<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd" xmlns:googleplay="http://www.google.com/schemas/play-podcasts/1.0"><channel><title><![CDATA[Casey Schorr]]></title><description><![CDATA[Notes on money, investing, and life after selling a business.]]></description><link>https://www.caseyschorr.com</link><image><url>https://substackcdn.com/image/fetch/$s_!9uEP!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd1f91f40-b20e-49e3-8d7f-23cb9829282e_1502x1502.jpeg</url><title>Casey Schorr</title><link>https://www.caseyschorr.com</link></image><generator>Substack</generator><lastBuildDate>Tue, 15 Sep 2026 00:46:54 GMT</lastBuildDate><atom:link href="https://www.caseyschorr.com/feed" rel="self" type="application/rss+xml"/><copyright><![CDATA[Casey Schorr]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[caseyschorr@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[caseyschorr@substack.com]]></itunes:email><itunes:name><![CDATA[Casey Schorr]]></itunes:name></itunes:owner><itunes:author><![CDATA[Casey Schorr]]></itunes:author><googleplay:owner><![CDATA[caseyschorr@substack.com]]></googleplay:owner><googleplay:email><![CDATA[caseyschorr@substack.com]]></googleplay:email><googleplay:author><![CDATA[Casey Schorr]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[I know our net worth, but not what our life costs]]></title><description><![CDATA[I spent years trying to get the portfolio right without knowing how much we were spending.]]></description><link>https://www.caseyschorr.com/p/what-our-life-costs</link><guid isPermaLink="false">https://www.caseyschorr.com/p/what-our-life-costs</guid><dc:creator><![CDATA[Casey Schorr]]></dc:creator><pubDate>Wed, 09 Sep 2026 14:53:00 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/bdd911b9-e491-4f33-808c-b8a0defc9d90_1200x630.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><span>After leaving the company that acquired mine, I opened Chase and saw a negative balance in our checking account.</span></p><p><span>I wasn&#8217;t out of money. The Printfection sale had left me with money in a taxable investment account that I could transfer. The problem was I had no idea what our life actually cost.</span></p><p><span>For years, our finances had mostly taken care of themselves. Our paychecks came in. The bills went out. I didn&#8217;t think much about what we were spending because the checking account kept filling back up.</span></p><p><span>Without my paycheck coming in, I had to check each month what was left in checking and what was coming due, then transfer enough from the taxable account to cover the gap. At first, the transfers didn&#8217;t bother me. But after a while, the amount seemed like way too much, even with Megan&#8217;s income.</span></p><p><span>I didn&#8217;t think we were living extravagantly but wasn&#8217;t paying especially close attention. We did have a full-time nanny and traveled more after the exit.</span></p><p><span>But some of the money leaving the taxable account wasn&#8217;t ordinary family spending. It also covered ongoing costs for our mountain lot in Crested Butte, architectural plans for a house, taxes from the sale, and expenses for a small business I&#8217;d started.</span></p><p><span>I couldn&#8217;t tell if we were spending more, everything had gotten more expensive, or I was mistaking other withdrawals for spending.</span></p><p><span>It was embarrassing. I&#8217;d spent years studying withdrawal rates and </span><a href="https://www.caseyschorr.com/p/risk-parity-after-selling-my-business"><span>building a resilient portfolio</span></a><span>. But I hadn&#8217;t figured out what we were spending or if it had gotten out of hand.</span></p><h2><span>Why I couldn&#8217;t tell what our life costs</span></h2><h3><span>Net worth</span></h3><p><span>I could open Monarch, a personal finance app, and see our net worth right away. It felt good to see that number hadn&#8217;t changed much.</span></p><p><span>But net worth answered the wrong question. Money I&#8217;d moved from the taxable account into the lot and our kids&#8217; college savings accounts still counted toward our net worth, even as the account we depended on kept shrinking.</span></p><h3><span>Taxable account withdrawals</span></h3><p><span>I was starting to worry about how much money was leaving the taxable account. But not all of it was spending.</span></p><p><span>Some of it made up the difference between Megan&#8217;s salary and our ordinary spending. A lot of it paid taxes on sale proceeds that had gone into the account but were never really mine to spend. Then there was the lot: property taxes and architectural work for the house we hoped to build. I also put some of it toward my small business.</span></p><p><span>When I ran Printfection, I never would have treated operating expenses, taxes, buying property, and investing in a new venture as the same thing. But at home, all I had was one vague feeling: we&#8217;re spending too much.</span></p><h3><span>Spending</span></h3><p><span>I went through our 2024 transactions in Monarch while getting ready for taxes. The total was way higher than I expected.</span></p><p><span>But I didn&#8217;t trust it.</span></p><p><span>The total depended on Monarch bringing in every transaction and me deciding what counted as normal spending.</span></p><p><span>But Monarch didn&#8217;t reconcile transactions against our bank and credit card statements. When I checked the statements, I found transactions missing from Monarch. The same transactions were missing from other apps that used Plaid to connect to our accounts. None warned me that anything was wrong.</span></p><h2><span>I still don&#8217;t want to budget</span></h2><p><span>I&#8217;ve never wanted a budget. Partly because it makes me feel restricted even when we can afford something. Partly because I don&#8217;t want another system to maintain. I&#8217;d rather make decisions as they come than set a spending limit for every category.</span></p><p><span>But I do need to know how much we spend over a year.