BRINGING YOU KNOWLEDGE ABOUT EQUITY COMPENSATION
AND OTHER PERSONAL FINANCIAL TOPICS
September 25, 2023
Avoiding the Biggest Backdoor Roth IRA Conversion Mistake (It's Not What You Think)
The most common mistake I see with backdoor Roth conversions is unintentionally running afoul of the IRA aggregation rule, but to me, the true biggest backdoor Roth IRA conversion mistake is improper tax reporting.
November 7, 2023
COBRA Continuation - An Overview
COBRA continuation allows employees covered by workplace health insurance plans to keep their health plan while they’re in between jobs, taking time off, or would temporarily prefer their old insurance over current options.
August 21, 2023
Exercising Underwater Stock Options - Possibly Justifiable or Always an Illogical Decision?
A client recently asked me if it would ever make sense to exercise underwater stock options and if it could lower their AMT. Many companies have experienced downward revisions to their 409a valuations over the last year-and-a-half due to the shakeups in the tech sector, so I'm hoping this will help other people who have underwater stock options and are wondering the same thing.
October 24, 2023
Why Liquidity Preferences and Distribution Waterfalls Matter to Startup Employees
For equity-compensated employees in venture-backed startups, understanding the intricacies of liquidity preferences and distribution waterfalls isn't just a matter of curiosity but something that can directly impact the value of their equity.
October 31, 2023
Understanding Trustee-to-Trustee Transfers, Direct Rollovers, and Indirect Rollovers
There will likely be at least one point during your career when you'll want to roll an old 401k or IRA into another retirement account. To accomplish this while preserving the tax advantages of your retirement accounts, you have three options: trustee-to-trustee transfers, direct rollovers, and indirect rollovers.
January 18, 2023
Nondeductible IRAs - Not Very Tax-Advantaged
Nondeductible IRA contributions are similar to a Roth IRA in the sense that contributions are made after tax in both cases. The huge and extremely important difference is that the earnings on nondeductible contributions to a Traditional IRA are fully taxable at distribution, while the earnings on Roth IRA contributions are tax-free.