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Antiwork

Why TrustFundTimmy Wouldn’t Work at the Factory

HOW THIS FALLS INTO ANTI-WORK: My boss underpaid me, then cheated me out of commissions. That money went to his unmarried, middle-aged kids, none of whom supported themselves, and only one of whom had a real job. TLDR: Timmy didn't like that the factory workers weren't cool. I worked for a factory that was owned by a family I knew growing up. One night the owner's son invites me out to dinner where he tells me: “My dad took me to the beach house over the weekend. We were having a good time when he totally blindsides me and says, why won't you come work at the factory?” I was pretty surprised to hear this. Timmy was more than 10 years out of college and never worked a job on a W-2. The boss would talk about Timmy doing big deals in the entertainment industry. He lived in one of…


HOW THIS FALLS INTO ANTI-WORK: My boss underpaid me, then cheated me out of commissions. That money went to his unmarried, middle-aged kids, none of whom supported themselves, and only one of whom had a real job.

TLDR: Timmy didn't like that the factory workers weren't cool.

I worked for a factory that was owned by a family I knew growing up.

One night the owner's son invites me out to dinner where he tells me:

“My dad took me to the beach house over the weekend. We were having a good time when he totally blindsides me and says, why won't you come work at the factory?

I was pretty surprised to hear this. Timmy was more than 10 years out of college and never worked a job on a W-2. The boss would talk about Timmy doing big deals in the entertainment industry. He lived in one of the big cities for entertainment, supposedly hung out with celebrities, went to movie premiers, and was photographed by the paparazzi (no photos are online).

Timmy went on: “He was really pushing, so I told him – “

“You bought a house,” I interrupted. “Why would he ask now?”

“Well, it was time to have the talk anyway, because I knew it was coming. So I told him, the people there are all old, and don't have any interests. None of them are doing anything. I think he accepted it. I mean, he knows I'm right.”

“You have a career,” I added, “in entertainment.”

After some hesitation, he said, “yeah.”

That hesitation made me curious, so I kept my ears open for a bit. Turns out:

  • Timmy's house? His dad bought it, and Timmy made money with a roommate who paid rent
  • Timmy's success? His dad bought it. A music act that he once managed had a Top 200 album. My god, we'd always hear about this fucking group, and what a genius Timmy was. Well, while cleaning out the supply closet, I found hundreds of CDs
  • He had income from a trust fund, but his mom and dad paid for his:
    • phone
    • health insurance
    • tax return filing
    • flights home

I was sad for Timmy until I brought in a huge customer for the factory (like, the literal biggest possible customer you can get). Anticipating the commissions, I opened a college fund for my daughter and started the process of buying a house.

After a couple orders, I'd inquired about how commission payments came in, and the boss said that he wasn't associating this customer to any salesperson. I let him know that I very clearly brought in the account, and it took me 2 years to do so.

The boss cancelled doing business with them, and my guess was the same reason he fired a guy who'd previously brought in a huge account – he would rather lose a person than pay them.

After this, I drew up an outline of all the improvements the company needed to make, which was part of a class I was taking. The boss got really mad and didn't come to the office for weeks.

Timmy's in town and wants to meet.

“What do you think is my father's greatest weakness?” he asks.

“He doesn't make decisions,” I said, without hesitation.

Timmy rants about his dad, and how bad a businessman he is. I let him vent, and we had an otherwise nice lunch.

The next day I get an email from Timmy saying, “I didn't appreciate everything you said about my father yesterday. Have a little respect. I know things aren't working out like you wanted, but sometimes that's how business is.”

Timmy, in writing, is doing damage control.

He's afraid his words might make the golden goose infertile.

In the end, I knew I could never make any money there. In order to pay my mortgage more comfortably, I got a remote job that I did from the office. I then finished my MBA, and moved on.

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