Yeah. You know, it's, uh, it's a bit of a crazy story and I'm sure that deserves a, a movie script someday, but essentially I was in the Marine Corps. I worked in national security after the Marine Corps. And then with the planning for the Iraq war, I basically had this harebrained idea that I would go and build capabilities for the U S government.

 And since I was so small and worthless, I had no money. I was nothing in the big scheme of things I decided my competitive advantage was to just go down range. Build this capability. Now, part of my plan didn't work, which is, I figured as soon as I laid out my brilliant plan to my friends in DC, they, and maybe their fathers or rich friends would all give me money and I would have a bunch of money to go build a company like most founders do instead, everyone was like, you're an idiot, you're a dipshit, you're going to die.

You're going to be in an orange jumpsuit. Like, don't do this. You're going to embarrass your country, all everything. Right. And that's what every founder here. So I heard that. Screw you. I know exactly what I'm doing. And instead of fundraising, I mean, I did try to fundraise for a few weeks, but I realized that even if everyone was saying, no, I fundamentally believed in what I was doing.

And I took what little money I had. I took an equity credit line from Navy federal credit union. I had bought these old, like literally crack dens and shitty houses in DC. And it was renting them out, fixing them. So I took a line of credit against the only things I had bought and saved up with my money

So you took a line of credit on the crack dens.

on the rental homes.

I mean, they were nice, little, not nice. They were like, they're nice little rental homes in DC. And I picked well, and so I took an equity line of credit and I took five credit cards and I flew into Jordan and I spent a couple days just drinking at all the bars in the seven circles of. And I found the right guy and I found this and I was dressed up as a CNN reporter.

I had bags with CNN taped on the side and I bought these cameras that may be like, nice looking cameras. I convinced this guy that was going into Iraq to create content. And, you know, I was going to, I was a reporter. So This guy takes me across the border of Western Iraq from. At like two in the morning we crossed the border and I came and tell you the shit we went through.

And I ended up in Baghdad and I, you know, everyone has all these stories about, oh, Paige was in the CIA pages and this thing, I was like, look, honestly, I had nothing. I was a guy who a few weeks before didn't work for the government, I had completely left. I had no more affiliation.

Like this is not some secret operation. That's going to be disclosed some day. This is just me. So. I believe there's a great opportunity here. didn't think it was gonna make me a lot of money. I just did it because I really believed that we needed the special intelligence and other capabilities down the road the very near future.

And I would be the one to build them. that's what I did. And that business, uh, was miserable and it was horrible and it was fun and exciting all at the same time. And, you know, I ended up getting, you know, a couple of dozen of my friends killed along the way in the, before. And I ended up just going through, some great moments where we saved people's lives, where we changed operations.

I mean, we were in Fallujah before both significant battles. We were in there working, like we had real impact with everything we did, we had massive impact, and we mess things up. Like all companies do. You know, we were in front page for running programs that people disagreed with. We used to run a, I won't get into it, but we did things that people did not agree with.

I'll tell you this, every operation we accepted. I believe in it just sort of like that political thing now, where you have to be like, I endorse this message or whatever. I endorsed every mission we took and, and I can stand behind all of them. If they ever get released in declassified Sunday, I turned down missions.

I finally did not believe in because of many other reasons, but I built an amazing capability for our country. You know, I close hundreds of millions of dollars in business. I never got any outside funding. And I built an amazing company that span the middle east Africa, Southeast Asia, south America, even Europe.

And we ran unconventional operations aided by technology. We sold that business into a group called , which is a multi-billion dollar defense contractor. I took my money, but more importantly, my lessons learned about how to create something from nothing. And I started angel investing back in 2009.

Okay, so a few questions. So first off, so you get to Baghdad, you've got your credit card, your five credit cards, and you're dressed as a CNN reporter, you know, do you have to like buy weapons? Like how do you get going? And this and this, I know how to start a SAS company page.

Well, the, I didn't bring my credit cards. Well, I think I may have brought one or two, but, it was a cash based economy. It was a cash and trade.

Okay.

So , how did I get my weapons while I broke up? Repeatedly until I got, , cause at the end of the day, there's this real irony, which is, um, you could have weapons if the us government gave you permission to have weapons, but you had to have a mission with them, but I didn't have any contracts.

