Working for a startup or a smaller private company can be exciting. You may be creating cutting-edge technology or providing services or products that will fill a need within an industry. It also means you may have the opportunity to become a significant stakeholder in your company before a single share of stock has been sold to the public. If you’ve been granted options in a private company, you may be asking yourself, “Is the potential reward of exercising my options worth the risk?”
This answer is a complicated, nuanced one that will depend on each individual and the company’s circumstances. That being said, I’ve done my best to distill some of the most important lessons learned in helping clients navigate whether to exercise options in their company while it is still private.
Never invest more than you’re willing to lose.
Your company is doing great things and you strongly believe that you’re moving in the right direction. You wouldn’t have chosen to take the risk of working for this company if you didn’t believe so. The inconvenient truth is that so many bright, promising startups or private companies fail each year. A lot of this has nothing to do with the company itself but is simply the result of factors outside its control—like the general market conditions at the time the company was anticipating raising another round of funding.
Before your company goes public or has a liquidity event, there isn’t a readily available market for you to sell any of the shares you received when you exercised. Until your company has actually gone public, there is a reasonable risk the shares you hold from exercising could be worth nothing. Companies are also taking longer and longer to reach a point at which they are ready to go public or IPO. You must go in with an expectation that you could be waiting 10 or more years for the opportunity to sell your shares in the open market. If the possibility of losing 100% of your investment makes your palms sweat, you likely will want to wait until your company is actually public before you exercise your options.
Do take on an amount of risk appropriate for your situation.
It is important to understand the risks and the worst-case scenario of exercising options in a company that is not yet public. On the flip side, exercising options in a private company can have tremendous outcomes for those who were able to buy in at an earlier stage. Before deciding how much to exercise in your company while it is still private, first take a look at your list of financial goals and priorities:
- Do you have a sufficient emergency fund of at least three to six months of expenses set aside in cash in a savings or checking account?
- Are you maximizing savings into the retirement accounts available to you? Have you evaluated whether you’re on track to meet your target retirement date with your current rate of contributions?
- Are you saving enough for other major goals like your kids’ future college expenses?
If you can say yes to all these questions and are willing to accept the risk, then by all means, allocate a certain portion of your income or savings toward exercising options in your company. It is almost always much less expensive to exercise options while your company is still private than after it has gone public. This is because the valuation (409a) while the company is private is usually much lower than the price at which the company will be valued once it is public. A significant increase in valuation will mean a much larger tax bill per option that is exercised.
Understand the tax consequences.
Options are complicated. The type of options you receive will dictate your exercise strategy and the resulting tax implications. You cannot simply look at the cost to exercise as your total cost to purchase shares in your company. It is important to be aware of your company’s most recent 409a valuation, which will determine the amount of income you are recognizing each time you exercise an option. You will be paying tax on income for shares you still cannot sell and may not have an open market for anytime soon. Exercising stock options without fully understanding the tax impact could mean receiving a surprise tax bill and not having enough cash set aside to cover it.
If you exercise Non-Qualified Stock Options (NSOs), your company will withhold 22% of the income recognized for federal taxes. This may or may not be enough to cover your total tax liability for the exercising depending on the amount and makeup of your other income. You’ll want to estimate the additional taxes you may owe due to the exercise of NSOs and make estimated tax payments or set aside enough funds to cover the tax liability when you file.
If you exercise Incentive Stock Options (ISOs), your company will not withhold any amount for federal taxes, and you will be expected to cover the entire tax liability through estimated tax payments. Incentive Stock Options can also create what is called Alternative Minimum Tax (AMT), which is complicated to calculate and track on an ongoing basis.
Ask for help.
There are certain projects in my home I’m willing to tackle and certain projects I’m more than happy to hand off to professionals. Paint the guest room? No problem. Rewire and update the electrical in my kitchen? You better believe I’m leaving that entirely up to the capable hands of a licensed electrician.
When we talk about options, and especially options in a private company, we are entering a territory where the DIY approach can fail you miserably. Employ the help of a finance or tax professional who has expertise and experience navigating private company stock option strategy. You don’t want to be in the position of wondering why you have tax bills that are much higher than what you were expecting or realize that failing to file a form by a certain deadline is going to cost you thousands of dollars in the future. A qualified professional can help you determine the appropriate amount of risk to take, given your current financial situation and goals, while providing peace of mind that there are no major tax surprises on the horizon.
Is your company the next Apple? I have no idea. What I do know is that the future rarely plays out exactly how you expect it will, for better or for worse. All we can do is make our best calculated bet with the information and resources we have at the time. After that, all that’s left to do is embrace the adventure.
Disclosure: The material is presented solely for information purposes only are not intended to provide specific advice or recommendations for any individual. The information presented here has been gathered from sources believed to be reliable; however, Merriman cannot guarantee the accuracy or completeness of such information, and certain information presented here may have been condensed or summarized from its original source. Merriman does not provide tax, legal, or accounting advice, and nothing contained in these materials should be relied upon as such.
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Paige worked in the tech industry for several years and is passionate about helping tech employees and other mid-career professionals bridge the gap between their intentions and actions. Paige recognizes that money is incredibly personal and strives to create an open and non-judgmental space where you can invest with your values and make progress towards your goals.
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