The Rich Man's Guide to Modern Family

Brunch with Craig Goldman is a spectator sport. At 55, he’s not just playing the game, he’s running the whole damn league. He’s the guy in the corner booth, cracking jokes that only other people laugh at, sipping a double espresso like it’s a statement of intent. Craig’s worth about $100 million—a self-made trading firm titan who can calculate your net worth faster than you can pronounce “private equity.” But this morning, over Eggs Benedict and Bloody Marys, he’s chewing on something a little harder to swallow.

“I want a family,” he says, cutting his toast with the precision of a man who’s never done anything messy. “But finding a wife? That’s like trading on bad intel.”

The problem, as Craig sees it, is generational. “Women in their 20s don’t want husbands; they want hashtags,” he says. “And the ones in their 30s? Don’t even get me started. They’re feminist, self-centered, and resentful of tall, Ivy League alpha males.” He pauses for effect, flashing a grin that’s more spreadsheet than sentiment. “And guess what I am?”

I nod, sipping my coffee, knowing there’s more coming. There always is with Craig. He pulls out his go-to stats like a magician revealing a rabbit: 50% divorce rate, 70% initiated by wives. To Craig, marriage is less about romance and more about risk management.

“It’s a bad trade,” he says, leaning back like he just shorted your soul. “But I’ve got options.”

Cue Mitch Hedberg: “I bought a $7 pen because I always lose pens and I got sick of not caring.” Craig, however, cares a lot—about not losing.

Option one: “Write up a business agreement,” he says, like he’s pitching a derivative. “Find a smart, attractive woman with a good pedigree. Pay her $150,000 a year for 21 years to have a kid. Add $50,000 a year for child support. It’s marriage without the downside. No alimony, no courts, no sob stories on The View.”

Option two: Go full corporate raider on biology. “I could buy an egg for $50,000,” he says. “Pay a surrogate $150,000 to carry it, and boom—kid’s mine, no strings attached. Then I hire nannies or live-in girlfriends to help raise them. Custody battles? Not in my portfolio.”

He takes a sip of his espresso, waiting for me to applaud his genius or play devil’s advocate. I do neither. I’m still imagining him as a dad, walking into PTA meetings with a trading algorithm instead of a kid’s report card.

“This is the battle of the sexes, man,” Craig says. “And I’m not losing.”

Mitch Hedberg again: “I want to hang a map of the world in my house. Then I’m gonna put pins into all the locations I’ve traveled to. But first I’m gonna have to travel to the top two corners of the map so it won’t fall down.” Craig’s map is more existential, but the pins are still missing.

He leans forward, breaking the silence. “So what do you think? Can anyone punch holes in this plan? Would anyone even take the deal?”

I don’t answer right away. The brunch crowd buzzes around us, oblivious to the existential calculus happening in our corner. Craig’s not asking for advice. He’s asking for validation. And maybe a little hope.

To Craig, the second option is a no-brainer. To me, it’s a hedge against the one thing money can’t control: the messiness of human connection. But here’s the thing about Craig—he’s never been one to buy into chaos. He’ll trade on it, profit from it, even thrive in it. But love? That’s a market he’s still trying to corner.