I've had a life plan thought out for a while now, and with 2010 only two days away, I thought I'd let everyone know about it. This is what I plan on doing over the next fifty years of my life — basically, until I retire. I like thinking about the big picture because it gives me a horizon to drive towards even if in all probability I'll fall a goal or two short.
Most startups have a short shelf life. I've been fortunate enough to be a part of two with atypical life spans. TypeFrag was founded by me in 2003, later sold in 2007, but it's still alive and kicking and doing well after over seven years. Carbonmade was started in December 2005 and is now four years old and counting. Realistically, however, only the last two years belong to Carbonmade because before that it was only a side project.
In venture capital circles, most successful businesses that receive funding have a seven to ten year life cycle before they either have to go public or be sold off. While I'm not anticipating Carbonmade going public, and while we haven't raised any capital, which might make these numbers seem irrelevant, I do foresee something major happening at some point over the course of the next seven years, which brings me to 32 years of age.
What will happen? Who knows? But I truly believe that we are capable of building a one hundred million dollar business in our market. We've got the talent, the user base, the growth and the game changing ideas to make that happen. So realistically I can see myself completing the Carbonmade chapter of my life by 2017, or at least having a reduced role at that point.
32-33: Chef School
I've always had an interest in cooking — and eating — since I was a little child. There's also obvious synergy between entrepreneurship, startups, and cooking. You'd be surprised to know how many of my colleagues appreciate the art of cooking and eating well. Maybe it's because cooking is part formulaic, part creative in the same proportions that the startup mentality requires.
Something I've always wanted to do is spend a year in France at cooking school. I've done a lot of traveling but can't say I've lived in another country long enough to really get the feel of the place. I didn't do junior year abroad or take a year off for travel after college. It's something that I feel is missing from my life. How can I be so sure that America is the country for me if I don't have the experience of living somewhere else?
33-40: Unknown Startup
While you could say I've "played it safe" with both TypeFrag and Carbonmade, I'd like to shake things up a bit and come up with a game changing technology startup like Jack Dorsey's Square. It wouldn't necessarily have to be a hardware startup, but something where I flip the script on how business is being done, or maybe something in consumer technology. I haven't thought long or hard about any anything definite yet, but I've involved myself with a network of highly intelligent and successful entrepreneurs in New York whom I would hope to work with on this startup. Let's hope at least a few of them are free around the same time and have similar ambitions.
On a more personal note, it seems likely that I'll get married and have kids during this time of my life. While you can't anticipate those things or really plan them out, I anticipate that this'll be the time for me. Can't wait to take the little one into the office and teach him/her about startups. :)
40-50: Apple's CEO
Being the CEO of Apple is my oldest and wildest dream. Since I started using computers I've always been an Apple user, and then my love of technology, entrepreneurship, management, and developing cool products has made me a huge fan of Steve Jobs and everything he's accomplished.
I hope that having three startups under my belt — especially my "Unknown Startup" that will change the game — will put me on radar for running a large company. Why would I want to run a large company, you may ask? Well, I'm one of those people who like to put a check next to life's accomplishments and don't like to repeat things more than twice. I'll have done the small <1,000 employee startup and I'll be hungry for more. You've got to set goals and push yourself to realize all that you can achieve.
50-Retirement: Venture Capital and Investing
While I plan to do angel investing throughout the rest of my life, starting as soon as the present day, I would like to try my hand at really getting into the venture capital business. I think my experience being around Internet startups my entire life — seeing lots succeed and even more fail — will help me spot early stage startups.
I'd like to give back to young and hungry entrepreneurs who share my passion for startups. I also think it'll help me stay young and active to be around the spirit of these young people. I'll open my venture capital business in New York City, which will certainly be the nation's capital for investing in internet entrepreneurship by the time I'm 50 — which is 25 years from now, 2035.