<?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[Carry On Capital]]></title><description><![CDATA[Carry On Capital]]></description><link>https://carryon.capital</link><image><url>https://substackcdn.com/image/fetch/$s_!gQsq!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F391754ee-24d8-42bf-ad31-ad16003bd60c_144x144.png</url><title>Carry On Capital</title><link>https://carryon.capital</link></image><generator>Substack</generator><lastBuildDate>Fri, 17 Apr 2026 12:12:43 GMT</lastBuildDate><atom:link href="https://carryon.capital/feed" rel="self" type="application/rss+xml"/><copyright><![CDATA[Mark Lewis]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[carryoncapital@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[carryoncapital@substack.com]]></itunes:email><itunes:name><![CDATA[Mark Lewis]]></itunes:name></itunes:owner><itunes:author><![CDATA[Mark Lewis]]></itunes:author><googleplay:owner><![CDATA[carryoncapital@substack.com]]></googleplay:owner><googleplay:email><![CDATA[carryoncapital@substack.com]]></googleplay:email><googleplay:author><![CDATA[Mark Lewis]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[The Safe Bet That Wasn't]]></title><description><![CDATA[Computer Science, Unemployment, and What to Actually Tell Kids About College]]></description><link>https://carryon.capital/p/the-safe-bet-that-wasnt</link><guid isPermaLink="false">https://carryon.capital/p/the-safe-bet-that-wasnt</guid><dc:creator><![CDATA[Mark Lewis]]></dc:creator><pubDate>Thu, 26 Mar 2026 19:25:17 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!rPcM!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!rPcM!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!rPcM!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png 424w, https://substackcdn.com/image/fetch/$s_!rPcM!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png 848w, https://substackcdn.com/image/fetch/$s_!rPcM!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!rPcM!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!rPcM!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png" width="1456" height="813" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/c4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:813,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:8489981,&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://carryon.capital/i/191890882?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!rPcM!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png 424w, https://substackcdn.com/image/fetch/$s_!rPcM!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png 848w, https://substackcdn.com/image/fetch/$s_!rPcM!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!rPcM!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc4a2ea5a-09b0-43c2-8d20-b8d4965e593f_2752x1536.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 role="img" 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><title></title><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></p><p>For the better part of two decades, the advice was practically unanimous. Guidance counselors said it. Parents said it. Reddit said it. The message was simple: study computer science, get a six-figure job, live happily ever after. It was the closest thing America had to a guaranteed career path.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://carryon.capital/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Carry On Capital! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>That guarantee has expired.</p><h2><strong>The Numbers Nobody Wants to Talk About</strong></h2><p>Here&#8217;s the stat that should make every parent rethink their assumptions: the unemployment rate for recent computer science graduates has hit 6.1%. Computer engineering graduates? 7.5%. To put that in perspective, fine arts graduates -- the very people CS majors were told they&#8217;d never want to become -- are now more employed than computer engineers.</p><p>These aren&#8217;t anomalies. They&#8217;re data points from the Federal Reserve Bank of New York, and they paint a picture of an industry undergoing something more fundamental than a cyclical downturn.</p><p>The raw numbers are staggering. Over 127,000 workers at U.S.-based tech companies were laid off in 2025. So far in 2026, another 55,000+ have been cut. According to Indeed&#8217;s 2025 Tech Talent Report, tech job postings have dropped 36% compared to pre-2020 levels. And the roles that are disappearing fastest? Entry-level ones -- precisely the jobs that new graduates need.</p><p>Meanwhile, the supply side has gone in the opposite direction. U.S. universities handed out roughly 110,000 CS bachelor&#8217;s degrees in 2022-2023, about double the number from a decade earlier. We spent years telling every ambitious 18-year-old to study CS, and they listened. Now they&#8217;re all showing up to a party that&#8217;s winding down.</p><h2><strong>The AI Elephant in the Room</strong></h2><p>The factor that makes this different from previous tech downturns is artificial intelligence, and not in the way most people think. AI isn&#8217;t just creating new jobs in tech while eliminating old ones. It&#8217;s fundamentally compressing the value of the skill that CS graduates were trained to sell: writing code.</p><p>A Stanford Digital Economy Study found that by July 2025, employment for software developers aged 22 to 25 declined nearly 20% from its peak in late 2022. But here&#8217;s the twist: employment for developers aged 35 to 49 actually <em>increased</em> by 9%. The industry isn&#8217;t dying. It&#8217;s hollowing out from the bottom.</p><p>The reason is straightforward. AI coding tools have gotten good enough that a senior engineer with Claude Code or GitHub Copilot can do work that previously required a team of three or four juniors. One engineer at a large San Francisco tech company told the SF Standard that all of his code is now written by AI: &#8220;I&#8217;m basically a proxy to Claude Code.&#8221; Companies don&#8217;t need fewer software engineers total -- they need fewer <em>beginning</em> software engineers. And those are exactly the people we&#8217;ve been minting by the tens of thousands.</p><p>Even graduates from elite programs aren&#8217;t immune. Data from SignalFire shows that the share of graduates from MIT, Stanford, Carnegie Mellon, and UC Berkeley employed as engineers at major tech companies dropped from 25% in 2022 to just 11-12% recently -- a decline of more than 50%. If a Stanford CS degree can&#8217;t reliably get you into Big Tech anymore, what chance does a degree from a mid-tier state school have?</p><p>The individual stories are brutal. Manasi Mishra, a CS major from Purdue, received exactly one interview offer after a year of searching -- from Chipotle. Zach Taylor, an Oregon State graduate, submitted over 5,700 applications with no success. These aren&#8217;t lazy people or weak students. They did everything they were told to do. The system just changed the rules while they were playing the game.</p><h2><strong>The Enrollment Cliff Is Already Here</strong></h2><p>The market is starting to send signals back to prospective students, and they&#8217;re listening. For the first time since the early 2010s, total enrollment in traditional CS undergraduate programs has dropped by 6%. The University of California system is reporting noticeable declines in CS majors even as overall university enrollment rose by 2%.</p><p>This is a meaningful shift. For years, CS departments couldn&#8217;t build lecture halls fast enough. Now the tide is turning, not because students suddenly lost interest in technology, but because the career calculus no longer adds up the way it used to. When 55% of hiring managers expect more layoffs and 44% say AI will be the top driver, students and their families are paying attention.</p><h2><strong>So What Do You Actually Tell a Teenager?</strong></h2><p>This is where the conversation gets uncomfortable, because the honest answer isn&#8217;t as clean as &#8220;just major in CS&#8221; used to be. But here&#8217;s my best attempt at advice that accounts for the world as it actually is, not as it was five years ago.</p><p><strong>First, stop thinking in terms of &#8220;safe&#8221; majors.</strong> The entire concept of a safe major is a relic of a more stable economy. The same forces that disrupted CS -- AI automation, globalization, rapid industry shifts -- are coming for every field eventually. The goal isn&#8217;t to find the one discipline that AI will never touch. The goal is to become the kind of person who can adapt when your field inevitably changes.</p><p><strong>Second, domain expertise is the new moat.</strong> The graduates who will thrive in an AI-saturated economy aren&#8217;t the ones who can write the best code. They&#8217;re the ones who deeply understand a specific problem domain -- healthcare, energy, logistics, finance, education -- and can use AI tools to solve problems within it. A nursing student who understands AI-assisted diagnostics is more valuable than a CS graduate who can sort algorithms on a whiteboard. An environmental scientist who can build data pipelines for climate modeling has a career that no chatbot is going to replace.