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Thinking about taxes proactively allows you to structure your investments and financial decisions to minimize your obligations and maximize long-term returns. This is the difference between reacting to a tax bill and strategically managing your financial future. Understanding Your Taxable Events For most investors, selling an asset for a profit is a taxable event. While this is a major component, it's not the full picture. A taxable event is any action that triggers a tax liability. This can include receiving dividends from stocks, earning interest from bonds, or even exercising certain types of employee stock options. Each of these events can add to your taxable income for the year. Forgetting to account for them can lead to an unpleasant surprise at tax time. A key part of modern tax planning is clearly understanding how your portfolio generates taxable income throughout the year, not just when you decide to sell. The Role of Stock Options in Your Tax Strategy Employee stock options can be a fantastic way to build wealth, but they also add a unique layer of tax complexity. Incentive Stock Options (ISOs) are particularly noteworthy. While they offer certain tax advantages, exercising them can trigger the Alternative Minimum Tax (AMT). This separate tax system ensures high-income individuals pay a minimum amount of tax. Exercising a large number of options might seem like a great move, but it can lead to a surprisingly large AMT bill if you're not careful. Proper planning around when and how many options to exercise is crucial to avoid an unexpected and substantial liability that could otherwise diminish your gains. Strategies for Managing Capital Gains Once you understand your taxable events, you can start using strategies to manage them effectively. One of the most common and powerful techniques is tax-loss harvesting. This involves selling investments at a loss to offset gains from profitable investments. This can reduce your overall capital gains tax and, in some cases, even allow you to deduct losses against your ordinary income. Another fundamental concept is being mindful of holding periods. Investments held for more than a year are typically taxed at the lower long-term capital gains rate. Those held for a year or less are taxed at your higher ordinary income tax rate. Simply being patient and holding a winning investment for a few more months can significantly impact your after-tax return. Leveraging Tax-Advantaged Accounts One of the most straightforward ways to manage your tax liability is to make full use of tax-advantaged retirement accounts like a 401(k) or an Individual Retirement Account (IRA). Contributions to traditional 401(k)s and IRAs are often tax-deductible, lowering your taxable income for the current year. The investments then grow tax-deferred until you withdraw them in retirement. Roth versions of these accounts work differently: you contribute with after-tax dollars, but your qualified withdrawals in retirement are completely tax-free. A combination of these accounts can give you flexibility in managing your tax burden today and in the future. Prioritizing these accounts for long-term growth is a cornerstone of sound financial and tax planning. Proactive Planning vs. Reactive Filing Ultimately, optimizing your portfolio's growth through tax management comes down to a simple mindset shift. Instead of seeing tax filing as an annual chore where you report what already happened, view tax planning as an ongoing strategic process. This means considering the tax implications of every investment decision you make throughout the year. Are you about to sell a stock? Check the holding period. Are you receiving a large cash bonus? Consider how much to put toward a tax-advantaged account. This proactive approach ensures you make decisions that align with your long-term financial goals, turning tax management from a liability into a powerful tool for wealth creation. Effective tax planning is not an afterthought. It's an integral part of a successful investment strategy. Understanding how taxes affect your returns and using the right strategies can significantly improve your ability to build wealth over the long run. This is a contributed post.

