good morning, and he'll be up for another home show podcast. Today's guest is Chris Michael, very dear friend of mine, who has had many lives more recently as a photographer before that as a technology entrepreneur and before that, as an aviator for the U. S. Navy.

And you're an investor in there somewhere

on. And we love each other so much that he always interrupts the introduction. Hello, Chris. Welcome. Hello. Now, do you want to say something? I was gonna ask you a few collection when you can

stop. Okay. Well, I'm enjoying this. Incredible T. What is it that we're drinking?

Drinking some Taiwanese. Ready? Okay, it's beautiful. I'm glad you like it. Especially for you. Thank you. And I know it's daytime, so I can give you the single malt scotch, but, um, single martyr tea

is pretty close. Yeah. I didn't know anything like this existed Exactly. You can always tell me

to give you booze in some form. That's true. Um, so thank you for being my guest. I have known you for a very long time, and you know, that doesn't mean we're both old justice. Nowhere incredible yard on duh. And I've always been very curious about weird. What's your story like? How did you get here? I mean, I only know you from your two lives, which is as data for technology entrepreneur and investor and a photographer, mostly other photographer. You know, I think our friendship,

if there is a very do kind of pinpoint, the one thing is around photography. But we met because of what I did in my past life and what you did in your past life. That's true. So tell me about you.

What's interesting? The timing's pretty good for this question. Because, you know, I've been spending the last couple days preparing talk that I'm giving that I think you're coming to on Tuesday at the interval about photography. And I've never really given a photography talked before. And I've seen some good photographers do it, and they usually don't just photographs. They usually tell a little bit of their story. How did they end up in photography or what was their influence? And I'm gonna show a photograph of me as a eight year old, and you're gonna be surprised when you see it, because, Well, first of all, it was the seventies, and I don't think any kid looks more nerdy and out of place than me.

And, you know, I had an unusual childhood, my father's half Greek and have tradition. My mother's Danish American and I moved seven or eight times as a child. And, well, maybe different people deal with that differently. But I think in in reflection over my life, I was always an outsider. Um, I didn't fit in with other people. I lived in many places in the world on, and I found solace and happiness in personal projects. And one of those was technology. So I started programming in 1978 and I loved it.

And maybe it was because there was a piece of technology that I can gauge where there would be my friend and do what I wanted to do. And my first computer was a Sinclair is e X 80 and that started a life of passion for technology and computers and computer science. I was expected that that would be my future, but, um, it didn't work out exactly the way I expected.

Yeah. So where did you grow up like? In a sense, you said you grew up in many places. What? Where did you spend most of your time with bacon? Grease, Father in the U. S.

And, yeah, it's a good question. So I lived mostly in United States in Ellen, away in Connecticut. My mother and my Greek father divorced when I was your old and she married a Frenchman. So we lived in Paris, but mostly different schools in Connecticut in our own way. So I grew up in those places and then went to college at the University of Illinois, which was a really good technology school. But all the technology in 1985 or computer programming 1985 other. This was the National Center for Supercomputing Applications. You know, people were using punch cards. People were, you know, there was that.

It was already the advent of the personal computer, which I had, but a career in computer science then, and how we thought it would be is not what it is today. It's much more social today than it was then, and so I studied political science and joined ROTC because I thought maybe I wanted to be a politician. I had a relative that was politician and was commissioned an ensign in the Navy, then went to Navy flight schools. A navigator just around the time of top gun got the leather flight jacket and spent the next seven years of my life flying airplanes on. Dhe is a navigator and then a mission commander, hunting drug runners and Soviet submarines. When I worked at the Pentagon and had a great time and all the way did a lot of technology, I was not a technologist. I was enable officer,

and so in you, when you grew up in so many different places, did you learn how to speak in many different languages?

Well, my language abilities are not as sort of good as I would have expected. But when I lived in France, I didn't speak English so well. I only spoke French and coming back to that, it's it's It's an interesting thing. Being different when you're younger is not something you want. So I tried. I don't work. This is I was quite young, but I tried as hard as I could to fit in, and I didn't want to speak French, and I didn't want to speak Greek on. I wanted to speak English. And so I've lost a lot of that language ability. And, you know, as you get older, you do realize that being different is cool. But when you're a little, you don't feel that.

Did you speak French when you or Del earlier this year?

Week French? My understanding from my French friends is that my I have an incredibly limited French vocabulary with no accent.

That's

pretty good. That's what I don't know what you'd say. Well, it'll come back to you. I keep waiting for that. I do have an appreciation for French food.

Who doesn't? Yeah. Yeah, Also the line. There's nothing like a great Burgundy. So tell me more about, like, why the the Navy? What was it? I hope it was not top gun inspired. I mean, if I learned that you were inspired by Tom Cruise that I just have to keep

Okay, well, you might want to think about the most painless ways to kill yourself. Well, to be fair, you know, and I'm one of the themes that's probably gonna merge in this podcast is you know, when we ask people what they want to do with their lives, especially young people the only thing that they can oftentimes the only thing they can respond Thio are things that they know about. It's difficult to comment about jobs or lives that you haven't experienced or you don't know anyone. And when we were growing up was more likely. You didn't know about it because the Internet didn't exist, so you could see what you would in the library. Or maybe you were inspired by people you know, where something you saw on television or in a movie. So politics seem kind of interesting to be, Actually,

what was interesting to me was national security, you know, And Top Gun did influence me. It was that was very cool. The movie on dhe, I thought, everything going on in the Soviet Union with super interesting. I was a Soviet studies major in college year. I graduated. It became a history major because the city union Fallon, it became Russia. And I, um, you know, I thrived in that environment. So I went from being a big outsider.

