The Equity Evolution

September 6, 2023

Exercising ISOs? You Might Owe Taxes!

"People who exercise ISO grants don't usually pay federal tax upon exercise." I've met enough people stuck with tens of thousands or even hundreds of thousands of dollars of unexpected taxes from ISO exercises to know this is a common and potentially devastating misconception.

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.

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.

September 12, 2023

Navigating Stock Option Repricing in the Face of Falling 409a Valuations

Falling 409a valuations have prompted many privately held tech companies to reprice their employees' stock options. Navigating stock option repricing necessitates a clear understanding of its implications, risks, and careful consideration of your personal circumstances and potential tax consequences, especially in the case of ISOs.

February 15, 2023

Worthless Securities: Reporting a Loss if Your Company Shuts Down

If you have equity in a startup that shut down, you can claim it as a loss on your taxes. But, it's not as simple as just writing them off as a total loss when you find out about it – the IRS wants you to claim the loss in the year the stock became worthless.

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.