David Kadavy is a creative entrepreneur, author, podcaster, speaker, and creative productivity expert. David believes that one of the biggest challenges we face in the age of AI is the ability for humans to tap into their innate creativity.
Book: The Heart To Start: Stop Procrastinating & Start Creating
Book: Design for Hackers: Reverse Engineering Beauty
Episode Transcript (Click to expand)
Ramesh: Hello everyone. Welcome to the agile entrepreneur podcast. This podcast is for people who are interested in starting a business with purpose, passion, perseverance, and possibilities. And this is your host, Ramesh Dontha. Today I'm very excited to introduce a guest who I came across while I was writing and reading in medium. And then later on was referenced by many people about his work. His name is David Kadavy. So David is a creative entrepreneur, is a podcast host himself and a very accomplished writer and a bestselling author. And then we'll go more about his work you know, very soon. So David, welcome.
David: Thank you so much for having me Ramesh it's great to be here.
Ramesh: So David, I know I introduced you and I probably short changed many things, but why don't you tell us what you do.
David: Yeah, well, I guess primarily I'm a writer and podcaster. I made the decision about four years ago to really double down on that. I was already had written a book and I just wanted to take the time to follow my curiosity and read what interested me, talk to the people who interested me and to share what I learned along the way. And so that's what I do in the form of books and a podcast and some courses and occasionally speaking as well.
Ramesh: So one thing David that I was struck by introduction on your blog, right, so you start off with I'm a creative entrepreneur, so that's what I really wanted to dig into a little bit. What creative entrepreneurship things have you been doing?
David: Yeah, so it's an interesting term, creative entrepreneur because, I guess when I first started on my own, my main mission was just to follow what I was curious about. And that was 12 years ago or so. And along the way I didn't really think of it like as a business so much, as much as I thought of it as an artistic journey of let's find what's interesting to me, let's create things and let's figure out some way along the way to make some money. And you know, I eventually learned that people who are the traditional entrepreneurs think a little bit more structured about running a business is that there's a product, here's some customers, here's the market that's addressable and here's your marketing. And there's a system to all of that. And in a way you're not that concerned with your own creative expression or your own personality. It is what does the market want and how can I get that and how can I make money doing it? And so it's a complex balance to be struck there because I’ve also learned that, while you can follow what you're curious about and create whatever comes to you, whatever intuitively you want to create, you, you still do need to think about products and customers and resources that you have and processes for creating the product. And you know, what are the costs of that and how can you make that sustainable. You know, I liked the Walt Disney quote. We don't make movies to make money. We make money to make movies and I’ve come to think of my work that way. I don't write to make money. I make money so I can write. And so that's what being a creative entrepreneur means to me.
Ramesh: Yeah. Because the reason it struck me is that when I came across your writing on medium, I never thought you were an entrepreneur, right. I thought you were a writer, an author. Right. And then as we are getting prepared for the podcast, I was reading more of your stuff and then I came across this creative entrepreneur. I said, okay. And then because one of the challenges that people have is that they want to start something with a passion. So nothing wrong with it. But the challenge with starting something with passion and really doing something with passion is that they lose the perspective of profitability, making money and in the process, the passion you know, it goes away. So I think you are able to combine your passion to what you're doing, but at the same time keeping the money aspect in mind.
David: This is a difficult balance to strike is that well, if I was going to just be a writer and I would need to, I would need to have somebody else taking care of all the business stuff, you know, making it so that I could make the money to write. And so that would involve, I'm working with publishers, which I have done, but I tend to not to do now. I prefer to self-publish. And so you have to become a business person in order to make that work unless you're going to have an agent who takes care of all that stuff. Fortunately I'm curious enough and have a wide variety of enough of interests that I'm interested in doing that. And I enjoy all aspects of not only creating the work, but also trying to create a business around it. And it's a tough balance to strike because sometimes I find myself getting too caught up in the business parts of it is what do I feel like I should be doing. And then my work suffers from it. So you have to constantly be juggling that mind of thinking about the market and the marketability of your work with connecting with what it is that you're really interested in and what is really important to you and what you actually believe, not just what it appears that the market wants at this moment in time.
