QSBS, Solved

Not every startup can tap into the huge tax advantages of Qualified Small Business Stock (QSBS), and in this episode, we’re breaking down exactly why. Join us as we unpack Section 1202 of the tax code and spotlight all the types of businesses that don’t qualify for QSBS, including law firms, healthcare providers, consulting companies, finance, hospitality, and more. If you’re building a business or planning a QSBS rollover, knowing these exclusions can save you from making a costly mistake.

We’ll walk through what the IRS means by “excluded activities,” explain the active business requirements, and clear up common misconceptions, like whether consulting or software businesses are really in the danger zone. If you want to know whether your business is QSBS-eligible before your next big exit, this episode gives you the practical breakdown founders, investors, and advisors need.

If you’re in the startup world and looking to maximize your QSBS benefits, this is a must-listen.

Contact: [email protected] | www.QSBSrollover.com

Disclaimer: This podcast is for general informational and educational purposes only and does not constitute tax, legal, financial, investment, or other professional advice. The discussion reflects the personal views and experiences of the speakers as of the date of recording and may not reflect current law, regulations, or IRS guidance, which are subject to change. Nothing in this episode should be relied upon as advice for any specific situation. The implementation of Section 1202 (QSBS) rules and impacts are highly fact-specific and depend on individual circumstances; listeners should not act or refrain from acting based on this content without first consulting a qualified tax advisor, attorney, or other professional regarding their particular facts and circumstances. The host, the guest, and their respective affiliated firms disclaim any liability arising from reliance on the information presented in this episode.

Brady Weller and Mark Cecchini discuss wealth planning strategies and tax savings opportunities (via QSBS) that founders need to consider when experiencing a liquidity event.

Contact: [email protected] | www.QSBSrollover.com

Disclaimer: This podcast is for general informational and educational purposes only and does not constitute tax, legal, financial, investment, or other professional advice. The discussion reflects the personal views and experiences of the speakers as of the date of recording and may not reflect current law, regulations, or IRS guidance, which are subject to change. Nothing in this episode should be relied upon as advice for any specific situation. The implementation of Section 1202 (QSBS) rules and impacts are highly fact-specific and depend on individual circumstances; listeners should not act or refrain from acting based on this content without first consulting a qualified tax advisor, attorney, or other professional regarding their particular facts and circumstances. The host, the guest, and their respective affiliated firms disclaim any liability arising from reliance on the information presented in this episode.

In this episode of QSBS, Solved, we break down why Qualified Small Business Stock (QSBS) isn’t just for Silicon Valley tech founders. Using the recent Chobani acquisition of Daily Harvest as a real-world case study, we highlight how early shareholders and founders outside of tech—like those in consumer brands, food, beverage, and direct-to-consumer startups—can unlock millions in tax-free gains if they plan smart with QSBS.

We walk through what it takes to qualify for QSBS, how non-tech companies like Daily Harvest can meet the requirements, and what founders and investors should be doing now to maximize this powerful tax benefit. If you’re building or backing a high-growth startup in any sector, don’t miss this practical guide to one of the startup world’s best-kept secrets.

Contact: [email protected] | www.QSBSrollover.com

Disclaimer: This podcast is for general informational and educational purposes only and does not constitute tax, legal, financial, investment, or other professional advice. The discussion reflects the personal views and experiences of the speakers as of the date of recording and may not reflect current law, regulations, or IRS guidance, which are subject to change. Nothing in this episode should be relied upon as advice for any specific situation. The implementation of Section 1202 (QSBS) rules and impacts are highly fact-specific and depend on individual circumstances; listeners should not act or refrain from acting based on this content without first consulting a qualified tax advisor, attorney, or other professional regarding their particular facts and circumstances. The host, the guest, and their respective affiliated firms disclaim any liability arising from reliance on the information presented in this episode.

Claim QSBS when you sell secondary as part of a funding round.

QSBS rollovers can bridge the holding period gap to 5 years for founders selling stock "early".

AI company raising a large amount of funding early one? We're in a unique moment that is going to unlock billions in tax savings using QSBS Rollovers.

Contact: [email protected] | www.QSBSrollover.com

Contact: [email protected] | www.QSBSrollover.com

Disclaimer: This podcast is for general informational and educational purposes only and does not constitute tax, legal, financial, investment, or other professional advice. The discussion reflects the personal views and experiences of the speakers as of the date of recording and may not reflect current law, regulations, or IRS guidance, which are subject to change. Nothing in this episode should be relied upon as advice for any specific situation. The implementation of Section 1202 (QSBS) rules and impacts are highly fact-specific and depend on individual circumstances; listeners should not act or refrain from acting based on this content without first consulting a qualified tax advisor, attorney, or other professional regarding their particular facts and circumstances. The host, the guest, and their respective affiliated firms disclaim any liability arising from reliance on the information presented in this episode.

Michael Arlein, Partner at Patterson Belknap Webb & Tyler, and Brady Weller of QSBSrollover.com share insights on preserving wealth and optimizing tax outcomes during high-growth exits. This episode is ideal for startup founders, advisors, and anyone navigating QSBS-related planning and the use of trusts.

