Design MBA

Investing to Buy Future Freedom - Craig Mod (Investor @ Figma, Designer Fund)

Episode Summary

"Whenever I got any kind of money, I would ask myself how can I invest this?" My guest today is Craig Mod who is a designer, writer, and angel investor in Figma. In this episode, we discuss Craig's early exposure to computers, moving to Silicon Valley, working at Flipboard, meeting Dylan Field, investing in Figma, living in Japan for less than $15,000 a year, writing essays to deliver value and build a following, investing in companies and building financial autonomy to walk away from things. For show notes, guest bio, and more, please visit: To learn how to launch your design side hustle, please visit my blog: Connect with me on LinkedIn:

Episode Notes

Craig Mod is a Japan-based author and photographer. His books include Kissa by Kissa, Koya Bound, and Art Space Tokyo. He is a MacDowell, VCCA, and Ragdale fellow. His writing and photography has appeared in Eater, The Atlantic, California Sunday Magazine, The New Yorker, and other publications. 



If you enjoyed this episode, please take a moment to leave a rating and review in Apple Podcasts, Spotify  or share the episode with a friend. Thank you! 💙

Episode Transcription

Namaste and welcome. This is Jayneil Dalal and you are listening to The Design MBA. This podcast is a real-life MBA program for designers where we interview design hustlers and learn the skills, mindset necessary for a designer to launch a business venture. You can learn more. Find past episodes and stay updated at


Jayneil Dalal: Today, I have a phenomenal guest with me, Craig Mod. Craig Mod is a Japan-based author and photographer. His books include Kissa By Kissa, Koya Bound, and Art Space Tokyo. He is a MacDowell, VCCA and Ragdale fellow. His writing and photography have appeared in Eater, The Atlantic, California Sunday Magazine, The New Yorker and other publications. This is just a short blurb for Craig Mod. He is a freaking amazing guy.


Craig, thank you so much for coming on the show, man. It means a lot to me.


Craig Mod:  Thanks for having me, man.


Jayneil: Yeah, one of the biggest challenges I had with interviewing you is usually it's the opposite is like I had to like dig, dig and find some interesting nuggets. With you, it was like “Damn! This guy has done so many cool things in such a short span.” I’m like “Where do I begin?” And what I want to start off with is I had no idea that you were a stock geek since the age of 15. How did that happen?


Craig:  I grew up in this very blue-collar town where basically there wasn't a lot of wealth. I grew up with my mother and my grandparents. My dad was off elsewhere and tiny house. My grandfather worked at the airplane factory and when he wasn't working there, he sold pens. And people around me, there wasn't this sense of wealth. And in high school, I remember kind of the stock market appearing on the radar and I was sort of a science geek and math geek and I just thought “Oh, this is interesting.” Not only is it interesting but it's like Robin Leach's lifestyles of the rich and famous. Everyone was like “You got to have a stock broker and buy stock.” I was like “All right.” There's literally no one in my near circle that has ever talked to a broker in their life let alone bought a stock. My grandparents were so afraid of things like the stock market. They're just savings accounts. This was back when a savings account could produce real returns. I mean, they had genuine interest rates kind of sitting behind them. Yeah, when I was 15, there was kind of a stock broker club thing in high school and we got like a thousand fake dollars and invested in some stocks and I was just kind of captivated by it. It was just really crazy to me that you could buy pieces of giant companies like GE. I mean, that was just amazing to me. Yeah, I was lucky in that sense to kind of get exposed to that. That was part of my ammo whenever I got any money, a couple hundred bucks for a birthday or whatever, I just immediately was like “How can I invest this? I didn't think about buying stuff. I kind of had this intuitive sense that to get out of whatever it was that was, I guess, defining the area I grew up in, in order to get out of there, I was going to need some strategies and I kind of intuited that perhaps stocks were one of the exit tools to kind of elevate myself outside of that town.


Jayneil: To a better life, I’d say.


Craig:  Well, to just a different place. I mean, I definitely had this impulse from when I was young to get out, to travel, to see the world, to kind of understand things a little more. I think part of that comes from being adopted and you just have this kind of implicit sense of the “true story” of who you are is unknown. And so, there's this weird psychology there with adoption where, especially if you don't obviously know your birth parents, that there's like “Oh, okay, there's this whole other story outside of what I know.” And so, that kind of pulls you in different directions.


Jayneil: And what was this town where you were raised?


Craig:  Hartford, Connecticut.


Jayneil: Oh wow!


Craig:  It's just funny because you don't think of Connecticut as having blue collar anything. Obviously, towards New York City, in the country, it's just all Maseratis, Yachts and people smoking golden pipes. And I didn't know that because my town was not that. And I went to university and I met other people from Connecticut and I was like “This is what Connecticut people look like from the outside.” And everyone I met at university; they were like “Where do you come from?” – “Connecticut.” They're like “Ooh! Did you come on a helicopter?” – “No, didn’t come on the helicopter.” So, that’s kind of amazing. My town was also extremely diverse. One of these things you when growing up, you don't really know how to value but my best friends in high school were Vietnamese and Indian. I think about the mix of people that I interacted with, not only just races but varying life experiences all within this kind of blue-collar-ish background. It was super rich. It was crazy. I mean, I’m very grateful for that experience.


Jayneil: I grew up for most of my life in Ahmedabad, Gujarat in India. And Ahmedabad, basically, was the birthplace of Mahatma Gandhi where he has his shelter too. So, I didn't get much exposure, I would say, until I want to say maybe 2010 or 2011 when I started traveling outside of India really and spending time with different cultures and different races. And then I was like “Oh man, this is a very different way of thinking.” Have you tried to like keep in touch with any of your Vietnamese and Indian friends from high school or university?


