Tag Archives: AMT


Qualified Small Business Stock Is An Often Overlooked Tax Windfall

Editor’s Note: This post was originally published on February 26, 2015. Given recent changes to the tax code, we are updating and re-publishing it. It’s no secret that small businesses have long been the growth engine of the US economy. With that in mind, Congress has packed the tax code with lots of breaks for those investing in small companies. One of the best, but little known breaks became permanent with the passage of the Protecting Americans from Tax Hikes (PATH) Act on December 18, 2015. I am referring to qualified small business stock (QSBS), a big reason for venture capitalists, angel investors, and entrepreneurs to smile in 2016 and beyond. What is QSBS? Like all things in tax, the IRS […]

Qualified Small Business Stock Is An Often Overlooked Tax Windfall

It’s no secret that small businesses have long been the growth engine of the US economy. With that in mind, over the years Congress has packed the tax code with lots of breaks for those investing in small business. One of the best breaks around — and no secret to experienced angel and venture capital investors in Silicon Valley — is qualified small business stock (QSBS). What Is QSBS? Like all things in tax, the IRS definition of qualified small business  can get complicated, and it changes depending on the section of the tax code in question. For our purposes, we’ll be focusing on Section 1202 of the Internal Revenue Code (IRC). To qualify as QSBS under Section 1202: The […]

When Should You Exercise Your Stock Options?

Stock options have value precisely because they are an option. The fact that you have an extended amount of time to decide whether and when to buy your employer’s stock at a fixed price should have tremendous value. That’s why publicly-traded stock options are valued higher than the amount by which the price of the underlying stock exceeds the exercise price (please see Why Employee Stock Options are More Valuable than Exchange-Traded Stock Options for a more detailed explanation). Your stock option loses its option value the moment you exercise because you no longer have flexibility around when and if you should exercise. As a result many people wonder when does it make sense to exercise an option. Tax Rates […]

Improving Tax Results for Your Stock Option or Restricted Stock Grant, Part 3

Wrapping It All Up: Tax Strategies In this third and final part to our series on the taxation of stock options and restricted stock units (RSUs), we’ll outline some strategies you can use to achieve better tax consequences. While the list below is definitely not comprehensive, it does cover some impactful strategies. Remember that — based on the various types of taxes described in Part 1 of this series — through good tax planning, you may be able to achieve a 19.6% improvement in your federal taxation rate. This improvement represents the difference between the federal ordinary income tax at 39.6% and the long-term capital gains rate at 20%. Early-Stage ISO Exercise and Hold While this may seem like it […]

Improving Tax Results for Your Stock Option or Restricted Stock Grant, Part 2

Applying the Tax Law to Common Employee Stock Situations In the first part of this three-part series, we discussed the four main taxes relevant to individuals. Now we’ll apply that knowledge to show what taxes would be incurred in five common situations faced by employees who work for venture-capital-backed companies. 1: Angel Investment or Founder Stock For many start-up companies, the first money in comes from angel investors or the founders themselves in exchange for preferred and common stock, respectively. In exchange for cash, investors (perhaps through a limited partnership) and founders receive shares of stock. The capital gains holding clock starts with the purchase of these shares, and it stops upon disposition of the stock. The shareholder realizes a […]

Improving Tax Results for Your Stock Option or Restricted Stock Grant, Part 1

Silicon Valley is again abuzz with stock option fever (and the option’s cousin, restricted stock units) due to several years of very successful local IPOs — but along with financial success often comes anxiety about taxes. To help assuage its clients’ fears, Wealthfront has asked me to write a three-part series that outlines what tax rates apply to individuals, how different types of stock options and restricted stock units (RSUs) are taxed, and some strategies to achieve improved tax results. Part 1: An Overview of Personal Tax Rates If you’ve already filed your 2013 tax returns, you may have noticed that your tax rates went up quite a bit from 2012. This is likely true if you reported income in […]

9 Signals You Should Hire A Tax Accountant

Many of our clients use TurboTax until they hit certain triggers in the complexity of their financial lives. If you spent more than a few hours on your taxes this year, it’s time to ask yourself whether it makes sense to outsource this portion of your financial life to an accountant. One of my rules in life – a rule that helps keep me balanced – is to outsource what I don’t enjoy or what someone else can do better than I. If you don’t enjoy something and you can hire someone to do it better than you can and it doesn’t cost too much, then doing so is a no-brainer. For many of our clients who are rising fast […]

Don’t Be Afraid Of The Tax Bogey On Your Stock Options

Many young executives worry about triggering taxes by exercising options. But, as Kent Williams, founding partner at Mohler, Nixon & Williams, and other tax experts will tell you, you could be passing up huge tax savings if you don’t purchase at least some of your shares now. Exercising options means you might have to pay income taxes up front, and possibly the Alternative Minimum Tax (AMT) on top of regular income taxes. That tax falls on the difference between the strike price and the value of the shares, usually determined by the board of directors of your company.  But that AMT can become a credit against the capital gains tax that you would have to pay when you sell your […]