know, at a relatively short time period relative to the investment payoff of, of most startups.
0:32:55 And so what it does is it drives a, there’s an incentive to, to, to, to go invest in things
0:32:57 that look to LPs like smart investments quickly.
0:33:01 And, uh, boom might actually be an amazing investment.
0:33:04 I think, you know, not, there’s no guarantee of this.
0:33:08 We could totally, you know, at this point we’re big, we’ve done enough stuff that impact is
0:33:08 guaranteed.
0:33:13 You know, I just really don’t want it to be a crater, but you know, in, in success, this
0:33:14 is going to be a trillion dollar company.
0:33:17 Cause like people are going to fly more when flights are supersonic than subsonic.
0:33:19 This has to be bigger than Boeing if it works.
0:33:24 So it could be a great return, but it will take a long time for it to be clear that it’s
0:33:25 going to be a great return.
0:33:31 Uh, which means any, anybody whose career is based on raising the next fund from their
0:33:32 LPs, isn’t going to like it.
0:33:37 And I wish somebody had been an Oracle and whispered that to my ear in 2014.
0:33:39 I could have saved myself an enormous amount of pain.
0:33:40 You did end up raising money.
0:33:46 And I remember the first time that I heard about you guys, it was, hey, a YC demo day.
0:33:51 Some guy got on stage and he waved a piece of paper and basically said, we have a hundred
0:33:57 million dollars or something of LOIs or pre-orders for our supersonic airplanes that we’re going
0:34:00 to build from, uh, from, uh, from I think Virgin and one other company.
0:34:01 Yeah.
0:34:03 It was actually 5 billion in LOIs.
0:34:06 Um, 5 billion, 5, 5, $5 billion.
0:34:11 I still remember like Sam Altman’s tweet is that, you know, boom, had $5 billion at LOIs
0:34:14 at demo day as a record that probably won’t be passed soon.
0:34:14 Well, exactly.
0:34:16 So how the hell, how does that happen?
0:34:16 Is that bullshit?
0:34:17 Yeah.
0:34:21 No, I mean, so, so I’ll tell you the story and it involves the story about bullshit.
0:34:28 Um, the, uh, so we, we do YC and like Sam had been in our seed round and he had sort
0:34:31 of like, you know, this is back when Sam was running YC and he had sort of like been telling
0:34:32 me I need to do YC.
0:34:36 And I’m like, well, isn’t YC for like mobile social, you know, I don’t know that it’s
0:34:36 for supersonic jets.
0:34:38 And he kept saying, you have to do it.
0:34:38 You have to do it.
0:34:43 And eventually I was like, okay, my biggest risk is I never raised enough money to actually build
0:34:44 anything.
0:34:46 YC claims that they’ll help with that.
0:34:52 I’d, I’d rather try it and it wasn’t useful than, than not try it and fail and not having
0:34:54 given it every chance to succeed.
0:34:59 So I did, did YC and early on the group partners like, well, you need to show up with demo day
0:35:00 at, with sales.
0:35:06 And I’m like, this is like a 10 person company that just moved out of my basement.
0:35:11 Like I’d be lucky to, my customer pipeline is like Lufthansa United.
0:35:15 I’d be lucky to sell airplanes in eight years, let alone eight weeks.
0:35:16 And what am I going to do?
0:35:19 And so I was like, okay, there are two things that are possibilities here.
0:35:21 One, one possibility is a startup airline.
0:35:26 But if I look at an established airline, the only one that could conceivably do this quickly
0:35:27 is Virgin.
0:35:29 And only if I get to Richard.
0:35:34 And so I went, I went after both of those paths and we actually got a startup airline to do
0:35:34 it.
0:35:41 We got them to, there was a startup called Odyssey was going to do an all business class service
0:35:44 from New York to London city airport.
0:35:45 And I was like, this is great.
0:35:48 They’re doing the, you know, flying to London city, which is like the little airport in the
0:35:48 center of London.
0:35:50 That’s the best thing you can do short of being supersonic.
0:35:52 These guys probably get speed.
0:35:59 And so I met with a guy and he was willing to like, give me an LOI on like actually a different
0:36:00 corporate entity letterhead.
0:36:01 And I’m like, woohoo.
0:36:04 And now this, this LOI was for 15 airplanes at $200 million each.
0:36:06 So it’s a $3 billion LOI.
0:36:12 Explain what an LOI means in this context is LOIs can range from non-binding.
0:36:13 Hey, sure.
0:36:14 Sure.
0:36:19 I’m interested in taking a look to a binding LOI with hard money.
0:36:19 Right.
0:36:20 There’s, there’s a range.
0:36:20 That’s what I was saying.
0:36:23 When you’re talking LOI, what were you talking at this time?
0:36:25 So this LOI was a piece of paper.
0:36:28 And, you know, he started asking questions about it.
0:36:31 It’s from a startup airline, which by the way, hasn’t flown any airplanes yet.
0:36:36 Like, like this, you know, this was a PDF and it wasn’t worth the paper.
0:36:36 It was printed on.
0:36:38 This was the equivalent of, I have a girlfriend.
0:36:39 She just goes to another school.
0:36:40 Trust me.
0:36:43 It’s, it’s, you know, basically.
0:36:47 And, and so I’m, I’m, I’m doing the practice demo day pitches and like Michael Siebel, bless
0:36:48 his heart.
0:36:52 That guy’s got the, I think one of the brilliant things about PG is he’s built a culture at
0:36:53 YC where people just tell you what they really think.
0:36:55 It’s one of the best things about YC.
0:37:02 Um, and so I’m doing practice demo day and, uh, Michael Siebel looks at my slides and my
0:37:04 pitch and he’s like, Blake, do you have anything that’s real?
0:37:06 Cause you sound like you’re completely full of shit.
0:37:12 Um, and it, you know, it was bitter, it was bitter tasting medicine, but it’s what I needed.
