Jell-O Shots

MacBook Pro + Bank Account = PFIC

The Passive Foreign Investment Corporation and Controlled Foreign Corporation rules are the government’s countermeasures against a logical tax strategy–tax deferral.

If your business operates through a foreign corporation … you probably have a latent Passive Foreign Investment Corporation on your hands, or (“less bad”) you probably have a Controlled Foreign Corporation.

The Buckets and Pipes Theory of Tax Planning

Saturday morning in Singapore I will be talking to about 30 entrepreneurs about tax stuff – a bit for themselves, but mostly about their businesses. And that means talking about cross-border tax strategies. “Can I do what Apple does?”

The answer is yes. It’s just not cost-effective until you are operating at scale. For younger companies, the better strategy is to optimize for simplicity. Spend less money on tax brains and pay a bit more in tax. Stay away from the shiny.

Simplicity will make your business nimble, and your time and attention will be directed toward what really matters: creating customers. An entrepreneur’s time and attention is worth far more than taxes saved.

You don’t get wealthy by paying less tax. You get wealthy by creating customers. Look at Apple. Of course Apple is saving tax with clever international tax strategies. But first, painfully and over a long time, they created customers.

Singapore for a Weekend Mastermind

I’m headed to a weekend mastermind group sponsored by Dynamite Circle (I am a member), which is a service provided by Ian and Dan of Tropical MBA.

It’s worth your while reading the TMBA blog and listening to the podcast. Even if you do not fit the “location independent lifestyle” or “digital nomad” profile, there are useful things to learn.

Dan and Ian have done something impressive. They transformed themselves from from two random guys standing around in a parking lot in North San Diego County to the owners of very real and profitable businesses. The best part? These are businesses that they can operate from anywhere on the planet that they want to be (Ian = Austin and Dan = Philippines right now).

Attending the mastermind will be a group of 30 entrepreneurs who have reached a certain level of success.

I’m showing up. I have something to share, and something to learn.

Wherein I Violate the First Rule of Fight Club

Let’s imagine a future risk. Five years from now you will be sued. Extremely generic business litigation. Nothing special, except if you lose the lawsuit your company will be wiped out. High stakes, normal risk.

You will be considerably less stressed as you go through the lawsuit if you know that a few million dollars sits in a bunker, safe, waiting for you after the dust has settled – even if you lose the lawsuit.

How do you go from cocktail party conversation to done? Today I am going to cover the first hurdle. You can’t move forward until you solve this hurdle.


This is part of the Brains Across Borders series – where I talk about tax problems that pop up when the person doing the work is in one country, and the person getting the work done is in another country. And one of those countries is the United States.

This episode looks at one of the burdens on U.S. employers who hire foreign freelancers, and the interesting problem of how you prove that you don’t have to do anything. It’s stressful to be fairly sure you don’t have to do something, but then that little voice in the back of your head keeps second-guessing you…

How Digital Nomads Can Avoid Paying Social Security Tax

This week’s episode is about Social Security tax and self-employment tax, and it tells U.S. citizens and green card holders living and working outside the United States how to not pay those taxes.

Hacker News and Dynamite Circle people (I participate at both places and get frequent tax-related emails from people active in both of them, so this week’s episode is for you) understand that there are good reasons to form a corporation outside the United States in order to do business. Local laws, banking, and visa considerations are three good reasons. There are a ton of dumb reasons, too.

Consider the following scenario, which is useful for a U.S. person living and working abroad as a freelancer, independent contractor, or self-employed person. You may be a digital nomad, perhaps. But this idea will work for any self-employed person or business owner abroad…

Jell-O Shot Mailing List Purged

500 People–Goodbye I purged about 500 names off the Jell-O Shots email list last night: people who had not opened an email from me in a while — namely, in the last 14 editions they had opened the email once or never. I don’t want to annoy anyone with emails they do not want. If […]

Jell-O Shot 25 – The “I’m A People Person” Edition

This is Jell-O Shot 25 – The “I’m A People Person” Edition. It went out yesterday to the fine people on the mailing list. You should be on that list, too. Go to the bottom of this web page and fill in your email address. You can unsubscribe at any time. TL;DR Events. We have […]

Jello Shot Number 2

Jello Shot Number 2. (Shameless promotion: subscribe to my email newsletter.  There’s a place in the sidebar of this blog where you can sign up.) Just finished Just finished a private mortgage project with a nonresident lender. U.S. partnership bought commercial real estate. Thought you should know how these work. The good stuff The borrower […]