Builders and Innovators: Conversation with Chris Michel
Cloudflare CRO Chris Merritt interviews Chris Michel to discuss his experience as an entrepreneur, investor, and photographer
All right, and we're live. Here I am today with Chris Michel. Chris, we've known each other for, I think it's about two decades, and this is just a real nice time for you and I to reconnect.
It's great seeing you. So over the decades, you have had multiple careers, but I just have to pause and say, it's making me feel bad when you say over the decades, you know, we all knew this time would come and now it's here.
And that just means that we're old.
Well, there are there are a lot of photos of archived of you and you can see that you're not aging.
So it's great to spend time together.
Are you buying today? Yes, I am. So the like the overview, if I were to say what's Chris today, you're a photojournalist now.
Yeah, which is, you know, that's that's different than the context I met you, you know, decades ago.
And if I look at where you you've spent time, you've obviously spent time, you know, photoing North Pole, South Pole, Papua New Guinea, really interesting places.
But the one that's that's like, I was so shocked to see as I was going through and sort of catching up was on a spy plane.
Like, I didn't understand how that happened.
Yeah. How did it happen? Or what is it like? How did you pull that off?
Well, I have to say that that was the best and worst photo assignment of my life.
And I was actually giving, you know, so I started this company military.com. And a lot of people, I don't know, we have still around today, 20 years later, and we maybe have 15 20 million registered members.
I don't know how many are active now.
I'm not at the company, but but a lot of people. And for a long time, I would give speeches about leadership and innovation, you know, because we were there at the beginning of the Internet era.
You know, this is a web 1.0 company bringing it to the military is 90.
We started in 99 99 Internet, you know, I was around in 94 monster, all those people.
Yeah, we thought we were late. But turns out we were early, you know, depends on how you look at it.
And I was giving the speech about innovation.
And this general comes up to me and he says, if you give a speech at my base, I can get you a flight in a U2 spy plane.
And I said, Well, that are they even flying?
I mean, aren't they secret isn't, you know, and so it turned into a big story that I did for the Naval Institute.
And it's those photos have been used a lot of places.
But basically, I did a week of training got fitted for a space suit.
I mean, this is I mean, it's not space tourism, because it's the military. But it's as close to being in space as you can get without being in the space station.
So I was the 11th highest person on the planet, the space station astronauts were higher than me.
And how many feet like what's that measured in? Where were you?
Comrade, you have a lot of questions about our military technology. I was above 70,000 feet.
And that you've not been prior to that 50,000 where I mean, you're a naval aviator, we're gonna get into your we're gonna get into your history.
Well, I flew p3. So I maybe I probably the highest I'd ever been probably was in a commercial airplane, maybe close to 40,000 feet.
Okay. Okay. So you but it's 70,000, you know, you have to be in a space suit, because if there's any kind of pressure loss, your blood boils, it's, you know, which is not the best.
And, and, you know, you do see the curvature of the earth, and you do see a black sky, and you get the overview effect.
But it was the worst assignment, you know, when I landed, I mean, it's this incredible experience.
I mean, it probably cost the taxpayers, you know, quite an incredible amount of money.
But when you land, you know, that you land, the airplane falls over, because the landing gear drops on takeoff, because every pound is like 10 feet of altitude, you know, they wanted to go.
And so the plane lands, it falls over, they attach the gear, they pull up to base operations.
And you know, this is a big deal. It's like a space launch for the even for the Air Force is a big deal.
And there's the general and all the people and they're saluting the airplane.
And there's my name is up on this giant billboard.
And they come up to the aircraft, they put this little wheelie thing, they open the hatch, they pull my helmet off, and they hand me a bottle of champagne.
And I sat there shagging champagne in the back of this U2 spy plane.
And I thought, Oh, my God, it's all downhill from here. This is it's certainly turned out to be true.
Well, like what you just described, I characterize you as a bon vivant, like somebody who what's Chris up these days?
What's Chris up to these days, I get questions when we run the people that we know.
And I'll say, Well, he's just traveling around taking photos.
