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Roger Royse is a partner in the Palo Alto office of Haynes and Boone, LLP and practices in the areas of corporate and securities law, domestic and international tax, mergers and acquisitions, and fund formation. He works with companies ranging from newly formed tech startups to publicly traded multinationals in a variety of industries. https://www.haynesboone.com/people/r/...  https://rogerroyse.com/

0:00–1:48 The question I'm getting on every formation call
1:48–4:10 How Delaware became the default
4:10–6:27 A rulebook vs. a body of case law
6:27–9:42 The founder's view
9:42–12:18 The investor's view
12:18–14:35  The decision framework by stage
14:35–17:10  Traps
17:10–18:18 Takeaways

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Founder of BADASS Labs and Tomorrow Biotech, helping founders navigate the journey from concept to commercialization in both biotech and climate innovation, including human and planetary health: revolutionary therapeutics, clean energy, biological remediation, enhanced agriculture, and sustainable manufacturing.

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Welcome back to the 10,000 Startups Podcast. I’m Roger Royse, and today we’re talking about worker misclassification — the Google Maps drivers case — and the very real lessons for anyone building a company.

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In this episode of his podcast, Roger Royse discusses the tax-planning strategy known as "QSBS Stacking" and warns that the IRS is increasingly viewing it as an abusive practice (0:02-0:16, 2:47-2:54).

What is QSBS Stacking?

Qualified Small Business Stock (QSBS) allows holders to exclude up to $15 million of capital gains (for stock acquired after July 2025) upon sale, provided specific holding period requirements are met (0:26-0:41, 2:08-2:13).

• The Strategy: Under IRC Section 1202(h), when QSBS is transferred via gift, the recipient "tacks on" the original holder's holding period and tax basis (0:55-1:13).
• Multiplying the Benefit: By gifting stock to multiple individuals (such as children) or non-grantor trusts, taxpayers create new, separate taxpayers. Each of these recipients is then entitled to their own separate $15 million exemption, effectively "stacking" the total tax exclusion (1:13-2:01).

Potential Regulatory Changes

While Congress expanded QSBS benefits recently, it did not take action to curb stacking (2:34-2:46). However, Roger Royse reports that a high-ranking Treasury official recently signaled that the government considers stacking an abusive "Silicon Valley tax shelter" and intends to address it through future regulations (2:21-2:34, 2:47-3:00).

Founders and investors are advised to stay tuned, as new guidance could significantly impact the viability of this strategy (2:56-3:04).

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Kim Le, Founder of A2Q2, helps tech leaders scale sales and finance systems with clarity and confidence. This episode discusses accounting and books for startups including best practices, common mistakes and war stories.

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SB 21 amended Delaware General Corporation Law (DGCL) § 144 (conflicted transactions) and § 220 (books and records) to restore predictability and reduce litigation risk in transactions involving interested directors, officers, and controlling stockholders. A recent DE Supreme Court case ruled on the constitutionality of the law.