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My clients at companies preparing for an initial public offering (IPO) are giddy with thoughts of the wealth and opportunities it will provide. Many of them have worked at these companies since the startup stage, and the IPO represents a long-awaited event that may be life-altering for both their company and them. I try to set them straight with five crucial points that may help to manage their expectations.

Prepare for unexpected twists—not every IPO company's stock price goes up.

1. Expect Volatility

Get ready for a roller-coaster ride! Your net worth may jump up and down by amounts greater than your annual salary as market volatility whips the stock back and forth.

Recent billion-dollar IPOs are examples of the big payoff that many startup companies' employees have dreamed of since they joined their companies amid the volatile markets of the past decade. However, I recommend to my clients that they should prepare for unexpected twists—not every IPO company's stock price goes up. The stock price of many high-profile IPO companies actually fell below the IPO price during the period right after the company went public. Remember what happened with the $16 billion IPO of Facebook? There was what could only be described as hysteria, causing the price to plummet from its initial $38 to as low as $17.73 four months later. The stock took more than a year to recover.

With your IPO company's stock price, you want to hope for the best but plan for the worst—especially considering the price has been bid up by venture capitalists ahead of the IPO. Don't assume further appreciation, and prepare for the possibility of a decline.

2. Respect Diversification

At new publicly traded companies, many of the employees are young. This is very likely to be their first experience with real wealth. Like professional athletes or lottery-winners, these young people have what looks like a substantial net worth, and yet their income and net worth are tied to their companies' value in a competitive world economy where fortunes can come and go quickly. Frequently, people who work for a company that goes public do not know how to handle the windfall of sudden wealth and make poor financial decisions. Because they are passionately loyal to their companies, these investors may resist suggestions to diversify their holdings. Often the corporate culture reinforces this attitude. There is no lack of confidence for the future at a successful startup.

Remember that your income is already tied 100% to the company. To achieve balance in your net worth, plan to sell shares and invest in diverse assets.

Remember that your income is already tied 100% to the company. To achieve balance in your net worth, get ready to sell shares according to a systematic plan and invest in diverse assets. I encourage IPO employees to diversify their wealth holdings by selling some shares when they can and investing those amounts in other assets. Have a systematic approach to moving some net worth into other assets. A sales plan under SEC Rule 10b5-1, managed through an experienced equity compensation financial planner, is the recommended method for this approach. (For details, see my article on diversification.)

3. Get Real About Your Wealth

Be serious about this new-found wealth. It's no longer pie-in-the-sky money. It is real and should be responsibly managed well into the future.

What we often see is that people who are very closely involved with a relatively young company believe their company is the greatest investment in the world. But a naive employee with new wealth is likely to be contacted by many stockbrokers, financial advisors, and wealth advisors—each with their own idea of what the employee should be doing with the money. That doesn't always work out for the inexperienced investor.

For some newly enriched employees in hotbed IPO country, such as the San Francisco area, financial planning and/or diversification may mean moving into an alternative and equally volatile asset class for the first time: real estate. The fact that new wealth will allow you to buy a big house doesn't mean you should do so. If we learned anything from the credit crunch of 2008, it is that home prices don't always go up—and the most expensive homes are the most vulnerable to wide price fluctuations.

4. Live With Restrictions From The Underwriter And The SEC

Be mindful of SEC rules when selling your company's shares. The consequences that await violators may include fines several times greater than their stock proceeds.

The restrictions of the lockup will keep you from doing anything with your shares for (usually) 180 days after the IPO date, even if you have exercised options or hold restricted stock that vested before then. Executives must follow additional restrictions and rules even after the lockup period (see a related FAQ). Don't make the mistake of judging stock values according to the price on the day of the IPO. The price at liquidity, when shares are no longer locked up, may be very different. I recommend waiting to exercise any stock options until after the lockup.

Whatever you do, your individual circumstances, including the rules of the company you work for, dictate your strategy. Be careful. Newly public companies may not have fully developed insider-trading policies. They may not have procedures in place to help prevent inadvertent violations of SEC rules. Even in the absence of these in-house rules, each stockholder is responsible for following the law. The potential consequences that await violators include fines several times greater than the proceeds of the transaction that led to the violation.

5. Understand Taxes

Taxes are a potential minefield for the newly wealthy. If part of your equity compensation package includes incentive stock options (ISOs), in addition to founder's shares, nonqualified options (NQSOs), or any of the myriad of other forms of stock-based pay discussed on this website, tread lightly before you begin to exercise or sell. Make sure your advisor has experience in managing multiple forms of stock compensation simultaneously and in qualified small-business stock so that you get the chance to deploy a sound tactical disposition plan.

Alert: Exercising stock options during a lockup does not delay the related taxes until the lockup is over. With NQSOs, the taxes are due at the time of exercise, even though you cannot yet sell shares to pay them.
Remember that the lockup does not delay any taxes triggered by stock compensation during the lockup period.

Taxes create an even greater dilemma while your company is private and resale opportunities are limited or nonexistent (see related article). I am not a big fan of exercising options before your company goes public, given the risk that it may never go public or be acquired.


You want to consider the tax consequences of exercising ISOs before the IPO and holding the shares to get all capital gains on the eventual sale. If the price of your stock crashes but you have already triggered the alternative minimum tax on your paper gains, you can find yourself selling low-priced shares that may not even cover the tax bill you incurred at exercise. This risk is even greater with NQSOs, as you will also trigger tax at exercise on the spread.

Estate Planning

You also want to involve an experienced estate-planning lawyer. There are several strategies to consider with trusts, and with gifting or donating stock. These can be put in place when your stock price is low, long before the IPO.

Editor's Note: In addition to the related articles shown below, see an article elsewhere on this website with insights on pre- and post-IPO planning from financial advisors in different regions of the United States. See also an article from the San Francisco Chronicle on preparing for an IPO: What To Know If Your Company Is Headed For An IPO. It features additional guidance from a few employees who have gone through IPOs and some advice from financial experts, including those at myStockOptions.com.

John P. Barringer is the Managing Partner of Executive Wealth Planning Partners in Denver, Colorado. His long career in the securities industry has allowed him to discover numerous secrets for successfully building wealth. Learn more at www.executivewealthplanning.com. This article was published solely for its content and quality. Neither the author nor his firm compensated us in exchange for its publication.