Christopher Michel manages Nautilus Ventures, an early-stage venture capital firm he founded in 2008. Nautilus has made over 40 investments including Palantir, Doctor on Demand, Sparks, Goodreads, Castlight Health, 3D Robotics, RelateIQ, Blue Bottle, Ruby Ribbon, etc.

Chris is also an active board member and serves as a Director of Dale Carnegie, Kixeye, Tugboat Yards, and 3D Robotics. Previously he was a Director of Castlight Health (NYSE: CSLT), IDG, the USO, Alliance Health, etc.

In 1999, he founded Military.com, an online portal for servicemembers, veterans and their families. Military.com was one of the first online social networks to reach scale in the United States. In 2006, Chris founded Affinity Labs, which runs a portfolio of online professional communities. Both companies were purchased by Monster Worldwide.

Chris serves on the oversight committee for the Division on Earth and Life Studies, one of six study divisions of the National Academies. He is also on the President's Circle of the National Academies. In addition, he's an advisor to the Center for Investigative Reporting (CIR).

He was also an Entrepreneur-in-Residence at Harvard Business School during the 2010-2011 school year. Prior to his business career, Chris served as a Naval Flight Officer in the United States Navy. While on active duty, he flew as a Navigator, Tactical Coordinator and Mission Commander aboard the P-3C Orion aircraft. Following his operational tour, he worked in the Pentagon as Aide to the Chief of the Naval Reserve.

Chris earned his commission from the NROTC program at the University of Illinois, where he graduated Phi Beta Kappa and was selected as the distinguished naval graduate. He also holds an MBA from the Harvard Business School and an honorary Doctorate from Tiffin University. Michel was named a Henry Crown Fellow of the Aspen Institute and serves as a life member of the Council on Foreign Relations.

Startups, Travel, and Photography with Christopher Michel

Michael:         

(00:02) Hello, welcome to episode number 98 of CXOTalk. I’m Michael Krigsman and the guy laughing in the background is my co-host Vala Afshar. Vala, how are you today?

Vala:   

(00:18) Michael I’m doing great and anticipating another foot of snow in another day or so. So this has been a pretty white environment around Boston area.

Michael:         

(00:32) Yeah, I know it’s like you know, can I curse on the show out loud? Do we allow that or no?

Vala:   

(00:40) It’s beneath you so no.

Michael:         

(00:45) Okay, so on Facebook I put,’$*%$ the snow!’ because it was snowing and all these people like started commenting and now were getting – we’ve had feet of snow, like inundated with snow.

Vala:   

(01:00) We are but the best part of this is we get to end the week talking to an extraordinary entrepreneur and technologist and photographer. So please Michael with the introductions.

Michael:         

(01:12) So on episode number 98, we have as our guest today Chris Michael, who is a serial entrepreneur and he’s also invested in a bunch of companies and is really one of the great photographers. Chris, without a doubt you are the photographer, without a doubt in Silicon Valley and among technology people in this country and we’re thrilled that you’re here with us. 

Chris:  

(01:45)Thank you. Well I disappointed I’m not episode 100 and I appreciate the incredibly qualified view of my superlative; you’re the top photographer in the south of the market area in technology. And I claim that and own that space as my very own.

Vala:   

(02:06)….San Francisco.

Michael:         

(02:09) I think this has been a great show and…

Chris:  

(02:13) Vala you’re right, it’s been difficult. This is going to be a tough hour.

Michael:         

(02:18) Okay, so let’s start over. Chris Michel is – I love Chris Michel photography and we’re going to do a unique thing today, which is before the show is over we’re actually going to see a slide show. Chris sent me a bunch of his photos and they’re really great, and he’s going to talk through just the story of some of these. So but first, Chris why don’t we begin and tell us briefly about your professional background and some of the highlights of the many many things that you have done.

Chris:  

(02:50) Well thanks, and it really is an honor to be here. I guess, well I would say I’m 47 now and so it sneaks up on you and as look back I’ve had a pretty unusual life, maybe a life that I didn’t expect to have. I had three really distinct careers.

(03:09) So I flew airplanes for the navy as a navigator, so after Top Gun I was very interested in joining the navy and thinking I maybe want to go into politics, and I flew on P3 Orion’s. I’m trained to hunt Soviet submarines. I spent a lot of time doing drug trafficking and after that I went to work in the Pentagon.

(03:29)During that time I was at the University of Illinoi and was in the navy and as I said I was in the Pentagon. My level of interest in business was zero. So I had never taken a business class. I probably didn’t know the word entrepreneurship, I was not compelled and the navy was going to send me to the Kennedy School Harvard, which was kind of a big deal, because I had gone to State college as Illinoi.

(03:50) and basically through a serendipitous set of events, I ended up going to business school and was inspired in business school in business school and entrepreneurship and technology.

(04:00) Came out and started my first internet company in 1999, call military.com, which was sort of like Facebook social network for the military and it’s still around. The in some trials and tribulations in 1996, I stated Affinity Labs. I sold both of them to Monster in 2006. Started Affinity Labs in 2008 and sold it. then decided what I really want to do was travel and tell stories and be a photographer and that’s what I’ve been doing since.

(04:35) I run a little investment firm called Nautilus Ventures but I am by no means a great venture capitalist. I am really an entrepreneur that’s made a lot of mistakes that tries to help people where I can and try to tell their stories because I find them very interesting. So three careers, or moderate success or passible success in all three and we’ll see what’s next.

Vala:   

(04:57) What was the compelling event, how does an Navy officer end up as an entrepreneur, was it the courses and the classes? Was it an individual that influenced you along the way, or an exciting technologist or business opportunity?

Chris:  

(05:14) Yeah, well that’s a great question and you know when I get the chance to talk on entrepreneurship, I am compelled to share with people is kind of maybe the opportunity for inspiration to change our lives, and sometimes that inspiration happens in very kind of unpredictable ways.

