Cynically Optimistic

Or as it is also known, The Wolfman Jack Memorial "I'm totally gonna win the lottery and do all this cool stuff with the money" post. How many times have I had this same telephone conversation? At least 10 times with Jack, probably the same number with Wendy. This time, the question was posed by Jeff Utech. At a bookstore in Coconut Grove in Miami a couple years ago, I thumbed through a book titled, "How to Win the Lottery and Still be Happy" (or something close to that). This book offered several bits of wisdom that I never would have thought of had I just seen my numbers flash on the TV screen when I won that amount of money.

First off, you cannot tell anyone. Not your wife, not your mom, not your best friend. Nobody. This has got to be the hardest part, because I'd be ready to explode with that kind of news. Second, hire an attorney and make him sign a non-disclosure agreement right away. Wait at least 3-6 months before having the attorney claim the prize money without using your name (you have up to 1 year in most cases). Third, Do not quit your job for 1 year (although I bet after a few months it would be ok).

The book also offered advice on how, after the initial shock wears off, smarter ways to reduce your tax burden and donate to charities without bringing a lot of publicity to yourself. One thing the book stressed is that it's hard to keep your family and friends on good terms after winning, because money changes things. Everybody thinks they deserve a piece of you, and folks will come out of the woodwork asking for a hand out. Imagine being called every day by dozens of charities, each deserving, and having to constantly tell them no (or some of them no, anyway).

I'd donate some serious cash to fund research on diseases such as diabetes and AIDS. The amount would have to depend on what's allowed with the tax code, but probably around 50% of the lump sum amount.

All that aside, after the dollar bills settle, and I've got a huge wad of cash (because obviously I'd take the lump sum) I would hire a financial advisor to help set me up. A team of financial advisors, actually. Preferrably led by Suze Orman (LOVE her!). It's been a pipe dream of mine to have homes in various fabulous locations around the world, so I would make some smart investments in places like Manhattan in a fabulous pentouse in a classical building with fantastic architecture, but completely modernized. In San Francisco I'd have a nice Victorian home made out of old redwoods. A comfortable flat in Seattle. I'd buy a nice big ranch in Jackson, Wyoming, and staff it to care for the horses and grounds. Finally, I'd buy a villa in Lake Como, Italy, for when I want to go pretend to be fabulous.

Instead of flying commercially, I'd have to become a member of something like Marquis Jet so I could collect people on a whim and jet off to fabulous worldwide events. From now on, I travel in style. I get myself a personal trainer and private chef, but no hair plugs. I'm gonna be rich AND hot.

One of the crazy things we end up talking about is buing some big house near the HMB practice field to house the Saxophone section. Also, completley re-do the practice field so it's level and there are no holes in which to twist your ankle. You know you've got to give back to your band geeks. Also, I'd have a private box at Kinnick stadium, and good parking place. I wonder if the hospital would let me land a chopper on the roof?

Now, when it comes to giving things to people you love it gets tricky because you must draw the line somewhere, and people will invariably get pissed off. But I'll try anyway. I'd pay off my family's debts. I'd buy them all fancy cars. Wendy gets a Mini Cooper S. Actually, everyone gets a Mini Cooper S. Except Jack, he gets a Harley and lessons on how not to die while riding it. If you've got a baby, he or she gets a college fund. If you are childless and fabulous, you get plastic surgery (if you want it). And somebody is gettin' a platinum grill, yo. Fo' Shizzle!

And I think I'd still keep my job.