Photo by Erika Dufour Photography

“I WOKE UP ONE MORNING AND I HAD THIS LUMP IN MY LIP. I’m sort of a hypochondriac so I was convinced I was dying. I searched the web and everything said, ‘Oh, you have oral cancer and you’re going to die.’ It kept getting bigger so I went to the doctor and was told that it was just a mucous retention cyst, which is when the salivary gland gets clogged, turns into a cyst, gets bigger and you have to get it removed. He took it out with a little oral surgery, piece of cake.”

“When I searched the Internet, everything still pointed to oral cancer.’ Then I wrote a post on my blog about if you got a lump in your mouth it might be a mucocele. Everything that was describing mucocele on the web was using words that nobody would ever use to search for those symptoms. That blog post became very popular and still is: it gets about 30,000 hits a month. I had 200 and some comments so I made a forum called I got all this traffic. I’d look at my analytics and thought, ‘God, wow, where is all this traffic coming from?’ I’d try to figure out how to make it better. I wanted to build a community and get people to work and interact with the forum in a better way.”

“At that time I was living in San Francisco. I remember I was at some bar hanging with friends on a Saturday night. Then Kevin Rose, the founder of who sold it for millions, walked in with his posse. I thought to myself: I want to go home and work on that forum. I need to work on my stuff. Why am I hanging out at this bar killing time when I could be finding my happiness?”

FINDING HIS HAPPINESS is how David Kadavy has created his entrepreneurial path. It probably stems from his curiosity for the world around him, which can border on obsession at times, like when it has to do with a lump in the mouth. He used that love of exploration when he authored his seminal book, Design For Hackers, in which he explained principles of design for the coder set. When it launched in the fall of 2011, it immediately ranked at #18 on Amazon’s Best Seller List.

It was evident that others had a thirst for what he knew about design, lumps in the mouth, and whatever else David was eager to explore and share.

That curiosity ride started when he was a child. As David puts it, ‘‘My mom told me I was always good at entertaining myself. I’ve always been curious and always enjoyed that ride of where my curiosity took me.” And that curiosity has sometimes been different than those around him, especially growing up in Omaha Nebraska where the mindset was more about going to school, getting married, buying a house and staying with the same job for an entire career.  As David put it, “In Omaha it’s all about the job. That’s everything.”

“I grew up in suburban Omaha surrounded by K-Marts, McDonald’s and gas stations. Our version of an adventure when I was a kid was riding our bikes across dangerous intersections to go to the strip mall and buy a soda. I didn’t know any different, but it didn’t seem right.”

“Then for college I went to Iowa State for graphic design. I also did a semester in Rome studying typography. I graduated in 2002 and got my first job starting the graphics department at an architecture firm in Omaha. Initially they just wanted to show clients graphic work of what a building was going to look like, but I ended up working on all sorts of projects. It was ridiculously stressful, crazy hours and for one reason or another we never hired anyone else, not even an intern. I was doing the one-man show, nobody was really managing my time, and I could be interrupted at any moment and asked to scan somebody’s picture of their grandson or fix a printer jam. I was expected to do things like that while I was coding or dealing with clients, and I didn’t get much guidance on how to scale things. I felt a sense of obligation to do a really good job but it stressed me out to the point where my hand seized up. I mouse with my left hand now because my hand got repetitive stress injury.”

“I also just didn’t understand the motivations of anybody around me. They had different priorities. They would ask me when I going to get married and buy a house. I heard over and over again about how buying a house was the best investment one could make. It didn’t make sense to me. I was 23 years old and I just saw the idea of buying a house as something that would limit my mobility.”

“At that time I was also very active in the graphic design and architecture community, the AIA. We had organized a tour of architects’ homes and I designed the brochure using great letterpress printing and great paper. It was my first big print job and I won a massive award for it from Communication Arts Magazine. Being in Communication Arts was supposed to be the greatest thing you could ever accomplish in the design world. That’s what you’d strive for in your career and it happened for me very early. But I didn’t find it nearly as gratifying as I thought I would. That caused me to re-evaluate things.”

WHILE DAVID WAS BUSY RE-EVAULATING THINGS, HE WAS ALSO SAVING EVERY PENNY HE MADE.  He would eat dollar meals for lunch every day and shovel the rest of his money into a stock portfolio so he could someday not worry about risk, having a job, or how he was going to afford to leave Omaha.

“I bought Apple and Google. They seemed like such no-brainers. I remember reading about analysts questioning whether Apple could continue to innovate. I didn’t think these critics understood how creativity worked. If somebody knows how to make something innovative, they know the process and they can do it over and over again. It just means combining certain factors together. With Google, the analysts thought it needed to go beyond search. I don’t think they understood the business model very well. To me, it was like the Internet was information and this was going to be the portals of all the Internet information in the world. It seemed pretty obvious to me.”