(05:35) And you know, maybe somebody is listening and maybe they can hear something that will make a difference, and this is what’s so exciting about teaching, is that teachers have this opportunity.

(05:43)So the serendipitous of that was basically, I was going to go to the Kennedy school to get a Master’s in public administration, and I had ran into an Navy guy who had gone to Harvard business school and he said, really, you should go to the business school because you know you can do whatever you want. And I’m thinking, well, I don’t know if I can get in, but if this Navy guy could get in then maybe I could get in, and I was lucky enough to be part of those adversity admit programs.

(06:10)And showed up at school not knowing about business and I really got schooled. You know I had done pretty well in the navy and I remember sitting there in the classroom on the first day, and I saw all of these Golden Zac’s people, and McKinsey people and you know, never having had a business school class in my life. And it was a scary moment, maybe as scary as you know being at the end of the Gulf War.

(06:30) And I tool a class on entrepreneurship, and one day they brought this entrepreneur in named Dan Brooklyn. Do you know Dan and do you remember what Dan is known for?

Michael:         

(06:49) This is age.

Chris:  

(06:57)So imagine you’re a student in Harvard business school in 1997 and I should say I was the tech nerd and into computers since 1979 and loved technology, but didn’t think of myself as a business person. So you know, the world has changed a little bit, everyone’s an entrepreneur and you know you automatically think, well, I can create a company.

(07:18)In 1996, this is not the way, and it’s not as persuasive and this guy, Dan Bricklin, who doesn’t look like other people who visit the Harvard Business School. He has a beard, and a flannel shirt and maybe it looks like entrepreneurs in San Francisco today, but he was quite different.

(07:33)And he talked about creating this company and I created it when he was at the business school because he didn’t like the way they were doing accounting. And he talked about starting the company and how important it was, and you start to realize…

Michel:           

(07:47) Software Arts.

Chris:  

(07:57) I thought it was VisiCalc, but you may now better. But when you bought a computer in 1980, the three killer apps on the PC were you know VisiCalc, WordStar and the adventure (game?) So he had built a piece of software that would be an excuse for people to buy a computer. And he talked about his trials and tribulations, and as we know Lotus 123 and (? 08:23) put him out of business, and you know, if you ask young people today they’ll say it’s Microsoft and Excel, and it wasn’t a great outcome for him.

(08:34) He talked about how important it was in his life and as he reflected on his life, having built something that mattered was the most important thing. And to be respected and to feel he did something was the most important thing and boy, really it resonated with me and I knew right then that what I really really wanted to do was start a company.

(08:53) But that’s good news and bad news because once you decide that’s what you want, well then what do you do. Well, I want to be an entrepreneur, but where do you get the idea. And that’s where I was in the state of high anxiety at the Harvard Business School in 1997, trying to figure out what it is that I was going to go and do.

Michael:         

(09:09) And so how did you come up with the idea of Military.com?

Chris:  

(09:12) Well, I helped set up a (? 09:14) company when I was at Business school at the tech transfer office and it failed. And I only had one job offer with Mercer Management Consultancy in San Francisco. So I came out to San Francisco and worked in strategy consulting. I learned a lot and can commend it to people but I was really unhappy. There was a lot going on. I mean, in a way 1998 was  a little like today in terms of buzz, excitement and venture capital and I wanted to start a company and I didn’t know what to do, and I didn’t’ know where the idea would come from.

(09:44)I was also in the Reserves. I was drilling in one week on a month, two weeks a year, although during the war more than that in my squadron. And I remember vividly in the summer of 1999 and going to a boardroom meeting, and all the officers are sitting there and sailors will do what sailors do. They are bitching about not getting access to the benefits and they were also asking me if I know a lot of people from other squadrons. So sort of like two people that went to the same college who would say, did you know Val or did you know Michael or did you know Bob.

(10:17)They were doing this around the Navy you know the Navy’s small enough so you might actually know people. So two things, one was they were trying to connect with each other on an offline way. And there was a lack of transparency around government benefits, and there is 24 million people in the military community.

Chris:  

(10:32)So, literally you hear this and it’s really true. It was you know, it hit me like a ton of bricks and that the Internet was the perfect vehicle to connect enable and empower the military, and so I left that meeting knowing that I was going to start this company, and basically quit my consultancy job you know a few weeks later still owing you know $100,000 to Harvard and I started on my entrepreneurial journey.

Vala:   

(11:01) That’s amazing. Has there been a common thread in terms of the companies that you’ve founded in terms of connecting people, has it always been something that has inspired you to jump from one project to another.

Chris:  

(11:16)That’s an interesting question. Well, we can talk a lot more about you know what I learned at military.com, but as I said I love technology and I was using proto-social networks in 1996/7. I was really fascinated and it was interesting stuff. And you know in building military.com, it was a really difficult experience. I got fired, I learned a lot and it was a transformational experience. But I figured out some things through some difficulties, and then than we sold the company to Monster it was doing well.

(11:49)So basically we had this community where we could bring people together and you know this was pre-social network, this is pre-Facebook and it worked. And I thought and thinking, well it works for the military and I remember Monster at the time was quite a big company and being a jobs company.

(12:11) And you know, part of what we did was help people transition out of the military and get jobs. That wasn’t the only thing that we did, we helped them join the military, relocate, user educational benefits, find each other, read news – it was like a kind of like Yahoo meets Facebook for the military, and it worked. I thought well, we should do this for nurses and teachers and police officers and government workers, and skiers – and I thought well, think about the Monster database with everyone’s resume.

(12:37)There is all these like de facto professional networks that are in the data, and you know what I’m saying, like if you are a CMO, that’s a community of people. You know, CXO is a community of people. And I thought what we could do is build a platform to go and do that for all of these different communities, right, 1000 Facebook’s.

