For advisors, a little tax knowledge can be a dangerous thing. “Most people lose more money trying to reduce taxes than they save in taxes,” says advisor Less Antman, who founded the firm SimplyRich and taught prep courses for CPAs for 27 years.
In an interview with ThinkAdvisor, he warned of the dangers of too much portfolio rebalancing, the limitations of tax-loss harvesting, and the unintended consequences now dogging investors who tried to dodge estate taxes in the ’90s.
Yet, the lure of tax minimization is powerful and often destructive, for middle-class investors through the wealthiest.
Paper Millionaires Turned Paupers
Antman tells the story of a client in the late ’90s who sought his help to minimize taxes on incentive stock options that had amassed enormous built-in gains.
“One of my earliest clients was working for a dot-com company that had given out incentive stock options, they had an enormous built-in gain, and they wanted to figure out the way to minimize taxes.”
Tongue-in-cheek, he suggested holding onto the stock until it crashed and gains disappeared, eliminating the tax problem.
The client took the hint and exercised the options, then immediately sold enough stock to become financially independent for life.
In contrast, many of the client’s colleagues exercised options with a plan to hold the stock for a day and a year in order to convert higher-taxed ordinary income to more lightly taxed long-term capital gains.
The stock collapsed before that day was to arrive for most of the client’s colleagues, and their gains were wiped out.
But that is not all. Antman says that these once paper-rich techies, by exercising their options, became subject to the alternative minimum tax (AMT) on phantom gains for which they received gigantic tax bills at a 28% rate. They could only begin to claw back those payments the following year — with capital losses limited to just $3,000 a year.
To make this more comprehensible, Antman says these tax-minimizing dot-com-ers — on options worth $1 million — would have received a $280,000 AMT bill just for exercising, then after the crash have $1 million worth of capital loss deductions they could use at a rate of $3,000 a year, which has some utility for those living to the age of 340.
“To be fair, several years later Congress passed a limited measure to allow some people to recover old capital losses from the AMT, but they still had to pay the $280,000 on the nonexistent gain and then wait several years for the government to show some mercy.” he says. “And that mercy rule has since expired, so we’re back to tax hell for such people the next time it happens.”