back issue: why “must” I win? an origin story

This was originally posted to Medium by myself on Jul 18th, 2013.

Why “must” I win?

How I became obsessed with winning, learned the value of hard work, got into the web, escaped Yammer with a product development splinter cell, and other stuff no one cares about.

I imagine that change is more gradual than we give it credit for. Still, like most people I know, I have moments in life that I credit for making me who I am.

It doesn’t take a lot of dot-connecting to figure out how I became a web developer and user experience designer when you consider that:

• I have a mom who loves art, always encouraged me to draw my own comics, create my own magazines, and embrace my creativity. She always believed in me more than anyone else could. I went on to take every art class I could and soaked up all the computer art software I could get my hands on.

• I have a dad who was a UNIX geek in the 80's and 90's. He helped me make my first computer game when I was in third grade, grounded me when I created a BBS on our home PC, taught me how to set up a LAN party, bought me all the parts for my first computer — and helped me put them together, and he’s the guy who showed me how to reverse engineer HTML in 1994.

How I became someone obsessed with “winning” takes a little more work. I was always into sports and my family is religious about baseball. When I went to my first Cardinals game in St. Louis it was 1982. The game went 12 innings and was won when the Cardinals’ catcher stole home with two outs! That year they went on to win the World Series.

Picture and ticket stubs from my first baseball game at Busch Stadium.

The next year my dad was a little league coach and his team won their league. He coached the All-Star team a couple rounds further, I was the bat boy. I remember they won one game because my dad put on a trick play. The batter put the bat out to bunt and then drew the bat back and slashed at the ball, hitting it over the charging first baseman’s head to plate the winning run.

Lesson:
Winning is pretty cool, and sometimes you can win by being more clever than the other guys.

When my parents got divorced I was forced to realize that things weren’t always so simple. It didn’t always matter how hard you tried, you can’t always get what you want. Sports became more of a refuge to me in this time. The simplicity of playing sports was comforting. At the end of the day you either won or lost. You knew where you stood.

In junior high I was recruited to the Cross Country team because I kept posting the best mile time in PE every week. It was a place where I was in control. I found the harder I worked, the more tips I picked up by reading every issue of runners world I could find, and the more pain I endured - the better I did.

My junior year in High School I found myself at the All-State Military track meet. I had already won the 400, 800, and mile. The coach had agreed to let me take the 2 mile off if I won the first three, but we needed the points. So, I walked up to the line for the 2 mile a little late. As I did the entire starting line audibly groaned. The race was over and it hadn’t yet started.

On the ride home I told my coach I wanted to medal at the 3A State meet my senior year. He just laughed. Our school’s regimented schedule only allowed an hour for practice (including showers!) I was ready for a bigger challenge, but I wasn’t going to get it in Missouri next year.

I’m the skinny asshole on the left with glasses… I lived on bacon cheeseburgers and dipped my fries in mayo (thanks Pulp Fiction) and weighed 120 lbs.

Back home, I ran with my friend’s team at their informal summer practices. It became obvious that they just needed someone like me to slide in as their second place runner and we could have a shot at the 5A state title. I talked my dad out of spending a ton of money on another year of military school and proceeded to train my ass off until I weighed 130 pounds.

I medaled at the Arizona State 5A Cross Country Championships my senior year (10th overall.) Our team tied for the state title, the only time that’s ever happened. Their 6th runner beat ours and we lost...

Lesson:
Just because you put yourself in the position to win, it doesn’t mean you will. If you don’t put yourself in the position to win, you definitely won’t.

After my dad introduced me to the web in 1994 I became totally obsessed with making web sites. I did it because I loved it, not because I thought there was a career in it. Luckily for me it became a career around me.

In 1996 I graduated high school. A little after that I got a job offer to be a full-time web geek for a financial planning firm in Phoenix. As they say, “If you can afford college you no longer need it.” So, I took off and never turned back.

The amazing thing about it was — and still is — that everything you wanted to learn could be found, right there on the internet itself. Want to set up a web server? There’s a guy who posted something about doing that on your hardware with the software you have. Read it, follow along. Hack. Make it work! Keep trying… Win!

So, I had found another place where I would be rewarded the more I put into it, and dove headlong into it. I geeked out on it hard, had loads of fun with it, and gained sixty pounds.

I wrote a sales training video application in Shockwave (Director) that brought up reference materials at key points for users to study further or ignore to continue the video. We were prepared to launch it as a streaming web service when the dot com bust reared its head.

Lesson:
Being in the right place at the right time is better than the alternative.

When I think back on my second life, the one as a start-up geek in San Francisco during the “Web 2.0" era, I think a lot about the people I’ve worked with.

The launch photo from TopFans.com (which was the first spin-off product by the Zivity team.)

I think about the team at Zivity who let me get my foot in the door and gave me an environment where I could flourish. I think about going rogue with Dustin Curtis redesigning and developing the entire front end in one weekend. And, I think about our boss, John Manoogian, helping us prepare it to go live the next Monday morning rather than opposing the un-planned upgrade on principal. It was better so we were going to ship it!

I’m very fond of the time I spent working with Kevin Hunt and Vanessa Naylon as a 3-man product conceptualization and development team at Zivity. It was that group where we stumbled upon what I think is the ideal rapid product development structure (one Yammer is beginning to toy with now as well.) But, I also think a lot about Zivity’s struggle to survive, the friends who didn’t flourish the way I did, and the companies like Wikia where I contracted (and nearly took a full-time job) after Zivity.

Kevin brought me to Yammer when they were in their early growth phase a little later on. At that time there were still days where I’d find myself talking through and implementing last minute product decisions with David Sacks and Ilya Yakubovich. I put in a lot of sweat at Yammer, I made lifelong friends there,and Adam Pisoni almost killed me with a bicycle.

However, in 2012, I found myself feeling a lot like I was lining up on a track in Missouri again... I was ready for a bigger challenge.

Since then we’ve helped large companies augment their expertise, developed demo apps for enterprise clients, designed and developed pre-funding mobile apps for clients who went on to raise boatloads of money, helped ship time-sensitive features for start-ups, and created some great MVPs. We’re even getting close to releasing the MVP of our first internal application!

In short, we’ve been getting lots of wins, learning from our losses, and loving every second of navigating the chaos around us!