The Old Startup Guy

I'm sure many of you spotted this article about the "new guard" versus the "old guard" of Silicon Valley.  The article is uniquely insightful and detailed, a pretty accurate view of what draws and keeps people in Silicon Valley.

As someone who is nearly 35 and "over the hill", I'd like to give my own perspective on the topic.  I feel somewhat knowledgeable on the topic, since I lived and worked in the valley for nearly four years, and I worked at several  startups over my life, and now I work at one of the "old guard" companies named in the article.  I guess I fit the mold pretty well.

I loved working at a startup when I was young.  We wrote code, played video games, had nerf wars, played soccer, had parties together and generally just tried shooting the moon and having good times as a group of friends trying something big.  We worked long hours (we actually got paid by the hour, which when you are 21, was amazingly good pay, and for the company, it was a steal to get developers that cheap)  Those times were perhaps the most fun and memorable times of my life, and I would give nearly anything to do them again.  It all worked out at the time because the pay was really good for living in a house of 7 roommates and eating Domino's pizza.

I imagine this is exactly what Silicon Valley is like today, and this article seems to confirm it.  Trying to make something cool and fun while working / living / partying with smart people, and having one small sliver of a shot at making it really big.  It gives me chills just thinking about it.

But it doesn't last forever.  You eventually either get old, or sick of it, or find someone and settle down and have kids, or really sell the company for a billion dollars, or fail so hard you have to move home, or whatever.  Then what?  You have to pay a mortgage, take kids to soccer practice, work less than 80 hours a week because there are people who want to see you, live in the valley because soma got too expensive, and work at a job that will really be there next week because health insurance ain't free.  And then you're working the "old guard" making routers and measuring email uptime because it means all of those things.  

There's a generation of us "old people" working at those "old guard" companies because risk tolerance is lower and having a family will always come first.  Hell, I'd work at a startup in a heartbeat if it meant I knew I loved what they were doing, it would afford my mortgage, and I could see my kids.  I'm sure a standing army of similar "over the hill" hackers and hustlers working at the old guard companies are in a similar position.  

These "new guard" companies are designed specifically to work as high-risk-high-reward, time-intensive ventures that don't fit the needs of someone with something to lose.  When I kick off my startup -- and I will -- there will be several rules that I will need it to live by to make it viable for me, as someone with something to lose:

• There is a clear separation between work and home life.  I'm all for being good friends with who I work with, but you've got to have time apart to stay sane.
• Some time during the day is going to be for my family, and is non-negotiable.
• The benefits have to work for everyone.  Having unlimited Ramen and Mountain Dew is great but pales in comparison to health insurance.
• If and when I sell, I want to make sure every employee walks away well-off.  None of this "liquidation preferences" bullshit.

Anyways, perhaps it's all just hot air because I haven't gotten off my butt and just done it.  But perhaps these are just the words to my future self.  Good luck, buddy.