QSBS, Solved

In this episode, host Brady Weller chats with Brad Dillon about how founders can leverage Section 1202 (Qualified Small Business Stock (QSBS)) to optimize their equity tax strategy long before an exit. Brad Dillon is a partner on the a16z Perennial team (Andreessen Horowitz), where he advises founders on tax, trust, and estate planning. His work focuses on issues that arise throughout the founder journey, including QSBS, equity compensation, pre-liquidity planning, concentrated stock, charitable giving, and transferring wealth to future generations. Before joining a16z Perennial, Brad advised ultra-high-net-worth families at UBS on tax, estate planning, and philanthropy. He began his career in private practice, most recently in Milbank’s trusts and estates department in New York. The conversation unpacks critical founder tax topics, detailing how the Section 1202 QSBS exclusion incentivizes venture capital investments in high-risk, pre-commercial startups. Brady and Brad examine how to avoid severe tax hits (such as the 37%+ tax shock on Series A secondary share sales) while navigating state-level QSBS eligibility rules in high-tax states like California and New York. They also cover practical equity strategy, from filing timely 83(b) elections to executing QSBS stacking and preparing for IRS guidance on trust planning and QSBS Rollovers. Whether you are optimizing your cap table or structuring a tax-free exit strategy, this episode provides a roadmap for preserving founder equity value and keeping capital in the startup ecosystem. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, host Brady Weller sits down with Blaine Woodson, Manager in Grant Thornton's National Tax Office and a leading QSBS subject matter expert, to break down how and why companies convert from S-Corp to C-Corp to unlock Section 1202 benefits. They cover the safest way to structure a conversion (the "assets-down" method), how pre-contribution built-in gain under Section 1202(i) affects your exclusion at exit, and the business drivers pushing founders toward C-Corp form, from raising outside capital to FDII benefits on cross-border IP sales. Blaine also shares real client examples, including a bifurcated tech-and-real-estate structure and a conversion projected to save $35 million in federal tax over five years.📍 Join Blaine and Brady at the 2026 QSBS Summit in Jackson Hole this September — registration closes August 1.Register here: https://www.qsbsrollover.com/summit Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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.

📍 Learn more about the 2026 QSBS Summit in Jackson Hole, WY: https://www.qsbsrollover.com/summitBrady sits down with Doug Brody, President of Symphony Tax at Symphony Risk Solutions, to break down everything founders, investors, and advisors need to know about tax insurance as it relates to Section 1202 (QSBS) planning.The content of this program is intended for informational purposes only and does not constitute tax, legal, or investment advice. Views represented by guests and hosts are not always representative of their affiliated organizations. Topics covered in this episode:What tax insurance actually is and how it works (it's not compulsory, it's issue-specific, and it's a one-time premium)Why QSBS is such fertile ground for tax insurance given the gray areas in the lawThe difference between "substantial authority," "more likely than not," and "should" level tax opinions — and why insurers require a higher bar than what's needed just to avoid penaltiesWhat actually gets covered: cash tax exposure, interest, audit defense costs, and gross-up for income taxes on claim proceedsReal numbers: how premiums are priced (roughly 10% for a single individual with a $10M exemption, dropping to 6-7% as more investors or larger exemptions are pooled together), inclusive of the premium, the underwriting fees, and tax opinion.Why documentation and diligence matter long before a transaction closes — and how to clean up "imperfect" historical factsHow Doug and his team act as a buffer between clients and underwriters to streamline the processAdvice for founders and investors who aren't sure if they even need insurance yetWhether you're a founder eyeing a secondary sale, a full exit, or a rollover, or an advisor helping clients navigate Section 1202, this conversation offers a practical, real-world look at how tax insurance can turn uncertainty into peace of mind. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 episode of "QSBS, Solved", is the last part of a 5-episode series called "QSBS Masterclass", where Brady Weller discusses QSBS with tax attorney and prolific QSBS expert, Scott Dolson. Scott is a Partner at FBT Gibbons and is the leader of the firm’s tax planning team and co-chair of the firm’s private equity industry team.  The scope of Scott’s tax practice encompasses tax planning for business formations, ownership arrangements, LLC agreements and M&A transactions.  Scott’s corporate practice extends to handling M&A transactions, equity compensation arrangements and general corporate law matters.Scott has written dozens of long-form articles and thousands of pages on QSBS, QSBS planning, and opined on the nuances of Section 1202 and Section 1045. In this series we use some of Scott's most foundational articles as jumping off points for our conversation. This Part 5 episode is based on Scott's article titled, "Planning for the Sale of Qualified Small Business Stock (QSBS)". You can find the article online at the link below:Scott's Bio: https://fbtgibbons.com/people/scott-dolson/Brady's LinkedIn: https://www.linkedin.com/in/brady-weller/Article Link: https://fbtgibbons.com/planning-for-the-sale-of-qualified-small-business-stock-qsbs/#Section3Video Link: https://youtu.be/CS_LDXZsO-A Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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.

