{"id":422982,"date":"2025-07-22T12:17:46","date_gmt":"2025-07-22T11:17:46","guid":{"rendered":"https:\/\/seedlegals.com\/?p=422982"},"modified":"2025-07-22T12:17:46","modified_gmt":"2025-07-22T13:17:46","slug":"how-to-get-up-to-500m-in-federal-tax-relief","status":"publish","type":"post","link":"https:\/\/seedlegals.com\/us\/resources\/how-to-get-up-to-500m-in-federal-tax-relief\/","title":{"rendered":"How to get up to $500M in federal tax relief"},"content":{"rendered":"","protected":false},"excerpt":{"rendered":"<p>Could you sell your startup for hundreds of millions and pay little to no federal tax? It sounds too good to be true, but under the right circumstances, it\u2019s possible.<\/p>\n","protected":false},"author":169,"featured_media":422991,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[146,147],"tags":[],"event_tags":[],"class_list":["post-422982","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-funding-guides-us","category-startup-guides-us"],"acf":{"blog_layout":"v2","v2":{"hero":{"image_background_color":"#E7F1FF","image_fit":"img--cover"},"adverts":[{"type":"selector","selected_advert":{"ID":412070,"post_author":"77","post_date":"2024-11-11 09:48:00","post_date_gmt":"2024-11-11 09:48:00","post_content":"","post_title":"US - Talk to the team","post_excerpt":"","post_status":"publish","comment_status":"closed","ping_status":"closed","post_password":"","post_name":"us-newsletter","to_ping":"","pinged":"","post_modified":"2024-11-13 16:19:20","post_modified_gmt":"2024-11-13 16:19:20","post_content_filtered":"","post_parent":0,"guid":"https:\/\/seedlegals.com\/?post_type=blog_advert&#038;p=412070","menu_order":0,"post_type":"blog_advert","post_mime_type":"","comment_count":"0","filter":"raw"},"custom_advert":{"advert_tracking_id":"","layout":"default","image":{"image":false,"link":""},"text":{"heading":"","content":"","button":null,"background_color":"#EEF4FF","text_color":"#000646"},"form":{"form":{"type":"none","hubspot_form":{"layout":"newsletter","hide_founderinvestor_toggle":false,"default_community":"founder","custom_form_id":"","gdpr_disclaimer":"By subscribing, you agree to receive information from SeedLegals. You can unsubscribe anytime. View our <a href=\"\/privacy-policy\/\" target=\"_blank\" rel=\"noopener noreferrer\">privacy policy<\/a>"},"custom":{"embed":""},"gtm_form_type":false,"gtm_form_location":false}},"cta_and_testimonials":{"heading":"","button":null,"bullet_points":false,"testimonials":false}}}],"related_sidebar_posts":false},"show_author_card":false,"revision_date":"","hero_image":422991,"has_custom_post_authors":true,"custom_post_authors":{"authors":[{"author":{"ID":169,"user_firstname":"Idin","user_lastname":"Sabahipour","nickname":"Idin Sabahipour","user_nicename":"idin-sabahipour","display_name":"Idin Sabahipour","user_email":"idin@seedlegals.com","user_url":"","user_registered":"2024-08-29 09:55:07","user_description":"","user_avatar":"<img alt='' src='https:\/\/secure.gravatar.com\/avatar\/45fe33a1de890806e7ec6d8ac105288d6228c292c65cf28e96818af3496fd572?s=96&#038;d=mm&#038;r=g' srcset='https:\/\/secure.gravatar.com\/avatar\/45fe33a1de890806e7ec6d8ac105288d6228c292c65cf28e96818af3496fd572?s=192&#038;d=mm&#038;r=g 2x' class='avatar avatar-96 photo' height='96' width='96' loading='lazy' decoding='async'\/>"},"role":"Writer"},{"author":{"ID":172,"user_firstname":"Drew","user_lastname":"Macklin","nickname":"drewmacklin","user_nicename":"drewmacklin","display_name":"Drew Macklin","user_email":"drewmacklin@seedlegals.com","user_url":"","user_registered":"2024-11-08 15:39:57","user_description":"","user_avatar":"<img alt='' src='https:\/\/secure.gravatar.com\/avatar\/8bc81ff5103857f65325d50bbf7a4019afbc9a7a1d4020c1c5993bb03035bccb?s=96&#038;d=mm&#038;r=g' srcset='https:\/\/secure.gravatar.com\/avatar\/8bc81ff5103857f65325d50bbf7a4019afbc9a7a1d4020c1c5993bb03035bccb?s=192&#038;d=mm&#038;r=g 2x' class='avatar avatar-96 photo' height='96' width='96' loading='lazy' decoding='async'\/>"},"role":"Legal review"}]},"is_expert_reviewed":true,"expert_reviewed":{"heading":"Expert reviewed","tooltip_message":"This article has been fact-checked by a SeedLegals subject matter expert.<br><br><a href=\"https:\/\/seedlegals.com\/authors-and-experts\/\" target=\"_blank\">Meet our experts<\/a> and learn more about our review process and quality assurance in our <a href=\"https:\/\/seedlegals.com\/editorial-policy\/\" target=\"_blank\">editorial policy<\/a>."