When Should I Exercise My Private Company Stock Options?
Getting more stock options from your employer is always a good thing. After all, if you’re helping to grow a business, it makes sense to share in its success. I’ll always be a fan of my clients having as many stock options available as possible, but the truth is, in private companies, there’s a catch… […]
When to Exercise Stock Options Startup and Before IPO
Deciding when to exercise stock options in your startup before it’s sold or has an IPO can be a pretty sticky situation. For one, you have no idea what’s going to happen in the future: your startup could have a successful IPO and you could make millions because you decided to exercise your options now… […]
How Much of My Company Stock Should I Own? – 3 Steps
Most of the time, tech employees think it’s a good idea to keep “some, but not all” of their company stock. And as long as they believe in the company, we agree with them 110%. The only problem is, “some but not all” is not a specific number. If you don’t know what that specific […]
Employee Stock Options Explained: How to Avoid 3 Killer Mistakes
Employee stocks options is a long, complex topic that we simplify by helping you avoid the three killer mistakes. You know them well: Surprise huge tax bills Over concentration in single tech stocks Too much cash sitting around not invested Together they will leave your employee stock option and RSU plan bloodied and bruised. We […]
Alternative Minimum Tax ISO: How Does It Work
Alternative minimum tax (AMT) on Incentive Stock Options, or ISO, is so confusing. You don’t receive any cash when you exercise ISO and pay ordinary income tax when you exercise your options. But you could have to pay the alternative minimum tax. Here is what you need to know now. Alternative Minimum Tax on ISO […]
5 Lessons Learned from Missing Cost Basis
How do you calculate missing cost basis? What lessons can you learn? What might you want to do differently in the future? This post will answer those questions and show how to avoid paying unnecessary taxes because of missing cost basis. What is cost basis? Cost basis is the total price you paid to buy […]
Private Company Stock Options: Things to Know Now
In any private tech company, there are typically five types of stock options available: QSBS (qualified small business stock) LTCG (long-term capital gains) Shares Unexercised ISO (incentive stock options) Unexercised NQSO (non qualified stock options) RSU (restricted stock units) And if your eyes glazed over looking at that list, I don’t blame you. Only nerdy […]
When to Sell Stock Options: Learn Stock Option Type & Time to Sell
Having stock options, RSUs, or an ESPP as part of your compensation package can be a great way to build wealth. What’s not so great? When you don’t know when to sell stock options, or what moves to make based on their different types. You might be asking yourself: After all… taxes? (Some stock options […]
ISO Cashless Exercise Now vs. Wait & Exercise Later
Imagine a typical job searcher in Silicon Valley: She took a job at a tech company, and part of her compensation package was ISO (incentive stock options), but she assumed they wouldn’t be worth anything, so she didn’t bother with them. But then, suddenly, the company improved and an IPO was on the horizon. She […]