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13 Things Silicon Valley's Uber-Wealthy Entrepreneurs Should Spend Their Money On

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Here at Racked, we're dedicating this week to the kind of fantastical shopping that most of us only get to experience in dreams (or at 80%-off sample sales). Taking a page from casino parlance, we'll be talking a lot about "whales," those big spenders who feel perfectly comfortable dropping tens of thousands of dollars every night on roulette, or, in our case, on Cartier. Welcome to Whale Week 2013.

Image via Yachts123

San Francisco Bay Area wealth seems to come in two flavors. There are the Gettys, the Trainas and the Steels, with their mansions, charity events and gala symphony openings. Then there are the dudes in hoodies.

They make millions from their startups, but wouldn't dream of pulling up to their Mountain View office park in a Ferrari. They might fly their private jet to a meeting across the country or vacation on a luxury yacht where they're not likely to be (but sometimes are) seen by the masses. Flaunting is aggressively frowned upon. Legend has it that one Google executive warned he would take a baseball bat to any flashy sports car that showed up at work the day after the company's IPO.

Several VCs and tech moguls contacted for this post declined to share their favorite shopping haunts, brands, purchases, etc., because showing it off is so uncool in Silicon Valley. Stewart Alsop of Alsop Louie Partners had this to say:

I agree that it is frowned on. And should be. If it's just about the money, then it's flaunting. But having money is the path to being able to appreciate quality. What I really appreciate is the quality of attention to detail in things that are made by craftspeople: Jewelry. Shoes. Dresses. Cabinets. Furniture. But not mass-produced products like cars, furniture, jewelry, dresses, shoes, etc. So I think being ostentatious about spending is really a turnoff; but being knowledgeable and careful about what you are buying exceeds the price you are paying for stuff.

So what IS acceptable for Silicon Valley's fabulously wealthy spend their money on? Here's a short list of some already acquired, and some recommended purchases:

1. Hand-painted Italian bicycles

2. Bansky art

3. Maybe a nice car, just don't drive it to work, DO NOT post it on Facebook.

4. A house, but most of it should be underground

5. Vacations on private yachts with models

6. A private island

7. A ski trip at an isolated resort in West Greenland

8. A private jet

9. A submarine

10. Super Bowl tickets (GO NINERS!!)

11. Long pants

12. Fancy socks

13. Philanthropy