With all the stock market volatility lately, I’ve almost been able to convince myself that I did the right thing a few years ago by exiting one of my “buy & hold” portfolios early. I say almost because I made a handful of bets in 2002, and called the portfolio “60-Month Hold” as a reminder not to sell early.

What was in the portfolio? Oh, Apple (AAPL) at 18.99/share. Akamai (AKAM) at $3.88/share. Toyota (TM) at $52.50/share and Target (TGT) at about $36/share. The net gain on these holdings when the 60-month hold expired would have been around 500%. Unfortunately, I only made it a little past the 24-month mark before I decided to re-deploy the capital. (I also moved several hundred ounces of gold into other investments, having paid about $273/ounce against today’s $1,000/ounce.)

Maybe it’s lemons to lemonade, but I do see a lesson for myself here that will ultimately be much more valuable than anything I could have made on this portfolio in the market. I was convinced that these companies would be good investments in ‘02, and I even took a fair bit of ribbing from a senior investment manager at Bank of America for choosing these companies at the time.

Today, some people definitely question my opinion that viable startups need to build partnerships and revenue (not just audience and hype) in 2008. I was willing to make a pretty big bet on this gut feeling when I decided to leave my startup 2.0 in a quest for “the next big thing.” Maybe we can revisit the topic in 24-months to see if the fraction of equity I left behind would have been worth a longer full-time commitment on my part.