Craig:  Not a ton. I haven't been very good. I mean, they're sort of like tenuous connections on Facebook but I don't use Facebook. I haven't updated Facebook in five years probably. Not really a ton. I do wonder how some of those folks are doing but I haven't been good about keeping in touch with high school people for sure but also college people. I think part of it is just you end up having such a divergent experience compared to even people I went to college with and just kind of you keep evolving your little pocket of family in the world.


Jayneil: That's true. And from university, how did you end up at Flipboard or did you already plan “I was going to go to Silicon Valley and work there in a tech startup”?


Craig:  I started programming when I was about eight or nine. Even though there was some crazy stuff in my town, I was lucky enough to be kind of put into the “gifted program” and they had a computer. So, I’m going to be 40 in a couple months. So, this is the late ‘80s. I look 65. I feel 105. It was the late ‘80s. So, computers were like Commodores and funky weird Apples and stuff like that. my family couldn't in a million years afford a computer. So, I think, eventually we bought this weird Apple clone. You obviously don't remember but there's a very brief period where I think Sully was in charge and he okayed clones. So, IBM made PCs and then they allowed people to clone the IBM architecture or whatever. And so, Apple allowed this for a little while. You could buy these really crappy cheap clones and they're just horrible. I think we eventually could afford one of those but my neighbor who was divorced and lost his kid in the divorce, so I think was really lonely, he had a computer and thankfully, he wasn't a pedophile or anything. He was just a nice guy. I found out he had a computer and I was like “Ooh! Can I use it?” And I end up going over so much and annoying him, he just gave me the key to his house. He was like “Stop knocking. Just come in and use the computer.” And he bought me a phone line for the computer room and I got online and I started doing like BBs stuff in Prodigy. And just immediately, to me, as soon as I got on the world wide web which was like I had a shell account, you had to emulate a PPP socket to run a graphical browser, this is all Windows 3.1 or whatever, I just remember thinking as soon as I saw the web, I’m like “Oh yeah, obviously, this is it. Done. Okay, whatever we have to do to focus on this, let's do that.” And I was doing a bunch of IRC-NCR related work. And I was one of the younger folks in these NC crews. So, when I graduated high school, a bunch of these dudes, they were all mainly dudes, had graduated college and they were in California and they were starting little design agencies. This is the late ‘90s. And so, I was able to get internships through these connections I made when I was 13 because of my neighbor who was nice enough to lend me his computer and not do creepy things to me. It was a super wholesome setup and it's one of these things that makes you realize, one weird little gesture or one kind little gesture can have such a ripple effect in someone's life. And I actually went to go thank that guy. His name was Tom. I went to go think of a few years ago and he died of a heart attack. So, thanking people often and quickly is kind of the takeaway there.


So, I ended up driving across America four times in my late teens in this little Honda Civic that didn't have power anything. It was my great uncle's and he bought it and then basically passed away right after he bought it. I didn’t know you could buy a car with no power anything and no AC, nothing. It was basically a shell of a car. And we drove that across country four times and that was amazing to be able to just see America and get these little startups in basically Silicon Valley to pay for driving and gas and all that crap. So, already from late teens, I was doing a little web design company when I was like 15-16 in my hometown and doing 3D graphics and stuff like that. And then I went out to California for a couple summers and I was just like “This is fantastic.” And then when I studied abroad, I wanted to spend a year abroad somewhere, I came to Japan. And in the middle of that studying out here the first time, Silicon Valley collapsed, the first bubble popped. And so, I was going to drop out of school and just go work for startups and kind of hack it away in Silicon Valley and that happened and I thought “Well, all right, let me finish school instead.” And so, it was a circuitous route. This is the early 2000s. And then eventually, when I went to Flipboard, that was in 2010, so it was like 10 years after all that happened. And, basically, what sort of led to that was I had worked with everyone in Tokyo that I was inspired by. I had sort of hunted down when I was 27, 28, 29 the people that were most inspiring to me and working on a global scale in Tokyo. And we started collaborating and I hit this kind of natural ceiling. And the next step, in terms of working with even higher-level people operating at a bigger scale wants to go to Silicon Valley. And connections I made in my early 20s with this guy Marcos Westcamp, he messaged me and said “Hey, man, I’m working at this startup. You should come talk to the CEO. I can't tell you what it is but I think you'd like it.” And so, I went out there, met with mike McHugh and within literally 30 seconds, I was like “Okay, I’m going to move out here and work with these guys.” So, it took a decade. That was the path, that was the destiny, a decade later.


Jayneil:  A decade later. Oh my God. And there, you also end up meeting Dylan who then goes on to start Figma. That is insane.


Craig:  Oh, hell yeah. Dylan was 18, maybe 19. I don't know. I don't think he was yet 20. No, he couldn't have been. I bet he was 18 when he was interning at Flipboard. And with Dylan, it was just immediately like “This guy's is just a good soul.” I mean, talk about lucky, that guy had kind of a charmed childhood in terms of access to amazing people, to the great archetypes. And I think he's a wonderful example of how emotionally intelligent you can kind of … You can prep someone with a certain amount of emotional intelligence early on. And I feel like Dylan is much older emotionally than he is, obviously, temporarily or whatever. And it was just kind of amazing meeting him. I was like “Oh wow! This 18-year-old has so much wisdom.” Very weird. I was like “What's going on here?” but so amazing to see him succeed. And he and Figma truly is just killer. It's just such a killer app. I love it.


