Most of my clients are happily married, which is to say, happy to have 100 percent of their money versus 50 percent. That’s good. Because, in my experience, men who get divorced late in life make horrible clients. They don’t have enough money to retire, they think they can do everything financial on their own and they’re more interested in performance-chasing than long-term planning. That’s probably why they’re divorced in the first place.

Divorced guys who are still rich, however, are more interesting. Let’s take two examples: I call them the do-over and the continuity player.

In Mad Men season five, episode six, Roger Sterling’s ex-wife says to him, “I thought you married [the younger woman] because I had gotten old, and then I realized it was because you had.” That’s the do-over. One of my clients runs a successful chain that sells stuff—let’s just call it “hamburgers.” At 62, he is married to a svelte 41-year-old, and they have a young son. She comes to all of our meetings. She hates any mention of my client’s first marriage and the two daughters it produced. I don’t blame her for that: She’s just protecting her interests and those of her son. True, the more she talks about how she earned an honest buck and worked hard her whole life, the more brightly her opportunism shines. But her husband is the real issue.


You see, some time around age 45, a guy starts to wonder about his future. Does he have enough to retire? What’s he doing with some stock-trading portfolio, buying crap from tips he heard on CNBC? With clients older than 45, I can have a productive conversation.

But the man who marries the much younger wife has magically transported himself back to 40—still five years away from an adult conversation. Now, every time he gets close to asking the right questions, he’ll convince himself that his ad hoc decisions are actually a plan. Or the wife will interrupt and tell me how they’re doing just fine.

Not really. My 62-year-old client should be working on selling this company and living the good life. But no, he wants to avoid the issue: He’s built his company from nothing into an eight-figure enterprise and hasn’t started working on his liquidity plan, succession plan or any plan at all, really. Maybe by 70 he’ll start thinking about it.


Then we have the continuity player, like another of my clients, this one in the gas and oil business. He grew up poor and worked hard his entire career. All that work took a toll on his marriage to his high school sweetheart, and the marriage didn’t survive. Both my client and his ex remarried spouses of similar ages who had teenage and adult kids of their own. His new wife lets him run his business and is happy she found love the second time around, with lots of money to boot. She doesn’t try to compete and seems to simply want a person to spend time with. The situation between the two families is generally amicable, and everyone gets along around the holidays.

This partnership is the continuity of the client’s life and business. He is 55 and acts it. He organized the sale of his company to a private equity firm that didn’t know his business and overpaid. After he got pushed out, he started his own firm, and now money is flowing again. What I like about his continuity is that he knows where he is in life. He never tried to become young again. We have a great time working on tax planning, risk management and other exciting topics. They may not be as sexy as a trophy wife, but he doesn’t seem to mind.