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QSBS, Solved – Presented by QSBSrollover.com
Your go-to audio source for everything Qualified Small Business Stock (QSBS). Whether you're an investor preparing for a stock sale, a founder nearing an exit, or an advisor exploring QSBS rollover strategies, this podcast delivers actionable insights you won't find anywhere else.
Each episode features audio versions of our most popular articles, expert interviews, and deep dives into QSBS rules, tax planning, eligibility, and the mechanics of rollovers under Section 1202 and 1045.
Hosted by the team at QSBSrollover.com, we break down complex topics to help you solve QSBS – from exemptions to rollovers to real-world structuring.
Contact: Brady@QSBSrollover.com
21 Episodes
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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...
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 rang...
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 pitf...
In this episode of QSBS, Solved, we break down why Qualified Small Business Stock (QSBS) isn’t just for Silicon Valley tech founders. Using the recent Chobani acquisition of Daily Harvest as a real-world case study, we highlight how early shareholders and founders outside of tech—like those in consumer brands, food, beverage, and direct-to-consumer startups—can unlock millions in tax-free gains if they plan smart with QSBS. We walk through what it takes to qualify for QSBS, how non-tech compa...
Not every startup can tap into the huge tax advantages of Qualified Small Business Stock (QSBS), and in this episode, we’re breaking down exactly why. Join us as we unpack Section 1202 of the tax code and spotlight all the types of businesses that don’t qualify for QSBS, including law firms, healthcare providers, consulting companies, finance, hospitality, and more. If you’re building a business or planning a QSBS rollover, knowing these exclusions can save you from making a costly mistake. W...
Brady Weller and Mark Cecchini discuss wealth planning strategies and tax savings opportunities (via QSBS) that founders need to consider when experiencing a liquidity event. Contact: Brady@QSBSrollover.com | www.QSBSrollover.com
Claim QSBS when you sell secondary as part of a funding round. QSBS rollovers can bridge the holding period gap to 5 years for founders selling stock "early". AI company raising a large amount of funding early one? We're in a unique moment that is going to unlock billions in tax savings using QSBS Rollovers. Contact: Brady@QSBSrollover.com | www.QSBSrollover.com Contact: Brady@QSBSrollover.com | www.QSBSrollover.com
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