Starting a Business: It's Good to Be Old

July 25, 2008 — -- At age 54, I've just started two companies.

And what I've already learned from the experience is that not only am I more suited for the task now than I was at 27 or 38, but that the world of entrepreneurial start-ups is now much more suited for me. And for you.

Let me start by giving you a little background (and I should also note that any companies I mention in this article, by definition, represent a conflict of interest on my part and you should in no way take my comments as an objective appraisal or a recommendation).

Having grown up in Silicon Valley, and then having spent a decade as a journalist writing about other people starting companies, I finally decided to try my hand at entrepreneurship in my early 30s. I was one of those people -- by far the majority -- you don't read about.

One company I helped start got no further than a sophisticated business plan and a tour by the founding team of venture capital firms -- where it got shot down. Another lingered on for nearly two years, with a great product idea, a dedicated team and even some money.

My business partners and I put in endless hours, begged funding from friends and family, but in the end, we lacked the ability to take it to the next step. We had been too dreamy about our idea, too unwilling to focus on a single strategy, too unprofessional in our organization -- and now we had to go back to all of those friends and family and tell them we'd lost their hard-earned money. I've never quite gotten over that one.

I also tried my hand at angel investing, putting money into two start-ups that, amazingly, are still around a decade later. But they have never gone public, nor been acquired, so my investment still sits there, slowly being diluted, a perpetual lesson that there is a third fate to start-ups besides success and oblivion: endless limbo. I have nothing but awe for the entrepreneurs at those companies, who have devoted a vast chunk of their lives in what must seem like an endless, lung-burning, side-cramping sprint.

In my 40s I ran one of Forbes' magazines. Directing my hand-picked team, based in offices in Silicon Valley, and with a laissez-faire parent company 3,000 miles away that behaved pretty much like a venture capital firm, I got my first taste of what it's like to be the CEO of a successful start-up. During the dot-com bubble years, when running a magazine was like printing money, the experience was exhilarating. But when the bubble burst and Forbes pulled the plug on my magazine, I finally got the painful lesson eventually learned by every entrepreneur: Even when you are in charge, you aren't necessarily in control.