QSBS, Solved

In this episode of QSBS, Solved , host Brady Weller sits down with Myra Sutanto Shen, a tax partner and head of the tax practice group at Wilson Sonsini, to unpack the complex world of Qualified Small Business Stock (QSBS) eligibility for the health, life sciences, and biotech sectors. Myra sheds light on the stark differences between traditional tech startups and capital-intensive biotech compani...

On this episode of QSBS, Solved , host Brady Weller sits down with VJ Occhino, partner and National VC Tax Sector Leader at PwC, to tackle the five QSBS questions VC clients ask most. They discuss whether splitting a funding round can keep a company under the gross asset limit, and why timing and independent terms matter. They explain why warrants, options, and SAFEs may not start your QSBS holdin...

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...

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 ga...

📍 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...

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 t...

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 a...

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...

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 p...

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 p...

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 p...

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 p...

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 al...

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 ca...

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-bas...

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 trust...

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...

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 requireme...

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, fou...

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 entre...

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...

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 decisi...

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...

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 t...

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...