How about personally -- even something as subtle as a surprised glance when you come into a meeting? Courtot: If I've talked with someone a lot on the phone, and then they meet me the first time, sometimes there will be surprise. "I thought you were much younger!" they'll say. I think it's because I look my age, but I don't really act it.
Massaro: When I come into a meeting, it's not like Father Time just walked into the room. I don't look my age, and I certainly don't act it. We also sell to large corporations. There are a lot of senior people in their 50s and 60s at those meetings. The people making decisions are a lot closer to my age than that of my salespeople.
Noerr: I was once sitting in a train and the conductor came by and patted my hand and said, "Dear, you don't have to pay." And I asked why not. "Because you're elderly." I should've pleaded with him to take my money. I hope I don't look or act that old. But that doesn't matter. It's just vanity.
What have age and experience taught you? Massaro: At my age today, I've had it all happen, so I've got a lot of confidence. Now I try to encourage an open environment where people feel comfortable challenging me. For [less important] decisions, I've learned to let others do it their way, even if I disagree. Unless I'm sure they're going to electrocute themselves.
Noerr: I know that management is not my strong suit. I've learned to create a layer between me and the rest of the company. I used to try to get companies to run before we could walk, or spread our resources too thin. We haven't made those mistakes with MuseGlobal.
Courtot: I understand now that ego and drive aren't intertwined. Without the impatience of youth, you can look at things with a more detached eye. You don't have ego interfering as much anymore. You don't also lose your drive to achieve or the ability to act aggressively. When I was younger and I read about senior leaders, I couldn't understand that.
Noerr: I'm in a club that's literally called the Grumpy Old Ladies Club. We're all about the same age, and have all done something like start or run a company. And we're all grumpy. We say what we want, say what we mean. If we get bored at a talk, we don't stay.
What has failure taught you? Massaro: My very first gig [as 29-year-old CEO of Shugart] was a success. It goes straight to your head. All of a sudden, you feel like Superman. A really serious failure, where you fall flat on your face, teaches you that sometimes you can't get there from here. It also helps your management style when you've failed big time and can convey that to people. You're human to them.
Courtot: With cc:Mail, we essentially beat Microsoft with just 45 people. Then we made the mistake of selling to Lotus. I got a very good price. But within one and half years, Lotus replaced cc:Mail with Notes. And IBM shut cc:Mail down despite 20 million users. I felt very sad.
Massaro: I was CEO of an environmental products company that I funded myself and lost a ton of money on. They call that self-embezzlement.
Seriously, I've learned that so much success in the Valley comes from being in the right place at the right time with the right product. At the same time, you have to know what time it is and where you're standing.