Date Night with The Wolf of Wall Street
The Wolf of Wall Street was in town and we turned it into a date night
“The Wolf is coming to town!” I shrieked to my husband as I perused Books & Books’ jammed-packed events calendar. From Leonardo Dicaprio’s charismatic portrayal on the big screen to the underground 2015 song that carries his name, Jordan Belfort is an American icon — whether for the right or wrong reasons.
The former stockbroker turned financial criminal turned best-selling author was making a stop to promote his latest book, “The Wolf of Investing: My Insider’s Playbook for Making a Fortune on Wall Street.”
You might be thinking, “A date night about the stock market? How romantic!” But to say we were both geeked to meet the Wolf is an understatement. My fascination with Jordan stems from his bigger than life persona and entrepreneurship advice that often comes up on my TikTok “For You” page. My husband’s motivation was more traditional, considering he’s spent the last five years trading stock options.

We started our evening out with a glitzy happy hour in Morton’s Steakhouse. Bar 1221 serves “power hour” drinks and bites, which seemed like a fitting pregame to meeting Mr. Belfort.
For $10 each, we enjoyed two very different cocktails: mine the Palm Beacher, a light pineapple-infused vodka, and my husband’s the tangy Mezcalrita, made with Dos Hombres Mezcal, lime, and hot honey. We raised our glasses to learning a thing or two from the Wall Street legend.
The bookstore was packed with eager readers, finance hopefuls, and the occasional movie fanatic, all anxiously waiting for the VIP guest. As a black SUV pulled onto Aragon Avenue, heads turned to watch the Wolf step out.
Despite more than 100 attendees who reserved their copy ahead of the meet-and-greet, the line moved along. Everyone got in a good handshake, iconic selfie, and their own signed dedication page. One young finance professional in his 20s mustered up the courage to ask Jordan his advice for someone like him, working at Fidelity Investments in the Gables. The Wolf ’s wise words? “Just keep dialing.”

After signing my copy with “To Natalia” followed by what he described as a doctor’s illegible signature, Jordan gave us a quick interview, telling us how it felt to be promoting his book in the Gables. “I’ve been to many bookstores, of a lot of sizes, but this is the coolest bookstore ever,” said Jordan, sitting in front of the bookstore’s Lego replica.
“Number one [advice] is, think big,” he told us. “A lot of people when they’re trying to say, ‘What do I want my life to look like in five years?’ don’t think big enough… Make sure your vision for your future is grand and turns you on.” Watch the full interview on our Instagram.

The Wolf didn’t invite us to join him afterwards at Carbone, but following a brief walk to Giralda Plaza we managed to satisfy our Italian cravings, minus the four-dollar signs, at Craft. In deciding what appetizer to order, I asked myself, “What would Jordan do?” and my gut responded: go with the saucy meatballs. Nothing like dipping the toasted sourdough slices into the rich tomato marinade.
Their Neapolitan pizza menu is meant to satisfy diverse palates, from the classic Margherita to the Picante Dorito-infused pie. A good drizzle of balsamic glaze made my avocado and cherry tomato pie the best! We sipped on some refreshingly sweet sangrias as we turned the pages of the Wolf ’s investing playbook, lured in by the idea of making our own fortune.
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