I apologize if that sounds like bragging, but I want to share a bit about my crazy journey from $8/hour to $100k/yr. I am far from a genius and I am not necessarily a “go-getter” who is “crushing it” everyday. I spent high school doing musical theater and spending time with friends, and spent college trying to figure out what I wanted to do in my career. I found myself barely making it through my second year of college with a ton of debt and no foreseeable career.
I must preface this with the fact that I had always been interested in technology and had some minor experience previous to this. I loved video games and had spent much of my middle school years trying to write code for my GameBoy Advance and Nintendo DS. I learned HTML through a community college class and began building websites for friends and family. I was able to make a bit of side money making websites during high school. I was always curious about learning more web technologies, but never really spent time researching or learning that much. I spent a lot of time messing around in Photoshop and Illustrator, but never got proficient. When I went to college, I got the MacBook Pro with the free iPod Touch deal. This was the first generation iPod touch and I immediately attempted to jailbreak it. Long story short, I began writing little bits of code for iOS and when the SDK came out, I dove in. I had a lot of free time at college and learned a lot about the iOS ecosystem. Got a few freelance jobs doing projects and had a ton of fun doing them and was able to make a decent wage.
My situation changed in Fall 2010 when my Dad lost his job. I had been able to pay for most of my school, but had to take on some serious student debt. I didn’t want to take on any more debt and my parents couldn’t help me out. I wasn’t very happy or excited at school and was pretty burnt out. I decided it was as good a time as any to do my own thing.
Unfortunately, I never planned out what “my own thing” was. I sat around at home during the holidays after the Fall semester passively looking for work. My parents pushed me to work with a theater company I had participated in during high school. I was moving set pieces and cleaning up a warehouse for little pay. It wasn’t something I wanted to do, but it made me feel productive and I didn’t want to be bumming at my parents house all day. My girlfriend was working at Jersey Mike’s at the time and my dad suggested I go work there. This got me pissed because I was SO done with food service after working at Jack in The Box for several months.
I combed Craigslist for tech jobs in the web design and web hosting space and a few iOS positions too. The next day I had 3 interviews all in the same day. I interviewed with a weird manufacturing company to be their web manager, got to the last 2 applicants, but wasn’t picked. I was offered positions at the two other jobs. I worked with IntoMotion briefly, helping do a little iOS work. This opportunity made me see the possibility of making a living being an iOS developer and got me pretty excited. Unfortunately IntoMotion wasn’t paying me very much and it was a long drive out there. Media Temple offered me a better paying job, closer to home, as a tech support agent. This was a great opportunity for me to learn the basics. I got to solidify my understanding of many topics like web hosting, FTP, SSH, Wordpress, and other important web technologies. The guys who worked there were pretty sharp and taught me a lot. I enjoyed the technical challenges and general atmosphere, but I hated getting yelled at on the phones. I eventually couldn’t handle customers and started looking for other work.
I was set on being an iOS developer. This was when I started to become a total fanboy about a few well known iOS developers. I started following many blogs and got very educated on the iOS space. I spammed my resume out again on some mobile positions and got a few responses. I ended up interviewing with PennyPop in a loud McDonald’s near my girlfriend’s house. They put me through a technical interview and ended up offering me a job. It wasn’t anything glamorous, but just the prospect of building software was too good for me to turn down. They told me I had the weekend to think it over and if I took the position, I would have to relocate to San Francisco within the month. I had long talks with my family and girlfriend and eventually decided to take the position. I would not be where I am if I stayed home.
Pennypop (it was called MIR Partners back then) was the ultimate startup experience. I drove up to San Francisco after buying an iMac to bring with me for work. I didn’t know where I would live or what I was doing, but I was excited. I got very lost in the city and couldn’t find a place to park, but eventually managed to get to the high rise apartment that the company was working out of. I made it up there, met with the team and was very out of sorts. I expected at least an office of some sort. We had an initial meeting in the bedroom of one of the founders. They told me they were going to put me up in a hostel. The night in the hostel was very unsettling and did not exactly inspire me to love this company. After a week of craziness, I got an apartment in Daly City, figured out the BART, and set up my iMac in their new office. I ended up working with some very smart individuals who expected a lot of me. I like to think I rose to the challenge and pushed hard to make Pennypop a success. I learned a ton by being required to solve tough problems on iOS and I have never felt so energized. This energy could only last so long of course. I eventually got a little bit burnt out, got a little angry/frustrated with the founders, and missed my girlfriend and family in LA a whole lot. We had a pretty complete product, but it wasn’t ever good enough for the founders to ship because the requirements kept changing. I wanted to see it launched, but I wanted to go home and work in a lower stress environment more. Pennypop recently launched and is doing very well on the App Store.
I was a little scarred by the realities of the video game market and the shady tactics games used to get you to buy in-app purchases. I wanted to work on software that wasn’t trying to trick people, but was providing them real value. I left Pennypop in January of 2012 for CityGrid Media in Hollywood and moved back in with my parents. My girlfriend and family were happy to have me back and I appreciated having my support structure back around me. CityGrid was a great experience because, even though we were still trying to trick people into looking at our ads, we were providing real value to small businesses and consumers searching for said businesses. I worked on the Citysearch iPhone app, and Cityseries iPad app. I also worked on trying to reboot InsiderPages as a mobile first property, but this never panned out. I worked with some smart and fun people at CityGrid and learned a lot about building local, mobile apps (see SOLOMO). My girlfriend was hired to work with me there as a graphic designer after we were part of the winning team at the CityGrid Hackathon in LA. I had a great time working on the sunset strip with some very talented developers and product people.
As of 2013, I am at TripAdvisor and get way too much recruiter spam. I never thought when I dropped out of school that I would be making an above average salary, building software, and have my pick of hundreds of companies to work at. It was not all roses and butterflies along the way though. In an effort to summarize my story, I left out my struggles with depression and staying healthy while working 24/7 and finding work/life balance. Luckily this story has a pretty happy ending as I am getting married to the love of my life in January 2014. I am not sure what is next, but I am extremely thankful for everyone and everything that has helped me get to where I am today. At least in software, you don’t need a degree to start a career. I got lucky having the right skills at the right time with iOS. I encourage you to find hot technologies to leverage to get inside big tech companies and learn from those around you. Stay tuned for the next chapter.