</span></p><p><span>After the sale, it became easier to say yes. The kids were out of school, and we could afford another trip. Why not go?</span></p><p><span>I bought a boat. I was getting restless in Denver and wanted something adventurous our family could do close to home. It meant paying more than $600 a month for a storage unit. A full-time nanny was incredibly convenient, but it cost at least twice as much as preschool for Ava and after-school care for Liam.</span></p><p><span>Each choice seemed reasonable on its own. Not knowing what they added up to felt reckless.</span></p><p><span>I&#8217;m not trying to cut everything. I just want to see where the money is going and whether it&#8217;s worth it.</span></p><p><span>Seeing all those choices together over a full year would help us decide what to keep and what to cut. We could leave more money invested or spend more weekends skiing as a family. I&#8217;ve never come home wondering if it was worth the money.</span></p><h2><span>I wish I&#8217;d understood our spending sooner</span></h2><p><span>Right after the sale, I was anxious to get all that money out of checking and invested. I focused on the portfolio and mostly guessed at what our life cost.</span></p><p><span>If I&#8217;d understood it better, I might have spent less on some things and more confidently on others. That could have changed the portfolio I built or the work I pursued. Maybe I wouldn&#8217;t have bought land for the mountain home and outdoor life I wanted for our family.</span></p><p><span>Now I&#8217;m doing the boring work I skipped: going back to original statements, reconciling the accounts, and deciding exactly what counts as ordinary spending. Then I can use that definition consistently and see how our spending changes over time.</span></p><p><span>I put this work off because categorizing transactions felt tedious and I didn&#8217;t understand why it mattered. I still don&#8217;t enjoy it but want numbers Megan and I can trust.</span></p><p><span>I&#8217;m figuring it out but still don&#8217;t know what we spend in a normal year or if the portfolio can keep up.</span></p>]]></content:encoded></item><item><title><![CDATA[Sequence of returns risk]]></title><description><![CDATA[Once a portfolio is funding life, the order of returns can matter as much as the returns themselves.]]></description><link>https://www.caseyschorr.com/p/sequence-of-returns-risk</link><guid isPermaLink="false">https://www.caseyschorr.com/p/sequence-of-returns-risk</guid><dc:creator><![CDATA[Casey Schorr]]></dc:creator><pubDate>Tue, 16 Jun 2026 17:42:00 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/a3c3b81a-e422-4c8c-91f5-b5d26b74802f_1200x630.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><span>Sequence of returns risk is the risk that the same investment returns produce different outcomes depending on the order they arrive in, once money is being withdrawn from the portfolio.</span></p><p><span>Start with $2 million and withdraw a fixed $80,000 at the end of each year: 4% of the starting portfolio. One five-year path is -30%, -10%, +15%, +20%, +25%. Another path uses the same five returns in reverse order.</span></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!zyE4!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!zyE4!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 424w, https://substackcdn.com/image/fetch/$s_!zyE4!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 848w, https://substackcdn.com/image/fetch/$s_!zyE4!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 1272w, https://substackcdn.com/image/fetch/$s_!zyE4!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!zyE4!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png" width="1400" height="620" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:620,&quot;width&quot;:1400,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:57825,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://caseyschorr.substack.com/i/215289475?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!zyE4!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 424w, https://substackcdn.com/image/fetch/$s_!zyE4!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 848w, https://substackcdn.com/image/fetch/$s_!zyE4!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 1272w, https://substackcdn.com/image/fetch/$s_!zyE4!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7c77cd0e-993a-429f-a6d9-2d4a9641a8b0_1400x620.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><span>Without withdrawals, both paths end in the same place: about $2.2 million.</span></p><p><span>Once withdrawals begin, the order matters. The bad-first path ends around $1.61 million after five years. The good-first path ends around $1.86 million.</span></p><p><span>The five-year gap is roughly $250,000.</span></p><p><span>But the deeper problem is that every later year compounds from the smaller base.</span></p><p><span>By year 15, the gap is about $535,000.</span></p><p><span>By year 25, it is about $1.16 million.</span></p><p><span>That $1.16 million gap is more than fourteen years of $80,000 withdrawals that never had a chance to compound.</span></p><p><span>Same returns. Different order. Different life.</span></p><h2><span>Why withdrawals change the math</span></h2><p><span>Average return stops being enough once the portfolio has to fund life.</span></p><p><span>If no money is moving in or out, the order of annual returns does not change the final value. The same returns in a different order end at the same number.</span></p><p><span>Once withdrawals start, the order matters.</span></p><p><span>Bad early years do more than create paper losses. They shrink the base of capital while the portfolio is also funding life. Each withdrawal comes from a smaller base. The later recovery helps, but it has fewer dollars left to compound. It cannot compound on dollars that have already been spent.</span></p><p><span>The simple version: markets fall soon after the portfolio starts funding life, and the recovery has fewer dollars to work with. Selling while prices are down is how temporary losses become lasting damage.