QSBS, Solved

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. 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.com

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

In this episode of "QSBS, Solved", 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. 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.com

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

In this episode of QSBS, Solved, 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.com

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

In this episode of QSBS, Solved, 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.com

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

In this episode of QSBS, Solved, 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.com

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

In this episode of QSBS Solved, 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.com

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

In this episode of QSBS Solved, 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.com

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

In this episode of QSBS Solved, 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.html

Mark's LinkedIn: https://www.linkedin.com/in/mark-leeds-05648a3/

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

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