0:37:17 And, um, and so I kept working on retooling the pitch to be focused on what hardware we really
0:37:18 had at that point in time.
0:37:21 And also trying to figure out this customer thing.
0:37:22 Cause I knew that LOI was flimsy.
0:37:26 And so we’ve been working on Virgin and there’s a whole other set of stories I could tell at
0:37:29 length about how I got to Branson, but, um, but I did get to Branson.
0:37:32 Well, tell us, we like the hustle stories.
0:37:32 Give us one.
0:37:40 So, so Mark Kelly, who is now Senator Mark Kelly, um, uh, shuttle commander, um, you know,
0:37:44 human extraordinaire in a bunch of ways, uh, astronaut Mark Kelly, astronaut Mark Kelly.
0:37:44 Yes.
0:37:50 Um, was on our advisory board and, uh, he hung out with Richard.
0:37:55 Um, and I sort of discovered I could ghostwrite emails from Mark Kelly to Richard Branson and
0:37:56 he would send them.
0:38:06 Um, and so I did, and this was, so this was like February, March of, um, 2016.
0:38:11 So Virgin Galactic is about to roll out their second generation spaceship.
0:38:14 Branson’s going to be in the Mojave desert for that event.
0:38:19 Uh, my chief engineer had actually gotten invited to go cause he was connected to those circles.
0:38:20 I hadn’t been invited.
0:38:27 And, uh, and so the, the, the pitch to Branson from Mark was the, Hey, the boom guys are going
0:38:29 to be in Mojave for your spaceship rollout.
0:38:30 You should really meet with them while you’re there.
0:38:33 And, uh, and he said, okay.
0:38:38 And so we got a 15 minute meeting and it was me and my chief engineer and Richard and Richard’s
0:38:39 mom.
0:38:41 Uh, I actually never got invited to the rollout.
0:38:43 I had to crash the rollout.
0:38:46 Um, but I met it, I managed to talk my way into it.
0:38:50 Uh, and, and I had this 15 minutes with Richard and he kind of, you know, uh, he’s
0:38:52 he asked us if we want anything to drink.
0:38:54 And I said, no, I’ve already had lots of coffee.
0:38:56 And I realized a couple of minutes into the pitch, he’s drinking scotch.
0:38:59 Um, it’s very early in the morning.
0:39:00 Um, I love Richard.
0:39:02 You, you, you, you failed the cool guy test.
0:39:03 Yeah.
0:39:06 Apparently, apparently I, I mean, maybe, maybe the pitch would have gotten better if I had
0:39:09 more scotch, but, uh, but at any rate, he’s like, guys, this is brilliant.
0:39:11 Like, I love what you’re doing.
0:39:12 This all makes sense.
0:39:17 And then he kind of leans back on his chair and he’s like, Oh, but I’m already doing Virgin
0:39:17 Galactic.
0:39:19 And that’s a lot.
0:39:22 And I don’t, I don’t know if I’ve got two of these things in me.
0:39:26 And I, and I said, Richard, we’re not asking you for money.
0:39:32 We’re asking if when this works, if you’d like the first few airplanes to be for Virgin, if
0:39:33 you want them.
0:39:37 Because if you’ll raise your hand and say, I want these, the product makes sense, then
0:39:38 I’ll go get all the money elsewhere.
0:39:42 Uh, and that turned out to be the thing that worked.
0:39:47 How did you think to, to say, instead of saying, uh, you know, invest in us or advise us or
0:39:50 whatever, just say, do you want the first ones to say Virgin on the tail?
0:39:53 Or do you want them to say Lufthansa?
0:39:56 Because the world is a lot cooler place if we write Virgin on the tail.
0:39:57 It was really, it was really Virgin versus BA.
0:40:02 And if you know him with a history of Virgin, you know that Richard, he hates BA, right?
0:40:05 What is Richard, what Richard cares about PR and he hates BA.
0:40:09 And when he tried to buy Concords, which he did, he tried to buy BA as Concords when they
0:40:12 were shutting it down and they wouldn’t sell it to him because they want to get embarrassed.
0:40:13 So what does this like?
0:40:17 Basically, Sean, I don’t know if you ever read his book or the listener, BA and Virgin, British
0:40:22 airlines, they had a battle in the nineties and early 2000s where BA was trying to shut
0:40:23 down Virgin.
0:40:24 And so he went on this whole campaign.
0:40:28 I think he brought like, is this when he brought a tank through London where any like rolled over
0:40:30 like a fake model plane?
0:40:34 Like it was like a whole PR campaign of the little guy Virgin versus the big guy BA.
0:40:35 Oh, it’s great.
0:40:36 The stories are great, right?
0:40:41 And he very specifically tried to beat BA with Supersonic and he lost, right?
0:40:46 And so, so he wants to do this and he cares about PR and he cares about his brand.
0:40:50 And so I’m like, why don’t I let you stick it to BA?
0:40:55 So it turned out, you know, so then the meeting ends and there’s no deal.
0:41:01 And I’m sort of like working it through my friends at Virgin Galactic at this point, trying
0:41:02 to get something done.
0:41:07 Um, at this point, uh, YC, the way YC was structured, demo day was spread across two
0:41:13 days and the company might not exist if we hadn’t been on day two because it’s so like
0:41:18 what happened, what happened that week is so, so Wednesday is our demo day, demo day two.
0:41:24 Monday, we were like launching the company out of stealth mode and we’d gotten, um, Ashley
0:41:26 Vance to write the launch article for Bloomberg.
0:41:29 And if you don’t know Ashley, he was like Elon’s first biographer.
0:41:33 We’d let him and the Bloomberg team come out to Denver and interview me and take all the
0:41:34 pictures they wanted to take.
0:41:39 And in my head, this is brilliant because the story is going to be boom is the SpaceX of
0:41:39 airplanes.
0:41:43 But we, I had no self-awareness about how darn early we were.