</span></p><p><span>The long-term average can look healthy while the early path breaks the plan.</span></p><h2><span>Money going in vs. money coming out</span></h2><p><span>Bad early returns can help when money is going in and hurt when money is coming out.</span></p><p><span>When money is going in, early losses still hurt, but new savings are invested at lower prices. The recovery is not doing all the work by itself. A bad early sequence can even help if the investor keeps buying through the drawdown.</span></p><p><span>When money is coming out, the portfolio has to repair itself without fresh capital coming in, while also paying for life. Early losses shrink the base, and withdrawals come out of that smaller base. The portfolio is trying to recover while it is still wounded. That is how a temporary drawdown can become lasting damage. Dollars sold after a drawdown are no longer there for the rebound.</span></p><p><span>Recovery time still helps. But once withdrawals begin, the portfolio has to rebuild while money is still coming out.</span></p><h2><span>Why it mattered after the exit</span></h2><p><span>After selling my business, I was not just choosing an asset allocation. The exit created real freedom, but not immunity from math. I was asking whether a finite portfolio could support my family for decades, starting much earlier than traditional retirement.</span></p><p><span>That turned sequence risk into one of the main design problems.</span></p><p><span>The usual answers tend to work around the problem: withdraw less, keep a stock-heavy portfolio, hold a cash cushion, add private investments, hire an adviser, or accept a more conservative version of life. Some of those choices are reasonable. But they do not necessarily solve the sequence problem.</span></p><p><span>The obvious way to reduce sequence risk is to withdraw less. A lower withdrawal rate reduces pressure on the portfolio. But it also pays for sequence risk in advance by making life smaller. A 3% life and a 6% life are not the same life.</span></p><p><span>A stock-heavy portfolio can sound like a more ambitious answer: accept volatility, trust the long-run return, and wait. But if the plan still depends mostly on equity-like risk being rewarded soon enough, smoothly enough, and in the right order, the plan still has a sequence problem.</span></p><p><span>That is why </span><a href="https://www.caseyschorr.com/p/risk-parity"><span>risk parity</span></a><span> became interesting to me. It was not another plan built around equity risk carrying most of the load. Equities still matter as one of the main engines of long-term growth. The risk parity insight was that equities did not have to carry the withdrawal plan alone.</span></p><p><span>Combining return streams with different reasons for working and sizing them by risk is how the portfolio is built to create a smoother path without simply lowering the withdrawal rate.</span></p><p><span>That is the mechanical link to sequence risk: a shallower early drawdown means withdrawals come out of a less damaged portfolio, so the bad order does less permanent damage. The upside is not just less pain. If the early path is less damaging, the same capital can support more spending without depending as much on a lucky sequence.</span></p><h2><span>How I use the term</span></h2><p><span>When I say sequence of returns risk, I mean the withdrawal problem: losses arriving early, after money has started coming out.</span></p><p><span>It is not a prediction that bad returns are coming, and it is not just another name for volatility. The problem also does not disappear just because stocks tend to win over long periods.</span></p><p><span>Long-run returns still matter. But the term forces a different test: can the portfolio survive the bad years arriving first?</span></p><h2><span>Designing for a bad sequence</span></h2><p><span>If the bad years arrive first, can the portfolio design make them less destructive without simply shrinking the life the exit was meant to support?</span></p><p><span>The answer starts with return streams that do not all need the same kind of market to work. A risk parity-style portfolio goes further by sizing those streams so one bad run in one stream is less able to dominate the whole withdrawal path.</span></p><p><span>In my own system, that means sizing three main return streams: equities, Treasury exposure, and trend following. Equities still provide long-term growth, but they are not the only stream carrying the withdrawal plan through a bad early sequence. Treasury exposure and trend following add return streams with different drivers, so the plan is not just waiting for equities to recover.</span></p><p><span>For a portfolio that is withdrawing, a shallower hole early often matters more than a higher peak.</span></p><h2><span>What I test</span></h2><p><span>The long-run average is not enough. I want to know what happens if the first decade is ugly.</span></p><p><span>That means testing the depth of early drawdowns, the length of the recovery, how much selling happens while the portfolio is down, whether one return stream dominates the withdrawal path, and whether the portfolio still works when the good years arrive late.</span></p><p><span>That is why sequence of returns risk sits underneath so much of my portfolio work. It is why risk parity became interesting to me, why I care about return streams like trend following and Treasury exposure, and why I keep testing whether the added complexity actually makes the withdrawal path more durable.</span></p><p><span>I am testing all of it against the same question: can the portfolio survive a bad order of returns while money is coming out?</span></p><h2><span>What can still go wrong</span></h2><p><span>Sequence of returns risk cannot be eliminated.</span></p><p><span>Even a carefully built mix of return streams can still get a bad sequence. Leverage can magnify a weak design. Different-looking investments can still depend on the same underlying risk.</span></p><p><span>The goal is not to find a perfect allocation. It is to know whether the portfolio has been built and tested for the withdrawal problem, not just average return.