I bought secondary shares weeks before the IPO. The lockup expiration tanked the price.
I got the company right. I got the timing of my own exit badly wrong.
Individual investor, buying through a marketplace
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
- Buying
- Sector
- Enterprise SaaS
- Stage at purchase
- Pre-IPO, ~2 months before listing
- Amount deployed
- $35,000
- Bought at
- 5% below last private round
- Lockup period
- 180 days post-IPO
- Price at lockup expiry
- ~30% below my entry
A confident, late-stage bet
I bought in through a marketplace two months before the company's IPO was formally announced, at a modest discount to its last private round. The company was real, profitable, and well-regarded — this felt like one of the safer secondary bets I'd make.
What I didn't model
My shares, like everyone else's, were locked up for 180 days after the IPO — standard practice, and something I knew about abstractly but hadn't really priced into my thinking. What I hadn't modeled was how predictable the stock's behavior would be right at that lockup expiration: a wall of early investors and employees, all released to sell on the same day, hit the market at once, and the price dropped roughly 30% in the two weeks around the unlock.
I hadn't planned to sell exactly at expiration, but I also hadn't planned around it, and I ended up watching a chunk of my paper gains evaporate in a move that, in hindsight, was almost mechanically predictable.
What I model now
Lockup expiration dates are public information once a company IPOs, and the price pressure around them is a well-documented pattern, not a surprise. I now treat the lockup date as a real event to plan around — either exit meaningfully before it or be prepared to hold through the dip rather than getting caught deciding in the moment.
What to take from this
- Post-IPO lockups (commonly 180 days) release a wave of shares onto the market on a known, public date.
- Price pressure around lockup expiration is a well-documented pattern — plan your own exit around it, not by reacting to it.
- Being right about the company doesn't protect you from being wrong about your own timing.
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.