I literally went there with no contract. Most contractors would work in the U S get a contract, you know, and then go down. Right. And I decided to short change that and the way I could beat AIC and Booz Allen, all the big guys was just to be on the ground, build the capability, and then they would hire me, but I wasn't allowed to have weapons until hired me.

So I was like, well, you know, uh, need to protect myself and my people and get the job done. I'm hoping to statute of limitations is over, but we just bought weapons illegally.

Okay, has one does damn it's

a crazy story.

That's just touching the surface, but we did what we did. when you meet founders, you realize all founders break the rules and you have to break the rules for the right reasons. At the right times we broke these rules around weapons, because honestly you need to have weapons.

I mean, the number of times we were attacked and ambushed and I almost died. It was serious shit. we did not live in a green zone. We lived like everyone else. We lived in the red zone. We operate in the most dangerous environments and you know, we're not supposed to have weapons, but we needed them.

So we got what we needed, but we didn't, go overboard. Like I didn't become a weapons broker, like other assholes did I wasn't trying to make money selling weapons. I was like, I just need weapons. So that. people want to mess with us. We can take care of ourselves.

This is interesting. We did things very differently. There are other contractors out there who believe the best way to stay safe was to look like a big up armor. Do you know every weapon, big, old fancy vehicles. We disappeared. We were ghosts. Like our philosophy was to just blend in, not draw attention. We were not out there trying to look for a fight.

 We usually took on missions that didn't require us to be over

Yeah.

awesome. I mean, like, I'll be like VC, like first principle thinking like, I wouldn't want to stand out and that if I were you, but, um, okay, so you grew this to, I think hundreds of millions of dollars, and this is what enabled you to become an angel. Okay.

Yeah.

And so you went from there to, I'm going to invest in tech.

 How did you get going? How did you make that translate?

Yeah. The first start was, I was selling, the company and I was trying to decide what's now. So I decided I really like company building. I like tech and in oh nine, I decided I'm going to go to Silicon valley and I'm going to become an angel, I think.

And so Navy seal, buddy of mine who was working sort of like crossing the gap between Virginia and Silicon valley. Connected me to a handful of VCs and the first guy to serve, raise his hand and say, Hey, I'll, I'll help you out is a guy named Eric chin and Eric runs crosslink capital.

 amazing human, and he and his network for the first people to invite me to an event. I went to this event in San Francisco and I just fell in love with the ethos of these founders. These people reminded me of , me several years back where they're, under-resourced no one believes in them.

They're taking on huge missions. That mean everything to them. And I just saw all these psychological parallels to what I went through. And I was like, look, I can't tell you how to develop a server farm but, well, I can tell you how to do. Is how to lead people.

I can help you figure out how to make something that people will pay for. I can help come up with products and solutions and I've been through the school of fucking everything up and learning what not to do. , one quality I have that I think has stood out as I like helping people.

like I really enjoy my time when I find people who give a shit. I have no problem waking up at three in the morning and spending two hours talking to people through hardship. I have problem camping out for a week in someone's office helping them out. I also get bored quite easily. Well, I saw early on, I could work on 50 different problems and never be bored

So I love the whole construct of being an early stage investor.

as do many people, I mean, as do I, but that doesn't always lead to such an amazing portfolio. tell me about some of those early investments you made? there are a lot of iconic companies.

Yeah, I, you know, there's always a bit of luck in investing, and me that, cause there is luck and the way you impact that luck is you have to play a lot of hands and this is where people mess up and investing. If we knew, like if you and I actually knew every deal to do, we wouldn't have the failure rates that we have.

 A little north of 10% of my seed deals across a hundred plus deals now have become unicorns. We have 20 unicorns in the portfolio and 10.8% of the ones that we started at seed became multi-billion dollar winners. But obviously that means I'm still 90% wrong. And if you look at, uh, you know, we're in the top two or 3% of funds worldwide, but all the great funds are still 85, 90, 90 5%.

 I mean, if you're a late stage investor, no problem. You can put together a fund you look a lot more like private equity and you're right. 89% of the time. But you and I are in the world of like, look, we're going to help discover the next generation of talent.

