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 […]
ISO AMT and Cost Basis: What You Need to Know
If I had $1 for every time I had a conversation with smart-but-frazzled startup employees trying to understand the financial jargon around their ISO AMT, I could, well…. buy my wife and I a really nice dinner. 🥗 💑 🥂 Yeah, I know it’s not exactly millionaire lifestyle from that $1 per conversation, but it […]
How Does the AMT Credit Carryforward Work with ISO?
Guys, the Alternative Minimum Tax (AMT) & all. the. things. about it are confusing as heck. Like, that’s just how it is. I’m not even going to pretend with you right now. And unfortunately, it doesn’t look like the IRS is going to simplify the AMT credit carryforward with ISO anytime soon… so we’re doing our […]
How Do RSU Work: The Beginner’s Guide (Start Here)
Hands down, I find myself answering more questions about RSU (restricted stock units) than any other type of stock option. And it’s understandable: The way RSU work (not only with company vesting schedules but also with tax laws) is by far one of the most confusing financial concepts for startup or tech employees. But don’t […]
Double Trigger RSU Tax: 5 Ways to Avoid a Scary Tax Bill
First of all, if you’ve got a double trigger RSU that are about to settle. Congratulations! You’re about to come into a lot of money. Just be tax aware and avoid being caught unprepared by a scary tax bill. (And also, good on you for reading this article & being smart enough to figure out […]
ISO to NSO Conversion: Should You Convert Your Stock Options?
Ahh, the golden handcuffs. Those lovely things that keep you chained to your current job until the IPO. They’re not so bad if your company is going to IPO in a year or two, but with more and more companies delaying their IPO, it puts startup and private company employees in a pickle. Here’s why: […]
Selling Stock to Buy a House in 2024: Seven Steps
Buying a house is one of the biggest decisions of your life. ???? No matter where you live. Selling stock is a great strategy to buy a house with today’s high interest rates. But, it’s outright daunting. The basic numbers alone make it feel impossible: In San Francisco, the median home value in 2024 is […]
RSU Strategies for Tech Professionals with Landon Loveall
When you’re negotiating your compensation package, it’s easy to focus on the salary and maybe even the number of stock options you’re being offered. But how often do you consider the vesting schedule and how your equity accumulates over time? This is something I didn’t fully appreciate during my early career. Looking back at my […]
Cost Basis and RSU: THE Easy-to-Understand Tech Employee’s Guide
When you’ve got stock in a company, it’s normally a really, really good thing. Especially RSUs (or restricted stock units). They’re stock you get just by working in a company…. Ones you don’t even have to pay for. And any time those RSU shares “vest”—meaning the company hands ownership of them over to you—you become […]