},"post_content_width":"default","post_content":[{"acf_fc_layout":"text","text":"<p>Could you sell your startup for hundreds of millions <em>and<\/em> pay little to no federal tax? It sounds too good to be true, but under the right circumstances, it\u2019s possible.<\/p>\n<p>Some founders have used a legal tax strategy that takes advantage of Qualified Small Business Stock (QSBS) to significantly (or even entirely) cut capital gains taxes on hundreds of millions of dollars.<\/p>\n<p>In this article, we\u2019ll break down the strategy step by step and explain who it may be right for.<\/p>\n<h2>What is QSBS and how does it work?<\/h2>\n<p>Qualified Small Business Stock (QSBS) is a tax break under <a href=\"https:\/\/uscode.house.gov\/view.xhtml?path=\/prelim@title26\/subtitleA\/chapter1\/subchapterP\/part1&amp;edition=prelim\" target=\"_blank\" rel=\"noopener\">Section 1202 of the Internal Revenue code<\/a> that allows founders and investors to exclude up to 100% of federal capital gains tax when selling a qualifying C-corporation.<\/p>\n<p>The tax exemption applies up to the higher of:<\/p>\n<ul>\n<li>$15 million, or<\/li>\n<li><strong>10 times your original investment<\/strong> (we\u2019ll call this the &#8217;10x basis rule&#8217;).<\/li>\n<\/ul>\n<p>This means if your original investment was $10 million, you could exclude up to $100 million of federal capital gains tax.<\/p>\n<p>But there are strict conditions to qualify for QSBS. For example:<\/p>\n<ul>\n<li>The company must have been a C-corp when the stock was first issued.<\/li>\n<li>The stock must be held for at least 5 years before sale.<\/li>\n<li>The company must have had less than $75 million in assets at the time of issuing the stock.<\/li>\n<\/ul>\n"},{"acf_fc_layout":"content_highlight","highlight_type":"tip","background_colour":"blue","show_icon":true,"content":"Our <a href=\"https:\/\/seedlegals.com\/us\/resources\/qsbs-for-founders\/\" target=\"_blank\" rel=\"noopener\">QSBS guide for founders<\/a> goes over the full conditions to qualify for QSBS.","link":null},{"acf_fc_layout":"text","text":"<p>To benefit from QSBS, you have to be a C-corp. But starting as an LLC can potentially boost your tax savings.<\/p>\n<p>Let\u2019s break it down.<\/p>\n<h2>How does starting as an LLC boost your tax savings?<\/h2>\n<p>Most startups incorporate as a C-corp right away. This is typical if you\u2019re planning on raising venture capital.<\/p>\n<p>But some founders start as an LLC first for tax flexibility.<\/p>\n<p>Why? Because LLCs pass losses through to the owners\u2019 tax returns, which can be useful in the early years when a business is unprofitable.<\/p>\n<p>Later, if the company is growing and still under the $75 million asset threshold, it can convert to a C-corp and issue QSBS-eligible stock.<\/p>\n"},{"acf_fc_layout":"content_highlight","highlight_type":"tip","background_colour":"blue","show_icon":true,"content":"We\u2019ve written a guide on <a href=\"https:\/\/seedlegals.com\/us\/resources\/how-to-convert-your-llc-into-a-c-corp\/\" target=\"_blank\" rel=\"noopener\">converting your LLC into a C-corp.<\/a> Plus, in the article, we cover the difference between the two structures.","link":""},{"acf_fc_layout":"text","text":"<p>Starting as an LLC means:<\/p>\n<ol>\n<li>First, as an LLC, you may be able to offset early losses against your personal income.<\/li>\n<li>Then, you can convert to a C-corp, just before crossing $75 million in assets.<\/li>\n<li>At that point, the 10x basis rule applies to <strong>the company\u2019s fair market value at the time of conversion<\/strong>, not the initial LLC value.<\/li>\n<\/ol>\n<p>If you time this correctly, this can supercharge your QSBS tax exemption as you build value as an LLC, which acts as your base for the 10x basis rule.<\/p>\n<p>So, theoretically if you convert just as your valuation hits $75 million (but before it exceeds it), under the 10x basis rule, you can get <strong>up to $500 million in federal tax relief.<\/strong><\/p>\n<p>Just know that the gains on that stock before the conversion won\u2019t qualify for QSBS.