Billion Dollar Advice from Mark Cuban

Powerball TicketsAmerica is the land of plenty, which means, among other things, that there are plenty of billionaires to go around. 536 of them, to be exact, according to Forbes magazine. (Wait – GoPro stock just tanked last night, so take founder Nick Woodman off that list. Easy come, easy go…) There are still a few old-fashioned heirs and heiresses on that list. But more and more, it’s made up of the “working” rich… tech titans, Wall Street honchos, media barons, and other entrepreneurial success stories.

Some of those billionaires really seem to enjoy their fortunes. I think Oracle CEO Larry Ellison ($47.5B) gets a kick out of winning the America’s Cup and buying Hawaiian islands. Oprah Winfrey ($3.1B) loves being Oprah. And think what you will of Donald Trump ($10B? $2B?), he obviously gets out of bed ready to have a good time every morning, and obviously doesn’t care what anyone else thinks about it.

Other billionaires seem to lead grim, unsatisfying lives. Casino magnate Sheldon Adelson ($26B) is the closest we have in the real world to a James Bond villain. I’d be surprised to learn he’s not assembling a private army, complete with nuclear-tipped missiles, somewhere out in the Nevada desert.

At $3B, Dallas Mavericks owner and Shark Tank panelist Mark Cuban isn’t the richest billionaire. But I think he may have more fun than anyone else on the list. As Forbes puts it:

“Cuban sold his video portal,, to Yahoo for $5.7 billion in 1999. He has since spent the last decade and a half doing just about anything he wants. His latest antics include starring as the president of the U.S. in the movie Sharknado 3: Oh Hell No! and selling Dallas Mavericks merchandise with an image of his likeness using a urinal… When Rolling Stone asked Cuban what would surprise people about being a billionaire, he responded, ‘Nothing. It’s f—— amazing and off the charts.’”

Earlier this week, Cuban offered some advice for anyone taking the newest route to ten-figure riches – winning the $1.5 billion Powerball lottery. (Sadly, there appear to be three winners, which means splitting the prize to an almost penurious $500 million each.) Here’s what he told the Dallas Morning News:

  • Hire a tax attorney first.
  • Don’t take the lump sum. You don’t want to blow it all in one spot.
  • If you weren’t happy yesterday you won’t be happy tomorrow. It’s money. It’s not happiness.
  • If you were happy yesterday, you are going to be a lot happier tomorrow. It’s money. Life gets easier when you don’t have to worry about the bills.
  • Tell all your friends and relatives no. They will ask. Tell them no. If you are close to them, you already know who needs help and what they need. Feel free to help SOME, but talk to your accountant before you do anything and remember this, no one needs 1m dollars for anything. No one needs 100k for anything. Anyone who asks is not your friend.
  • You don’t become a smart investor when you win the lottery. Don’t make investments. You can put it in the bank and live comfortably. Forever. You will sleep a lot better knowing you won’t lose money.

All excellent and entertaining advice, right? Sure captures the imagination. But wait, what was that again, back at the beginning? The very first thing on the list? Get some good tax advice first! And later, talk to your accountant first! Yeah, that’s right, one of the richest guys in America is telling new arrivals to the pot o’ gold that taxes and accounting and financial advice matter.

It’s been hard to avoid talking about the lottery the last week or so as the payout climbed to record heights. I was shopping at Philadelphia’s famed Reading Market on Monday, and the clerk at the meat stand told anyone who would listen that we wouldn’t see him again come Thursday morning. (Sadly for him, the winning tickets were sold in California, Florida, and Tennessee, which means he’s probably manning his cash register as I write these words.)

I’ve said before that one of the biggest challenges of marketing tax planning is getting prospects to think about taxes in the first place. Most people don’t think about taxes very often, mainly because they don’t want to think about taxes. And it’s always easier to join the conversation your prospects are already having than it is to start a new conversation about whatever it is you want to discuss.

But when people are already talking about income, like big lottery payouts, it’s easy to redirect the conversation to your value. When your prospect mentions shares their Powerball-fueled dreams, just ask them if they’ve thought about how much the IRS will get. Keep planting similar seeds then let them grow until your prospect is ready to sit down with you for a plan.