Wow, Rich People Really Know How to Make Everyone Miserable

Photo: Blasius Erlinger/Getty Images

This week, one Twitter user surfaced the TikTok account of a man named Tom Cruz (no relation to Ted Cruz or Tom Cruise), a real-estate investor and self-described “serial entrepreneur” who apparently keeps multiple spreadsheets to plan vacations with his friends. Now, as a criminal vacation organizer who’s been known to schedule “relaxing pool time” and “showering,” I am in no way opposed to ruining everyone’s fun by attempting to turn our precious days off into a highly regimented grid. But Cruz’s system raised more than a few eyebrows.

The spreadsheets are all organized by income level, with the top 15 earners in one (“Forbes Friends”) and the “Welfare Ten,” with the lowest incomes, in another. Other categories taken into consideration include marital status, willingness to split a private jet, willingness to travel to Third World countries (apparently one of the Welfare Ten is not because he’s had a “bad experience”), and the real kicker: whether they’re a “degenerate gambler.”

At the top of the list, the highest seven earners, who all appear to have unlimited paid time off, apparently make between $1 and $5 million a year — although, notably, whoever created this spreadsheet has observed that one of them may have an “irresponsible” travel budget. At the bottom of the top 15 sits someone named “Broke Bobby,” whose $125K income still places him well above the U.S. median income.

Cruz calls this system “pragmatic” and “motivational,” which are … not exactly the words I’d use to describe it. Aside from, you know, why?, a few other questions remain. First: How many friends does this man have? Do you have upward of 25 acquaintances close enough to provide their income information, let alone that would want to go on vacation with you? I certainly do not.

Another one: What, exactly, does “70% single” mean? Is Chris K.’s relationship open seven out of every ten days? In a given room, is he permitted only to flirt with seven out of every ten women? This one will no doubt keep me up at night.

And finally, one that really eludes me: Who is going on vacation with this guy? Imagine: You, making $92,000 a year and therefore not inclined to gamble, are approached by your friend, who just purchased a Ferrari while he waits for his custom Lamborghini to arrive. He has planned a custom vacation tailored especially for your pitiful earnings. How thoughtful! Do these people just … say yes?

Wow, Rich People Really Know How to Make Everyone Miserable