Situation
You're changing jobs with vested equity
Leaving a company isn't just an HR transition — it starts a clock on your equity. ISOs convert to NSOs after 90 days. Unvested RSUs vanish. Refresh grants from the new company need to be sized against what you're walking away from. The choices you make in the first 30 days matter most.
The Reading List
Articles, in order.
Work through them sequentially, or jump to the one most relevant to your situation.
- 01How-to— JOBS & LIFE
Leaving Your Company
What to decide when you leave a tech employer: exercise vs. let lapse, the 90-day window, and what you can still negotiate on the way out.
6 MIN6 MIN - 02Reference— JOBS & LIFE
Changing Jobs/Employers
Three decisions when changing employers: vested options, new-employer evaluation, and what to negotiate.
1 MIN1 MIN - 03How-to— TAX STRATEGIES
Exercise ISOs Within 90 Days After You Leave a Company
IRS rules convert vested ISOs to NSOs 90 days after termination — exercise inside that window to keep the qualifying-disposition tax benefits intact.
3 MIN3 MIN - 04How-to— EQUITY ADVANTAGE
Negotiating an Option Extension/PTEP when LEAVING a company
Five strategies for negotiating a PTEP (post-termination exercise period) when leaving — the pros, risks, and trust required for each.
7 MIN7 MIN - 05How-to— JOBS & LIFE
Key Questions To Ask & Negotiation Strategies When Changing Jobs
Questions to ask a new employer about equity, what's actually negotiable beyond salary, and executive-only items.
8 MIN8 MIN - 06How-to— JOBS & LIFE
Choosing A New Company To Work For
How to evaluate a pre-IPO employer the way a VC would — top investors, founder track record, stage, product type, and exit rates.
5 MIN5 MIN - 07How-to— EQUITY ADVANTAGE
Joining a Startup? 7 KEY Questions To Ask/Know About Your Equity Grant
Seven questions to ask before signing a startup offer: percent ownership, vesting, 83(b), PTEP, liquidation prefs, secondaries, and 409A.
6 MIN6 MIN
Talk to a 30/40 Advisor
Want this applied to your situation?
A 30-minute consult tells you whether the frameworks in this reading list cleanly apply to your equity package — and if so, what the first three moves are. No pitch.
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