</p><p><strong>Third, the trades and physical-world careers deserve a serious look.</strong> Electricians, plumbers, HVAC technicians, construction managers -- these are careers with strong demand, rising wages, no student debt, and near-zero risk of AI displacement. The largest areas of total job creation right now are in care, construction, logistics, and education. These roles combine people skills with hands-on work that simply cannot be automated away. The cultural bias against trade careers has always been irrational, and the current moment makes it look even more absurd.</p><p><strong>Fourth, if a student genuinely loves CS, they should still study it -- but differently.</strong> The degree itself still has long-term value. NACE data showed CS topped the starting salary list at $88,907 for the Class of 2024. Software engineering roles overall are projected to grow by 17% through 2033. The Bureau of Labor Statistics projects 317,700 annual openings in computer and IT occupations through 2034. The field isn&#8217;t dead; it&#8217;s restructuring. But students need to graduate with more than a transcript. They need a portfolio of real projects, experience with AI tools, and ideally a secondary area of expertise. The formula has changed from &#8220;degree equals job&#8221; to &#8220;degree plus portfolio plus real experience equals job.&#8221; Students who treat their CS education as a foundation rather than a finish line will be fine. Students who expect the degree alone to open doors are in for a painful surprise.</p><p><strong>Fifth, consider the interdisciplinary path.</strong> Pair a major in something you find genuinely interesting -- biology, political science, economics, design -- with a minor or certificate in data science, cybersecurity, or applied AI. This combination produces exactly the kind of hybrid thinker that employers are scrambling to find. The fastest-growing roles include AI and machine learning specialists, sustainability specialists, and business intelligence analysts. Notice how each of those combines technical skills with deep knowledge of a specific domain.</p><h2><strong>The Bigger Picture</strong></h2><p>What&#8217;s happening in computer science is a preview of what&#8217;s coming for many white-collar professions. Anthropic CEO Dario Amodei has warned that AI could eliminate half of all entry-level white-collar jobs within one to five years. Geoffrey Hinton, the so-called godfather of AI, predicts that in a few years, AI will be able to handle software engineering tasks that currently take a month. Whether those predictions are precisely right or somewhat exaggerated, the direction is clear.</p><p>The old playbook -- pick the &#8220;right&#8221; major, get the degree, collect the job offer -- is breaking down. The new playbook is messier and less reassuring, but it&#8217;s also more honest. It says: develop real skills, not just credentials. Combine disciplines rather than siloing into one. Stay curious about how AI is reshaping your field instead of ignoring it. Build things that demonstrate what you can do, not just what you studied. And for the love of everything, don&#8217;t pick a major solely because someone told you it was &#8220;safe.&#8221;</p><p>The safest bet in an era of rapid change isn&#8217;t picking the right field. It&#8217;s becoming the kind of person who can learn a new one.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://carryon.capital/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Carry On Capital! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[The SaaS Model's Real Existential Threat Is Your Weekend]]></title><description><![CDATA[Contracts, not products, are the only thing keeping SaaS companies alive]]></description><link>https://carryon.capital/p/the-saas-models-real-existential</link><guid isPermaLink="false">https://carryon.capital/p/the-saas-models-real-existential</guid><dc:creator><![CDATA[Mark Lewis]]></dc:creator><pubDate>Tue, 20 Jan 2026 20:43:41 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!2LQj!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!2LQj!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!2LQj!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png 424w, https://substackcdn.com/image/fetch/$s_!2LQj!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png 848w, https://substackcdn.com/image/fetch/$s_!2LQj!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png 1272w, https://substackcdn.com/image/fetch/$s_!2LQj!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!2LQj!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png" width="1456" height="971" 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srcset="https://substackcdn.com/image/fetch/$s_!2LQj!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png 424w, https://substackcdn.com/image/fetch/$s_!2LQj!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png 848w, https://substackcdn.com/image/fetch/$s_!2LQj!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.png 1272w, https://substackcdn.com/image/fetch/$s_!2LQj!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9b7430cd-5822-4a5f-bdda-56da39ced6d2_1536x1024.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 role="img" 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><title></title><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>Dave Clark, the former CEO of Worldwide Consumer at Amazon, built a custom CRM in a night and a morning for his new startup.</p><p>Not a prototype. Not a demo. A real system that actually fits how his company sells.</p><p>He tried the off-the-shelf option first. Too many fields he did not need. Missing the ones he did. A pipeline that did not match reality.</p><p>His verdict: &#8220;I spent more time fighting the tool than using it.&#8221;</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!6MdI!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!6MdI!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 424w, https://substackcdn.com/image/fetch/$s_!6MdI!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 848w, https://substackcdn.com/image/fetch/$s_!6MdI!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 1272w, https://substackcdn.com/image/fetch/$s_!6MdI!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!6MdI!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png" width="1004" height="1324" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1324,&quot;width&quot;:1004,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:296716,&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;:false,&quot;internalRedirect&quot;:&quot;https://carryon.capital/i/185225472?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!6MdI!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 424w, https://substackcdn.com/image/fetch/$s_!6MdI!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 848w, https://substackcdn.com/image/fetch/$s_!6MdI!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 1272w, https://substackcdn.com/image/fetch/$s_!6MdI!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32abd957-c9cf-4c7b-a4d7-d2ec06379f5e_1004x1324.png 1456w" sizes="100vw"></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 role="img" 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><title></title><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></p><p>So he stopped fighting it and built exactly what he needed.</p><p>That should scare every SaaS company charging $50 to $500 per seat per month.</p><div><hr></div><h3><strong>The SaaS bargain is breaking</strong></h3><p>The SaaS model rests on a simple trade. It is cheaper to pay us every month than to build this yourself.</p><p>That math worked when &#8220;build it yourself&#8221; meant hiring engineers, provisioning infrastructure, coordinating teams, and maintaining software for years.</p><p>That math is collapsing.</p><p>Over the past year, I have saved my company tens of thousands of dollars in SaaS fees by doing exactly what Dave did. I replaced internal tools that used to justify six-figure annual contracts with custom software built in days.</p><p>Not because I suddenly became a better developer. Because development itself fundamentally changed.</p><div><hr></div><h3><strong>The real product was coordination</strong></h3><p>SaaS companies did not really sell software. They sold relief from coordination pain.</p><p>You did not buy Salesforce for a database. You bought it to avoid months of requirements gathering, vendor evaluations, implementation plans, and training sessions.</p><p>Dave put it perfectly: &#8220;Most friction is not technical. It is structural. Waiting on vendors. Scheduling demos. Debating requirements in meetings that create more meetings.&#8221;</p><p>When AI removes that friction, what remains?</p><p>A monthly bill for features you do not use and workflows that do not match how you actually operate.</p><div><hr></div><h3><strong>The bloat problem</strong></h3><p>Every successful SaaS product follows the same arc.</p><p>They start focused and useful. Then they chase enterprise checklists. Features get added to satisfy procurement, not users. Five years later, you are paying for 200 features to use 12.