Maybe I was looking for safety in a construct, and when I joined the Navy, it worked for me. I did innovative things in the Navy. I didn't operate like a lot of other people. And I was able to be successful in 11 thing that in life, if you find an area where you're successful, sometimes you double down and keep doing more of that. And it worked really well. And then I worked in the Pentagon for the head of the Naval Reserve. But basically the head of the Navy and I was exposed to lots of people are kind of high level. And having been there, is when I decided, Well, maybe I should leave the Navy and go do something else. And I had never in a 1,000,000 years considered entrepreneurship.

I'm not sure I'd ever used the word. So I'm now at this time 29 years old. I don't think I'd ever used that. We're not finished it Maybe I never even heard the word. It just wasn't in the lexicon of the world that I lived in. And I was gonna go to the Navy, had a program they're going to send me to the Kennedy School at Harvard and from a state college person. I thought, Why this? I get to Harvard. This is the really good thing and on a kind of, um, a kind of lark or a sort of random occurrence. I met a person that flew the same airplane and he said, Well, you really don't want to go to the Kennedy School and got a master's in public policy.

You want to go to Harvard Business School? And I wasn't interested in business. I've never read a business publication. I never took an accounting class. My level of interest in business was zero. I was interested in our security, but this person made such a compelling argument that that would be a good platform. And so basically, I quit the Navy and drove all my stuff up in my old car and moved into a dorm room at 30 or 29 started my first day at Harvard Business School and was the biggest eye opening experience of my life.

So you are really the anti Zucker work. He left the college. You went back to

Mark Zuckerberg, and, you know, I don't know Mark, but I know a little bit about his life. Mark Zuckerberg was an incredibly aware, well aware and at least in areas of business, person in a way that I wasn't. If you'd asked me what Mackenzie was when I was at working in the Pentagon, I would have thought, Well, some Scottish guy, right? I didn't know that it was consulting firm. I didn't know about Goldman Sachs. Things that you know we take for granted today, I might argue.

In fact, yes, a lot more people know about those things today, but many people in the world don't know about them. We just take it for granted, cause again. It's part of the world that we live in. It was not part of my world and home if you had interviewed me and my first day at Harvard Business School, where I sat in the warm deck and I sat next to a guy named Amar Singh, the first seek I'd ever met in my life. So a guy with a turban and Sergio Montes Alva, who's a venture capitalist at Norwest now these two guys I'm coming from navy. I have a short haircut. I'm gonna room with 80 people on an assigned seats and the first thing in the first day. What these two people do is they stand up and salute me and say Good morning, sir.

And, you know, I know that they were kidding, but I felt incredibly uncomfortable out of place. And, you know, as you know, there's a bell grading curve at Harvard Business School. They don't teach anything specifically, it's the case method. And, you know, I'm taking in the county class and I don't know anything about counting, and they're not teaching it, you know? So it was one of the most stressful experiences of my life.

And if you would ask me, what is it you want to do with this degree? I would have said, Well, I was in the military. So maybe maybe I'm qualified to do operations or something. That a company. And then something happened. Business school again change the director and direction of my life.

You know, one of the before we get to that, I want to pick up a thread. You talked about being an outsider. I think a lot of us who we'll find different things to do in life on essentially outsiders. You know, you're an outsider because you don't really have a context. Then you find your tribe or people or a thing a group of people who give you a certain context. And then you no longer an outsider, you're an inside it on something, and then you suddenly have a context. You feel comfortable, you know, you become part of something great. But then if I don't think it's just being in our side and it just is you're like your restlessly curious if that's how you you end up reinventing yourself. That's why you weren't from my I'm guessing from being like a naval officer to business school. You know,

it's like even though somebody tried to tell you, Go do this. There must be something in your mind which you know what I need to change. Change it up like did you ever think about that? Or it was like, Well, I don't know anybody, so I just do

what you say. You're saying a lot of different things, and one of the things is about what is this outsider thing? And by the way, I to me this recognition of being an outsider is something that's happened over time, and I think it's a fascinating topic to put a sharp point on it, though I mean, I was kind of bullied. I was an outsider. I was incredibly insecure. I was weird. I didn't dress like other people I hadn't played. I didn't play any sports. I didn't. I didn't. I just wasn't I mean, maybe my other classmates thought I was fine,

but I I didn't feel that way. I actually thought they probably think I was kind of weird. So I was incredible, like insecurity and what I was finding Waas. I could alleviate some of that insecurity by being good, And I found places where I could be good, like the Navy. You know, I did pretty well in school. I was a B student in high school. I did pretty well in a way, and I was like, Okay, well, I got some success here in some recognition. And then I did well in the Navy,

And then I got some success and recognition, and the one change about going to the Pentagon was I worked for the head of the Navy Reserve, so that may or may not mean anything to the people listening, but basically we have, you know, at the time we have 100,000 people who had regular jobs than on the weekends. They would do the military. And so all of a sudden I was exposed to all of these different kinds of people that had never met before. They weren't really in the Navy, and some of them were CEOs. And so I started to get a different idea about what was possible. And I also had done well enough in the Navy to be around the bosses. So I was around the head of the Navy. And, you know, when you're young and you see your boss's boss's boss's boss and you think,

huh, I'm not sure I want to be that person in 30 years. That was kind of the awareness that maybe I could be on my own program. And, um, you know, I think that's how I ended up at the business school. But, you know, I showed up at the business school with a huge chip on my shoulder and a lot of insecurity because again, you know, I've done well in the Navy. People knew about me in the Navy, or like my little circle. But now I'm trained up in Harvard Business School, and they don't know anything about the military.

