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Caterina Fake

Hey everybody, how's it goin? I'm Chase Jarvis. Welcome to another episode of Chase Jarvis Live here on Creative Live. You're tuned into 30 Days of Genius series. That's where I sit down with the world's top creatives, entrepreneurs and thought leaders and extract valuable, actionable insights that you can apply to your day to day to help you live your dreams in career, hobby, and life. If you're new to this series, all you gotta do is go to creativelive.com/30daysfogenius. The number 3-0 days of genius. Click that blue button and then you'll get one of these awesome videos in you inbox everyday for 30 days. My guest today, you will know here from her list of accomplishments. It's too long to go through, but I'm gonna give you three high points right now. She was the founder of Flickr which was the world's first real photo sharing site that had sort of community and creativity at its core. Kicked off the web 2.0 photo sharing world. She was the chairwoman at Etsy. Took that company pub...

lic in 2015 and she was one of Times most 100 influential people on the planet. That's nuts. We're gonna talk about that. My guest today is none other that Caterina Fake. Yay. Thank you so much. It's great to be here. Appreciate it. (intense music) (applause) They love you. Thank you so much for being here. I haven't talked in like I don't know, like six or 12 months. Six or 12 months. That sounds about right. How are you? I'm doing really well. Doing really well. I'm so grateful. I mean, first of all I think of you as my friend, Caterina. Used to be on the board of Creative Live and now I'm in preparation for this show, I'm like reading about you. I didn't, I had no idea, this Time 100 most influential people in the world. What? How does that happen? When I got that invitation to that event, it knocked me over. It knocked me over. It was an amazing thing. But I mean, I don't know. I had no idea. Who else was at that party, speaking of party? So that is, that was (mumbling) name droppy, but. Just to name drop, just to name drop just a little bit. I mean I was at this party, and I'm wandering around and I'm sitting at a table with Condoleeza Rice and Rachael Ray and the guy who, I forget his name, wrote The Office. I mean, it was like sports stars. It was just unbelievable. And the mix of people was just amazing. Amazing, amazing. Instead of going down, that's I think a really interesting path for how you would end up there. Instead of going on the name dropper side, which I invited that, but let's talk, because that's, again, you're a, I think of you as a creator, as a designer, as a builder of companies. Yes. And the fact that your sort of pursuing your passion and then you can end up as one of the most influential people on the planet according to a very reliable source. How does that happen? What's the path there? That's the part that-- Well it's not really, yeah it's funny because you hear that all the time. You know, do the thing that you care about and it doesn't seem like it's actually true until then you find yourself at these things. And so it really, it really takes a certain kind of conviction, I think, in what you are, who you are, what you care about, what you're gonna pursue and the confidence to through decades even, decades even, of nobody caring, nobody noticing you. Nobody really being behind you. You're not showing any of the signs of success along the way. In fact if you looked at my high school graduating class, I would not be the one. (laughing) I would not be the one that you would've picked out as being on the cover of News Week. Like, I'm, that just wasn't looking that way. But the thing that, the thing that I had I think that kind of carried me through all of that was a very strong inner conviction that I knew who I was, I knew what I wanted. I didn't care about external rewards. The kinds of things I get. I never got per-- Chased money or fame. Chased money or fame or you know, you know even good grades in school. It was not something I was trying. So like I was one of the kids that you know, I knew I was smart, but I didn't care about the grades because I didn't, I kind of knew that they weren't really saying very much about me. Yeah, a measure of worth. Or a measure of aptitude. Yeah and so, and so you know, I was, I don't even know where I was. Like middle of my class. (laughing) Ish. Somewhere-ish. And yet I had all these side projects. I had all these things I was very passionate about. I worked on the side. I really cared about you know these, it was undefinable. Making. Making things, creativity, self expression. I was a writer. I was a painter. I was a photographer. I did all of these creative activities not knowing where they were gonna lead me. Not having any idea. I think that's so refreshing. I have talked throughout this series and for the five year history of this show about sort of two groups of people. A group of people that identify as creative and so like, all right I know I've got my start here and I needed to get better. So those are the group that I call going from one to ten. Like getting better at your craft and figuring out who you are and what you wanna do. And there's also the group from zero to one. And that's the group that is doing something else. Something that the world has prescribed for them rather than the thing that they were supposed to be doing in life or that their next calling. And in both groups, what I find a commonality having talked to a lot of really successful people like yourself and interacting with my community of people on Creative Live and people who are aspiring, that you think that there is some sort of a prescription. That you have to do this and this and this. And one of the things that's exciting to me is that today there is no path. Or there's rather a thousand paths to any end. So what I'd like to do now is explore a little bit. You talked about finding your way in school and maybe not being one of the best students, but can we go back and pull on the thread of what, like a sequence of steps that you went through and how you ended up at this, say this Time 100's Most Influential People. We'll use that thread. How did you get there? Yeah and the goal of this story I guess, is to under pin that there are a million paths and that there isn't one prescription other than follow your heart. So let's talk about early creation for you. You talked about being a photographer, a painter, a designer. But let's go into career trajectory. Like what are some of the things that you did? Were you a designer, a dancer? Like what was your, what were your, what's your trajectory? So when you graduated from college, I had a degree in English Literature and it was not a sequential career path. I took time off. I took my sophomore year off to write a book. I was writing a novel. Then I switched schools. I went to art school in New York at Parsons. I didn't like art school. I left art school. I ended up graduating from Vassar, but I kind of took a winding path. It wasn't a straight path at all through college. And then when I graduated, I had so many odd jobs. I was a, I was for example, I was a clerk at dive shop in Arkansas. In Arkansas? In Arkansas. Is there water in Arkansas. It is a land locked state indeed, but there, but there's the White River was dammed and so there's big lakes there so you can go spear fishing and so there's diving there. I worked at a law firm. I worked, I had odd jobs. I was all odd jobs. But what I was working for was that I would, I would work really intensely for a short period of time, and then I would strap on a backpack and head off to say South America or somewhere and then backpack around for six months. Then I'd come back and I'd work. And my parents were being driven up the wall by this. Here I am like 22 years old. They just paid for all of my college education. What is all that for if all you're gonna do is like be a bum and backpack. Backpack, walk the earth. And wander the earth. And so that's where, that's what I was doing. And I was actually on my way to Napal where I was gonna go rock climbing. And stopped off to visit my sister who lived in San Francisco. I'm from the east coast. Got it. And so my sister lives here in