QSBS, Solved

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 link to Alex’s Seed to Sequoia newsletter below these episode notes.

Alex also shares lessons from his own founder journey, including what makes or breaks a deal, the dangers of focusing too much on tax optimization at the wrong stage, and how AI is reshaping both outbound sales and acquisition strategy. 

Newsletter: https://seedtosequoia.silverwood.ai/subscribe

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 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.

The conversation covers common pitfalls that put eligibility at risk, from structuring mistakes and equity issuance problems to challenges around data collection at exit. Jonathan outlines how Cap Gains works with venture funds and their partners to anticipate tripwires, prepare documentation, and identify opportunities such as rollovers and exit planning strategies.

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 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 than a guarantee.
• OBBBA changes — how raising the exclusion and gross asset caps reshapes opportunities for founders, early employees, and venture funds.
• The SAFE debate — whether Simple Agreements for Future Equity should trigger QSBS holding periods, and the practical implications for early-stage investors.

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 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 Stock (QSBS) exemption. The conversation covers how founders and investors can unlock millions in tax savings through Section 1202 exclusions and Section 1045 (QSBS rollovers), plus recent legislative updates that make QSBS even more attractive.

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.

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 liquidity.

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 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-stage businesses, and what sellers can do to prepare for a smooth, high-value exit.

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 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 structure (3-, 4-, and 5-year exclusions)
• An increase in the QSBS exclusion cap from $10 million to $15 million (plus inflation indexing)
• A raise in the aggregate gross asset limit from $50 million to $75 million

The discussion addresses how these changes will impact tax planning for founders, investors, and advisors—especially in light of effective dates, rollover strategies under Section 1045, and the increased importance of entity structuring. The panel also discusses potential IRS scrutiny around restructuring tactics and outlines emerging opportunities stemming from these new rules.

Whether you're a startup founder, investor, or tax advisor, this episode offers practical takeaways and expert insight into the future of QSBS planning under the new regime.

Special thanks to the team at Frost Brown Todd for inviting us to collaborate and for allowing us to use the audio from the session on our podcast feed.

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 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, fundraising, and financial compliance with clarity and confidence.

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 a repost of an interview featuring Brady Weller, Director of QSBSrollover.com, conducted by Earnest Sweat of Swimming with Allocators. SWA is a podcast delving into the strategies and perspectives of leading allocators in the VC space. Designed for fund managers and fellow allocators, the show offers a deep dive into the methodologies and approaches adopted by prominent players in the industry. The conversations are rich, and enlightening, and cover a wide range of topics relevant to the venture asset class from an LP's viewpoint.

Earnest Sweat is the Founding Partner of Public School Ventures, a dynamic syndicate of over 600 technical operators, go-to-market specialists, and LPs. Previously, Earnest built new venture capital practices at Prologis and GreatPoint Ventures. His focus is on investing in value chaintech, specifically vertical SaaS, applied AI, middleware, and B2B marketplaces, which are poised to revolutionize foundational industries like real estate, insurance and supply chain. Earnest has sourced and led investments in companies such as Flexport, Flexe, KlearNow, and Lula Insurance.

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.

On today’s episode of QSBS Solved, we break down the essential facts about Qualified Small Business Stock—QSBS—and why it’s such a powerful tax-saving tool for startup founders, investors, and early employees. From the requirements for a company to issue QSBS, to the types of businesses that are excluded, we cover everything you need to know about eligibility, the $50 million asset test, the five-year holding period, and how much gain you can actually exclude. We also highlight potential pitfalls, like stock redemptions, and explain how a QSBS rollover (under Section 1045) can help you keep your tax advantage, even if you exit early.

If you want to learn how founders and shareholders in places like New York can potentially eliminate their capital gains tax bill—sometimes as high as 37%—this episode is for you. Whether you’re just hearing about QSBS for the first time or looking to refine your exit strategy, we’ll make sure you’re ready to protect your gains and maximize your upside.

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.