I'm like another freak outsider. I mean, there's some other military people. Um, so, um, and how we find our own tracks? I don't know. But I will say one thing. I just learned recently or 22 things. One is James Courier, who's a friend of ours who now runs and FX ran tickle, and we both were CEOs together. You know, he used to say to me, and he's a really smart guy.

He's to say, Well, you know your of this. You're in this world But you're not up to this world, even if of Silicon Valley Tech people, meaning you could be a CEO. But you don't put yourself in the same category as other people, and that's not that I'm in a better category. It's just I'm not 100% in. And, um, I thought about that, and, you know, I was just with I think maybe you met him. James,

Esther Anjum, Esther, who's runs the lens block for The New York Times, and I was at a cocktail party with him, and he said, This is in the context of photographer. He said, I know about you, Chris. He said, You're an outsider observing, and I said, I can't believe that. How do you know this so quickly? I just met him and he said, It's the hallmark of almost all photographers.

And so I think this tribe of outsiders is potentially bigger than we think, and maybe their lives were aligned. In some ways, maybe it is a life of some solitude and observation. I think

the key is in many ways, the idea off off, being an outsider and like people looking for different context and different favors off life is why people take photos like you and I, mostly because it's just like the same thing we four does allow us to observe and try and contextualized the world. How we see it, and that's That's my that. At least that's how I think about these things now. You were in in the Navy for how long? But 77 years, and then Pentagon

400. Okay, well, I was flying for five years, and I was in the Pentagon for two years, and then I went to business school

and you flew all the way, you know, to the stratosphere in your plane.

Okay? No, not my plane. I did that later. I got my plane mostly fluid. 200 feet. So I spent most of my time looking for Soviet submarines. And you know what people don't know. But the number one mission of the U. S. Navy was anti submarine warfare because the Soviets had nuclear missiles that they could launch of the United States in time of war. So they wanted to be able to get rid of him quickly. And then and then a t end of the Cold War. I was in South American Center America hunting drug letters.

So it's like you You were like, what was this guy Tom Clancy writing books about you? What do you like Jack Ryan?

Yes, I wish. But you know, it's funny. I reflect over my own life. I just turned 50 and I'm unfortunately, unfortunately, I wasn't a photographer then, but I I'm really lucky I got to do some really cool stuff. And, you know, a lot of people talk to me about that. My military service and I don't want to overstate this, but a lot of people say to me, you were in the military quite surprised, and then a little bit of, um it was everything OK at home,

maybe, Maybe like they thought of the military as a place is an okay place for somebody with no options, Like a place to get help in your life. You know, my view was it's an incredible experience for young people. I mean, I never had to shoot at anyone. Unfortunate. I never went to Iraq and Afghanistan and uncertain that warfare is horrible, but other than were fair. It's a great place to have to learn a lot about leadership and to be part of a team of people doing cool stuff. And, you know, when you're 25 years old, leading a team of 20 people is a cool thing. You learn a lot about yourself and other people.

And what what were the big lessons from your time in there? In the military?

You mean like leadership lessons,

like Like what? All did you learn there? Like I know you talk about how would help you, you know, figure out a lot of things in life. You flew all these planes and he worked with all these people. But what is that? You you walk away from that that professionals late. Wow, this is what, like version 2.0, of Chris is exists because of

the army. Well, I did maybe. Well, you know, you're not alone in that, ever. My apology? No, no. Everyone says that. Particular people from other countries, I think they that's the general term for the whole military. Well, I don't think I could have answered this question at the time, But what I've what I've learned now and this isn't in juxtaposition with having been an entrepreneur in a board member for a long time is that the rewards that really matter and our lives are not financial rewards. And I know people listening or like Well,

that's obvious. But I said on all these competition committees and everyone's talking about stock options and people talking about making a lot of money in these companies and pay and and in the military, you know, nobody gets paid any more than anyone else at that rank. It's not like you did a good job and you get a bonus, right? And what I found is that people are incredibly motivated. They work all the time. You know they'll do whatever to accomplish the mission, and the rewards are all psychological. The rewards are recognition that you've done a good job. The rewards are maybe that's a metal or certificate. The rewards are a sense of camaraderie in a sense of mission and these things where you could get people to fight in in the mountains of Afghanistan, where they're getting shot at every single day and they're freezing to death and they're not complaining, and they're working super hard and they never talk about comp. There's an important lesson around humanity here,

and this is one that I think where in many cases, American business, her global business has lost its way. We spend all of our time. A comp committee is talking about how to reward people financially, and we spend no time talking about how to reward people emotionally. And I think it's the emotional rewards that matter.