And like as an end destination, that really doesn't pay much, like much respect and honor to you came out of the University of Illinois, you flew for the Navy, you went to Harvard Business School, you found in and told sold two companies, I would argue you sold the same thing twice to the same company.
So we're going to unpack that in a moment. Okay. And then and then very insightful.
And then you have this career of like all these things that you find interesting, like commercial pursuits and venture, you know, academia pursuits, and you spent time as a fellow or at least on campus at HBS postgraduate, spending time with entrepreneurs, photojournalist, you're also a Leica ambassador.
I mean, sort of, well, okay. So I don't exactly have an ambassador program, but they did fly me around and give me cameras.
That counts. That counts like in my book, you're an ambassador.
So as a relate, like you're the arc of your career, it spans a few phases.
And I'd love to just sort of unpack how you how you sort of navigated that.
And if you look back, it's almost like, if you're the photojournalist, looking back at your own life, like through the lens back through the lens, how do you think about those transitions?
Well, it is interesting, you know, when we look back at our lives, it's, it's, you know, if you did something quite different, you wonder, well, was that was that me?
And somebody was asking me about my experience in the military, which I loved, you know, I flew, I flew as a navigator and mission commander.
So I was like Goose, not Maverick. And I hunted Soviet submarines.
And then I worked on the staff of the Chief of Naval Operations for the head of the Navy Reserve as an Admiral's aide.
So I got to meet all of these interesting people.
And then I, you know, ended up at Harvard Business School. And I if you'd asked me when I was at Harvard Business School, what, by the way, before Harvard Business School, I would never have been interested in business, I went there kind of on a lark.
And that's not normal. Most people don't have that access, Chris.
Well, you know, I honestly, I think it was my military service that, you know, and I saw the movie, The Paper Chase, which kind of got me excited about going to an Ivy League school.
And, but I never would have said entrepreneur, if you'd asked me at any point up to that point, what what I wanted to do, I wouldn't have said entrepreneur.
So it wasn't in my, it wasn't in the menu of things that I was thinking about.
If you'd asked me my first year at HBS, I would have said, I would have tried to extrapolate what I did in the military into a job like, okay, well, I flew airplanes, and I'm good at like leading people, maybe like operations or something.
Right? I don't know. And I do think that this is a little danger for all of us, which is, we put ourselves in a box, you know, maybe the box you put yourself in right now is in sales, right?
And are you a salesperson?
I don't know. Well, that's what you're doing right now. And doesn't mean that that's all you can do.
And I don't know. Anyway, this has been a theme throughout my life, but it was a long time ago.
And then I did those two companies, and they were very difficult.
Well, the first one was very difficult.
And then the second one was easier. Well, so let's, let's, let's, let's pick on that one for a second.
You say you do you do these companies, you come out of HBS?
Well, actually, I should tell you, I mean, I think it's interesting to note, because when, when I think about giving these interviews, I'm always thinking about people that might be listening, and I'm hoping to give them something, right.
So the thing I'm hoping to give people listening is that if, if maybe they're thinking, if this guy, Chris can do it, I can do it too.
And by the way, that idea is much more pervasive today than it's ever been.
Meaning, in 1999, I was 30 years old when I started military.com.
And I had gone to Harvard Business School, and people thought I was grossly unqualified and very, very young.
So one thing that's changed with Mark Zuckerberg and other people is, you know, a lot of people don't think it's odd that your first job is a CEO, is as a CEO.
So those role models do exist.
But, but That's a pattern here at Cloudflare, no less.
Yes, exactly. And you know, that's, that's how I know those people. And, but I was in class.
And, you know, I showed up to class one day, and we had a guest speaker, and his name was Dan, or his name was Dan Bricklin.
And Dan Bricklin invented VisiCalc.
You may or may not remember, but Sure, I've heard of VisiCalc.
Oh, yeah. So it was the first spreadsheet. It's one of the That's right, pre-Excel.
Yeah. Yeah, well, pre-Lotus. That's true. Yeah, that's right. So this is 1980, 1979.
And he talked about how he eventually lost the company. But he said, you know, when I look back at my life, I feel like I created something.
And it was in that moment in that class when I realized that entrepreneurship was for me.
