Failure as an event

I try hard not to keep a running tally of big-time failures in my head. It gets in the way of creating the next thing. On the other hand, when you see failure as a learning event, not a destination, it makes you smarter, faster.

Some big ones from my past:

The Boston Bar Exam. My two partners and I spent a lot of time and money building this our last year of college. It was a coupon book filled with free drinks from various bars in Cambridge and Boston. The booklet would be sold at the bars, encouraging, I dunno, drunk driving. Lessons: Don't spend a lot on startup costs, don't sell to bar owners and don't have three equal partners, since once person always feels outvoted.

The Internet White Pages. This was a 700 page book filled with nearly a million email addresses. It took months to create and IDG, the publisher, printed 80,000 copies. They shredded 79,000 of them. Lesson: If the Internet Yellow Pages is a huge hit (it was), that doesn't mean the obvious counterpart will be. A directory that's incomplete is almost always worthless.

MaxFax. This was the first fax board for the Mac. It would allow any Mac user to hit 'print' and send what was on the screen to any fax machine. We raised seed money from a wealthy dentist, built a working prototype and worked to license it to a big computer hardware company. Lessons: Don't raise money from amateurs, watch out for flaky engineering if you're selling a prototype, think twice before you enter a market with one huge player (Apple knocked off the idea) and don't build a business hoping to sell out unless you have a clear path to do that.

I have a dozen more. The first wireless Sonos-like device. A nationwide game show using 900 numbers. A fundraising company that offered lightbulbs for sale to high school bands (lighter than fruit!). Not to mention classic book ideas like, "How to hypnotize your friends and get them to act like chickens." I'm not using hyperbole when I say that in 25 years, I had at least 20 serious career-ending failures.

I guess the biggest lessons are:

• Prepare for the dip. Starting a business is far easier than making it successful. You need to see a path and have the resources to get through it.
• Cliff businesses are glamorous but dangerous.
• Projects exist in an eco-system. Who are the other players? How do you fit in?
• Being the dumbest partner in a room of smart people is exactly where you want to be.
• And the biggest of all: persist. Do the next one.