Larry Ellison’s personal spending

Inside look at a billionaire’s budget / Larry Ellison’s spending worries his accountant

So how could someone with $17 billion cause his accountant to worry about running low on cash? Ellison, who identifies strongly with the company he founded in 1977, has been famously unwilling to sell Oracle shares over the years.

Instead of selling them, he has financed his lavish lifestyle — the 23-acre Japanese-style estate in Woodside, the yachts, the airplanes, the Armani suits — by borrowing against his stock.

“I know this e-mail may/will depress you,” Simon wrote in a 2002 note about diversification. “However, I believe it’s my job to address issues you’d prefer not to confront. You told me years ago that it’s OK to raise the ‘diversification issue’ with you quarterly. … Well, I’m doing so. View this as a call to arms.”

This wasn’t the first time Simon had sounded the alarm. In 2001, Ellison’s spending was on an upswing, and his debt level was increasing rapidly, Simon said in a 2004 deposition.

Simon tried to explain to Ellison the seriousness of his debt, saying, “We have a freight train going down a track, hitting a debt wall,” he said in the deposition.

Wow… 23 acres. As someone who was born in Brooklyn, lived in Queens, the border of Long Island, Baltimore, then the Bay Area – I really can’t imagine what 23 acres would look like.

That said – I can see how Larry would run into money problems – it’s expensive here!