(12:55) So I talked to Monster about it and I said well we should do this and they didn’t want to do it. So it was a little bit more complicated story, so I left and did it on my own, basically using the lessons from military.com. So in a way you could say Affinity Labs, my second start-up – well we actually built like six professional communities, each with their own URL and each like military.com and we sold the company after we did that. But the idea that we would do hundreds of them. So I guess there was a common thread and some of that common thread was passion, but some of that common thread was that we figured out a model that worked and I felt that the model could be replicated.

Michael:         

(13:34) So you started a couple of companies and sold them, and you’ve invested in a lot of companies. What are some of the primary success characteristics or the obstacles, because it is really two sides of the same coin for start-ups and entrepreneurs that you’ve observed in your experience?

Chris:  

(13:55)That’s an interesting question. Well, you know I would say that all of my entire view of this was informed by a very personal and difficult set of experiences in the sea of military.com.

(14:12) So, I can tell you about those, because I think it does inform the lens in which I see companies. You know, but there is a difference between a successful investment outcome and a successful company. A successful investment outcome is you know, I put money into a company and the company somehow has an exit and returns more capital that I invested.

(14:40) And a lot of companies today sell early and sell before they had to build an entire infrastructure around sales and so they have sold on promise. So you know, I don’t know if I have a view on that or other than it’s difficult to say, well with a lot of these companies there is a lot of happenstance, and a lot of these products going into businesses are really little products. They are little product teams and little companies – sort of and sort of not.

(15:05)Eventually you know if Instagram had stayed private, they would have to figure out their business. They would have had to have delivered a real revenue model – I mean I think they could have done it, but the challenges they would face would have been very different from the challenges that they faced in creating an incredibly compelling product that was used by a lot of people that you know that Facebook eventually wanted to buy.

(15:25) So I would say I would differentiate smaller companies that are really operating on promise and aren’t revenue, and aren’t folks in revenue, and then companies that are really having to do the heavy lifting every day, deliver the quarterly revenue, deal with large people on the team. You know, so two different sets of kind of observations, and two different sets of different outcomes. So I could talk about those or I could share with you the military.com sob story, redemption story.

Vala:   

(15:55) So if I’m looking to start a company, can you give me some advice. I mean what are some of the things that I should avoid and how do you build a strong team. You said some of these companies have little products and they are not quite companies, but they are building around a potential. Any life lessons that you can throw down and something that I can tweet as well – now I’m kidding! You know, the big question narrowing it down to something like a precise lifelesson.

Chris:  

(16:24) You know it’s funny because just before we came on air we were talking about as we have gained more knowledge, inexperience, and life well at least I’m believing I know less and less. You know, and this is quite a disturbing trend.

(16:45) I feel like the c is hemical of my knowledge and competence in my knowledge was the day I graduated from Harvard business School, where I felt that I knew everything. And it’s just been really going downhill from there, and I don’t know where this ends but it’s not probably good.

(16:58) So, I think I won’t be able to give anyone advice soon, because I feel like there are a lot of nuances. But I think that there are some synthesized truths. So I have one piece of advice and it’s going to sound very very obvious to you, but it is the single most important – well I’m going to even caught it for you and it is the most important quote I have heard in my entire life. I think if someone does this as an entrepreneur or potential entrepreneur, they have completely changed the odds in their favor. Are you ready? You know I’m not going to tell you!

Vala:   

(17:35) The suspense is killing me!

Chris:  

(17:40)You know why, because if I keep it to myself then I could be the guy. I’m only going to share with companies that will let me invest in their company, but it’s incredible! I’m obviously just kidding; I’ve built it up too much.

(18:01) It’s a quote by John Boroughs, and he says, ‘leap and the net will appear.’ And this is everything to me. The difference between you know everyone in the world and a lot of these well-known entrepreneurs is they just took some risk. People that are really smart, really thoughtful, and understand the deep complexity of companies often at times are paralyzed with analysis.

(18:34)You know, this is the stay hungry and stay foolish misattribution to save jobs. Wasn’t it (stored brands, Whole Earth catalogue? 18:40) stay hungry and foolish, very difficult to do. But, I almost don’t care and when I meet a great entrepreneur I almost don’t care what the idea is exactly. I mean yes, if they are going to do something that is super difficult and they don’t have a lot of capital, and it would be easy to raise capital. Well that might give us a little bit of surprise. But if they are working on a pretty good idea, just go do it. Just go and say, I’m going to go do this company.

(19:07)You have to believe me, I think in authentic leaping isn’t so good, why you say I want to be an entrepreneur and you know, I’m just going to be an entrepreneur. It’s okay and it could work. But we would rather have one that is passionate around some idea or around something that you think that needs to be fixed, you’re authentic about it and then just go do it. And you know, it will work itself out.

Michael:         

(19:29) Can you elaborate on what do you mean by ‘authentic.’ It’s a really interesting question, because the point of view of the person who wants to do this it’s genuine interest in every case. But when you said authentic, there’re other characteristics; like that they understand the market, that they have some capabilities. Can you elaborate on that?

Chris:  

(19:58) Maybe I was giving that a very specific point. When I meet a lot of entrepreneurs they really believe in their idea, right. What do they say, there’s that great quote, ‘something’s need to be believed to be seen.’Right, and when I meet an entrepreneur that really believes something right, that’s what I mean by authenticity.

(20:24) Sometimes I meet people that are raising money and you know and we have a cult of entrepreneurship now, which I think is mostly good, but we have a lot of people in the field now and so many people want to be entrepreneurs and I don’t know if they you know as if many of them believe in their idea as maybe they did five years ago or six years ago.

(20:46) Right, they really believe in that idea of being an entrepreneur and they know they need to pretend to believe in their idea. But do they truly believe in it, because this is a very important characteristic. It’s not required, but it’s very important because if things get difficult and they get challenged in a really fundamental way, do they have the hutzpah to believe the passion to take it all the way to give it everything, you know.