Jayneil:  A couple of things I’m thinking about is now that you made the connection with Dylan. You could have potentially joined them at Figma and then you also were the recipient of that Tech Fellows Scholarship where you can just invest that grant into startups. So, did you think about like “Hey, I met Dylan. He's going to maybe start a new company. Why don't I just take the grant and invest that in Figma?”


Craig:  Tech Fellows thing was so weird. I don't know what happened to any of the money or the people. I have no idea what's going on. I got an email one day. It was just like “Hey, you've been selected to get 100,000 dollars.” I was like “What?” I mean, it was pure Silicon Valley like bizarreness. They handed out two million dollars to a bunch of random ... Anyway, it was very strange. The Tech Fellows money and Figma being started, I don't think, happened at the same time but full disclosure, I’m actually an investor in Figma.


Jayneil:  Oh wow! I did not know that.


Craig:  I just invested my own money instead of Tech Fellows. So, I was an angel and I did a prorate and one of the seed rounds.


Jayneil:  Holy shit! That is insane. Oh my God.


Craig:  That's definitely totally connected to being 15 and thinking about stocks back then. And thinking about investments, I have extra cash, one weird thing I think because I grew up with not a lot of material possessions is that I am extremely suspicious of material crap. I’m very, very, very suspicious. I’ve always been suspicious of owning too much, having too high a baseline cost of living yeah. I’ve been in Japan essentially for 20 years. And for most of the time I’ve lived here, I’ve never paid more than 800 dollars a month in rent. And the first five or six years that I was living here, my yearly cost of living was essentially 15,000 dollars. It was for food and lodging. And I wouldn't buy clothes. To me, any extra money was an opportunity to invest in the ability to have freedom later on through doing stock investments, saving, and then taking that money out or selling stocks when you need it. You don't try to time the market. That's just being an idiot. It's like I have this project that I need to work on and when I was 25, I probably had about 40,000 or 50,000 dollars saved in various stocks. It would pain me but I’d be like “All right, I need a thousand bucks to do this experiment or this project or make it work on this book” and I would sort of pull from that. So, by the time I’m in my 30s, I’m in Silicon Valley doing investments like that for friends, with friends or for companies I believed in. I was also an early investor in Timbuktu which did the book Good Night Stories for Rebel Girls which is the most crowdfunded book ever and they went on to do a couple of other books. They're all million-copy bestsellers. Elena and Francesca were just these two incredible women. You met up with them. It was just obvious these women were going to be successful and they were going to work on great impactful meaningful projects. And because I had started building up this habit of investment from when I was like 15 and this habit of … I made more money in one year working at Flipboard than I did in basically 10 years of working up to Flipboard.


Jayneil:  Oh wow!


Craig:  So, I was basically a monk coming out of a cave in India into Silicon Valley in terms of my burn rate. And even when I moved to Palo Alto, I lived with two other guys. And in 2010, Palo Alto still sort of reasonably … Again, my burn rate in Palo Alto was almost nothing. And so, I had savings from the work. I was just socking all that money away. So, whenever these opportunities came up to support someone I totally believed in, it was like “Okay, great. Instead of putting this in the public market, let's start diversifying into these private markets.” And that was what led to that work.


Jayneil:  And it's insane that you're also an investor in Designer Fund like Ben. Oh my God, these guys are so amazing. I had a chance to meet Ben when I was in SF. Oh my God.


Craig:  Enrique was my roommate for three years.


Jayneil:  No way!


Craig:  I love Enrique to bits, man. He's like a mentor. He taught me how to hug again. I moved in with Enrique and I got more hugs in a week than I had in about a decade.


Jayneil:  Oh my God.


Craig:  I was just like “Ah, this is what I’ve been missing in life. Hugs, super amazing, beautiful bro hugs. So good.” And then hummus, all we ate was hummus. Our entire refrigerator was just full of hummus. It was such a weird three years, man. We cranked like crazy. That was one of the most beautiful, love-filled, work-filled, “Let's be better. How do we make each other better” periods of life? Life changing, going and moving to Palo Alto and living with those guys, absolutely. Just incredible. Enrique Allen. And Ben Henry, I think, was the other guy. And Ben is this amazing filmmaker and he was just cranking away too. And Enrique and I were basically brainstorming Designer Fund in the kitchen nightly. I’d come back from Flipboard and we'd just riff on stuff. So, again, when I saw he was going to do that, I was totally behind it. They actually made a very generous offer for me to join as a partner but this is right when I was trying to figure out what my next steps were and I wanted to just focus on writing and I wanted to focus on a lot of the stuff that I’m doing now. And so, I said no which is kind of crazy. I found their offer letter the other day in Dropbox Paper. It's the only document there. And I was looking and it and I was just like “Jesus, man, this is so generous” but I had this very clear pull of what I wanted to be doing and I knew that I couldn't do that if I joined somewhere full-time. And so, I said “Look, I want to be involved as much as I can and support you guys as much as I can. Please, use me in any way you want but I can't do a full-time thing.”


Jayneil:  Wow! So, what does your day look like? Do you have a structured day? I mean, you're doing so many things. You're doing your writing. You have all these angel investments. You're a mentor to startups. So, is there like a process?