</span></p><h2><span>The real question</span></h2><p><span>Once the portfolio is supporting the life the exit was meant to buy, can it survive the bad years arriving first, or did the plan depend all along on the good years showing up at the right time?</span></p>]]></content:encoded></item><item><title><![CDATA[Why I built a risk parity portfolio after selling my business]]></title><description><![CDATA[The standard answer protected the money but not the life the exit was supposed to make possible.]]></description><link>https://www.caseyschorr.com/p/risk-parity-after-selling-my-business</link><guid isPermaLink="false">https://www.caseyschorr.com/p/risk-parity-after-selling-my-business</guid><dc:creator><![CDATA[Casey Schorr]]></dc:creator><pubDate>Thu, 04 Jun 2026 20:53:00 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/92e7c478-fb16-4779-8d7c-d314507aa48b_1200x630.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><span>A few days before Christmas 2021, a few minutes before the wire cutoff, the money hit my checking account.</span></p><p><span>For a moment, it felt unreal. I had sold my company. A seven-figure balance was sitting there, visible on a screen, after years of building a business that had been the center of my adult life.</span></p><p><span>And then reality sank in.</span></p><p><span>I had traded a living, breathing money machine for a static pile of cash.</span></p><p><span>No more salary from the thing I had built. No more distributions. No operating business throwing off cash. What I had instead were the proceeds from the sale, and the question I had not fully understood until the wire landed:</span></p><p><span>Could this money support the life I had sold the company to make possible?</span></p><p><span>The exit was supposed to buy flexibility. Time with my family. Space to recover from the startup years. Room to think. The mountain house we had kept dreaming about. Maybe a different relationship to work entirely.</span></p><p><span>But the money was also what kept that flexibility alive. If I managed it badly, the freedom could disappear.</span></p><p><span>So the new job became clear: don&#8217;t screw this up.</span></p><p><span>Money was not the point. But it was now the foundation under everything I wanted the exit to make possible.</span></p><h2><span>The standard answer did not fit</span></h2><p><span>The first place I turned was the investing philosophy I already trusted. I had been a </span><a href="https://bogleheads.org/wiki/Getting_started"><span>Boglehead</span></a><span> for years: low-cost index funds, broad diversification, buy and hold, do not try to outsmart the market. It is a simple, disciplined philosophy, and for a long accumulation period it still makes a lot of sense.</span></p><p><span>But my situation had changed.</span></p><p><span>I was no longer steadily adding money from a paycheck. I was trying to understand whether a finite portfolio could support a family for decades, starting much earlier than traditional retirement.</span></p><p><span>I talked to traditional advisors. I looked at robo-advisors. I considered stock picking and angel investing, then remembered that turning my portfolio into another full-time job was the opposite of freedom.</span></p><p><span>Everywhere I looked, the answer was the same:</span></p><p><span>You are younger than a normal retiree, so be extra conservative: plan to withdraw something like 2.5% to 3% a year.</span></p><p><span>That answer was probably responsible. It was also depressing.</span></p><p><span>At 3%, the math felt safe, but our life would get smaller than the one I thought the exit had made possible. It was the difference between one of us stepping back and both of us having real room to breathe. It was the difference between talking about the mountain house and actually building it.</span></p><p><span>I had not sold the company just to preserve a cautious version of our life. I wanted a financial base that could support more freedom, not just less risk.</span></p><p><span>So I kept looking.</span></p><h2><span>Finding risk parity</span></h2><p><span>I found the first real clue in a very internet way: scrolling through r/financialindependence, r/fatFIRE, and Bogleheads threads, trying to figure out whether the standard answer was really the only sane option.</span></p><p><span>That is where I found the now-famous </span><a href="https://www.bogleheads.org/forum/viewtopic.php?t=272007"><span>Hedgefundie thread</span></a><span>.</span></p><p><span>My first reaction: the implementation looked too aggressive for me. Leveraged ETFs, a fragile structure, and a level of volatility I did not want anywhere near the money my family depended on.</span></p><p><span>But the underlying idea stuck.</span></p><p><span>He was not just asking, &#8220;How much money should I put in stocks and bonds?&#8221;</span></p><p><span>He was asking, &#8220;How much risk is each part of the portfolio contributing?&#8221;</span></p><p><span>A traditional 60/40 portfolio looks balanced because 60% of the dollars are in stocks and 40% are in bonds. But dollars are not the same thing as risk. Stocks are volatile enough that a 60/40 portfolio can get something like 85%-90% of its total risk from equities. </span><a href="https://www.aqr.com/insights/perspectives/risk-parity-is-even-better-than-we-thought"><span>AQR puts the figure at 85% or more</span></a><span>, and Bridgewater&#8217;s paper makes the same basic point about conventional portfolios at roughly 90%.</span></p><p><span>So the stock side does not merely drive &#8220;most&#8221; of the ride. It dominates it. You can call that balanced by dollars. It is not really balanced by risk.</span></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!aqen!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!aqen!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 424w, https://substackcdn.com/image/fetch/$s_!aqen!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 848w, https://substackcdn.com/image/fetch/$s_!aqen!