Trevor McCandless

Here’s a hard truth: 65% of businesses fail within a year of a founder’s death. If 85% of your net worth is tied to your company and something happens to you, your family could face a severe financial crisis at the worst possible time. As a CPA working closely with entrepreneurs , I see this scenario far too often. Successful business owners invest everything into their companies, creating impressive growth and revenue—but this level of concentration puts their families at risk. Table of Contents The Founder Trap How to Calculate Your Risk Smart Allocation Strategy A Personal Example Conclusion The Founder Trap Many entrepreneurs have most of their net worth wrapped up in their business. It makes sense—you’re building something, seeing returns, and often outperforming other investments. But this creates a serious vulnerability. What happens if your business struggles, or you become seriously ill and can’t work? Income stops. The business value can drop. And if most of your wealth is in...

As we move into 2026, many liquidity events are on the horizon. Exits, mergers, acquisitions, and private investments are happening. When this occurs, the focus quickly shifts from growth to: how can we minimize the tax impact? That’s why planning matters. Strategic Approaches For some clients, it’s about tax loss harvesting—stacking losses before a major liquidity event. For others, it’s setting things up early so opportunities like QSBS are available later. Once assets are in place, different strategies around lending, interest rates, and capital use come into play, all while avoiding unnecessary taxes. The Bigger Picture This isn’t about a single tactic. It’s about seeing what’s coming and planning early enough to keep more of your gains. When building your financial castle, the foundation starts long before the liquidity event happens. Final Thoughts Liquidity events in 2026 will bring opportunities—but also potential tax exposure if you aren’t prepared. Early planning, whether thr...