ISO Disqualifying Disposition: How You Can Minimize Your Taxes
Though you may not realize it, tech employees have wealth-building tools at their fingertips. If used strategically, these tools can help professionals achieve some of their loftiest financial goals. Incentive stock options (ISO) are just one avenue you can take advantage of, however they don’t come without a learning curve and mistakes with ISO disqualifying […]
QSBS Stock Options: Qualified Small Business Stock and 100% Tax Exclusions
We know the IRS loves to make sure they get their fair share of taxes… So is it ~really~ true that they’d allow 100% tax exclusions on QSBS stock options? Believe it or not… yes! Owners of qualified small business stock (QSBS) can be eligible for tax-free capital gains on their federal taxes for up […]
ISO AMT Tax: What You Need to Know
ISO AMT tax is a real doozy. In fact, a lot of people are still confused about what it all means. We’re seasoned with working with tech employees who are frequently affected by things like ISO AMT tax, so we wanted to help you understand how these tax laws will affect you if you choose […]
When to Sell Stock Options: Learn Stock Option Type & Time to Sell
It feels good when you’ve got different stock options, RSU, and ESPP to work with to grow your wealth. What doesn’t feel good is when you don’t know when to sell stock options, or what moves to make based on their different types. Like, should I sell RSU or ESPP first? When to sell stock […]
How to Avoid IRS and California Tax Underpayment Penalty on RSU and Stock Options
Contrary to your standard worker, tech employees have SO MANY 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 expand […]
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 […]
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 […]
Stripe RSU: Here’s How the New Tender Offer Affects Your Money
The company’s new tender offer gives current and former employees who hold Stripe RSU a big, potential payday. It’s generally been a dry season for IPOs, with companies’ plans frozen and in limbo. Whenever we see a possible IPO, it somehow gets forestalled — the most recent of which is fintech Stripe. To understand the […]
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 […]