(21:13)So I don’t know if they see that distinction. Some people seem to like their idea, but you’re not sure in whether they fully believe it, and some people you know, believe it more than anything else. And the latter of the most authentic and the one I like the most, it’s a characteristic of an entrepreneur that I just adore.

Vala:   

(21:30) Do you have to see and feel the focus and sense of urgency in order to call it authentic. Can you be authentic if you lack focus and urgency when you’re trying to start a company as an example?

Chris:  

(21:49)All of these are generalizations, yeah, I mean there’s lots of people who have lots of different characteristics. So I think you can be authentic and not work hard. You know I think it’s possible.

(22:05)There’s a portfolio of characteristics that seem to work really well. you know, it’s integrity, it’s caring for people, it’s passion, it’s some smart. And you know, the other one that’s really important is tenacity, right. You know if we had a half an hour I could tell you over and over and over again I was faced with challenges with very smart people including board members who told me to stop working in the company.

(22:37)One of them is a gentleman called Mundy, who was coming out of the Marine Corp and adviser to my company, so (coming out of the Marine Corp? 22:43) is the CEO of the Marine Corp. So this guy is an important four star general and he said to me during the later of military.com, he said, sometimes you need to know when to give up on the battlefield.

Vala:   

(22:56) Did you ignore his advice?

Chris:  

(22:56) I almost didn’t. you know the board told me this would take a non-profit. You know I got fired. I came back when the company had like six people in it and we were basically talking to bankruptcy lawyers. I didn’t give up, and this exact thing didn’t happen like this, but we had a number of cases in other companies and things got difficult. And now, I see the power of that moment.

(23:25) I see the power of what happens during that diamond creation process was incredible pressure. And you know we were talking earlier about real innovation. A lot of real innovation happens through these difficult processes. And this is why a lot of big companies can’t really do the most difficult kinds of innovation, because it requires a kind of super human effort and a kind of personal sacrifice that only happens when entrepreneurs feels that this is almost the most important thing to them.

(24:00)You know, at military.com I didn’t have an alternative. If I didn’t make the company work, I wasn’t hirable. I owed a lot of people a lot of money. I remember asking my co-founder if I can sleep on her couch because I worried that I didn’t have enough money to survive. So the alternative to me to making the company work was a kind of death, and that’s a powerful forcing function.

(24:26) I’m not saying it’s easy today. I’m not saying you need that. but if you don’t have a lot of tenacity you will not go that far and you will potentially miss the opportunities to do some really great things.

Michael:         

(24:36) Well there has to be something that’s motivating you to do that, either intense personal drive or not want to have to sleep forever on your co-founders couch or whatever it might be. It has to be something.

Chris:  

(24:53)Well you know, we all suffer from ego challenges and insecurity. You know I find insecurity an incredible fascinating thing, and even as we all know that with the most accomplished people are incredibly insecure and it’s a kind of driver for them and it’s a powerful driver. And we don’t like that characteristic, but again it’s a powerful driver.

(25:18)And my insecurity was that I was a Navy guy, never had a business class and was always the outsider and I moved date times as a kid. I felt like I was an admission mistake at Harvard. When I was doing my first startup I was an outsider, a military guy – I had something to prove in a big way, and you know that helped me. I hurt and you pay for it but it helped me.

(25:42) So what are people drivers, well you know there’s another driver. One advantage to raising capital from people is you make a commitment to the others, you’re going to deliver for them. You hire a team you have a commitment to the team. So there are things that can force us to leap. I always tell my friends who are successful, well if you really want to make it happen, just go and raise $6 million in your Arab. Right, then all of a sudden you have a board of directors is like your coach who is waiting for you to deliver. And the next thing you know, you’re treading water and you’ve got to swim. You’ve got to make it to shore.

Michael:         

(26:15) So you you’ve written a lot about and spoken about activities versus outcomes. And so maybe link that in and I’m just looking at the time and maybe for a few minutes because as people watching probable know you’re this great photographer and we have a slide show set up, where you’re going to talk us through some of your photos. So I want to be sure we have plenty of time for that. so activities versus outcomes.

Chris:  

(26:43) The military.com talk and when I talk about the nature of that experience of having been fired, you know I had about three month of the fired CEO and just to put a fine point on it, when they hired the new CEO, he sat in my office in my chair, as I came in and sat in the guest chair, you my office with all my things. And he said, you know it’s probably best you don’t come by the company anymore.

(27:09)You know, just think about what that might be like and how it was feeling. And so I went swimming. There was a swimming pool at the gym and I swam every day, and I really thought about what the mistakes were in the company, and there was a variety of mistakes.

(27:23) Leadership mistakes around the characteristics of great companies that I didn’t follow. Like is everyone in the company an A-player, were we getting rid of people that weren’t performing that were either nice but not great, or maybe great but not good people that could sit in the company. Because you know that really doesn’t contribute to an incredible corporate culture.

(27:44)And one of the things I really believe in so deeply is how possible it is for CEO’s to build incredible cultures. How there is an approach and you build that kind of culture and I feel we did that in the second half at military.com and at Affinity Labs you can do anything. You’ve built a machine that can do anything. You’ve built the Special Forces team that can solve any problem, break through any walls and I love that, and it’s one of my most favorite things in the world.

(28:10) One of the othermistakes that we made is you know we raised $25 million, and we were doing a lot of things in the company that they looked like good ideas and they were good activities, but they did not lead to outcomes.

(28:24) So what I’m getting at here is there is a whole lot of things that we can do that seem like a good idea that we engage in, but can you tie it to an outcome for the company, can you tie it to revenue, can you tie it to users, can you tie it to business success?

(28:40) And when you raise a lot of capital and there is no forcing function, there is a lot of danger. And you know since I have talked a lot about this, there has been a lot of movements here, lean movement. A lot of companies are doing a lot with the seed so that they don’t have a lot of capital, that’s a good forcing function for people. But I also see a lot of companies raise a lot of money, or big companies or think about the government. Think about how much money we spend on education or defense. You know, the challenges that we have in these areas are not related to the amount of capital we’re spending.

