When founders hear “antitrust,” they often think of massive, headline-making mergers between global corporations. The reality is different. Antitrust laws don’t just apply to billion-dollar deals. They apply to mid-market transactions as well—and increasingly so. …
Most founders think selling a business is about finding the right buyer, negotiating price, and getting to closing. That’s only part of the equation. What often catches founders off guard are the regulatory hurdles that …
When founders think about taxes in an M&A deal, most focus on federal capital gains. That’s understandable. Federal taxes are the headline number. They’re the ones everyone talks about. But in many transactions, the more …
Earnouts are one of the most misunderstood components of an M&A deal. On the surface, they seem straightforward: “If the business performs, you get paid more.” But beneath that simplicity is a layer of complexity …
Most founders treat the Letter of Intent (LOI) as the starting line. In reality, it’s often the point where your flexibility starts to disappear. By the time you’re reviewing an LOI, key elements of the …
Most founders spend years—sometimes decades—building their business. Then they spend a few months negotiating the sale. And far too often, they spend almost no time truly understanding the tax implications of that sale. That’s where …
Selling a business is complex. Selling a business across borders adds another layer entirely. Different jurisdictions. Different tax regimes. Different rules around how income is treated, taxed, and transferred. And while most founders focus on …
If you spend enough time in M&A, you’ll eventually hear about something called a 338(h)(10) election. For many founders, it sounds like technical tax jargon. And at first glance, it is. But beneath that complexity …
One of the biggest surprises founders face after selling their business isn’t the deal itself. It’s the tax bill. You spend years building value, negotiate a strong outcome, close the transaction—and then realize a significant …
If you’re a founder thinking about selling your business, there are very few tax advantages as powerful—or as misunderstood—as QSBS. Qualified Small Business Stock. For those who qualify, QSBS isn’t just a tax benefit. It’s …