If you’re an employee at a startup, you may be offered stock options as part of your compensation package. These stock options can be a valuable source of income, but only if you understand how they work and when to exercise them.

One strategy for maximizing the potential profits from your stock options is to exercise them early. This involves exercising your options before the company goes public, typically via filing a form 83(b).

What is an early exercise ISO 83B?

An early exercise 83(b) is a provision that allows an employee who receives stock options as part of their compensation package to exercise those options before they are fully vested, and to pay taxes on the difference between the fair market value of the stock at the time of exercise and the exercise price, which is typically lower. By filing an 83(b) election with the Internal Revenue Service (IRS), the employee can have their tax liability determined on the date of exercise rather than the date the shares vest and are exercised. This can be advantageous because it allows the employee to potentially lock in a lower tax liability, especially if the value of the stock increases significantly over time. However, there are some risks associated with early exercise, and it’s important to consult with a financial advisor or tax professional before making any decisions.

By exercising your stock options early, you can potentially lock in a lower exercise price for your company shares, which can result in a lower bargain element. This can be advantageous because it can help you avoid or at least lessen your alternative minimum tax bill (AMT liability), which you may have to pay if you wait until the company goes public and the stock price increases significantly.

What is the ISO 100K rule early exercise?

The $100K ISO limit or the $100K rule is a provision in the tax code that limits the amount of incentive stock options (ISOs) an employee can exercise and treat as ISOs in any given year. Under this rule, an employee cannot treat more than $100,000 worth of exercisable options as ISOs in a single calendar year.

If an employee exercises ISOs that exceed the $100K limit, any excess options will be treated as non-qualified stock options (NSOs) instead. This means that the employee will not be able to take advantage of the potentially favorable tax treatment of ISOs, and instead will be subject to ordinary income tax rates and potentially higher tax liability.

The $100K ISO limit applies only to ISOs, not to non-qualified stock options (NSOs). It is important for employees who receive ISOs to be aware of this limit and plan their exercise strategy accordingly to avoid potential tax consequences.

Why early exercise option contracts?

Waiting to exercise can result in a higher AMT liability compared to if you had waited to exercise your options until after the company goes public and the stock price increases because it’s expected the price will increase (especially after IPO). Still, keep in mind, exercising early, has its own risks as well and doesn’t make sense for everyone, always. Startups go under more often than they take off and become Facebook.

One way to potentially avoid an AMT liability is to make an 83(b) election. This election allows you to pay taxes on the fair market value of the stock at the time of exercise, rather than paying taxes on the difference between the exercise price and the fair market value when the stock vests. By doing this, you may be able to reduce or eliminate the bargain element, which can lower your AMT liability.

However, it’s important to note that making an 83(b) election is not always the best choice for everyone, as it can have potential drawbacks such as a higher regular tax liability and the risk of losing money if the stock price drops. It’s important to consult with a financial or tax advisor to help you make an informed decision about when to exercise your stock options and whether to make an 83(b) election.

In addition to the potential tax benefits, exercising your stock options early can also help you take advantage of a favorable vesting schedule. For example, if you exercise your options early, you may be able to start the clock on your holding period requirements for long-term capital gains treatment. This can mean potentially 20-30% tax savings over short-term capital gains rates (if not more) depending on your financial situation.

How do you calculate your AMT liability when you exercise your stock options?

If you exercise stock options early, you may be subject to the alternative minimum tax (AMT). When you exercise incentive stock options (ISOs), the difference between the exercise price and the fair market value of the stock on the exercise date is called the “bargain element”. This bargain element is considered a tax preference item for AMT purposes, which means it’s added back to your regular taxable income to determine your AMT income.

To calculate your AMT liability when you exercise ISOs early, you’ll need to determine the amount of the bargain element and add it to your regular taxable income. Once you’ve added it to your taxable income for AMT purposes, it’s important to evaluate current AMT threshholds and verify if your combined income + AMT Preference Items (Bargain element included) put you above the threshold and therefore, require you to pay AMT.

Risks The Option Holder Should Remember

There are risks associated with the early exercise of stock options, particularly if the stock price doesn’t increase as much as you had hoped. Additionally, if you make an 83(b) election, you could lose unvested shares if you leave the company before your vesting schedule is complete. Here are a few other risks you may not be aware of:

1. Tax consequences: When you exercise ISOs, you may be subject to alternative minimum tax (AMT). If the stock price decreases after you exercise, you could be left with a tax bill that exceeds your gains and, because your stock is privately traded, you’ll have to pay this bill out of pocket.
2. Cash flow: Exercising ISOs requires cash, either to purchase the shares or to pay the AMT. If you don’t have the cash available, you may need to sell some of the shares immediately after exercising to cover the costs, which could limit your potential gains (assuming there’s a tender offer).
3. Risk of investment: Exercising ISOs means investing a significant amount of your money in a single stock. This can be risky, as the stock price can fluctuate significantly in the short term, and there is always a risk that the company could go bankrupt.
4. Opportunity cost: many startups have passionate employees but their corporate board may lack experience in leadership or not have all the skills necessary to grow the company as fast as their larger, public competitors. If your investment only grows at 5% per year and you could have gotten 10% or higher, you may regret this decision.

In summary, the early exercise of stock options can be a valuable strategy for maximizing the potential profits from your stock options. By exercising your options early, you can potentially lock in a lower exercise price and avoid AMT. However, it’s important to carefully consider the risks and potential tax implications, and seek the advice of a professional before making any decisions about early exercise or making an 83(b) election.