[Dwolb]

If you’re up for QSBS treatment, I’d recommend to hire a CPA, financial advisor, and possibly a lawyer.

One of those three can send over a letter to the CEO or CFO to share relevant information. It’s usually already prepared for equity or debt financing rounds and possibly periodic reporting.

[toomuchtodo]

Appreciate the advice. Are there cut offs similar to an 83b election? Or can QSBS still apply if you're near the end of the five year wait period and you took no action at grant and exercise events (besides what you normally might for an ISO grant)? Asking so I'm not wasting the time of the involved.

[Dwolb]

I need to say the obligatory THIS IS NOT FINANCIAL ADVICE CONSULT A TAX ACCOUNTANT.

Ok so my understanding is you need to exercise your options and wait 5 years for QSBS to kick in. After that you can start selling at $0 in capital gains.

Just a heads up though, this tax treatment may get closed soon with upcoming federal legislation. May not apply to shares exercised prior to the legislation being enacted though.

Note: here are some people who talk about QSBS as well https://www.mossadams.com/articles/2021/04/qualified-small-b...

[toomuchtodo]

No worries, understood, hold harmless and all that jazz. Thank you for the time and the info.

[Dwolb]

Yup, good luck.

[toast0]

83b has reporting requirements (you've got to send it in within x days of exercise and again with your 1040 for that tax year, although the second one is maybe not super required: regulations say you must send it, but I think there's rulings that say otherwise), but QSBS doesn't really: you just say some of your capital gains (more or less) don't count on the QSBS form. Only if you're audited do you provide documentation.