Tag Archives: RSUs


How New College Grads Should Approach Stock Compensation

Over the past two years we have written numerous posts to help you evaluate job offers that include stock options or Restricted Stock Units (RSUs). We assumed in all our posts that job seekers were evaluating offers from companies at a similar level of maturity. For many new graduates, however, the comparison gets more complex if you aren’t sure whether you want to join a very mature company like Google or an earlier stage company like one of our recommended mid-sized companies with momentum. The purpose of this post is to help make that task much simpler. The Mechanics of Stock Options Let’s start with the basics of stock compensation. A stock option gives you the right to buy common […]

How to Trade Salary for Equity

These days it’s more important than ever to maximize the financial value you extract from your job. In You Need Equity To Live In Silicon Valley we made the case that it’s very hard for a Silicon Valley based couple who earns $250,000 per year to afford to buy a home and put their kids through college without generating wealth from an equity stake in a private company. We have written numerous posts to help you identify the kind of employer that is most likely to help you achieve your goals (peruse the Careers section of our blog to see them). This post focuses on how you might think about trading off some salary for additional equity, something we are […]

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 […]

How Do Stock Options and RSUs Differ?

One of the biggest changes in the structure of Silicon Valley private company compensation over the past five years has been the increasing use of Restricted Stock Units (RSUs). I’ve been in the technology business more than 30 years and throughout that time stock options have almost exclusively been the means by which startup employees shared in their employers’ success. That all changed in 2007 when Microsoft invested in Facebook. To understand why RSUs emerged as a popular form of compensation, we need to look at how RSUs and stock options differ. History of the Stock Option in Silicon Valley More than 40 years ago a very intelligent attorney in Silicon Valley designed a capital structure for startups that helped […]

An Employee Perspective on Equity

Andy Rachleff, Wealthfront's President & CEO

A couple of days ago we wrote a post for company founders that describes our proposal for allocating equity to attract and retain outstanding employees.  We call it the Wealthfront Equity Plan. It’s equally important to take a look at the Wealthfront Equity Plan from the perspective of an employee. When a prospective employee is considering a job offer she should be concerned not only with the amount of options she receives when she joins a company but also how well she is going to be rewarded for outstanding performance. Back in April 2012 we wrote a blog post that listed the 12 questions you should ask about the options associated with your job offer (NOTE: We have since updated and […]

Manage Vested RSUs Like A Cash Bonus & Consider Selling

If your company gave you a year-end bonus of $100,000, would you use all of it to buy your company’s stock? Hell, no. Yet, scores of our clients who own restricted stock units and work for Facebook or Google effectively have. You see, restricted stock units (RSUs) are taxed differently than stock options, and many employees who receive RSUs don’t understand the implications. Stock options have a tax advantage: they are taxed when you exercise, so you might have an incentive to sell the following year and take the gain or loss. Not so with RSUs. They are taxed at the time they are vested, not when you sell. Facebook, for instance, even withholds the taxes due on RSUs by […]