Tag: business

How an S Corporation Election May Affect Financing and Exit

Five Restrictions Founders Should Understand First For unseasoned founders, making an S corporation election for their new company can sound almost too good to pass up. The business generally avoids entity-level federal income tax, and distributions to a shareholder-employee may avoid burdensome employment taxes that apply to wages. So why are so many venture-backed startups […]

Delaware Earnout Decisions and Lessons for Founders and M&A Professionals

An earnout can help a founder and a buyer bridge a valuation gap by making part of the purchase price contingent on future performance. But agreement on the financial target leaves a harder question unresolved: how will the business be run while that target is being measured? Two recent Delaware Court of Chancery decisions illustrate […]

Christopher Ward

Interview with Joseph Keech, CFO of Christopher Ward Tell Us About Your Journey So me personally, background in law and finance, and as I stepped out of practice in finance, in particular, into luxury goods, into luxury events, into cosmetics, luxury car shows, and then now luxury watches. This one’s more interesting— luxury watches at […]

Why Software Company M&A Deals Are Different: Understanding the Purchase Price Traps Hidden in SaaS Transactions

Overview Software companies are often valued differently than traditional businesses. Buyers focus heavily on recurring revenue, customer retention, and predictable cash flow. As a result, software businesses frequently command valuation multiples that exceed those of companies in more traditional industries. But while founders often spend significant time negotiating valuation, many overlook an equally important issue: […]

Avoiding Self-Inflicted Bars to Patentability

Key Takeaways A Governance Checklist for General Counsel and In-House Patent Counsel Most companies think of patent risk as something that comes from the outside. A competitor files first. An examiner finds an obscure reference. A third party publishes something similar. But some of the most damaging losses of patent rights are entirely self-inflicted. They […]

The Practical Realities of Closing a Lower to Middle Market M&A Transaction

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 […]

Legal Risks Your AI Tools May Create

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 […]

The Hidden Dilution Trap for Founders in Post-Money SAFEs

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 […]

How Earnouts and Deferred Payments Can Lead to Surprising Tax Outcomes

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 […]

StairAssist Walker

Interview with Dr. Josh Sigsworth, PT, DPT, Founder & CEO of StairAssist Walker Tell Us About Your Journey 2009 at Baylor University Medical Center when I was a student. I was a young doctor, a physical therapy student, very excited to treat all these different patients on an orthopedic floor, lots of leg fractures, hip […]

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

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 […]

NetSpeek

Interview with Erik Degiorgi, Founder and CEO of NetSpeek Tell Us About Your Journey Yeah, it’s definitely a bit circuitous. I’ve worn quite a few hats in my adult life, but I’ve always been really interested and building things. So I spent some time early on as a young man in the military, and then I got out, and […]

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 […]