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!aqen!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!aqen!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg" width="1200" height="760" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/b662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:760,&quot;width&quot;:1200,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:89937,&quot;alt&quot;:&quot;Chart comparing a 60/40 portfolio by dollars invested with estimated risk contribution, showing stocks as 60% of dollars but roughly 90% of total portfolio risk.&quot;,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://caseyschorr.substack.com/i/215286544?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="Chart comparing a 60/40 portfolio by dollars invested with estimated risk contribution, showing stocks as 60% of dollars but roughly 90% of total portfolio risk." title="Chart comparing a 60/40 portfolio by dollars invested with estimated risk contribution, showing stocks as 60% of dollars but roughly 90% of total portfolio risk." srcset="https://substackcdn.com/image/fetch/$s_!aqen!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 424w, https://substackcdn.com/image/fetch/$s_!aqen!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 848w, https://substackcdn.com/image/fetch/$s_!aqen!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!aqen!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb662098c-6aa0-4fbc-a36e-1c09bad3049d_1200x760.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><span>I wanted to know whether </span><a href="https://www.caseyschorr.com/p/risk-parity"><span>risk parity</span></a><span> was just a clever forum idea or something more durable. Eventually I found Bridgewater&#8217;s paper, </span><a href="https://www.semanticscholar.org/paper/Risk-Parity-is-About-Balance/5e7aea8f829d1da47aa2abc7c38daf5a2d6e34c6"><span>Risk parity is about balance</span></a><span>.</span></p><p><span>Bridgewater was not writing about a clever trade. It was describing a portfolio construction framework with a real institutional history. Pensions, endowments, AQR, PanAgora: serious investors had spent decades working on this problem.</span></p><p><span>That did not mean it belonged in my portfolio. But it changed the question. I was no longer asking, &#8220;Are people on the internet taking too much risk?&#8221; I was asking, &#8220;Can an institutional idea like this be adapted carefully enough to support a family portfolio?&#8221;</span></p><p><span>The basic idea is to build around economic environments instead of ticker symbols:</span></p><ul><li><p><span>Stocks tend to do well when growth is strong.</span></p></li><li><p><span>Bonds can help when growth slows or investors are looking for safety.</span></p></li><li><p><span>Trend-following funds are the wildcard: they try to ride big shifts from one environment to another, whether those moves are up or down.</span></p></li></ul><p><span>The 2022 inflation shock showed me why trend following mattered. In a year when stocks and bonds both struggled, </span><a href="https://www.aqr.com/Insights/Research/White-Papers/Trend-Following-Why-Now-A-Macro-Perspective"><span>AQR noted</span></a><span> the SG Trend Index was up 36% through September while a global 60/40 portfolio was down 20%. It was doing something meaningfully different from the stock-and-bond portfolio I already understood.</span></p><p><span>The goal is not to predict the next environment. It is to own pieces that can work for different reasons, at different times.</span></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!EOmb!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!EOmb!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 424w, https://substackcdn.com/image/fetch/$s_!EOmb!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 848w, https://substackcdn.com/image/fetch/$s_!EOmb!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!EOmb!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!EOmb!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg" width="1200" height="760" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:760,&quot;width&quot;:1200,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:103307,&quot;alt&quot;:&quot;Chart showing stocks, bonds, and trend following as three return streams sized so each contributes about one-third of total portfolio risk.&quot;,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://caseyschorr.substack.com/i/215286544?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="Chart showing stocks, bonds, and trend following as three return streams sized so each contributes about one-third of total portfolio risk." title="Chart showing stocks, bonds, and trend following as three return streams sized so each contributes about one-third of total portfolio risk." srcset="https://substackcdn.com/image/fetch/$s_!EOmb!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 424w, https://substackcdn.com/image/fetch/$s_!EOmb!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 848w, https://substackcdn.com/image/fetch/$s_!EOmb!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!EOmb!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2af77d02-aa93-4a3a-ae60-e6bba2a1e498_1200x760.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><span>The biggest danger is not simply a bad year. It is a bad sequence: large losses early, withdrawals coming out anyway, and not enough time for the portfolio to recover. That is what retirement planners call </span><a href="https://www.caseyschorr.com/p/sequence-of-returns-risk"><span>sequence-of-returns risk</span></a><span>.</span></p><p><span>If a portfolio could make the worst drawdowns less severe, it might support a higher withdrawal rate than a traditional stock-heavy portfolio, even if the long-run returns were not dramatically higher.</span></p><p><span>That was what I needed to test.</span></p><h2><span>A different kind of leverage</span></h2><p><span>A traditional stock-and-bond portfolio gives you one blunt lever.