Living Like a Hollywood Baller with Fighting Broke Style


One night, a Client went to dinner with one of my Boss’s and two production executives at Lucques on Melrose. Both the executives had expense accounts, but the Client covered the tab anyway. In fact, he demanded it.

He told me the next day, without an ounce of brag, “Yeah, it was a nice dinner. Cost me about $300. Plus I left the waitress a $100 tip.”

It was a generous tip. I told him so.

I said, “I aspire to be as generous as you in a few years. I try, and I know I’m not there yet.” And then the Client said something very interesting back to me. The more I thought about it, the more I realized since that this was the secret to being a baller:


How to Live Like a Baller in Hollywood

The Client said, “There were many times I was very poor. Then there were times where I’ve made a few extra bucks. And what I’ve learned: when you have the money, share it. You have to make the decision you’re a baller, and that’s how you roll…’

He didn’t exaggerate about his capacity to share his wealth. I knew from personal experience: he’s the Client who gave me bonus checks for doing my job. I knew he covers most tabs and always leaves a ridiculous tip, even if all he ordered was a coffee. It’s part of his standard operating procedure.

Nor did he exaggerate about his poverty. During his hardest years he lived out of a cardboard box in MacArthur Park, fueled by an alcohol and prescription drug addiction that drove him destitute.

The remnants of his past life are more visible than the new. He wears Hanes and floral print. He drives a Chevy. Toys most of us would classify as necessities he eschews completely: he owns neither a computer nor cell phone.

So it’s not like I want to emulate every aspect of his life. Especially the living-in-the-park parts. And the substance abuse. The generosity part, though, yes, for sure.

I think there’s a cultural element to it, too. Poker great Johnny Chan recalled after playing cards all night, they’d get breakfast the next morning and it was the winner’s honor to treat everyone to the meal.

It’s a privilege to pay for someone else’s meal! 

(It’s when Johnny repeatedly found himself covering the tab, he discovered his penchance for games of skill and chance.)

The Missing Link

This idea, that it’s a privilege to treat others, is the missing link between those we see as generous and those who aren’t.

For some, the privilege is treating themselves to the best that the world has to offer, to display the best toys, to consume the most luscious foods, and wear the finest clothes.

It’s a difference in opinion. I hate reducing the idea to words like “cheap,” “rich,” “stingy” or “frugal,” as they mean something different to everyone, and there’s no consensus. They carry a connotation that makes people defensive.

A Baller Fighting Broke

For the majority of Fighting Broke, I write about cutting costs, saving more money, and the power of long term thinking. It’s amazing what small, consistent habits and compound interest can do in 10 years.

To shed costs, you have to distinguish between the what’s actually important to you, and what others have convinced you (and in turn, what you’ve convinced yourself) is important. Be ruthless when in eliminating the latter. Which sounds easy, except you must do this in the face of immense peer pressure to “act as if.” 

  • Finance a car you can’t buy… to act as if you can afford a luxury vehicle.
  • Pay a $10,000 fee for a membership to SoHo House… to act as if you rub elbows with the socialites.
  • Buy a lavish home with furniture to match… to act as if you’re affluent.

What happens when we stop acting as if what’s important to everyone else, is as important to us? What if we stopped acting and just focused on what really mattered?

I cut back on going out for lunch, limiting it to when I’m eating out with someone else. Eating out, I realized, isn’t important to me. I’d rather bring my own lunch so I can work and read through the hour. What matters is meeting new people, and connecting to them over a meal. And now, because I’m more selective about when I do go out, I know I’ve saved enough to buy my friend’s lunch as well. That makes me feel good.

Same thing with drinks. When I sit down and think about the “act” of going to drinks, what is it about? Is it about me actually drinking for the effects of alcohol? No — if that’s what I wanted, I’ll climb into my cave, vodka bottle in hand, and drink alone. Drinks are about connecting with people, and a good faith way to connect with others is a small token of generosity, like paying for their drink. The connection — not the drinking, not the money, is what’s important.

It’s about consciously making choices where I’m going to spend my money. This is especially true as I’m starting my career, building it from the bottom-up. I don’t spend money on myself so I can spend it with others.

What other unimportant expenditures do I forgo besides networking lunches and drinks to spend money on things that I actually give a shit about?

All of this is done with these goals in mind:

  • Save more money
  • Stay out of the debt that keeps you chained to the Hollywood system
  • When it’s time to be generous, you can do so without having to worry that you’re threatening the above two. 

What’s Important to You?

It’s when you cut out the bullshit spending on things that don’t matter, you’re free to be a baller on the things that do.

I’m curious – what’s the most important thing to you? It can be anything – clothes, shoes, your stamp collection… And what have you cut out in order to be able to buy it, guilt free?


Photo Credit: Montauk Beach

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