When I was 5 years old, my school had a lab filled with old Apple computers. Every week, we would go in there to play games, both for learning and for fun. This was my favorite part about school, but I never got enough time in the lab.
I was 8 years old in 1994 when I received my first computer, a Vtech Power Pad. The learning experience itself was incredible, but I noticed something peculiar about the manual: two-thirds of it was about a programming language called BASIC. Soon I was writing programs to convince my friends I was able to hack into government computers from this kids laptop that wasn’t even connected to the internet. That was fun, but I needed more.
Let’s switch to a timeline for the rest of this:
- 1995 - I was at a garage sale with my grandparents when I came across a 386 machine complete with a monitor, keyboard, and 5.5-inch floppy drive. With this I learned DOS to browse the filesystem and run programs from the command line.
- 1996 - I bought a Packard Bell from my uncle. It ran Windows 95. I became a wizard at Microsoft Paint as well has hacking the registry to customize the Start menu.
- 1997 - Enter AOL 3.0. The internet was the most amazing thing ever. I met a lot of strange people in a lot of strange chat rooms. At some point I learned about progz, or programs you could download to create unfortunate experiences for others like flooding their inbox or kicking them offline. After impersonating an AOL administrator to prank one of my friends, I was banned from AOL for life. Over the next several years, I stayed online for free by hacking to extend free trials from service providers like Juno, Kmart BlueLight, and Netzero.
- 1998 - I began creating things like Real Player skins, Winamp skins, game mods (modifications), and VRML 3D products to share with the online community. Then I discovered something incredible: free personal websites. I created accounts on Angelfire, Geocities, Homestead … you name it, I probably built a website on it. I tried to memorize every HTML tag on Blooberry.com to get better at coding. I also coded my first Java applet to run a chat room on my personal site.
- 1999 - I made the switch from Microsoft Paint to a pirated copy of Photoshop 5.5. I learned Macromedia Dreamweaver and Flash including ActionScript. I created my first personal blog and began writing tutorials.
- 2001 - My youth group asked me to create a microsite and flash banner to promote an upcoming event. Our agreed upon compensation was a PlayStation 2 valued at $300. This sounds ridiculous now, but this taught me a very valuable lesson: I can make money making websites.
- 2002 – 2008 - Over these next several years, I worked various retail jobs with intermittent paid freelance design and development work. I was good at it, and it didn’t demand too much from me. I never quite hit it big, but the money was good. I decided to balance my steep coding knowledge with a graphic design degree.
- 2009 - I graduated from the Illinois Institute of Art with a Bachelor of Fine Arts in Graphic Design.
Oh, Art School
All of the people that surrounded me in college had a profound impact on where I am today. I met my wife Megan who was in the interior design program and she is still one of the best and most talented designers I know. All of my roommates have successfully launched careers using their degrees. John is lead motion designer at Google. Mike makes video games you’ve played. Kyle makes websites with bears. Joe made Halo 5.
Most notably, my closest friend in college who helped me every step of the way and has helped me ever since. We printed our projects at 4am at Kinkos together, created an impressive motion graphics video together, and learned how to be better creatives together. He even landed a coveted role at Chicago-based Basecamp, a place we both dreamed of working back in school. Mig Reyes is now a designer at Tock.
After school, I had trouble figuring out what I wanted to do. An unpaid internship seemed like a step backwards from the self-employed lifestyle I was used to. With no real direction, I ended up teaching graphic and web design at my old high school while freelancing for small, local clients. This worked for awhile, but I wasn’t advancing my career at the pace I had hoped. I needed something more consistent closer to the city.
While I was at Paper Tower, I learned something very important: the hourly rate we billed our clients was much higher than the rate I was paid. I knew this had to be the case, but since I knew very little about business, I was surprised by both the margin itself and the intricacies of managing and sustaining a digital agency. I needed to test the waters and see if I could figure it out.
Over the course of several months in the middle of 2011, I spent several thousand dollars trying to start my own agency in my spare time. Since my sister and a couple close friends weren’t doing anything else, I decided to break the cardinal rule of starting a business and hire them to help me. A lot of research, planning, pivoting (maybe we can be a social media management platform) and only a few clients later, it was done. I don’t regret this, though. It motivated me, made me more curious, validated my ambition, and gave me a newfound reverence for industry, networking, marketing, salesmanship and strong business acumen. I wanted these skills, but I needed a more intimate look at how others were already doing—and scaling—traditional business with emerging platforms and technologies.
The Mad Rush of 2012
In early 2012, I took on a WordPress project with a healthcare incubator called Healthbox. Over the course of 3 months, I occasionally observed as 10 ambitious startups worked hard to plan, pitch, and improve their ideas. I was invited to investor day where I sat next to Desiree Vargas Wrigley and heard the CTO of the United States speak about how our future depends on our ability to solve problems with technology. Both Healthbox and GiveForward made me full-time offers that I turned down, but the experience was a turning point for me… I needed to be in this startup world.
From April to June, I spent a lot of time in Chicago touring my friends’ workplaces, sitting in 20 on-site interviews, and attending dozens of networking events. I accepted an offer and was one of the first hires at a startup called Aggrego owned by Chicago Sun-Times, but that didn’t work out. At TechWeek Chicago, I met a guy named Pete Soung from Sprout Social, spent a lot of time drinking with the Guild Capital guys who ran TechWeek, and I bumped into Desiree again.
Knowing I was unemployed, Desiree graciously offered me a temporary position at GiveForward. Going to my desk at this scrappy, young startup in the city every day for the next month affirmed that this was the type of culture I had been looking for. I had a decision to make, though. Desiree offered me a full-time position, but so did Guild and Sprout. All the guys I met during my interview at Sprout talked about how much the company valued and supported learning and growing as much as possible. This won my decision, but leaving GiveForward and turning down the guys at Guild was not easy for me.