#21 | Stock Options, Common Tax Mistakes and Secrets

Practical Tax with Steve Moskowitz

In this Episode, Steve and Cliff discuss common tax issues with Stock Options. This discussion is aimed at the employee who receives stock options as part of their compensation. Discussion of Tax Strategies for ESOP, RSUs, and ISOs. 83b elections, tax timing and rules and common tax preparation mistakes. Listen to the full episode to learn more! Episode Transcript Intro: You're listening to the Practical Tax podcast with tax attorney Steve Moskowitz. The Practical Tax podcast is brought to you by Moskowitz LLP, a tax law firm. Steve Moskowitz: Welcome back, folks. This is Steve Moskowitz and Cliff Capdevielle, and we wanna show you how we can save you some taxes. I'm the head of the firm, I am a tax attorney, and before I was a tax attorney I was a CPA. I started life off in a big firm, and then opened up my own practice many years ago. My friend and colleague, Cliff Capdevielle, is also a tax attorney and accountant. He also came out of a big firm. And there's so much here that we wanna talk to you about. A lot of times when you go to work someplace, they say, "Well, your salary is so much, "but we're gonna give you extra benefits "like stock options." And one of the things that you say, "Well, okay, that's good, "but I wanna do what the wealthy do, "I wanna go ahead and make all kinds of money, "and take all kinds of tax advantages of this." So you have a stock option. There's something that you should know about called an 83 election. And basically what an 83 election will do for you, is greatly reduce the amount of taxes which you have to pay on that stock option. And you say, "What's 83 , Steve?" Well, that one refers to 83 in the Internal Revenue Code. But Cliff, tell us about what's an 83 election. Cliff Capdevielle: Sure, so what you wanna do when you're planning for employee stock options, is make sure that to the extent possible, you are capturing any gains as long-term capital gains versus short-term capital gains. Steve Moskowitz: What's the advantage between capital gains and ordinary income tax, Cliff Cliff Capdevielle: And it's huge, it is huge, Steve. It's almost double. So ordinary rate for most people is 30 to 37%, guess what, if you can convert ordinary income to capital gains, you can reduce that rate to 20% or below. So you're essentially cutting your tax in half if you do that, Steve. Steve Moskowitz: Well, I like cutting the tax in half, and I would be willing to venture, Cliff, that everybody watching this or listening to this would like to cut their tax in half too. So, okay, this is great. Tell me how do I cut my tax in half? Cliff Capdevielle: Yeah, so with an 83 election, you essentially notify the government that you're picking up an income, a very small amount, which is the the fair market value on the date that the options are granted to you and you pick that up, and that starts the running of the holding period for capital gains rate. So in other words, if you hold that stock more than a year, you've converted what would typically be ordinary income tax at ordinary income rates to capital gains rates. So it makes a huge difference. And we see a lot of mistakes, Steve, unfortunately. Steve Moskowitz: Whole lots of mistakes here. Cliff Capdevielle: With the startups in Silicon Valley and even with mature companies, we see major mistakes when people go to their local CPA firm or their local tax preparer, not making these basis adjustments, not calculating the capital gain rates, it's unfortunate these laws are pretty complicated, and if you don't know how they work, you can end up paying a lot more tax than you need to. I'll give you an example, with non-qualified stock options. These are typically called RSUs, sometimes ESPP. These options are actually included in the gross income part of wages, so these are actually included in W-2 wages. Guess what? Oftentimes the broker dealer will report these without the basis adjustment. In other words,