One of the main reasons that investors — even savvy ones — give for failing to avail themselves of the many benefits the Deferred Sales Trust (DST) offers when selling a highly appreciated asset is that they fear the up-front legal fee they will pay to establish their own DST is too substantial to be worth it. However, is this really true? Let’s use the following case study to show how paying the DST legal fee compares to paying the costs inherent in foregoing its unique benefits.
Back in 1989, a movie entitled “Bill & Ted’s Excellent Adventure” became the hit comedy of the year. Unfortunately, its two main characters, while funny, gave no indication of being able to think. Instead, they relied on chance to solve their problems.
In a previous post, we explained how the Deferred Sales Trust (DST) can benefit you if you live in a state, such as California, that imposes a state income tax. But what if you are fortunate enough to live in a state with no state income tax? How does the DST benefit you then? Read on to discover two ways in which the DST can shield you from substantial capital gains taxes when you sell a highly appreciated asset. For purposes of these case studies, assume you live in Florida, one of the states that imposes no state income tax, and therefore no state capital gains tax.
If you’re a successful long-time investor, or someone who has made good use of your stock options, you may well find yourself in the position of holding one or more chunks of highly concentrated stock. On the one hand, this disproportionate wealth allocation puts you at substantial risk. On the other hand, selling this highly appreciated stock can cause a capital gains nightmare. What to do?
If you’re an investor with a high tolerance for risk, you likely have invested in one or more digital currencies, i.e., cryptocurrencies, in the past decade or so. Bitcoin, the granddaddy of them all, only appeared in 2008. Today, however, you have over 6,700 different publicly traded cryptocurrencies to choose from. Their total value, as of Feb 18, 2021, was more than $1.6 trillion. On that date, Bitcoin alone was worth over $969.6 billion.