A sophisticated buyer wanted diligence materials I simply never had
I had shares to sell. I didn’t have five years of documents proving what I owned and why.
Early operator-turned-angel, one large legacy position
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
- Vertical SaaS
- Stage at entry
- Seed
- Original check
- $60,000
- Hold before attempt
- 7 years
- Buyer type
- Family office
- Outcome
- Repriced down, then closed
A buyer who diligenced like a primary investor
An individual buyer usually just wants your stock certificate, the company's last 409A, and a signature. A family office wanted that plus historical cap table snapshots, my original investment documents, confirmation of every subsequent amendment I'd consented to, and a representation that I had no side letters I'd forgotten about.
Seven years and one lost email account later, I genuinely could not produce all of it. I'd have to reconstruct my own paper trail through the company's records instead of my own.
The company had to vouch for me
The company's counsel ended up doing the reconstruction work — confirming share counts, pulling my original SAFE from their files, verifying there were no side agreements. That took real time from someone with no financial stake in my sale going through.
The buyer used the delay and the diligence gap as leverage. My original discount widened by another 6 points before we closed, framed as "compensation for the extra diligence burden." I didn't love it, but I understood it.
What I keep now
A folder — literally, and backed up — with every investment document, amendment, and side letter I've ever signed, for every position. It cost me nothing to make and would have saved me real money on this one deal alone.
What to take from this
- Keep every investment document and amendment for every position, indefinitely, backed up somewhere durable.
- A family-office or institutional buyer will diligence harder than an individual buyer — expect it.
- Diligence gaps get priced in as extra discount, not just extra time.
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.