San Francisco and I was visiting her and she, she was very tolerant. My trip kept on getting delayed and then delayed, and then finally canceled. And she let me camp out. San Francisco was cheap enough to have a spare bedroom in those days. So I camped out in my sister's spare bedroom and just hung out in San Francisco. And so then about six months later, my sister's a sweetheart. Wow, six months of couch surfing. Six months later she says, hey you know have you ever thought of, have you ever thought of maybe getting a job? (laughing) So I said, what am I equipped to do? Not much, right? I have this kind of like, very patchy resume. All those kinds of things. But the most interesting that was going on at the time, this was 1994 and that end of I had been doing a temp job at Columbia University and I saw this thing, the Mosaic Browser. And I knew that the most interesting thing going on in San Francisco was technology. And so I started doing CD Rom design. Which is the, I kind of figured I could parlay my artistic aesthetic skills into some kind of graphic design thing. Not knowing anything about it. Never studied graphic design and knew nothing about it. But I kind of felt like oh I have good instincts in this regard. I can, I'll figure it out. And so I started doing these sort of CD Roms, designing them in director. And then got a job at one of the very first web design agencies. It was one of those interviews where nobody knew how to write HTML in those days. So I came in and they said can you write HTML? And I was like, yeah sure. (laughing) Great, you're hired. And so panicking over the weekend. I was like, okay I start this job on Monday. I need to learn how to write HTML by Monday. I didn't even have a computer. So I get down to my sister's office down in you know, Menlo Park and I was like, just on her computer teaching myself HTML over the weekend. By the time I showed up Monday, I kind of knew what I was doing. You could fudge your way through it. Then there was a couple days of training and you stayed up all night to figure it out. So it was like that, but you know I kind of had this sense that you know, I don't know it now but I'll know it soon. And you know this sort of sense of being able to teach yourself. Autodidact. Just autodidactism. Being able to learn on your own. And if you can learn anything on your own. Which you can these days. I mean look, here we are. Here we are. And I'm a huge believer in that. If you're passionate about something and you wanna learn it, you can, you will. So true, so true. It's a thing that kind of baffles me. Because to like, just to skip ahead, I worked as a designer for a few years and then I, I had, I don't know if anybody remembers this anymore, but in 2000, 2001 there was like a tech crash. It was like there was a tech boom and then there was a tech bust. The dot com bomb. The dot com bomb, like the, and things had started looking pretty dire. So I said you know, I wanna go back to my roots as a creative person and start a different business. Non-internet business. So I went and I took a I found myself an internship. Basically I just, I said, I wanna make handbags. I decided I was not able to make clothes, but I wanted to work with materials and do creative things like that. So I, but I knew nothing about it. I had never even worked retail. Like I never, I knew nothing about this business. So you're just following your instincts like handbags and the next thing. Handbags so I'm like. We're gonna make hundreds here. So I'm gonna make handbags and I called around to everyone in town. Left messages, every clothing company that I could find in the phone book. And one person called me back and I said, I will work for you for free three days a week for two months, if I can just attend all of your meetings and spend one hour a week asking questions. So totally did this, like try to figure it out on my own. So by the end of two months, I kind knew of how to source fabrics, how to organize a sales pitch to Bloomingdale's. How to you know, where the sewing comes from. How to manage a staff. Retail, all these things. And just from those two months and I just asked questions. I went to all the meetings. I just like watched. And of course all the shop girls were like kicking me around and I was like steaming the clothes. And it was like not a glamorous job by any stretch of the imagination, but I learned so much. And then I get out of there, and it's so funny because like I had all these friends who were fashion designers and they're calling me and asking me questions and I said, wait a second, this is all available. You just have to have the initiative and go out and you know, go out and figure out who knows what you need to learn and go find them. And then offer something to them. Yeah, that's the key right there because the people who know this stuff are very busy and what they need is help in something that they're either not good at or don't have the time for. And being of service, I think is a really key way to get in the door. Exactly, exactly. So handbags and then go to internet for me. So that never panned out because what ended up happening is we, while I was doing this, we kind of accidentally started this other company which eventually became Flickr. So I never got to make my handbag company. There's still time. There's still time, you can go back. There's still time. Make hundreds. So let's go to early Flickr. I don't claim many things, but I was really a part of the early, early community. Did the first iPhone app that shared photos to social networks. And that ended up being a pretty big paradigm. But one of the things that I looked at in order to do that was Flickr. It was a big inspiration to me. Talk to me about you know, conceptually, the idea of photos and cataloging them. And most importantly I think, building community. Well that's were I came from. My approach to the whole company was really from that community standpoint. When I got on the internet when I was a teenager, the whole thing was about connecting to other people. I was this lonely, kind of suburban, creative person in a town full of football players and cheerleaders. And I was just the artsy girl and I felt like I hadn't found my people. And the internet was this amazing way of connecting to people. Finding people that liked the same things that you did. And so I went on the internet with just this sense of people, community, connection. That was what it was all about. And in the early part of my career, I worked in, I worked on The Well. One of the very original online communities. I worked on Netscape's first online communities. I built a lot of these communities. Electric minds which was spun out of The Well. Community was my thing. That was the thing that I really cared about. And then blogging happened and I became a really early blogger and that community was very rich and you know, supportive. And really amazing people speaking in their own voice. I mean it was a magical thing to see all of that. To see all of that as it was happening. So the evolution into Flickr probably came out of all of that, all of that love of community and connecting people. And what better way to share your experience, easy, easy for those people who are not comfortable like with pros, than sharing photographs. We felt very strongly that this was a way that people could share their lives and communicate with one another and connect to each other using photography. So powerful. And the fact that there were, that photography really wasn't a thing. I mean it was a thing, but that's, my early career was about helping people understand photography because I looked at it as a black box. I wanted to figure it out. I did the same as you. Bang on all the doors. I want into this thing. This is really interesting and once you're in there, you're like, wow it's not that complicated and if I could start telling stories about what it's like to be here. What angle did you guys come at it? From the community part for sure. Photography is about, was it story telling and shared experience? Well what was happening, so many things were going on at that time on the internet. There were a bunch of things. So for example, more than half of American households in 2003 when we started it, had