Craig:  So, the investing stuff I really have cut back on almost completely. So, I was most active as an angel investor in 2010, 2011, 2012, 2013, 2014 basically. And then a big part of what was attractive about Designer Fund was becoming a limited partner there. And, as you know, most of investing is about deal flow and about connections. If you're not in Silicon Valley meeting people and connecting with people, then angel investing just doesn't make sense. And it was kind of interesting but not sort of a lot of work. You end up losing quite a bit of money. You have to be willing to watch your money evaporate. And so, Designer Fund, for me, is sort of my proxy my investing proxy and I trust them with the deal flow and I can chime in and I can direct. If I meet someone who's doing a company and looking for funding, I can push them in the direction of the Designer Fund and say “Hey, talk with Enrique and Ben. See what they have to say.” So, I don't really do any active private investing at all anymore. So, that has almost no play. Maybe 10 minutes out of the year I spend on that but otherwise, my daily schedule is really contingent on the projects that I’m working on at that moment. So, for the last couple of months, it's been book design, production, editing, essentially setting up a publishing machine. I don't want to say publishing company because it's just my own work. So, it's like this machine I’m trying to set up with fulfillment, shipping, logistics, all that stuff baked into it and also building that Craigstarter thing, that Kickstarter clone on Shopify. It's like how I build this system that once it's running, I can step away from and focus on what I want to focus on, which is storytelling, the book creation which, to me, is everything. Putting out those archetypes, working on the stories, inspiring people through that work, to me, is the whole reason to build this other system behind it and enable even more of that to happen on my own terms without having to go through traditional publishing channels which has its ups and downs. I’ve been making books now for 18 years and I think I can do a pretty good job at it. So, I feel I’m pretty confident about that. And if I can do it on my own terms, I just feel like there's a little more room to experiment and maybe a little more value in some ways through doing that. And it puts a stake in the ground for other folks who may be thinking about doing similar independent publishing work and allows them to kind of look at this and go “Okay, that allows us to be an archetype.” People can look at it and go “Oh, that's how you do that. Okay, let me try that now” because that's really what, we're just essentially mimics, we’re like chimpanzees, mimics essentially. And it's like unless you see someone doing something, it's hard to imagine yourself doing it. That's why I try to write these breakdowns, I try to explain how does membership program work, how does the newsletter system work, how do you use all these things to enable the kind of freedom and a sort of work that you're excited by. And I think, if more people can do that, then that's just a total net positive for the world. And so, just constantly trying to explain that, provide that archetype "This is how you do it. Copy me, please.”


Jayneil:  You're the perfect archetype for newsletter subscription and just growing one's business or passion through that. I read a lot of your blogs on how the whole newsletter stuff works, how to create a good one, the membership model. And I’m kind of curious when did you actually get the idea that “Hey, you know, I should have my own newsletter”? Now, obviously, it's at 17,000 plus subscribers but at one point it was zero. So, walk me through that journey from zero to where it's now.


Craig:  I started the first newsletter, wrote in 2011, maybe end of 2011, beginning of 2012. And that was because I wrote this essay called Subcompact Publishing that got picked up all over the place. And I wanted to capture that attention. And up until that point, the way I was capturing it was basically, if you’ve read an essay of mine, the takeaway was sort of “Follow me on twitter.” And I think I was just getting a little bit sick of Twitter and I think Tiny Letter might have popped up then, it was kind of getting some play and newsletters were just back on the radar. And so, I set up a newsletter and it just instantly had a couple thousand subscribers but I didn't take it seriously because at that point too, I was in this performative literary mode where I was like “Okay, I’m going to sort of renounce everything tech related. I’m going to go into these literary caves and I’m only going to write fiction” but that was an important sort of exploratory modality for me. And so, the early newsletters were like “This is going to be a newsletter but it's going to be really special.” Anyway, there was no schedule and they were weird and I didn't have enough rigor of process behind them. And it wasn't until the start of 2019 that I set up a schedule. And so, 18 months ago is when I said “All right, this is how it's going to go. Ridgeline is a weekly newsletter and Roden is monthly and I’m going to stick to that.” And my advice for anyone doing newsletters is two things. One is having a schedule because you're often not going to want to work, you feel like you don’t “feel inspired” but 99% of writing is just getting your butt in the chair, turning off distractions and just forcing yourself to write a few sentences. And then, more often than not, there's a lot more there. It's silly. And so, you have to just treat it like a job and have deadlines.


Another thing too is to think about it in terms of seasons. So, I think a lot of people can be overwhelmed if they say “All right, I’m going to start a newsletter. I’m going to do it weekly. And I’ve got to do this forever.” That's what freezes people. It's like “You got to do it forever? Oh my God!” And then you do like five of them and you're like “I can't do this forever.” So, think about it in terms of seasons and say “Look, season one of this newsletter is going to be for like two months and you just got to do it for two months. And then you can decide if you want to do season two or whatever.” And I find that that's like a technique for freeing up this kind of cognitive stress or worry about “Man, what have I committed to? Why did I have to commit to that much?”


Jayneil:  So, I would say that by the time in 2019 you became diligent about focusing on the newsletter, you already had a huge following on Twitter. Now it's insane too, 30,000 plus. I mean, assuming 2019, it was also quite high. So, that probably helped, I’m assuming, get a lot of people to sign up for the newsletter from your Tweets. What I want your advice on would be I’ve got, the podcast pretty much and then my next step is launching my own blog where I want to share some stories and kind of build an email newsletter. And I know it sounds very typical like “Okay, you build an email newsletter and then later, if you have a product, you can sell it.” So, what advice would you have for me in terms of starting off when I don't have a huge following like you for the blog, I would say.


