Naked Argument with a Billionaire  

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Perhaps it’s a bit of a stretch to call it an argument. It really ended up being more of a sales pitch. Let me explain.

Years ago, during the Dot Com boom, I was contracted to shoot portraits of the important founders, innovators and financial backers that sparked one of the most dynamic changes in history. The project gave me access to fascinating people—from Jeff Bezos to Jeff Yang. But one of the most memorable experiences came with Jim Clark.

By then, Jim was already a well-known entrepreneur and billionaire, having backed Silicon Graphics, Netscape, Healtheon, and more. In our first conversation, he mentioned that he had a private hangar at the San Jose airport housing several of his planes. I suggested a shot of him standing on the tarmac at sunrise with his custom aerobatic plane. The scene was cinematic in my mind.

But it wasn’t just about the image—it meant early morning logistics. He’d have to leave home before dawn, have his crew clean and prep the plane, and we’d need airport security clearance. A hassle, yes. But I thought it was worth it.

Jim, as it turned out, wasn’t quite as convinced.

At around 4:30 a.m. the day of the shoot, he called to cancel. I had just stepped out of the shower—still wet, phone in hand—when he told me he didn’t see the point of going through all that trouble. He explained that he preferred to stay behind the scenes, didn’t enjoy the spotlight, and had more important things to do with his time. And honestly, he wasn’t wrong.

Still, I couldn’t help myself. I offered him another perspective.

Being familiar with working with special personalities, ( like Steve Jobs or numerous celebrities), I was not dramatically surprised to receive the early morning call. But since I had just gotten out of the shower, I was little prepared for an argument.

I reminded him how unique it was that he could fly his own aerobatic plane. How rare it was for someone like him to see the value in a brand new industry so early. How those traits—the quiet power, the vision, the independence—were exactly what made him worth photographing.

I don’t remember all the words I used. I do remember looking up mid-pitch, seeing my own naked reflection in the mirror, and bursting into laughter. He heard me.

“What’s so funny?” he asked.

I told him the truth:  
“Well, it’s kind of ridiculous that a dripping-wet photographer is trying to convince a billionaire to show up at the San Jose airport at sunrise for a photo. But it really will be a cool shot, I promise.”

And he agreed.  With my humor and to do the shoot.

The photo? It turned out exactly as I’d imagined—Jim Clark, calm, confident, standing next to his custom plane, bathed in golden morning light.

Sometimes, the best pitches are the honest ones. Even if you’re naked when you make them.