Real Estate Underground
Real Estate Underground
Ed Mathews
Investors Don't Invest in Deals: Shams Merchant on ChatGPT, the 506(c) Default and What LPs Actually Check
43 minutes Posted Aug 18, 2026 at 3:59 pm.
Investors don't invest in deals, they invest in sponsors
Welcome to Real Estate Underground
Meet Shams Merchant
What a real estate securities attorney actually does
Leaving the big firm: what it was worth and what it cost
Why can't I just use ChatGPT to write my PPM?
Lawyers as a risk-shifting mechanism
What you are actually paying for
What LPs check now: green, yellow, and red lights
Fee stacking, clawbacks, and real alignment
GP contribution has to be actual cash
506(b) vs 506(c)
Why Shams defaults to 506(c) every time
The exception: the NBA player's text thread
No over-lawyering: flat fees, unlimited revisions
Where Shams invests, and the fund-of-funds model
Asset classes, and multifamily's quiet comeback
Data centers vs flex industrial
The Northeast case for flex: nobody is moving
Would you go to college today?
One person can run a $200 million deal now
The baby lawyer problem: no juniors, no seniors
The Final Five
Best advice: legal work is a commodity
The decision he'd take back
On the nightstand
F1, McLaren, and learning golf at thirty
How to reach Shams
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Show notes
Shams Merchant structures syndications and investment funds for clients across the country. He also runs his own fund-of-funds, allocating LP capital across about fifty sponsors, which means he sees both sides of the table: he writes the documents, and he reads other people's documents deciding whether to invest. That vantage point is what makes this episode useful. On AI: he gets the ChatGPT question weekly now. His answer is not that the technology is bad, he uses it heavily. It is that a m...