(29:12) We’re just doing a lot of things that may not matter, and having the discipline to see the difference between these activities, and I’ll give you an example. I was spending $20,000 a month with our PR firm. So let me ask you guys, the PR firm comes to us and says, I have got a front-page business week story for you. Is that an activity or an outcome for my company?

Michael:         

(29:39) It’s a tough call, because a front-page story in Business Week is pretty significant from a marketing standpoint.

Chris:  

(29:45)Well okay, I’m going to say it seems like a pretty good thing, right. But it isn’t directly an outcome. Right, lots of press isn’t directly an outcome. That press has to lead to something. That has to lead to sales. It has to lead to revenue; it has to lead to hiring. It has to lead to something.

Michael:         

(30:03) So it’s a process item.

Chris:  

(30:04)Well it’s really – yes it’s a process item, but it’s really that somewhere in the company you’re asking the tough questions around, are these things that we’re doing making a difference. Is bringing in this great web consultant making any difference, is building this piece of condo making a difference. Is this feature making a difference?

(30:20) Look it’s easy to point at the things that don’t seem like the things. It is really hard to triangulate on those few things, those few levers that really make a difference.

(30:31)Like think about your own show. You could have lots of people on the show, you could do lots of tweets, but there might be a few things and you did them right, they really move the needle. So I didn’t do that right, I wasted – we did a lot of advertising and I probably wasted 15 million of the 20 million, and you know, I’m very very focused on helping the companies that I work with to not make those mistakes again.

(30:57)You know I think about it even in my life and what I have observed in the world, and a lot of people struggle with this.

Vala:   

(31:04) But to be fair you didn’t have the technology to measure outcomes or desired results did you, without marketing automation, CRM, influence reporting, predictive analytics – I mean how did you measure out 15 years ago in marketing?

Chris:  

(31:20)Well we were one of the early companies to do online lead generation. So one of the evolutionary with military.com is we got very good at figuring out how to spend marketing dollars that were profitable in the company. So we were able to tie – I mean we have data scientists, and we were tying marketing work with driving registration leads on the website.

(31:43) But I think the danger here is – yes if you have thoughts analytical tools it’s a lot better. But there are still a lot of things that you can be doing that seem like a good idea, but we don’t think we can measure them. And you know, I just think we should be very cautious about those activities in our lives.

(32:04) I mean, when when I was at Monster, they were hiring the biggest ad agencies in the world doing Super Bowl ads. One of those Super Bowl ads helped Monster a lot and the rest of them wasted almost $1 billion.

(32:17)So, and you know the ad agencies are going to tell you a lot of things about how their predictive analytics and their audience measurement are really helpful to you. And now I look at that and I think incredible skepticism. I think frankly, CMO’s and CEOs need to be looking with incredible skepticism in a lot of these things and they don’t move the needle for them.

Michael:         

(32:36) Well there is no doubt that for many start-ups that there is a strong element of ego that’s involved, and I’m sure that many start-ups make the argument, these huge fancy parties and these are important to spread the word. But let’s face it, these huge fancy parties are a lot of fun, and it’s a lot of fun to spend money, especially somebody else’s money.

Chris:  

(32:57)I’m so glad you brought that up because you reminded me, I have a story. When we launched military.com I remember we had a very famous board member when it was my first time as a CEO and do you guys know about the launch party at military.com, have you ever heard about it? it was a famous thing, but maybe famous in the olden days.

(33:14) We rented an aircraft carrier and shipped people by boat out to this aircraft carrier and the guest speaker was one of our advisors, Steven Ambrose, who wrote Undaunted Courage and Citizen Soldier and there was a view that this would be helpful on our brand and be a big splash and there was a US Today story and there was a lot of these things. Gentlemen, this was a waste of money.

(33:36) It was a great memory, but that was an outcome and really something I’ll never forget. But you know, I see this in companies. I go and visit all these start-ups now, they have incredible offices spaces and they you know, provide all these perks to people. And you know, they think it’s making a difference in the company. Is it?

(33:53)You know, I actually think we get confused in Silicon Valley around the things that really matter to employees. Right, we thinks it’s camp or we think it’s equity package or some earn-out or we think it’s what this office space might look like. Those things are important for sure, but they really keep us from the real drivers of human behavior.

(34:14)And I know and the reason I know about this is, I was in the military. And in the military there is no special pay package who are for extra performance, you know you don’t get a bonus. I tell people that we’re very good, work very hard and do their very best, because what they really wanted to do was the right thing. They wanted to be acknowledged for it, they wanted to feel proud of what they were doing.

(34:38)This whole pay compensation schema that we think is driving a lot of behavior is a false area of optimization. The primary driver is really good leadership. It’s really inspiration. It’s really making people feel valued that this is a good use of their time and proud of the work they’re learning. You know, those are the things that we should be working on. Those are I think are the biggest levels. A lot of people will work for almost nothing if they like what they’re doing isn’t important.

Michael:         

(35:08) Chris, we have a question from Twitter from Christopher Kelly is asking what is an A-player to you and I’ll ask you to answer very briefly because we’re just going to run out of time. Very briefly, what is an A-player to you?

Chris:  

(35:34) Well to me you know in my quadrant which is you know fit a high to low and confidence high to low is somebody that is contributing to the culture of the company, that’s somebody that we can work with who we care and we trust. That’s passionate about their job, and they’re good at their job.

(35:52)So to me it’s a, you know you’re in the quadrant of you know very good, very technically competent at your job, and you’re a good fit in the company. And you know, it depends at what level you’re at in the company, but ideally a leader.

Vala:   

(36:08) Competence, confidence, and character.

Chris:  

(36:11)Yet, but really a whole other show can just be on all of the challenges that we have with these people that are incredibly good at their job, but are problems for the company. In many cases there is just a lack of confidence in dealing with them, because we are afraid of losing these people and it’s really hurting execution in a lot of companies.