</p><p>Custom tools have the opposite profile. They do exactly what you need and nothing more.</p><p>That used to be a weakness.</p><p>Now it is the advantage.</p><div><hr></div><h3><strong>The open source middle path</strong></h3><p>You do not even have to start from scratch.</p><p>Open source alternatives exist for nearly every SaaS category. CRMs, project management, analytics, help desks. The code is free. The problem was always implementation and customization.</p><p>That problem just got solved.</p><p>Take an open source CRM. Fork it. Strip out what you do not need. Add the fields that match your actual sales process. Deploy it on your own infrastructure. A year ago, that was a multi-month project requiring specialized talent. Now it is a weekend with AI assistance.</p><p>You get the foundation someone else built, customized exactly to your workflow, with no per-seat fees and no vendor lock-in.</p><p>The SaaS pitch was always &#8220;why build when you can buy?&#8221; Open source offered a counter: &#8220;why rent when you can own?&#8221; But ownership came with complexity that made the rental worthwhile for most companies.</p><p>AI collapses that complexity gap. The open source option just became viable for companies that never would have considered it.</p><div><hr></div><h3><strong>Who is most at risk</strong></h3><p>Not all SaaS categories are equally exposed.</p><p>The most vulnerable: horizontal tools with generic workflows like CRMs, project management, and basic analytics. High per-seat pricing with low switching friction. Products where the interface is the value, not the data or the network. Tools where customers can export their data and rebuild the experience on their own stack.</p><p>If your customer is paying $50,000 a year and can recreate 80 percent of your product in a long weekend, you are not selling software. You are renting time until replacement.</p><div><hr></div><h3><strong>Who survives</strong></h3><p>Some products still have real moats.</p><p>Network-driven tools where value increases with adoption. Deeply embedded systems where replacement touches everything. Highly regulated workflows where homegrown software creates compliance risk. Products where the proprietary model is the product, not the UI wrapped around it.</p><p>These companies are not competing with weekends.</p><p>Everyone else is.</p><div><hr></div><h3><strong>The venture math problem</strong></h3><p>Most SaaS companies are still priced and operated on growth-era assumptions.</p><p>High acquisition spend justified by long-term retention. Valuations built on 95 percent net revenue retention. Switching costs assumed to be structural.</p><p>Those assumptions are eroding fast.</p><p>If a customer can rebuild your core functionality in 72 hours, your churn model is already wrong. And if you raised at a double-digit revenue multiple assuming it would never happen, no amount of &#8220;AI features&#8221; will save you.</p><div><hr></div><h3><strong>The only thing holding this together</strong></h3><p>Right now, the SaaS industry is not being sustained by product value. It is being sustained by friction.</p><p>Switching costs. Multi-year contract lock-ins. The pain of migrating data. The institutional inertia of &#8220;we already use this.&#8221;</p><p>These are not moats. They are delays.</p><p>Every contract that expires is a decision point. Every renewal is now a question that did not used to get asked: do we actually need to keep paying for this, or could we just build it?</p><p>SaaS companies know this. It is why sales teams push so hard for multi-year commitments. It is why auto-renewal clauses exist. It is why cancellation flows are designed to be as painful as possible.</p><p>The product is no longer the lock-in. The contract is.</p><p>That works until it does not. And when enough companies start doing the math at renewal time, the churn will not be gradual. It will cascade.</p><div><hr></div><h3><strong>What this means for buyers</strong></h3><p>Before you sign your next annual contract, ask one question:</p><p>Could we build 80 percent of this in a weekend?</p><p>If the answer is yes, you probably should.</p><p>The SaaS industry spent 15 years convincing companies that building software was too hard to attempt.</p><p>That was true.</p><p>It is becoming less true every month.</p><p>I am not renewing three contracts this quarter. The replacements took less time to build than the sales calls took to schedule.</p>]]></content:encoded></item><item><title><![CDATA[The Trillion-Dollar Depreciation Gamble]]></title><description><![CDATA[How Debt-Financed AI Infrastructure, GPU Collateral, and Aggressive Accounting Collide]]></description><link>https://carryon.capital/p/the-trillion-dollar-depreciation</link><guid isPermaLink="false">https://carryon.capital/p/the-trillion-dollar-depreciation</guid><dc:creator><![CDATA[Mark Lewis]]></dc:creator><pubDate>Wed, 17 Dec 2025 15:54:46 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!yKn-!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!yKn-!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!yKn-!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png 424w, https://substackcdn.com/image/fetch/$s_!yKn-!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png 848w, https://substackcdn.com/image/fetch/$s_!yKn-!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!yKn-!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!yKn-!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png" width="1456" height="813" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:813,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:963481,&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://carryon.capital/i/181394999?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!yKn-!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png 424w, https://substackcdn.com/image/fetch/$s_!yKn-!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png 848w, https://substackcdn.com/image/fetch/$s_!yKn-!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.png 1272w, https://substackcdn.com/image/fetch/$s_!yKn-!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1efbcde6-f720-45da-ba11-fc552c00cfd8_2752x1536.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 role="img" 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><title></title><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></p><p>Michael Burry&#8217;s November 2025 accusation that Big Tech is perpetrating &#8220;one of the more common frauds of the modern era&#8221; through server depreciation manipulation has collided with an even more concerning development: the emergence of a $125+ billion debt-financed AI infrastructure boom that makes the telecom bubble&#8217;s financing arrangements look conservative by comparison.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://carryon.capital/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Carry On Capital! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>This analysis examines the intersection of three critical trends: hyperscaler depreciation schedule extensions that have added $13+ billion in artificial annual earnings, a surge in GPU-collateralized debt financing that now exceeds $20 billion, and Oracle&#8217;s unprecedented $108 billion debt load as the company races to fulfill a $300 billion contract with an unprofitable customer (OpenAI). The implications extend beyond individual company risk to systemic concerns about asset-backed securities, private credit markets, and the fundamental economics of AI infrastructure.</p><h1><strong>Part I: The Depreciation Manipulation Case</strong></h1><h2><strong>What the Hyperscalers Actually Changed</strong></h2><p>The depreciation schedule extensions are documented fact. Between 2020 and 2025, all four major hyperscalers systematically extended server useful lives from industry-standard 3-4 years to 5-6 years, generating $13+ billion in cumulative annual earnings benefits.</p><p><strong>Microsoft</strong> moved first in July 2020, extending server lives from 3 to 4 years, then jumped to 6 years in July 2022. The FY2023 impact: $3.7 billion in additional operating income. Microsoft&#8217;s depreciation rate as a percentage of net property and equipment fell from 30-34% in FY2014-2020 to approximately 15% by FY2024.</p><p><strong>Google</strong> followed suit, extending server lives from 3 to 4 years in January 2021, then to 6 years in January 2023. The 2023 change alone reduced depreciation expense by $3.9 billion and boosted net income by $3.0 billion.</p><p><strong>Amazon</strong> pioneered the trend, moving from 3 to 4 years in January 2020, then to 5 years for servers and 6 years for networking equipment by 2022. But Amazon&#8217;s February 2025 decision to reverse the extension for AI-specific servers-shortening useful life from 6 back to 5 years-represents the most significant validation of Burry&#8217;s concerns. The company cited &#8220;increased pace of technology development, particularly in the area of artificial intelligence.