That's a funny you Bring that happen whenever people talk about universal basic income in Silicon Valley, I'm always reminded of, you know, fashion designer Bruno Cochin. Eli's comin tech more than food managed dignity, man being Are you operative word for every human being. That's how he used it and I think a lot off a new talk about basic human on the universal basic income. You forget that the sense of, like achievement, the pride like the mission. What is it all about? It can't just be about money. Now, you look at where we are in society. It's only about money right now. Even in Silicon Valley, like you feel more and more people are reflecting on how much money they're on a mirror rather than how good they're going to do. Yeah,

well, you know, this is

I don't want to sound like an old fart saying this, but I do believe getting riches should be a reward. And it should be an outcome off a great mission off being part of something bigger. It can't be the sole reason to

do so. I might argue that it matters a lot less than people think. And I know people know this on an intellectual level, we know we're dealing with pathology of humanity, and the pathology of humanity is this. You need to be safe and to have to be recognized and you know, to feel like you're winning and feel protected and, you know, and I think we have to be careful because in a world of abundance or lack of abundance, we can engage in a bunch of activities that are optimizing for these proxies like money and miss out on the things that really matter and you know anymore. I mean, I find few things more offensive than somebody saying they made $80 million on Bitcoin and they're all set in life. Well, their journey has just begun. You know that journey does not get solved, and it never gets solved through money. Look,

if you don't have enough, that's a problem, but at a certain level. And we know we've all seen the research, but we spend no time. We spent no time trying to get to the right place emotionally and spiritually. People are reading about meditation. The 10% happier rule, these air, all hacks Look, the bigger picture isn't You're not gonna life hack your way into happiness. You're gonna get there through a deeper and philosophical understanding about the things that really matter and money. Just money distracts us. It also is important. And I say this stuff because it probably a lot of leaders listening to this You know, I hate to give you advice,

but we should be spending as much more time on the psychological well being of our team and our families and our friends than we do on all of the other things. Or maybe more. You know, I think about my girlfriend who works at Instagram, and, you know, when her boss or one of the founders says to her, You know, you're doing a good job that means more to her than her bonus or anything. It means a lot. And you know, when you walk by some somebody in the office and you're the founder and I have been the founder of two companies and you don't say hello or your little you know quick with someone, you don't realize the kind of effect you might be having in their lives. You've missed the opportunity to make a big difference in someone's life. And you know, I have low tolerance for that.

When we lead other people, we have an obligation to those people. And, you know, this is what I learned in the Navy. I didn't learn it while I was in the Navy. I learned it having run my companies and observed a lot of things in a lot of businesses, and I learned it for what matters to me. You know, it's it's friendship and respect.

It's also, you know, have sex. You understand? All of everybody understands that. You know, it's it's a matter of life and death if you don't depend on each other equally great. And I think a lot of that is a good lesson. That's pretty deep talk right there. So you go from this in a more egalitarian if a place where you know, everybody knows how much you make, like how much everybody else makes. And it's all about about like, you know, working as a team and working together, moving together.

Maybe it's about a life in service

to other people. Yeah, and then you come here. It's a living, really, which is very different. That's very individualistic to, to say the least, right in the sense that the motivations are different. People have a different way of thinking about things. Why do you come here? Why did you come here after your Harvard business school?

Well, I should say that the context was first your business school. I don't know what I want to do. I'm getting D program from this experience and military where that's all I knew. And, you know, a lot of people went there from, like, McKinsey or baying, and they knew a lot of stuff. They knew about business. I didn't. So I was learning a lot of things in the case. Methods. Good for that. But I had a transformational experience that I mentioned out. Just say quickly.

A guy came into our class named Dan Bricklin. You know, Dan. Yeah, yeah, yeah, this got So Dan shows up on a class, It doesn't look like anyone else that shows up in Harvard Business School. He's got this flannel shirt and he's got this scraggly beard and he talks about building visit cock and you know, he was a student there and he wanted to do spreadsheets differently. Basically, he takes us through this long story. The net part of this in the net result of the story was he didn't make that much money. But what he had done it was create something that mattered. And as he looks back in his life, having created something was the currency that gave him a sense of purpose and meaning in his life.

And it was in that moment that I realized that what I wanted to do was to be an entrepreneur. So I was then thrust into this stressful position that a lot of people are languages. I want to be an entrepreneur, but I don't have an idea. And for my best friend in the world is And Wayne is a partner at Village Global. She was in my study group at Harvard Business School on Dhe. She got a job working for Paul Allen at Interval Research Corporation. And so let's go to San Francisco and I went to San Francisco working for consulting firm and learned a lot for my 10 months there, but really want to start a company and had the idea for military dot com in 1999.

Concerning for him. Please tell me it wasn't lying or something.

No, no, no. It was like a small strategy way. I went to them to captain build military comedy like Well, you're going to pitch us tow. Why, you should pay us $5 billion. Hi. Good.

It's funny, you know, like how

the cookie crumbles. Yeah, a lot of cookies.

Uh, s So you come to San Francisco and, like, 99 98. So how was it?

Well, I moved into the golden Gateway.

I like

everybody else like everybody else. And, you know, I was in the consulting firm, and I was trying to find this business idea, and I triangulate cause I was doing the reserves, and I was, you know, um, my love of technology put me in a good position because I knew a lot about at the time a lot about the Web visa. The lot of other people. I was young and I was into it, and I knew about good product design, and I'd use some early social networks, and it really hit me that the military was, ah, great group to connect on the Internet.