</span></p><p><span>If you want less risk, you hold fewer stocks. But then expected returns fall, and the amount you can safely withdraw falls with them.</span></p><p><span>If you want more return, you hold more stocks. But then drawdowns get bigger, and the portfolio becomes more vulnerable if the bad years show up right after you start withdrawing.</span></p><p><span>Either way, the real constraint is not just average return. It is the relationship between return, volatility, drawdowns, and withdrawals.</span></p><p><span>Risk parity offers another path.</span></p><p><span>First, build a portfolio that is more balanced across economic conditions. If that base is genuinely smoother, modest leverage can bring return potential back up.</span></p><p><span>That sounds dangerous if you hear only the word &#8220;leverage.&#8221; It can be dangerous. Leverage can turn a mistake into a disaster.</span></p><p><span>But applying leverage to a diversified base is different from making a stock-heavy portfolio even more stock-heavy. You are trying to amplify something steadier, not concentrate harder into one source of risk.</span></p><p><span>In my case, the tool that made this possible was Treasury futures.</span></p><p><span>Treasury futures are not for beginners. They create real leverage, require collateral, and can produce uncomfortable losses even when the overall portfolio is behaving as intended.</span></p><p><span>But they also let a portfolio get meaningful Treasury exposure without tying up all the capital required to buy bonds outright. When I checked the margin requirement in my own taxable Interactive Brokers account, about $15,000 of required margin could control roughly $1 million of notional exposure.</span></p><p><span>The exact figure is less important than the order of magnitude: a relatively small amount of collateral can control a much larger position. That is the appeal, and also the danger.</span></p><p><span>Used carefully, Treasury futures make room for the other pieces of the system: equities and trend following.</span></p><p><span>Interesting was not enough. I needed to know whether the system was robust enough to trust with my family&#8217;s financial foundation.</span></p><h2><span>I tested it before I trusted it</span></h2><p><span>My wife asked the important questions:</span></p><blockquote><p><span>Why is this not what everyone does?</span></p><p><span>What if you are wrong?</span></p></blockquote><p><span>I also had to ask whether I was seeing something real or just turning the portfolio into another problem to solve.</span></p><p><span>So we booked a consultation with Rick Ferri, a fee-only advisor and longtime Boglehead. I expected him to dismiss the whole thing as unnecessary complexity.</span></p><p><span>He did not. After looking at our financial situation and my explanation of risk parity, he told us he had explored strategies like this when he was younger. The logic could work. The tradeoff was that it would be more complex to manage than a simple three-fund portfolio.</span></p><p><span>That did not settle the question for either of us. But it moved the idea one step away from &#8220;this is reckless&#8221; and closer to &#8220;this might be real, if I could build and manage it carefully.&#8221;</span></p><p><span>From there I treated the portfolio like a system I had to build and test: sanity check, emotional test, full scale.</span></p><p><span>First came the model.</span></p><p><span>I rebuilt backtests, compared traditional allocations to risk parity-style portfolios, and paid special attention to bad-luck scenarios. I cared less about the average case and more about the bad-luck case: what happens if the first decade is ugly?</span></p><p><span>In my modeling, the important difference was not that risk parity magically crushed everything in good times. It was that the bad cases looked less bad, and not by a rounding error.</span></p><p><span>In one Monte Carlo setup in Portfolio Visualizer, I looked at the 10th-percentile outcome: the bad-luck version where returns show up in an ugly order. In that scenario, the modeled withdrawal rate moved from roughly 3.7% for a traditional 60/40 to roughly 5.5% for the risk parity-style version.</span></p><p><span>I would not treat those numbers as gospel, but the gap was large enough to matter for the question I actually cared about: how much could we withdraw without letting one bad sequence break the plan?</span></p><p><span>Then came the emotional test.</span></p><p><span>A spreadsheet was one kind of test. Watching real money move in real time was another. For the emotional test, I worked up to about $1 million, adding gradually and watching how the pieces behaved together.</span></p><p><span>The portfolio I settled into included:</span></p><ul><li><p><span>US equities, including large cap and small cap value exposure.</span></p></li><li><p><span>International equities, including a small-cap emerging markets tilt.</span></p></li><li><p><span>Treasury futures for leveraged bond exposure.</span></p></li><li><p><span>Commodity trend-following funds as a third major return stream.</span></p></li><li><p><span>A 10% cash reserve as an operational guardrail.</span></p></li></ul><p><span>I kept iterating. I looked for the conditions that would make the whole thing fail. Over time, the question shifted from whether the system was perfect to whether I understood it well enough to live with it.</span></p><p><span>Eventually, I scaled the strategy across my taxable portfolio.</span></p><p><span>I did not have certainty. I had enough understanding to choose it over the standard answer.</span></p><h2><span>What it feels like to live with</span></h2><p><span>In late 2024, I left the company that bought my startup. Since then, the portfolio has not been an abstract planning problem. It has been part of how our household actually works.</span></p><p><span>I have no earned income right now, so this is not theory.</span></p><p><span>That changes my relationship to every red number.</span></p><p><span>The strange thing about a diversified portfolio is that something almost always looks wrong.