One of these men is Cole Cringely

Tomorrow’s column will be all about BP, the Gulf oil spill, and doom-and-gloom, but today we’re getting ready for the Startup Tour, which begins a week from Monday.

In addition to choosing the 24 companies to visit, these days see me still seeking a single corporate sponsor for the Tour, itself. So if your company (not a startup) wants your logo on the bus along with those of the Kauffman Foundation and an unnamed-but-enormous TV network, get in touch with me soon. It’s way cheaper than buying commercials on the series, we’ll hang out together on TV, plus you get free muffins.

During last summer’s RV trip Cole, who was then age five, bitched constantly about wanting to be home. But when we finally arrived home he suddenly wanted to be back on the road. “I just realized we were on an adventure,” he explained.

This summer’s Tour will definitely be an adventure and one of my goals is to write about it every day. That sort of comes with the blogging territory, of course, but this is a rare chance that might well turn into not just a blog, but a book. I had a chance to do something similar a decade ago, blew it then, and have been kicking myself ever since.

Back in 1998 I was working for PBS and riding a popularity wave with Triumph of the Nerds. That included making appearances at member stations, especially during the notorious pledge drives. They’d air my show and during breaks I’d help the stations beg for money. One night I was doing just this at KCET in Los Angeles and it was particularly dreary. The phones weren’t ringing; the anchormen and women sitting with me on the set did not have their hearts in their work. I had to do something.

So I rashly announced that anyone who would donate $1000 or more while I was on the air that night would get all the normal goodies for that donation level plus I would take them out to dinner. We got three takers that night — three $1000 pledges — but only one person actually paid. He was a software guy from Santa Monica and we had a very nice lunch together a couple weeks later.

So far so good.

A few months passed and I found myself in exactly the same position at WNET in New York, so I made the same proposal — dinner with Bob for $1000 or more. Those savvy folks at WNET didn’t accept pledges, just donations paid in full that evening on a credit card. And when the smoke cleared 28 people had each paid $1000 for dinner with me.

Frankly I hadn’t expected that many takers. Based on L.A. I was hoping for half a dozen, maybe 10. Twenty-eight was a logistical nightmare because I lived in California and the dinners had to be in New York. Eventually I spent two weeks and more than $15,000 of my own money in the Big Apple going out breakfasts, lunches, and dinners.

It was expensive, but the people I met were amazing — so amazing that I later realized I should have written it all down and published a book, it was that good.

The common link that bound all 28 of my New York meal companions was they wanted money. There were the usual mad scientists but there was also a waiter from a Chinese restaurant who was trying to be an Internet entrepreneur (I’m sure he succeeded, he was so driven). There was a Hudson River tugboat captain who wanted me to get Larry Ellison to buy him a $31 million sailing ship. And there were two sisters in their 70‘s from the Upper East Side of Manhattan. We went to lunch at the Four Seasons where they revealed that I was supposed to help them raise money for their Broadway musical. After the second round of martinis they started doing songs from the show!

Can you see why I should have written a book?

I survived New York and in early 1999 decided to take a chance on doing the same thing at KQED in San Francisco. The market was smaller than New York so I expected fewer takers. I was living then in Silicon Valley so my expenses would be lower.  What the heck…. The morning after found 18 new $1000 donors to KQED.

It took me a few weeks to take all those people to dinner and you know they were completely different from the donors in New York. None of the San Francisco donors were looking for money. They wanted to talk about ideas. My guests included a noted greeting card designer, several famous and semi-famous nerds, and a couple of single ladies who thought I was kind of cute.

I’d do dinners like that all the time in San Francisco if I could afford it.

Remember that was the height of dot-com fever when everyone in the Bay Area seemed to be rolling in dough. If I were to do it again in 2010 the results might be different, but I’d still expect the currency to mainly be ideas.

My final dinner from that KQED experience was with a guy who worked for DHL on the company’s web site. It was April 20, 1999. Near the end of dinner he called his room mate (a woman) and asked her to join us for dessert. I’m still friends with many of those KQED donors including the guy from DHL. And eleven years and four children later his old room mate is Mrs. Cringely.  We’re still together, still on an adventure.

I should have written that book.