I sold a third of my stake at Series D and kept the rest
A $25k seed check I’d held for five years. I took some money off the table without giving up the upside.
Angel investor, ~12 checks, mostly fintech and dev tools
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
- Fintech (B2B payments)
- Stage at entry
- Seed (SAFE)
- Original check
- $25,000
- Hold before sale
- 5 years
- Sold at
- 18% below Series D
- Portion sold
- ~35% of position
What I was holding
I wrote a $25,000 check into a B2B payments company on a SAFE at the seed stage. On paper it had done well — the SAFE converted, the company raised a Series A, then a B, then a C, and the marks kept climbing. But “on paper” was the whole problem. Five years in, I had a number in a spreadsheet and nothing I could actually spend.
I wasn’t in trouble. I just didn’t love having that much of my net worth locked in one private company I no longer had any control over, with an exit that was, realistically, still years away.
How the sale came together
When the company started its Series D, a couple of the funds in the round wanted more allocation than the primary let them take. That’s the moment a secondary becomes easy: there’s a motivated buyer already looking at the same company, at a price everyone can anchor to.
I worked through a broker who’d handled a few of these for people in my angel group. We agreed I’d sell about a third of my position at roughly an 18% discount to the Series D price. The discount stung a little in the moment, but the buyer was taking my shares with fewer information rights than they’d get in the primary — the discount is what compensates them for that.
The paperwork was the actual work
The negotiation took a week. The transfer took two months. The company had a right of first refusal, so they had 30 days to either buy the shares themselves or waive it — they waived. Then there was company consent, an updated stock ledger, and a stack of transfer documents.
Nobody tells you that the “deal” is 10% of the effort and the transfer mechanics are the other 90%. If your company has a stock admin platform, it’s smoother. If it’s a spreadsheet and a busy CFO, budget more time.
Would I do it again
Yes. I converted five years of paper into real money, de-risked a position that had grown lopsided, and kept two-thirds of my shares for the eventual exit. Selling everything would have felt like a bet against the company; selling a slice felt like basic portfolio hygiene.
What to take from this
- Selling a portion, not all, lets you take money off the table without betting against the company.
- A new priced round creates natural demand and a clean price anchor for a secondary.
- Budget months, not days: ROFR window, company consent, and transfer paperwork dominate the timeline.
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.