{"id":7045641,"date":"2026-08-24T05:03:14","date_gmt":"2026-08-24T05:03:14","guid":{"rendered":"https:\/\/peraltafinancing.com\/business\/finance\/will-a-long-short-direct-index-help-my-tax-bill\/"},"modified":"2026-08-24T05:03:14","modified_gmt":"2026-08-24T05:03:14","slug":"will-a-long-short-direct-index-help-my-tax-bill","status":"publish","type":"post","link":"https:\/\/fivemor.com\/?p=7045641","title":{"rendered":"Will A Long-Short Direct Index Help My Tax Bill?"},"content":{"rendered":"<p> <br \/>\n<\/p>\n<div>\n<div class=\"wp-block-group\">\n<div class=\"wp-block-group__inner-container is-layout-constrained wp-block-group-is-layout-constrained\">\n<p><em>Don\u2019t miss an episode of our podcast,\u00a0<strong>Personal Finance for Long-Term Investors<\/strong>. Available on all podcast players. <\/em><\/p>\n<p>Here\u2019s the latest episode: <\/p>\n<p><iframe allow=\"autoplay *; encrypted-media *; fullscreen *; clipboard-write\" frameborder=\"0\" height=\"175\" style=\"width:100%;max-width:660px;overflow:hidden;border-radius:10px;\" sandbox=\"allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation\" src=\"https:\/\/embed.podcasts.apple.com\/us\/podcast\/is-my-diy-financial-plan-working-e148\/id1553180943?i=1000782881772\"><\/iframe><\/p>\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n<\/div>\n<\/div>\n<p>Podcast listener <strong>Wes<\/strong> wrote to me: <\/p>\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p><em>Jesse \u2013 I appreciate the great podcast and blog content that goes beyond personal finance 101. I have a question about generating investment losses to offset appreciated assets and\/or the income from a Roth conversion. My advisor has been talking about a long\/short strategy that I\u2019m researching. However, I was thinking I could either short a stock I think that will go up (risky) or simply buy a leveraged ETF (less risky) that is say the inverse of the S&amp;P500 like SSO. Seems like a simple strategy but I don\u2019t see much content out there about this so I\u2019m guessing I\u2019m missing some pitfalls. Can you give me some input?<\/em><\/p>\n<\/blockquote>\n<p>Hi Wes, thanks for the question. Very interesting.<\/p>\n<p>Now\u2026I\u2019d like to paint a little picture for you.\u00a0<\/p>\n<p>You have $10,000 in gains, all of which will be subject to a 15% capital gains tax. So, you\u2019d owe $1500 in tax.\u00a0<\/p>\n<p>You then pursue a strategy that creates $10,000 in losses. This offsets the ENTIRE gain and ELIMINATES the tax. Ok \u2013 nice! So, you eliminated that $1500 tax.\u00a0<\/p>\n<p><strong>BUT\u2026<\/strong><\/p>\n<p>You also have $10,000 in losses. You no longer actually profited. The losses totally offset and wipe out your gains.<\/p>\n<p>Would you rather have $10,000 in gains and pay $1,500 in taxes?<\/p>\n<p>Or have no gains whatsoever?\u00a0<\/p>\n<p>I\u2019d take the first scenario every day.\u00a0 Why lose $10,000 to save $1,500?\u00a0<\/p>\n<p>Now, I\u2019ve painted a very, very simple scenario. Most of the strategies that professionals might use will *attempt* to be more nuanced and complex than this.\u00a0<\/p>\n<p>What they <em>hope<\/em> to do is create some losses and some gains. The losses will be <strong>realized<\/strong>. The gains will be <strong>unrealized<\/strong>. Your realized losses can be used to lower this year\u2019s tax bill. And those new, unrealized gains? We kick them down the road to a future tax year. We don\u2019t have to pay taxes on unrealized gains (yet). <\/p>\n<p>The question becomes\u2026<strong>will we <em>ever<\/em> have to pay taxes on unrealized gains?\u00a0<\/strong><\/p>\n<p>I hope you see that you can never \u201coutrun\u201d this tax problem EXCEPT by dying. When you die, your taxable estate goes to your heirs at a stepped-up basis, wiping out the capital gains.\u00a0<\/p>\n<h2 class=\"wp-block-heading\">Is \u201cDeath\u201d Considered a Big Win?!<\/h2>\n<p>This brings about a funny little pattern in financial planning circles where we have to balance two competing ideas:\u00a0<\/p>\n<p>The first idea is that everyone will die someday. We MUST treat death as a reality.\u00a0<\/p>\n<p>But the second idea is that we need to be a little cautious about treating death as a \u201cwin\u201d and living as a \u201closs.\u201d This scenario is one example. <em>Sweet! You die with unrealized capital gains, and your heirs get a big win!!<\/em> It\u2019s true. You\u2019re still dead, though. And you didn\u2019t get to spend your money.\u00a0<\/p>\n<p><span style=\"box-sizing: border-box; margin: 0px; padding: 0px;\">Another example:\u00a0<em>you claimed Social Security at 62, and that ended up being SUPER SMART because you died at 71, well before the \u201cbreak-even age\u201d for delaying.<\/em><\/span><em> Good thing you claimed at 62! <\/em><\/p>\n<p>Who are we talking to here? The dead 71-year-old? Did they win?\u00a0<\/p>\n<p>Another example: <em>Oh man\u2026you wasted $2,000 a year for 30 years on life insurance. What a WASTE. <\/em>\u00a0<\/p>\n<p>You\u2019re saying\u2026I failed because I survived?