Entrepreneurship

If you’re planning to sell your business someday, here’s a statistic worth sitting with: research from the Exit Planning Institute and PwC found that 75% of business owners feel “unhappy” or “profoundly unhappy” one year after exiting their company. Three out of four owners who worked hard to build something, then sold it or handed it off end up regretting how it turned out. That’s not a small problem. And it’s been true for over a ...

If someone asked you right now what your business is worth, you’d probably answer fast, and with total confidence. That number’s likely made its way into conversations with your banker, onto a personal financial statement, maybe even into a retirement plan your financial advisor put together. Here’s the uncomfortable part: there’s a good chance that number is off by 50% or more. That’s not a knock on you. It’s just that most owners have never had access ...

If you’re selling a privately held business, disclosure is rarely just a matter of completing a checklist. It’s more like managing a series of “layers” that unfold over time. The timing, depth, and framing of what you share can affect how buyers value your company, how much leverage you retain at the negotiating table, and often overlooked how stable your business remains while the transaction is moving forward. A practical way to think about disclosure ...

You’ve probably said it yourself: “Talk to me in five years.” It’s the most common response advisors hear — and it makes sense. You’re heads-down building, not winding down. Exit planning feels like a conversation for later. The business is performing. You have time. And honestly, it’s a lot to think about. But here’s the uncomfortable truth: later is exactly when most exits go wrong. You’re already doing exit planning — just not deliberately Think about the early-stage tech ...

When you bring in an outside advisor — whether it’s an accountant, attorney, consultant, or broker — you’re doing the right thing. You’re acknowledging there’s something you don’t know and going to find someone who does. That’s smart ownership. But there’s a trap hidden in that process that most business owners never see coming. Every Expert Has a Favorite Tool There’s an old saying: to a hammer, everything is a nail. Think about it this way. You go to ...

As a business owner, you belong to a unique group that makes up only 3% of the population. Yet, many advisors treat you like any other client—using the same approaches they apply to executives, professionals, or retirees. This is a fundamental misunderstanding that can impact your business and personal goals. Why You’re More Than Just an Asset You are not simply a high-income individual with concentrated wealth. Your business is not just an investment; it’s an integral ...

Here is how exit planning helped a business owner out of the Neutral Zone. This manufacturer reached out to an exit planning consultant after receiving a book on planning as a gift from a local professional. He was in no particular hurry to leave his business. In the preceding twenty years of ownership, he had grown it from a local vendor to home builders into a nationally known specialty house. The company provided him with a good ...

In our last article, we discussed Non-Qualified Deferred Compensation (NQDC) plans as a tool to compensate key employees for achieving long-term goals. One component of such plans is the fact that they are frequently unfunded and legally considered an unsecured promise to pay. Nonetheless, both plan sponsors and recipients often want a funding mechanism to set aside assets, manage cash flow, or hedge the liability. In addition, employers typically want conditions under which they can rescind ...

Non-Qualified Deferred Compensation (NQDC) plans are a powerful tool for incentivizing and retaining key employees. They offer virtually unlimited flexibility in methodologies, objectives and rewards to suit a company’s strategies and goals. What is “unqualified?” Quite simply, NQDCs are discriminatory. Some owners shy away from that term, but discrimination isn’t automatically illegal. Illegal discrimination in the workplace is when an employer or manager treats an employee unfairly due to their race, color, religion, sex, national origin, age (40 ...

It’s hard to have a business conversation today without someone invoking “the Big Picture.” The 24-hour news cycle runs on urgency, outrage, and uncertainty—and it needs a constant supply to keep attention locked in. The result? Everything sounds like a crisis. Wars. Tariffs. Sanctions. Inflation. Interest rates. Cyberattacks. Political standoffs. Supply chain disruptions. If you own a business, you’ve probably asked yourself at least a few of these questions recently: Will my raw material costs spike again? Should I ...