</span></p><p><span>When stocks are ripping higher, the diversifiers can look like dead weight. When stocks fall, Treasury futures or trend-following funds may be the only reason the whole thing is not worse. When trend-following funds are struggling, it is easy to wonder why you own them at all.</span></p><p><span>The system only makes sense at the portfolio level, but brokerage screens are designed to make you stare at individual positions.</span></p><p><span>That is psychologically hard.</span></p><p><span>During the spring 2025 tariff-driven market selloff, my portfolio did what I hoped it would do. The S&amp;P 500 fell </span><a href="https://www.spglobal.com/market-intelligence/en/news-insights/articles/2025/6/bad-breadth-concerns-rise-as-sp-500-set-to-recover-tarifftriggered-losses-90308072"><span>about 19% from its February high to its April low</span></a><span>. In my own tracking, my rough 60/40 benchmark was down about 13% peak to trough. My portfolio was down roughly 8%.</span></p><p><span>The difference was real. It still did not feel good.</span></p><p><span>Parts of the portfolio were still bleeding. Individual positions were down enough to set off every alarm in my head. Sell the losers. Move into what was working. Fix it.</span></p><p><span>But the whole point of the system is that different pieces take turns looking bad.</span></p><p><span>That is not a bug. It is the feature.</span></p><p><span>Instead of tinkering with the allocation, I built a tax-loss harvesting spreadsheet and used the losses that were already there. Later, those losses gave me room to rebalance out of positions that had run up without taking the full tax hit.</span></p><p><span>The portfolio gave me something better than a prediction. It gave me a rule-based way to act without pretending I knew what the market would do next.</span></p><p><span>I am not checking it all day. I am not trying to guess what the Fed will do. I am not waiting for someone else&#8217;s forecast to tell me whether my family gets to live the way we want to live.</span></p><p><span>I understand what each piece is supposed to do, and I can evaluate the system against that job.</span></p><h2><span>The question is still freedom</span></h2><p><span>The obvious question is whether this works for the next 50 years.</span></p><p><span>I do not know.</span></p><p><span>No backtest can prove that. No advisor can guarantee it. No research paper can remove the fact that I am testing this in real time, with real money, under real life constraints.</span></p><p><span>But I know why I am doing it.</span></p><p><span>The standard advice was safe, but it asked me to accept a smaller life than the one the exit was supposed to make possible. A very conservative withdrawal rate may protect the pile of money, but it can also defeat the reason the money matters.</span></p><p><span>That is why the withdrawal-rate question is not abstract. A 3% life and a 6% life are not the same life. One is safety. The other, if the system can actually support it, is freedom.</span></p><p><span>For me, the question is not &#8220;How do I maximize returns?&#8221;</span></p><p><span>What I actually want to know is:</span></p><ul><li><p><span>Can I build a financial system stable enough to let me stop organizing my life around earning?</span></p></li><li><p><span>Can it create room for family, health, skiing, building, writing, and a slower kind of ambition?</span></p></li><li><p><span>Can it turn the exit from a number on a screen into actual freedom?</span></p></li></ul><p><span>I am writing this because I wish someone had handed me a way to think about this the day the wire hit.</span></p><p><span>I rarely saw this stage described plainly: somewhere between still working and retired, managing a finite sum, trying to buy back time without pretending money is the point.</span></p><p><span>That is why risk parity became more than an investment framework for me. It became one part of a personal lab: post-exit money, AI-native building, and the search for a life with more freedom and less operational drag.</span></p><p><span>The day the wire hit, I thought the hard part was over.</span></p><p><span>It was not.</span></p><p><span>The exit gave me the raw material. The portfolio is one of the systems I am building to turn that raw material into a life.</span></p><p><span>And that is the experiment I want to keep writing from.</span></p>]]></content:encoded></item><item><title><![CDATA[Risk parity]]></title><description><![CDATA[Risk parity asks whether a portfolio is balanced by the risks it carries, not just by the dollars it holds.]]></description><link>https://www.caseyschorr.com/p/risk-parity</link><guid isPermaLink="false">https://www.caseyschorr.com/p/risk-parity</guid><dc:creator><![CDATA[Casey Schorr]]></dc:creator><pubDate>Thu, 28 May 2026 22:06:00 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/70573f38-eec7-4d28-8cc4-8a41b368fbc8_1200x630.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><span>Risk parity is a way to build a portfolio around balanced risk instead of balanced dollars.</span></p><p><span>A portfolio can look diversified because the dollars are spread across several assets. But dollars are not the same thing as risk.</span></p><p><span>A normal portfolio might put 60% of its money in stocks and 40% in bonds. By dollars, that looks balanced. But stocks tend to be more volatile than high-quality bonds, so the stock side can still drive most of the portfolio&#8217;s actual risk. The portfolio owns bonds, but the ride can still be mostly an equity ride.</span></p><p><span>Risk parity starts with a different question:</span></p><blockquote><p><span>How much risk is each part of the portfolio contributing?</span></p></blockquote><p><span>The dollar split is not the problem. Dollar weights can hide where the real risk is coming from.</span></p><h2><span>Balanced dollars vs. balanced risk</span></h2><p><span>A normal allocation asks, &#8220;How many dollars should go into each asset?&#8221;</span></p><p><span>Risk parity asks, &#8220;How much risk should each asset contribute?