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/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.