0:41:49 And I let the photographers take a picture of me on a plastic orange chair, climbing into
0:41:50 a cardboard mock-up of an airplane.
0:41:56 And Ashley actually wrote a nice story, but his editor picked the picture and wrote the
0:41:56 headline.
0:42:01 And the headline said something like this Colorado company thinks it can build a supersonic jet.
0:42:05 And then there’s my like fat ass climbing into a cardboard mock-up.
0:42:08 Um, and so that’s Monday.
0:42:12 I know it’s so bad.
0:42:12 So bad.
0:42:17 And it’s, and then it’s, and then it’s at the top of Hacker News and the comment, and the
0:42:19 comment, like photoshopped, like a helmet on your head.
0:42:22 Oh, I mean, it was so, it was so awful.
0:42:25 The comments are like, you know, what an idiotic company.
0:42:27 Don’t they know airplanes aren’t made out of cardboard?
0:42:31 And you know, what, what idiot runs marketing at that company?
0:42:33 Cause who would name a supersonic jet company?
0:42:33 Boom.
0:42:36 Um, and it’s brutal.
0:42:38 It’s just have, and I’m like, we are so screwed.
0:42:41 Like we’re just, we’re going to be the laughingstock at demo day.
0:42:47 And so that’s Monday, Tuesday, I’m sitting at my desk, working on the slides and up pops
0:42:51 this email from Virgin that says we’re in for the first 10 airplanes.
0:42:52 You can announce it tomorrow.
0:42:56 And I like read the email like three times.
0:43:00 Cause I’m like, there is, there’s like no way there’s, there’s like no way this says
0:43:01 what I think it says.
0:43:05 So we’re like, we’re like in San Jose in an Airbnb prepping for demo day.
0:43:05 Right.
0:43:09 And, uh, and so I’m like, I think, I think I just went from the biggest loser to the biggest
0:43:10 winner.
0:43:13 And I called up the team at YC and I’m like, I need to relaunch my startup.
0:43:15 Um, how do I do this?
0:43:20 And so I think I stayed up to midnight that night, redoing press pitches under embargo.
0:43:26 We relaunched the morning of demo day, uh, with a $2 billion LOI from Virgin done on an email.
0:43:32 Um, and, uh, and, and then we’re back at the top of hacker news again.
0:43:39 And the comments are like Monday, my, my favorite comments were like one, what genius runs marketing
0:43:42 at boom that the one, two punch, that’s how you launch a company.
0:43:48 And if there was another one that was like Monday, colon, ha ha Wednesday, colon.
0:43:49 Oh shit.
0:43:56 Uh, and, uh, you know, but by, by the grace of Richard Branson, we would have died that week.
0:44:02 You seem to have a lot of these stories that are, uh, what our buddy George Mack likes to
0:44:03 call high agency.
0:44:06 So you were a high school dropout yet.
0:44:10 You got into college and you, I think you high agencyed your way into college.
0:44:13 As I understand that you didn’t just work at Amazon.
0:44:16 I think you like kicked ass at Amazon and some, you got the job in an interesting way.
0:44:18 And I think you kicked ass in an interesting way.
0:44:23 This whole idea of like, I didn’t take at face value while the Concord failed.
0:44:28 And I kind of like taught myself the physics and calculus I needed to like diligence the
0:44:29 idea initially.
0:44:34 Um, it seems like you have a lot of these, what’s your favorite version of those stories that
0:44:41 you think, you know, it’s that I think your meter might be like, you don’t have the, what’s
0:44:41 it called?
0:44:47 Like the, um, like the thing that stops a car from going at a certain speed, like an artificial
0:44:50 governor, yeah, you removed your governor.
0:44:55 And so you’re willing to go further than the average person would when it looks like the
0:44:57 default answer is no, no, no for you.
0:44:58 Yeah.
0:45:01 Um, well, I want to understand, I guess a couple of things.
0:45:03 One is I want to understand things for myself.
0:45:06 Um, and maybe that’s the most important thing.
0:45:13 Like I don’t, um, funny side story as, as I was like going through a divorce and like fighting
0:45:16 with my ex-wife, uh, over like custody.
0:45:21 And I had to go through this like weird psychological exam and, uh, I’m going through, you know,
0:45:24 these like multi-choice questions where they ask you, you know, this random thing.
0:45:29 Like I could tell, uh, there were questions like, I think the experts are wrong and I know
0:45:29 better.
0:45:33 And I’m like, I think they’re testing for delusions of grandeur.
0:45:37 So I’m not going to, I’m not going to answer this one honestly, but that’s actually what
0:45:38 I think.
0:45:40 I think the experts are wrong all the time.
0:45:42 Anybody who bothers to think about it can figure out differently.
0:45:46 And, and so, so I have that premise, but I also, I don’t know.
0:45:48 I feel like I have a complicated relationship with my own ego.
0:45:53 It was a really weird decision for me psychologically to start this company.
0:45:58 It was like, I look in the mirror and I’m like, totally don’t look like the guy to do
0:45:58 this.
0:46:02 And it was very bizarre to tell my friends, I’m going to go build supersonic jets.
0:46:05 It’s like, I didn’t look like the person to do it.
0:46:07 I didn’t actually believe on the inside I was going to succeed.
0:46:08 I just didn’t want to not try.
0:46:12 Um, and I, and I really struggled with that.
0:46:14 And I remember thinking about, you know, who my business heroes were.
0:46:18 And I thought of, you know, I especially, I thought of a lot, but I especially thought of
0:46:24 Bill Gates because Gates had said, I think during the seventies that his goal for Microsoft
0:46:30 was to put a personal computer in every home and on every desk running Microsoft software.
0:46:34 And he said that in the seventies, right?
0:46:35 And then he actually went and did it.
0:46:42 Uh, and then some, and, and what was, what was it like to be Bill when Bill said that?