And I had an epiphany moment that building stuff is cool.
You know, and creating stuff is cool.
And so that's what led to, to military and, And how did you seize on it?
Did you, did you then, like, explore a passion? Because it goes from military service to military.com feels linearly logical to me.
But was it was it that logical to you?
It really wasn't, you know, it's, that's a very interesting observation.
The truth was, and I, as as you mentioned, in my bio, I worked at Harvard Business School for a while, as an entrepreneur residence.
And over the number of decades, I've met with lots of entrepreneurs.
And you know, there are some people who have an idea, like Matthew has this idea that we're going to do Cloudflare or whatever he calls it at the time.
But there's a lot of people who like the idea of being an entrepreneur, but they don't have the idea.
So I was kind of in that category.
And I needed, I owed all this money to Harvard. And I worked in consulting, and I was really unhappy in 1998, thinking I need to start a company.
And so I was thinking about ideas.
And then I was at a reserve drill weekend. And people were complaining about getting access to their benefits.
And they were also doing what a lot of military people do.
And that's like, Oh, did you know this person in the squadron, you must have that, like people that worked at Monster or whatever.
Oh, did you know, you know, or whatever. And I was thinking, okay, holy cow, the Internet is a great way to connect enable and empower this community.
And, you know, I don't want to give myself too much credit, because there were other things a little bit before me.
But this basically was Facebook for the military. So my big mistake was focusing just on the military, or else I'd be huge.
You got you got to start with a small community and then make it work.
Well, it wasn't that small.
It's 25 million people. And but if you count family members, we're talking a lot of people and there's high affinity.
And so I went and pitched this idea with just a PowerPoint and Silicon Valley was not excited.
And but eventually we're able to Why?
What was the missing link in the beginning? Well, first of all, you know, consumer Internet, I guess there was some consumer Internet, it was it was kind of bubbly at the time.
But like, social networks weren't that popular. And I think people were not say negative about the military, but a lot of VCs.
And you know, remember, that world of VCs was the super elite number of VCs.
It was a smaller. Yeah.
Yeah. And they control, they controlled everything that all the power. And I think that they just weren't compelled.
And I remember my first meeting at Sigma Partners.
And I was there with Ann and person I worked with Brad Clark, one of my co founders, and they hadn't left their job.
So they were like, kind of fake employees, you know, like business cards, but we didn't have any money.
And I remember pitching is my first pitch meeting.
And I remember pitching, no questions.
And those you know, seven older white guys, and they might still all be sitting in the room right now in those same seats 20 years later.
But we raised some money.
And then in March of 2000, we launched the website big story. And unfortunately, Ross Perot also launched one at the same time and a bunch of other people.
And then the bubble blew up. And then we ran out of money. And then I got fired.
And then I came back and we turned the company around and figured it out. And then then we sold to Andy McKelvey.
Sorry, it's a lit. Okay, so let's let's I'm going to slow down and like replay that table.
Like, so you build this, this brand military calm.
Yep. By the URL, you have a very large audience, as you described, build the business potential audience at the time, right?
No fast forward tape a little bit, you build, you build the brand, you build website, you have a community, you sell it.
What was the premise? I mean, most of the time when I'm asked to talk, it's to talk about the three years where it was just absolute hell.
All right, so let's talk about that. Okay, well, we can but it was it was the most difficult experience of my life and also the most rewarding.
So the ironic part about this whole thing, including being fired, that the critical path to be I mean, I think I'm a pretty good leader today.
And I think I'm a pretty good leader because the critical path to getting here was being a bad leader, having bad things happen to me, and having the chance to reflect and learn from that experience.
And then try again at military and then try again at affinity. And that's, you know, that's my system.
You know, that's what if you were to like tap yourself on the shoulder, you could like go back and be a little bit of a ghost and tap yourself on the shoulder as you were doing things.
You're like, I wouldn't do it that way before you, you know, you got fired in your own language.
What would that be?
What were those things that are clearly in mind? Because I've given like 5000 talks on this list.
But you know, there's, it's broken out into a variety of parts.
So one part relates to leadership. And the other part relates to probably good decision making or good decisions for a company.
