David J Prothero, CPA, PC

10/23/2026

If you make a mistake on your tax return, it may be noticed by the IRS. Here are some of the most common causes.

October 15th marks the end of the 2025 tax filing season. Now the formal audit period for 2025 tax returns is underway. Here are some tips to be prepared.

10/22/2026

Morgan Stanley strategists think the unwinding in high-flying stocks could be good for the S&P 500 overall, saying “8000 is very achievable.”

10/19/2026

'Financial Freedom' author Grant Sabatier says FIRE is easier to achieve in 2026 than ever before. He says the internet has made it easier to build income streams. Plus, FIRE has become easier to personalize. Still, inflation and housing costs have made FIRE harder for lower earners.

10/16/2026

Sports betting comes with IRS strings. Know them and plan accordingly.

As sports betting grows in popularity, the IRS is paying attention. Do you know how your winnings and losses are taxed?

10/16/2026

What are Incentive Stock Options (ISOs), and how do they work?

If you are a tech employee or startup leader, understanding ISOs can mean the difference between a massive tax bill and generational wealth.

Unlike Non-Qualified Stock Options (NSOs), ISOs offer a massive tax benefit: you don't pay ordinary income tax upon exercise. Instead, you pay taxes (often at a lower rate) when you sell the underlying shares.

However, navigating ISOs requires a precise strategy. Here is a 3-step checklist to optimize your ISOs:

👍 Watch the AMT Trap: When you exercise ISOs and hold the stock, the spread (the difference between fair market value and your grant price) counts as income for the Alternative Minimum Tax (AMT). This can trigger tax.

👍 Hit the Holding Period: To qualify for favorable tax treatment, you must hold your shares for at least 2 years from the grant date AND 1 year from the exercise date.

👍 Model Your Cash Flow: Consider the cost to exercise, potential AMT tax, expected holding period, stock concentration, and liquidity before exercising

❓ Have you modeled your ISO exit strategy yet? What's your biggest roadblock with startup equity? Lets discuss in the comments.

10/15/2026

Stop pricing trusts like products—estate planning is a strategic design process where goals, complexity, and protection drive value far more than upfront cost.

10/12/2026

A holographic will is a handwritten will signed by the person making it that needs no witnesses.

10/08/2026

The life expectancy method calculates IRA payments by dividing the account balance by the policyholder’s anticipated length of life. Required Minimum Distributions (RMDs) must be withdrawn from certain retirement accounts starting at age 73.

10/07/2026

Now is the time to visit your tax obligation. Here are some areas worth your attention.

Fall is now upon us meaning there are only three months left to consider making smart moves to manage your tax obligation. With this in mind, why not review the tips included here to see if there is an area or two worthy of your attention. Plus consider a deeper dive into the long held idea of creat...

10/05/2026

Tax-planning strategies for California's ultra wealthy include buying dream vacation homes and increasing philanthropy.