0:46:45 Like he didn’t have a resume for it either.
0:46:50 He could have flamed out and like, because he didn’t flame out, we know who Bill Gates
0:46:52 is and we have those computers.
0:46:56 But if, you know, so I’m like, okay, there must be a couple of categories of entrepreneurs.
0:47:01 So the people who like go after these big missions and they succeed and we all know their names
0:47:04 because it is Bill and it’s Steve.
0:47:07 And back in the day, it’s Thomas Edison and, you know, the greats of the great, right?
0:47:13 And then there’s probably like the dark matter of founders and the dark matter of founders
0:47:16 are the people who go for big things, who set big goals, but it doesn’t work.
0:47:24 And, um, would I rather be in the dark matter of founders or would I rather be in the like,
0:47:29 I didn’t try and I just had a job or I started another mobile apps company.
0:47:33 And I made the conscious decision that I’d rather be a dark matter founder.
0:47:36 That’s pretty badass.
0:47:38 Basically, you were willing to lose.
0:47:40 I had to be willing to lose.
0:47:46 I mean, another, another turn of phrase here is, um, oh boy, I’ll tell this through my story
0:47:46 of my daughter.
0:47:52 Um, she was, uh, when she turned 10, which is a few years ago now, uh, I took her out to
0:47:55 ice cream and it was, it was one of these like low moments where like I didn’t know how the
0:47:56 company was going to survive.
0:48:02 And, and by the way, we have one of those like every year, um, like with like regularity,
0:48:03 there’s like a life and death crisis every year.
0:48:07 Um, and I, I didn’t know, I didn’t know how we were going to get through this particular
0:48:07 one.
0:48:09 And I was feeling pretty down about it.
0:48:13 And like, you know, in my, I had this self-talk that was like, man, my daughter for her entire
0:48:17 conscious life, all her dad has been doing is saying he’s going to build supersonic jets.
0:48:21 And, you know, and it could totally, the first prototype might never fly.
0:48:26 Um, and you know, what the hell is my identity to my children?
0:48:31 Uh, and it’s just not really a great question, but I had that question.
0:48:35 Um, and I, you know, so she’s in the back of the car, we’ve just had ice cream.
0:48:40 And I said, Ada, like, what would you think if I failed at boom?
0:48:45 And I’m going to tear up as I say this, she didn’t miss a beat.
0:48:48 And, and she said, I’d be proud of you for trying.
0:48:52 And, uh, that speaks to me very deeply.
0:48:58 And, uh, that’s the view I try to have for my, myself, you know, do things I’d be proud
0:49:01 to try, but do things I’d be proud to fail at.
0:49:05 And I’ve always told the team, like, there’s no guarantee of success here.
0:49:07 We might fail, but if we fail, we’re going to fail honestly.
0:49:10 And we’re going to fail having given it our all.
0:49:12 And we’re not going to give up.
0:49:19 And when the, uh, when, when XB1, which is, that’s our prototype airplane, the, you know,
0:49:24 the first startup to ever break the sound barrier with that airplane, you know, when it landed
0:49:29 earlier this year for the last time, um, and I was standing outside the airplane with
0:49:32 the team of 50 people that had built it and flown it.
0:49:39 Um, and I said to the team, the reason, the reason we get to be here today is we didn’t
0:49:39 give up.
0:49:43 We got here because we’re the team that did not give up.
0:49:44 It took a whole lot of not giving up.
0:49:46 Other reasonable people would have given up.
0:49:48 A bunch of reasonable people did give up.
0:49:53 And to get, to get over to our airliner flying, that’s going to require a lot more of not
0:49:53 giving up.
0:49:59 So pick something you’d be proud to fail at and don’t give up.
0:50:03 New York city founders.
0:50:06 If you’ve listened to my first million before, you know, I’ve got this company called Hampton
0:50:09 and Hampton is a community for founders and CEOs.
0:50:13 A lot of the stories and ideas that I get for this podcast, I actually got it from people
0:50:15 who I met in Hampton.
0:50:17 We have this big community of a thousand plus people and it’s amazing.
0:50:22 But the main part is this eight person core group that becomes your board of advisors for
0:50:23 your life and for your business.
0:50:31 Now, to the folks in New York city, I’m building a in real life core group in New York city.
0:50:35 And so if you meet one of the following criteria, your business either does 3 million in revenue
0:50:40 or you’ve raised 3 million in funding, or you’ve started and sold a company for at least $10
0:50:42 million, then you are eligible to apply.
0:50:45 So go to joinhampton.com and apply.
0:50:48 I’m going to be reviewing all of the applications myself.
0:50:50 So put that you heard about this on MFM.
0:50:53 So I know to give you a little extra love now back to the show.
0:50:57 That’s a great story.
0:51:01 I also think that, um, you know, I’m not in your industry at all.
0:51:08 Um, Sean’s, uh, and I make internet stuff and I remember seeing this Elon Musk video where
0:51:12 his, the, the, the rocket, I don’t, I don’t remember what it did, but it was some threshold
0:51:15 that they had never accomplished before where it got to space, something like that.
0:51:21 And you see him looking up and you hear the launch control, like freaking out.
0:51:23 And he actually, I think he like cries.
0:51:24 It looks like he’s about to cry.
0:51:24 Yeah.
0:51:30 He’s like looking up and he’s like, it, it, it almost felt like he was even in awe or impressed
0:51:32 where he was like, I can’t believe it.
0:51:37 It worked and the whole crew, you know, a thousand employees are just freaking out.
0:51:37 Yeah.
0:51:42 And I remember thinking like, uh, you know, I don’t want to something like that seems so
0:51:43 challenging, man.
0:51:44 I couldn’t do it.
0:51:46 It took 15 years, 20 years to get there.
0:51:49 And then you see that video and you’re like, wow, that’s totally worth it.
0:51:51 And I, and I’m a little envious.
