As we enjoy the Silicon Slopes Tech Summit 2020, it has been great to catch up with executives, investors, and entrepreneurs working to build the next technology ideas into successful companies.  It is interesting to think that we don’t quantify the economic benefits that one great company, which brings together a talented team of founders and executives, finds a successful exit, and then comes back together to do it again at another company, has on an area.  There are many legendary technology companies that have had this effect, creating places like Silicon Valley and other areas in the country known for incubating technology companies and ideas.

One great thing about knowing and working with the seasoned investors and entrepreneurs is their ability to help the new generation see how to solve problems that these companies encounter, and how to avoid the mistakes that some people have made.  In my small part of this world, the conversations in 2001-2002 with employees and executives who were too optimistic in the first internet bubble will never be forgotten.  Yes, you can exercise equity awards like an incentive stock option (ISO) with a promissory note, second mortgage, or personal bank loan, and if the stock price goes up from there and the company achieves liquidity in an IPO or acquisition, you could win big with large gains all taxed at the long-term capital gains rate.  I know a number of people who had this great outcome.  However, the other side is that if the price does not go up, or if the company does not achieve liquidity, then there can be tax problems.  Exercising an ISO will result in an alternative minimum tax (AMT) adjustment in the year of exercise for the spread on the date of exercise.  If an optionee is subject to the AMT, then this tax is due to the IRS based on the value at the date of exercise.  There is no consideration for the fact that the shares are not liquid and have not been sold at the time of or at the value of the corresponding tax obligation, meaning the optionee is gambling that the value the shares will continue to go up and that there will be liquidity.

Those conversations in 2001 and 2002 often involved painful conclusions that the tax was due, and the shares purchased were not worth the exercise price and the taxes, or in some cases, were worth nothing at all.  If a company loan is forgiven there will be additional cancellation of debt income which is subject to tax.  In the end, it is always more comfortable to plan for paying the taxes and ensure that you have the funds to pay them.  If the funds are not there, wait to exercise until liquidity is assured, pay ordinary rates, and sleep well at night.