<\/p>\n<p>For example, say you own 100 units in an LLC, which grow in value to $5 million. Then, the LLC converts to a C-corporation. After the conversion, the company grows further and your stock is sold for $20 million. In this case, QSBS could apply to the $15 million gain that accrued after the conversion, but not to the initial $5 million from when the company was an LLC.<\/p>\n<h2>How one founder set up a $400 million tax-free exit<\/h2>\n<p>Here\u2019s an interesting example we saw shared on X (<a href=\"https:\/\/x.com\/ankurnagpal\/status\/1854184512336363763\" target=\"_blank\" rel=\"noopener\">via @ankurnagpal<\/a>). It\u2019s a useful illustration of how this works:<\/p>\n<ul>\n<li>The founder\u2019s startup began as an LLC. The business grew and reached a valuation of $40 million.<\/li>\n<li>Then, they converted the LLC to a C-corp. At this point, the company issued QSBS-eligible shares to the LLC members. Since the asset value is $40 million, the 10x basis rule means the founder could later exclude up to $400 million in capital gains.<\/li>\n<li>Five years later, the company exited for $500 million. Because of the 10x basis rule, the first $400 million was fully exempt from federal capital gains tax under QSBS.<\/li>\n<\/ul>\n<p>The result? No federal capital gains tax on $400 million, potentially saving the founder over $80 million in taxes.<\/p>\n<h2>Should I use this strategy in my company?<\/h2>\n<p>While this tax incentive is big, it\u2019s not right for every startup.<\/p>\n<p>Here\u2019s why:<\/p>\n<ul>\n<li><strong>It\u2019s difficult to time correctly:<\/strong> The QSBS rules require you to convert before exceeding $75 million in assets. If your startup grows too fast, you might miss the window.<\/li>\n<li><strong>You must hold the stock for 5 years post-conversion:<\/strong> The 5-year holding period resets when you convert to a C-corp. If you exit sooner, you won\u2019t get the QSBS benefits. A 3 year holding period would provide 50% exclusion, whilst a 4 year holding period would provide 75% exclusion. These updated QSBS rules generally apply to stock issued after July 4, 2025.<\/li>\n<li><strong>Most venture capitalists won\u2019t invest in LLCs:<\/strong> VCs typically require startups to be C-corps from day one. If you\u2019re planning to raise funding from VCs, this strategy might not be realistic.<\/li>\n<\/ul>\n<p>So, who is this strategy useful for?<\/p>\n<p>Well, it\u2019s probably best for bootstrapped or angel-funded startups that can delay converting to a C-corp until they\u2019ve grown a lot, and that can scale up close to the $50 million valuation threshold without raising a lot of venture investment.<\/p>\n<p>If you\u2019re thinking about this strategy, make sure you get professional tax and legal advice first. A small mistake could cost you millions in lost tax benefits.<\/p>\n<h2>Get your company investment-ready<\/h2>\n<p>Choosing the right company structure can impact your fundraising, investment opportunities and future exit. Whether you&#8217;re looking to attract investors, issue shares or plan for long-term growth, we\u2019ve got you covered.<\/p>\n<p>Book a call below or <a href=\"https:\/\/app.seedlegals.com\/signup\" target=\"_blank\" rel=\"noopener\">start your 7-day free trial today.<\/a><\/p>\n"},{"acf_fc_layout":"form","layout":"custom","heading":"Get answers fast, for free","content":"Bring all your questions, we\u2019ve got the answers!\r\nWe\u2019ll match you with the right specialist.","custom":{"image":false,"button_text":"Get Started","form":{"type":"hubspot","hubspot_form":{"layout":"default","hide_founderinvestor_toggle":false,"default_community":"founder","custom_form_id":"21723609-6f1b-45c0-9691-77d462dc3bed","gdpr_disclaimer":"By subscribing, you agree to receive information from SeedLegals. You can unsubscribe anytime. View our <a href=\"\/us\/privacy-policy\/\" target=\"_blank\" rel=\"noopener noreferrer\">privacy policy<\/a>"},"custom":{"embed":""},"gtm_form_type":"default","gtm_form_location":"default"}},"add_shadow":false}],"has_sources":false,"related_posts":false},"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v28.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>How to get up to $500M in federal tax relief | SeedLegals<\/title>\n<meta name=\"description\" content=\"Learn how QSBS can help founders save huge amounts in tax. 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