Ramesh: Excellent. I can relate to so many aspects that you're referencing here. Anyway, so let's now start tracing your journey here. So, David, I know you are a product designer in your past life. So if you could tell us, when did you make the switch from working for somebody to deciding to work for yourself?
David: Well, it was a July 17th, 2007. I was a product designer in Silicon Valley and my boss came to my desk and asked me if I could join her in the conference room and we walked down the hall and I was wondering what's in that yellow Manila envelope. And she sat me down and said, I need to terminate your employment today. And I didn't really, I didn't, I didn't fight it. I didn't really ask a lot of questions. I just got up and smiled at her and said, oh well thank you. This is going to be a special day in my life, July 17, 2007. This is the day I start working for myself. And it was funny cause I instantly knew that, and the problem was that I had not, my heart had not been in my work for a while. And I probably should have quit but then I got fired and that very instant, I knew that I was going to be working for myself.
Ramesh: Okay. So this is excellent. So then afterwards, excellent in the sense of the news was not excellent. What does excellent that you got to start.
David: It was excellent news actually turned out to be.
Ramesh: So then from that day onwards, did you have in your mind what you wanted to do, or did you take some time to figure out what you wanted to do? If you could talk about the initial few months or years, whatever that was.
David: Yeah. I had no idea. All I knew was that there had been some point in time where I loved something about what I had turned into my job. And that at some point in the previous three years or perhaps, during that previous three years, slowly I had lost touch with that, and I didn't love it any more. And so the first thing I wanted to do was just reconnect with that feeling. And I just felt completely debilitated and burned out to the point that I just, I couldn't fathom doing anything for anybody else, whether that was even freelance work. And I was in Silicon Valley with coding skills and design skills in 2008. So I had an enormous amount of opportunity right in front of me. And I just didn't, wasn't interested in any of it. Now I had built up a bit of a retirement portfolio of stocks and such.
And fortunately the timing was right. I had gotten some Google and Apple and had made a good profit on those stocks. And so I thought to myself, well, my roommate's going to business school for his MBA. Maybe I should think about something like that. Yeah. The more that I looked at that path, the more I thought, well, that's not going to get me where I want to go. I don't want to you know, do marketing at Proctor and gamble or something that doesn't interest me. And so I thought to myself, well, what if I just, you know, business school costs hundreds of thousands of dollars, I think, I'm not sure. What if I just gave myself the space and the time to explore and to try to learn. And you know, I wouldn't have an MBA when I was done, but an MBA isn't going to get me what I want, right. But I would have something, I would have some semblance of a business and I would certainly have skills and knowledge and experience that it didn't have before. So I cashed out about $40,000, and I said to myself, all right, well this is my DIY MBA. I mean, it wasn't, I wasn't necessarily studying exactly what they study in a business school, but I said to myself, well, I just need some time to not think about think about money. And it was tough. That was a huge chunk of my retirement portfolio, which if I had held onto it, would probably be you know, it would have grown to this to this day, but I just saw it as well, I can't, I just wasn't happy. I just, what good is the money if I'm not happy. And so I thought maybe I could invest in that. And so that's what I did. So for a year I went to a cafe every day in San Francisco. Went from one cafe to the next and worked on various things and built a Facebook app and made mockups and little prototypes of hundreds of other things probably and wrote blog posts and simply just try to reconnect with curiosity the best that I could. And so about the end of that year I then realized, well, you know, I did kind of what I wanted to do in San Francisco. I've worked for startups. I met a lot of people, a lot of connections that still to this day serve me. But, you know, now it's time to disconnect. This is just noise. It's distracting. There's something in my brain that I have to share with the world. I don't know what it is. I need to find out what it is. And then I moved to Chicago now. Why would anybody move from San Francisco to Chicago? It's supposed to be the other way around. Yeah, exactly. And you know, I remember my roommate being like, are you all right? This doesn't, have you thought this through. And you know, I just, it's funny I missed winter. I didn't, I didn't miss the cold. I didn't miss the snow. I hate all that stuff. I didn't miss tracking a bunch of a sludge of salt and sand and melted snow on my carpet and having to scrub it out. What I missed was the feeling of having no choice, the feeling of it being snowing outside and it's 20 below zero and all you can do is stay in. And when you stay in, you're reading books, you're learning programming languages, you're working on projects. I missed that long expanse of feeling like I didn't have any choice. And I also felt like, you know, San Francisco or Silicon Valley, it's a big hype place. You know, people get really excited about certain trends and such, and most of the time it's not going to work out. And so I saw it as noise and I really wanted to disconnect from that and go inward and explore and find out what was there. And so roughly, oh gosh, almost exactly three years to the day after July 17, 2007, I think it was July 13th, 2010, I believe was the day that I came up with the idea that became my first book designed for hackers. And so it was just as long process of exploration that culminated, in that book.