broadband. So that meant that they were not dial up. You know if remember dial up, but that was like drinking marmalade through a straw. Like you could just, like it was just no, there was no action there. And you just like wait for the, you could actually see the photograph downloading. Downloading like line at a time. Line at a time so it was really slow. So half of the US households on broadband. Huge thing. Another thing that happened around the same time, is that more than half of the cell phones were shipping with a camera. That was huge. Big deal. Big deal because everybody suddenly had access to photography and digital photography. You remember the days when a digital camera was wildly expensive. It cost thousands of dollars. We had one at the web design agency where I worked in my early days and it was this precious object a and it was like kept locked in this like file cabinet and you had to like sign it out. You know it was like this really precious and rare thing. Now they're on all the phones. So those kind of things happened. And also, a few things also socially had changed in that Friendster, if you remember Friendster. I do, oh my gosh. Had become incredibly popular and people got accustomed to making profiles of themselves online. And this was a novelty. Identity yeah, online. So like an online identity. Having a picture of yourself online was no longer a weird thing. Writing about yourself was no longer kind of odd. It was accepted. People understood what it was. And so all of these thing converge at the same time and Flickr was just hit it just right. Just right. You know and the tools were getting cheaper. Digital cameras were accessible to other people you know that didn't have all the expense of film, you know which was like an incredibly expensive thing. You know, buy the film, have it developed. It was much more complex. So fast forward a few years. Flickr grows wildly successful, you sell to Yahoo. Yup. And then you just peace out? You're like I'm done? Peace out. So while I was at Yahoo, it's so funny. When you're an entrepreneur you were like crazy hours and I was used to working-- That's what these dark circles under my eyes are. I see, yes. Working hard. (laughing) When you're an entrepreneur you work hard and after being acquired by Yahoo I was kind of amazed. I suddenly found myself in this situation where people were like going home at five o'clock. So I got an email from this guy Rob, Rob Kalin. Who said I started this new site. It's a marketplace for handmade goods and we'd love you to have a look at it. We really love Flickr and all those kind of things and would you put together a treasury which was basically like an album of all of your favorite things on Etsy. I said sure. So I looked at it and I loved the site. And so I ended up being you know, the first member of the board of directors. Helped them raise their first big round. And it was clearly a company. I mean, Rob, the founder, was one of those guys that you meet him and he says, he's this 23 year old guy, he's like covered in cat hair and like in this like dingy apartment in Brooklyn. And he sits there on the sofa and he says, yeah this is gonna be as big as Ebay, right? And you believe him, right? There's some people when you meet them, you say like is he the guy? Yeah, he's the guy. He can do it. Somehow I feel that you can do that. So anyway so Etsy was him, his two classmates from NYU, brought on another couple people. I mean it was just like five people. It was three and then it was five and then it was 20 and then you know, next thing you know like eight years later. It went public and has been, it's a wonderful company and the thing that drew me to it, is that the thing that I've always liked, and the thread that connects Flickr and Etsy, Kickstarter which I'm also and investor in Sundance, which I'm on the board of, the thing that connects all of these different businesses or non-profits is that they're a platform for getting people's work out there. For them to be able to find their own vision or voice or story and tell it. And all of them, Flickr with photography, and Etsy with handmade products, and Kickstarter with whatever you wanna make an s-- Expression, yeah. It's just all, like there's this very strong thread that is part of that conviction that I had when I was sitting in my basement coloring and writing and doing photography and just making stuff. I just wanted to make stuff. I love that thread. I wanna go back now because you've said many things that are, it's very clear to me that you were self aware and that you knew, you had some confidence that the things that you were do, that were doing or would do were intrinsically valuable. When I talk to the creative community, that's the thing I feel like I have that. It was instinctive for me. But I think for a lot of folks out there, it's not. So let's pretend like, I don't wanna go, get too preachy, but any advice for the folks that like intuition has been such a strong piece for so many people that have sat on the couch that you're sitting in right now. Can you talk to me about that for a little bit? Well there's so many things that are designed to train you out of it. Yeah. Right? You know teachers do not like creative children. I just put a blog post up. I have a new blog at the creativehours.com which is a big, which is. You should check it because it's like We will, I'm happy. The Creative Hours. It's completely your topic, The Creative Hours. And one of the articles that I had read recently, which I wrote about on the blog was that teachers give a lot of lip service to loving creativity. They love it. They're like, they love creativity. They really wanna encourage it in their students. All that kind of stuff. But when you survey them and say who are you best students, it's always the one who cross the T's and dot the I's. If you look at a personality profile of creative people that are usually kind of restless, they're a little bit unsettled, they question things. They're you know, even if they're not questioning it on the outside, they're questioning it on the inside. And the teachers reward the conformist behavior and there are so many paths in life that are. You know my parents wanted me to a lawyer. They wanted me to be going to you know whatever, banking. I mean, they really, I was not going the path that they wanted me to go and I was constantly being steered back onto that path. And it's very hard to resist because there's so many rewards, there so many things and-- Socially from your parents to your friends, to what you see in pop culture all that stuff. I mean like it's funny because like going into startups and being and entrepreneur has kind of become the investment banking of this era, right? It's so ironic. It's so weird. And so and yet, it's not the original creative impulse that drove you to do the things that you wanna do. And so the you know, if you find yourself on that path, right? I worked as an investment banker for like six months. I could not stand it. I could not stand it, I was fulfilling someone else's dreams and I left, I mean I left. And the other thing that I decided and it was actually very worthwhile. No matter how far you've gone down the wrong road, turn back. That is the advice somebody gave me once. If you've gone down the wrong road and you know you're on the wrong road and you're like in your last year of law school and you're like, I really don't wanna be lawyer. There's a lot of sunk costs in there, but you gotta take the true path. So I, I you know, we all find ourselves that-- That's fantastic advice. There's this concept of sunk cost. I'll be like, oh I'm already so far down this path, I might as well become. And this, the theme of sort of quitting or self reflection and finding out like what do I really wanna do in this world is such a common theme in the people I feel like, who are living their authentic self. Yes. There's a reader by the name of Michael Meade. He was here at Creative Live. I just made a little video with him. Great guy, story teller. He worked with everybody from the Dalai Lama to at risk gangs and this idea of your calling and it never being too late, it's always going to be there, but the worst thing in life would be to not pay attention to that. Yes. So