A broker found my buyer in a week. The paperwork took four months.
The hardest part of this deal had nothing to do with finding someone who wanted my shares.
Angel investor, ~15 checks
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
- Logistics / supply chain
- Stage at entry
- Series A
- Original check
- $35,000
- Hold before sale
- 6 years
- Sold at
- 15% below Series D
- Time to close
- ~4 months
The matching was the fast part
A broker who specializes in this space had a buyer within a week — a family office looking for logistics exposure it had missed in the primary rounds. Price negotiation took another week. I thought I was nearly done.
Then it went quiet
The company's general counsel was juggling an acquisition and two other secondary requests at the same time, and mine went to the back of the queue. ROFR notice, waiver, updated cap table, transfer agreement, signature chasing across four parties — every step needed someone at the company to prioritize a favor for a shareholder who wasn't raising them money.
None of this was anyone acting in bad faith. It's just that a secondary transfer is a low-priority administrative task for a busy company, and it moves at the speed of whoever has the least incentive to hurry.
What I'd do differently
I'd set expectations with my buyer up front that four to six months is normal, not a red flag, so they didn't start wondering if something was wrong at month two. And I'd ask the broker to loop in the company's counsel earlier, before a price was even final, just to get the administrative machinery moving in parallel.
What to take from this
- A broker can source a buyer fast — the company's internal process is usually the real bottleneck.
- Set buyer expectations on timeline (3–6 months) before they get nervous mid-process.
- Get the company's counsel involved early, in parallel with price negotiation, not after.
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.