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.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. Section 1202 (QSBS) rules 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/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 law
• The 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 penalties
• What actually gets covered: cash tax exposure, interest, audit defense costs, and gross-up for income taxes on claim proceeds
• Real 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 facts
• How Doug and his team act as a buffer between clients and underwriters to streamline the process
• Advice 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: [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. Section 1202 (QSBS) rules 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/#Section3

Video Link: https://youtu.be/CS_LDXZsO-A

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. Section 1202 (QSBS) rules 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.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. Section 1202 (QSBS) rules 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.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. Section 1202 (QSBS) rules 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.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. Section 1202 (QSBS) rules 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.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. Section 1202 (QSBS) rules 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.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. Section 1202 (QSBS) rules 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.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. Section 1202 (QSBS) rules 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.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. Section 1202 (QSBS) rules 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.