David J Prothero, CPA, PC

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 Required Minimum Distributions (RMDs) must be withdrawn from certain retirement accounts starting at age 73.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.

10/02/2026

Here are key happenings and announcements from the IRS that you should understand.

Here are recent changes as announced by the IRS that will impact most of us.

10/01/2026

Watch out for indigestion.

09/28/2026

Sandwich generation caregivers, which is defined as those who support their children and elderly parents at the same time, often describe a state of chronic fatigue as they juggle the demands of family responsibilities.