On this week's episode of QSBS, Solved, Brady sits down with tax attorney, Mark Melton. Mark is a Partner working out of Holland & Knight's Dallas office and serves as the co-chair of the Tax, Executive Compensation and Benefits Practice Group. He focuses on federal income taxation issues related to domestic and international transactions of private equity and hedge funds, as well as other investment partnerships, joint ventures, real estate investment trusts (REITs) and operating businesses.In this episode we discuss how Mark thinks about "risk" and uncertainty around tax positions and how he helps clients make sense of various planning opportunities.  Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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.

On this week's episode of QSBS, Solved, Brady sits down with Dr. Daniel Gilham to talk about dramatic shifts in wealth management and the unique needs of founders and business owners. Daniel is the Managing Director of Advisor Strategy at Farther, the 2025 Inc 5000 fastest growing financial services company in the country. The fintech company is transforming the wealth management landscape by leveraging technology with human experience and expertise. He has 17 years of experience serving business owners, institutions, and high-net-worth clients through goals-based financial planning and wealth management solutions.Read more on Daniel: https://www.farther.com/advisor/daniel-gilham Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 episode of "QSBS, Solved", is part of a 5-episode series called "QSBS Masterclass", where Brady Weller discusses QSBS with tax attorney and prolific QSBS expert, Scott Dolson. Scott is a Partner at Frost Brown Todd and is the leader of the firm’s tax planning team and co-chair of the firm’s private equity industry team.  The scope of Scott’s tax practice encompasses tax planning for business formations, ownership arrangements, LLC agreements and M&A transactions.  Scott’s corporate practice extends to handling M&A transactions, equity compensation arrangements and general corporate law matters.Scott has written dozens of long-form articles and thousands of pages on QSBS, QSBS planning, and opined on the nuances of Section 1202 and Section 1045. In this series we use some of Scott's most foundational articles as jumping off points for our conversation. This Part 4 episode is based on Scott's article titled, "Conversions, Reorganizations, Recapitalizations, Exchanges and Stock Splits Involving Qualified Small Business Stock". You can find the article online at the link below:Scott's Bio: https://fbtgibbons.com/people/scott-dolson/Brady's LinkedIn: https://www.linkedin.com/in/brady-weller/Article Link: https://frostbrowntodd.com/conversions-reorganizations-recapitalizations-exchanges-and-stock-splits-involving-qualified-small-business-stock-qsbs/Video Link: https://youtu.be/L_kbh1Etiiw Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 episode of "QSBS, Solved", is part of a 5-episode series called "QSBS Masterclass", where Brady Weller discusses QSBS with tax attorney and prolific QSBS expert, Scott Dolson. Scott is a Partner at Frost Brown Todd and is the leader of the firm’s tax planning team and co-chair of the firm’s private equity industry team.  The scope of Scott’s tax practice encompasses tax planning for business formations, ownership arrangements, LLC agreements and M&A transactions.  Scott’s corporate practice extends to handling M&A transactions, equity compensation arrangements and general corporate law matters.Scott has written dozens of long-form articles and thousands of pages on QSBS, QSBS planning, and opined on the nuances of Section 1202 and Section 1045. In this series we use some of Scott's most foundational articles as jumping off points for our conversation. This Part 3 episode is based on Scott's article titled, "Substantiating the Right to Claim QSBS Tax Benefits". You can find the article online at the link below:Scott's Bio: https://fbtgibbons.com/people/scott-dolson/Brady's LinkedIn: https://www.linkedin.com/in/brady-weller/Article Links: Part 1: https://frostbrowntodd.com/substantiating-the-right-to-claim-qsbs-tax-benefits-part-1/Part 2: https://frostbrowntodd.com/substantiating-the-right-to-claim-qsbs-tax-benefits-part-2/Video Link: https://youtu.be/pRhIiSt8iYI Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 episode of "QSBS, Solved", is part of a 5-episode series called "QSBS Masterclass", where Brady Weller discusses QSBS with tax attorney and prolific QSBS expert, Scott Dolson. Scott is a Partner at Frost Brown Todd and is the leader of the firm’s tax planning team and co-chair of the firm’s private equity industry team.  The scope of Scott’s tax practice encompasses tax planning for business formations, ownership arrangements, LLC agreements and M&A transactions.  Scott’s corporate practice extends to handling M&A transactions, equity compensation arrangements and general corporate law matters.Scott has written dozens of long-form articles and thousands of pages on QSBS, QSBS planning, and opined on the nuances of Section 1202 and Section 1045. In this series we use some of Scott's most foundational articles as jumping off points for our conversation. This Part 2 episode is based on Scott's article titled, "Finding Suitable Replacement Qualified Small Business Stock (QSBS) – A Section 1045 Primer". You can find the article online at the link below:Scott's Bio: https://fbtgibbons.com/people/scott-dolson/Brady's LinkedIn: https://www.linkedin.com/in/brady-weller/Article Link: https://frostbrowntodd.com/finding-suitable-replacement-qualified-small-business-stock-qsbs-a-section-1045-primer/Video Link: https://youtu.be/nY_dbehTqPY Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 episode of "QSBS, Solved", is part of a 5-episode series called "QSBS Masterclass", where Brady Weller discusses QSBS with tax attorney and prolific QSBS expert, Scott Dolson. Scott is a Partner at Frost Brown Todd and is the leader of the firm’s tax planning team and co-chair of the firm’s private equity industry team.  