The conversation revolves around trust and estate planning for startup founders, particularly in the context of achieving liquidity events and maximizing tax benefits. Michael delves into various strategies including QSBS stacking, rollovers, and different trust structures such as the GOAT trust and charitable remainder trusts. The discussion highlights the critical timing for setting up estate planning structures, especially concerning the value of shares and potential exits. The conversation touches on practical concerns such as control, liquidity, and the provisions for family beneficiaries. Whether you're a single founder or have a family, these insights aim to help you strategize for your long term tax-savings and financial planning effectively.

Visit the Founder Focus Resource Center which Michael runs:

https://www.pbwt.com/founder-focus-resource-center

Contact: [email protected] | www.QSBSrollover.com

Disclaimer: This podcast is for general informational and educational purposes only and does not constitute tax, legal, financial, investment, or other professional advice. The discussion reflects the personal views and experiences of the speakers as of the date of recording and may not reflect current law, regulations, or IRS guidance, which are subject to change. Nothing in this episode should be relied upon as advice for any specific situation. The implementation of Section 1202 (QSBS) rules and impacts are highly fact-specific and depend on individual circumstances; listeners should not act or refrain from acting based on this content without first consulting a qualified tax advisor, attorney, or other professional regarding their particular facts and circumstances. The host, the guest, and their respective affiliated firms disclaim any liability arising from reliance on the information presented in this episode.

This is the audio recording for our recent LinkedIn Live event from June 17th 2025 where Mark Cecchini, CFP®, CCFC of Quadrant Capital and Brady Weller of QSBSrollover.com dive into Post-Exit Planning and QSBS Rollovers for Founders.

Learn how to maximize tax savings and reinvest strategically after a liquidity event.

Contact: [email protected] | www.QSBSrollover.com

The audio from our recent LinkedIn Live event on June 17th featuring Mark Cecchini, CFP®, CCFC of Quadrant Capital and Brady Weller of QSBSrollover.com. They dove into post-exit planning and QSBS Rollovers for founders.

Learn how to maximize tax savings and reinvest strategically after a liquidity event.

Contact: [email protected] | www.QSBSrollover.com

Not every startup can tap into the huge tax advantages of Qualified Small Business Stock (QSBS), and in this episode, we’re breaking down exactly why. Join us as we unpack Section 1202 of the tax code and spotlight all the types of businesses that don’t qualify for QSBS, including law firms, healthcare providers, consulting companies, finance, hospitality, and more. If you’re building a business or planning a QSBS rollover, knowing these exclusions can save you from making a costly mistake.

We’ll walk through what the IRS means by “excluded activities,” explain the active business requirements, and clear up common misconceptions, like whether consulting or software businesses are really in the danger zone. If you want to know whether your business is QSBS-eligible before your next big exit, this episode gives you the practical breakdown founders, investors, and advisors need.

If you’re in the startup world and looking to maximize your QSBS benefits, this is a must-listen.

Contact: [email protected] | www.QSBSrollover.com

This episode of QSBS, Solved is a repost of an interview featuring Brady Weller, Director of QSBSrollover.com, conducted by Earnest Sweat of Swimming with Allocators. SWA is a podcast delving into the strategies and perspectives of leading allocators in the VC space. Designed for fund managers and fellow allocators, the show offers a deep dive into the methodologies and approaches adopted by prominent players in the industry. The conversations are rich, and enlightening, and cover a wide range of topics relevant to the venture asset class from an LP's viewpoint.

Earnest Sweat is the Founding Partner of Public School Ventures, a dynamic syndicate of over 600 technical operators, go-to-market specialists, and LPs. Previously, Earnest built new venture capital practices at Prologis and GreatPoint Ventures. His focus is on investing in value chaintech, specifically vertical SaaS, applied AI, middleware, and B2B marketplaces, which are poised to revolutionize foundational industries like real estate, insurance and supply chain. Earnest has sourced and led investments in companies such as Flexport, Flexe, KlearNow, and Lula Insurance.

Contact: [email protected] | www.QSBSrollover.com

On today’s episode of QSBS Solved, we break down the essential facts about Qualified Small Business Stock—QSBS—and why it’s such a powerful tax-saving tool for startup founders, investors, and early employees. From the requirements for a company to issue QSBS, to the types of businesses that are excluded, we cover everything you need to know about eligibility, the $50 million asset test, the five-year holding period, and how much gain you can actually exclude. We also highlight potential pitfalls, like stock redemptions, and explain how a QSBS rollover (under Section 1045) can help you keep your tax advantage, even if you exit early.

If you want to learn how founders and shareholders in places like New York can potentially eliminate their capital gains tax bill—sometimes as high as 37%—this episode is for you. Whether you’re just hearing about QSBS for the first time or looking to refine your exit strategy, we’ll make sure you’re ready to protect your gains and maximize your upside.

Contact: [email protected] | www.QSBSrollover.com