Opening Process The opening rotation process for equity options traded during GTH will follow the existing RTH opening process for multi-list options with minimal modifications. A class will begin the GTH opening rotation upon receipt of the first round-lot print in the underlying from any exchange and observation of a two-sided bid/ask in the underlying from any exchange following the start of the GTH session (7:30 a.m. ET). For more information regarding the equity options opening process, see the U.S. Options Opening Process. Risk Management If a firm has existing Default Risk Management rules, those will automatically apply to both the GTH and Curb trading sessions. Alternatively, firms may choose to upload new rules for the GTH and Curb sessions. In order to have a new GTH or Default risk rule apply to the new multi-list GTH trading session, rules must be uploaded prior to 7:00 a.m. ET. Risk rules specified as Default or GTH and uploaded between 8:15 p.m. and 9:00 a.m. ET may optionally be applied immediately via the Customer Web Portal Risk Management Application. Firms cannot use the Secure Web API to make new rules immediately effective. In order to have any updated or new Curb risk rules apply to the multi-list Curb trading session, rules must be uploaded prior to 3:40 p.m. ET. The scheduled system risk reload times will be adjusted. Risk reloads will be scheduled to occur at 2:35 a.m., 7:05 a.m., 9:05 a.m., and 3:45 p.m. ET. In addition, the scheduled risk reload behavior will change. Scheduled reloads will only reset active risk counters for rules that have been changed. The existing Pre-Open/GTH Session exchange default fat-finger limits will apply to the equity options products eligible to trade in GTH. For more information, see the Cboe Titanium U.S. Options Risk Management Specification. Membership and Eligibility Trading Permit Holders (TPHs) must be authorized for GTH trading at the OCC and Cboe. Such authorization will allow GTH trading of equity options and Cboe proprietary index options. Thus, TPHs that are already authorized for GTH trading do not need any further authorization to trade equity options during the GTH session. No additional action is needed to participate in Curb trading. Order Handling and Market Functionality To ensure system readiness, please note the following: The existing SessionEligibility (FIX Tag 22017) will be used to designate session eligibility. GTC Orders carried over from prior sessions will retain their session eligibility. NBBO protection and routing functionality will apply during both GTH and Curb sessions. Quoting and trading activity will be sent over existing OPRA RTH channels. Quoting Obligations Quoting obligations for Designated Primary Market Makers (DPMs) will apply collectively across all classes and sessions for the DPM.* Quoting obligations for non-DPM Market Makers will apply collectively across all classes and sessions for the Market Maker. RTH DPMs for applicable classes can choose to retain or give up their DPM status during the GTH session. If DPM status is retained for the GTH session, then all DPM obligations will apply, including those applicable during opening rotation. Cboe may solicit for Market Makers to perform the GTH DPM role in classes where the RTH DPM declines.* *Subject to regulatory review Additional regulatory guidance will be provided in a forthcoming Regulatory Circular. Source: https://www.cboe.com/notices/content/?id=61230 What’s actually changing Cboe’s new structure adds two sessions to the trading day. The morning Global Trading Hours (GTH) session runs from 7:30 a.m. to 9:25 a.m. ET, with order acceptance starting at 7:15 a.m. ET. After the regular session closes at 4:00 p.m. ET, a brief 15-minute “curb session” extends trading to 4:15 p.m. ET. Why this matters for traders The practical impact centers on one thing: timing. Options traders have long faced an awkward gap between when market-moving information hits and when they can actually act on it with options contracts. If Nvidia drops guidance in a pre-market press release at 8:00 a.m. ET, equity traders could already adjust their stock positions. Options traders had to wait until 9:30 and hope their intended trade still made sense at whatever price the market had already moved to. That gap created a structural disadvantage for options-based strategies, particularly hedging. Portfolio managers holding large equity positions who rely on options for downside protection essentially had a 90-minute blind spot every morning where they could watch their stocks move but couldn’t adjust their hedges. That window just got significantly smaller. Institutional traders may benefit most in the near term. The 7:30 a.m. start aligns with European market hours, which could appeal to global funds managing cross-border portfolios. A London-based trader hedging US tech exposure no longer needs to wait until 2:30 p.m. local time to put on an options position.

Because most option traders live in 15-45 days-to-expiration land, there’s a myriad of factors they have to take into account when considering a trade in LEAPS options which aren’t present in short-term options. Implied Volatility is Higher in LEAPS Because of the long time to expiration for LEAPS, they carry higher implied volatility levels. This is intuitive, as in standard times, the VIX term structure is typically in contango, meaning future months get more expensive as you go into the future. Here’s an example of the VIX term structure at the time of writing, which is in contango: In other words, more can happen in more time. So the price of uncertainty goes up with time and hence the IV on LEAPS is expensive. Furthermore, there’s less selling pressure in LEAPS from option sellers. Premium sellers tend to pick shorter-dated options (<15 days) so they can quickly recycle their capital quickly. Selling LEAPS ties up your capital for long periods in exchange for a marginal increase in yield. It’s generally a bad trade, at least when it comes to systematic premium selling. They stay out of LEAPS and that keeps the IVs in LEAPS high. It might be obvious, but the best time to buy LEAPS is when the VIX is below its long-term average, and ideally