Craig:  When I started writing blogs, it was less blog-ish and more kind of designed essays that I would spend a couple months on, some of these essays. And that was in 2009 I started really writing these chunky essays for the web where I’d think of them as both literally design-wise, photographically and kind of do almost like these big product announcements for these essays. And those did really well and that's kind of what started a lot any kind of following that I have right now. It was essays. In 2009, I had probably a thousand followers on Twitter or something like that. I started doing these big essays and committing to them and really spending like a month or two on one of these essays and then just really banging the drum when I put them out there. So, reaching out to people, putting it on people's radar that I respected. A piece of advice I give to folks often is if you want to connect with interesting people in the world, you have to bring something concrete to the table. So, one of the reasons I said yes to this podcast is because you didn't just email me, which a lot of people do and they're just like “Hey, I have this podcast. It’d be great” and it was like “Okay” but you produced something, you made something and so few people make things. And so, you put that on the table you said “Look, man, I made this video. I’m going to tell you exactly what we're going to talk about. I’m going to prove to you that I didn't just read half or one of your essays because I just want to fill up my roster of podcast people.” And so, you can do the same thing with your own work. So, when I would finish a big essay, I would look to everyone in that field that I respected and looked up to and I’d email them and not like a big crazy weird email but just be like “Hey, look, your work has been a big inspiration to me and that inspiration has kind of fueled my ability to produce this thing. I want to share that with you” and then not asking questions, not being like “Hey, man, can we do a Zoom” or “Skype” back then. “Let's get coffee.” None of that but just saying like “Hey, man, I respect your work. Your work has inspired me. This is what I’ve made.” And then, more often than not, if you've made something interesting, don't be a bullshitter, don't spend two hours on something and be like “Hey, man this really is like …” No. Really put the work in and more often than not people will respond to that because it's so rare for someone to bring something concrete to the table. So, I would work on these essays, put them out there and then just email everyone that I was inspired by and loved and they would write about it or Tweet it or whatever and that just kind of expanded the circle and then that increased the Twitter followers and blah, blah, blah, all that crap. And then, of course, when starting a newsletter, if you have a following on a certain social media platform, that's a great seed. I’m not very good at growing my newsletter. I’m not a super strong promoter of it. This is probably something I should return to maybe at the end of the year, thinking about ways to grow that audience but I really like the scale I’m at. I mean, this is another question, I think, that's really important for people to ask themselves is “What scale inspires you? What are you inspired by? What scale do you want to operate at?” At Flipboard, I worked hard on this product, we worked all-nighters, we’re going to launch this crazy thing and I’m working with the best people, the most talented, smartest kindest people I’ve ever met and we put this product out and instantly overnight, it's like millions of new users and like “Oh my God, 80 million users now on the platform.” And I realized one of the reasons I left was I was like “That does not inspire me. That scale is totally unimportant to me.” This is why working at Google or working at Facebook to me is just not interesting. It's like I don't care about that billion-user scale. I just don't. I like the intimacy of 10,000 and fewer. This is why a lot of the books I do are like a thousand copies, working up from there. I find that is the scale for me that allows me to tell a certain kind of human story. As soon as you start doing work for tens of millions or billions of people, there's a kind of dilution that has to happen implicitly because the scale is so big. And so, obviously, you lose intimacy but through losing that intimacy, you lose the ability to tell a certain kind of story. So, right now, my newsletters or whatever, I just feel pretty good. The membership program is going well and it's growing at a rate I’m happy with and it's enabling all sorts of really interesting work. So, right now, that scale, I don't feel like I have to do work to pump it up. So, what that just means is I can take that energy I would normally use for more pumped up promotion stuff, I don't know what that looks like, and I can just pour it into the books. Now, I’m starting to do some video stuff and thinking about that. And so, pour it into this creative work which is where I want the majority of my energy to go. I don't want to get sidetracked or distracted by these other kind of growth hacks or things like that. That's not interesting to me.


Jayneil:  That is so deep. You're essentially staying small on purpose. I mean, there's just something about you. I mean, I can go on a whole length about it. I’ve also attended Vipassana in Texas last year. So, I also feel, to everything you say, there's this deep thought out process. It takes balls, man, to just, I would say, walk away from being a partner or go away from private investing full-time even though there might be potential for more money but to focus on what you're doing and staying small on purpose because even I get delusion, I’m like “Oh my God, I got to launch this newsletter” and in terms of tech stack, I just got a ghost set up on DigitalOcean like that's what I’m doing to do the blog. Essentially, my thought is like “Okay, well, Craig has got this many followers” or “He's got this many subscriptions and this membership program. I got to do it too.” And then I’m like “Damn, dude, you haven't produced that value that's going to bring that people. I think, with you, you create these pieces whether it's your newly successful book that launched 100,000 dollars, Kissa By Kissa. I think what I’m learning from you is, and maybe I’m just walking myself through it, I maybe just need to focus on creating those essays, like you said, and writing those pieces and just create a blog, share that and if people like it, they will resonate and then come to it instead of me trying to growth hack this newsletter.