Ramesh: So your first "entrepreneurial journey" as a book, I mean, of course the book is the foundation of many adventures. So that's good. And then you also said that you talked about....
David: I will add that there were a lot of things that I did that didn't work out on the, on the road to arriving at that book idea.
Ramesh: Right. Yeah. I mean that's a typical path. Anyway. So, but at what point did you feel comfortable in this new journey that you were you know, doing, is it 2010 when you launched the book? Or it took some more time for you to say, this is where I want to stay, and this is the path that I want to pursue.
David: By the time I was offered a book deal, it was clear that there was very little hesitation that I wanted to do that. And you know, it wasn't that I had set out to write a book. It was, I set out to do something. You know, and it was clear by that point that this was the thing that I had been searching for. Because, you know, after that first year of wandering around and when I moved to Chicago, I started trying to, I started freelancing cause I needed to, I needed the money. So I started freelancing, but I was very intentional about limiting the number of hours a week that I did freelance. And I tried to mix in a certain number of hours a week as well of trying to build passive revenue streams. Seeing that I would be buying myself time, at some point down the road where I could have more space to continue to explore. And so when I did get offered the book deal, I had set up everything in my life for an opportunity like this. I fortunately, the timing was great. One of my passive revenue streams started to grow just as I got that book deal which was totally necessary because the advanced wasn't going to be enough to pay my bills for six months or whatever it took to write the book. So it all, it all felt, it all felt comfortable that, this was something that I wanted to do, that I had been waiting for. And it was, it was more of a, it's about time feeling. Finally, I'm this person that I have known myself to be and finally the world is going to acknowledge it.
Ramesh: So David, it's a very fascinating, so what you have done to really go on this dream journey that you have. You first made sure that practicality, you know, in the sense in terms of multiple passive income streams, you know, whether it's a retirement stuff that you had that initial seed money afterwards that some other freelancing and few things that you're doing that sustained you. I think that is a key learning for everybody who wants to do it right. So making sure that those are there. Otherwise what happens is people, you know fall on the face and then they go away, right. I mean, at the same time you are investing all those into your passion of writing. So the third thing that I learned is your first book was not a self-published book. It's some, basically, so you're going to advance for, publisher paid you for this, is that right?
David: That's right, yeah. It was with John Wiley and sons, which is a huge publisher.
Ramesh: Okay. So David, if I could dig a little bit into that one. I myself you know, explored many areas, but I went to self-publish route. So if somebody is there, a combination of entrepreneur, author wants to be, so how did you snag this initial deal, book deal.
David: So what happened on July 13th, 2010 was that I came up with this idea of design for hackers. And the reason why I came up with this idea was because I was trying to get a, I was trying to get a slot to speak at South by Southwest. Which is a big tech conference. And it's, you know, prestigious, whatever to speak there, but they have a sort of democratic panel picking process where you need to get a bunch of votes to have any chance at having your panel chosen or your talk chosen. And so what I decided to do since I didn't have much of a platform at the time was to right the best darn blog post I possibly could about some element of designed for hackers. And to get that post to do very well on some portal. The portal being a hacker news at this point. I had a pretty good feel for what it took to get something to the top of it. It's, you know, it's one of those upvote sites like Reddit. And so I wrote this post why you don't use Gerome on the web. And in the post, I asked for votes for my South by Southwest talk. Well, yes, and so I wrote that posts, it went to the top of hacker news within a few days. I had an email in my inbox saying, Hey, I like this idea of a design for hackers. Have you thought about writing a book about this?
Ramesh: Fantastic. David, that is a very good story. Okay. So excellent. So now let me go segue a little bit into, so we talked about your book and then I’ll come to the heart to start book a later on. And then, but I want to go into the podcast. Love your work, right. And is the podcast being also a business venture or is it more a venture of your heart? What is this?