\u00a0<\/p>\n<p>Yes, death is a reality for all of us eventually. And I genuinely think there comes a time when, for example, we should prudently say, <em>\u201cShould we realize capital gains for this very sick 87-year-old, or do we discuss the idea of their death?\u201d<\/em><\/p>\n<h2 class=\"wp-block-heading\">Back to Long-Short Direct Indexing<\/h2>\n<p>But I\u2019ll occasionally get emails from a 55-year-old who thinks they\u2019re going to kick the tax can down the road on their highly appreciated tech stocks until they die.\u00a0<\/p>\n<p>Short of dying, though, what these \u201ctax loss strategies\u201d attempt to do is, again, create some losses THIS YEAR\u2026while not actually losing you money on net.\u00a0<\/p>\n<p>Some of these strategies use <strong>leverage, or borrowed money<\/strong>, to give you extra exposure. This is a weird concept, so let me see if I can explain it.\u00a0<\/p>\n<p>You invest $100. On top of that, you borrow another $100. That\u2019s the leverage. And that leverage comes at a cost. Right? Borrowing money, taking a loan\u2026that has a cost. We\u2019ll put in a pin in that cost for now.\u00a0<\/p>\n<p>Now, you have $200 to invest.<\/p>\n<p>You invest $150 of that in the S&amp;P500. Or, if you want to get more technical, you\u2019re probably building a direct index of the S&amp;P 500 by owning all 500 companies. Either way\u2026you have $150 invested long. <\/p>\n<p>You then invest the final $50 by <em>shorting<\/em> the S&amp;P 500. Yes\u2026you are betting against yourself.\u00a0<\/p>\n<p>On net, though, you have $150 long and $50 short, so your net exposure is $100 long. In other words, you have the same investment exposure as if you had only invested your own $100 in the S&amp;P. You\u2019re not taking any extra investment risk.\u00a0<\/p>\n<p>But you know that, in most years, at least <em>some<\/em> part of your portfolio is going to create losses. Or, if you went the direct indexing route, you know that some of your investments are definitely going to lose money.\u00a0<\/p>\n<p>Let\u2019s say your shorts lose money. You sell them. Those losses can then be used to offset other gains from your portfolio or the taxes from Roth conversions.\u00a0<\/p>\n<p>And Wes, your advisor would likely say, <\/p>\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p><em>\u201cAnd you didn\u2019t actually lose any money, because your longs are up! The longs\u2019 unrealized gains more than make up for these shorts losing money.\u201d\u00a0<\/em><\/p>\n<\/blockquote>\n<p>That\u2019s a factual statement.\u00a0<\/p>\n<p>But would you have been better off, say, being 100% long and not dealing with any losses in the first place? I\u2019d wager <strong>YES<\/strong>, at least for most people.\u00a0<\/p>\n<h2 class=\"wp-block-heading\">When Tax-Loss Strategies Work Best<\/h2>\n<p>In my experience, the <strong>BEST<\/strong> strategies for using losses to offset gains occur <strong>when the losses are incidental, not when the losses are purposeful.<\/strong><\/p>\n<p>Not all of us will have incidental losses in our investing lives, let alone on an annual basis. That\u2019s ok. Sometimes we\u2019ll be able to offset those capital gains taxes or income taxes. Other times we won\u2019t.\u00a0<\/p>\n<p>We shouldn\u2019t let the tax tail (15%) wave the investing dog (100%) though.\u00a0<\/p>\n<p>Now\u2026 this has the same issues as all direct indexing strategies, which we discussed in <a href=\"https:\/\/podcasts.apple.com\/us\/podcast\/the-optimal-retirement-withdrawal-framework-account\/id1553180943?i=1000736374935\">episode 121<\/a>. Higher costs. Tax pitfalls. Tracking error against the index. Diminishing benefits over time. Higher minimums. It <em>only<\/em> applies to taxable accounts, not to retirement accounts.\u00a0<\/p>\n<p><iframe allow=\"autoplay *; encrypted-media *; fullscreen *; clipboard-write\" frameborder=\"0\" height=\"175\" style=\"width:100%;max-width:660px;overflow:hidden;border-radius:10px;\" sandbox=\"allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation\" src=\"https:\/\/embed.podcasts.apple.com\/us\/podcast\/the-optimal-retirement-withdrawal-framework-account\/id1553180943?i=1000736374935\"><\/iframe><\/p>\n<p>The diminishing benefit of long-short direct indexing strategies \u2013 it\u2019s a big deal. A lot of these strategies require \u201cforever maintenance.\u201d Because, if you recall, you\u2019re not making the capital gains disappear. While one side of your direct index \/ long-short portfolio is kicking off losses, the other side is creating unrealized gains. And to liquidate this portfolio and realize all those gains\u2026well, that flies in the face of what you\u2019re even trying to accomplish in the first place. Who would do that? So, you\u2019re going to maintain your direct index for a long time.\u00a0<\/p>\n<h2 class=\"wp-block-heading\">The Cost \/ Benefit of Long-Short Direct Indexing<\/h2>\n<p>But\u2026the <em>costs<\/em> of the direct index portfolio will still be there.