0:51:54 It’s sort of like someone like running a marathon and at the end of the marathon, their family
0:51:58 is there and they’re freaking out or doing some type of like crazy physical task where it takes
0:52:00 decades or years to work towards.
0:52:04 And then you have this like moment where it’s like, you know, there’s a very beginning and
0:52:05 a middle and an end to the journey.
0:52:07 And I’m very envious of that.
0:52:11 And it’s really cool that you had that, you know, recently, uh, it happened like six months
0:52:11 ago.
0:52:13 I forget that you guys like had your first flight.
0:52:14 Yeah, it was three.
0:52:15 It was like three months ago.
0:52:16 It was recent.
0:52:16 Yeah.
0:52:17 Three, three months ago.
0:52:19 And I remember having, I’m like, I have nothing to do with you, but I had this,
0:52:22 this sense of pride just for you.
0:52:26 Uh, and I remember seeing Paul Graham, who isn’t like a very, Paul Graham doesn’t seem
0:52:27 like a very excitable person.
0:52:30 And he seemed very excited about this.
0:52:31 And I was like, this is amazing.
0:52:34 And it almost felt, it felt very patriotic.
0:52:38 Uh, you know, that had nothing to, I don’t know if there was no like, it’s team ambition
0:52:40 instead of team America, right?
0:52:45 It’s, uh, yeah, I think there’s a part of all of us that wonders what’s the version of
0:52:48 me if I did the most ambitious thing.
0:52:51 If I did my version of supersonic jets, right?
0:52:53 And when I was little, I wasn’t a flight enthusiast.
0:52:54 I didn’t have my pilot success.
0:53:00 I, your thing is your thing, but I think everybody has a little version of that in them.
0:53:05 There’s some version of that in you, the most ambitious thing, the most you thing you could
0:53:05 possibly do.
0:53:08 And you probably fail and it’d probably be super hard.
0:53:12 And you could probably, if you’re smart, you have a lot of easier options if you decided
0:53:12 to choose.
0:53:14 And it could be small even like, that’s right.
0:53:18 Be a standup comedian or do a show all the way to go to space.
0:53:22 It’s the, it’s the biggest ambition rolled up to someone’s actual frame and their actual
0:53:23 values.
0:53:28 Like imagine going back to your five-year-old self and saying, let me tell you, I’m gonna
0:53:29 tell you what you’re going to get to do.
0:53:30 Here it is.
0:53:34 And like, what makes that five-year-old self just like tickled pink?
0:53:35 Like, wait a minute.
0:53:36 I get to do that?
0:53:40 Blake, have you ever read the Pixar rules of storytelling?
0:53:47 They have this thing called the 22 rules and the 22 rules, rule number one, the most important
0:53:51 rule, this is Pixar, Pixar who, if anybody knows how to move people, they know how to move people
0:53:52 emotionally.
0:53:56 Rule number one is you admire the character more for trying than for their successes.
0:54:03 And so, you know, the hallmark of every Pixar movie is not the happy ending, right?
0:54:06 It’s how the character approached the obstacles.
0:54:11 And this sounds like super, super obvious, but the reality is like, that’s also what,
0:54:13 you know, moves founders.
0:54:17 It’s also what inspires people is not the success.
0:54:18 Cause yes, it’s amazing.
0:54:21 That’s like Elon story with the rockets landing.
0:54:21 Wow.
0:54:22 That’s so cool.
0:54:25 The rockets landing on their synchronized in the middle of the ocean.
0:54:26 That is amazing.
0:54:30 But it’s like 10 times more amazing when you know that the first three rockets blew up and
0:54:34 that he went all in and that, you know, and that nobody was going to do this if he didn’t,
0:54:39 if he didn’t push forward and continue on in the face of like almost certain failure.
0:54:39 Right.
0:54:43 So I think that’s like one of the most important rules for founders.
0:54:45 Cause it’s what will inspire your team.
0:54:46 It’ll inspire, you know, customers.
0:54:47 It’ll inspire the audience.
0:54:48 It’ll inspire investors.
0:54:54 In the end is that you admire the character, how the character tries rather than their success.
0:54:55 I think that’s right.
0:54:59 One of our OG boom people has a metaphor for this that I found really useful.
0:55:05 He calls it the emotional piggy bank and he’s like, every time you’re struggling with a
0:55:11 problem and you push through, you’re putting a quarter in the piggy bank and when you finally
0:55:16 succeed, you get to break open the emotional piggy bank and the harder it was to get there,
0:55:17 the more joyous the victory.
0:55:19 Right.
0:55:22 And I think, I think he used to, this guy’s been a boom for nine years.
0:55:24 He’s one of the few early people that stuck it out.
0:55:29 Now he runs our engine program and, and, uh, I think he, I think he was using that with
0:55:33 himself a lot, but I’ve, you know, I’ve tried to broadcast it to the team.
0:55:35 Cause I think it’s really, I think it’s really true.
0:55:38 When do you think you guys are going to be mainstream?
0:55:40 When are you going to be, when are people going to be flying?
0:55:44 Cause right now you’re at this point in the company where it’s like, all right, you’ve
0:55:44 raised 700 million.
0:55:51 So obviously you’re a big deal, but you’re not to the point where it’s like, uh, this is
0:55:52 a thing, this is going to work.
0:55:56 Uh, when do you think that that’s going to cross this?
0:56:00 Or, and, uh, I guess it’s been 15 years, uh, or 12 years.
0:56:00 Yeah.
0:56:04 Uh, 11, uh, we’ll turn 11 on paper in September.
0:56:04 Yeah.
0:56:07 11, 11 years ago, I was in my basement reading textbooks.
0:56:07 Wow.
0:56:08 So not that long ago.
0:56:11 And now when, what’s the next chapter of the story?
0:56:15 So you got through a bunch of chapters, you got through the crazy guy in his bed, bedroom
0:56:16 to, Oh, okay.