&#8221;</p><p><strong>Meta</strong> extended non-AI server lives to 5.5 years in January 2025, projecting $2.9 billion in reduced depreciation expense. Notably, Meta explicitly excluded AI servers from the extension-an implicit acknowledgment that GPU-intensive infrastructure depreciates faster than traditional compute.</p><h2><strong>The Technical Case for Accelerated Obsolescence</strong></h2><p>Burry&#8217;s core argument rests on a fundamental mismatch: NVIDIA releases new GPU architectures annually (accelerated from 18-24 month cycles), yet hyperscalers depreciate these assets over 5-6 years. The technical evidence supports his concern.</p><p>A Google architect&#8217;s assessment found GPUs running at 60-70% utilization-standard for AI workloads-survive only 1-3 years due to thermal and electrical stress. Princeton&#8217;s CITP analysis of Meta&#8217;s Llama 3 training study documented a 9% annualized GPU failure rate, implying 27% failure over three years. H100 GPUs consuming 700 watts per chip create significant thermal degradation that legacy servers never faced.</p><p>Technological obsolescence compounds physical degradation. NVIDIA&#8217;s GB200 &#8220;Blackwell&#8221; chip delivers 4-5x faster inference than the H100. CEO Jensen Huang stated: &#8220;When Blackwell starts shipping in volume, you couldn&#8217;t give Hoppers away.&#8221; NVIDIA declared the A100 series end-of-life in February 2024, merely four years after its 2020 release.</p><h1><strong>Part II: The Debt-Financed Infrastructure Boom</strong></h1><h2><strong>The Scale of AI Infrastructure Debt</strong></h2><p>A UBS report from November 2025 revealed that AI data center and project financing deals surged to $125 billion in 2025, up from just $15 billion in the same period in 2024-an 8x increase. Morgan Stanley estimates private credit markets could supply over half the $1.5 trillion needed for data center buildout through 2028. JP Morgan now estimates AI-linked companies account for 14% of its investment grade index, surpassing U.S. banks as the dominant sector.</p><p>The financing has taken multiple forms: investment-grade corporate bonds (Meta&#8217;s $30 billion, Oracle&#8217;s $18 billion), private credit facilities (Meta&#8217;s $29 billion deal with PIMCO and Blue Owl), GPU-collateralized debt (CoreWeave&#8217;s $9.9 billion), and an emerging asset-backed securities market that BofA estimates could add $50-60 billion in supply in 2026.</p><h2><strong>Oracle: The $108 Billion Test Case</strong></h2><p>Oracle has emerged as the most extreme example of debt-financed AI infrastructure ambition. As of December 2025, the company carries approximately $108 billion in debt-up from $92.6 billion in May-making it the largest issuer of investment-grade debt among non-financial firms.</p><p>The debt is being deployed to fulfill a staggering $300 billion, five-year contract with OpenAI for cloud compute services, with payments expected to reach $60 billion annually starting in 2027. Oracle&#8217;s remaining performance obligations have exploded to $523 billion-up 438% year-over-year-as the company has signed deals with OpenAI, Meta, NVIDIA, xAI, and others.</p><p><strong>The December 2025 Warning Signs: </strong>Oracle&#8217;s fiscal Q2 2026 earnings (reported December 10, 2025) revealed concerning dynamics. Revenue of $16.06 billion missed expectations of $16.21 billion. Free cash flow was negative $10 billion for the quarter-nearly double the consensus estimate of negative $5.2 billion. The company raised its full-year capex guidance to $50 billion, up from $35 billion just three months prior. The stock fell 11% after the report.</p><p>Citi analyst Tyler Radke estimates Oracle will need to raise $20-30 billion in debt annually for the next three years. Moody&#8217;s changed its outlook on Oracle to negative in July 2025, citing &#8220;the expectation of continuing elevated leverage and increasingly negative free cash flow.&#8221; Oracle&#8217;s 5-year credit default swaps have climbed to their highest level since 2009.</p><p><strong>The Counterparty Problem: </strong>The most significant risk may be Oracle&#8217;s largest customer. OpenAI remains unprofitable and relies on continuous funding rounds. Sam Altman has stated OpenAI will reach $20 billion in annualized revenue in 2025 and projects &#8220;hundreds of billions&#8221; by 2030-but paying Oracle $60 billion annually starting 2027 requires extraordinary revenue growth. As Moody&#8217;s analysts noted: &#8220;Given the lack of financial information about the potential counter parties, this risk assessment is subjective at best.&#8221;</p><h2><strong>The $38 Billion Stargate Debt Package</strong></h2><p>In October 2025, banks led by JPMorgan Chase and Mitsubishi UFJ Financial Group began marketing a $38 billion debt offering-the largest AI infrastructure financing in history-to fund data centers tied to Oracle. The package is split across two facilities: $23.25 billion for a Texas campus and $14.75 billion for a Wisconsin project.</p><p>These facilities are part of the Stargate initiative, a $500 billion AI infrastructure project announced by President Trump in January 2025 involving OpenAI, Oracle, and SoftBank. The project aims to build 10 gigawatts of compute capacity across sites in Texas, New Mexico, Ohio, and Wisconsin. SoftBank has already borrowed $10 billion from Mizuho for its portion; Blue Owl raised $18 billion from Japanese banks for a New Mexico site.</p><p>The financing structure reveals the precarious nature of this buildout. Oracle has signed 17-year leases on sites to support the debt, with lenders stepping in to assume control if projects default. The dependency chain is stark: Oracle borrows to build infrastructure &#8594; OpenAI commits to pay Oracle &#8594; OpenAI must raise funds or generate revenue &#8594; investors must continue believing in the AI thesis.</p><h2><strong>CoreWeave: The GPU Collateral Experiment</strong></h2><p>CoreWeave has pioneered a novel and concerning financing model: using NVIDIA GPUs as collateral for massive debt facilities. The company has raised $25+ billion in total capital commitments, with approximately $9 billion in current and non-current debt secured primarily by its GPU inventory.</p><p><strong>The Collateral Problem: </strong>Unlike real estate-which generally appreciates and can be amortized over decades-GPUs are rapidly depreciating assets. CoreWeave&#8217;s loan terms require quarterly payments based on cash flow and, critically, the depreciated value of the GPUs used as collateral. As new NVIDIA architectures launch and GPU rental prices fall, the collateral value shrinks while the principal remains fixed.</p><p>The H100 rental market has already seen dramatic price declines: from $8/hour at peak to $2.36-3.50/hour by late 2025-a 60-70% reduction. Analysis suggests that once H100 rental rates fall below $1.65/hour, revenues no longer recoup the investment. Prices need to remain above $2.85/hour to beat stock market returns.</p><p><strong>The Depreciation Discrepancy: </strong>CoreWeave depreciates its GPUs over 6 years-the same aggressive schedule the hyperscalers use. Competitor Nebius uses a 4-year depreciation period. This longer schedule artificially suppresses CoreWeave&#8217;s operating expenses and inflates its operating income, while masking the true rate of asset value erosion.</p><p>Jim Chanos, the legendary short-seller who exposed Enron, has raised concerns about CoreWeave&#8217;s model. The company&#8217;s annualized interest expense of approximately $1.2 billion approaches its adjusted EBITDA of $3.4 billion, leaving minimal margin for GPU depreciation. CoreWeave&#8217;s stock has fallen approximately 57% from its June 2025 high, though it recovered after announcing a $14.2 billion contract with Meta.</p><p><strong>Customer Concentration Risk: </strong>Just two companies drove 77% of CoreWeave&#8217;s 2024 revenues, with Microsoft accounting for 62%. These largest customers are also its biggest competitors-hyperscalers who could decide to build rather than rent at any moment.</p><h2><strong>The GPU-Backed Debt Contagion</strong></h2><p>CoreWeave&#8217;s model has spawned imitators. London-based Fluidstack secured over $10 billion in loans from Macquarie and other lenders using NVIDIA GPUs as collateral. Multiple AI cloud computing startups now use high-power chips as collateral, with total GPU-backed borrowing exceeding $20 billion.</p><p>Lenders are demanding interest rates in the double digits-exceeding most high-yield bond requirements-reflecting the depreciation risk. Some companies are exploring AMD chips as alternative collateral. TensorWave is actively seeking debt financing with AMD chips as collateral, which would be one of the first such deals.</p><p>The fundamental question remains: what happens when the next NVIDIA architecture launches and existing GPU collateral loses 40-50% of its value overnight? The loans require principal payments; the collateral doesn&#8217;t maintain principal value.</p><h1><strong>Part III: The Securitization Parallel</strong></h1><h2><strong>Data Center ABS and CMBS: 2008 Redux?