So remember, the broader context in those days is and again, I don't know what it's like at your company.
But early on, when you raise a lot of venture capital, there was a lot of interest to spend a lot.
So our burn rate was incredible. It's like millions of dollars a month.
Because the hope was you could build this giant audience and you could go public even on a big audience and you can monetize later.
And you know, we think that that's a crazy idea.
But companies still do this, right? Look at Uber's losses.
People are doing that kind of business. Amazon lost money for a long time.
Well, that that model can work. But if anything changes in the world, and venture capital dries up, and you know, it hasn't now, it's high risk.
Yeah, it's a high risk way to run.
Yeah, it's a high risk way to run. So all of a sudden, you're dependent on a lifeline adventure.
And if you don't get the venture, then you're in trouble.
And that's exactly what happened. And what happens then is it reveals all of the problems in a kind of more pronounced way in the company.
So a lot of money can hide a lot of problems, you know, you don't have to make difficult decisions about people.
So that's the broader meta context. The specifics were, you know, and what I spend a lot of my time on today, when I work with entrepreneurs, is to build a culture of trust and excellence.
So that's, I mean, that sounds obvious, like, of course, you want to build a culture of trust and excellence.
But there are some real ways to do that. And some real ways not to do that.
And, you know, very personally, I think I've always been a nice enough person, but I was very insecure as a CEO.
And insecurity manifested itself in lots of ways, like, it was all about me, I had to be right.
You know, a bunch of those kinds of things.
And we see people to this day that are like that, right, that have this thing.
But, you know, after I got axed, and came back, I started to realize that it was really about other people.
And so, you know, it's so straightforward, actually, if you lead with a view that your objective is to build an incredible experience for your team, and to build lifelong relationships with your team, you have that as your objective.
By the way, that's my objective, even beyond business success.
Lots of good things happen. Because let's say, you know, you and I have never, like, we sort of work together, but you've never worked on my team, or I've never worked for you.
But if you work for me, and you felt, and I think you might feel this way, you felt that I was in your corner, and I gave you some tough feedback, you probably would take it positively, because you'd say, Chris is trying to help me out, right?
Coming from the right place. Yeah, yeah. If you didn't trust me, it might, you might not see it that way.
Right. So in a world of high trust, and this isn't just applicable in business, everything's possible.
We can all get better.
We all know that we all have each other's back. And you know, that requires some things like you have to be competent in your job.
And so we were able to do that in the second half of military, but really do that at Affinity, which is build a culture where it isn't about your title, it's just about, you know, your contribution and your passion.
And that was one of the best experiences of my life.
And once you start tasting that you, you don't want to be part of anything else.
You know, I would never go, I would never join a company that was like, about money alone, you know, even if it was like a sure thing, it's not for me.
Sure. Because in the final analysis, what matters is my relationship with you, my relationship with Ann, my relationship with Stan Janowski, James Currier, all of these lifelong people, right?
That's right. All the people you work with. So that that would have been the advice I would give myself.
There's some other specifics, we probably don't have time to get into them.
Like, we wasted a lot of money on a lot of things that didn't matter.
Outcomes versus activities, you know, there's a lot of people like PR firms, and all those things that people do, like, did they really make a difference?
Maybe not, you know, branding, we had a branding firm, does that make a difference?
Probably not. So for the for the folks that are listening now, and a number of the people that you just described are people that were involved with military.com, and then subsequently in other ventures, or in the in the ecosystem that have all gone on to do really interesting things.
I want to, I want to slow the tape down, because this there is a subtlety here that I find.
And I referenced it in the lead in, right. So military is a pain, I would, maybe I would summarize it as like a painful success, where we was a long birth.
Okay. So you, you go through this process. Ultimately, where we get to know each other is the company I was with the time monster buys military.
Yeah. And there's an integration, there's a there's a period of time where you're integrated, and then you go off and do something else.
And this is where I, I have, like, can you tell the story of what military was sort of at an atomic level?
And what you did with affinity and how those things are related? Because, yeah, well, the thing I, you know, I'm really proud of is military still exists today.