when the underlying stock has a low IV Rank. The general consensus among academics who study volatility is that it clusters and trends in the short-term and mean-reverts in the long-term. For this reason, buying LEAPS at a low VIX and IV Rank puts extra wind at your back. Interest Rates and Dividends Actually Matter The average options trader lives in 15-45 days-to-expiration land. They seldom need to think hard about how their positions are impacted by the distributions of dividends, or changes in interest rates (Rho). But when it comes to LEAPS on a stock that pays a dividend, there’s going to be several dividend payments throughout the life of the option, and as we well know, interest rates can change dramatically over the course of 1-3 years. While these factors are mostly priced into market prices already, future changes in rates or dividends can impact your position in ways you don’t understand if you go into LEAPS blindly. Below is a chart from Lawrence McMillian’s excellent book Options As A Strategic Investment displaying a series of expirations and how their pricing differs with changes in interest rates. Note that the bottom line is value at expiration. And here’s a chart from the same book displaying how changes in dividends affects call option pricing: These two factors are of special importance in 2022’s market environment of rising interest rates and energy being the leading sector. Due to a myriad of factors, energy companies often choose to distribute earnings as dividends in lieu of investing in growth as tech companies might. Traders holding LEAPS in energy equities have probably learned a thing or two this year. LEAPS Have Far Less Liquidity Besides having less interest from option traders, market makers are generally less active in LEAPS and tend to quote very wide spreads. This can make establishing a position of any reasonable size a pain. Because option prices have definitive and knowable characteristics allowing you to ascribe a theoretical fair value to them, it’s far easier to get someone to trade with you if you’re will to pay a premium to the theoretical value. However, as good traders often say, getting into a trade is seldom a problem, getting out when out when you need to is the issue. How Traders and Investors Use LEAPS? Position Trades Many short-term traders who are used to holding their positions in the area of hours or days don’t like to/aren’t experienced at managing a longer-term delta-one position. Instead, they’ll often use LEAPS to express these longer-term views. Whatever their initial risk (perhaps 1% of their trading equity) would have been on the trade, they’ll use that to buy LEAPS, which they can kind of “set and forget” and not fiddle with stop losses and gap risk. This has the added benefits of providing leverage to their positions as well as not tying up much of their capital for long periods. An Alternative to Index Investing Whatever you think of the Boglehead philosophy of index investing being nearly the only way to invest smartly, they’ve had a pretty good track record for the last few decades when compared to actively managed fund options. But skeptics of passive investing still have a problem with blind faith in long-term return averages continuing into the future, but don’t want to miss out on potentially amazing yield. One way to replicate a return profile similar to that of passive index investing is to use LEAPS on index ETFs like SPY by periodically rolling at-the-money calls forward and funding the negative carry with the dividends supplied by a modestly sized high-yield dividend portfolio. Enhancing Returns of Long-Term Holdings Many hedge fund managers for whom their largest position is asymmetrically larger than the rest of their positions are presented with a problem. They’re loaded up to full size and then the position declines in value, creating an excellent opportunity to buy more at a great price. But they don’t have the capital or simply can’t risk more on what is already their largest position. In this case, they might use LEAPS to increase their upside for a small relative cost. Betting Against a Short Seller’s Nightmare Tesla (TSLA) is the perfect example of a stock that many traders desperately want to short exposure to, but the volatility is simply too high. There’s a whole graveyard of long/short managers who got taken to the cleaners shorting Tesla (TSLA). This is where buying LEAP puts would be a viable alternative. You still get the upside if your thesis is correct In the situation of Tesla, the bet was binary in nature for many of the company’s skeptics. They’re sure that the company is an eventual zero and if not unless they can find a strategic buyer like Volkswagen before the worst happens. Do note that this isn’t our view, instead, we’re just explaining the thinking of many Tesla shorts. In a binary situation like the one above, the put premium paid isn’t even of much concern if you expect such a dramatic move to the downside. The only concern is timing, of which LEAPS provides plenty. There’s a number of stocks in the same camp as Tesla in that the volatility is too difficult to deal with. Protecting Long-Term Positions Just as the Tesla bear might opt to use LEAPS calls to express their bearish view in a risk-defined manner, the Tesla bull might, too. With a stock like Tesla being such a high-risk, high-reward bet, even the bulls are aware of the significant risks to their thesis. For them, the trade is semi-binary in nature as it is for the shorts, at least far more so than buying the S&P 500 is. This is where they might use out-of-the-money LEAPS to protect their worst case downside while still benefiting from the same upside. Bottom Line While LEAPS aren’t very popular among traders due to opportunity cost on capital, they provide an excellent avenue for traders to limit their risk while making long-term leveraged bets. It’s for this reason that LEAPS are frequently overpriced, because there are few natural sellers. If you dip your toe into LEAPS, make sure you take heed of the differences between LEAPS and short-term options: Lower liquidity Higher IV Dividends and interest rates actually have a significant impact on LEAPS positions.

