So talk about pie is all well and good. But what about all that time things are baking in the oven?

Without a doubt, my biggest challenge when running companies has been finding that magical balance between collaboration and leadership. I come from a family of educators, so I’ve grown-up with the notion that the best solutions give everyone a chance to perform and elevate their skills. But the “real me” has some strong opinions about how to innovate and invent (or re-invent) markets.

Mid-2001 is the time when I probably made one of a handful of mistakes that eventually crippled my first startup. The writing was on the wall for e-services even before September 11th. The market for custom Website development was becoming saturated and the big guys (like IBM) were starting to compete heavily for large jobs. I knew we had some viable products and I called an employee meeting to talk strategy.

I should have been the captain of the ship and said, “Look…We’ve looked through the telescope and can see that e-services work will be slowing down. We, as a company, are going to stop making other people money for their products and focus on building a product of our own.” Instead, I articulated a handful of product ideas where we had patents pending and asked people to raise their hands if they wanted to stick with services or try one of these new things.

Almost everyone voted to stick with e-services instead of venturing into the unknown. I shouldn’t have been surprised. Until a ship is completely capsizing, most people would probably opt to stay onboard while the boat is taking on water rather than jump into what could be a shark-infested ocean.

It’s no exaggeration to say that the products we talked about that day were working prototypes of what other people turned into Kayak, Spiralfrog and Dodgeball. The aggregate acquisition prices and funding rounds for these companies has been in the hundreds of millions of dollars. The dying days of IPI’s e-services were only a fraction of this amount, until the services ship did ultimately completely sink.

If I had it to do over again, I would have articulated a clear vision for one of our products and said, “This is what we’re doing.” I would have given people who didn’t believe in the product a chance to leave with some severance so that everyone else could get on to the next big thing. The office would have switched from nervous same-thing-as-yesterday mode, to optimistic dreaming about the future. I’m sure some good people might have stayed longer as a result.