QSBS, Solved

QSBS Rollover (QSBSrollover.com)
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QSBS, Solved – Presented by QSBS Rollover (QSBSrollover.com) Your go-to audio source for everything Qualified Small Business Stock (QSBS). Whether you're an investor preparing for a stock sale, a founder nearing an exit, or an advisor exploring QSBS rollover strategies, this podcast delivers actionable insights you won't find anywhere else. Each episode features audio versions of our most popular articles, expert interviews, and deep dives into QSBS rules, tax planning, eligibility, and the mechanics of rollovers under Section 1202 and 1045. Hosted by the team at QSBS Rollover, we break down complex topics to help you solve QSBS – from exemptions to rollovers to real-world structuring. Contact: Brady@QSBSrollover.com

  1. Sep 2

    QSBS for Startup Founders and "Structural Alpha", with Brad Dillon (a16z)

    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: Brady@QSBSrollover.com | 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.

    QSBS for Startup Founders and "Structural Alpha", with Brad Dillon (a16z)

  2. Jul 28

    S-Corp to C-Corp: Unlocking QSBS Benefits, with Blaine Woodson

    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: Brady@QSBSrollover.com | 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.

    S-Corp to C-Corp: Unlocking QSBS Benefits, with Blaine Woodson

  3. Jul 15

    Tax Insurance and "Sleeping Well" With QSBS, with Doug Brody

    📍 Learn more about the 2026 QSBS Summit in Jackson Hole, WY: https://www.qsbsrollover.com/summit Brady 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 yet Whether 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: Brady@QSBSrollover.com | 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.

    Tax Insurance and "Sleeping Well" With QSBS, with Doug Brody

  4. Jan 13

    QSBS Masterclass Series (Part 5): Planning for the Sale of QSBS

    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/#Section3 Video Link: https://youtu.be/CS_LDXZsO-A Contact: Brady@QSBSrollover.com | 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.

    QSBS Masterclass Series (Part 5): Planning for the Sale of QSBS

  5. Jan 6

    Assessing Risk and Complexity with QSBS, Featuring Mark Melton

    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: Brady@QSBSrollover.com | 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.

    Assessing Risk and Complexity with QSBS, Featuring Mark Melton

  6. 12/30/2025

    Incentives, Asset Location, and Founder Wealth Planning, with Dr. Daniel Gilham (Farther)

    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: Brady@QSBSrollover.com | 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.

    Incentives, Asset Location, and Founder Wealth Planning, with Dr. Daniel Gilham (Farther)

  7. 12/23/2025

    QSBS Masterclass Series (Part 4): QSBS Impacts After Conversions and Reorganizations

    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: Brady@QSBSrollover.com | 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.

    QSBS Masterclass Series (Part 4): QSBS Impacts After Conversions and Reorganizations

  8. 12/16/2025

    QSBS Masterclass Series (Part 3): Substantiating and Documenting QSBS

    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: Brady@QSBSrollover.com | 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.

    QSBS Masterclass Series (Part 3): Substantiating and Documenting QSBS
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About

QSBS, Solved – Presented by QSBS Rollover (QSBSrollover.com) Your go-to audio source for everything Qualified Small Business Stock (QSBS). Whether you're an investor preparing for a stock sale, a founder nearing an exit, or an advisor exploring QSBS rollover strategies, this podcast delivers actionable insights you won't find anywhere else. Each episode features audio versions of our most popular articles, expert interviews, and deep dives into QSBS rules, tax planning, eligibility, and the mechanics of rollovers under Section 1202 and 1045. Hosted by the team at QSBS Rollover, we break down complex topics to help you solve QSBS – from exemptions to rollovers to real-world structuring. Contact: Brady@QSBSrollover.com

Information

  • Creator
    QSBS Rollover (QSBSrollover.com)
  • Years Active
    2025 - 2026
  • Episodes
    33
  • Rating
    Clean
  • Copyright
    © 2026 QSBS, Solved
  • Show Website
    QSBS, Solved

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