Situation
Your company is going public
An IPO is a multi-year event compressed into 18 months of decisions. Pre-IPO: exercise sequencing and AMT planning. Lockup: a 180-day period where you can plan but not act. Post-IPO year one: the largest tax year of your life, executed through a 10b5-1. Each phase has its own playbook.
The Reading List
Articles, in order.
Work through them sequentially, or jump to the one most relevant to your situation.
- 01Reference— LIQUIDITY EVENTS
IPO/Going Public
IPO mechanics: why companies go public, how it changes your RSUs and options, the new restrictions, and your selling plan.
13 MIN13 MIN - 02How-to— STEP-BY-STEP
Pre-IPO: Key Decisions To Make
For VC-backed pre-IPO employees, the central decision is whether to exercise — work through it across ability, conviction, tax motivators, and liquidity/employment plans.
4 MIN4 MIN - 03How-to— EQUITY ADVANTAGE
The IPO Millionaire’s 180 Day Lockup Playbook
Use your post-IPO lockup as planning time: build a financial plan, define a stock strategy, and stage your tax-optimization moves.
5 MIN5 MIN - 04Opinion— EQUITY ADVANTAGE
Leaving Money on the Table: The Logic Behind 2025's IPO Underpricing
Why 2025 IPOs are systematically underpricing: companies prioritize public access, VCs need liquidity, banks want momentum.
3 MIN3 MIN - 05How-to— STEP-BY-STEP
Public Company: Key Decisions To Make
Once your company is public, your two planning vectors are a systematic selling/diversification plan and tax optimization across new tools (ESPP, 10b5-1) and restrictions.
3 MIN3 MIN - 06How-to— TAX STRATEGIES
Design and Implement a 10b5-1 Selling Plan
How a 10b5-1 plan schedules stock sales in advance — required for pre-clearance individuals, useful for systematic selling — and trades flexibility for insider-trading protection.
5 MIN5 MIN - 07How-to— EQUITY ADVANTAGE
Navigating Post-IPO Wealth: Tax Optimization and Portfolio Strategy for a $1.5M Income Event
A $1.5M post-IPO income event end-to-end: DAF giving, hedge-fund losses, 130/30, exchange fund, regret-minimized selling plan.
7 MIN7 MIN - 08How-to— TAX STRATEGIES
Correcting Cost Basis of Shares from NSOs Post-IPO
Brokers list pre-IPO NSO cost basis at strike, but your tax basis is FMV at exercise — make sure your CPA adjusts it on Schedule D or you'll overpay capital gains tax.
2 MIN2 MIN
Talk to a 30/40 Advisor
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