David: Oh, boy. I mean, is there a difference? And for me, sometimes it feels unfortunate that it feels like there isn't a difference. Is that a lot of difficulty doing stuff that isn't an endeavor of the heart? You know, it's a part of my business for sure. I spend money on it. I make some money on it. I'm a little bit more than break even on it. But it is more a personal exploration than probably anything else, which, I mean, I guess I see my entire business that way. In that I'm always reading books and it gives me an opportunity to connect with and meet the people who write these amazing books or heroes in other avenues. People like Seth Godin or Jason fried or Joanna Penn who is a big self-publishing guru and so many people. Steve case, the former CEO of AOL. Adam Conover who has a great television show, John Bokenkamp, who created the blacklist for NBC. I get to talk to all these people, and I get to test my theories with them, I guess, like, ask them questions and match them up with the things that I and learning and wondering about what it takes to make it as a creative entrepreneur. How do you navigate this space between all right? Commerce and art and so primarily that's what I get out of it. And then the byproducts are books and blog posts and some courses that I'm working on as well.
Ramesh: Okay, great. I mean, you really have some big names there, James Altucher, I see there as well, Savannah Edwards. So how did you get them as your guests? If I could ask.
David: Yeah. I don't really know. Sometimes I don't, Sometimes I don't really know. Certainly having, if I were to guess, I would say that it helps that I already had an audience from design for hackers. You know, when I started the podcast, my email list was somewhere around 30,000 people, something like that. But this was for design for hackers. These days I have, I’ve broken it up in a different email lists for different interests and I’ve also cut out a bunch of people who weren't, who weren't particularly responsive. But to be able to say, hey, I’ve got this podcast, I'm an author. I would love to promote your work to 30,000 email subscribers. I'd like to have an interview. It'd be over the internet. It'll be an hour long. That goes a long way. And in some cases, some of these guests, they were familiar with my work. They maybe weren't huge admirers necessarily, but they at least knew that I existed. You know, I was living in Chicago for eight years. Jason Freed is based in Chicago. Through the grapevine I'm sure he was familiar with my work. And you know, Seth Godin was somebody who I’ve probably first emailed Seth Godin in 2005, and you know, not that he knew that I existed, but there's that little sort of subconscious thing of, Oh, here's this name that showed up in my inbox. Do I recognize that name? So maybe of that as well. I think more than anything though is simply being a fan of the work and truly understanding the work, being able to, you know, being able to write that one sentence. I mean you don't have very much time when you're trying to connect with somebody that you don't know who has a lot of people asking for their time and they don't, they don't know who you are. Being able to write like one little sentence that tells them, I have read all of your work and I understand it and I want to promote the values that you promote. It's not saying that, and it is not, I'm quoting anything that they've said. It's demonstrating that you have truly internalized what about, and that you have genuinely something that you're curious about to talk to them about. I think that that helps. And then of course, after a while it becomes, you know, all these people have been, Dennery Ellie's been on my show, James Altucher has been on my show. Being able to have those names and names that they recognize that they would like to be in the company. I think that probably helps as well.
Ramesh: Yeah. The food is then it self actually that is very interesting. Yeah. So one thing that I wanted to ask you David before, and I'm going to ask you on this forum. I stopped while I was reading your biography at one point where biography in a sense or whatever you wrote on your blog about yourself is that you moved to Columbia. And then I said, wow. So what made David take this step? So if you could talk a little bit about you know, your move to Columbia and then why you decided to do it.
