Thirtysomething Entrepreneurship

As I recently hit the second half of my 30s, I must admit that my views towards entrepreneurship have changed since I launched my first comapany at 22. Entrepreneurs like myself are probably the least “career focused” people on the planet. I long held the romantic notion that I’d just keep starting companies until I could no longer form a coherent sentence. I never took the long view – always focused on the venture at hand, even the specific issue of the moment. Lately, however, I’ve become more philosophical about start-ups, risk and the long-term entrepreneurial career.

1)
30 somethings start to feel and think about their “legacy.” Perhaps intertwined in this is, unfortunately, a heightened sense of ego. Many serial entrepreneurs like myself focus on making their next venture bigger and more meaningful than the previous. It’s hard not to look at recent successes and IPOs and ask oneself “why not me?” Still, I try to not only think about building large businesses but ones that solve problems with real impact on society, with teams and products that I’ll always be proud of.

2)
The demands on time increase with age. When I started Handshake.com in 1998  the line between work and my social life was fuzzy at best. We were largely a group of recent Cornell grads who moved our all-nighters from Uris Library (sometimes!) to all-nighters building a web business.  My girlfriend (now wife) worked for free and we often wouldn’t get home until 2 or 3 in the morning. Nowadays, with 2 kids and ambitions like non-profit work, involvement in my kid’s school and a desire to stay active, the juggle of time is increasingly complex. Even one’s mortality starts to creep in the brain.

3)
For the first time, many have said to me, “the next years are your prime working years.” The unstated motive is that one should focus on earning enough for retirement, kid’s education and a place in Florida. By your mid-30s many peers have now been financially successful so even if you’ve done well, you’re likely not alone. In many cases, others seem to be working less hard and taking less risk. You can’t help but ask yourself “Am I the fool?” There are clearly easier, less stressful ways to make money, despite that they are far less fulfilling. 

That said, I couldn’t imagine doing anything else. Perhaps the problem with getting older is you think too much. Next time I won’t wait til I’m 22 to start my first venture!