Craig:  Yeah. Well, I mean, people feel whether or not something is genuine. I think they intuitively understand that. Let me take a second to talk about walking away from stuff because I think that is an important point and it's easy to talk about. It's difficult to kind of understand the psychology there. So, a couple things. One, being able to walk away from stuff requires a certain amount of financial autonomy and a lack of debt. And so, my advice to basically late teens, early 20s or folks going to college is to focus on if they want to be an artist or a writer or work in a field that historically does not pay extreme amounts of money is you don't need to go to a 40,000-dollar-year university. Don't take that debt out just don't do it. I was lucky enough, when I was going to school, it wasn't that crazy expensive. I was able to get scholarships. My mom, for whatever insane reason, started saving for her unborn child's college when she was 20. I have no idea why she started doing this. So, my mom started socking money away when she was 20, adopted me when she was like 28. And so, she had put away enough money where I was really lucky not to have to take on debt. There was this kind of combination of things like working in the background, scholarships, and costs of school not being that crazy. So, that's really important to recognize, that kind of, not entitlement, but being in an extremely privileged position of not having a hundred thousand dollars debt sitting on your shoulders when you graduate. So, I intuitively recognized that and I did not want to take on anything that took away the freedom of no debt. So, that's why I like “How do I keep costs of living low? How do I live in super tiny places?” Just everything is for focusing on the creative work that I felt in my gut. I remember when I was 19, I had an internship that was paying really well, out in the Silicon Valley, at this company called Electronics For Imaging. They're like a printer company. They still make printer software. And they basically said to me at the end of summer “Hey, we'll cover the rest of school for you. Come work for us full time, yada, yada, yada.” And I just knew after having spent the summer there that it was not my destiny to work in a company. I respected the people I worked with, I found the work pretty interesting but I felt the pull, I knew there was other work I wanted to do and I knew that it did not happen inside of the walls of an office. And I just remember saying to them in the exit interview, this is when I was 19, “Thank you so much but I have to go do this other stuff” and then moved to Japan. And, actually, Japan was the further hack to keeping costs low because school in Japan was even cheaper than school in America. So, I was able to study out here at a fraction of the cost and get scholarships. So, again, 10 years later I’m at Flipboard and I’m leaving Flipboard after 15 months, which was crazy. I was one of the first people to quit the company. And at that point, it was like the rocketship was just going and every month I would just get an extra 10,000 dollars or something in the bank. It was weird. They just kept giving me bonuses without telling me. I was just like “What is going on?” And walking away from that was really weird and tough. Ed Williams wanted really badly to hire me at Medium when Medium had launched and I walked away. I’m not saying that to brag or to be “Hey, man, all these people wanted to hire me.” I’m saying that because I had real crazy opportunities that I said no to not because I was afraid of the opportunities but because I had such a strong pull to this other thing. Life is so short, so short. And I felt in my gut I had to do these other things. I just had to do them. I just came from the cave in India. I was just living in a cave in India, a metaphorical cave. I don't need to make 3,00,000 dollars a year. I don't need to buy fancy watches. I don't need Maseratis. I don't need any of this crap. I don't need to do private jet shit. None of that defines who I am at all, zero, zero, zero, zero, zero, zero. And the most expensive thing I ever bought in my life was a few years ago when I bought that Leica Q. I bought a car when I was living in California and then sold it on the way out but I bought that Q and it was 5000 or 6000 dollars and I had a panic attack when I was buying it because, to me, it was like so dissonant from my identity of who I was to own something that was luxurious or whatever. So, the ability to say no or step away from these opportunities required two things. One, building up this incredible habit of not defining myself based on material things, which I’d started in my early 20s and which really started when I was a kid because we had nothing material really in our house. I had no concept of brand name stuff. We'd go to K-Mart for back-to-school stuff. I just remember I’d wear the same shirt to school four days in a row because I only had two shirts. That is such a powerful habit that is almost impossible to build up in your 30s or 40s because you nerd yourself to a certain amount of material … And so, something I tell people constantly who are in college who are about to graduate, keep that recurring cost low. Do not go for the expensive apartment. Don't get addicted to buying a bunch of clothes. Don't buy the Beamer. Get addicted to savings. Buy a weird Suzuki. You can get these amazing Suzukis for 10,000 dollars. If you need a car, get a Suzuki, a Jimny. Jimny is so cool, man. It's like a mini G-Wagon for 1/20th the price. It's awesome. I love them. It's really fantastic. Build up that habit. If you want to do a certain kind of work, that's important. If you want to work at startups and just crank on companies, man, go for it. That's great. That was not my destiny. I did not feel that in my heart. In effect, that was part of going out to Silicon Valley was to stress that, to try that out. “What does it really feel like?” I thought that was part of my destiny and I think I could have continued down that path and it would have been financially extremely successful. That's for sure but I also knew that a lot of money wasn't going to change what I felt in my heart in terms of the work that I really want to be focusing on. So, being able to walk away from those things required that decades of habit building. And then on top of that, it required a clear sense of what I wanted to work on. You can't have this amorphous idea of like “Oh, man, I’m going to be like an artist” or “a writer.” I was like “I’m writing this book. I have this book to write. I’m going to keep writing this book. That is what I’m going to work on.” And so, you need to have both of those things, I think, to be able to say no to superficially incredible opportunities because what you're really saying yes to in these situations is a kind of spiritual opportunity which is much harder to quantify. It's so hard to quantify spiritual crap. It's like I was saying no to mega paycheck and working on big platforms or whatever but I was saying yes to a certain kind of exploratory freedom that, to me, defined in a lot of ways in terms of what I feel like I can do with life and with being alive. It defined for me the best way to respect being alive. That's how it felt to me. There was like this deep philosophical, almost spiritual component to it. It was like being alive is a special thing and it's important to recognize that so not just take that for granted. Life is extremely short. We're essentially dead, instantly. And at the end, when you look back on it, for me, there's just like three or four things that I still need to do that I’m working on that's important for me to get done. Anyway, it was a combination of all that – building up this habit of low material needs to self-identify with, building up this other habit of committing to creative work and understanding creative work, building up the habit of following this internal compass, and then being financially smart over the years and kind of understanding how to save and build up a cushion. All that's critical to being able to say no when someone comes to you with a big check or something.


Jayneil:  I think that was much needed to me. So, I quit my job at AT&T in June. And it was hard, man. I mean, I’m in Dallas, Texas. So, obviously, it's a little bit cheaper than San Francisco and I was making 120,000 a year. I’m 29.


Craig:  It's amazing.


