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@ Dug
2025-05-23 15:26:17While I’m going to stand by what I said in my previous piece, minimise capital gains payments, don’t fund the government, get a loan against your bitcoin, but the wheels in my left curve brain have continued to turn, well that, and a few more of my 40PW insights. I mentioned about paying attention to the risks involved in terms of borrowing against your bitcoin, and hopefully ending up paying less in bitcoin at the end of the loan, even if you ultimately sold bitcoin to pay off the loan. However, the idea of losing control of the bitcoin I have spent a good deal of time and effort accumulating being out of my control has led me to reconsider. I also realised I didn’t fully flesh out some other topics that I think are relevant, not least time preference, specifically in relation to what you’re buying. The idea of realising a lump some of capital to live your dreams, buy a house or a cool car may be important, but it may be worth taking a step back and looking at what you’re purchasing. Are you only purchasing those things because you had been able to get this new money “tax free”? If that is the case, and the fiat is burning a hold in your pocket, maybe you’ve just found yourself with the same fiat brained mentality you have been working so hard to escape from while you have sacrificed and saved to stack sats.
While it may no longer be necessary to ask yourself whether a particular product or service is worth selling your bitcoin for because you’ve taken out a loan, it may still be worth asking yourself whether a particular loan fuelled purchase is worth forfeiting control of your keys for? Unlike the foolish 18 year-old, released into a world with their newly preapproved credit card, you need to take a moment and ask yourself:
Is the risk worth it?
Is the purchase worth it?
But also take a moment to consider a number of other things, are there fiat options?
Where in the cycle might you be?
Or if I’m thinking carefully about this, will whatever I’m buying hold its value (experiences may be more difficult to run the numbers on)?
The reason for asking these things, is that if you still have a foot in the fiat world, dealing with a fiat bank account, fiat institutions may still be very willing to provide you with a loan at a lower rate than a bitcoin backed loan. Particularly if you’re planning on using that money to buy a house; if you can qualify for a mortgage, get a mortgage, but if you need cash for a deposit, maybe that is where the bitcoin backed loan may come in. Then, it may be worth thinking about where are you in the bitcoin cycle? No one can answer this, but with the historic data we have, it appears logical that after some type of run up, prices may retrace (Dan Held’s supercycle withstanding).
Matteo Pellegrini with Daniel Prince provided a new perspective on this for me. Rather the riding the bull market gains all the way through to the bear market bottom, what happens if I chose to buy an asset that didn’t lose quite as much fiat value as bitcoin, for example, a Swiss Watch, or a tasteful, more mature sports car? If that was the purchase of choice, they suggested that you could enjoy the car, “the experience” for a year or two, then realise the four door estate was likely always the better option, sell it and be able to buy back as many, if not slightly more bitcoin that you originally sold (not financial, classic car or price prediction advice, I’m not accredited to advise pretty much anything). Having said that, it is a scenario I think worth thinking about when the bitcoin denominated dream car begins to make financial sense.
Then, as we begin to look forward to the near inevitable bear market (they are good for both stacking and grinding), if we’ve decided to take out a loan rather than sell, we then may ultimately need to increase our collateral to maintain loan to value requirements, as well as sell more bitcoin to cover repayments (if that’s the route we’re taking). This then moves us back into the domain of saying, well in actual fact we should just sell our bitcoin when we can get most dollar for it (or the coolest car), with a little extra to cover future taxes, it is probably better to sell near a top than a bottom. The balance between these two rather extreme positions could be to take out a fiat loan to buy the item and maybe sell sufficient bitcoin so you’re able to cover the loan for a period of time (less taxable events to keep track of and also deals with future uncertainty of bitcoin price). In this case, if the loan timeframe is longer than the amount of loan your sale can cover, by the time you need to sell anymore, the price should have recovered from a cycle bottom.
In this scenario, apart from the smaller portion of bitcoin you have had to sell, the majority of your stack can remain in cold storage, the loan you took out will be unsecured (particularly against your bitcoin), but even if it isn’t, the value of what you purchase maintains its value, you can in theory exit the loan at any point by selling the luxury item. Then within this scenario, if you had sold near a top, realised the car gave you a bad back or made you realise you staying humble is more important, sold it, paid off the loan, there may even be a chance you could buy back more bitcoin with the money you had left over from selling your bitcoin to fund the loan.
I have no idea of this could actually work, but to be honest, I’m looking forward to trying it out in the next 6-12 months, although I may keep my daily driver outside of my bitcoin strategy (kids still need a taxi service). Having said that, I think there are some important points to consider in addition to not paying capital gains tax (legally), as well as the opportunities of bitcoin loans. They are still very young products and to quote every trad-fi news outlet, “bitcoin is still a volatile asset”, these thought experiments are still worth working through. To push back on the Uber fiat journalist, Katie Martin, “Bitcoin has no obvious use case”, it does, it can be a store of value to hold or sell, it can be liquid and flexible collateral, but also an asset that moves independently of other assets to balance against fiat liabilities. The idea of being able to release some capital, enjoy the benefits of the capital for a period, before returning that capital to store value feels like a compelling one.
The important thing to remember is that there are a variety of options, whether selling for cash, taking out a bitcoin backed loan, taking out a fiat loan or some combination of each. Saying that, what I would think remains an important question to ask irrespective of the option you go for:
Is what I’m planning on buying, worth selling bitcoin for?
If it cannot pass this first question, maybe it isn’t worth purchasing to start with.