Wealthrive Weekly: The 100-Day Tax Window
Smart Business Owners Open After September 15 For many entrepreneurs, September 15 feels like the finish line for the third quarter. The estimated payment goes out. The calendar reminder clears. Everyone exhales and goes back to closing deals, hiring, and running the business. That instinct is understandable. It is also expensive. Because once the September […]
Wealthrive Weekly: The September 15 Tax Checkpoint Smart Business Owners Shouldn’t Treat Like a Bill Due Date
For many entrepreneurs, September 15 feels like another bill due date.A calendar reminder. A payment amount. A scramble to get it done. Then everyone exhales and goes back to building the business.That instinct is understandable. It is also expensive.Because September 15 is not just when the third estimated-tax installment is due. It is one of […]
How Much of Your Business Should You Sell? A Framework for Affluent Founders
A private equity firm wants 70%. A minority investor wants 30%. Your banker says rolling more equity could create a larger second exit. But how much of your business should you actually sell? For affluent founders considering a partial sale, minority investment, or private equity recapitalization, that question is more important than the headline valuation. […]
Cash Balance Plans for Business Owners: A 2026 Decision Guide
A highly profitable business can create an unusual retirement-planning problem. The owner earns more than a traditional retirement plan can readily absorb, pays substantial current income taxes, and may still have most of their net worth tied to the company. That combination often leads to a familiar question: Should I add a cash balance plan […]
Before You Transfer Founder Stock: What Affluent Owners Should Review Before a Partial Sale or Recap
A partial sale can look simple from the outside. You sell part of the company. You take chips off the table. You keep a meaningful stake. You stay involved for the next chapter. But for affluent founders, the months before a partial sale or recapitalization can be one of the most important planning windows of […]