Key Takeaway Overview In many private M&A transactions, buyers and sellers usually reach an impasse on valuation. Buyers may be unwilling to pay the seller’s full asking price at closing, particularly where future growth projections are uncertain. These days, two common tools used to bridge that gap are seller notes and earn-outs. While both defer […]
A Brief Guide for Compliance OVERVIEW: The Cyber Resilience Act makes cybersecurity a mandatory, enforceable product requirement for software and connected hardware sold in the EU by manufacturers anywhere, including those in the US who sell or distribute into the EU. Vulnerability and incident reporting obligations begin September 11, 2026; full compliance is required by […]
Key Takeaways Five Questions Every Growth Company Should Still Be Asking Regarding Research Expenditures When Congress enacted the One Big Beautiful Bill Act in July of last year, many technology companies breathed a collective sigh of relief. The legislation largely reversed one of the most unpopular business tax changes in recent memory by restoring the […]
Boston, MA — Gesmer Updegrove LLP, a Boston-based law firm concentrating in technology companies and emerging growth businesses, has been recognized in both the Chambers USA 2026 Guide and the Legal 500 USA 2026 Guide, two of the most respected independent legal ranking publications in the world. Inclusion in Chambers USA places Gesmer among fewer […]
Key Takeaways Overview For professionals involved in lower and middle market mergers and acquisitions, there is a common misconception that deals fail because of legal issues. In my experience, that is rarely the case. Most transactions encounter difficulty because of misaligned expectations, delayed decision-making, inadequate communication, or the failure to identify and address issues early […]
Key Takeaways Overview Every startup uses AI tools. Many founders, and their employees and contractors, have not read the terms those tools come with. That is not a criticism as those agreements are long, dense, and easy to click through. But the legal risk embedded in them is real, and it does not announce itself […]
Key Takeaways Overview SAFEs are popular with startup founders for good reason. They are short, relatively simple, and can often be completed much faster than a priced equity financing. That simplicity is also part of the problem. Because SAFEs are so easy to use, founders sometimes raise one SAFE round, then another, then another, without […]
Key Takeaways 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 […]
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 […]
Key Takeaways What Is QSBS, and Why Does It Matter So Much Right Now? 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 […]
The CFTC’s latest enforcement action against a Google employee for alleged insider trading on Polymarket marks another significant step in the Commission’s effort to apply traditional market abuse principles to prediction markets and event contracts.
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 […]
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 […]
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 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 […]