Jayneil:  I’ve got a financial advisor like the guy who's doing the investing for me and stuff. So, that stuff, definitely, I feel, just like you, gave me a little bit of impetus like “Hey, you know what, if I want to do the podcast, if I want to explore that area, I can do it. And if worse comes to worse, in Jan or Feb or whatever next year, I can try to go back and just try to get a full-time job but I need to really go full throttle on this before I just say yes to other commitments.” You're a phenomenal writer. I guess, I wanted your advice on how to become a better writer. Is it books that I read or is it just drafts that I keep on practicing, get other people to review? How did you become a better writer or what was your journey like?


Craig:  Yeah, all of that. Well, I mean, writing has always been important to me. So, when I was a teenager, I actually started building a blog software when I was like 16, 17, 18, proto blogging software. So, this is a good example of being exposed to the right people at the right time. I just didn't have people around me that knew how to build businesses or work on things like that. Blogger was right there. I was essentially building Blogger because writing was so important to me and I wanted better platforms to write on the web because there really weren't any. And so, writing has always, always, always been exciting to me and being a novelist has always been something that was an appealing idea to me. In college, I was doing writing workshops and was reading a ton but I would say, just fundamentally, to be a better writer, you need to develop your ear. So, that's reading. So, you got to read the right people and you got to read them closely and you need to really try and understand what's happening in the work as you're reading it and try to mimic. Mimicry, as I was saying earlier, is a powerful way to understand how something happens. And then more than anything, it's doing a lot of writing, just tons of it and rewriting, tons of rewriting. It's just a skill. That's all it is. I mean, you can improve your ear to a degree but part of that is sort of implicit but you can definitely make your ear better so you can kind of hear clunkier prose or whatever just by reading more. You just read, read, read constantly. And I’m extremely strict about if I start a book and the voice is not a voice that I want to have part of my foundation as a writer, if I don't want to have this voice, if I’m not interested in it, if it doesn't hit me in the right way, I stop reading it immediately. I drop books really fast. And so, I tend to focus on and re-read a lot of the same books. So, people like Annie Dillard, for example. Annie Dillard, if you're looking to write interesting essays and you want to be inspired about form and you want to kind of think about “How far can I push an essay? What can it look like?”, pick up Annie Dillard Essay Collection. She is just operating at such a wonderful level and she provides such a strong archetype for “This is how you can do this in the world,” it's crazy. I just reread Denis Johnson's Train Dreams this morning. So, part of my schedule is that I try to not touch the internet until afternoon. I’m on a crazy schedule now, it's not great, I’m going to bed really late because I’m doing these calls late at night and all the COVID stuff has kind of made just a bunch of weird Zoom stuff happening in the middle of the night over here. So, I wake up and I’m not allowed to do any internet crap, look at the phone, look at anything because I find instantly that pulls my brain out of this kind of quiet, it activates this kind of messiness in the brain, which I find is not in any way conducive to good writing. And so, if I don't feel like writing, which is almost every day, I don't feel like writing, it's like you talk to runners and most of them don't ever feel like running when they wake up in the morning, but if I don't feel like writing, the only thing I’m allowed to do is read. And so, I read and then often what happens is I’ll start reading and in about half an hour to reading, if I’m reading the right stuff, I’ll be so inspired by a sentence, it'll just kick something off in the brain, it's like kindling, it just starts chain reaction and then I have to go run and start writing. I’ve basically turned my iPad into a writing machine where I’ve blocked the internet on it, deleted everything on it that's distracting and it's just this kind of overpriced writing tablet essentially. I find that also to be useful. Even just the existence of a temptation on a device for me just pulls the brain out of this kind of contemplative writing space because what's happening when you're writing is you're problem solving a lot of times. The impulse, I think, a lot of us have when we encounter a problem or encounter a bit of friction in life anywhere is to reach for the internet, pick up the phone. So, when you're writing, because you're problem solving, you're going to inevitably hit a bunch of problems. And if you have anything nearby that lets you swerve or ignore the problem, game over. You're not going to solve it in an interesting way. So, the best way to solve a problem if you're really stuck is to go for a walk. There's something about the distraction of the internet is not allowing for background processes to happen. So, that background problem solving, it does not happen if you're looking at crap on the internet, if you're binging. At least for me, there's something chemical about it. I don't know if it's dopamine rush or what but it's almost like a casino just starts up in the head and I lose all ability to sort of exist gracefully. I lose grace in my being. Anyway, that's how I think about the schedules. And you need to build up that habit. And if you do that, if you read good writers and read Bird By Bird by Anne Lamott, great book. Yeah, read books. Read Steve King's On Writing. It's a great book too. Just fill your brain with good writing and set a schedule and force yourself to write more. Just treat it like a job. You'll get better.


Jayneil:  Wow! Man, this is so inspiring at the moment, oh my God. So, how do people get in touch with you? How do people follow you? How do people contact you?


Craig:  I mean, subscribing to the newsletters is probably the best thing. Subscribe to the newsletters. Join the membership program. Give me money.


Jayneil:  And how do they find the membership program?


Craig:  Support my pseudomonastic life. It's And it's called Special Projects. That's the name of the membership program. The newsletters are the best thing. The reason why I like newsletters is you own the newsletter. You own those email addresses in the sense of you can bring them with you if you need to switch email providers. The email space for the most part is fairly static. I’ve seen writers, for example, commit to Facebook and Facebook is this ever evolving, horrible, demon, organism monster thing. You never know what it's going to look like six months from now. So, you may be investing and committing to this platform in one form and then in six months, it's a different form and it's not a form that you work well with. So, I treat Twitter and Instagram as ephemeral and I assume they're going to be gone and I assume they're going to disappear. Again, it's this thing of investing. There's this recurring theme going on – “How do I future proof my ability to keep doing this work?” If I am completely dependent on say Instagram, there could be a day Instagram doesn't work anymore.