And, you know, that idea was basically Facebook, you know, like, five years before Facebook. We weren't the first person have an idea of an online social network, but it was super early, and basically the product was quite similar absent the feed and absent viral videos which did not exist at the time. And so I, um you know, try to raise money, and that was very difficult to raise money. Everyone says, Well, there was a lot of very bubbly and that's true,

But a lot of people were trying to raise money, and at the end of the day, I ended up raising $5 million from a field, and then we raised another $20 million. And in March of 2000 we launch the website and also three other Web sites, including one by Ross Perot launched, and it started to get problematic. And then the bubble burst. I want to go through all this stuff. But, like I cut expenses in the company with 33 lines, way offs and things were going badly. I essentially get fired. And Abigail Johnson says two men they hire a new seal, gray haired CEO because at 32 I was too young to run a company. They have her gray haired CEO and he takes over and it turns out things aren't going well for him either.

And so I'm on the board and we're gonna shut the company down. And our mutual friend, the PR great Abigail Johnson, says to me, Well, if someone's gonna shut the company down. It should be you. And so I had a board meeting say I should come back, is the CEO and I come back and we're basically out of money, having raised all of that money and and Dwayne sells an advertising contract that keeps us going for two more weeks. And essentially we turned the company around, would be akin to flying a 7 47 nose down into the ground and pulling up with the tail section no longer attached. And we turn the company around and I was able to sell the company. I mean, that, like 62nd Vignette,

was the singular, most important business experience of my life that occurred over three or four year period, and everything I learned in business did not. I did not learn in the Navy or a Harvard business school. I learned by making an incredible series of mistakes and having the opportunity to recover from them.

Oh, so did you at least have a good time in the late nineties? In

the bubble? Really, Really. I was working. I mean, I didn't have a good time. I was so committed to delivering this company, which was really about connecting people who served to their benefits. And it was so hard so quickly that it was based. I was basically in, like, my own Vietnam. I mean, you know, and and I work 24 7 We did everything to make this company work and way did make it work. And, you know,

military comets still around today and there are too many Web. 1.0, cos it around today. But it required everything I had and more. And I think today I'm still affected. I have, like, some PTSD from experience and, you know, and that you know, this is to me. Oh, the reason that big companies can't innovate like little companies and not all little companies can innovate in the same way is there are some companies in These are entrepreneurs I like to invest in that will make the company successful. They will not fail. They will do everything you know, everything that's required.

And that's you know that's the hallmark of the Navy seal to its they're not always the toughest people in the world, although they're pretty tough. They just don't give up and, you know, and I didn't give up and thank God it worked.

You know, I'm glad it did for some of those ding works, right? So Well,

you know, we've all but we've all been there. And, you know, the mistakes I made are profound. And the lucky thing I got to do was reflect over those mistakes and get better because of

that. So what did you do after military dot com?

Well, there's two parts of after military come. One part was when they hired that professional CEO and I remember going into my office back then, we had offices, you know, CEO and my office had all this military stuff on the wall, and he's sitting at my seat and I'm in the guest chair in my office and he says, You know, Chrissy be better for you not to come by the office anymore. And you know, I'm speaking for somebody who was incredibly insecure, who only had no money and everything to me and my entire identity. Was this company to be basically told that you're no longer welcome to come by, was the biggest gut punch of my life. And so what I did is I swam every day for five months thinking about how I after, and that's where I learned was able to evolve. I came back.

We turned the company around a couple years later. I've been trying to sell the company for a dollar. We owed all of this money to a lot of people, but the company started to better and better. And the CEO of Monster essentially bought the company. And we figured out a business model for military dot com. And I said to him, Well, we could do it for you for military people, So think about like Vertical Facebook and vertical job Search. Well, maybe we could do it for nurses and teachers and police officers and government workers and motorbike riders and venture capitalist give all these vertical communities. And he said, Let's do it And I went off to do that inside of Monster with a special deal. And then and he got in trouble with stock option backdating. He's a good guy.

I just got caught up in that scandal. They said they weren't gonna fund the company. We just got it responded out and got it funded by Trinity. So I started that company and that we put the lessons. I didn't make exactly the same mistakes I made before that. The company was a great company called Affinity Labs, and I sold that. And then that took us to 2008. And that's the big moment where I decided what it is I really wanted to do with my life, which would be my third career.

And so affinity Labs is very you knew folks from, like folks like James Career

No, from Bill from military. Because when I sold tomorrow, well, James was a year after me at Harvard Business School, so I kind of knew him. But when we sold military, Andy McKelvey was great CEO. I was like, Well, what other companies should we buy? And they've been talking to tickle. So we bought. I mean, I didn't but monster but tickle And, you know, with Tickle Cane,

Michael Birch and James Courier and stand Danowski, who are my brothers. I mean, these people are very, very close to me because we went through this experience together and it's a great batch of people, you know, And I mean, you know, look at that group. It's ah, cool group

of people Yeah, it's funny. Like, you know, you don't talk about it. Network effects As much as those guys don't

know, they love network effect. I talk about aperture

on, but I know just which is rare. So what was the biggest lesson for you off your up and down journey and an entrepreneur? Um, like just one less like like I have. I have three, but I can show, you know, like, for instance, you can share all three Just like you said. From your mean lesson from from your Time at the U. S. Navy was, ah, higher purpose, the sense of mission and looking beyond what is the monetary compensation,

which is a proxy for success in society? That's a huge lesson. If you learned that as a 27 year 28 year old, I mean, she's like you already won like the large tree of

life. I agree. So that my lessons, you know, I I've given this talk. I talk on businesses, lessons from the edge. You know what the three or four things that I learned in military dot com that, you know, help me an affinity labs and help me with my company's But if I were to triangulate on one, you know, I'll tell you what those are. One of them was I confused activities and outcomes. So I heard PR firms and I did all of this stuff that you're supposed to dio and you know those things. You know, a front page out of the New York Times doesn't necessarily delivering our front page article. New York Times doesn't instantly deliver an outcome for your company.

