Category: News and Insights

How Earnouts and Deferred Payments Can Lead to Surprising Tax Outcomes

Did you really sell your company for $35 million? A buyer agrees to pay $25 million for a business. The seller negotiates an additional $10 million earnout tied to future performance. Everyone leaves the closing table feeling good about the economics. Celebrations and closing dinners commence. Then, months or even years later, the parties discover […]

Considerations and Strategies for Patenting AI

Key Takeaways: Artificial intelligence (AI) generally refers to computer systems that perform tasks ordinarily requiring human-like perception, reasoning, prediction, classification, language understanding, planning, or decision-making.  Modern AI typically involves machine-learning (ML) models trained on data rather than hand-coded rules, including neural networks (such as convolutional and recurrent networks) and transformer-based models like many large language […]

QSBS Planning in 2026: The Small Mistakes That Can Destroy a Massive Tax Benefit

Founders and early-stage investors routinely spend months negotiating valuation, governance rights, liquidation preferences, and dilution protections. Then, years later, when a company finally reaches a successful exit, many discover they overlooked one of the most valuable economic terms in the entire deal: whether the corporation’s stock qualifies for the capital gain exclusion under the “Qualified […]

Founders Cellar: Bringing Together Founders and Investors

Boston, MA — Gesmer Updegrove LLP, a leading law firm serving technology companies and high-growth businesses, recently hosted Founder’s Cellar, a curated, invite-only event designed to bring together founders, investors, and operators for an evening of meaningful connection, candid discussion, and shared experience. Held at the firm’s Boston office, Founder’s Cellar reflects Gesmer Updegrove’s continued […]

Curaleaf Closes a $500 Million Private Placement of Secured Notes

In recent news, our client Curaleaf closes a $500 million private placement of senior secured notes, the largest bond offering completed in the cannabis sector to date. Thank you to the Gesmer Updegrove team of Sarah Richmond, Sean Gilligan, Jeremy Cohen and Leslie Martello, for their leadership throughout this landmark transaction. Curaleaf is a leading […]

AI, MNPI, and the SEC: How Existing Law Applies to Model-Driven Trading

When an AI system is trained on material nonpublic information, MNPI, and then used to inform or execute trades, the firm deploying that system may face insider trading liability, even if no human trader ever directly reviewed the underlying data. The SEC has not yet brought a case on this precise theory, but recent enforcement […]

Prediction Markets, Sportsbooks, and Selig’s CFTC: A Jurisdictional Inflection Point

Prediction markets were once on the margins of financial innovation, but that era is over. Sports-linked event contracts have become the flashpoint for a rapidly escalating conflict between federal commodities regulators, state gaming regimes, and the multibillion-dollar sportsbook industry. The dispute is often characterized as a preemption fight, and in one sense it is. But […]

SEC Chair Outlines Plan to Bring Clarity to Digital Asset Oversight

SEC Chair Paul S. Atkins’ recent remarks on Nov. 12, 2025 at the Federal Reserve Bank of Philadelphia signal one of the most constructive regulatory developments the digital asset industry has seen in years. His “Project Crypto” framework reflects a meaningful shift toward clarity, predictability, and principled application of the federal securities laws. For innovators, […]

What changed in 2025 for Crypto Tax?

KEY U.S. FEDERAL AND GLOBAL DEVELOPMENTS Since 2023, there has been a wave of significant tax and regulatory developments affecting digital assets in the United States and abroad. To help clients stay grounded amid rapid change, we’ve prepared a brief, focused review of several of the most important updates. What follows is a concise summary […]

SEC Chairman Paul Atkins Announces Updates to Wells Process

SEC Chairman Paul S. Atkins has signaled a shift in how the Commission approaches the Wells process, announcing a series of procedural refinements aimed at standardizing and clarifying how the SEC handles pre-enforcement notice and response. In his keynote address at Fordham Law School’s 25th Annual A.A. Sommer, Jr. Lecture on Corporate, Securities, and Financial […]

SEC Policy Update: Coordinated Review of Settlements and Waivers Restored

On September 26, 2025, Chairman Paul S. Atkins of the U.S. Securities and Exchange Commission (SEC) announced that the Commission will restore its prior practice of simultaneous consideration of settlement offers and related waiver requests in enforcement actions. The policy change reverses a 2021 decision under prior leadership that had required waiver requests to be […]

SEC Provides Key Update on Treasury Clearing Rule Implementation

On September 30, 2025, SEC Commissioner Mark T. Uyeda issued an important update on the Commission’s ongoing efforts to implement the Treasury Clearing Rule, a major regulatory initiative aimed at enhancing the resilience and transparency of the U.S. Treasury market. The statement outlined recent progress, identified remaining open questions, and encouraged continued engagement from market […]

Gesmer Updegrove Hosts 2025 Mackrell International Americas Regional Business Meeting

Gesmer Updegrove LLP was proud to host the 2025 Mackrell International Americas Regional Business Meeting in Boston, welcoming member firms from across the Americas for several days of collaboration, knowledge sharing, and strategic discussion. As a long-standing member of Mackrell International, Gesmer Updegrove was honored to bring together leading independent law firms to strengthen cross-border relationships […]

Coordinated Clarity: SEC and CFTC Issue Joint Statement on Spot Crypto Asset Trading

On September 2, 2025, the U.S. Securities and Exchange Commission’s (“SEC”) Division of Trading and Markets and the U.S. Commodity Futures Trading Commission’s (“CFTC”) Divisions of Market Oversight and Clearing and Risk (together, the “Divisions”) issued a joint staff statement (the “Joint Statement”) as part of a new cross-agency initiative titled Project Crypto–Crypto Sprint.1 Project […]