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. Sco...

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. Sco...

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. Sco...

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. Sco...

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 ...

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 founder...

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 h...

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 ...

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 ...

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/...

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 fr...

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 busines...

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 a strong go-to-market motion is the foundation of successful M&A outcomes. You can also find a...

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 decision to launch tools and services that help shareholders, founders, and funds make the most of QSBS....

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 actually do (and don’t do), and why they serve as more of a penalty shield and documentation tool ...

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 the most powerful but overlooked tax planning tools for entrepreneurs: the Qualified Small Business Sto...

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 role of institutional investors in private markets, and practical advice for founders navigating exits and...

In this episode of QSBS Solved, Brady Weller sits down with Andrew Gazdecki, founder of Acquire.com, to talk about his journey through multiple exits, from a $50K college side project to building Business Apps into a $10M ARR company. Andrew shares why most acquisitions are far smaller than the billion-dollar headlines, how founders can maximize their odds of success, and the role QSBS played in his own deal structure. They discuss the rise of solo founders, the real impact of AI on early-sta...

In this special episode, originally recorded as a webinar ("Understanding OBBBA’s Section 1202 Revisions"), we dive deep into the tax implications of the "One Big Beautiful Bill Act" (OBBBA) and its sweeping changes to Section 1202 and Qualified Small Business Stock (QSBS). Brian Masterson and Scott Dolson, partners at Frost Brown Todd, are joined by Brady Weller, Director at QSBSrollover.com, to unpack the three most consequential updates to Section 1202: A new tiered holding period struct...

This episode is about bringing value to founders. If you're new to startup valuation, or even if you're not, this conversation with Dan Eyman of Meld Valuation breaks down the key principles every founder should understand. We cover when a valuation is needed, common pitfalls and questions, how to evaluate which firm to go with, and more. Whether you're raising your first round or preparing for an exit, this episode is packed with practical insights to help you approach valuation, fundr...