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Non-qualified stock options: How your NSOs work

Startups and other organizations frequently offer two primary kinds of stock options as part of their compensation packages for employees: Incentive Stock Options (ISOs) and Non-Qualified Stock Options (NSOs). In addition to these, companies may present other forms of equity-based rewards such as Restricted Stock Awards (RSAs) and Restricted Stock Units (RSUs). Each of these comes with its own tax implications as set forth by the Internal Revenue Service (IRS). This guide focuses on the intricacies of NSOs. What You Will Learn: Understanding NSOs Taxation of NSOs How to exercise NSOs What are Non-Qualified Stock Options? Unlike ISOs, which offer tax advantages, Non-Qualified Stock Options (often abbreviated as NSOs or NQSOs) don’t come with preferential tax treatment. Apart from employees, NSOs can also be awarded to freelancers, advisors, and external board members. While ISOs are generally tax-free upon exercise, NSOs will usually incur taxes both when you buy the shares (exercise the options) and when you sell them. With NSOs, you gain the right to purchase a predetermined number of shares at a specific price, commonly referred to as the strike, grant, or exercise price. The company’s 409A valuation or Fair Market Value (FMV) sets this price. If the share’s value rises over time, you stand to profit from the difference (known as the ‘spread’) between the fixed purchase price and the price at which you sell the shares. Tax Implications of NSOs When you exercise NSOs, you’ll owe taxes on the spread, i.e., the difference between the strike price and the current FMV. If you’re an employee, the company will typically withhold the requisite income tax at the time of exercise. As a freelancer or advisor, you’ll need to make tax payments directly to the IRS. For example, if you exercise 100 vested options with a grant price of $1 and the shares are now worth $2, you’ll incur taxes on the $100 gain. Selling Your NSOs After exercising the options, you have the choice of immediately selling the shares or holding them. Selling them right away means you’ll pay ordinary income tax on the spread and avoid capital gains tax. If you sell within a year, you’ll pay short-term capital gains tax on any profits. If you hold for more than a year, you’ll benefit from the lower long-term capital gains tax rate. Qualified Small Business Stock Exclusion If you hold onto NSO-derived stock for at least five years, you might qualify for the Qualified Small Business Stock (QSBS) exclusion, which would allow you to sell the stock without facing federal capital gains taxes, under certain conditions. Tax Summary: Exercising NSOs: Expect to pay ordinary income tax on the spread. Immediate Sale: Ordinary income tax applies on the spread. Selling within a year: Subject to short-term capital gains tax. Selling after one year: Eligible for long-term capital gains tax. Selling after five years: May qualify for QSBS exclusion, potentially owing no federal capital gains tax. When to Exercise NSOs The opportunity to exercise your NSOs generally occurs according to a set vesting schedule. You can exercise them as soon as they vest, or choose not to. Payment options may include cash or a ‘cashless’ exercise, where a portion of your shares covers the exercise cost. If you leave the company, a post-termination exercise period (PTEP) often applies, giving you a limited timeframe to exercise your vested NSOs. Failing to act within this period means losing the opportunity. To optimize your financial outcome, consult a tax advisor before exercising or selling your NSOs. While they can’t forecast your company’s stock performance, they can help you strategize to minimize your tax burden.

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Kevin Taylor

What should I know about Bitcoin?

