How to Avoid IRS and California Tax Underpayment Penalty on RSU and Stock Options
Contrary to your standard worker, tech employees have several different types of income. (Well, maybe not SO MANY, but there are more than a few… which is significantly more than most people who just have to count their paychecks.) Especially after an IPO. And that’s great, because it means you’ve got more than one way to […]
Your Relationship with Money
They say more money means more problems, and it’s easy to see why. As your career grows, so do the demands of life. Balancing a flourishing career with a mortgage, kids, and a more comfortable lifestyle can be overwhelming. So we’d like to counter that more money often presents different challenges-ones that you might not […]
Exercise and Sell or Exercise and Hold – Stock Options Case Study
So your company just announced a tender offer or IPO. The rubber is about to meet the road, and you’ve got some decisions to make about what you’re going to do with your incentive stock options (ISO).You finally have the chance to cash in on your stock options, and if you’ve got the extra cash […]
Stripe Tender Offer: 7 Expert Tips to Protect Your Money
Here’s how Stripe employees can avoid high taxes and maximize their financial gains from the new tender offer. Stripe employees and alumni were recently met with a tender offer by the fintech, enabling them to sell restricted stock units (RSUs), shares, and options expiring in the next two years for a potentially big payday. (In […]
ISO AMT and Cost Basis: What You Need to Know
If I had $1 for every time I spoke with smart (but slightly frazzled) startup employees trying to make sense of ISO AMT jargon, I could treat my wife and myself to a very nice dinner. 🥗 💑 🥂 Yeah, I know it’s not exactly millionaire lifestyle from that $1 per conversation, but it is […]
Selling Early Employee Equity in a Startup Fundraising Round
Over the last few years, we’ve noticed a BIG trend growing in our clients who work for startups: The opportunity for selling early employee equity in a startup fundraising round. In the past, startup companies would go from zero to IPO in just a few years, but now lots of companies are taking ten years or […]
How to Plan Around Trading Windows
Going to jail for insider trading is no good. Thankfully, though, there are ways you can legally buy and sell stock in the company you work for to build wealth without going rogue. A trading window gives employees an opportunity to sell their shares without worrying about violating insider trading laws or dealing with the […]
What is Supplemental Pay?: Bonus, RSU, NQ Withholding
In the tech world, it happens all the time: Employees get supplemental pay beyond their base income. They file their tax returns, reporting these wages just like they’re supposed to. And then they end up with huge tax bills because the withholdings their employer took out of their paychecks weren’t enough. It sucks. And leaves […]
Tender Offer Tax Treatment: 5 Keys to Tax and Investing Cash After
We’ve been helping tech employees navigate tender offer tax treatment since 2017… and over the years, these tender offers have become increasingly common in the tech world. Think of a tender offer as your pre-IPO moment: it’s often the first time you can both exercise and sell your stock options, resulting in a sizeable lump […]