Michael:         

(36:32) Well when one looks at your photographs, one of the things that really comes through – especially your photographs of people is empathy. And so maybe can you connect this notion of empathy to running a successful company.

Chris:  

(36:53) Well I would say if I was to triangulate on one thing that led to my failure is the CEO in military.com in 2001 when I got fired, is that I didn’t build sufficient trust and connection with my team, and this is a problem. You know, I would say that you could skip your MBA and recommend a book called the Thin Book of Trust, it’s really short and it’s a really incredible book and it will take you about 20 minutes to read it.

(37:24)But if you could build trust in people and connect with them, people will do almost anything for you. You can give them direct feedback, you can push hard and asked a lot of them and if they trust you, you can have a great dialogue, but if they do not trust you, and you have a major problem.

(37:43) And you know, I learned these lessons and I saw what was possible and I mean you know, I would say the source of lack of Trust to some extent was we had a bad business environment. But it was really that I was a first time CEO and sufficiently insecure that I felt like I needed to bully people, or I needed to show them that I was smarter and I was not vulnerable and you know, what a giant mistake. So the overcompensation of my own insecurity led to huge trust issues.

(38:10)And you know where those pressure issues that much greater than other companies. You know, it wasn’t incredibly bad, but what I was really missing was how much better it could have been. So I’ve really over the last 15 years I’ve really just grown to love people and love working with them and appreciating their own lives and what they’re going through. You know, once you build that kind of environment, my relationship with my employees and company is a lifetime relationship.

(38:30)You know, I even tell them, one day you’re going to lose passion about the company and I’m going to help you get another job. But you know, this isn’t a one-off transaction. So, I don’t know I feel that way when I take pictures of photographs when I take pictures of people as well. I feel a real connection to people and it may be an artefact of just getting older and knowing more people. But to me, they seem not unrelated.

Vala:   

(39:02) That’s incredibly inspiring anything less to be fortunate enough to be in leadership roles have to view it as a privilege and constantly work at. I’m thinking about a Simon Sinek tech talk and he says, we all know what we do. Some of us know how we do it, but often we don’t know or don’t communicate why we do what we do. And as leaders it’s to establish those connections and trust and they need to burn some calories explaining why we do what we do and being involved with employees. So your commentary certainly resonates with me and I appreciate that.

Chris:  

(39:44) Well we’ve all had bosses where we just didn’t trust them. Right, we just didn’t know if they cared about us. You know, that’s not a good position to be in and I mean it’s not just related to work. It’s related to everyone in our lives. And you know, it’s sub optimal performance if you don’t trust people and it’s incredible performance if you can build the trust.

(40:07) I think to be honest with you, the first step is to be vulnerable and to talk to people. You know, I remember in my latest company Affinity Labs, you know we’ve built such as cool culture that even junior people felt that they have the right and obligation to give me feedback as the CEO. All of that stuff I wasn’t doing right. It’s kind of cool. Like you know, you can look at it and say, well I don’t like that because it reduces my power in the company. But you always create a kind of invulnerability if you are like okay with it and appreciate it. And you even look at it intellectually and depersonalize it. You know, we are kind of all in it together.

(40:42) Does it work in a company of 5000 people, I don’t really know. I haven’t run a company like that. It certainly works in the company with hundreds of people, and it’s the big opportunity because you can get to really know those people and it can be a really cool experience.

Michael:         

(40:57) Well without a doubt we can continue talking about this, it’s such an important topic and trust is the foundation for anything that involves the successful outcome of people working together. But, do you see my screen with the photograph right now?

Chris:  

(41:20) Yes, my space suit selfie.

Michael:         

(41:23) So let’s take a look at some of your photos. So…

Chris:  

(41:40)What’s going on here, you tell me, what’s going on here?

Michael:         

(41:45) It’s like, okay, it’s a selfie but obviously, you’re not holding the camera and you don’t have a selfie stick.

Chris:  

(41:56) It’s a Go Pro and I just turned on to take the photo, and in fact I didn’t know I was taking a selfie. What I’m doing really is I’m monkeying with the camera that is also taking photos, and it looks like a cool selfie photo.

(42:12)But basically, here is my humble brag, and you know, I was incredibly fortunate to be flying at the edge of space with the United States a force. So in this photo I am the 11th highest person in the world, which is probably the coolest thing that I will ever do in my life. And I’m in the back seat above the pilot of a U-2 spy plane at about 72,000 feet.

Michael:         

(42:38) Vala, what can we say?

Vala:   

(42:41) Nothing that’s quite a humble brag.

Michael:         

(42:45) Yeah that totally works as a humble brag.

Vala:   

(42:48) Yeah, there’s nothing that you and I are planning to do or in the past that I can think of that quite matches that and what must have been incredibly exhilarating, humbling, wow it’s a big world experience.

Chris:  

(43:04) Yeah, I mean I could see the earth curve and well, there is only one downside of having this experience and maybe it is like a date going out with Scarlett Johansson, where you don’t get a second date and that might have been as good as it gets. So they handed me a bottle of champagne and the general saluted and I took my space suit off, and this is the best moment of my life and it’s about to end. At least I can look at the photo and remember.

Michael:         

(43:31) How did you make it happen?

Chris:  

(43:36) I gave a talk to a bunch of generals at Davis–Monthan Air Force Base about leadership and innovation in the military and they’ll knew I took photographs, and this guy comes up to me afterwards, this Col. He said, if you come to my base and give a talk, I will fly you in the U-2 and I’m like, what did you just say. I didn’t even know the U-2 was still flying, which they are. So it was a quid pro quo, so if I did an article for a magazine and I did some photographs and I did the talk, and that was the experience.

Michael:         

(44:11) Well I’m afraid that we appreciate you being on CXOTalk today but that ain’t going to happen here. So tell us, what are we looking at here?