Let me be clear from the beginning, there is a demand for a stable value, inflation-resistant currency in the world. It’s not Bitcoin.  Bitcoin might be the first through the door, it may revolutionize the zeitgeist ways we discuss the usage of currency and it might be an early aid in getting people around the world out of using their destabilized local currencies. But it will more likely be the myspace of currencies.  Inflation Hedge: Bitcoin can be a store of value  Bullish Bitcoin advocates have routinely promoted the digital coin as a reliable store of value.  They are convinced the digital currency can be a store of value assets like, commodities, or currencies that maintain their value. So many of these advocates see bitcoin as an “inflation hedge.” And while it might be, I think there is a far greater concern that it outpaced any reasonable amount of hedging it was capable of. In 2020 inflation on the CPI was 2.3%, arguing that the buying power of U.S. dollars shrunk by 2.3%, but the bitcoin rose 66%. I would contend that while a small portion of the change was the result of inflation, the other 63.7% was pure speculation. Let’s look at other stores of value, say copper. When the price of copper increases by say 6% in a year, the first 2.3% can reliably be because the buying power of cash deteriorated in comparison to copper over the course of the year.  The 3.7% delta is due to increased demand for copper usually as a result of its utility. Thus, the increase is driven by underlying market functions for copper. I think the same argument should be made for bitcoin, that the first amount it increases in value is the result of inflation and the second is the result of speculation on inflation. The speculation element is almost 29 times higher than the inflation rate in 2020. I think with that ratio of inflation hedging capacity to speculation being so wide it cannot be a reliable replacement for traditional inflation hedges. Let’s then add a more practical element, Bitcoin fever is not the honest result of people hedging their inflation bets. I don’t believe most of them are concerned about the pace of inflation that they can justify a 66% run-up as a concern for the Federal Reserves’ buying rate. It’s more likely the result of seeking a high return on assets. This is then where I am truly concerned about Bitcoin (or any cryptocurrency) being considered a store of value. Let’s then take a look at the utility of Bitcoin. Some of the value of other stores of value is that they have an intrinsic utility. Arguably, they were a reliable “store of value” before they were thought of that way by markets. Since the dawn of commerce, traders have used precious metals and industrial metals to store value. They have a legacy of usefulness. Gold was made into jewelry early, then coinage, then dentistry, and now it’s mission-critical in aerospace and technology. It has always had a drop-dead value because of its innate function. So if you were worried about the governing power that developed a currency, in 700BC or 2021, dropping to zero, the store of value would still have some intrinsic usefulness. I’m not sure the same could be said for bitcoin, because unlike other commodities and precious metals I can’t make a house with it, mold it into utensils, or wear it around my neck. Bitcoins value without its relationship to other currencies is $0. Market Hedge: Bitcoin can hold value when markets fall For this, I think it’s important to look at the behaviors of the people who are buying both the market and the underlying fundamentals of each. I think that it is true, that both the market and Bitcoins are inflation-hedged assets. Only one of these makes sense over time. Additionally, we look at the correlation of the greater market to Bitcoin. In terms of volatility, like March of 2020, we saw equity high volatility in Bitcoin. In times of expansion, we see similar directionality. I think a greater, more lasting argument can be made that Bitcoin’s success and the success of the market are the results of the same underlying causes of liquidity. As we generate more money in the world, the price of assets rises, this shouldn’t be a shock. What does become a point of distinction between the two is that while Bitcoin can arguably “inflate” as long as the de facto Crypto is still Bitcoin. What it cannot do, is provide the investor cash flow in the future. The market however is the representation of ownership over future cash flows. So when markets “sell-off” there is a bottom-rung where the price of future earnings is too appealing and recruits investors back to the marketplace. With no such promise of future cash flows from bitcoin, what becomes the bottom rung? For most commodities, it becomes its intrinsic value, for Bitcoin that is $0.  Fixed Asset: “Bitcoin is a fixed amount and there will never be more” This is kind of an illusion. Yes, there will be a fixed amount of Bitcoins, but not a fixed amount of cryptocurrencies. Each currency type will have its own value, function, and framework. So if in the infinitely expansive ecosystem of “coinage” something comes along that can supplant the “fixed” appeal of bitcoin, and have some other benefit, the appeal of Bitcoin erodes overnight. Say for example a “fixed amount currency”, more granular than bitcoin, or fixed amount and acceptable in Costco whatever the case is, becomes the Bitcoin+ currency of choice.  Then it becomes a question of “How long will people accept my bitcoin?” and then it’s a run for the door trying to not be the last person holding a tulip. The race will become how many Bitcoin+ will I be able to exchange for my Bitcoin. So the argument that it’s “digital gold” is valid until there

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Kevin Taylor

When does a Bear look like a Bull? (Pt. 2)

