The mechanics, with the math shown
What actually happens inside an angel secondary, step by step
The guide covers the overall shape of a sale. These 14 deep dives go further into the specific structures, rights, and tax rules that decide what a buyer or seller actually walks away with — each one worked through with real numbers.
Deal structures
SPV Secondaries
How a special-purpose vehicle pools many small buyers into a single line on the cap table.
Worked example →Direct Secondaries
Buying or selling actual shares, shareholder-to-shareholder, with no pooling vehicle in between.
Worked example →GP-Led Continuation Funds at Seed Stage
When a VC fund rolls a portfolio company into a new vehicle — and what that means if you co-invested as an angel.
Worked example →Selling a SAFE or Convertible Note, Not Shares
When there's no stock to transfer yet, because the instrument hasn't converted.
Worked example →Structuring a Partial Sale
Selling a slice of your stake instead of all of it — the mechanics of splitting a position.
Worked example →Rights & consent
ROFR & Transfer Consent, Step by Step
The right-of-first-refusal clock that determines whether your buyer actually gets the shares.
Worked example →Drag-Along vs. Tag-Along Rights
One clause can force you into a sale; the other lets you join one you'd otherwise be excluded from.
Worked example →Do Pro Rata Rights Transfer With a Secondary Sale?
Usually not automatically — a frequently wrong assumption on both sides of a secondary deal.
Worked example →Company Consent vs. Board Approval
Two different gates a transfer can hit — and one runs on a much slower clock than the other.
Worked example →Pricing, tax & closing
409A Valuation vs. Last-Round Pricing
Why the price on your common stock is usually well below the number in the last funding headline.
Worked example →QSBS & Section 1202: The Rule Secondary Buyers Miss
The single most commonly misunderstood tax point in this market — and it usually cuts against the buyer, not the seller.
Worked example →The 83(b) Election — What It Means If You're Buying Unvested Stock
A 30-day, non-extendable filing that matters if your secondary purchase comes with a vesting schedule attached.
Worked example →Escrow & Closing, Step by Step
What actually happens between a signed agreement and shares (or funds) actually moving.
Worked example →Valuing an Illiquid Stake
The comparable-round-plus-discount method most secondary prices actually use.
Worked example →None of this is investment or tax advice — it's a map of the mechanics, built to help you ask the right questions of a company, a buyer or seller, or your own advisor. For where these transactions actually happen, see where to buy pre-IPO and secondary shares; for real-world scenarios these mechanics play out in, see deal stories.