&#8221;</span></p><p><span>Those are not the same question. The dollar weights tell you how the capital is divided. They do not tell you which part of the portfolio is most likely to drive the gains, losses, and stress.</span></p><p><span>Risk parity tries to look past the surface allocation to see what is actually driving the portfolio&#8217;s behavior, then balance the risk so no single return stream dominates the portfolio.</span></p><h2><span>Why it matters</span></h2><p><span>Risk parity became interesting to me after I sold a business, when the portfolio had to do more than grow in the background.</span></p><p><span>If you are still earning, saving, and investing for some far-off future, an equity-heavy portfolio can make a lot of sense. You have income coming in. You can keep buying through drawdowns. Time is doing a lot of the repair work.</span></p><p><span>But if a sale, windfall, concentrated equity payout, or other once-in-a-lifetime liquidity event is supposed to buy real freedom now, the question changes.</span></p><p><span>The default answer is usually some version of keeping the stock-heavy portfolio, adding more private investments, hiring an adviser, or accepting a very low withdrawal rate. There may be good reasons for any of those. But they can still leave the portfolio depending heavily on one underlying bet: equity-like risk being rewarded soon enough, smoothly enough, and in the right sequence.</span></p><p><span>Risk parity matters because it points at that underlying bet directly. It asks whether the portfolio is built around one dominant source of risk, or whether it owns return streams with different reasons for working at different times.</span></p><p><span>If different return streams help at different times, the portfolio can be less vulnerable to permanent damage from a bad sequence of returns.</span></p><p><span>Drawdowns matter because the path matters. A portfolio with the highest expected return is not always the portfolio that creates the most usable freedom. If the bad years arrive early, and money is coming out at the same time, the damage can be hard to recover from.</span></p><p><span>That does not mean risk parity is simply giving up upside for safety. Once money is coming out, the smoother path can matter more than the highest peak-year upside, because avoiding deep early holes makes a huge difference in how the portfolio compounds.</span></p><p><span>This is why risk parity kept pulling me in. It felt like a structural improvement to portfolio design, not another attempt to outsmart the market or find better investments.</span></p><h2><span>How I use the term</span></h2><p><span>When I say risk parity, I mean a portfolio construction framework, not a single fund, formula, or product someone can copy.</span></p><p><span>For me, that framework is built around four ideas:</span></p><ul><li><p><span>Balance risk, not dollars.</span></p></li><li><p><span>Own return streams with different reasons for working at different times.</span></p></li><li><p><span>Size each part by how much risk it contributes to the whole portfolio.</span></p></li><li><p><span>Judge the portfolio by the job it was built to do, not just by headline annual returns.</span></p></li></ul><p><span>In my own post-exit portfolio, that framework means equities for growth, Treasuries for defensive ballast, trend following as a distinct return stream, and rules for managing the system when parts of it look uncomfortable.</span></p><h2><span>Leverage</span></h2><p><span>Risk parity often gives lower-volatility assets, like Treasuries, a larger role than they would get in a dollar-weighted portfolio. In my own system, that means using leverage, because Treasuries do not carry enough risk on their own to stand beside equities as an equal risk contributor.</span></p><p><span>Leverage is the part people tend to notice first.</span></p><p><span>But leverage is not the defining feature. Risk balancing is. In my system, leverage is a tool for scaling that more balanced base to the level of risk and return the job requires.</span></p><p><span>It is there because the Treasuries are there to do a job, not to turn the whole portfolio into a bigger equity bet.</span></p><h2><span>What risk parity is not</span></h2><p><span>Risk parity is not a single portfolio, fund, or set of tickers. Two investors can both use risk parity logic and end up with very different implementations.</span></p><p><span>It is also not the same as &#8220;own a lot of things.&#8221; A portfolio can own many funds and still depend mostly on the same equity-like risk underneath. Diversification only matters if the return streams behave differently when the world changes.</span></p><p><span>Risk parity depends on return streams behaving differently enough to matter. That is not guaranteed. The relationships between return streams can change, and streams that looked different in normal times can move together when stress is high.</span></p><p><span>It is also not a promise that the portfolio will always feel calm. A risk parity-style portfolio can be uncomfortable even when the design is working. Some part of it almost always looks wrong. If stocks are leading, diversifiers may look like dead weight. If stocks are falling, the defensive pieces may be doing their job, but the account can still be down. If inflation is the problem, bonds may be painful at exactly the moment they were supposed to feel safe.</span></p><p><span>Risk parity does not need every piece to work at once. It tries to avoid depending on any one piece working all the time.</span></p><h2><span>The real question</span></h2><p><span>For me, risk parity comes back to one question:</span></p><p><span>Can my portfolio create more freedom for my family without depending too much on one return stream or needing the good years to arrive at the right time?</span></p><p><span>Risk parity becomes useful to me not as a label, but as a way to ask whether the portfolio is actually built for the job I need it to do.</span></p>]]></content:encoded></item></channel></rss>