Tax-dodging tech bros: should you move to Miami or Austin?

A decision guide for tech founders who are shitting themselves about the tax implications of a potential "exit event"

If you’re a tech bro and there’s a chance your company might sell next year, it’s peak panic season. Knowing when to move to a tax haven is like knowing when to take viagra when you’re a little too high on K at a floor party and vibing with someone who seems remotely interested in you. You aren’t entirely sure you’re going to get laid, but you’ll regret it if you don’t just swallow the pill. The same is true of preemptively moving from highly desirable cities like New York and San Francisco to highly undesirable cities like Miami and Austin. Once you’re able to consistently fabricate at least $10 million in annual recurring revenue (ARR) and your PR company has created a convincing illusion of momentum, you will feel compelled to give up a great quality of life, an inspiring social circle and direct flights to Europe and Asia to dodge a slightly larger tax bill just in case a private equity firm or larger tech company starts feeling sad when one of their competitors buys your far more successful competitor and decides to acquire your company as a FOMO consolation prize.

This guide will help you decide which of the two most common tax prisons suit your “personality.”

To help quantitatively facilitate this high-stakes social-suicide decision, I put together a decision tree, which isn’t actually a decision tree, because making those things takes concentration and design talent, neither of which I have. To figure out where you should move, just add up the numbers associated with each answer. The numbers for Miami are positive, and the numbers for Austin are negative, which I realize is confusing because both cities are negative. 

Miami =   +1

Austin =   -1 

Would people who just met you describe you as “nice”?

Yes: -1

No: +1

How seriously do you take yourself?

Not that seriously: -1

Super fucking seriously: +1

Do you like drugs? 

Yes: 0

No: liar 

What percentage of your photos are Burning Man?

>50%: -1

<50%: +1  

Where would you most like to spend your 182 days of parole each year until you’re wealthy enough to move back to NYC/SF?

Hamptons, Europe and Aspen: +1

Hamptons, Europe and Vail: -1

Which breed of dog do you prefer?

Chihuahua: +1

Black Lab: -1

What kind of house do you prefer as your tax prison cell?

$17m large glass box with tinted windows built on small plot of land that the sea will reclaim in 20 years: +1

Small beige brick ranch built in 1978 purchased by previous owners in 2017 for $350,000, sold to you for $3.5m: -1 

Which kind of car do you prefer?

Porsche 911 Turbo: +1

Highly modified vintage Ford Bronco that costs same as Porsche 911 Turbo: -1

Which kind of boat do you prefer to consume drugs on?

Really big white one, on which you will host sunset cocktails but will never actually drive: +1

Smaller blue one that you will use on a man-made lake the color of an NYC sidewalk puddle in March : -1

What brand of cooler will you buy for your boat?

Igloo: +1

Yeti: -1

What kind of beer will you put in your cooler?

IPA: -1

cocaine: +1

Which sport would you prefer to buy all of the requisite equipment for and never actually pursue?

Stand up paddle boarding: +1

Horseback riding: -1

Which tedious topic of conversation are you most likely to bore people with at a sunset cocktail party?

The therapeutic use of psychedelics: +1

The therapeutic use of psychedelics: -1

What kind of music will you pretend to like at sunset cocktail parties and aggressively defend when your visiting NYC/SF friends make fun of you?

Reggaeton: +1

Country: -1 

Which style of shirt will you wear at sunset cocktails parties and aggressively defend when your visiting NYC/SF friends make fun of you?

Floral short sleeve button down: +1

Slim cut western long sleeve button down: -1

Which kind of VC would you prefer to be lectured by at a sunset cocktail party?

26 year old crypto “VC” who was early in Dogecoin and drives a rented Lambo: +1

62 year old healthcare VC who was early in Pfizer and drives a horse that he bred and birthed with his bare hands: -1

If you are single, which kind of partner do you prefer?

Trashy hot, 12 years younger than you, will bring their own lawyer (BYOL) to prenup negotiation, used to be a personal shopper and now has one thanks to settlement from first marriage to a mid-level member of the cartel: +1

Wholesome hot, closer to your age, has a very expensive horse bred by her (actual) daddy (the healthcare VC), will ask that whatever money you saved through tax avoidance be donated to an animal shelter: -1

Are you polyamorous?

Openly poly: -1

DL poly: +1

If you are married, which kind of divorce do you prefer?

Very bitter, drawn out, expensive, publicized in Miami Herald: +1

Totally amicable (because one of you becomes gay), continue to cohabitate for pets: -1

Do you like tacos? 

Yes: 0

No: stay and pay your taxes

How much is your company likely to sell for?

>$300 million: +1

<$300 million: -1

NOTE: if >$500m, stay in NYC/SF and make tech bros who move to Miami or Austin look poor because they wouldn’t be rich in NYC/SF

Are you pregnant with Elon’s baby? 

Yes: -1

No: +1

If your total is greater than 5, you should move to Miami. 

If your total is less than 0, you should move to Austin. 

If your total is between 0 and 5, you aren’t insufferable enough in either direction to move. Just pay your taxes and have another bump of K.