Situation
You have valuable private-company stock
Owning private-company stock that's worth real money — but isn't yet liquid — is its own situation. Exercise decisions are bets. AMT is a planning lever, not a tax. QSBS may or may not apply, depending on details you'd never think to check. This is the playbook for when there's value on paper and you want to keep it.
The Reading List
Articles, in order.
Work through them sequentially, or jump to the one most relevant to your situation.
- 01Opinion— EQUITY ADVANTAGE
Private Company Valuation: Is the Number Real… a Story... or BS?
Why private-company valuations can be technically real but economically misleading — four structural mechanisms employees should understand.
6 MIN6 MIN - 02Reference— FAQS
What Is My Pre-IPO Company Stock Worth? There Multiple Answers To This Question
Three (or more) valuations exist for your pre-IPO stock — VC preferred, 409A, secondary market — and none of them is truly 'the answer.'
1 MIN1 MIN - 03How-to— EQUITY 101
ISO Planning/Strategy
Two ISO decisions — exercise or wait, sell or hold — framed against your financial plan, taxes, and concentration risk.
5 MIN5 MIN - 04How-to— EQUITY 101
NSO Planning/Strategy
Two NSO decisions — exercise or wait, sell or hold — framed against your financial plan, taxes, and concentration risk.
5 MIN5 MIN - 05How-to— TAX STRATEGIES
Early Exercise (via 83(b) Election)
Filing 83(b) on early-exercised NSOs shifts future gains from ordinary income to capital gains and starts the LTCG and QSBS clocks immediately.
2 MIN2 MIN - 06Reference— EQUITY ADVANTAGE
Do Your Shares/Options Qualify for QSBS?
The 5-point checklist for whether your shares actually qualify for the QSBS capital-gains exclusion (and the misconceptions to avoid).
4 MIN4 MIN - 07How-to— TAX STRATEGIES
Multi-Year AMT Spread Riding
Exercise some ISOs each year up to your AMT free window, sell prior-year shares to widen next year's window — a multi-year plan to monetize ISOs as qualifying dispositions with minimal AMT.
5 MIN5 MIN - 08Reference— STEP-BY-STEP
Pre-IPO: Selling, Financing, or Exchanging Stock
How option-exercise financing, RSU loans, private-market exchanges, and pre-IPO exchange funds work — when each makes sense for a tech worker with trapped private-company wealth.
8 MIN8 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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