I don't know how long I've known Teddy, but Teddy's not the kind of guy where that sort of thing matters much. You could know him for a day and feel like you've known him your whole life. He lays himself on the line, blemishes included, and you either love him or don't know what to make of him.

I vividly remember the day we met. He shocked and intrigued me in a singular moment of introductory candor. He approached me and asked if I was the guy who wrote the book on retirement. Teddy said his brother was currently reading the book and noticed that the author lived in our town (Rochester, Minn.) and wondered if he happened to know him. Teddy told me that he told his brother, "I don't know him, but I think he's the guy married to the gal with the great legs." I laughed so hard I almost fell over. I knew immediately that this was not your average guy on the street and that I would enjoy talking further with him. We conversed and chortled a while longer and agreed to have lunch sometime down the road.

How memorable that lunch would prove to be. Timing played into the equation, as it was 2008-the beginning of the meltdown, when people were questioning all things around money. It was a time when I was searching for wisdom to pass on to financial advisors to better understand their clients' personal dilemmas and financial philosophies. Teddy would prove to be an inimitable source for salient insights.

Teddy is a successful businessman and comes from a family of first-rate entrepreneurs with eyes for opportunity and appetites for risk. I told him I wanted to talk about money-the good, the bad and the ugly. He liked the topic, so we picked a favorite restaurant where we would meet.

A lunch with Teddy may well go on for two hours plus, but there's a reason for it. The first thing he'll tell you as you're sitting down is, "See these ears? I'm donating them to the Gift of Life Transplant House when I die ... because they've never been used." This is the first stitch in what will be a kaleidoscopic quilt of wisecracks, self-flagellating analysis, stories and memories punctuated with pithy summations. I don't know that I've ever laughed harder or louder in public or had to fight harder for a check. I may have lost on that count, but I won in what I took away.

Teddy began to tell me his story: how he was the youngest son of a first-generation immigrant from Greece; how his father worked harder than anyone he had ever seen in his 24-hour diners; how his dad never once took a day off; how he and his family had once gone to Greece (his dad stayed behind to work) and seen the mud-built house his father had grown up in; how his father had died when Teddy was only 13; how Teddy had to help his mother pay bills by writing out the checks for her as a teenager; and how he had dropped out of college because he realized that what he needed to be successful as a businessman wasn't going to be found in a textbook. Working hard, seeking opportunity and scrapping for "everything you got" were infused into his DNA.

This stream of consciousness autobiography was seasoned with the occasional "Can I tell you something?" which was followed by an interruption of insight that had been thought out long before lunch.

On enjoying your money: "Can I tell you something? The only money that's really yours is the money you spend. Everything else will go to somebody else: your kids, a charity, Uncle Sam. Think about it-the money you spend is really yours. You get to enjoy it. The rest ends up in somebody else's hands, and there's a good chance they'll waste it."

On how to go broke: "Can I tell you something? You won't go broke from consumption; you'll go broke from bad business deals. Can I tell you how many times I've lost good money in bad business deals? I lost money because somebody told me about some great opportunity halfway across the country, and yet the people who lived there-where the so-called opportunity was right in their backyard-knew there was nothing there. My whole life I've seen these guys that'll pinch pennies at the restaurant, not order a drink or something, and yet throw dollars to the wind in stupid business deals. Somebody comes along and makes them feel special or important or smart and they throw their fortunes at deals that ruin them. I'm going to enjoy my meals, my car, my opportunities to enjoy life, but I'm going to be really careful about a 'great opportunity.'"

On giving anonymously: "Can I tell you something? The hardest thing I ever did was give anonymously, but it was the best thing I ever did. I was at an event and they were recognizing and applauding all these guys who had given less than I had, and so I'm driving home thinking, 'What the %#@^ did I do that for? All these guys get cheered, and I gave more than all of them.' But you know something? Something inside me started feeling good about the fact that this time I didn't need the glory-just the satisfaction of doing something good. And today I still feel great about it. That good feeling will always be with me. As a matter of fact, it only gets better."