“So I worked at the architecture firm for about three years, working late hours and saving every penny. Then around 2005 I met this entrepreneur from California who was running a locally targeted test market for a job search website”

“So this guy would come to Omaha often and we started working together because he needed a lot of design work done. Then he would disappear for months at a time and all of a sudden show up again. He kept talking about how he was trying to raise his VC money and wanted me to work for him. I didn’t really know what he was talking about at the time, so I thought he was crazy.”

“Eventually he raised venture capital, $1.7 million or something. He was a typical Silicon Valley entrepreneur: sort of scatter-brained and erratic, but fun. We’d do some work and then we’d go out for drinks when he was in town. He was really proactive and made you feel special. He talked about moving me out to California to be their designer. I thought that would never happen because he was from the Bay Area and there were already so many great designers out there. That wouldn’t make any sense. Why would they do that? But they did it, and I moved to San Jose in August 2006.”

“When I told everyone in Omaha that I was moving to California, it seemed like people couldn’t be happy for me. Instead it was ‘The traffic is terrible there, the cost of living is really high, and you’re not going to get paid enough to live out there.’  All those things weren’t important to me. The important things to me were enjoying the work I did and working with people I liked and had a lot of respect for.”

DAVID WAS EXCITED, BUT THE NON-FLUSHING TOILET AND THE URINAL ON THE FLOOR where it had fallen from the wall, along with the old stained wood paneling on the walls of David’s “new” office in downtown San Jose made him think, “What did I get myself into?” But then he started working and felt like he was finally with people who understood him.

“They respected my opinions and ideas, they never said no to an idea and they wanted to work. There was a lot of energy. I was with them for a year. Again, I was the one-man graphics department designing and managing everything form the website to business cards for the sales team. I worked long hours. At first, it was just exciting and I loved it, but slowly I became unhappy living in suburban San Jose and with the way the company’s resources were being used. The Board included some of the most successful VCs and I thought that they must not have known what was going on because there was no way that this was the way they would run a company. We had grown from 15 to 90 people in less than a year, and there was no measurement going on how to best get sales, optimize the e-commerce flow for posting jobs, or measure how much money it cost to get somebody to post a job via e-commerce versus somebody calling from sales.”

“But the exciting thing was I was around all these entrepreneurial types. I was friends with people at startups like Meetro which was a bunch of guys working and living together trying to grow a company. It was exciting. I felt like I was surrounded by people who made sense. They weren’t worried about things that seemed really mundane. They were interested in following their curiosity and solving problems.”

“Then around 2007 after moving up to San Francisco, I found out about a design position at another start up, which was basically a Yelp for green and sustainable products and services. I was really searching for better meaning in my work, and working for the green sector seemed like it could satisfy that need. So I quit my job and started there. I remember when they hired me they told me they had previously gone through 11 designers. So I just tried to structure the conversation around business objectives like what was the company’s direction. They were thrilled with my work at first, but the problems within management were manifesting themselves in the branding and marketing of the company. If you don’t know what your company is, it’s hard to represent that.”

“They weren’t a technology-led company. The CEO had an entertainment background and was very talented at raising money, but didn’t have an understanding of how to grow this kind of company organically. Instead, it was like ‘Let’s throw money at this and see what happens.’ It was surreal. There were organic fruits at the office all the time. We would get massages and have company parties where they’d cater organic, farm-raised meat and vegetables. But it felt frivolous. I really wanted to feel like there was a sense of importance to the work. I think that’s when I realized that if it wasn’t mine, I wasn’t going to care about the work very much.”

“I was at that company for eight months until I got fired. I don’t know how I got fired. I didn’t really ask a lot of questions because there were battles going on in every direction. The company was trying to do so many different things at the same time. At that point I had enough money in my stock portfolio that I couldn’t find any reason to care about the job. I probably should have quit sooner but I still was that Nebraska boy who was afraid of not having a job. When they fired me I said to my boss, ‘Well, this will be a special day in my life, July 17, 2007.  This is the last day I work for somebody.’ People thought I was being dramatic, but I was serious.”

THIS IS WHEN DAVID STARTED THE PROCESS OF EXPLORING WHAT MOTIVATED HIM, and he found it to be tough. First, he had to get over the idea that he didn’t have a job, but cashing out 40% of his portfolio when the market was high helped quell that fear. Now he just had to figure out what to do with his time.

“I felt drained from working at my jobs – having to compromise my standards of quality and deal with the consequences of other people’s decisions when I felt I could make better ones. I wanted to do work that I thought was good and that I could be proud of, and wanted to recapture the feeling of being totally immersed in something, being in the zone and shutting out the world.”

“So I came up with this idea, ThroughAFriend, a Facebook app that was like a socially-intelligent craigslist. It used your social connections in Facebook by using a profile box. You could hit the support button on your friends’ listings all looking for, say, roommates. I spent months just on the specs because I couldn’t build it myself but I wanted to think through the whole product and really just make it awesome and get into all the details.”

“I made this PDF spec sheet to share with engineers to get quotes and stuff. I changed my schedule so that I could work until 4:00 a.m. and then sleep until the afternoon so there were no distractions. I worked on that for about a month-and-a-half, just doing graphics and thinking through everything. I hired a friend who was a fantastic engineer to design the back end while I designed the front end. We built this app, got it out there and it grew.”

