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Mental Models

Fat Tony

Fat Tony is a character embodying practical, street-smart thinking that relies on experiential knowledge and skepticism of theoretical models, often used to contrast with nerdy, academic reasoning.

THE IDEA

FAT TONY

“Fat Tony” is one of Nero’s friends who irritates Yevgenia Krasnova beyond measure. We should perhaps more thoughtfully style him “Horizontally-challenged Tony,” since he is not as objectively overweight as his nickname indicates; it is just that his body shape makes whatever he wears seem ill-fitted. He wears only tailored suits, many of them cut for him in Rome, but they look as if he bought them from a Web catalog. He has thick hands, hairy fingers, wears a gold wrist chain, and reeks of licorice candies that he devours in industrial quantities as a substitute for an old smoking habit. He doesn’t usually mind people calling him Fat Tony, but he much prefers to be called just Tony. Nero calls him, more politely, “Brooklyn Tony,” because of his accent and his Brooklyn way of thinking, though Tony is one of the prosperous Brooklyn people who moved to New Jersey twenty years ago.

Tony is a successful nonnerd with a happy disposition. He leads a gregarious existence. His sole visible problem seems to be his weight and the corresponding nagging by his family, remote cousins, and friends, who keep warning him about that premature heart attack. Nothing seems to work; Tony often goes to a fat farm in Arizona to not eat, lose a few pounds, then gain almost all of them back in his first-class seat on the flight back. It is remarkable how his self-control and personal discipline, otherwise admirable, fail to apply to his waistline.

He started as a clerk in the back office of a New York bank in the early 1980s, in the letter-of-credit department. He pushed papers and did some grunt work. Later he grew into giving small business loans and figured out the game of how you can get financing from the monster banks, how their bureaucracies operate, and what they like to see on paper. All the while an employee, he started acquiring property in bankruptcy proceedings, buying it from financial institutions. His big insight is that bank employees who sell you a house that’s not theirs just don’t care as much as the owners; Tony knew very rapidly how to talk to them and maneuver. Later, he also learned to buy and sell gas stations with money borrowed from small neighborhood bankers.

Tony has this remarkable habit of trying to make a buck effortlessly, just for entertainment, without straining, without office work, without meeting, just by melding his deals into his private life. Tony’s motto is “Finding who the sucker is.” Obviously, they are often the banks: “The clerks don’t care about nothing.” Finding these suckers is second nature to him. If you took walks around the block with Tony you would feel considerably more informed about the texture of the world just “tawking” to him.

Tony is remarkably gifted at getting unlisted phone numbers, first-class seats on airlines for no additional money, or your car in a garage that is officially full, either through connections or his forceful charm.

When to use it

  • Negotiating a deal with a large bureaucracy by understanding the incentives of individual employees.

  • Getting a reservation at a fully booked restaurant through personal connections and charm.

  • Evaluating investment opportunities based on practical knowledge of the market rather than complex financial models.

  • Solving a problem by identifying the 'sucker' (person or system with misaligned incentives) and exploiting that weakness.

FROM THEORY TO EVERYDAY LIFE

In practice

01

Getting a first-class seat without extra cost

Fat Tony uses his connections and forceful charm to secure first-class seats on airlines for no additional money, bypassing official procedures.

02

Buying property from banks with an insider insight

Tony realized that bank employees selling foreclosed properties don't care as much as owners, so he could easily maneuver and get favorable deals.

✳

A MOMENT TO REFLECT

Put it to work.

  1. How can you apply Fat Tony's skepticism of theoretical models in your own decision-making?

  2. Think of a situation where street smarts outperform book smarts. How would Fat Tony approach it?

  3. What are the risks of relying solely on practical experience without theory?

Connected ideas

Another lens can bring the same problem into focus.

Often confused with

CONTINUE THE CONVERSATION

Source texts

  • The Black Swan The Impact of the Highly Improbable With a new section On Robustness and Fragility (Nassim Nicholas Taleb)
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