Jayneil:  True.


Craig:  Then I’m out of luck. And so, email and the newsletters, to me, feel the most durable of all the platforms and the most likely to be around in say 20 years. And so, that feels worth the investment.


Jayneil:  How much can one expect to make if at some point they were to reach maybe 17,000 subscribers or 20,000 subscribers?


Craig:  How much money you can make on the newsletter stuff is totally contingent on what you're writing about. It's all specific to the value you're providing. I mean, Ben Thompson was making millions almost immediately because that value of here is actionable inside high-quality analysis of tech stuff. Yeah, I’ll give you, what is it, 100 dollars a year or whatever it was, it was like fairly cheap, when he started it. I was like “I’ll pay you 100 dollars a year because I know that that is going to turn directly into thousands or tens of thousands or hundreds of thousands of dollars in profit for me because I’ll make investments based on what I’m reading here.” And so, I think like newsletters that are finance related and fun are probably the easiest to make money off of. Stuff like mine which is, I don't even know how to categorize what I do, I mean it's almost like performance in some ways. You're definitely not going to make as much money. So, don't live in San Francisco in a 5000-dollar-a-month apartment and do a newsletter about walking if that's your business plan. You will be sad very quickly. You will go broke extremely fast. Again, living in Japan, my cost of living is extremely controlled and also healthcare. This is something that I think independent American creators have to contend with which is just the stupidity of the health system there and the costs can be so high. And here in Japan, thankfully, we operate on a fairly rational socialist-esque healthcare system. So, that is non-trivial. Moving to a country that takes away that huge chunk of worry, if heaven forbid some kind of health crisis befalls you, that's an incredibly powerful, again, investment in yourself to enable a certain kind of freedom going forward and I think that's important. You can be overly obsessive about being defensive and building up defenses to protect freedoms. And so, you do have to take some risks and you have to say “Okay, I’m going to sell a little bit of this. I’m going to take some of the savings out and put it into this project.” I’m shocked by the number of grown ass humans I know that don't have a brokerage account. That's crazy. It's totally crazy. It's completely bonkers. To me, that mode of savings is so intrinsic because I was lucky enough to do that stock investing club in high school that I can't imagine that not being part of the portfolio of things I’m doing to enable work going forward but you can overdo it too. Definitely emails. Email is a good platform to invest in.


Jayneil:  Thank you so much, Craig, for coming on the show, man. It's been a blast. I had such a blessed learning from you. I got the final much needed motivation to walk away from superficial things, things that are good on paper but thanks so much, man.


Craig:  Yeah. I mean, nice things are important when they're tools, I think. Everything that I spend money on, for the most part, is a tool. And investing in good tools is a great investment often because you can sell them for almost what you bought them for if it turns out that you are not going to use that tool like this mic is an expensive mic, it's plugged into this expensive USB interface and blah, blah, blah but these are all tools that I’m trying and committing to. That's also the interesting thing. Sometimes, there's this fallacy. You can spend money on a tool and then not use it. You don't buy the Leica if you think it's going to make you a great photographer but if you're already committed to photography and then buying the Leica, if that’s sort of a weird kick to further push you to do even more work but you already have to have that habit built up of doing a lot of work, then go for it. And think about it from a business perspective. Think about it “Okay. Well, if I buy this camera and I have this following and I start selling prints, then how much can I make on the prints and da, da, da?” So, for example, with the Kissa By Kissa book, I sold prints along with it. I did an addition of, I think, 30 and I sold the prints for 200 bucks. So, that's 6000 dollars right there. And we sold all the prints. So, that's 6000 dollars. Directly I can draw a line between that 6000 dollars and my photographic tools and you go “Okay, that's interesting.” And so, I was thinking about investing in a printer because I was like “I’d like to do more of these things” but this time I worked with a printer in Tokyo. And so, the upfront cost was bigger but it's like “Now that I know there is this interest, that gives me the permission to now go and invest, spend the money in a high-quality tool because I can see the sustainability around it.” It's not just buying the tool to fetishize the tool. It's buying it with a specific purpose and you buy the good one because you're going to continue to use it. And the good one, often in the end, it’s cheaper in some ways because it's more durable, it lasts longer and things like that but generally, the important thing is recurring costs. That's the real material thing. Auto loans, mortgages, rents, eating out at super fancy restaurants too much, buying super fancy groceries too often, those are the things that over time basically are the difference between massive, massive spiritual freedoms in terms of exploring the world and feeling like you have the ability to explore because you're not trying to constantly bring it enough to cover that fixed cost. So, it's the difference between that and going “Okay, I got to hustle another consulting gig because I’ve got to hit these costs” like in my 20s, essentially, I could do a month of consulting and that would cover a year of living. That was the ratio. That's a good ratio.


Jayneil:  It's an insane ratio.


Craig:  And that was just because I was choosing to live in Tokyo and I was making choices about the places I lived in. And Frank Chimero, the designer, one of his essays is about he had this like chart that he would put up on the wall and it would be like “Days of work to freedom” and he'd map out how many more freelance days he had to do until he could be done for the year and work on his own project. It's important to understand where those lines are and you can control those lines by controlling fixed costs.


Jayneil:  Absolutely. Thank you so much.


Craig:  Thus ends my TED Talk on fixed costs. Keep your fixed costs low.


Jayneil:  Oh my God, I feel like you should just have another career in financial advisor for designers.


Craig:  Sure.


You can find show notes for this episode and all the others at If you find this episode valuable, share it on social media and please leave a review.


Thank you so much for listening. Until next time.