“Then Facebook changed their API and removed the profile box and it just went straight down. I realized that it wasn’t a good idea to build on top of somebody else’s platform. Also, I wasn’t equipped to fix it. I didn’t really have the resources. The drive to raise money and get a staff going wasn’t there. That’s just not the way I operate. But I felt very good about the work.”

“It was fun because I was starting to take on this identity of being an entrepreneur, even though many people still thought of me as a designer. But I knew I was becoming an entrepreneur, and that I was interested in exploring and solving problems.”

“Then I decided to move to Chicago. I realized I’d gotten everything I could out of San Francisco. It unlocked creativity and built confidence that I never would have found otherwise. But I also felt that things had gotten out of control there, like there was a bubble going on. I was tired of constantly meeting that type of entrepreneur who was able to raise a bunch of money over a half-baked idea. I just couldn’t look into their eyes and see the motivation – to understand why they were doing what they were doing. Was it because they just wanted the prestige attached to raising the money? I felt there was all this noise, even though there was also a ton of opportunity. I also missed being around people who did regular things. I missed brick buildings, trees and seasons. I didn’t feel like I could just bear down and work on a project like I did when I lived in Omaha when it was snowing; that’s how I learned how to program, that’s why I worked on my blog. When there’s 12 inches of snow falling and you’re not going anywhere, what else are you going to do?”

“So I sold everything, packed a suitcase and moved. I got a place in the Ukrainian Village and shared office space with a couple of my friends who were running creative companies, which was great because I learned so much from them about that. Thanks to my connections from The Valley, I was able to land some big clients, and I started experimenting with projects. I was also writing a lot and realized how much I liked it. I found the Hacker News audience and figured out what sort of things they liked to read about and how to make blog posts that were useful and got traffic.

Then I remembered that I had done this presentation called Design for the Coder’s Mind where I did reverse-engineered visual design. I talked about design, color and geometry of grids in designing layouts. My goal was to present it at South By Southwest. So I came up with this idea about how to create something appealing.”

DAVID WASN’T FAMOUS, BUT HE KNEW HOW TO DRIVE TRAFFIC. To speak at the conference he had to get votes from a panel, so he figured he’d write a really great blog post to get the attention he needed. He wrote about the typeface Garamond and how it was designed so long ago as a lead type for print, which meant it didn’t translate well on screen with pixels. Since pixels are the unit used, that defines what makes good typography onscreen.

“I spent a couple of weeks working on it then posted it on my blog in July 2010. It was called Why You Don’t Use Garamond on the Web. It was an instant hit. It had 20,000 views within a couple of days. Then I got an email from John Wiley & Sons telling me how much they loved this idea of reverse-engineering beauty and offered me a book deal. It all happened so fast. I didn’t get a SXSW panel that year, but I did get a ‘book reading’.”

“It took me about six months to write the book. I was in my apartment by myself during a terrible Chicago winter. I had hardly any social life because I worked so much. But I didn’t consider myself disciplined, just paranoid. Just motivated. I joke that I don’t think I am a perfectionist because if I were, I’d do even better. Sometimes you just have to get it done, and sometimes those things turn out really good.  I think a lot of creative work is impulse and things that you don’t understand yourself. Like Steve Jobs says, ‘You can’t connect the dots moving forward.’ ”

“I had so much to say. I discovered that sometimes the things that are the most powerful to explain are the things that are so obvious to you but you don’t realize that the information you know might be helpful to others since not everyone else knows those things. I felt like I had been waiting a long time for this to happen, so I was going to seize this opportunity after spinning my entrepreneurial wheels long enough. I was worried about doing a good job. I had to organize all this content and it was a lot of work. I had a lot of anxiety about writing this book and meeting the deadlines.”

“Then I did an entrepreneurial retreat in Costa Rica with some friends, Noah Kagan of AppSumo told me to put everything on a calendar and break it down into steps. Once I spent some time doing that, everything was okay. That’s when I started to get into a rhythm. There were moments that really sucked, but then I caught myself one late night sitting in my apartment with books strewn about and the whiteboard on the floor, and it felt very natural, like, this is what I should be doing right now. It was natural but it was also painful. Pain is always a part of the creative process for me, just freaking out about stuff and then finally reaching a moment of clarity about what I’m doing. I’ve gotten better at managing that creative process after doing it time and time again.”

“The book is doing really well. I don’t know what that means yet. I’m discovering that there’s an audience with a hunger for this sort of stuff. It’s all part of my entrepreneurial process: finding what makes my heart beat fast and tickles my brain, yet other people also want. I love entrepreneurship and start-ups. If I ever have enough money I would love to be an angel investor. That would be so cool to make ideas happen and enable other people to navigate the entrepreneurial process because I think that self-actualization in our society is being a successful entrepreneur; that turning your passions, interests and relationships into a sustainable living is the definition of happiness in our society.”