Put $40k into a friend's brokerage. The headcount was real, the company dollar wasn't.
The pitch was 11 agents, a recognizable local name, and a founder who'd been in the business 14 years. I looked at agent count and closings and thought I understood the business. I didn't.
Prior year: 63 closed sides, average commission per side $8,400, so about $529k of gross commission income coming through the door. Average brokerage share across the roster was a hair under 20% because the top three producers were on 90/10 and everyone else was on 70/30. That's roughly $106k of company dollar for the year.
Overhead: office lease $4,200 a month, so $50k. A transaction coordinator at $46k loaded. E&O, MLS participation, association dues, tech stack, another $30k or so. Call it $126k against $106k. The business was underwater before anyone drew a salary, and the founder was covering the gap out of his own production, which is why nobody noticed for two years.
I paid $40k for 25%. Nine months later there was a capital call and I put in another $9k because I'd already anchored. The shop merged into a larger firm 14 months in, the acquirer paid for the roster and the trailing pipeline, and my share of that came to about $11k. Net loss $38k plus the time.
What I'd do differently: underwrite company dollar per agent per month against fixed overhead per agent per month and ignore headcount entirely. Eleven agents producing 5.7 sides each is a roster, not a business. And I'd read the capital call language before wiring, not after.