you're in you're investment banking job or you're in your third year law school to take the point you just made, how to people reconcile, what is the-- Well it's so hard because like as, I really think that people are the same throughout their lives. You're the same Chase Jarvis that you were when you were 16. You have like the heart that you got, the heart that you got inside you is the same. Like what did you wanna be when you were a kid? You gotta listen to that. Who did you wanna be when you grew up, right? And the thing is I think that you're the same person as you were when you were 16, but as you get older you just take on more and more responsibility, right? You have to have a job, you have to pay your rent. You have like all of these obligations. You got your family. You gotta take care of people. And all of these things. The shoulds, that's what we call them. The shoulds, right? But like, and many of them you're not gonna be able to turn, you gotta take care of your spouse and your children and your family and your sick mom and like all of these people that are like depending on you. So there's so much that comes down on people and they've got a good, solid job and you know they're making it all work and it's so hard to listen to that inner voice. And so what you gotta do is if you're in that, if you're third year of law school or your like you know, 51 years old and like got teenage kids that you're putting through school. Whatever the thing is, you know, you got something on you, you need to make run for it. Just make that thing bigger and bigger inside you. That is the key thing that also I hear over and over is, that it's different than the societal picture. And that is that you find room for both things. It's what I thought you were gonna say, which I was gonna question was. So you just gotta stop doing all that stuff and then go do the thing. Can't do that. Because like you got, no life-- There are people, who yeah. There's living to do, right? There's all these things and you can't just like bust out and be like, see ya wife and kids. I'm like out. That's not something that you can do. So what you need to do is you need to like find that thing inside you and make it bigger and bigger and bigger. You start off, you take a class. You start off, you go to like a life drawing class, whatever your passion is. You know, you wanna do photography. You wanna, whatever the thing is. So you just, you just like make that part of your life bigger and bigger and bigger and bigger, but you preserve that. I hear also people say, I don't have time. I have three kids, I have a job, I have, you know the kids all have homework and they all have X and Y and, is there a message that you can give to that person? Well I had a teacher, I had a writing teacher in school, I wanted to be a writer, and I still wanna be a writer. I haven't lost it. Clearly, I love to hear that you're writing again. I'm writing, yeah. Which is super good. And he said, look, it's a page a day. You can do a page a day. You can be, it's like a half an hour for a page a day. And if you right a page a day, he said you are one of the most prolific, you're like Stephen King. Like you are one of the most prolific writers around. He like cranks out a book like every year. A page a day, think about it. 365 pages? That's a book. That's a book. So half an hour, you gotta squeeze it in. And you do it everyday. Like I just discovered that my Google inbox actually has this little thing where you can like do your goals and I that's when I started writing again. I put this little goal in my calendar and it would just like fit it into my calender, somewhere. Half an hour somewhere. And it would just like fit it in. Like oh you have a half an hour between this meeting and that meeting. Boom, you're gonna like be writing. So it's really, you just have to make. And it doesn't have to be that big of a commitment. And I like the idea of starting small because it usurps this big, a big roadblock for so many people. Like oh my gosh, how am I going to become a writer, when I've got, clearly I've got all these responsibilities and that you know, 15, 20 minutes. One page, a hundred words. I have through the course of living my life ended up in large part being a career counselor because I, one of those, I got one of the lucky few who latches onto their passion and pull on that thread. And I can hear in someone's voice if that there, if there's a story going on of their dreams are possible or they're not possible. And the story is, it's very clear and ultimately the people who for whom the story is not, or for whom the story says it's not possible because I have all these other responsibilities, I have never, I have personally never sat down and talked to them face to face and changed their mind. They always have to go away and realize and actually either want it bad enough where the pain of the thing that they're doing relative to the thing that they were called to do is bad enough that they will ultimately find their way either back to me or more importantly, to that true calling where they believe, they don't have to become the chairwoman of Etsy or own a design shop in New York. But they come back and they say I'm willing to stop telling myself the story that it's not possible and start telling my story, myself the story that I can write a page a day. Yeah. And it's when they do that, that first step. That's the zero to one. Whether they're an accountant or whether they're doing something they weren't, that they don't love and they start writing a page a day. That's the seed that can turn into something bigger. There's this other blog post that I recently wrote on The Creative Hours which was about something that I heard in a lecture from Dennis Johnson. Dennis Johnson is a writer. He won the National Book Award, he's written all these famous books. Jesus' Son, which was made into a movie, it was based on his books. I mean there's so many like wonderful books that he's written. He's a very crazy, interesting, dark writer. But the thing that he said. He was being interviewed on stage by Dave Eggers and this is in 2003. And I remember this really vividly. He got asked the inevitable question. What is your advice for young writers? And you know what he said? It was so weird. He said move somewhere cheap. I was like, that? Really? Like all (laughing). Everybody in the audience is sitting there and they've moved from like way out of nowhere Iowa, to San Francisco, into New York, into Los Angeles, to all of these very expensive places. In order to be around the creative community and the creative people that they wanted to around because they were always the artsy kid in the basement like me. And so this was shocking to us and we're like how can that possibly be true because here we are. And he said, look like if you live in these expensive places you're gonna be spending all your time, you're gonna be spending all your time just making your rent. So go somewhere, you're gonna have to like cultivate a creative community and have people that are like you and talk to you have have the same sentiments that you do. And find them and connect to them very, very deeply, but live somewhere that where your rent is low because it's gonna take decades and you may never publish a great American novel. So if you're, if that's the sole thing that you wanna do in your life, you need to cut your expenses and move to Idaho, is where he lives. (laughing) So there's that too, it's like, you know. Yeah and taken either figuratively or literally, I think that in either case, it's a step towards making that thing that you've told yourself is not possible, toward making it possible. Just one step and that's the thing that, there's. I've seen it over and over. There's this cascading effect that happen when you realize that oh my god, I can write a hundred words a day or a page. Well you know, I couldn't even do that. So you know what I did? What? I went to index cards. (laughing) That's starting small right there. Right, I'm starting small. So like this and I was like, index cards. It's so unintimidating. It's like only that much paper. Its a blank page. I can write one word and fill up the page. Right? It's like this small. I started with index cards. I