A divorce settlement needed a number for my startup shares. Getting one was its own project.
I wasn’t ready to sell. The settlement process needed to know what the shares were worth either way.
Angel investor navigating a divorce settlement
Illustrative composite. A representative scenario built from how angel secondaries commonly play out — realistic numbers, written in the first person, not the record of a specific named person or company.
Deal snapshot
- Side
- Selling
- Sector
- Biotech tools
- Stage at entry
- Seed
- Original check
- $28,000
- Hold before sale
- 5 years
- Reason for sale
- Divorce settlement
- Sold at
- 22% below last round
A number that had to exist, ready or not
My divorce settlement required a valuation of everything in the marital estate, including an illiquid startup position that, by its nature, doesn't have a public price. Getting a defensible number meant either a formal 409A-style appraisal or an actual sale, since a real transaction is the cleanest evidence of fair value a settlement negotiation will accept.
Choosing to sell rather than appraise
An appraisal alone would have satisfied the paperwork but left me still holding an illiquid asset while everything else in the settlement got divided and closed out. I decided to actually sell through a broker instead, converting the position to cash that could be split cleanly like everything else, rather than leaving one asset lingering as a loose end.
What made this different from an ordinary secondary
The timeline wasn't mine to control — the settlement had its own legal deadlines, which meant less room to shop for the best buyer or wait for a better moment. The 22% discount reflected that time pressure as much as anything about the company itself. It wasn't the sale I would have chosen on my own schedule, but it closed the settlement cleanly.
What to take from this
- A real transaction is often more defensible in a legal settlement than a paper appraisal of an illiquid position.
- External deadlines (legal, tax, personal) remove your negotiating leverage on timing — expect a wider discount.
- Consider whether converting an illiquid asset to cash simplifies a broader settlement, even at a worse price.
Every angel who has held a position long enough eventually faces a version of this decision. For the mechanics behind stories like this one, see the guide to how secondaries work.