As a reminder, a strangle involves buying calls and puts on the same stock with different strikes. Buying calls and puts with the same strike is called a long straddle. Strangles usually provide better leverage in case the stock moves significantly. So let’s see how it works. First, you must identify stocks which have a history of big post-earnings moves. Some examples include AMZN, Netflix, Google, Priceline (PCLN), and others. Then you buy a strangle or a straddle a day or two before the earnings are announced. If the stock has a big move, you sell for a big profit. The problem is you are not the only one knowing that earnings are coming. Everyone knows that those stocks move a lot after earnings, and everyone bids those options. Following the laws of supply and demand, those options become very expensive before earnings. The IV (Implied Volatility) jumps to the roof. The next day the IV crashes to the normal levels and the options trade much cheaper. Let’s examine a few test cases from the 2011 earnings cycle. AKAM announced earnings on Oct. 26. The $24 straddle could be purchased for $4.08. IV was 84%. The next day the stock jumped 15%, yet the straddle was worth only $3.81. The reason? IV collapsed to 47%. The market “expected” the stock to move 17-18%, based on previous moves, but the stock moved “only” 15% and the straddle lost 7%. BIDU announced earnings on Oct. 26. The stock moved 4.5% following the earnings. You could purchase the straddle at $19.55 the day before earnings. The same straddle was worth $13.47 the next day. That’s a loss of 31%. TIVO moved 2%, the straddle lost 29%. FSLR moved 3%, the straddle lost 55%. Now let’s check a couple of good trades. NFLX announced earnings on October 24. The stock collapsed 34.9% the next day, a move of historical proportions. The 120 strangle could be purchased the day before earnings at $24.52 and sold the next day at $43.00. That’s a 75% gain, but this is as good as it gets. This is a move of historic proportions but the trade is even not a double. AMZN straddle gained 57%. CME straddle gained 62%. GMCR straddle gained 84%. It is easy to get excited after a few trades like NFLX, GMCR, CME and AMZN. However, we have to remember that those stocks experienced much larger moves than their average move in the last few cycles. In some cases, the move was double what was expected. NFLX and GMCR moved more than 35%, the largest moves in at least 10 years. Chances are this is not going to happen every cycle. There is no reliable way to predict those events. The big question is the long term expectancy of the strategy. It is very important to understand that for the strategy to make money it is not enough for the stock to move. It has to move more than the markets expect. In some cases, even a 15-20% move might not be enough to generate a profit. Some people might argue that if the trade is not profitable the same day, you can continue holding or selling only the winning side till the stock moves in the right direction. It can work under certain conditions. For example, if you followed the specific stock in the last few cycles and noticed some patterns, such as the stock continuously moving in the same direction for a few days after beating the estimates. Another example is holding the calls when the general market is in uptrend (or downtrend for the puts). However, it has nothing to do with the original strategy. From the minute you decide to hold that trade, you are no longer using the original strategy. If the stock didn’t move enough to generate a profit, you must be ready to make a judgement call by selling one side and taking a directional bet. This might work for some people, but the pure performance of the strategy can be measured only by looking at a one day change of the strangle or the straddle (buying a day before earnings, selling the next day). The bottom line: Over time the options tend to overprice the potential move. Those options experience huge volatility drop the day after the earnings are announced. In most cases, this drop erases most of the gains, even if the stock had a substantial move. Jeff Augen, a successful options trader and author of six books, agrees: “There are many examples of extraordinary large earnings-related price spikes that are not reflected in pre-announcement prices. Unfortunately, there is no reliable method for predicting such an event. The opposite case is much more common – pre-earnings option prices tend to exaggerate the risk by anticipating the largest possible spike.” It doesn’t necessarily mean that the strategy cannot work and produce great results. However, in most cases, you should be prepared to hold beyond the earnings day, in which case the performance will be impacted by many other factors, such as your trading skills, general market conditions etc. To hedge your bets and reduce the loss if the stock doesn't move, you might consider trading a Reverse Iron Condor. This article was originally published here. Related articles: How We Trade Straddle Option Strategy Exploiting Earnings Associated Rising Volatility Buying Premium Prior To Earnings - Does It Work? Can We Profit From Volatility Expansion Into Earnings? Long Straddle: A Guaranteed Win? Straddle, Strangle Or Reverse Iron Condor (RIC)? How We Made 23% On QIHU Straddle In 4 Hours Why We Sell Our Straddles Before Earnings Selling Strangles Prior To Earnings How To Calculate ROI On Credit Spreads Straddle Option Overview Long Straddle Through Earnings Backtest Straddles - Risks Determine When They Are Best Used The Gut Strangle Long And Short Straddles: Opposite Structures