When will a Bear-Market Rally form a New Bull? The market will turn around, they always do, some would argue that they are built to expand. Below are some of the elements we look for to determine if a market is turning around, or if we are looking at another Bear Rally.  Rallies will get longer in time, and less dramatic  The drama of a bear market is exciting and news outlets love it. The markets and the news gravitate towards those chaotic headlines. This was easily seen when during the last Bull market news outlets ran headlines and talking heads marking the top, declaring market “warnings” and finding economists that would deride the market. It’s exciting and captures eyeballs…the turnaround won’t be all that exciting.  There won’t be a day of major capitulation, followed by a counter move to the upside. It will come with steady, long-term grinds up. It will come with the whole market moving up in a coordinated and cooperative way. Markets with a broad influence from several sectors that grind out small moves over a long time are far more attractive to investors and generate a virtuous cycle.  The Bear Rallies of 2022 so far…   Days Percent Daily % Bear Rally (1) 9 6.1% 0.67% Bear Rally (2) 11 9.9% 0.90% Bear Rally (3) 12 6.2% .51% Bear Rally (4) 41 14.3% .34% Bear Rally (5) ? ? ? The median gain of the largest rallies that have occurred within bear markets is 11.5% over 39 days. Typically, the rallies on the low side of the median, occur early in the bear market, while those that exist on the high side are in the more mature parts of the bear market. Additionally, there are far more rallies below the mean, than above. Meaning that we will see more false rallies that are short and volatile and only a few long-term sustainable rallies that are long with small moves. The longer these rallies get, and the smaller the moves, the more likely an “all clear” can be declared.  There will be broad support   Investment professionals look for certain technical signals to be in place before confirming a reversal is underway. There are several measuring sticks that look for broad support in trading. The advance-decline line, trades above the moving average, and the McClellanOscillator are examples of technical measurements of the breath the market is moving, for how many stocks and how many sectors are participating in the move.  “Breadth thrust” is the term for these signals, and a leading indicator if a market is transitioning from a Bear to a Bull. The duration of the move and the price gains associated with it are also important. The indicators that most reliably confirm that there is a shift into a new bull market are: Flows into equities and out of cash in important ETFs There are “traders” ETFs, and there are “investors” ETFs, and knowing the difference is important. If dollars are flowing into leveraged high volatility trading products it is a signal that the market is trading for a short-term and volatile swing (read a bear rally). If money flows are going into long-term holds that cover the whole of a market in balanced and long-term ways, it’s a signal that the investment appetite is changing to a more long-term outlook and investors are building a new core of their profile. Outsized flows into SPY, QQQ, or VOO are a good sign that the broad market is healthy and investors are willing to hold the whole of the market.  The current market is witnessing the worst first half for stocks and bonds in 50 years, the highest inflation in 40 years, and an endless barrage of bad economic data. So seeing a broad, coordinated shift from cash and cash-like funds, into broad equity will be a good sign in a change from “risk off” to diversified “risk on”. Earrings being “better than expected” at more and more companies There is an entire industry reporting on “beats and misses” on companies’ earnings. While individual stock stories are exciting and reported on the news, the sizes and frequency of misses vs. beats are often overlooked.  Wall Street pros are at odds as to whether we are at an inflection point in the markets. That inflection point will be confirmed when estimates, which are increasingly bleak, are replaced by corporate earnings that are better than expected. This will take several quarters and is a laggard indicator. But is the most reliable measurement to say the companies that make up the market are in a healthy and expansionary space. This seachange in earnings will likely happen 2-3 quarters after the market has “bottomed”, so while not a great trading and timing indicator, it is a very good indicator of changes in the macroenvironment. Company earnings are a more reliable indicator of investment health, this is not a shocking revelation. But the frequency and diversity by which these companies manage inflation pressures, and sell their product to the marketplace is a tide that raises all boats and encourages board participation in rising stock prices.  What past Bear-Markets tell us about future ones A peek at the history of bear markets would suggest that the “naysayers” are on the right side of history, at least for a time. In the 30 different bear markets that have occurred since 1929, the stock market registered an average decline of 29.7%. These downturns lasted have lasted for an average of 341 days. 86% of the bear markets last less than 20 months, and few last longer than one year.   Right now, according to traditional economic interpretations, the U.S. could well be in a recession. We have seen two-quarters of GDP contraction. The Commerce Department reported that gross domestic product shrank by 0.9% in the second quarter of, after contracting 1.6% in the first quarter of this year. That’s it, that is the traditional definition of a recession, and the Bear market has priced

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