So if we look at web 1 .0 companies, there aren't so many of them that continue to thrive.
And even inside a tricky corporate parent like monster, which has had its own set of problems.
And I would argue it's because the idea behind military was such a fundamentally good idea, and it needed to happen needed to exist.
So the advantage of those kinds of businesses is they're kind of like airplanes that can fly in bad weather and good weather.
Some things like our friend James Currier, who sold Ooga labs to monster, he built a high performance aircraft that could only be flown by him.
I mean, it went way faster than military, right?
He did all sorts of cool stuff, but it was like a stealth fighter, you know, only he could fly.
So as soon as he left, the thing like fell apart, right? So my second company affinity had a little bit more of that too.
And it's not around. So I sold the company to Andy McKelvey, a great entrepreneur who is the CEO of monster.
And it's we finally figure out how to make military work. And so what it is, is it's like Facebook for the military.
But it's a big idea for monster because what monster monster was about jobs, I guess it's still about.
But you use monster like you use the dating site, you basically, when you needed a job, you went to monster, when you need a date, you go to Tinder, you go to match or whatever.
LinkedIn, who was started by a friend of mine, Reid Hoffman, was running a really tiny little company that we almost bought like five times.
And he did something different.
He said, Okay, well, we'll be your public bio on the web, sort of. And the advantage of that was you you're engaging with LinkedIn, even when you weren't looking for a job.
And the best candidates are many of the good candidates are passive job seekers.
Well, this is the advantage of military, we were engaging with people throughout their lives.
And there's lots of big transitions, buy a house, join the military, separate, but there's also job transitions.
So not only can we help you transition and get a job out of the military and military monster became the largest job transition site in the world.
But we also could keep you for life.
And I think monster tried over some period of time to be more than just a place you went when you were looking for a job.
And ongoing engagement, right? How do you how do you keep that engagement?
Every retention? I don't think they ever did that.
But they military was that effort. And then Andy, so Andy was someone I really admire a lot.
He said, I said, Andy, we should do this for nurses and teachers and police officers and government workers.
And he said, it's a great idea.
And I he said, You should do it, whatever you need. You know, he really loved entrepreneurs.
So he said, whatever you need. And I said, Okay, he said, we'll just support you.
And he goes, How about this, I'll give you all the resources, all the data, and we'll buy it back from you after you make it successful.
And like meaning like he had some deal he worked out with me.
And I said, Sure. And so I went on is, I've never I haven't flown too much private, but he had a g five or something.
And he went his g five out to his mega yacht. And we're on the mega yacht.
And by the way, most row, I think, wasn't it most row? Was that the name of it?
I think this one was the Aurora his second. Oh, okay. And we're there on this boat.
And by the way, I remember arriving at night and like, there's a pier, there's like people on the pier looking at this boat because there's a helicopter on the back.
And he has For context, people that Andy McKelvey is 72 at the time. Yeah, he's in his 70s.
Yeah. Yeah. And it's like, it's like two in the morning, we arrive, and there's like sliding glass doors, like automated.
He's there with champagne.
And like, you know, it's like, he's my boss. This was like super cool. And I get on the boat, and we're cruising around.
And he says, Oh, I need to talk to you.
And I said, Oh, okay. So by the way, you should know, I now have an office, I've hired a team.
So we're part of Monster, but not really. And he says, I'm having to leave the company because of the stock option backdating problem.
And the new CEO is not going to agree to this.
So you're on your own. And I was like, Oh, shit.
I mean, I have no money. I have no data. I have a team, I have expenses. And I almost shut it down.
I mean, it was basically like the rug got pulled out from under me.
And not because he wanted that. He just, it's just the reality. And we were able to get venture capital pretty quickly.
And we did it. I mean, we basically figured out how to create 100 military comms very quickly.
And that by the way, nurses, police, like firefighters.
Yeah. And by the way, that idea is not been executed.
And it's still a very, very good idea. I still think everybody listening.
Yeah. Yeah, honestly. Yeah. So, you know, imagine thousands of vertical communities, and we knew the secret sauce and how to do that.
And we sold it to Monster and the SkySally Newsy.