0:56:19 This is kind of interesting to, Oh my God, he made a prototype.
0:56:22 This is actually, this is actually potentially serious.
0:56:25 Now the next chapter, what’s that going to be?
0:56:27 And when is it going to be, uh, when are we going to read it?
0:56:33 You know, one way to look at this is like, you know, progressive overturning of the skeptics.
0:56:36 Um, that’s not how I see it on the inside, but it’s one way to look at it.
0:56:42 You know, the skeptics said a startup could never sell airplanes to airlines.
0:56:45 Oh, we did United bought them, made a deposit.
0:56:46 American did.
0:56:47 Japan airlines did a pre-order.
0:56:48 Okay.
0:56:48 That happened.
0:56:51 Uh, a startup can never build a supersonic jet.
0:56:53 Um, Oh, we did that.
0:56:54 Okay.
0:56:58 The next thing skeptics say is, um, we’re never going to succeed at building our own jet engine.
0:57:02 Like there’s a whole class of people who are just like convinced that only big companies
0:57:03 can build jet engines.
0:57:07 And, uh, we’re going to find out pretty soon who’s right.
0:57:12 It was the end of this year, our full scale jet engine prototype, you know, should be running.
0:57:15 And then next year we’ll start building the first airplane.
0:57:22 And our, our goal is to roll the first one off the line in 27, uh, fly it in 28 and be ready
0:57:23 for passengers in 29.
0:57:28 And there’s a good chance that like it could take longer than that, but those are, those
0:57:29 are the goals.
0:57:34 And I, and I, I believe in, uh, we’ve got a lot, uh, gotten a lot of learnings along the
0:57:37 way about how you set goals and how you set schedules, which I can talk about.
0:57:44 But my, my conclusion is ambitious schedules result in the fastest actual execution.
0:57:46 And so that’s, those are our targets.
0:57:51 You know, it’s a cliche that I say this at the end of the podcast, you know, it gets to
0:57:52 the point where someone says something amazing.
0:57:54 I go, man, you’re, you’re the man.
0:58:01 Uh, uh, and so I’ve overused that phrase, but I think that, um, of the people who I look
0:58:07 up to are, it’s almost, you’re potentially going to be an American hero.
0:58:09 And I, and I think that like, we’re honored to talk to you.
0:58:14 And I think that, that, um, I hope that you are, because it would be really fun to have
0:58:14 you win.
0:58:17 It would be, it would give us all a huge sense of pride to watch you win.
0:58:20 And, and, and I think the, the jet thing is cool.
0:58:25 The, but the cooler thing is that you’ve had, you had a crazy vision and it might actually
0:58:26 come to fruition.
0:58:30 You know, I appreciate your saying that it’s a weird, and again, I have a weird relationship
0:58:34 with my ego on this, but I think back to like my days in college and I was reading my favorite
0:58:35 book, which is Atlas Shrugged.
0:58:43 And my, my favorite character in Atlas Shrugged is this guy, Hank Reardon, uh, who is this sort
0:58:49 of combination business technology hero, um, who like invented a new kind of metal.
0:58:55 Um, and, uh, and I, but I remember crying and thinking like, man, I don’t have it to be
0:58:56 somebody like him.
0:59:01 And, uh, you know, I always wanted to be, but I didn’t think I could be.
0:59:07 And along the way, someone, someone told me that this, the things we admire in other people
0:59:09 are actually our own strengths.
0:59:11 And at first that made no sense to me.
0:59:17 Uh, but as I start to pattern match about it, like, like my own weaknesses are the things
0:59:20 that annoy me the most in other people and my own strengths are the things I admire most
0:59:20 in other people.
0:59:23 It’s very paradoxical, but it seems to actually be true.
0:59:30 And, uh, and so there’s this like weird thing where I think we could actually become our heroes.
0:59:35 Um, and, and my, you know, of all the various random things that were said about me after
0:59:40 we broke the sound barrier, the one that spoke to me the most was where someone who I’d never
0:59:42 met, never heard of compared me to Hank Reardon.
0:59:44 Oh, that’s awesome.
0:59:45 Yeah, that’s amazing.
0:59:49 I always say, if you spot it, you got it both on the good and bad.
0:59:52 If something bothers you about some other people, it’s because there’s a part of you
0:59:54 that recognizes that behavior.
0:59:58 Um, and same thing, if something inspires you, there’s a part of you that identifies with that
0:59:59 behavior, right?
1:00:01 You are what you admire.
1:00:05 And, and I think that that, once you realize that you start to get, actually, you start to
1:00:08 pay some attention to what you choose, what you’re choosing to admire because you’re actually
1:00:10 pointing your little compass in that direction.
1:00:14 Um, and you know, then there’s just a question of, are you going to remove the governor?
1:00:16 Are you going to leave it in and not actually go chase it all the way?
1:00:17 I love this.
1:00:18 That’s the, that’s the happy side of it.
1:00:22 And then the unhappy side of it is the things that drive me crazy and other people, holy shit,
1:00:24 I need to have a dog with myself because I’m probably doing it too.
1:00:25 Right.
1:00:27 I like this quote that you have.
1:00:30 You said, if every founder worked on the most ambitious thing they could get their head
1:00:34 around, everyone would be happier and more great things would get built.
1:00:37 You know, there’s probably going to be somewhere between half a million and a million people
1:00:39 who listen to this episode.
1:00:44 Um, like, I guess if you were going to leave here making your case for that, for why, why
1:00:46 founders should work on the most ambitious thing.
1:00:48 Um, what’s your case?
1:00:58 Can’t lose if you win, obviously it’s great, but I think the, I think it’s a mistake to
1:01:01 start from your resume and it’s a mistake to start from what you think you can do.
1:01:08 is I think the only way to find out what you can do is to pick the most motivating thing
1:01:10 in the world and, and run at it.