</strong></h2><p>Asset-backed securities (ABS) and commercial mortgage-backed securities (CMBS) are emerging as significant funding sources for AI infrastructure. BofA notes that digital infrastructure-primarily data centers-accounts for $82 billion of the $1.6 trillion U.S. ABS market, having expanded more than 9x in less than five years. Data centers backed 63% of that digital infrastructure segment.</p><p>These securities bundle data center lease payments-rent paid by hyperscalers to facility operators-into tradeable bonds structured by risk tranche. The pitch is compelling: hyperscaler tenants have strong credit ratings, long-term leases, and mission-critical need for the facilities.</p><p><strong>The 2008 Echo: </strong>ABS are viewed with caution since the 2008 financial crisis, when billions of dollars&#8217; worth of products turned out to be backed by soured loans and highly illiquid assets. The data center version differs in that the underlying cash flows come from creditworthy tenants rather than subprime borrowers. However, the structures share a common vulnerability: they assume the underlying asset-whether a house or a GPU cluster-maintains value throughout the security&#8217;s life.</p><p>Al Cattermole, fixed income portfolio manager at Mirabaud Asset Management, told Reuters in November 2025 that his team had not invested in any AI-linked investment-grade or high-yield bonds. His reasoning: &#8220;Until we see data centres being delivered on time and on budget and providing the computing power that they are intended to-and there still being the demand for it-it is untested. And because it&#8217;s untested, that&#8217;s why I think you need to be compensated like an equity investor.&#8221;</p><h2><strong>Private Credit: The New Risk Reservoir</strong></h2><p>Private credit has become a crucial funding source for AI infrastructure. UBS estimates private credit AI-related loans nearly doubled in the 12 months through early 2025. Morgan Stanley projects private credit could supply over half the $1.5 trillion needed for data center buildout through 2028-approximately $750 billion.</p><p>The appeal for borrowers is clear: private credit offers fixed-rate structures, customized terms, and avoidance of public bond market scrutiny. Meta&#8217;s $29 billion deal with PIMCO and Blue Owl-structured as $26 billion in debt and $3 billion in equity-exemplifies the model. Microsoft struck a $30 billion partnership with BlackRock. xAI raised $5 billion in syndicated debt.</p><p><strong>The Illiquidity Risk: </strong>Unlike traded bonds, private credit loans are harder to trade during market turmoil. The Bank of England has flagged that &#8220;pockets of risk are building in parts of the financial system populated by opaque, hard-to-trade illiquid assets.&#8221; If AI demand disappoints and borrowers struggle, private credit investors may find themselves holding assets with no market and rapidly deteriorating collateral.</p><h1><strong>Part IV: Historical Parallels and Differences</strong></h1><h2><strong>The Telecom Bubble Comparison</strong></h2><p>The telecom bubble offers the most relevant precedent. WorldCom&#8217;s $11 billion fraud included depreciation manipulation alongside capitalizing operating expenses. Waste Management stretched garbage truck depreciation periods to reduce annual expense, ultimately restating $1.7 billion in earnings.</p><p>More broadly, $500+ billion was invested in fiber optic infrastructure, 85-95% of which remained &#8220;dark&#8221; (unused) four years after the bubble burst. Global Crossing achieved a $47 billion market cap without ever turning a profit. Lucent Technologies offered $8.1 billion in vendor financing-about 24% of revenue-and collapsed when customers defaulted.</p><p>JP Morgan has explicitly made this comparison, estimating AI will need $650-800 billion in annual revenue by 2030 just to generate a 10% return on infrastructure capex. Bain estimates an $800 billion annual revenue gap between AI investment and revenues.</p><h2><strong>Critical Differences</strong></h2><p>Several factors distinguish the current situation from the telecom bubble. Hyperscalers possess massive cash reserves and sustainable core businesses unlike pure-play telecoms. Amazon&#8217;s AWS, Microsoft&#8217;s Azure, and Google Cloud generate hundreds of billions in annual revenue with strong operating margins. The AI infrastructure spending, while enormous, represents a fraction of their financial capacity. Meta issued its first dividend in 2024 despite the capex boom-impossible for debt-laden 1990s telecoms.</p><p>Additionally, infrastructure financing has matured as an asset class. Specialized lenders understand data center economics. Structures include ring-fenced cash flows, specific covenants, and security packages that didn&#8217;t exist in the 1990s.</p><p><strong>However: </strong>Oracle is not a hyperscaler. It carries $108 billion in debt, has negative free cash flow, and is building capacity for a customer that has never been profitable. CoreWeave is not a hyperscaler. It has 77% customer concentration, GPU collateral that depreciates rapidly, and an interest coverage ratio of 0.17. The startups borrowing billions against GPU inventory are certainly not hyperscalers. The comparison to telecom overbuild is most apt not for Microsoft or Google, but for the second and third tier of infrastructure providers.</p><h1><strong>Part V: The NVIDIA Paradox</strong></h1><h2><strong>Why Obsolescence Might Benefit NVIDIA</strong></h2><p>Here&#8217;s where Burry&#8217;s thesis creates an unexpected implication for NVIDIA investors. If GPUs depreciate faster than accounting schedules suggest, this creates sustained demand for replacement chips rather than a one-time buildout.</p><p>CoreWeave CEO Michael Intrator provided direct evidence: &#8220;A batch of Nvidia H100 chips became available because a contract expired, and they were immediately booked at 95% of their original price.&#8221; He added that &#8220;all of our Nvidia A100 chips, which were announced in 2020, are all fully booked.&#8221;</p><p>The &#8220;value cascade&#8221; model explains how older GPUs retain economic utility despite obsolescence: Years 1-2 for frontier model training, Years 3-4 for high-value real-time inference, Years 5-6 for batch inference and analytics. Meta exemplifies this tiering-training on cutting-edge H100/H200 GPUs but running inference on AMD MI300X chips.</p><p>If Burry is correct that 6-year depreciation is aggressive, the implication is that hyperscalers must continuously purchase new NVIDIA chips at 3-4 year intervals rather than 6-year cycles. This doubles the replacement frequency and sustains demand indefinitely. NVIDIA&#8217;s $500 billion backlog through 2026 supports this thesis.</p><h2><strong>The Competitive Moat</strong></h2><p>NVIDIA&#8217;s defensive position remains formidable regardless of the depreciation debate. SemiAnalysis conducted a five-month benchmark of AMD&#8217;s MI300X in December 2024 and concluded: &#8220;For all models, the H100/H200 wins relative to MI300X. AMD&#8217;s software experience is riddled with bugs rendering out of the box training with AMD impossible... The CUDA moat has yet to be crossed by AMD.&#8221;</p><p>NVIDIA&#8217;s CUDA ecosystem encompasses 3.5 million developers with nearly two decades of optimization. Intel&#8217;s Gaudi holds less than 1% market share. Custom silicon from Google, Amazon, and Meta handles primarily inference and internal workloads-less than 20% of frontier model training runs on non-NVIDIA silicon.</p><h1><strong>Conclusion: Layers of Risk</strong></h1><p>The AI infrastructure financing landscape presents layered risks that compound upon each other:</p><p><strong>Layer 1 - Depreciation Manipulation: </strong>Hyperscalers have documented $13+ billion in annual earnings benefits from extending depreciation schedules. Amazon&#8217;s reversal for AI servers validates that these schedules are aggressive.</p><p><strong>Layer 2 - Debt Financing Surge: </strong>AI infrastructure financing surged to $125 billion in 2025 (8x 2024 levels), with projections of $750 billion in private credit through 2028. This creates massive leverage exposure if demand disappoints.</p><p><strong>Layer 3 - Collateral Degradation: </strong>GPU-backed debt exceeding $20 billion depends on assets that have already declined 60-70% in rental value. The 6-year depreciation schedules used by borrowers like CoreWeave mask this reality.</p><p><strong>Layer 4 - Counterparty Concentration: </strong>Oracle&#8217;s largest customer is unprofitable. CoreWeave&#8217;s two largest customers represent 77% of revenue. The dependency chains are fragile.</p><p><strong>Layer 5 - Securitization Proliferation: </strong>Data center ABS/CMBS have grown 9x in five years. Private credit markets are increasingly exposed to AI infrastructure. The lack of transparency about actual utilization and demand echoes pre-2008 mortgage market opacity.</p><p>The key variable is whether AI generates sufficient return on investment to justify the infrastructure buildout. Combined hyperscaler capex guidance exceeds $300 billion for 2025 alone. Backlogs total $747 billion. Power constraints, not demand, appear to be the limiting factor.