You sold it back. Like this. So this is the thing.
Okay. Monster buys your first company. Yeah. You go to create a company that basically spins up a bunch of communities and monetizes them.
You get sort of, there's a changing inside the company, you're on the outside, and then the same company that sort of spun you out buys you back.
And you're selling in effect, a version of the first thing, but we'll do it, you know, multiplies.
Yeah, but at this stage, we've already done a lot.
So it was like a year later, but we'd already built a bunch of communities and we had a lot of traction.
And I think people thought military was pretty successful.
So they thought, well, this could be even more successful.
And we had a term sheet for a Series B. So basically they bought it at like a premium to the Series B price.
And which was still, I mean, at the time, it was a good outcome.
But today, I think people would think of it as a pittance, you know, but it was good enough for me to become a photographer.
So, and then I sold the company and I didn't have as good a time there the second time because the leadership wasn't as good.
And so I left the company after two years and I had a strong non-compete and I thought, I thought, well, what is it I really want to do?
And what most people in my position do is they either start another company or become a VC.
And I sort of did the VC thing, but I said, what I really want to do is make photographs and tell stories.
And so that was 2008.
So I guess that was 12 years ago.
And in the last 12 years, I mean, I did some venture stuff, which I do very little of now, but I'm trying to make it as a photographer and that's the hardest job I've ever had, but it's really fun.
So say more about the transition.
Because I imagine what people are going to watch and they're going to listen to the painful reality of being a builder of a company.
And like, it's obvious that's real for you.
And you're very transparent and vulnerable when you describe that.
I mean, I've known you for a long time and you always have this sort of positive can do, but you're always really below that.
You let the vulnerability come through, which is really powerful.
Now you're in this transition where you're moving into like phase next.
What's the existential reality of that?
And we're going to run out of time in like four minutes. What's interesting about phase next is phase next applies to everyone.
It applies to every single human on the planet.
At some point, you're going to do something different. The final transition is death, right?
But there are other transitions. And I know lots of people, lots of successful people, in fact, that have like military people or entrepreneurs.
And at some point, they're not going to do that job anymore. So at some point, you're going to not do your job.
And when people no longer have a regular job title, which will happen at some point, this is a challenge for a lot of people.
So you have to have the confidence. So for many years, I was a CEO.
I mean, you know, whatever that meant, I got the benefits or the whatever. All the things that go with that.
All the things, right. And particularly when I grew up as an outsider.
So this was my protective cocoon in my own identity. So when you have to create a new identity, or maybe the better idea is you have to let go.
And I started practicing Buddhism and I photographed the Dalai Lama for a while. And I believe in this kind of opportunity to grow as a human.
If we're still needing titles and we're still needing external validation, we're not in the right place.
If we're looking at things and money and status as something that's really important, that's a pretty good indicator.
It's a flag that there might be a problem. And this could be another call at some point.
So I have those feelings. We all do.
It's almost part of humanity. It's almost part of a living creature. But I work actively to not let it get in the way of what really matters.
And so that really has been, beyond even being a photographer, that has been the main purpose of this journey, which is to let go.
There's a great quote. I wish I had the courage to be an absolute nobody.
And that's not easy to do. But if you can't do that, you've got issues.
So I'm working on making sure I don't have those. But I think the quote's from J.D.
Salinger. Chris, I learn something whenever I get a chance to hang out with you.
And the phases that you've gone through, I look back and study them as, well, how did you go from here to there?
And we can look back at our life in phases.
And I think that, as you described, some of it is happenstance that you described in your career.
But the most recent, this transitioning into something where you're becoming whatever your next self is before the end of the end, as you described earlier, before we die.
I really appreciate you sharing that with us today.
That's a part of everybody's journey, no matter what.
Well, I have a wish for all of you, and that is consider art in your lives.
Pick up a camera. You know, that really helps a lot of people make sense of the world around them and feel important and feel like they're contributing.
So. Well, with that, that's a great place to end it.
So pick up a camera. Yeah. Pick up a camera.
Chris, it was great spending time together. Thank you for doing this. I appreciate you being here today, and I look forward to seeing you again soon.