David: Sure. Well you know, it's the land of opportunity. No, you know people move from another country to another country often because they see some kind of opportunity there. Now, plenty of Colombians would love to move to the United States. I am not, that is not a surprise to me. The United States has a lot of wonderful opportunities in it and I have been privileged to be able to be a part of that and to still have the blue passport be able to come and go as I please. What I saw in terms of opportunity in Columbia was that I, as a writer or what I really wanted to double down on writing and podcasting and I really wanted to take the time to read about things and learn about things and share what I learned along the way. I felt like I was going to need some runway to do that. And I wanted to be in a place where there was going to be very little friction where I could really dig into thinking and writing and that there wouldn't be distractions. So it was a little bit like my move from San Francisco to Chicago, but a little bit more intense in that, you know, living in Chicago, I might get, I have a friend say, Oh, I'm having a cocktail party this weekend. Well, my friend lives in New York. And so I would fly to New York to go to a cocktail party or, I would get speaking invitations that didn't pay. And they were wonderful travel opportunities. And it was amazing for a few years there. I got to travel all over the world. I spoke in eight countries and Chicago was a great airport to fly out of places, you know. And so I wanted to kind of create a forcing function of, all right, well, you're in Columbia. If you're going to travel somewhere, it better be important. And on top of that, Medellín is the city of eternal spring. It is room temperature all the time. It's close to the equator. So the sun rises and sets at the same time. And so as I was trying to basically optimize ways of being creative, of having ideas, turning them into finished products and developing systems and habits and routines, that centered around that. Medellín was going to be an obvious place for that. I had already spent a couple months here several times and so I made the move. It was going to be cheaper. It was going to be less friction. I could still get books over Kindle, which at first, I thought was a disadvantage, but it turns out because I can aggregate my highlights using tools like, one that's called read wise. It turned out to actually be an advantage to managing my knowledge and processing the things that I'm learning and turning them into finished products. And so from all those standpoints, it was the land of opportunity for me because anything that would get in the way living in the United States, a lot of that stuff would be out of the way living here in Columbia.
Ramesh: That is true. So David as we come towards the end of the podcast, so you know, the thing that strikes me is that you are able to combine and you're not a typical entrepreneur, right. So it's going out doing affiliate marketing or whatever, whatever. Right.
David: I mean, I did plenty of affiliate marketing, but that was to, you know, make money so I could write more.
Ramesh: Yeah. Yeah. So you're not building on those things, right, but exactly. So essentially writing is the linchpin of all your efforts and then you're able to connect different dots into your writing and books and all this stuff to make money. The business out of it, let me put that out. So, and then, so everybody has a different path. And then going back on your path, anything that you think you could have done differently, or this is the path that you're destined to take in spite of, you know, different digressions that maybe.
David: I mean, it's always so hard to look at the past and even picture doing anything differently because I think we're naturally biased to not have regrets, right. To not think that we made the wrong choice in any way. So the only thing that, you know, if I could wave a magic wand and be a different person, I think I would well, you know, like you say, I'm probably not your typical entrepreneur. I do things my own way. But that has been, that's always a struggle to do that. And I look at some people who are even more so that way, who really don't care what anybody else thinks that they should do or thinks that they should be like or thinks what they should think or what they should say. And that's something that I'm constantly striving towards is okay, the decisions I'm making are those decisions, am I making those decisions because I’ve seen somebody else do it and I think that I should do it, whereas this would I truly feel is right for me. I just, I always have wished that I could, if I could change anything, it would be that I could be more that way more quickly and it's an ongoing process.
Ramesh: It did definitely then. So another person told me is that, you know, even the ups and downs, everything was, I know as a teaching experience. So all the steps are necessary to, for them to be where they are now kind of stuff, which is what I think. The last question David, as an aspiring entrepreneur, sitting at home, are there any things that you could tell them they should be thinking about or doing based on your experience and based on everything that you've learned from your podcast and your engagement with other business people?
David: I think that it's good to ask yourself, well, I think it's good to understand or accept it. There are no guarantees in this. And especially if you're going to be a creative entrepreneur, it's going to be very uncertain and volatile and there's going to be a lot of randomness involved in your success and luck involved in your success. And so if that's the path that you want to go down, you have to ask yourself if you're okay with failing at it, and what does that look like? And if you can go down the chain of events to where you're failing more and more and more and more, and you still say to yourself, okay, I'm still up for this, then go for it. Otherwise, I would say don't.
Ramesh: Okay. David, thank you very much. I'm a huge fan of your writing. But that's good to know that you're a writer who also makes money. It is practical. Because at heart, I'm a more a business person. And then writing is on top of it. And then you are on the other way around. So it's a good to meet you. Thank you very much. And thank you for your time, David.
David: Thank you so much for having me. It's been an honor.
34:42Ramesh: Yeah. Thank you.