You know this better than anyone. So I made a lot of mistakes, and you can make the activities and outcomes mistake very easily when you're overfunded. Oh, we need a car. We need a logo. We need a great office space here. All these things that seem reasonable. But do they really matter of your company when you run out of money? You know, it's funny what you focus on what matters. I learned a lot of lessons relating to the right kind of team culture, you know, and that is, people know this a lot. It's a little bit like the radical Transparency book,

but I had a lot of people in the company that we're really, really talented or had some people company really counted there were also culturally problematic, and I also had some people that were very nice that weren't contributing as much of the company. And I didn't always have the courage to deal with that and to build a culture of excellence and trust. And, you know, that's a mistake I will never make again. But the most important mistake and the most important lesson is a personal lesson, and that is my insecurity, maybe for my whole life, but manifest specifically as a 30 year old CEO, which was very young at the time and is now considered old but was that I had to be right and that I had to show that I was better. And, you know, I'm pretty good at product and I'm pretty good at a lot of things, and what I didn't focus on was my own vulnerability.

And I didn't focus on really building this culture of trust where people knew that I had their best interest in mind. And once I once I made that transition and it took me a number of years to make that transition. It's amazing what's possible if you trust people right, so at first, and my first manifestation is the CEO. When I would get people feedback, I'm not sure that they took it very well. I just didn't It didn't go over well with people later on. You know, I think people knew and for good reason that I wanted them to succeed. I really mean this was, in my heart, their success. And once you make that transition where you could be vulnerable and you can talk about your mistakes and you can work on helping other people be successful and including maybe having them leave the company because that's in their best interest. Um, if they believe that you unlock a whole nother level of performance in a company,

I told everyone in new hire orientation guide affinity that one day you will lose passion for the company. You'll lose passion for the company because a something's frustrating you in the business or B, you're just over it. So in both of those cases, come talk to me because in the first case I might be able to help you like I'm able to say, Well, that is screwed up. Why are we doing things this way? You know his company's get big. They start making mistakes or doing things that really frustrated more junior people. They don't have control. The second is everyone leaves their job. It's okay. And when that happens, I'm gonna help you get another job. I'm gonna help you as much as I can.

So once you everything becomes okay to talk about whether I want to be in this job or not or whatever it might be because I recognize that this isn't a one off transaction, our relationship goes well beyond true ventures or goes well beyond. Getting home goes well beyond any magazine you write for the best relationships do. It's not about the specific entity we're part of. It's about the friendship. Well, I think

there is. There is to treasure in their arrogant treaty. Your lesson. I think number one you're saying is like if you're not true to yourself for anyone, actually, I see what a good day I was funny. It was like, But what I mean is like, if you're not honest with with yourself, Oh, are with the people you work with and in your communications, you're always going to be on the losing side. of the equation, right? And the second thing, which I I take away from your this thing is that you you actually have to stop thinking of life as the transaction. Yeah,

and like, how do you preach that lesson? In a world, especially today Silicon Valley, which is entirely transaction driven, the more and more people are doing like relationships are built on transactions. They talk about companies and ideas as deals. And, you know, it's like somebody's dream is an opportunity for them, like, Why are we talking to them like this is an investment are this is a deal that is just such a brutal way of describing somebody's, like, big idea?

Well, you know, I don't think, you know, it's It's not

just my philosophical way of thinking about is that you're

different. Yeah, well, it's easy today to see all the negativity relating to money and deals and transactions, but, you know, there's a lot of positive, too. I think people are more comfortable with me more vulnerable. I think that there is a lot of venture firms. When I was raising money for military, it was sandhill road. It was all white dudes that were incredibly rich and they were nice people. There's something I'm not being This isn't a negativity, but they were financial investors. I mean, yes,

they might be friends with some of those people today or many of those people. But today we have a lot softer, softer, gentler, relationship driven set A veces you know, I think that spark capital. I think about your adventures. You know, I think about my friends, a trinity there, people there that are nice people that want to have relationships. People and entrepreneurs have many choices now, right? I mean, I'm not going TV, you know,

when I was when I was younger, everyone is afraid to go to square right, because it was a view that it was very transactional. And, um, you know, today people have a lot of places. So I would say there's more openness to a lot of these things. How do we change it? I think the few ways we can change it is one talk like this. So people know help younger entrepreneurs, you know, I think honestly, board members in Silicon Valley, in my opinion, are not doing enough to help entrepreneurs triangulate on the right cultural approaches to building companies. We will leave it to them to come up with it. And then we get upset or not upset, depending on how it works out. It's not that hard.

I mean, that's what I'm saying is transaction or Inter thinking right? Like everything is an investment. Is a timeframe attache where they make money moving on? Yeah, yeah, yeah. But in the sense, like what I'm saying is, like, you know, you wouldn't Even as an investor, I meet all these young founders, and I love meeting them because, like, I love the ideas and the energy they bring to the table, everything is being driven to.

