What's your outlook for 2017?
It all depends on what the new government starts to do. With that said, I raised a few million dollars in November. I want the markets to go down, because then I get to buy. And if I buy dividend-paying stocks, I am getting a higher yield.
And you think that's what will happen in the coming year?
Maybe. Either way is fine with me. I have all these bonds that are about to come due and were giving me 6.75% interest, tax-free. If the market goes down, some of that money will go into dividend-paying stocks. If not, I am finding municipal bonds that give 3.5%, and that is fine, given that I like to keep my money safe and sound.
What has been your best investment?
Probably Apple stock. Now, I am loving Tesla. I'm convinced that it will no longer be a car company—it is a battery company.
What's your biggest regret?
My biggest regrets have always been that I did not hold on to stocks long enough.
Can you give me an example?
If I had just held Amazon this entire time, are you kidding me? Same with Facebook.
What's your investing philosophy?
If you will not throw up if the market goes down 5,000 points, and if you have time on your side, you do not have to sell.
And you have the stomach?
You betcha. I'll tell you why. I own everything outright, and I always have a few million in cash on hand, and 90% of my portfolio is in municipal bonds. So if I lost all of the other money I have in the stock market, it still wouldn't affect my lifestyle.
How has your investing process evolved?
I still like to punt a little—buy a stock at 50 cents and see what it will do. I loved to do that from day one as a stockbroker, but I never did it for my clients. I seldom would invest in the same stocks I'd sell to clients. It just becomes too emotionally charged.
What do you think will be the next big investing trend?
I am a firm believer that in five or 10 years, many, many jobs will be replaced by robots or artificial intelligence. So that's my biggest fear: that people eventually won't have jobs.
Do you think you'll ever retire?
I already have. I now live on a private island in the Bahamas. I think TV and books will become obsolete, which is why I am not writing any more books. But I don't want to walk away from the people who have nobody to guide them. That is why I'm working on a bot to replace Suze Orman. Shortly, I will be the personal finance adviser to the world via a bot. I am not kidding.
But you do continue to run your own investments?
That will never stop. A year ago, I started to invest in gold—we fund small gold mines, and they pay us back in gold. So if we lend them $25 million, it gets paid back at $400 an ounce for the life of the mine. And we can turn around and sell it for $1,300 or $1,400.
What are your hobbies?
My new love in life is fishing—I do it at least five hours a day. My wife, KT, and I have our own 32-foot fishing boat. We just caught our first two wahoos, which is a very hard fish to land without killing yourself.