M*A*S*H Star Turned Mogul Wayne Rogers Blasts Tax Code, Offers Tips

“Shoemaker, stick to your last!” was never an adage in which “M*A*S*H” TV star Wayne Rogers — a.k.a. Trapper John McIntyre — put much stock. While notching more than 70 screen credits over five decades, the actor was simultaneously building an even more successful career as a shrewd investor and entrepreneur embracing an array of businesses in which he had neither training nor experience.

Playing an affable Army surgeon in the CBS sitcom version of “M*A*S*H” (1972-1983), Rogers — together with Hawkeye, Hot Lips and Radar – used humor to help face Korean War horrors. Off-camera, Rogers, a Princeton grad, was busy investing his TV earnings in the market and even launched a firm to help other actors — including ex-roommate Peter Falk — rock stars, producers and writers with their investments and money management.

To date, helming Wayne Rogers & Co., the Alabama native has turned around troubled businesses; developed real estate; and co-owned a film distribution company, a vineyard, a restaurant and hotels, plus produced feature films, TV movies and hit Broadway shows.

Further, Rogers is CEO-chairman of Stop-N-Save convenience stores, chairman of the famed bridal boutique Kleinfeld, and on the board of Vishay Intertechnology. A founder of the Plaza Bank of Commerce and Premiere Community Bank of the Emerald Coast, he is also a principal owner of Delta Pacific Transportation Co.

Somehow, the multi-talented 80-year-old finds time to appear regularly as a panelist on Fox News Channel’s “Cashin’ In.”

His book, “Make Your Own Rules: A Renegade Guide to Unconventional Success” (AMACOM Books 2011), details the actor’s unorthodox rise in the business arena.

And Rogers’ post-“M*A*S*H” acting resume is nothing to sneeze at. Leaving the series after three seasons, he co-starred in the feature “Ghosts of Mississippi,” joined the cast of TV’s “House Calls” and guest-starred on a slew of other series, including “Murder, She Wrote” and “The Larry Sanders Show.” In the early 2000s, he was still snagging gigs.

Back in his Navy days, betting he’d earn a sizable sum someday, Rogers wanted to learn how to handle money wisely. He studied the market and put his knowledge to work managing a mythical $100,000 stock portfolio. Later, as an actor he hightailed it to Hollywood. Soon he was earning enough to invest for real.

ThinkAdvisor caught up with the outspoken Los Angeles-based Rogers to talk taxes — and, as it turned out, much, much more.

ThinkAdvisor: Do you still act?

Wayne Rogers: A friend who saw me on “Cashin’ In” said, “You don’t know what you’re talking about!” I said, “That’s why they call it acting!”

Do you manage money?

I’m not a registered advisor, so I don’t do it for a fee. But I do manage money in partnership, and I do small private placements in companies under $50 million in sales. Sen. Ron Wyden of Oregon, head of the Senate Finance Committee, has called the federal tax code “a dysfunctional, broken mess.” Agree or disagree?

Of course it’s a mess! The tax code was passed by people who don’t know what the hell they’re doing. It’s filled with all kinds of exceptions. The biggest problem is that corporate taxes in the U.S. are greater than they are overseas. So multinational companies leave most of their money overseas and avoid taxes in the U.S. It’s not evasion; it’s avoidance.

Suppose an individual wants to sell their business. What should they bear in mind tax-wise?

If your tax basis is very low and you sell it for very high, you’re going to pay a big tax. There are all kinds of things you need to do to limit your tax: If you’re a private owner of a business in your name and you haven’t done any tax planning along the way, then you’re in trouble because you’re going to give it away to the government. And that’s just dumb.

What if you own a family business?

The best thing to do is form a partnership with your children way beforehand so that you give it to them during your lifetime. That way, when you die, it’s not going to get taxed very much. If you want to sell the business, at least the basis is now down to a different level. After you die, the basis gets reassessed from the date of your death. So, if you bought the stock at $2 and it’s selling at $100 when you die, the basis will be $100; and no tax is required to be paid on the difference.

What’s the tax liability when you own a large position in a single company?

 The guys who ran Microsoft got rich by owning Microsoft stock, not by diversifying. But they don’t want to give it away [to the government]. That’s why Bill Gates is donating his money to his foundation. Anybody who’s wealthy didn’t get wealthy by being dumb. So he’s putting the money in a foundation that can be run by intelligent people and will do some good. They’re much better caretakers and spenders of wealth than the federal government.

Is tax-loss harvesting, selling an investment at a loss at the end of the year to offset capital gains, a good strategy?

Absolutely. If you’ve got a loser and some gains, why would you want to pay the government? Anything you can do to avoid giving your money to the government, you should do. They’re in the business of distributing wealth; individuals are in the business of building wealth.

Any other thoughts about estate planning to keep one’s tax bill lower?

If you don’t estate plan, you’re crazy. But you have to know all the nuances. You planned ahead by teaching yourself about the market while you were young. What was behind that?