started with an index card. Really good book called The Writer's Time. That's beautiful. Actually read that, it's good. The Writer's Time. Let's talk about some, you personally here. So some personal habits. Some have come out in our conversation. Like writing everyday. You're back blogging again. Is there anything that you do everyday? Do you carve out specific time? Do you have a morning routine that you really finds, I mean we all have routines, but are the things that you feel like that you have learned to do for yourself that may translate to the folks at home? Well one thing that happened by accident when my daughter was born was that she liked to wake up at, God knows, like 6 AM, 7 AM. I am not a morning person. I am a night owl. I have always been a night owl and suddenly I had this little baby. There she was. She wanted her mommy. It was 6 AM, I had to be there. There you go. So I started, I mean, it was driving me crazy because like you know, all the new parents out there will tell you, it is sleep deprivation for months and maybe even years. And so I went into this weird sleep schedule. I went to sleep when she went to sleep like at eight or nine at night. And then I would wake up in the middle of night. I would be awake from two until five. I would be awake in the middle of the night. Nothing was going on. No one was up. No one's updating their social media. There's really like, nobody's calling. It was like this quiet, amazing time in the middle of the night. I saw all of this research that showed that this is how people used to sleep in pre-industrial age. They used to sleep in two shifts. They used to call it two sleeps. The first sleep, the second sleep. Fascinating. Wow. And I found that those hours in the middle of the night, you know this may not work for everybody, but were incredibly created because I was uninterrupted. And you know, you can kind of artificially create this. I read another thing on the internet that I subscribed to a for a really long time which was check your email twice a day. Schedule for 10AM and then again at 4PM and that's it. And pretty soon you'll like train all of your colleagues and the people that want you that those are times that you're gonna be responding to email. And it's almost like cloning yourself. It's unbelievable how productive you become if you just turn off all of those distractions. Like, I'm one of those people you know, was responsible for like all of the social media that's around you and yet, I was very determined to like fit it into these like, I went through this period. It was like a internet diet, where I would only go online for an hour a day. And I kept a little notebook in my pocket. You know how you're sitting there and you're talking to your friends and you're like, hey what was the name of the Beatles' third album, right? And what happens, you're like, grab your phone. These irrelevant things, right? And so what I would do, is I would keep a little notebook in my pocket for when I was next online. And then I would write down what was the Beatles' third? (laughing) I would like write it down. And then when I got online, I would go bang, bang, bang, bang, bang, bang, bang. When was this? Was this diet like 20 years ago? I did this. Or is recent? I did this, I do it periodically and then I fall out of, you know I fall out of practice and so I have to kind of reel it back up again. But, that was. Great practice. I mean, it was kind of an amazing thing. And it was literally like being twins. Like I had like so much time compared to everybody else who was all sitting there like, you know. Yeah I see people with their email all the time and just emails, come in, ding, and then they respond. Chat. Don't do chat, don't do like those emails. Like it'll make you crazy. Bundling like time to me is so critical and as a creative person, I thought for years that anything that was a schedule was the man trying to keep me down so I'm gonna live this unscheduled life and as soon as I started actually applying a little bit of schedule. Yeah. Just a, I mean not crazy rigor, but realize that if it's not on my calendar it's not gonna happen because there's a lot of inbound requirements and one of the things that I started putting on my calendar was 90 minute blocks to do the things, the big things in life for me. Yup. What's your schedule look like these days because I know you've got your hands in so many different things. How do you find the time? Well I mean, a lot of it is really regulating your energy is really the best thing to do. You know you've got certain things you gotta do. I'm gonna, I feel like the energy to like answer all those emails. Or I feel the energy to sit down and really do some think-y stuff like what's the five year plan. Yeah. Right? And so being sensitive to your own energy and like what do I feel like doing right now? Like right now I'm kind of tired. Why don't I read some articles that I've been meaning to read. Like a lean back thing. Yeah, I just need to like absorb and I'm not really thinking right now. I can't create anything right now. Like just take advantage of that time. Like have all of your things. Like oh, I've been meaning to read these articles. Maybe now is a good time when I'm not feeling like really energetic. And then other times you're like, I'm on fire. I'm gonna make the plan. I'm all ready to do it, you know? Like that. So you know, regulate your energy that way. You know and block off, that's a great thing that you do. Like I do that too. Block off huge parts of your calendar. Because if you don't make that time, no one's gonna make it for you. And if you don't write your own script of what you want in life, someone else will certainly write that for you. Right and like then look at all of the things. You know, this really great video that's online by Dave Frank, which is, I don't know if you have ever seen it but, he basically takes all of the days of your life and puts them in jelly beans. He's like, this is how many days you've got. You got this many days. And you know, this is your first year and this is how much time you're gonna spend sleeping and eating and grooming and hygiene and dadada. And then he puts this like little bunch of jelly beans and he's like, these are your free hours. What are you gonna do with them? You know, you've got these jelly beans. So figure out what are those things. Like a friend of mine sent me this video, and she said, her 16 year old son just completely, like watched that video and completely stopped watching video, like playing video games. He saw that video, he's like, oh my God, I've got only these jelly beans. This is all I've got left. I'm wasting them, like giving my jelly beans away. I'm giving it to, you know, Nintendo. And so this, this is like-- I love, Mark Cuban, it was a part, he'd been on the show part of the series. He's like, follow your effort. What is it that you are motivated to spend time on and when you realize that time is limited and you start looking at what, you know, Gary Vaynerchuk also, how is it possible that you're selling, you're saying you can't start this business or you can't create a side hustle or whatever, when you you watch three hours of Netflix a day. Like there's this, an intrinsic deal when you're looking at A, having so much time, only having so much time on you planet. If you look back and catalog your time over the course of week or two weeks and you're really honest with yourself about how do you spend time, it's just a surprising amount of it gets chucked. I also am not a TV person. I basically watch Silicon Valley which is 30 minutes a week. I haven't even seen that. Because I've-- And everybody tells me about it. It's hilarious. It's so great. And House of Cards when that's happening, but those are really the only two shows. And I can't remember ever watching a show and I did that very instinctively because like, that's so much time, so much time to burn your dreams in front of the screen. Yeah, yeah. And it's a little, it was a little bit, like it was awakening when I starter in college, spending my time around a lot of other people. I had roommates and watching that was a very, it was an awakening for me like, oh God I gotta, I only go so many jelly beans. You only got so many jelly