 And we're going to be good mentors to them without, you know, fuck you up the company. Because most of the time, what investors do. A lot of investors, really ness founders up. And I say that, have you seen a lot of bad investors, investors mistake their abilities.

Right? We get overconfident in the same way founders do. And we start to give founders bad advice. And we forget that these people that we invest in, they live their business every minute of it.

Yeah.Oh, I didn't even, got way off the top. I get, you can tell you how I just went through all the craziness. So I have funded all these amazing companies, but I'll tell you about a couple, that I think are interesting. One was scale is scale to scale is still a seven and a half billion dollar company.

And you know, we'll probably be 15 to 20 billion.

And is this an Outlander fund one company.

this is fun one. Yes. So we invest in them. April, 2016 is when Lucy, reached out to me. So Lucy hits me up on Twitter, has an idea. We engage. And then say, Hey, come down. Let's go hiking. So we go hiking through Santa Monica mountains, just brainstorming, listening to her she's a fascinating woman and she just launched her second company core fans here.

And Lucy has this huge vision. The weird thing is I think it's wrong. Like, I think her idea for a business, this is really wrong, but I think she's really right.

And the scale is basically training.

it's a platform for companies to sort of manage and tag and train, all the data that you need to build machine learning.

Okay. So I'm, I'm curious. Keep going with the Lucy story.

Yeah. So, Lucy's initial idea. They have two things. One is they're going to build AI, for this like medical platform. The second is AI for dating. That became apparent that the ideas were sort of like when you see a founder grasping for something that, you know, they don't love, but in their core you realize , they're really special people.

So with Lucy and Alex, you know what I told them, what I wrote up to my partners, We're to do this deal. And all my other partners disagreed with me on this deal, but we did it anyways.

And we cause the false negatives are far more damaging than false positives at this stage. But I saw something special in Alex and Lucy So we iterated and Lucy eventually I think it was two or three months later, came up with the idea of, , what scale is today.

And the idea was an API for all the human labor that was needed to do tagging in AI. And that, led to what scale is today. And there's a lot of lessons in there, which. When you go this early in investing, you have to remember that the business model, the idea, all the things that people are trained to make for you, or that they make themselves all these artifacts are just that they are artifacts.

They are representative of a person who made them. And so I always keep this in mind. I always think of investing a lot like archeology and early. You look at these artifacts and you ask yourself, when I look at a product or a spreadsheet, why was this decision made? I look for the interesting points around products or spreadsheets or business plans, and I'd go back.

And I asked the person who made the more, find the person who made them and asked them about their decision-making and what led them to create this artifact. That was something I realized I think a year or two in investing was treat every object in diligence as an artist. Like you're an archeologist.

 We look at the artifact and we, judge the pyramids for the pyramids, but that's not, what's important. Like why were they built in this deck? Yes. This deck is a bag of shit in the spreadsheets of the real estate that why was it built and how is it built?

That's what really fascinates me. And then we get into these events. I had mapped out 38 human characters. , this is how we invest. , they're all organized under the vision intelligence, character and execution domains, which I just used vice to make it easy to remember. within each domain, , there's these 38 characteristics.

They're all observable. They are things that every human exhibits to some degree or another, and we pull them out of people by having conversations. Politics and elections and church and sports and life. and we talked to founders and the whole time that we're talking to them about their business and their life, we have very interesting conversations.

 You know, and it's, it's a pipeline, but everything comes down to identifying very unique. People the Outlanders, you know, that's where the name of our fun comes from the fact that we are looking for extremely unique people who are highly inclined to build fast growing highly scalable tech companies.

When most of the world around them is saying, fuck you, you're an idiot. We're not going to give you resources founders overcome monumental things to be success. So we looked for all these very special things. At the end of the day, we back the humans behind the businesses.

Yeah. And yet, you know, a lot of those, like, let's talk about intelligence. how do you define that? How do you judge it, I guess, by having these conversations, are there things that you found helpful in sort of making these

judgements? I guess.

so that I have intelligence just doesn't mean smarts. so EQs, obviously part of the equation. so the human part is important, even though we invest in a lot of dysfunctional people.

