Should I Set Up a 10(b)5-1 Plan?

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

blog-withholding-tax-stock-options

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?

83b election

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?

best investments with 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?

how does ESPP work, Employee Stock Purchase Plan (ESPP)

  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)

impact of inflation on stock market

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 […]

Start Here: Understand Cost Basis & Cost Basis Implications

cost basis implications

Keeping it simple, cost basis is the original price you pay for an asset. It’s used as a starting point to calculate how much you earn on an asset, so the IRS knows how much to charge you for capital gains tax.  Sounds pretty simple, right? In theory, yes.  But in practice…. not so much. […]

IPO Planning for Your First IPO: Start Here Guide

ipo planning guide

For most tech employees, finding out an IPO is on the horizon is like a sailor seeing land for the first time in months: They know their hard work & risk-taking has paid off, and they’re about to be rewarded with the excitement and freedom that comes with this new financial territory.  And it really […]