Chris:  

(44:32) I occasionally work for a company called Backroads and if you don’t know them, they are a cool company to know. They do active travel trips and biking, hiking all over the world and the not that expensive and you can go anywhere. I’ve been on some really really amazing trips with them, and I have a nice deal where they let me go on trips for free if I take some pictures for them. And I was out on this mountainside just hiking along in Peru, and there’s this woman – I guess she is a villager.

(45:01)And she is just walking by me, and she is just picking up you know flowers and just having a kind of moment, and I love this photograph. She’s not engaged with me, and she’s just having you know, a moment outside and she seems so happy and so connected with nature and so real. It just makes me smile every time I see this photo.

Michael:          (45:24) It’s a lovely photo.

Chris:   (45:29)So who is this?

Michael:

(45:32) Well this obviously the Dalai Lama

Chris:  

(45:35) Okay, well done. So I’ve had a couple of cool photo assignments, and one of the cool photo assignments was that I knew this monk and he runs the MIT ethic Center at the Dalai Lama center and MIT, and he is friends with the Dalai Lama and the Dalai Lama is coming and he said would you be the Dalai Lama’s photographer. And so for three days I was the photographer and I was a few feet from him. So we travelled around and went around with the security people and you know, I’m kind of a Buddhist.

(46:14) I say kind of because there is lots of things that I’m sure I could be doing but I’m not doing, but when you get to spend some time with the Dalai Lama and somebody who I have always respected, you don’t know what you’re really going to find when you get behind the scenes. Is he really the person we think he is. Is he really kind and compassionate even when the doors are shut, and I can tell you he really is. He is better and more authentic and more loving, and more funny and more scientific than I had even imagine.

(46:44) And I saw – I mean when you are around somebody that many hours a day, all day long and this just gives you a little sense of this kind of, you know his energy. Just smiling, happy, and engaged and it was a really cool experience.

Michael:         

(47:01) Lucky you.

Vala:   

(47:03) I was just thinking about that, and I do know what to say, when you give the world gives back and boy, you have had an extraordinary life and this is pretty amazing stuff.

Chris:  

(47:15) I feel really lucky. Okay, what’s going on here anybody know?

Michael:         

(47:23) I was thinking, burning man, but no because this is either in China, Tibet, it has to be Tibet or Nepal or something like that.

Chris:  

(47:40) Well what’s so funny is that you asked me to send you a collection of photographs, and I just looked quickly and just pulled out a bunch of photos, and it is incredibly ironic that we had a picture of the Dalai Lama and then this photograph, and I didn’t mean it but I now just noticed why it’s really ironic.

(47:58) This is Lhasa, Tibet. This is where the Dalai Lama ruled, this is his palace. And he fled from the Chinese and his palace when he was a boy to Dharamsala, India. He hasn’t returned, and the Chinese won’t allow him and you know there is a huge problem is China. And all of these people are Buddhists and they are all doing morning kora around the temple, right near Potala Palace. This isn’t Potala Palace it is right nearby, and behind us.

(48:31) They were doing morning kora, and they were going around the temple in a clockwise way and this is in sense that’s burning, right. These are all Buddhists, except if you can look into the centre of the screen, you see a man with a military hat. You see that with his arm outstretched? That is a Chinese soldier kind of being aggressive with the people.

(48:50) And really a very interesting juxtaposition of these two photos.

Michael:         

(40:56) I figured it was Tibet because on the left-hand side I saw the Chinese characters and then at the top in the center I could see what looks like a stupa or Tibetan prayer flags, so had to be.

Chris:  

(49:13)You got it. That’s it, so this is sunrise in Chinese occupied Tibet.

(49:22)This photo hangs in the Battery club in San Francisco

(49:32) It’s a train station in rural (? 49:35) There’s nothing special about the story of it than the investor, Mike Leventhal who told me maybe we should find a new CEO, whose might lead investor for Mayfield apps at military. com, although we had gone through that difficult experience and we become friends and went together through (? 49:56).

(50:00)The sun is kind of setting and I just knew that we should stop and spend some time taking photos of all of these people interacting with the train. You know, they are putting their heads through the window, the light is amazing it’s a very kind of personal experience. And right behind me is the guy who terminated me from his company. So you can come full circle and you can end up loving these people that cause you some trauma earlier. Mike’s and incredible guy and you know, I will a lot to him.

Michael:         

(50:32) You know I just wanted to tell everybody who’s watching, we’re just running a little bit late and we are going to run over today, so I hope you’ll stay and continue watching.

(50:44) So these look like Tibetan, Tibet, Nepal and I saw some photos from Bhutan, so maybe Bhutan.

Chris:  

(50:49) Yeah, so it’s a little monastery and these are kind of young monks and we call them monklet’s, and you know, I’m just wondering up the stairs in the monastery and I see these three boys, and they are just sitting in the corner and I said you know – I had my camera out and I pointed my camera. I mostly ask people if I can take their photo, and this is what they do.

(51:18)They immediately go into some – I’m not cool enough to know what any of these poses of gangs symbols. I don’t know what they’re doing, but I found it quite ironic in ruderal Bhutan where there weren’t any tourists around and this is how they wanted to pose for me. So it was a kind of fun moment

(51:37)This is his Holiness.

Michael:         

(51:40) It’s a wonderful photograph. Look how happy he is.

Chris:  

(51:45) He’s happy all the time. I mean I have a long day at meeting entrepreneurs every hour and at the end of the day I am kind of grumpy and I can’t have any more coffee. This guy meets you know 1 million times more people than me and he’s been doing it for 70 years, and with each person he’s happy and engaged and never tired. You know, whatever potion he is using I want some of it.

(52:12)This is a kind of quirky photo I threw in here. This is right near the Prince’s yacht club, right by the golden gate bridge in San Francisco.

