Wealthrive Weekly: The Year-End Giving Deadline Smart Business Owners Shouldn’t Treat Like a Holiday Habit
Every fall, the asks start arriving. Galas. Year-end appeals. The school capital campaign. The board seat that quietly comes with an expectation. And for a lot of successful business owners, the response is the same every year: write the checks in December, collect the receipts, and let the return sort it out in April. That […]
Wealthrive Weekly: The Q4 Tax Window Smart Business Owners Open Before December 31 Closes
By late September, the calendar has already done a lot of talking. September 15 pushed estimated-tax math and many entity extensions into the open. October 15 forces extended personal and calendar-year C-corp returns across the finish line. Then the room goes quiet—until December panic shows up with delivery delays, payroll cutoffs, and half-finished “we should […]
Wealthrive Weekly: The October 15 Extension Deadline Smart Business Owners Shouldn’t Treat Like a Paperwork Finish Line
For many entrepreneurs still on extension, October 15 feels like the last chore of last year’s taxes. Send the return. Clear the reminder. Stop thinking about 2025. That instinct is understandable. It is also incomplete. Because October 15, 2026 is not just a filing date for extended Form 1040 and calendar-year Form 1120 returns. It […]
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 […]
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 […]