Um,

Sure.

there's a level of that we're looking for. I'll give away one of them, which is really looking for the intellectual honesty. And there's a lot of smart people just lie to themselves They think quite often that they're the smartest people in the room, And these, founders are usually very smart, but they don't recognize talent around them. And they're very bad at incorporate other people's intelligence and capabilities into the mission.

And so those people are dangerously.

then there's other people who just are intelligent, but they're emotionally weak. they're very smart people, but when you see their outlook on life and what they're doing and how they're progressing, or like they just don't understand themselves so these different levels of intelligence that we look for that go beyond just being a genius engineer or genius business person or a genius deal-maker

and do you actually pull out what are these like archetypes? where you, like, say like, this is a dangerously smart this emotionally we do have. Archetypes that you gravitate towards, or that are winning architecture.

No, haven't built archetypes. So our process is we go through all the characters. And we rate each characteristic on a Likert scale and you have to write up evidence as to whether you have observed it or not, and why, As you've been doing this over the years, are there any ways that your sort of lens has evolved or any questions you've added or sort of non-intuitive, characteristics that you've been pulling out questions you've been asking.

Yeah. So my philosophy is every winter. Sort of like Thanksgiving through MLK. That's a period for me to reflect. And so I'm always listening. I constantly consume podcasts. I read books and talk to founders , I have a little note file on my phone, And then every winter I sit down and I decide if I'm going to make a change or not this model is now. about 14 years old. , so we, haven't made too many tweaks to it, but we do make a tweak every year.

Um, are there any good questions that you like to ask that you think really get to the heart of sort of who someone is?

No. And this is one of the fun things about the game is you walk into every arena blindfolded, and you have no idea what, your opponents are going to have in their hands or who they are. Right. But when I sit there's, I have 10 techniques that I use. A lot of it though is listening and then reacting.

So I have one general technique I'll share. I visualize every person's life. Do you remember back in like English language, where they would have you graph out sentences and you would have to graph, like the verb and the ad, all that stuff. Right. I look at every person's life, uh, as sort of a graph.

And when I tried to figure out is, all the key points in your. When you actually started having agency around your life, make key decisions. And so I try to get early and find out if there's important things happened, what was important to you? What mattered, when you talk about, and I really try to get into hard questions.

Like I'll ask very direct, sensitive things that might even some rude or insulting, like really, really personal. Cause I want to understand what impact that person's life and what I'm trying to find these pivots. Whether it's death of a parent trauma, you had to make a move, you won an election, you got something that you didn't think you'd get low points and high points.

And what you'll find with most, really good founders is they realize they had agency early in life and they charted their own courses. what it comes down to is in a moment when someone should have had agency, are they someone who took power over their own life and led themselves and others through them?

That's what I'm looking for.

Fascinating. and is this published anywhere? can I go look at your 38 points or is it like, that's your secret sauce?

 It's a secret sauce. It's what's led us to success, but I also believe we should all be building frameworks that work for us because , you know, things, I don't, you know, people I don't, and if we all copy each other, then we're going to be just as bad as the people that used to fund, you know, young, rich, white kids out of Stanford.

So let's, have a bunch of different founder frameworks out there. And then maybe in 10 years, let's compare notes.

But it's almost more like, I just like, have you ever put yourself through the founder framework?

Um,

no, so the way it works is usually either I'll hear a podcast, I'll read a book or I'll hear about someone. And one thing I always ask I'm asking what's different about this person, this person who had success, what's different about them.

And I will, compare it to myself. Like, is it something I experienced? How would I react in that situation? Is it a characteristic I possess or don't possess strongly or negatively. And also I run it against other founders who I've gotten to know really well. Maybe because you have so many of these unicorns and exciting stories where you were in super early investing in these founders really before they were scaled at all. I mean, do you want to talk through, were there a couple exciting stories of founders that you backed maybe before others did or before others saw.

Yeah. I mean, um, relish and scale in many more, uh, Angel list. You know, I was the first investor before anyone. I think what's interesting and this is why it's hard to become an early stage investor. The people you meet once they're even moderately successful are very different than who they when I first met them.

Hm.

 And it reminds me of this book, the mask of command by Keegan. It's a military studies book from west point and the lesson was that every leader learns to put on a mask.