</p><p>For NVIDIA, the paradox of obsolescence remains intact: even if individual GPUs become worthless faster than accounting suggests, the aggregate effect is a treadmill that customers cannot exit. Oracle&#8217;s $50 billion annual capex, CoreWeave&#8217;s refinancing requirements, and the broader infrastructure boom all translate to continuous GPU orders.</p><p>The risk is not that AI demand disappears-it almost certainly won&#8217;t. The risk is that the second and third tier of infrastructure providers, loaded with debt secured by depreciating assets, cannot survive the gap between infrastructure investment and AI monetization. Amazon&#8217;s depreciation reversal may represent the market&#8217;s most honest signal: AI hardware depreciates faster than traditional servers, but the hyperscalers will keep buying. Whether Oracle, CoreWeave, and the GPU-backed lending ecosystem can say the same is the $176 billion question.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://carryon.capital/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Carry On Capital! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[OpenDoor and OpenStore: A Masterclass in Value Destruction]]></title><description><![CDATA[What happens when VC investors masquerade as PE investors? $2 billion goes up in flames]]></description><link>https://carryon.capital/p/opendoor-and-openstore-a-masterclass</link><guid isPermaLink="false">https://carryon.capital/p/opendoor-and-openstore-a-masterclass</guid><dc:creator><![CDATA[Mark Lewis]]></dc:creator><pubDate>Mon, 24 Nov 2025 19:53:32 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!ip22!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!ip22!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!ip22!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png 424w, https://substackcdn.com/image/fetch/$s_!ip22!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png 848w, https://substackcdn.com/image/fetch/$s_!ip22!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png 1272w, https://substackcdn.com/image/fetch/$s_!ip22!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!ip22!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png" width="1376" height="768" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:768,&quot;width&quot;:1376,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:1956080,&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://carryoncapital.substack.com/i/179848635?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!ip22!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png 424w, https://substackcdn.com/image/fetch/$s_!ip22!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png 848w, https://substackcdn.com/image/fetch/$s_!ip22!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.png 1272w, https://substackcdn.com/image/fetch/$s_!ip22!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F33ae915b-d8ce-4176-bb5b-bbbb903d6e4a_1376x768.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 role="img" 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><title></title><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></p><p>In June 2023,<a href="https://x.com/mrloo/status/1673531846687346688"> I publicly raised concerns about OpenStore</a>. Not because I&#8217;m some oracle of business wisdom, but because the fundamentals were screaming red flags that anyone in the ecommerce space could see. The aggressive aggregation model, the lack of domain expertise, the hubris of believing algorithms could replace operational know-how.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://carryon.capital/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Carry On Capital! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>I felt like Michael Burry in 2006, watching the mortgage market and wondering if I was the only one who could do basic math. The difference? Burry was betting against fraud hidden in complexity. I was just pointing out incompetence hiding in plain sight.</p><p>Now, in late 2025,<a href="https://www.cnbc.com/2025/08/08/openstore-demise-endgame-for-once-booming-ecommerce-aggregator-market.html"> OpenStore is essentially dead</a>. They&#8217;ve shut down 40+ brands, keeping only Jack Archer, and<a href="https://www.bloomberg.com/news/articles/2025-07-25/e-commerce-startup-openstore-cuts-valuation-by-95-taps-new-ceo"> reportedly raised at a $50 million valuation</a>. That&#8217;s a staggering 95% drop from their previous<a href="https://techcrunch.com/2022/09/22/keith-rabois-openstore-valuation-970m/"> nearly $1b valuation in September 2022</a>. They raised over $150 million in investor capital buying brands they couldn&#8217;t profitably operate, all while their architect, Keith Rabois, promoted mediocre milestones on social media like they were revolutionary achievements.</p><p>But here&#8217;s the thing: OpenStore isn&#8217;t an anomaly. It&#8217;s a pattern.</p><h2><strong>When VCs Play PE in Industries They Know Nothing About</strong></h2><p>Here&#8217;s what really happened with OpenStore, and it&#8217;s a pattern repeating across multiple sectors: venture capitalists trying to execute private equity rollup strategies in industries where they have zero domain expertise.</p><p>Private equity firms have been doing rollups for decades. They work when you have operators who deeply understand the industry, know how to identify operational efficiencies, can integrate acquisitions effectively, and understand the unit economics down to the cent. PE firms hire industry veterans. They bring in people who&#8217;ve run similar businesses for 20+ years. They respect the operational complexity.</p><p>VCs like Rabois looked at this playbook and thought: &#8220;We can do that, but with &#8216;technology&#8217; and &#8216;algorithms.&#8217;&#8221; Then they proceeded to do everything wrong.</p><p>OpenStore didn&#8217;t hire people with ecommerce experience. They didn&#8217;t bring in operators who had successfully scaled DTC brands, managed Amazon storefronts, or understood the nuances of customer acquisition costs, inventory management, and brand positioning. Instead, they hired from tech companies like Apple, Uber, and DoorDash.</p><p>Think about how insane that is. You&#8217;re buying 40+ ecommerce brands, and you staff your company with people from ride-sharing apps and tech hardware companies. People who&#8217;ve never had to worry about cost of goods sold, supplier relationships, seasonal inventory planning, or the difference between a sustainable CAC:LTV ratio and one that burns cash.</p><p>It&#8217;s the blind leading the blind, except the blind people are convinced they can see better than everyone else because they know nothing about the industry. They genuinely believed their ignorance was an asset. &#8220;We&#8217;re not constrained by industry thinking!&#8221; they&#8217;d say. &#8220;We can see opportunities others miss!&#8221;</p><p>No. You&#8217;re just ignorant. And your ignorance cost $150 million and destroyed 40+ businesses.</p><p>The arrogance is breathtaking. Imagine a world-class chef watching someone who&#8217;s never cooked before walk into a Michelin-star restaurant and declare: &#8220;I&#8217;m going to revolutionize fine dining because I&#8217;m not constrained by culinary training. I have an algorithm!&#8221; That&#8217;s essentially what happened here.</p><p>The people who actually understand ecommerce, the ones who&#8217;ve been in the trenches building and scaling brands, saw this coming from miles away. We weren&#8217;t smarter. We just knew what they didn&#8217;t know. And what they didn&#8217;t know could fill a warehouse.</p><p>When you combine VCs with no ecommerce experience, executives with no ecommerce experience, and a strategy that requires deep operational excellence in ecommerce, you get exactly what we got: spectacular failure.</p><p>This is what happens when venture capital, drunk on years of backing asset-light software businesses, decides to wade into asset-heavy operational businesses. Software can scale with minimal marginal cost. Real businesses with physical products, inventory, supply chains, and customer service teams? Those require actual operational expertise.</p><p>But admitting that would require humility. And humility doesn&#8217;t raise $150 million or get you on the Forbes Midas List.</p><h2><strong>The OpenDoor Parallel: A Masterclass in Value Destruction</strong></h2><p>Let&#8217;s talk about OpenDoor, another Keith Rabois creation, this time co-founded and currently serving on its board. In December 2020, Rabois partnered with &#8220;SPAC King&#8221;<a href="https://techcrunch.com/2020/09/15/opendoor-to-go-public-by-way-of-chamath-palihapitiya-spac/"> Chamath Palihapitiya to take OpenDoor public</a> via Social Capital Hedosophia II at a $4.8 billion enterprise value. The market initially loved it. The valuation soared to nearly $18 billion on its first day of trading.</p><p>Today? The story is both more volatile and more revealing.<a href="https://stockinvest.us/stock/OPEN"> OpenDoor&#8217;s stock hit a 52-week low of $0.51 per share in mid-2025</a>. That&#8217;s a catastrophic 97% decline from its IPO peak. While the stock has since surged to trade around $6-7 (giving it a current market cap of approximately $6-7 billion as of November 2025), this represents classic meme stock behavior, not fundamental improvement.