1:01:15 Something that’s so motivating that the goal matters more than your own insecurities, that
1:01:20 you could do that thing where you extrude yourself into the noodle of the right shape.
1:01:22 That’s the only way you find your limits.
1:01:28 By the way, you were really young and I think I read that you reported directly to Jeff Bezos.
1:01:30 I can’t let you leave without asking you.
1:01:31 Do you have any good Bezos stories?
1:01:32 Oh, I’ve got a bunch.
1:01:33 I did not report directly to Bezos.
1:01:39 The, one of the most annoying things that happens as the, uh, as you go through these journeys
1:01:42 is like little bits of bio get turned into better soundbites.
1:01:46 And then I feel embarrassed because like, like people claim I was an executive at Amazon and
1:01:50 I was not like, well, someone was like, what actually, oh, he, uh, he worked at Amazon.
1:01:51 Oh, so he works for Jeff Bezos.
1:01:53 Yeah, he, he, he worked for Jeff Bezos.
1:01:54 Oh, he worked for Jeff Bezos.
1:01:55 Right.
1:01:57 So sort of every hourly worker in the warehouse.
1:02:00 Now I did get, I did get able to do something that Jeff cared about.
1:02:02 So I got to work with him a bit.
1:02:07 Um, but that meant that like, I was updating him once a quarter and, you know, and if I
1:02:10 screwed up really badly, like Jeff would hand my ass to me.
1:02:13 And, and the, by the way, there’s no better early career experience than to be like 22
1:02:15 working on something that Jeff happens to care about.
1:02:17 And when I screw it up, he tells me.
1:02:21 And so I found out later that I was the youngest ever manager at Amazon.
1:02:26 I don’t think I knew that at the time, but I got to build the, um, uh, the thing I got to
1:02:29 do was basically do Amazon’s first ad buy from Google.
1:02:35 And this, you know, and build the system that was, I think the first automated ad buying
1:02:35 system on the internet.
1:02:41 This was before the, the, we were buying AdWords before there was an AdWords API with like screen
1:02:44 scrapers that were like automatically clicking buttons in the background with Perl scripts.
1:02:49 And, uh, it was, my experience of it was, it was like standing next to a rocket and then
1:02:54 the rocket took off and like my like jacket got caught on the rocket and I kind of was along
1:02:54 for the ride.
1:03:01 Uh, but at some, at some point this thing was, was driving 7% of Amazon sales and 7% of Google
1:03:03 sales all at the same time.
1:03:10 Um, and, and somehow I just, you know, I, I, my experience of it was I was like on the precipice
1:03:12 of failing and they were about to fire me and replace me with somebody who actually knew
1:03:13 what they were doing.
1:03:17 Um, and, and I was like right at that line and never quite crossed it.
1:03:22 Um, but it was a, it was a great first go build something from scratch gig.
1:03:26 And, uh, and I got to learn a lot from that experience and I got to know, got to know Jeff
1:03:28 a little bit, but like, I didn’t work directly for him.
1:03:31 I was like, what’s he like and what’d you pick up from him?
1:03:34 Oh, I really admire Jeff.
1:03:38 The stories they get told about CEOs tend to be the ones about how they lose their cool and
1:03:40 yell at people and fire people in the elevators and whatnot.
1:03:45 And one of my favorite things, and I would watch Jeff lose it from people a couple of
1:03:49 times, but what I found is he never lost it with me so long as I took accountability.
1:03:55 And I remember the very first time I was presenting to Jeff, we had just launched like the MVP of
1:03:56 this thing I was describing.
1:03:59 And I’m like telling Jeff how he built it and why.
1:04:03 And I’m like nervous AF cause I’m like 22 or 23 presenting to like this God.
1:04:07 And we get partly through the presentation and it’s going well.
1:04:09 And then he says, well, why didn’t you do X?
1:04:10 And he’s got this idea.
1:04:12 And I said, well, we didn’t think of that.
1:04:16 And, and, and he starts laughing, right.
1:04:19 He starts laughing the big famous Jeff Bezos laugh.
1:04:21 And he says, that’s a great answer.
1:04:24 It’s true all the time, but nobody’s willing to say it.
1:04:31 And, and so what I found was like, you know, whenever I just told Jeff the truth and took
1:04:34 accountability, like there was another time I was in front of the old executive team and
1:04:36 the temperatures going up in the room.
1:04:39 I was like, why did we do this when this other thing was a higher priority?
1:04:43 And you can just, everyone’s get progressively more pissed off that we’ve misprioritized.
1:04:46 And I just spoke up and said, that was my call.
1:04:47 I got it wrong.
1:04:48 I misprioritized.
1:04:49 I won’t do it again.
1:04:51 And, and the tone of the room was okay.
1:04:53 And the conversation moved on.
1:04:59 And obviously I couldn’t do that every single time on every single thing, but Jeff, Jeff rewarded
1:05:00 straight shooters.
1:05:02 Jeff rewarded accountability.
1:05:06 Jeff rewarded knowing, knowing your own business, like the back of your hand.
1:05:09 And he was, he was tremendously forgiving for learning on the job.
1:05:11 And I, I have huge respect for it.
1:05:14 The other thing is like, I’d go in to talk to him once a quarter and you’d like, you know,
1:05:19 and I felt like I knew my shit and he would hand me like a novel insight in five minutes.
1:05:21 I’m the thing that I did every day.
1:05:26 And I think that goes to like being really smart, but also that first principles thing.
1:05:28 As you go to first principles, you can actually get to novel insights.
1:05:30 That’s exactly what Emmett said.
1:05:32 Amazon bought Twitch for like a billion dollars, whatever.
1:05:33 So he reported to Jeff.
1:05:36 And so he would go, I think twice a year, three times a year, go meet him.
1:05:38 And he said the same thing.
1:05:40 He’s like, he wants you to know your business.