(52:20)You know, this guy doesn’t know I’m taking his photo. I just see a guy with a cowboy hat, and I just had this idea that it seemed just this photo kind of represented our manifestestity , you know the cowboy that came West and this is about as far as you can go, so the golden gate bridge which I kind of like the picture.

(52:44)This is my favorite sunrise picture. Anybody know where this is? It’s in Patagonia, southern Patagonia at a place called Torre’s Del Paine National Park in Chile. And what you can’t see behind me, you know there should be a show on like what is actually going on in the shot. So what’s behind me is a really cool hotel and this is 4:30 in the morning.

(53:18) And every day I would get up at like you know 2:30 or 3:30, because the sun doesn’t stay down very long because we are really in the southern latitude. And I would try to take pictures of the sunrise by these mountains. And every single day it was terrible. I couldn’t see anything. It was like one of those sunrises like did the sunrise, I can’t even tell, cloudy or whatever.

(53:38) And on the last day, you know it’s really a pain in the neck to get at this early every day when you are going to bed like at midnight after processing photos. And may be this photo has represented a bit of tenacity about Japan ownership, and on my last day I almost didn’t get up and I decided to get up and I went out there and waited for 40 minutes and I got this what I think is an incredible picture of a really spectacular sunrise.

(54:00) Sometimes you keep throwing yourself against the wall and occasionally it breaks down.

Michael:         

(54:06) Do you carry a tripod with you or is this handheld?

Chris:  

(54:11)This is not handheld, but what it is, is you know, from the talking about the tripod really what you’re saying is use any kind of stability system. And the stability system that I mostly use is that I put my camera on the ground. So this camera is probably sitting you know on the ground with my jacket underneath of it and I have got like a two second time. And I pushed the two second time and I’ll let go of the camera and I let it shoot. So that’s what’s going on.

Michael:         

(54:36) So that means you’re down on your belly, looking through the viewfinder on what could be very cold ground. 

Chris:  

(54:45) Yeah, I don’t care. I don’t know what other photos I have but this isn’t as cold as many of my photographs.

Michael:         

(54:54) Well it looks like that’s it. We’ve gone through.

Chris:  

(55:00)Well the other photos that are like South Pole pictures and you know, that’s cold, so that was nothing.

Michael:         

(55:07) And I love your penguin photos as well.

Chris:

(55:11)Thank you so much, who doesn’t love penguins.

Michael:         

(55:16) How can you not like penguins.

Chris:  

(55:22) I mean we can talk over a drink sometime, but you know when I was at least South Pole and the Emperor penguins are in a very unusual place and it’s hard to get to. I remember I arrived at this colony, and honestly the penguins just looked at me and all came over to say hi. They are cool creatures.

Michael:         

(55:39) Well so just before we go, can we talk photo camera stuff for a moment. Have you switched now from the Leica to the Sony A7S with Leica lenses?

Chris:  

(55:59) Well I guess I would save when we talk about cameras, you know I try to use the right tool for the right job. So that photo you just saw, I wouldn’t take that photo with a Leica. I would take that photo you know Nikon D800E or D10. So nature photography I think SLR is most appropriate.

(56:21) But the primary kind of photography I do is Street photography or portrait of people, and that’s where I’m using a Leica lens, a 15mm F.59 lens, really narrows the field. And with adapters you can put on a lot of bodies, and mostly I use an Leica M8 or Leica M9 or M240, but recently I’ve been using the Sony A7S and it’s a really incredible camera.

(56:44) And I’m kind of sad because I love my Leica body, it so beautiful, but this Sony A7S is probably the best little camera I’ve ever used. It shoots at high ISO, it works really well, the technology is great. The images come out great. Sony is doing some things right.

Michael:         

(57:02) Okay well Vala, we’re over time and we could go on for a long time.

Vala:   

(57:10) This may not have been episode 100, but one of my favorite episodes. Thank you so much, really really inspiring.

Chris:  

(57:20) I loved it, you guys are great. Thank you.

Michael:         

(57:22) You know, for us it’s the highlight of our week but usually what we like to do is gang up and taunt my glorious co-host – that’s not true.

Vala:   

(37:35) We’ll leave that for the weekend.

Michael:         

(57:39) Actually he taunts me. Well you have been watching episode number 98 of CXOTalk. And our guest today has been Chris Michel, who is a serial entrepreneur and he has invested in a bunch of companies and as you’ve seen is a really fabulous photographer. I’m Michael Krigsman with my glorious co-host Vala Afshar. Vala we are supposed to get like what another foot of snow here.

Vala:   

(58:09) It’s only six or 7 feet in the last month, no big deal.

Michael:         

(58:13) So my friendly and potentially snowed in co-host Vala Afshar, I’m Michael Krigsman thank you everybody for watching and we will see you next time on CXOTalk, Bye bye.

 

US Navy                                                                                                            www.usni.org

Founder                                                                                                           www.military.com

Affinity Labs                                                                                                    www.affinitylab.com

Monster                                                                                                           www.monster.com

Nautilus ventures                                                                                           www.nautilusventures.com

Harvard business school                                                                               www.hbs.edu

McKinsey                                                                                                          www.mckinsey.com

Software Arts and VisiCalc- Dan Bricklin                                                     www.bricklin.com

WordStar                                                                                                         www.wordstar.org

Microsoft                                                                                                         www.microsoft.com

Mercer Management Consultants                                                               www.oliverwyman.com

Facebook                                                                                                         www.facebook.com

Instagram                                                                                                        www.instagram.com

Whole Earth Catalogue                                                                                  www.wholeearth.com

Nikon                                                                                                                www.nikon.com

Sony                                                                                                                  www.sony.com

Leica                                                                                                                  www.Leica.com

Backroads                                                                                                        www.backroads.com

USA Today                                                                                                        www.usatoday.com

Book: Thin Book of Trust:                                                                               www.amazon.com/Thin-Trust-Essential-Primer-Building/dp/0966537394  

Davis–Monthan Air Force Base                                                                       www.dm.af.mil