Okay, you have to make a decision. And like this 10 year journey, we're gonna take in 45 minutes, houses I like. Do you not like think about that as an issue, like making how we build, you know, great businesses and ideas. I mean, I'm not sure if the cover guard his initial check like on, like a 45 minute conversation, right? I know the Twitter guy had their work cut out to

Yeah, well, it's a it's a complicated, you know, there's many threats now open in this conversation, and it's complicated.

That's what I do.

I know. Well, I I'm gonna say something provocative. And and that is, I think there's been a broad based application by boards of directors in the country area, maybe even the world. Generally, a lot of board members are just there to have lunch and get paid. But in Silicon Valley, the application is if the company's doing well, there's product traction. The board members stay away and you know that's what I wanted is a CEO. I didn't want my board in my business. But honestly, if we believe that we all have an obligation to a broader society and two employees product traction is not sufficient t to say that your company is being led well or lead ethically, and your team members are taken care off. And if you were a board member and you were there while these things are going on and you know we can think of lots of company examples here, you're complicit. You know, I think we have to. We have to require good ethical moral leadership in these companies,

agreed. You you would not have anybody human from me on this. I've been writing about this for the longest time. I think Yahoo is as much a problem off the board. That has hard then then the management. Every decision of board has board should like I think self accountability and boards and in general in society is gone. Going away. It's like, Is that what I was talking to? Somebody yesterday? It's like he will keep complaining about Facebook and Twitter, and it's like But we're the same people who are the people who are going There were the people who are making nasty comments. It's not like somebody some machine is making me write the nasty comments like Don't go take, they be self accountable and just stop using You know, Facebook. That's the best way to deal with the damn problem. Anyway,

let's talk about the more fun. Okay, there's three years here life. It's like as that photographer on DDE I'm getting You do want to talk about that a lot. I don't quite know how you became a photographer, Um, because I turned

out to be a bad investor.

Hubbard. Why did you become a photographer?

It's a good question, and you know this is on my interval talk. Like if you had asked me, uh, any time until, like, 15 years ago when I become a photographer. The answer is no. I can't. The earliest photograph I confined that I took was in 1987 and I was in the Navy, and I don't know even how I got a camera, but somebody gave me a camera. I took a picture and you'll see the photograph. It's okay. Photograph. Everything looks kind of cool when it's vintage film, you know,

But I wasn't that into it in the Navy, I took no photographs, really a shame, because I got to do all this cool stuff. There's a guy named Asleep Ma GED, who is my VP of engineering at military dot com. And he's a photographer, a great photographer, And he gave her he had this really nice camera when I was running military coming on like you're an idiot for spending $5000 on a cannon. One d, you know, And then I started to take some pictures of my point and shoot, and the pictures were pretty good. And then more pictures and the pictures seem good and I started. And you know, Social Media is going out at the same time,

so I'm getting positive responses. And so, like a lot of things in life. If you do something when this happened many times in my life and you're getting some positive rewards like I take piano lessons or did I never get positive rewards for my piano lessons? Because I'm so bad. But with photography, I was getting more and more positive and it felt good. The rewards were there with the imagery, and I started doing it more, more seriously. And then after I sold my first company, I started to travel more, and I traveled a lot as a kid, and I realized that my camera was that magic carpet. It was the way for me to engage in the world. It was a way for an outsider to be an insider,

and there was another byproduct, and that was that was great joy, not only and having those experiences capturing the moment, building little products, your product person, each photograph is its own product. But the great joy was to photograph all of my friends in Silicon Valley and many people you know lots of famous entrepreneurs. I'm not famous most alive, but not all of them alive today. And to give them portrait's that mattered. And my portrait's ended up being used by many people, and that felt good, too. And so all of a sudden I wasn't and this has been a theme. I think my whole life I wasn't like everyone else, like I wasn't an investor.

I was really a photographer, but did some investing. And so that's the Maybe that's my approach for a living, which is to not be in an easily comparable the living, easily comparable life. Like I'm not gonna be on the mightiest lister. I'm not going to be the top, you know, 30 under 30. I'm my own person, and that person has a kind of portfolio of things. So photography has been, uh, great joy because of the things that's allowed me to do. It's made me recognize that memories of the currency of our lives and how short our lives are, and it's also a challenge.

That's the hardest challenge I've ever had in my life. I mean, to be a great photographer and to do really good and important work is really difficult. It's way more difficult than getting funded In Silicon Valley, everyone's a photographer. There are a lot of people taking pictures, and I, um you know, I'm still in the novice category. I have a lot to learn, but my journey has changing. And just this year I'm starting to teach. And I'm starting to think about my photography as something deeper around storytelling and capturing memories that might matter to the historical record. So that's my objective. And but mostly it's really, really fun. And I get to hang out with my friends like you talk pictures. Well, I think the

language I enjoy about photography and a lot of my photography efforts are because if you like, I will. I was just that guy. I think there's two people who are responsible for me. Picking up the camera and being facetious of ordered run is Vincent La Foret, and the second is you, and both at the same time. Both of you pushed me at the same time.

I think it's very

for three years ago and get going. We shut down. Um, there was definitely an emptiness in my life, which I play It's hard to describe like it's just like your child died and I needed to do something. And I think photography creates. This gives you this tool to kind of do something, and I agree with you. The positive feedback loop is very much like writing a block. Coast is like get people like you. They don't like it and they were times downer. Time's up and it kind of has its its own merit. And I think since then it has become a journey for me, like just like it has become a journey for you has become a journey into my own into my own self, into my own passed right. And I think when I think about you as a photographer, I just think you started out in the U.