</p><p>OpenDoor has never turned a profit except for<a href="https://www.inman.com/2022/05/05/opendoor-reaches-first-profitable-quarter-in-q1-with-28m-net-income/"> brief quarters in 2022-2023</a>. In 2024,<a href="https://www.nasdaq.com/articles/opendoor-technologies-inc-reports-fourth-quarter-and-full-year-2024-financial-results"> the company posted a net loss of $392 million</a>. In Q3 2025 (their most recent quarter)<a href="https://investor.opendoor.com/news-releases/news-release-details/opendoor-announces-second-quarter-2025-financial-results"> they lost $0.12 per share and posted a net loss of $90 million</a>. The company is targeting &#8220;adjusted net income breakeven by the end of 2026.&#8221; That&#8217;s six years after going public, and after cumulative losses in the billions.</p><h2><strong>The Math That VCs Don&#8217;t Want You To See</strong></h2><p>Here&#8217;s where it gets really ugly. Let&#8217;s talk about the actual numbers, because they tell a story of systematic value destruction that should make any investor sick.</p><p><strong>Total capital raised by OpenDoor:</strong></p><ul><li><p>~$1.3 billion in pre-IPO venture capital funding</p></li><li><p>$1 billion from the SPAC merger (2020)</p></li><li><p>$850 million in a post-IPO equity round (August 2021)</p></li><li><p><strong>Total equity capital raised: approximately $2.1-2.2 billion</strong></p></li></ul><p>And what do investors have to show for it?</p><p><a href="https://investor.opendoor.com/news-releases/news-release-details/opendoor-announces-second-quarter-2025-financial-results">OpenDoor&#8217;s current book value (stockholders&#8217; equity as of Q2 2025): $631 million</a>.</p><p>Read that again. They raised over $2.1 billion in equity capital. The book value of the company (assets minus liabilities) is $631 million. That means they&#8217;ve destroyed approximately $1.4-1.5 billion in shareholder value. Gone. Vaporized.</p><p>That&#8217;s not just a negative return. That&#8217;s a negative IRR over the entire life of the company. Every single investor, from the earliest venture rounds through the SPAC and post-IPO financing, has collectively lost money on a book value basis. The only way anyone makes money now is if they can find a greater fool to buy the meme stock at an inflated price.</p><p>This isn&#8217;t disruption. This is destruction. And not the good kind of &#8220;creative destruction&#8221; that capitalism is supposed to deliver. This is pure capital incineration, dressed up in the language of innovation and sold to investors by people who confused their past successes in completely different industries with competence in real estate.</p><p>Think about what else could have been done with $2.1 billion. That&#8217;s real money. That&#8217;s funding for dozens of actually viable startups. That&#8217;s returns that could have gone to pension funds and endowments. Instead, it&#8217;s been systematically destroyed by a business model that economics 101 could have told you wouldn&#8217;t work.</p><p>Like the synthetic CDOs in The Big Short, everyone was so busy celebrating the innovation that nobody bothered to check if the underlying assets made any sense. The difference is that mortgage traders at least understood mortgages. These VCs didn&#8217;t even understand the basics of the industries they were &#8220;disrupting.&#8221;</p><h2><strong>The iBuyer &#8220;Lemons Problem&#8221;</strong></h2><p>The fundamental flaw in the iBuyer model (what economists call the &#8220;lemons problem&#8221;) was well-documented even before OpenDoor went public. When sellers know more about their homes than buyers (including algorithmic buyers), they have an incentive to offload their worst properties to instant-cash buyers. OpenDoor&#8217;s algorithms, no matter how sophisticated, consistently underperformed against this adverse selection problem.</p><p>Rabois, of course, dismissed these concerns. In late 2020, when he partnered with Chamath to take OpenDoor public via SPAC, he was all over social media promoting it as the future of real estate. The fact that he had no real estate experience? Irrelevant. The fact that the unit economics were questionable? Details. The fact that<a href="https://www.cnbc.com/2021/11/02/zillow-shares-plunge-after-announcing-it-will-close-home-buying-business.html"> Zillow, with far more data and domain expertise, would shut down their iBuying operation just a year later</a>? A validation that OpenDoor was &#8220;the winner.&#8221;</p><p>The hubris is breathtaking. While actual real estate professionals were raising red flags about adverse selection and capital intensity, Rabois was tweeting about &#8220;revolutionizing a $1.6 trillion market.&#8221; Now, five years later, OpenDoor has revolutionized nothing except new ways to destroy shareholder value.</p><p><a href="https://www.floridarealtors.org/news-media/news-articles/2022/02/zillow-offers-lost-881m-2021-shutdown">Zillow shut down Zillow Offers in November 2021 after $881 million in losses</a>.<a href="https://www.axios.com/2022/11/09/redfin-home-flipping-layoffs-housing-market"> Redfin shut down RedfinNow in November 2022</a>. But OpenDoor pressed on, burning through billions while Rabois championed it as a revolutionary real estate platform.</p><h2><strong>From &#8220;Tech-Enabled&#8221; to Plain Old Real Estate</strong></h2><p>Here&#8217;s what OpenDoor actually is: a poorly performing REIT masquerading as a technology company. They buy homes, hold inventory, and try to flip them. There&#8217;s no revolutionary technology here. Just a capital-intensive, low-margin business in one of the most cyclical sectors in the economy. When interest rates rose and the housing market cooled, OpenDoor was left holding billions in depreciating inventory and no path to profitability.</p><p>The recent stock surge? It&#8217;s not driven by improved fundamentals.<a href="https://investor.opendoor.com/news-releases/news-release-details/opendoor-announces-shareholder-first-dividend-tradable-warrants"> The new CEO, Kaz Nejatian, announced a gimmick to squeeze short sellers by issuing tradable warrants to shareholders</a>. It&#8217;s the kind of financial engineering that sends retail traders into a frenzy but does nothing to fix the underlying business model.</p><p>Speaking of Nejatian, here&#8217;s an interesting detail that fits the pattern:<a href="https://investor.opendoor.com/news-releases/news-release-details/opendoor-names-kaz-nejatian-ceo-founders-rabois-and-wu-rejoin"> he came from Shopify where he served as COO</a>, but his previous company Kash was reportedly &#8220;acquired by one of the largest fintech companies in the U.S.&#8221; with mysteriously no public record of this acquisition anywhere. No SEC filings, no press releases from the supposed acquirer, no deal terms, nothing. In an industry where founders inflate their exits like balloons at a children&#8217;s party, OpenDoor managed to hire a CEO whose biggest career achievement remains unverified. It&#8217;s perfect, really a company built on financial engineering and meme stock manipulation, run by someone whose own exit story appears equally engineered.</p><p>With<a href="https://www.benzinga.com/quote/OPEN/short-interest"> approximately 25% of the float sold short</a>, OpenDoor has achieved meme stock status, not business success.</p><h2><strong>The Aggregator Graveyard</strong></h2><p><a href="https://www.cnbc.com/2025/08/08/openstore-demise-endgame-for-once-booming-ecommerce-aggregator-market.html">OpenStore&#8217;s demise marks the effective end of the ecommerce aggregator boom</a>.<a href="https://www.prnewswire.com/news-releases/thrasio-emerges-from-chapter-11-and-announces-new-leadership-302176011.html"> Thrasio (once the poster child with billions in funding) filed for bankruptcy in February 2024</a>. Perch, Heyday, Unybrands: all either failed, merged in desperation, or cut their valuations dramatically.<a href="https://www.hahnbeck.com/blog/2021/11/30/whos-funding-the-aggregators"> The entire sector raised over $16 billion collectively</a>, and almost all of it has been vaporized.</p><p>But here&#8217;s the kicker: even as the entire aggregator sector was collapsing around him, Rabois was still promoting OpenStore&#8217;s &#8220;successes&#8221; on social media. In March 2023, while Thrasio was heading toward bankruptcy and other aggregators were desperately cutting valuations, Rabois was tweeting about OpenStore&#8217;s &#8220;operational excellence&#8221; and sharing articles about scaling brands from $1M to $10M as if this was revolutionary rather than table stakes for any competent ecommerce operator.</p><p>By July 2025, reality finally caught up. OpenStore&#8217;s valuation was cut by 95%, a new CEO was brought in, and Rabois quietly distanced himself from day-to-day operations. No mea culpa. No acknowledgment of the failure. Just a swift pivot back to Khosla Ventures where he could start the cycle anew with fresh LP money.</p><p>Why did all these aggregators fail? Because buying businesses isn&#8217;t the hard part. Operating them profitably is. And you can&#8217;t algorithm your way out of needing actual operational expertise.