\u00a0Those additional costs will decay your performance over time. <\/p>\n<p>So, if you\u2019re choosing to pursue one of these strategies, I think it\u2019s important to look at what your tax savings might be this year, next year, or in the other high tax years of your life.\u00a0<\/p>\n<p>Then, it\u2019s important to see how much in losses your portfolio might generate, because (as long as markets generally go up over time), you\u2019ll have fewer and fewer losses as time goes on.\u00a0<\/p>\n<p>Then you\u2019ll need to measure how much in direct index fees you\u2019ll expect to pay, not just this year, next year, or the year after\u2026.but for <em>decades.\u00a0<\/em><\/p>\n<p>It can feel amazing, and perhaps it <em>is<\/em> amazing, if you get 3% or 4% in \u201ctax alpha\u201d or \u201cextra performance\u201d that comes from saving money on taxes. But eventually that tax alpha drops to zero. The fund is no longer creating meaningful losses, and even if it were, you might not be in a tax scenario to use them. But at, say, 0.5% in fees per year, any tax alpha you once benefited from is getting slowly eaten away.\u00a0<\/p>\n<p>The people who are using this strategy \u201cthe best\u201d are <em>NOT<\/em> late 60\u2019s retirees.\u00a0<\/p>\n<p>They are in their 40s and 50s, are high earners in the best years of their careers, and\/or are receiving equity compensation from a publicly traded company. These are people who might have to hold this direct index for 30 or 40 or 50 more years (until their death), lest they want to realize the capital gains that they avoided in the first place. But holding this strategy for 30 or 40 years has its own big problems, as we just discussed. <\/p>\n<p>In summary\u2026I have serious reservations about this strategy.\u00a0<\/p>\n<p>For the vast majority of people out there, including many of the wealthier people who might be reading right now, I\u2019d be particularly cautious here. <\/p>\n<p>This strategy is likely to have more complexity costs than are worthwhile \u2013 at least in its current format and fee structure. <\/p>\n<p>Thank you for reading! Here are three quick notes for you: <\/p>\n<p><strong>First<\/strong> \u2013 If you enjoyed this article, join 1000\u2019s of subscribers who read Jesse\u2019s free weekly email, where he send you links to the smartest financial content I find online every week. 100% free, unsubscribe anytime.<\/p>\n<p><strong>Second<\/strong> \u2013 Jesse\u2019s podcast <em><strong><a href=\"https:\/\/bestinterest.blog\/personal-finance-for-long-term-investors\/\">\u201cPersonal Finance for Long-Term Investors\u201d<\/a><\/strong><\/em> has grown ~10x over the past couple years, now helping ~10,000 people per month. <strong><a href=\"https:\/\/podcasts.apple.com\/us\/podcast\/the-best-interest-personal-finance-for-long-term-investors\/id1553180943\">Tune in and check it out.<\/a>   <\/strong><\/p>\n<p><strong>Last<\/strong> \u2013 Jesse works full-time for a fiduciary wealth management firm in Upstate NY. Jesse and his colleagues help families solve the expensive problems he writes and podcasts about. <a href=\"https:\/\/bestinterest.blog\/work\/\"><strong>Schedule a free call with Jesse<\/strong><\/a> to see if you\u2019re a good fit for his practice. <\/p>\n<p>We\u2019ll talk to you soon! <\/p>\n<\/div>\n\n","protected":false},"excerpt":{"rendered":"<p>Don\u2019t miss an episode of our podcast,\u00a0Personal Finance for Long-Term Investors. Available on all podcast players. Here\u2019s the latest episode: Podcast listener Wes wrote to me: Jesse \u2013 I appreciate the great podcast and blog content that goes beyond personal finance 101. I have a question about generating investment losses to offset appreciated assets and\/or [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":7045642,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[93],"tags":[6795,5988,11279,208140,7356],"dealstore":[],"offerexpiration":[],"class_list":["post-7045641","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-finance","tag-bill","tag-direct","tag-index","tag-longshort","tag-tax"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.4 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Will A Long-Short Direct Index Help My Tax Bill? - Som2ny Network<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/fivemor.com\/?p=7045641\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Will A Long-Short Direct Index Help My Tax Bill? - Som2ny Network\" \/>\n<meta property=\"og:description\" content=\"Don\u2019t miss an episode of our podcast,\u00a0Personal Finance for Long-Term Investors. 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Available on all podcast players. Here\u2019s the latest episode: Podcast listener Wes wrote to me: Jesse \u2013 I appreciate the great podcast and blog content that goes beyond personal finance 101. 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