The scope of Scott’s tax practice encompasses tax planning for business formations, ownership arrangements, LLC agreements and M&A transactions.  Scott’s corporate practice extends to handling M&A transactions, equity compensation arrangements and general corporate law matters.Scott has written dozens of long-form articles and thousands of pages on QSBS, QSBS planning, and opined on the nuances of Section 1202 and Section 1045. In this series we use some of Scott's most foundational articles as jumping off points for our conversation. This Part 1 episode is based on Scott's article titled, "Maximizing Section 1202’s Gain Exclusion". You can find the article online at the link below:Scott's Bio: https://fbtgibbons.com/people/scott-dolson/Brady's LinkedIn: https://www.linkedin.com/in/brady-weller/Article Link: https://frostbrowntodd.com/maximizing-the-section-1202-gain-exclusion-amount/Video Link: https://youtu.be/QnK3b71Nlvo Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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", Brady Weller talks with CJ Stermetz, founder of Equity for the Win (EquityFTW), about the world of employee equity compensation, from startup stock options to RSUs at public tech giants. Together they unpack how to evaluate option grants, when it might make sense to exercise, how RSUs are taxed, and why under-withholding can derail a tax plan.They also explore real-world liquidity events, like acquisitions and IPOs, and how founders and early employees can use QSBS to potentially eliminate millions in taxes. Whether you’re starting or joining your first startup, transitioning from Google to a private company, or sitting on a pile of vested shares, this episode will help you see the bigger picture behind your comp package and plan smarter for the upside.Featuring: CJ Stermetz, CFP®, CEP,  founder of EquityFTW — an advice-only financial planning firm for tech employees navigating complex compensation.Online at: https://www.equityftw.com/ Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady sits down with QSBSrollover.com Co-founder and CEO, Nick King, to talk about how founders discover, learn about, and ultimately leverage QSBS. The two retrace their early startup days, unpack how a simple “look into this” became a deep dive into one of the most overlooked tax advantages in the U.S., and explain why they believe founders are among the best capital allocators in the world. They share how their team helps some of the most successful founders in the country build businesses that enhance and expand the QSBS benefit. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady Weller discusses valuation services with Evan Levine and Nainesh Shah from Complete Advisors. They explore the importance of valuation for startups at various stages, the methodologies used in valuation, and the critical role of industry analysis. The conversation delves into the complexities of valuing early-stage companies, the significance of customer-based corporate valuation, and the necessity of justifying valuations to the IRS. They also discuss how to choose the right valuation analyst and the potential financial benefits of accurate valuations.Learn more about Complete Advisors: https://completeadvisors.com/ Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady sits down with Brian Lamb, founder and CEO of Promissory (promissory.com), to explore one of the most powerful  strategies in founder tax planning: QSBS trust stacking. Brian shares his journey from co-founding the estate-planning platform Trust & Will to launching Promissory, a platform that helps founders easily establish Nevada-based irrevocable trusts for QSBS optimization without the heavy legal overhead. Promissory is the modern trust and estate platform built for QSBS.The conversation dives into the mechanics and timing of trust creation, why early planning is crucial, and how founders can multiply their QSBS exemptions through properly structured trusts. Brady and Brian walk through real-world examples of exits, valuation considerations, and the nuances of gifting, estate exemptions, and state tax advantages. They also compare trust stacking to QSBS rollovers, discussing when each strategy shines and how they can work together to completely eliminate capital gains on multi-million-dollar exits. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, host Brady Weller sits down with Itamar Novick (General Partner, Recursive Ventures) and Aaron Rosenson (co-founder, Aption) to examine the brutal concentration risk founders carry when building startups. We get specific on the mechanics that drive startup outcomes, liquidation preferences, participation, and how to negotiate term sheets with founder and employee alignment in mind. Itamar shares how he has helped companies raise their next rounds and why many great businesses shouldn’t take venture money at all, drawing on lessons from Life360’s long road to IPO and his running “VC horror stories.”Aaron then introduces Aption’s cash-free equity pooling: a way for founders to "swap" a slice of paper wealth for a diversified basket of similarly promising companies, adding real downside protection without dulling ambition or misaligning incentives. The trio contrasts this with traditional secondaries, talks through pool risk profiles, and closes with a clear decision lens for early teams: bootstrap, venture, debt, or a blend—only if the opportunity is truly venture-scale. If you care about founder liquidity, rational risk, and alignment that actually survives market cycles, this conversation is a field guide.Check out Aption: https://aption.com/Learn more about Recursive Ventures: https://www.recursiveventures.com/Itamar: https://www.linkedin.com/in/itamarnovick/Aaron: https://www.linkedin.com/in/aaron-rosenson-5875a62a/ Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady chats with attorney Scott Dolson of Frost Brown Todd LLP. Scott is a leading voice on QSBS and has written extensively about all aspects of Section 1202 and Section 1045, which describe QSBS and QSBS Rollovers. In this conversation, Scott shares about opportunities and challenges related to substantiating/documenting QSBS, meeting the trade/business requirements, and the gross asset limits. You can find Scott here: https://frostbrowntodd.com/people/scott-dolson/LinkedIn: https://www.linkedin.com/in/scott-dolson-811699158/ Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady sits down with Mat Sherman, founder of Arena, a new platform designed to give early-stage founders a transparent and structured path into the venture capital ecosystem. Arena offers a unique leaderboard system that tracks founders’ weekly progress, engagement, and credentials, ultimately helping them earn introductions to investors. For just $20 a month, founders can access AMAs, office hours, and a community designed to accelerate their learning curve from years down to months—while also holding them accountable for tangible progress.Mat shares his journey, from Seed Scout to Product Hunt, to launching Arena, and why he believes the startup world is “seemingly inclusive, but explicitly exclusive.” He breaks down what makes a founder “fundable,” the balance between technical ability, high-context industry knowledge, and the all-important vibe check. The conversation also explores the tension between bootstrapping and venture funding, and how Arena aims to open the front door of VC to more founders—without the hype, just results.Arena: https://arena.matsherman.com/Mat's X Account: https://x.com/mat_sherman Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady sits down with Mark Leeds, tax partner at Pillsbury Winthrop Shaw Pittman LLP in New York, to unpack how startups can leverage tax incentives to attract private capital. From the mechanics of Qualified Small Business Stock (QSBS) to the advantages of operating as a C-Corporation, Mark explains why the “double tax” concern is no longer the obstacle many entrepreneurs think it is, and how founders can use these structures to reinvest more into their businesses while setting themselves up for meaningful tax exemptions at exit.The conversation goes beyond QSBS to cover other critical incentives: Qualified Business Income deductions, bonus depreciation, R&D expense treatment, and Qualified Opportunity Funds (QOFs). Mark highlights how these tools not only reduce tax burdens but also serve as powerful signals to investors. For founders raising capital, integrating these benefits into pitch materials can create confidence, enhance after-tax returns, and turn even modest wins into compelling outcomes.You can find Mark and his team at Pillsbury, here: https://www.pillsburylaw.com/en/lawyers/mark-leeds.htmlMark's LinkedIn: https://www.linkedin.com/in/mark-leeds-05648a3/ Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady is joined by Alex Shartsis, CEO of Silverwood and founder of Skyp.ai. Alex brings a rare blend of experience advising founders on growth, go-to-market strategy, and M&A, while also building and scaling his own ventures. Together, they dive into the realities of scaling a company toward an exit, how to think about dilution and valuations, and why building a strong go-to-market motion is the foundation of successful M&A outcomes. You can also find a link to Alex’s Seed to Sequoia newsletter below these episode notes.Alex also shares lessons from his own founder journey, including what makes or breaks a deal, the dangers of focusing too much on tax optimization at the wrong stage, and how AI is reshaping both outbound sales and acquisition strategy. Newsletter: https://seedtosequoia.silverwood.ai/subscribe Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady is joined by Jonathan Fish, CEO of Cap Gains Inc. and founder of QSBSEXPERT.com. Jonathan shares how his experience as a CPA working with private equity and venture funds led him to build one of the most trusted resources on Qualified Small Business Stock. He explains the gaps he saw in both education and advisory support, and how those gaps shaped his decision to launch tools and services that help shareholders, founders, and funds make the most of QSBS.The conversation covers common pitfalls that put eligibility at risk, from structuring mistakes and equity issuance problems to challenges around data collection at exit. Jonathan outlines how Cap Gains works with venture funds and their partners to anticipate tripwires, prepare documentation, and identify opportunities such as rollovers and exit planning strategies. