How will your executor handle a Bitcoin winter (or crash) like the one we’re living through now? We’ll compare a few likely scenarios depending on who you’ve chosen as your executor.

But first, a few assumptions:

1. You’re a “maxi” (a Bitcoin maximalist – someone who really values Bitcoin in and of itself, and not just its conversion to dollars);
2. You want your heirs to inherit the actual Bitcoin you’ve accumulated, not just the fiat dollar value on your date of death; and
3. You believe Bitcoin’s value in dollars will probably be very volatile for several more years. You understand that even if it’s “down” during your probate, you want your executor to hang on to it.

So here are a few scenarios:

Professional executor, but doesn’t “get” Bitcoin

There are many attorneys and banks who are savvy in executorship and probate. In fact, banks have whole departments with trust officers that handle this. Once you find these experienced folks, do they have knowledge of Bitcoin? Maybe, but they probably have knowledge of crypto in general.

Bitcoin maximalists consider themselves separate from the rest of the crypto universe. If your professional executor has only a light understanding of crypto in general, they will associate Bitcoin with the current crypto crash. During a crash, can they withstand psychological pressure to sell? Probably not. That’s the most likely outcome with a professional executor that doesn’t understand Bitcoin like you do.

Maxi amateur executor

Say you chose your buddy who is a fellow maxi but has never been an executor before. He probably has similar values as you and wants to hold on for dear life (“HODL”). But, he has very little knowledge of the probate process or experience being executor.

If Bitcoin is going through a winter cycle during probate, the heirs may demand that he sell the Bitcoin so they can get their inheritance in cash. Can this amateur executor withstand threats of lawsuits, accusations of breach of fiduciary duty, and sob stories from heirs? Between dealing with that and also trying to HODL, it’s going to be a lot of pressure. If the executor doesn’t understand how to defend himself, he might be convicted enough to protect his own stack of Bitcoin. But he might give in to pressure from the heirs and sell their UTXOs so they leave him alone.

Understandably, you want your executor to be experienced with Bitcoin, but you also have to weigh whether the executor can withstand the pressure.

Professional Bitcoin Executor

Your best bet is to find a professional Bitcoin executor. Investor Michael Burry, from the movie and book Big Short, ran a fund holding money for other people. He shorted the real estate market right before the crash of 2008.

While the real estate market was doing well right before the crash, his positions were losing a ton of money. His investors wanted their money back and threatened to sue him. Burry kept saying no and told them to trust him. He even took technical steps to keep the investors’ money in place to prevent investors from withdrawing.

In the end, the recession happened, and all of those shorts exploded, allowing his investors to make 400 times their money. At the end of the movie, Burry sends out a one-liner email: “You’re welcome.”

In our estate scenarios of a Bitcoin winter, you need someone like Burry who is both convicted AND knowledgeable. You need someone who can carry out your wishes and do a probate-version of a side pocket to make sure he withstands the pressure and delivers the Bitcoin to your heirs.

I hope to fill a similar role, and hope others will, too. I have the experience as a professional executor, and I am beginning to see the light of Bitcoin values. While this topic is very specific, you can still learn about hiring a professional executor in my book, “How to Hire an Executor.”

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