Exercise Stock Options After Leaving: the 90-Day Limit

Maybe you’ve gotten a job elsewhere, been laid off, or are taking that long-awaited sabbatical. Unfortunately, you’ve just realized that moving on to the next thing wasn’t as easy as sending goodbye messages to your work buddies on Slack and turning in the company laptop. Unbeknownst to you, your financial life just got a lot […]
Leaving Your Company? By Hire or Fire – Here Are Your Top 3 Tax Considerations

We’re all seeing it: It feels like every other week there’s another LinkedIn announcement of one company or another downsizing its workforce, especially in the tech industry. Which means a lot of people have already had to switch their jobs this year, and because of the public nature of these layoffs, a lot more are […]
Should I Set Up a 10(b)5-1 Plan?

Is a 10(b)5-1 plan a good idea? Or will it keep you trapped in a bad stock market? What if the stock price spikes beyond what you expected? Read here.
Withholding Tax on Stock Options: The Good, The Bad, The Ugly

No one likes an unexpected tax bill. ???? No one. And yet, it happens all the time. Even to smart people. Really smart people. Especially, in our experience, smart people with stock options. Why is that? And how can you make sure you avoid getting an unexpected tax bill or a slap on the wrist […]
When does an 83(b) election make sense?

Most of our advice on this blog surrounds exercising and selling stock options after they vest. But did you know that you can (sometimes) go ahead and pay taxes on your options before they vest? You can! And it’s via a Section 83(b) election. This can be incredibly handy for saving money on future tax […]
What are the Best Investments to Pair with Employee Stock Options?

Anytime we have a client with stock options and an IPO in the future (which is often), we build their financial plan around five key areas: Career Stock Options Taxes Cash Flow Investments You’ll notice that stock options are #2 and investments are #5… Yet so many of our clients want to jump the gun […]
Employee Stock Purchase Plan (ESPP) 101: How Does an ESPP Work?

Most people are pretty giddy when they get their first job with a stock options package. After all… what is there to not be excited about? If you’re confident in your company and your teammates’ abilities to do their jobs well, it’s a built-in opportunity to grow your wealth that doesn’t require a massive […]
The Impact of Inflation on the Stock Market (And Your Stock Option Plan)

It’s all over the news, and it’s natural to start worrying about: Inflation. Inflation, inflation, inflation. ???????? We’re seeing it at the grocery stores and in the prices of most consumer goods: they’re more expensive now than they were a year ago. It’s impossible to ignore. And many people are starting to wonder what the […]
Are SMAs the Future of Personalized Investing? How to Invest & Grow Your Stock Option Wealth With an SMA

In this article we’ll talk about how individual investing has evolved over time, and why Separately Managed Accounts (SMAs) could very well be the future of personalized investing. Especially when you consider the recent decrease in their investment requirement, SMAs could be a total game-changer for many young professionals building long-term wealth. When it […]