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady sits down with tax attorney Chris Karachale of Hanson Bridgett to unpack a few misunderstood components of Qualified Small Business Stock (QSBS). They discussed the practical realities of opinion letters and audit defense and the latest OBBBA updates on exclusion limits and gross asset thresholds.The conversation dives into:QSBS opinion letters — what they actually do (and don’t do), and why they serve as more of a penalty shield and documentation tool than a guarantee.OBBBA changes — how raising the exclusion and gross asset caps reshapes opportunities for founders, early employees, and venture funds.The SAFE debate — whether Simple Agreements for Future Equity should trigger QSBS holding periods, and the practical implications for early-stage investors. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 episode originally appeared on the Teaching Tax Flow podcast, hosted by Chris Picciurro, CPA, and John Tripolsky. We've adapted it a bit for our platform and are excited to share the context with you all. Thanks to John and Chris for the collaboration and for letting us repurpose and share the audio for our audience!In the episode, Brady Weller, of QSBSrollover.com, breaks down one of the most powerful but overlooked tax planning tools for entrepreneurs: the Qualified Small Business Stock (QSBS) exemption. The conversation covers how founders and investors can unlock millions in tax savings through Section 1202 exclusions and Section 1045 (QSBS rollovers), plus recent legislative updates that make QSBS even more attractive. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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.

On this episode of "QSBS, Solved", Brady sits down with Phil Haslett, Co-founder and Chief Strategy Officer at EquityZen. Phil shares insights on the evolution of private secondary markets, why liquidity matters for founders and employees, and how investor interest has shifted in today’s environment. The conversation also explores how QSBS benefits show up in secondary sales, the growing role of institutional investors in private markets, and practical advice for founders navigating exits and liquidity. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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, Brady Weller sits down with Andrew Gazdecki, founder of Acquire.com, to talk about his journey through multiple exits, from a $50K college side project to building Business Apps into a $10M ARR company. Andrew shares why most acquisitions are far smaller than the billion-dollar headlines, how founders can maximize their odds of success, and the role QSBS played in his own deal structure. They discuss the rise of solo founders, the real impact of AI on early-stage businesses, and what sellers can do to prepare for a smooth, high-value exit. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 special episode, originally recorded as a webinar ("Understanding OBBBA’s Section 1202 Revisions"), we dive deep into the tax implications of the "One Big Beautiful Bill Act" (OBBBA) and its sweeping changes to Section 1202 and Qualified Small Business Stock (QSBS).Brian Masterson and Scott Dolson, partners at Frost Brown Todd, are joined by Brady Weller, Director at QSBSrollover.com, to unpack the three most consequential updates to Section 1202:A new tiered holding period structure (3-, 4-, and 5-year exclusions)An increase in the QSBS exclusion cap from $10 million to $15 million (plus inflation indexing)A raise in the aggregate gross asset limit from $50 million to $75 millionThe discussion addresses how these changes will impact tax planning for founders, investors, and advisors—especially in light of effective dates, rollover strategies under Section 1045, and the increased importance of entity structuring. The panel also discusses potential IRS scrutiny around restructuring tactics and outlines emerging opportunities stemming from these new rules.Whether you're a startup founder, investor, or tax advisor, this episode offers practical takeaways and expert insight into the future of QSBS planning under the new regime.Special thanks to the team at Frost Brown Todd for inviting us to collaborate and for allowing us to use the audio from the session on our podcast feed. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 episode is about bringing value to founders. If you're new to startup valuation, or even if you're not, this conversation with Dan Eyman of Meld Valuation breaks down the key principles every founder should understand. We cover when a valuation is needed, common pitfalls and questions, how to evaluate which firm to go with, and more. Whether you're raising your first round or preparing for an exit, this episode is packed with practical insights to help you approach valuation, fundraising, and financial compliance with clarity and confidence. Contact: [email protected] | www.QSBSrollover.comDisclaimer: 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 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.comDisclaimer: 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.

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.comDisclaimer: 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.comDisclaimer: 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.

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.comDisclaimer: 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.comDisclaimer: 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.comDisclaimer: 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.comDisclaimer: 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.