Stock Options & RSUs RSS feed for this section

When and how much of your employee stock should you sell? How do you diversify your portfolio after an IPO? Understand what you need to consider in order to make sound decisions in exercising your employee stock options and RSUs, from start to vesting.



The Reason Offer Letters Don’t Include a Strike Price

A common frustration we often hear with offer letters from startups is the absence of an exercise price for the options being granted. Many people interpret this missing information as an intention by the potential employer to obfuscate. This is not the case. Only a board of directors — not the management team — can technically grant options and set their exercise prices, which is why your offer letter should say that your future employer will recommend your proposed offer  at the next board meeting. Boards typically only grant options when they meet, which for private companies can be anywhere from once a month to once a quarter depending on the company’s maturity. A 409A Is Needed to Set Fair […]

Introducing the Wealthfront Single-Stock Diversification Service

When LinkedIn went public in 2011, the company had about 1,500 employees. Traditional private wealth managers were ubiquitous on campus in their efforts to sign-up the 50 to 100 early employees and executives who met their firms’ multi-million dollar minimums. Unfortunately, that was of little help to the 1,400 other employees at the company looking for support. At Wealthfront, we believe everyone deserves sophisticated financial advice. Today, we’re launching the service I wish the entire LinkedIn team could have had access to back in 2011. Introducing the Wealthfront Single-Stock Diversification Service. This service will help solve a critical problem for many that work at public technology companies: How to best diversify concentrated holdings in your company’s stock. Such holdings are […]

The Math Behind the Single-Stock Diversification Service

At Wealthfront, we pride ourselves on combining world-class investment expertise with great engineering. So when we first set out to build the Single-Stock Diversification Service, building a product with unparalleled ease and convenience in solving a tricky client problem was not enough. Making recommendations to clients requires solid research and math. So, before we wrote our first line of code, we began looking at the two key questions faced by clients with large single-stock positions: Should I sell my single-stock position and diversify? If I am to sell, when and how should I do it? Should you sell your single-stock position? Many clients who speak to us about their single-stock position express some hesitancy in selling their company’s stock. After […]

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 […]

The Post-IPO Dilemma: Hedging Your Stock

If your company recently went public and your stock price has gone up significantly then you’re probably wondering how you can hedge your position. Unfortunately there’s nothing you can do while you’re still in the 180-day lock-up period. Most lockup agreements have extremely detailed restrictions included, designed to prevent almost any form of market participation with a security.  It’s too long to reproduce anything but a sample here, but it typically begins like this: In consideration of the Underwriters’ agreement to purchase and make the Public Offering of the Securities, and for other good and valuable consideration receipt of which is hereby acknowledged, the undersigned hereby agrees that, without the prior written consent of each of [names of managing underwriters], […]

WhatsApp: What an Acquisition Means for Employees

The announcement that Facebook is buying WhatsApp for $19 billion generated a lot of interest. The most popular question we received is what does the acquisition mean for the employees financially. IPOs tend to get all the headlines, but in many cases technology companies are acquired. This post will walk through the economics of an acquisition and how it affects all the parties involved. The Terms of the Deal From what I have read, Facebook will acquire WhatsApp for $4 billion in cash and approximately $12 billion worth of Facebook shares. In addition Facebook will grant $3 billion in RSUs to founders and employees that will vest over the next four years. I do not have any special insight into […]

When Success & Stock Options Make It Expensive to Leave

They can be an incredibly rewarding and inviting incentive. And among those working in Silicon Valley stock options have become an inextricable part of most job offers. However, actually benefitting from them is not always as easy as you might think. Employees who decide to leave mid-sized companies often awaken to a pretty big and increasingly common surprise — they can’t afford to exercise their options. In our post The 14 Crucial Questions About Stock Options we discuss the questions you need to ask about the stock option component of your offer before you join a new company. We specifically didn’t address how long you see yourself staying with the new employer or when the company is likely to go […]

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 […]