beans. So true. So what's on your jelly bean, like what are you spending your jelly beans on right now? So I have another startup. I am doing Findery. I am about to launch a new company which we can't announce yet. Damn But very soon. Okay. It's gonna be around all of the same things that I love, you know, you know? You kind of-- Of course, discovery, internet, creativity. Internet, creativity, self expression, people, storytelling. That's kind of my, that's kind of my sweet spot and those are the things that I really care about. And you know, when I left that really high paying job. I gotta tell you how I got that investment banking job. I was writing a novel and I decided that the best way to do that was to be a receptionist. And so I was a receptionist at this investment bank and-- (whispering) And you know, because you could sit there for like eight hours a day. Hacking the system. Right, because like I don't know, I had to let people in every now and then and call and say dadada. You're on your keyboard. No one knows what you're writing. So I was writing a novel. I'm like sitting there behind the reception desk and the managing director of the bank is like, hey you're really sharp, you know, you could be an investment banker too. And of course I'm making like nine dollars an hour so, I'm like I am an artist. This is not, I don't wanna be an investment banker. It's never been in the cards for me. My parents would love it, but. And he said, yeah but I'm gonna pay you $125,000 a year. And I was like, my jaw fell on the ground. I was like what? I'm like making, I don't know. I was like I don't know how much I was making. Like what 15? What's nine dollars an hour? And I was like, I was living in New York, it was $20,000 a year or something. And so I was like, I'll take that job. So I went and I got myself like some fancy shoes and I got myself a suit and I was like going. I hated myself, right? (laughing) Overnight an investment banker? Did that turn into self loathing and then you're-- Self loathing and then like I'm walking down the street and like all the people that like, people in wall street, they care about money. They care about money so much and I was like this is not what I care about. This is not what I care about. So let's talk about that for second. What's another, to reference Micheal Meade, he talks about the, you have your true calling in life, this thing that you light up when you do and that takes different paths, but there is always something that if you were aligned with your true authentic self, that you could be doing right now that would just be, it would be full of self expression, and all these things. And yet we have so many negative cues. We talked about it earlier. As a parent, as so many people who are listening are parents and the like, you know it was question that someone asked Michael yesterday. It's like, I'm a parent. What do I do because I want my kids to turn out well and I want to be supportive at the same time, but there are terms in our culture like starving artists, like deadbeat, like all these things that, that are cultural constraints. You're a parent. Yup. Sitting right over there. Yeah. How do you think about this, like encouraging your kids to be and do the things that they were supposed to do. Well you don't want them to destitute. You don't want anybody to be destitute. And you may have to have a day-- May require tough love. You may have to have your day job. Like your day job may be what keeps you afloat. But you know, you have to feed your spirit too. So you know, you don't wanna have like starving artists. You know, you don't wanna be somebody destitute. You don't wanna be poor and miserable and there's so much romance about that. Yeah. But you know, about the struggles and the miseries of the artist. But you know, we are a very rich country. I mean it is really, I mean, when you look at all of the things that people need, it's not really, those things are not really needs. You know, like. Cars and clothes and fancy apartments. Cars and clothes. Like if you have a hand me down phone that lasts you for five years, like awesome. You know, like. Relative to the rest of the, as soon start traveling. Relative to the rest. When you start like kind of like really looking at it. However, you don't want destitution. So you know I think that it's important for kids to know how to earn a living. It's really important to raise kids to know how to earn a living. And how to be responsible and show up for work on time and be responsible to others. And all of those things are incredibly important. But you're clearly taking an alternative path with your daughter. Yes, yes. I mean, we're so. We are homeschooling and my daughter's been homeschooled since she was pretty much born. I have, as you can see I'm like a big believer in learning, teaching yourself, like autodidactism. And that like taking it you know, as far as it can go. I am a true believer in that. And really believe that your you know, your passions and your curiosity will drive you through life. And that in this day and age there's so many things. There's Creative Live and online learning as just blossomed. Homeschooling is growing at an extreme rate. There are so many ways of connecting with other people and classes that are out there. I'm an investor in a company called Out School which has offers, which offers classes. I mean, there's really so many homeschooling resources and things that are out there right now that anything you wanna learn, you can. I got in a, an online discussion, actually it started in SnapChat and then I moved it out into some of my other platforms. And it's the first time in the history of the world where doing the traditional thing is probably actually more risky than following your passion. Yeah. And I see so many people signed up to do the things that other people want them to do. And what leads to is not taking care of your body, not taking care of your mind, sort of misery and then misery loves company. And so you end up being, if you're in the average, the five people you spend the most time with and you're in a job that you don't love around people that take energy from you instead of giving you energy. Like what's the price of that? If that's the traditional path and there's so many alternatives, ones like you just named, homeschooling and the fact that you can ultimately, if you have access to the internet, teach yourself something or you can go do these internships. Even as a 51 year old, you might be able to go and volunteer your time in something that makes you come alive. To do anything but that seems so risky to me. Am I crazy? Yeah because there's very little job security these days and you know, things change so rapidly. And industries kind of come and go. I mean, it's really, it is a very unstable world. I mean, it's just through the nature of our world. Our, you know, the current way that people work. And you know, in the medieval era you were born a peasant, you would die a peasant, everybody. (laughing) It was like the seasons would pass. Everybody did the same things that everybody had been doing for like 10 generations. And now it's just there's, change is, change is basically part of. It's the only thing that's consistent. It's the only thing that's going. Yeah, it's the only thing that's consistent is perpetual change and you have to be able to adapt and you know, go with the flow. And things are gonna be different and pretty soon we're not gonna have cars anymore. It's a kind of an amazing, I mean, I really think that actually. Cars are kind going in, will be all self driving. Going the way of the dodo. Going away. So we talked a little bit about you, your background, a lot of that, some of your personal habits. I would like just maybe a little bit of a speed round. So if you could tell me something about yourself that if other people knew they would be surprised. So what about you is a little bit of a secret that people would say, no way I can't believe that. So me personally a perfection-- My daughter can probably say something to this effect. Because so much has been written about you. You have written prolifically, but there are few things I'm sure that I'll give you a couple examples. Gary Vaynerchuk who's been on here talked