That works for the audience. They're trying to speak to that. They're trying to lead towards now some founders are much closer to their original truth, but the other answer is founders themselves evolve through this process, right? They start to change like they realize, oh, that rash asshole behavior is actually works sometimes, but not most of the time.

so they adjust it or that super blunt. Works when it's five people, but not when it's 5,000. Right? And so founders themselves genuinely change. But if you talk to them and they ask you, like, they will tell different Genesis stories.

But it's almost like being a psychologist. If you just threw their dirty underwear out there for the world to see who would want to work with you next year, , and so each of us has investors who go in early with companies. We have to realize we really fundamentally need to understand people.

We need to get to understand these founders and the good ones and the bad ones will all teach you a lot.

Sure.

I think you mentioned, I'm just trying to establish Outlander. I think you mentioned you're going to have like a billion dollars of returns.

 is that true?

Yeah. Outlander one. We'd have five unicorns in the portfolio and scale is a huge And four those we reinvested too. Like that's not a key point as an early stage investor is not just to write the first check, but to actually do the follow on as well. one of we missed that for the five we did , and, you know, scale and Della medley Medimap and head out.

We'll probably produce somewhere between 800 million to $1.2 billion of return. On the twenty-five million dollars invested. we also had a late stage fund, but we did space X and Clover health. And, we did incredibly well with those deals and cashed everything out, you know, and I had the same success on my personal fund before this one.

And it's, you know, the numbers are big. I think you guys are in the same space. You know, the numbers are huge. Like when you hit that, you know, cause our ad I've always been very sensitive to valuation. And so I invest, I'm generally investing in these companies that three to $10 million evaluations.

And I do believe in doing great deals. I like passing on a deal because you disagree on a price it's stupid, right. When it's a great business, but there are logarithmic differences. Like sometimes I meet a founder and like, oh, we're raising them. $30 million. I'm like, yeah, just can't touch that. But we're getting involved generally in single digit million dollar evaluations with companies who are exiting at, you know, Five to $30 billion or greater.

That's the way to do it.

even with, you know, our portfolio sizing, like we're not like YC or 500 startups where we have hundreds, you know, each of our batches has 30 to 40 companies in it.

Right. So when we're able to hit five in a portfolio or the one before. You know, eight unicorns and portfolio. It's like you get huge returns. they will tell you at the end of the day, if all you sit down and do it's just back really amazing people and write the first check to them, you'll be wildly successful. That's number one. Right. But I feel like I learned that business in my first decade of investment.

What I'm doing much better now is thinking about the big picture, I love this industry.

Well, let me talk a

little bit about you at the end here. Um,

 I think I've heard you say that you're a contrarian thinker. No, I, I know I'm quite contrarion. Um, what, so why? I don't know, but I grew up dirt, poor homeless. But luckily my father was a big believer in education reading. So taught me to read and compete at a young age

So tell me about that you grew up homeless, parents were believers in education. What is your youth look like?

my youth was nuts. So my parents were both from the area. My mom was like the black sheep of the family of nine kids. And my father is like an Appalachian hillbilly. So we lived in the back of a car. We lived on a beach and a lot of these stories come from my grandparents who kind of looked out for us, gave me my parents money, as a young kids. But we were just like these dirty little kids that lived in the back of a car. And we grew up in Sacramento because my parents ran out of gas in Sacramento.

So we squatted in this Victorian home on the riverbanks of Sacramento across the river from old setback. just dirt poor. , I mean, we lived in a house with no utilities.

we had pigs living under our house. You know, my mom lived in the homeless camp across the street for awhile. It's like, it was a weird upbringing, but my dad had this fascination with books and I really grew up learning to read and learning to consume information. and it sounds stupid, but the books and the reading, paired with just this brutal upbringing, I think helped me think differently because today.

 I really don't and I never have done what other people do for me. It's like, when people are running one way, I'm always asking why aren't they going that way?

 Learn. I started doing more hardware investments like, if we start catching ourselves saying, Hey, we don't do social media, we don't do gaming or we don't do this. I always find out like why? And so I asked about hardware and I realized talking to founders that the cost of why Dar and the cost of sensors and the cost of systems and the speed iterate around. Had that actually fundamentally changed in the last decade. I think this decade, we're going to see that because the cost of production and the cost of experimentation and the cost of iteration at that early stage has come down so dramatically.