</p><h2><strong>The Rabois Pattern</strong></h2><p>What connects these stories is Keith Rabois. He&#8217;s a venture capitalist with an impressive resume (PayPal, Square, LinkedIn) who appears to believe his past successes make him infallible in any market he enters.</p><p>With OpenStore, Rabois had no ecommerce operational experience but confidently declared he could &#8220;acquire a business in a day&#8221; and eventually wanted to get to &#8220;one an hour.&#8221; He promoted the company relentlessly on social media, posting about &#8220;the best talent&#8221; and &#8220;the future of commerce online&#8221; even as the business was imploding behind the scenes.</p><p>When things went south? Silence. No accountability. No acknowledgement of the $150 million raised and 40+ brands destroyed. Just a pivot to calling it &#8220;10x focus on what is anomalously great.&#8221; As if concentrating on one surviving brand out of 40 was the plan all along.</p><p>With OpenDoor, the playbook is eerily similar: aggressive promotion, grandiose claims about revolutionizing a massive market, algorithmic overconfidence, and a consistent inability to turn a profit despite years and billions in capital.<a href="https://investor.opendoor.com/news-releases/news-release-details/opendoor-names-kaz-nejatian-ceo-founders-rabois-and-wu-rejoin"> Rabois rejoined OpenDoor&#8217;s board in September 2025</a>, just in time for the company to become a meme stock rather than a sustainable business.</p><h2><strong>The Art of Failing Up</strong></h2><p>There&#8217;s something particularly galling about Rabois&#8217;s trajectory. In any other industry, destroying $150 million at OpenStore while simultaneously presiding over $1.4 billion in value destruction at OpenDoor would end a career. In Silicon Valley? It gets you a promotion and access to $3.1 billion in fresh capital.</p><p>When<a href="https://en.wikipedia.org/wiki/Keith_Rabois"> Vinod Khosla announced Rabois&#8217;s return in January 2024</a>, he gushed that Keith &#8220;knows how to advise entrepreneurs on hiring/firing, running teams, managing funding.&#8221; This is the same person whose own venture couldn&#8217;t manage any of these things successfully. OpenStore went from unicorn to essentially a single menswear brand. The open.store domain, once the flagship of their &#8220;revolutionary ecommerce platform&#8221;, now doesn&#8217;t even load.</p><p>The timing tells the real story.<a href="https://en.wikipedia.org/wiki/Keith_Rabois"> Rabois left Khosla for Founders Fund in February 2019</a>, co-founded OpenStore in Miami in 2021 during the peak of cheap capital, watched it implode through 2023-2024, and then boomeranged back to Khosla in January 2024,  just as the OpenStore disaster became impossible to ignore. Forbes called it a &#8220;surprise return.&#8221; The only surprise is how transparent the move was.</p><p>This is the Silicon Valley accountability problem in miniature: fail spectacularly, move laterally, raise more money, repeat. The same network that enables this behavior then wonders why &#8220;founders&#8221; with zero domain expertise keep burning billions on obviously flawed business models. These VCs spend their careers vying to be featured on the Forbes Midas List, but it seems their touch turns real, hard-working businesses to dirt instead of gold. King Midas at least had the excuse of a curse, these guys are just incompetent.</p><h2><strong>Not Gloating: Just Pattern Recognition</strong></h2><p>I&#8217;m not writing this to gloat. I&#8217;m writing it because there&#8217;s a lesson here about venture capital, expertise, and humility (or the lack thereof).</p><p>The venture capital model works when VCs back founders with domain expertise. It fails spectacularly when VCs believe they can parachute into complex operational businesses and use capital and &#8220;technology&#8221; to paper over their lack of expertise.</p><p>OpenStore wasn&#8217;t killed by market conditions. Plenty of ecommerce businesses thrived during the same period. It was killed by operational incompetence. Similarly, OpenDoor isn&#8217;t struggling because the real estate market is inherently unprofitable. Traditional brokerages and individual investors make money every day. It&#8217;s struggling because the iBuyer model, as architected, doesn&#8217;t work at scale.</p><p>The recent meme stock surge only obscures the fundamental reality: after 11 years in operation and five years as a public company, OpenDoor still loses hundreds of millions of dollars annually while having destroyed over $1.4 billion in shareholder value.</p><h2><strong>The Bigger Picture</strong></h2><p>These failures matter beyond just a few companies. They represent hundreds of millions in misallocated capital, hundreds of jobs lost, and the destruction of dozens of previously viable ecommerce brands that got rolled up and mismanaged into oblivion.</p><p>More importantly, they represent a broader phenomenon in tech and venture capital: the belief that &#8220;disruption&#8221; means you can ignore the fundamentals of the industries you&#8217;re trying to disrupt. That algorithms can replace judgment. That capital can substitute for competence. That viral marketing can replace product-market fit. That hiring from Big Tech is better than hiring people who actually understand the business you&#8217;re trying to run.</p><p>Sometimes the emperor really has no clothes. And sometimes the people pointing it out aren&#8217;t being cynical. They&#8217;re just paying attention to the fundamentals everyone else is ignoring in favor of a good story told by a charismatic founder with an impressive pedigree but zero relevant experience.</p><h2><strong>Postscript: Where Are They Now?</strong></h2><p><strong>OpenStore</strong> is now essentially just Jack Archer, a menswear brand, run by a new CEO with no involvement from Rabois in day-to-day operations. The open.store domain now redirects to jackarcher.com. Not exactly the revolutionary &#8220;portfolio of serendipitous discovery&#8221; that was promised.</p><p><strong>OpenDoor</strong> continues to lose money quarter after quarter, targeting profitability &#8220;by the end of 2026.&#8221; That&#8217;s a promise they&#8217;ve been making in various forms for years. The stock has become a meme stock playground with extreme volatility, recently trading in the $6-7 range on warrant gimmicks and short squeezes rather than actual business improvement. The company is now run by a new CEO who describes OpenDoor as &#8220;a software and AI company&#8221; rather than acknowledging the reality: it&#8217;s a capital-intensive real estate flipping operation that has yet to prove it can make money. With over $1.4 billion in shareholder value destroyed, it stands as a monument to what happens when VCs play in industries they don&#8217;t understand.</p><p><strong>Keith Rabois?</strong> After OpenStore&#8217;s spectacular implosion became undeniable, he made a surprise return to Khosla Ventures in January 2024 as a managing director, conveniently leaving Founders Fund just as his ecommerce aggregator was collapsing. The official story? He didn&#8217;t like the commute from SF to Sand Hill Road back in 2019. The convenient timing? Founders Fund had cut back their fund size while Khosla had just closed on $3.1 billion in fresh capital.</p><p>Khosla even set up a new Miami office for him in Wynwood, a validation of his &#8220;commitment to the city&#8221;. The same city where he co-founded OpenStore in 2021 before watching it burn through $150 million. Now he&#8217;s back on OpenDoor&#8217;s board, presumably to oversee its continued money-losing operations as it promises profitability &#8220;by the end of 2026.&#8221; Same playbook, different fund, fresh billions to deploy.</p><h2><strong>The Real Cost</strong></h2><p>The pattern is clear: OpenStore, OpenDoor, and the broader failures they represent aren&#8217;t bugs in the Silicon Valley system, they&#8217;re features. They&#8217;re what happens when venture capitalists confuse confidence with competence, when viral marketing substitutes for viable business models, and when the ability to raise capital becomes more important than the ability to deploy it wisely.</p><p>The real tragedy isn&#8217;t just the billions destroyed. It&#8217;s that this capital could have funded hundreds of boring, profitable businesses run by operators with actual domain expertise. Instead, it went to feed the egos of VCs who thought they could algorithm their way through industries they didn&#8217;t understand.</p><p>Until there are real consequences for this kind of value destruction. Until LPs stop funding VCs who consistently burn billions, we&#8217;ll keep seeing the same pattern: charismatic founders with zero relevant experience raising massive rounds, burning through capital while posting victory laps on social media, then failing up to the next fund when reality catches up.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://carryon.capital/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Carry On Capital! 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