about being really adverse to conflict yet he's so loud and boisterous. He's always on stage calling people out and everything, but he said a one on one conflict, I'm really, I'm really uncomfortable. Anything like that for you? Oh, interesting. I think I'm actually one of the most reclusive extroverts that you've ever met. So I'm a very extroverted person. I love to get up on a stage in front of a thousand people, give a talk. I like that, I really do. I like to give a talk, like being here. Yeah, being on TV. Being on TV. And yet, I'm such a homebody. I like to stay at home. I like to keep my slippers on. I like to like stay in bath robe until noon. I like to stay at home. (laughing) And my friend said you know, I always, she said, my goal in life was always to be like a very fulfilled and happy and productive person who was able to be in her pajamas all day. And I was like, that's a good thing to aspire to. Take that, yeah. Ring that bell, ding. So you know that, I kind of relate to that because I honestly think that online sociality is really suited for kind of reclusive extroverts like me. There's also these incredibly gregarious introverts too who are like always out and like always going to events and all these kinds of things, but. Yeah I think there's a misunderstanding about the term introvert and extrovert. It's really where you get your energy from. Like do you get energy from being external or do you get energy from being internal. So that's where you can be an internal, or an internal extrovert or an external introvert. An introvert and so on. Yeah. That's really, I would not have pegged that. Yeah, I'm a homebody. I like my slippers. (laughing) You've probably heard the question like what would you tell your 20 year old self. I don't really wanna go there. I wanna know, what did you learn yesterday. Something that you learned yesterday. Yesterday. As proof point that we're always learning. Oh my goodness, you know what I started doing yesterday which was kind of an amazing thing, was I started, I mean, when I say that I started blogging again, I literally mean day before yesterday, right? Wow. And are you gonna write every day? Is that the-- So I've been trying, so what I, I had this sudden burst of, this happens to you sometimes. Your like, I can write ten blog posts today, right? So I kind of felt like that. I was like, I'm gonna write ten. So I didn't write ten, but I wrote like four and I queued them all up and I put them on, like I scheduled them to be like blogging and I had forgotten about that. I had forgotten about these bursty kind of bits of creativity because I've been like plotting along, doing creative stuff. But like everyday, a little bit, little bit. And then you have like these wonderful explosions of super creative periods in your life and I had forgotten about that. So I like, you know, this kind of came out of nowhere and I was like wait, I can do this blogging thing. No problem. If I just do it in these bursty way, I can do it. Because like it's hard to like, everyday like. Yeah that's hard. I'm not inspired today, you know. I have writers block. I'm not thinking about, there's nothing interesting going on but if you write it all at once, you know, during these like massive explosions of creativity, you can get a lot done and it seems if you like space it out, it seems like, wow, this person is super productive. She's blogging everyday. Everyday, she started blogging once a week in her little seven posts. Right so that was you know, that was kind of a revelation to me. Because I, you know, when your life is like, your life kind of falls into these routines, it does. You just can't help it. I think it kind of is natural. You fall into these routines and habits and you know, dadadada. And then something jolts you out of it. It's like hallelujah. That's amazing. When you speak into that, that sounds like inspiration. Where do you take inspiration, you take inspiration? Is it from people or nature or technology or your internal voice or what are some of your core inspirations? So I'm a big reader. I've always been a big reader so I read everything. I've got a house full of books. Like ten books arrive on my doorstep. You know, it was really funny because I like, I was trying to plan for like how many bookshelves I need and so I like was like I read like this many books a year, right? I don't know how many that is. That's like 36 inches worth of books. I like read, you know, like I need this much shelf space. I'm also one of those people who has hard time like getting rid of them. Because oh yeah that one means so much to me. I love that book. Read that, I'm gonna read that book again. So I read, like I read so much. And I have just read two incredibly inspiring and moving and beautiful books. One of which is by the 2015 Nobel Laureate, who I picked up, Svetlana Alexievich who wrote a book called Chernobyl Prayer. Amazing, amazing stories. It's just full of these like just amazing stories from what happened. Not the official story, not even the people who are like actually participating in the clean up of Chernobyl, but everybody who was affected. I mean amazing stories, amazing stories. Okay that's one. That's one. I also read a book by Carmen Laforet who is a 23 year old writer, writing in like the 40s in Spain. She wrote a book called Nada which is amazing, crazy odd, interesting, gothic novel about her time there. And wait, what was the other one? Oh, Hungarian novel called The Door by Magda, I don't know how to pronounce it, it's a Hungarian name, Szabo. C-S-Z-A-B-O. Really amazing book. Highly recommend it. So that's just in the past week. I'm like a, you know, I just read those. Wow, while you're on a roll here, anything else that you wanna drop? Any other things that people should be reading? Be reading? Well my fav-- Oh you want me to go through like all my favorite writers. A couple yeah, that's good. I'm a huge lover of W. G. Sebald who is a German writer who tragically died young. He was just being translated into English and becoming better known here when he died in a bicycle accident. Wonderful writer. It's a kind of like travel logs and you know, all of that. I'm a huge fan of Vladimir Nabokov. I've read everything that he's written. So classics. I was actually a Shakespeare, I studied Shakespeare and I was a lit nerd. Like I was a literature geek. That's where I kind of came from and I read prolifically. I read you know, a lot of novels, I read a lot of non-fiction. I've been reading a lot of psychology lately. I've been very interested in James Hillman who was a follower of Carl Jung. And his work is incredibly good for people seeking their vocation. It is really fascinating because our psychology-- Say his name again. James Hillman. Okay because like people seeking their vocation is, again I've referenced Michael Meade three times now. Vocation is your calling. It's like that's what vocal-- That's literally what it means, vocation. Yeah, yeah. And so people are gonna wanna know about this. Tell me more. And what he talks about is like very similar to how you're describing it as like the thing inside you. He says that all of this psychology these days makes you feel as if like, your childhood is what caused you, right? And he kind of flips that. Like you know, you had this kind of childhood and these are the things that naturally kind of flowed out from like your experiences with, your parents were a certain way. Or you lived in this kind of community growing up or whatever and that kind of determined your path in life. But what he says is actually that you call it to you. You were born and he calls it like an acorn. You're both like this, you're like this acorn and you've got this potential that you've got inside you and that the people in your life were called to you because of the acorn that you had. You called those people into your life. You found these set of circumstances in order to become this thing that you were meant to become. And so it's kind of like it flips it backwards and it gives you much more egency and it gives you much more possibility than saying like, oh you know my dad was like really tough on me and like all that story, that narrative that you can kind of like make about your life. Instead you kind of