"$72 Boxer Briefs": 2 Hollywood Executives Reveal How They Spend Their Money

6:30 AM 10/14/2019

by Edited by Natalie Jarvey

Execs — with two very different wallets — anonymously share the secrets of where their paychecks go.

Executives Spend Their Money -plane - H 2019
SFIO CRACHO - stock.adobe.com

  • The Jet-Setting Entrepreneur

    Occupation: Startup Founder

    Salary: $0

    Location: L.A., N.Y., S.F. and Asia 

    Age: 32

    DAY 1

    3 A.M. I'm jet-lagged in Jakarta and I open the dating apps that I installed for the first time a month ago. They're all trash. Commitment is scarce these days, just like eye contact. $249 per month

    5 A.M. I succumb to jet lag and head to the hotel gym, which makes no sense since it's the opposite of sleep. Instead of working out, I schedule a two-hour afternoon massage. $250

    6:15 A.M. I turn on Spotify and sing along to Brian McKnight's "Anytime" in the shower. I'm tone-deaf but compensate with enthusiasm. $9.99 per month

    10 A.M. What sane human refuses chocolate chip pancakes and seafood crackers? The waitress asks if I'm going to finish it all, and I point to my belly. She asks where I'm from. America, obviously. $80

    11:05 A.M. I email a few of my portfolio companies. One just got acquired by Facebook, so everyone else — by default — is now behind. I don't pay myself a salary but earn enough through these investments and board and advisory fees to pay for my lifestyle. $310,000

    4 P.M. I tip my masseuse 20 percent in a country that doesn't tip. $50

    4:15 P.M. I won't have time to do laundry next week, so I buy a bundle pack of Rhone boxer briefs online. $72

    5 P.M. I meet the apparel manufacturer who's producing a line for one of the franchises that my company will debut next year. $2,000 for samples

    7 P.M. This Four Seasons boasts one of the best pasta restaurants in the world. I've been investing in savoring the entire 11-dish pasta menu over the past three days, but tonight I order repeats of a porcini straccetti and tagliatelle Bolognese. $82

    DAY 1 TOTAL: $2,792.99

    DAY 2

    4 A.M. I pay the mortgage and HOA fees on my two condos with my new Facebook money before flying back to L.A. $6,550

    7 A.M. I'm flying first class, so I don't feel bad about keeping United's earplugs, ChapStick and socks. I order a glass of champagne with a faux British accent that only comes out on planes and in restaurants. $0 (but $5,428 for the round-trip flight)

    6 P.M. It's evening when I arrive in L.A., where I'll spend time with my mother. My father died when I was a teenager, so seeing her weekly is a thing. She starts being Mom and laments over trivialities. I leave the dinner she made. $0

    6:05 P.M. I call my therapist. She should be hundreds an hour, but I get an insane discount. $40 per hour

    6:30 P.M. My executive coach calls for our weekly session. I give him nothing but happy updates; I don't need another lecture for things I can fix. $350

    7 P.M. I book a weeklong solo vacation — my first in at least two years — near a beach. $2,800

    DAY 2 TOTAL: $9,740

    DAY 3

    4:40 A.M. I scribble an "I love you" note on a Post-it for my mom to read and Uber to the airport. $30

    12 P.M. I'm flying to Atlanta for a friend's wedding and I need a snack. Quest Bar time! $3

    3:10 P.M. After I land, I wait five long minutes for the smoothie worker to come before mistaking a Popeye's worker on his break for said smoothie person. Eight chicken strips it is. $12.50

    3:25 P.M. My Uber gets lost so I absorb the $5 cancellation fee and then call another ride. $49

    4:25 P.M. I forgot a wedding gift! The couple's website has no registry, and the list I Google of top gifts doesn't include anything memorable, so I get them nothing. $0

    10 P.M. My buddies ask where I'm at and I lie that my flight was delayed. They'll see me at the wedding tomorrow. I go online and order flowers (birds-of-paradise) for my mother because I feel bad. I'm just disappointed in who I've become and think it'll buy time. $82 with shipping

    DAY 3 TOTAL: $176.50

  • The Agency Up-And-Comer

    Occupation: Business Development Exec 

    Salary: $60,000

    Location: Los Angeles

    Age: 28

    DAY 1

    8 A.M. I wake up and drive to work, where I drink the mediocre, free communal coffee. $0

    12 P.M. My company subsidizes half of the lunch delivered to the office. Today it's Gracias Madre. It's a stupid-cheap deal. Even if I don't eat the meal for lunch, I still order it and save it for dinner. Where else in this town can you get a full meal at this price? $8

    7:30 P.M. I take two clients to dinner and drinks at Mama Shelter. Thankfully I get to expense the meal. $139

    9 P.M. Why not drive to Corbin Bowl in Tarzana to go bowling with some old friends on a random Thursday night? $39

    DAY 1 TOTAL: $186

    DAY 2

    12 P.M. I forgot to order lunch in time so I go to the food trucks instead. I buy a pulled pork sandwich and fries from A Taste of Soul. $15

    7 P.M. It's Friday, so I'm going out tonight. My friends get a bunch of food from Trader Joe's and invite me to eat at their place in West Hollywood before we start our night. I Venmo them for my portion of the meal. $20

    9 P.M. We meet up with another group and head to Jones on Santa Monica Boulevard. They're feeling generous and buy drinks for the whole party, cutting down my final bill. $22

    10:30 P.M. Our next stop is Bar Lubitsch just down the street. Thankfully I'm still with generous people offering to buy drinks. $0

    12 A.M. Harlowe is never a good idea, but I'm with a few people who have never been and there's surprisingly no line. One of our friends loses her wallet and now I'm feeling generous. Drinks are purchased. Financial mistakes are made. $83

    DAY 2 TOTAL: $140

    DAY 3

    11 A.M. Everything hurts, but it was worth it. I stop at Corner Bakery for a breakfast torta. $22

    3 P.M. I meet some friends to play flag football in Venice and the team decides to go out for a drink (or three) afterward at The Garage in Culver City. $32

    7 P.M. I head downtown to the new Alamo Drafthouse to see Ad Astra (aka Daddy Issues in Space). Tickets + food + booze = one expensive-ass movie night. $43

    10:30 P.M. I meet up with some friends at The Friend in Silver Lake. I was responsible, Mom, I promise. $30

    DAY 3 TOTAL: $127