S. Navy of the guy who found a future and a path by listening and, you know, you know, looking for the mission in military dot com, you found the mission to make other people's lives better. And now, with photography, it seemed like you take portrait and give them back to people as a reward for what they have given. Yeah, is that a fair,

says That's a fair assessment, you know. And it's funny because, um, we were just on that catch, like voting and the board that I'm lying. And there's all these great photojournalists that Aaron, um, National Geographic or they write for The New York Times. And, you know, I've done some of that work and I've been published Not as much a national deficit, I'd like. But what I realized is that I am actually a little different in my photography. And the great joy for me is to give people pictures of themselves are of moments that matter to them. I love photojournalism, and I'm trying to be a better photo journalist.

But you know, the real joy is that you know, how important is a photo of you with your family or you doing something? You know, when we went together this fall? Bart, I have incredible photographs of you, which at the time, and you know this is the This is the marvelous thing about photography. And, you know, I can't think of anything else that has. This quality is I can take an average photograph of you standing with your tripod, doing another long exposure, and small part, and every day that photo gets more valuable.

I look at that photo today, and I get kind of choked up when I see that photo. It's a really meaningful experience in our knives. All photos have this capability mean if you take a crappy photograph, well, maybe it could be valuable because there was no other version of anything like that. But you've taken reasonably good photograph with soul that becomes incredibly important. I mean, how important is that photograph? Is it a $50,000 federal office at 100,000 off? It's a priceless photographed, and I'm not being not exaggerating these things. It's memories that matter. It isn't the $60 million in your bank account or the $5 in the bank account that has its own purpose, but meaning to me. Photographs represent our lives, the moments in our lives, and that is what matters most. I think

the gift you given me is the fact that when I'm gone, there is an archive of me living on the Internet. Like my family will have access to that in, you know, in crisp, clean black and white photographs, right, or the fact that I will. He ever My God daughter will grow up And then I will be there at that time and she will see herself her first day out and into the world. Waas. And she's in my arms and my book that Yeah, like that's

an average moment that took two seconds.

Not an average, right, but it is a

lifetime. Yeah, you're right. Well, I don't want to be too negative or too pessimistic about the photography, but, you know, having just turned 50 even this week, I had to people, but I did Full portrait. Syria's with pass away. And those photographs are used in their lives and their printed. And, you know, this is this. Why encourage maybe anyone listening here? You don't have to become a photographer,

but pay attention to those moments and take those photographs. And don't just keep them on your phone, put them someplace, print them or put them someplace where another generation confined them. And you're right to say I mean my own. My, um, portrait. Siri's is, I don't know. It's 60 60 photographs, 100 photographs. They're good photographs and they're important photographs. And it's funny. I was just working on my will and one element of my will is to provide a trust that will keep all of these photographs alive beyond my own life and because people want them and they will want them and they need to know about them. So I don't know. It's the least paying job I've ever had in my life, but maybe the most rewarding.

So I think we've talked for a very long time and, uh, we have a few more minutes to go, and, uh, and when I ask you this very personal question in 15 plus years of photography, hundreds of cameras and lights, it is and equipment there. What have you learned? Like, What is it? What is the great Chris Michael portrayed? How does that happen? Is it because of the camera is a cut of the lens? Is it because of the photographer is because of the subject? What is it like? What is it that makes the picture You make

courage and hurt. So I approached my photography with an open heart and with excitement, enthusiasm. Thio capture that moment and that could be, you know, I just came back from Antarctica. Could be working hard to go climb some mountain to take some pictures, but mostly it's, ah, warmhearted engagement with another person. And you know my purchase. I think often and you know you can tell me because you're getting photographed by me all the time. But we're having a good time. We're laughing. The photo is part of the conversation. I'm not just they're taking your photograph. We're having some funny conversation,

and part of that is taking the photo. So it's an interesting thing, I think, some photographers lying people up in the studio and they tell them to shut their mouth. And I like, you know, do whatever None of my photos are like that. All of my photos are a funny, interesting or poignant moment that we're having together, and the camera just is there to capture it. So maybe that's one of my big takeaways. The other is gear doesn't matter. And, you know, most recently, in the last couple years,

I was inspired by Sam Able, when we've talked about a lot of great National Geographic photographer and you know he's shared with me and not just me. A lot of other people techniques for all of us to be taking much, much better pictures. And, you know, those are very practical pieces of advice. And if he does get into the heart and the soul and the philosophy of the photographic life, which is important but things like, you know, make every photograph the best photograph you can. And people listen here, who maybe don't take photographs. I just asked when you take your iPhone picture, are you taking 1/2 2nd to take the photograph? Are you taking 10 seconds?

Take the photograph or 30 seconds or two minutes or five minutes Because, you know, if you take the time, the photograph can be great. It can't be. It can't always be the best photograph, but it could be the best photograph. You could make it the time. And you don't need a 1,000,000 photographs. You need one good photograph.

Hey, you know, Samuel, Say's come

close and wait. Yes, Very. Yeah. I love that.

That's your

life. Yeah, you're right. If I was to write a book, maybe it would be called composing. Wait.

Oh, that was, uh, pretty emotional conversation with you. A lot of things I didn't know about you. So I can. You can no longer be called the International Man of Mystery because the mystery is some were gone a little bit. Thank you for sharing your life story with us and especially those lessons in being who you are. Thank you, Chris.

That's not around.