And second thing is software is starting to hit diminishing returns like software, the end of the day. It can only do so much. Can't build a home. It can't dig a hole. It can't do mining. It can't do firefighting. And I think we're at this point and this is a really rough idea. That's not well fleshed out, but I think because the cost of hardware paired with the advances in AI and computer vision and the diminishing returns of software and the social acceptance of devices in public space I think this next decade is.

 Lead to massive impact within our homes and our businesses, where robots are going to have significant impact. And as a result, we're going to see hundreds of billions of dollars of value created in robotic driven businesses Robots are a massive theme for us. And that's not a popular idea for most like what Laura and Blaine and Lucas. And I spent a lot of our time doing is for a third of our portfolio, which has robots is convincing or finding other investors who want to invest after us.

so once I saw you invested in cocoa, but I have to pick up on one thing, Laura is your wife, is that.

a hundred percent. Yeah.

And she's your wife the same last name. And she's your co managing partner here at Outlander?

Yeah. She's, she's a partner.

Almost a contrarion belief. They're working with your wife on a fund. Like have you learned anything interesting how to make that work really well for you

Yeah. You know, Lauren, I, you got lucky. Um, I don't know how other husbands and wives think about it, but ever since we met and started dating and been married and we have a little boy, five months. We spend pretty much every day together. Like Laura and I both fundamentally love business. Like we love creation. and we'll wake up in the morning and we'll talk about portfolios.

I don't know it's luck that it's also, you know, I waited until I was in my forties to get married as well. So I've been looking a long time to find the perfect person.

That's amazing. okay. I'm still staying on you page. I kinda liked the adrenaline. I kind of, I'm kind of an adrenaline person.

but like, I feel like you take it to another level. do you feel that like, do you still reflect on how you like to live.

gets you up in the morning and how you're different than others in that regard?

Yeah.

I, uh, you know, I realized obviously in the Marine Corps, Building a private military company and doing the unconventional work that I did, I don't take risks. That's stupid. I mean, maybe many people around me look at some of the things I do and say, oh, that's stupid. But whether it's going into war or some extreme outdoor things, I've done, I go into these environments where I'm really good at what I do. Right. It's like I go into highly risky investing, but I'm really good at what I do.

 I've engaged in the most unconventional military operations, you can imagine unlocked it by myself. We're very small teams and I'm not carelessly taking on risk. I am taking on a challenge that I know, well, I don't walk into these things, not knowing.

So, I like to compete. I like the thrill of its achievement and try to find experiences that other people don't get to have, or not many people get to have

And so now with where you are, do you get a chance to look back and see. Feel happy about all of your life accomplishments and also like the experiences you've got to have.

Yeah. It's uh, it's insane. I think, uh, yeah, I, I think about, you know, the a hundred plus countries. The, you know, situations and environments I've been in and like, you know, like I had an impact on world events. You know, I've been in the middle of many key events and both company creation things that are part of the history of the world now.

key national security events, like it's, um, it's interesting. I think, you know, it's given me that monthly, I can pass on to my kids, which was something only had as the belief, which. Each of us can have a real impact on the world. Many of us just choose not to do the work that it takes.

And I know, like I had this belief when I was a kid that I would have an impact.

You know, I wrote in my application layer to west point that I would be this great military leader that would fundamentally impact our national security. You know, I got early admission to the sec state. I was studying Mandarin Chinese at 13. Because I saw China as a great threat to our country back in 1987.

 And I followed up on these beliefs with action and a lot more people could have impact, but most people spend the time thinking they just don't act. And that's a common problem in the world is there's a lot of smart people who know what to do. They just don't do the thing that they know to do.

 Okay. I'm inspired to page. Count me, has inspired, a lot of people I think, have that belief that they're going to change the world. And then all of a sudden they end up driving minivans to soccer practice all weekend.

Yeah, you can do both, right? Like you can have both, you can be a mom or a dad and have.

Yep. Okay. Fantastic. . Paige, congratulations on your amazing success. I hope to keep seeing more of you.

Of course, Thanks for coming on the pocket.

Thanks Minnie. Have a great day.

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