1:05:44 He’s like, but then within five minutes of sort of reading the document, he’s like, without
1:05:48 fail, he would give me one thing that I thought was kind of impossible.
1:05:54 I think about this business 24 seven and he gives me an idea or an angle or perspective,
1:05:57 like a novel perspective or novel idea that I didn’t have.
1:06:00 And he’s like, that’s amazing.
1:06:03 That is a, you know, that shows kind of the level that that guy’s at.
1:06:07 He’s super smart and he’s very first principles.
1:06:11 And if you put those two things together, that’s what actually, I think that’s what makes my
1:06:12 experience and Emmett’s experience possible.
1:06:15 And it’s the thing that enables other leaders to do the same thing.
1:06:20 The thing I try to challenge myself to do is at any given like management review or working
1:06:23 with a team, I try to ask myself, what’s the most important question?
1:06:27 And many, many times what I find is no one’s asked the most important question.
1:06:29 It’s actually not hard to find it and not hard to ask it.
1:06:30 That’s pretty brilliant.
1:06:32 What’s it, could you just give us an example of that?
1:06:36 Like a situation where you, you asked that question and it shifted the convo?
1:06:37 I got one from yesterday.
1:06:38 That’s sort of an example.
1:06:43 I called the Overture leadership team together on a Sunday.
1:06:48 My spidey sense was firing that we weren’t aligned about development philosophy.
1:06:52 And we start talking about when to insource and when to vertically integrate.
1:06:56 And, you know, the conversation in the room started, I was like, oh, vertical integrations
1:06:57 is a goal.
1:06:59 So we’ll eventually do all these things.
1:07:03 And I tried to get the conversation to like, no, it’s not.
1:07:07 Like what we need is the winning strategy.
1:07:11 What we need to decide is when do we want suppliers and when do we want to do things ourselves?
1:07:14 And what are the principles by which we make those decisions?
1:07:17 And then, so I went to the whiteboard and the room started like trying to answer those
1:07:20 questions, like how do we know whether we should do something ourselves or outsource it?
1:07:24 And I don’t think we’ve completely cracked the nut on that, but we at least brought the
1:07:29 team’s focus not to like, what are the answers, but how are the principles by which we make
1:07:30 those decisions?
1:07:34 And I think if we pull, I think we’ll keep pulling on that thread and ultimately the answer
1:07:38 to that question will be part of our success story as a company, because we’ll have understood
1:07:39 how to think about it.
1:07:43 And we’ve got the team on a set of principles that will then, if they won’t need to make every,
1:07:46 bring every supplier decision to me, they’ll like, they’ll, they’ll,
1:07:50 they’ll like, look, understand the principles and make great independent decisions.
1:07:51 Dude, Blake, you’re awesome, man.
1:07:53 You’re a, you’re a very unique founder.
1:07:55 Met a lot of founders.
1:07:56 You’re a very unique guy.
1:07:57 And what you’re doing is awesome.
1:07:58 I really appreciate you coming on.
1:08:02 And I hope you, I hope my keyboard wasn’t making too much noise because I kept writing
1:08:06 down these little quotables that I thought were pretty, pretty great for me.
1:08:10 The best episodes, Blake, the best episodes, you’ll either, you’ll see Sean and I do two
1:08:11 things.
1:08:16 You’ll see us do this and we like are gazing or the other thing that I, that we do is we
1:08:17 just, you see us do this.
1:08:21 You see us just lean back and cross our arms and like classes in session.
1:08:22 Uh, well, thank you.
1:08:24 I had a lot of fun.
1:08:24 Yeah.
1:08:26 Where should people follow you or follow the journey?
1:08:29 Where do you want to direct people who want to kind of stay in touch here?
1:08:31 Um, I’m pretty active on X.
1:08:35 So I’m at B-Scholl, B-S-C-H-O-L-L.
1:08:39 Um, that’s the, uh, that’s probably the best place to follow along.
1:08:42 I, I try to give people like an inside view on what’s going on at boom.
1:08:44 And then I, I mouth off about other random things in the world.
1:08:44 So.
1:08:45 All right, man.
1:08:47 Well, I look forward to flying everywhere in half the time.
1:08:49 Thank you for, uh, for coming on.
1:08:50 Thank you for doing it.
1:08:51 And, uh, all right, that’s it.
1:08:52 That’s the pod.
1:08:54 I feel like I can rule the world.
1:08:58 I know I could be what I want to put my all in it.
1:09:00 Like no day’s off on the road.
1:09:01 Let’s travel.
1:09:02 Never looking back.
1:09:09 Hey everyone, a quick break.
1:09:12 My favorite podcast guest on my first million is Dharmesh.
1:09:13 Dharmesh founded HubSpot.
1:09:14 He’s a billionaire.
1:09:16 He’s one of my favorite entrepreneurs on earth.
1:09:22 And on one of our podcasts recently, he said the most valuable skill that anyone could have
1:09:25 when it comes to making money in business is copywriting.
1:09:29 And when I say copywriting, what I mean is writing words that get people to take action.
1:09:32 And I agree, by the way, I learned how to be a copywriter in my twenties.
1:09:34 It completely changed my life.
1:09:36 I ended up starting and selling a company for tens of millions of dollars.
1:09:40 And copywriting was the skill that made all of that happen.
1:09:45 And the way that I learned how to copyright is by using a technique called copywork,
1:09:49 which is basically taking the best sales letters and I would write it word for word.
1:09:52 And I would make notes as to why each phrase was impactful and effective.
1:09:55 And a lot of people have been asking me about copywork.
1:09:56 So I decided to make a whole program for it.
1:09:57 It’s called Copy That.
1:09:59 CopyThat.com.
1:10:00 It’s only like 120 bucks.
1:10:04 And it’s a simple, fast, easy way to improve your copywriting.
1:10:06 And so if you’re interested, you need to check it out.
1:10:07 It’s called Copy That.
1:10:10 You can check it out at CopyThat.com.