ImagesI’m not sure if I should call myself an entrepreneur, an impresario, a salesman, a visionary, a marketer or a just crazy fool in an even crazier world, I confess to my old friend Tessa Ross.

I have to raise my voice. We are sharing an organic cherry pie at COCO 500, the Web 2.0 restaurant that has replaced that old Web 1.0 haunt, Bizou, on the corner of Fourth at Brannan. The formerly mustard yellow restaurant is packed with noisy diners. Today, the cash is back in San Francisco; today, nobody is singing for their supper. 

Ross and I are talking about my life over the last fifteen years, ever since I arrived at San Jose airport with a backpack and a desire to "get into new media". I know mine is a Silicon Valley story, I tell her, but I’m still not clear how to identify myself? It’s a struggle to connect all my dots, I explain, and even when they are joined, I’m not quite sure what I see.

Ross is visiting from North London, my original home. Her real business in California is in Hollywood, but she has hopped up from Los Angeles to lunch with me. We have been friends for more than twenty years. In 1984, I left London for America;  she stayed and entered English media. Ross is now a mogul. She heads up film and drama at Channel Four and is the producer of many well-known movies including the Oscar-nominated Billy Elliot (2000).

“Andrew, there has to be a single word, just one word, that summarizes what you’ve been doing in Silicon Valley all these years,” she says. The pie is finished now. All that is left are eight empty cherry stones.

A technology idealist, I suggest.

“That’s two words.”

If you ask my friend Rosebud or Larry and Sergei at Google, they would say I’ve failed. I haven’t made their billions, I admit. In fact, I’ve lost quite a lot.”

“How much?”

Financially or mentally, I ask.

“Hard cash,” she says. “In dollars and cents.”

I close my eyes and picture my digital ventures – everything from Fi: The Magazine of Music and Sound to Audiocafe to MB5 to Pulse 3D to Santa Cruz Networks. I grab a COCO 500 napkin and write a five numbers down. Then I add them all up.

Close to a hundred million, I tell her. Not counting the cents.

Momentary silence while Tessa digests the number. “And that’s other people’s money?” she asks.

Pretty much, I admit. Mainly venture capital. But also angel investment including Rosebud’s cash. And some of my own, too.

Tessa is playing with the cherry stones in front of her. “Tinker, tailor, soldier, sailor,” she begins to recite the old children’s nursery rhyme. With each word, she drags another cherry stone across the plate.

I am still searching for that elusive word to describe myself. How about a dreamer, I suggest. A Silicon Valley dreamer?

“Rich man, poor man, beggar man,” she continues, raising her voice above the din of the COCO 500 lunchtime crowd. There is only one uncounted cherry stone left now.

Over the last twenty years, I’ve been everything in that nursery rhyme. I’ve tinkered with business models. I’ve tailored digital media business plans. I’ve soldiered in the trenches against traditional media. I’ve been a sailor in the high seas of digital piracy. I’ve been a rich man in theory and a poor man in fact. I’ve begged money from every venture capitalist in the Valley.

Ross fingers the final cherry stone. “Thief,” my old friend concludes, unable to restrain a smirk.

I feel myself coloring with a mixture of pleasure and shame. Tessa Ross has nailed me. It is the single word that joins all the dots and turns me into what I really am.

“Come on, Andrew. Confess,” the North London mogul says, rubbing her little hands together hungrily. “On top of that hundred million dollars, tell me what else you’ve pinched recently?”