reframe it and you think about it like what was my father here to teach me? Like what is it that my acorn was asking for? He's the guy who wrote a book called, I don't remember what it's called now. It's about the soul. He talks about the soul which nobody talks about anymore. He said the soul has gone out of psychology. It's kind of fascinating actually. It really has. You know, it's become like very much about, you know data and-- Science and data made. Science and like all this. It's a very rigid way of thinking. Where as, truly the flourishing of the soul is what we're seeking in our lives. And so that's what his books are about. I'm all over that. I think a good intro to his work is a book called The Blue Fire, or A Blue Fire which is a compilation of a lot of his writing. Sweet. Yeah, it's kind of rough going. It's like super academic. It's hard to read, it's slow going, but it's brilliant and inspiring. I love things where they're so dense, you can read a page or two and then have plenty of, Exactly. Plenty of time to think. I read it over last summer, like the book. I read like a couple pages and then I'm like, wow I'm gonna have to think about that. (laughing) I'm gonna have to take a long walk. I'll take a few days and I'll think about that and then I'll go back to it. And really it's like that. It's really, it's a great way of thinking. I think people, I'm fascinated by where people take their inspiration from and reading and the work of other people is like reference, use guides like Heler. Hillman. Hillman. Use reference like Hillman and, or think of it in terms of how Austin Kleon talks about it, steal like an artist. If you follow one person, that's stealing. If you follow everybody, that's research. And that's largely what these talks are supposed to be. There's supposed to be little seeds of inspiration so you can, the answer is not out there an many think. Everybody has a very idiosyncratic path. I'm sure you know maybe somebody in the other 30 people that you're interviewing are interested in James Hillman, or not. You know it's a very idiosyncratic path and there's things that you know, if Ramon's lyrics are where you get your inspiration then Ramon's lyrics will be what it is. So it's not, you know, there's no formula. And you tend to be like, I like that thing. Give me more of that. And people, why is it so hard to listen to that voice because everyone has that voice and we've spent, you know, we've talked about it a couple time already in this talk, there are so many things, whether they're parents who are thinking about what they want it to be and mapping that onto you and telling you to be an investment banker or where there are teacher who say that they give lip service to creativity and they really want you to just be the next science teacher or like there's so many competing voices. How do you pay attention to that inner voice? Because it's all about, you know, success. That is what it is. It's the drive to success that is killing people and is killing people's souls. And the way to be successful, people know that if you follow this path and you do these things and you follow this formula and you go to Stanford. You know, there's these very clear paths to success. And you know, I remember like reading a psychol, like a, the comment of a psychologist who worked in Palo Alto, where your, it's the the city full of the most successful people in the world in technology. It's amazing. He said so little success, so little happiness. And it's that drive to be successful. That actually leads you astray. That actually leads you astray. You wanna be successful. You wanna be a successful entrepreneur. You wanna be a successful artist. You wanna be a success and that is the thing that leads you astray. It's crazy. By flipping that, what is the thing then that does lead to success? What is the polar opposite of chasing success is? Because you can't like, you know, stop chasing prizes that you don't want you know? Like those prizes are out there. There's prizes, prizes, prizes, prizes, prizes. Everywhere you look there's prizes. You can see the prize. You know how to get to the prize. What should you be chasing instead? You have to be chasing this sense of what truly makes you happy and you know what it is and it's usually not money and success. And there's so much of our culture is wrapped around how to be successful. I mean it's really, it's really astonishing. And you know it's a, it's a hard thing. I mean, I am, you know it was really funny. I went into, I was doing an interview with Nick Bilton who was a reporter New York Times, yeah. For New York Times and I'm like going and they had a brand new skyscraper in Time Square. A beautiful building and I'm sitting there being interviewed by Nick Bilton of the New York Times and I'm saying like, you know. I had this like just weird vertigo. I said how like, I don't even really understand why I'm sitting here talking to you. Like how it is that I got here. And I think that the thing that was very clear to me when I was sitting, I remember when I was sitting, I remember very vividly this moment. I remember sitting and thinking that if I was just sitting alone in my room doing what I was doing without any of that, the external kind of accolades coming at me, I would still be happy. I would still be happy. What is that thing? And all of this stuff is accidental and it's honestly not, you know. Whatever, Flickr's a huge success and I like flew to Davos and I like sat around with like heads of state and like did all these kind of fancy things and I was like flying around on the Google Jet and like all this stuff, right? Which is cool and you can do it for like a certain amount of time but I remember having this conversation with my friend and I was supposed to go have dinner with Rupert Murdoch and his wife and some other famous people and I didn't wanna go. And my friend said, no, no, no, but Rupert Murdoch can help you with you business. I was like, no he can't. I really need like a really good graphic designer. He doesn't know a single one of them. I'd rather be hanging out in basements with like 20 year old graphic designers in Brooklyn than going to this like skyscraper. I don't like, really those things don't matter. And like you know, I've been fortunate enough. I mean, I've been very lucky. Very few people get the chance to like turn down invitations from Rupert. But like it's so true. Having done those things. Having done it. Like you come out the other end and you're like, well that was very fancy. I think it was Neil Strauss, Neil Strauss told me a story about Lionel Richie. And Lionel Richie in like his peak of the 80s just winning everything. Climbing the mountain is the story that he talks about. And then we he got to the top of the mountain, there was no one there. Exactly. And it really isn't to that destination. It's that journey, who are you spending your time with. What are the moments where you're doing the things that you're supposed to be doing, pursuing your passion. His passion, obviously, music and it was that path that was the reward. The success, the thing that you can stick a flag in on top of a mountain is lonely and not the thing. Yeah I mean, being surrounded by people that you love and you know, caring for them and loving and being loved. Those are like the most important things and everybody knows that. From being in your basement to all those different school paths. In and out of school, art school, not art school, investment banking, Vassar, starting a little internet site, becoming wealthy, chairman, chairwoman rather of Etsy and full circle here, the Time 100 Most Influential People on the planet. Yeah. All by just doing the things that felt good to you when you wake up in the morning. Yeah, yeah. I don't know a better way to end a interview. We went a little bit longer than I had told you we would, but I wanna say thank you so much for taking your time. Any advice or anything you wanna leave us with? No pressure. Well I mean, I think it's a, it's something that you have to do everyday and just start where you are with what you've got and the time you have. Thank you. All right everybody. Another one of these interviews in your inbox tomorrow. Thanks for tuning in. (slow techno music)