Matt Picheny
Matt Picheny has been a guest on Collecting Keys, the real estate investing podcast hosted by Mike DeHaan, Dan Austin and Dylan Koch.
From Taking 2 Years To Your First Deal to 1000 Units With Matt Picheny
Matt Picheny, a former actor turned multifamily syndicator, explains how he went from a two-unit Brooklyn townhome to sponsoring a 132-unit, $10 million deal in Kansas City — a process that took two full years and roughly 100+ underwritten deals before his first closing. He walks through how he picked markets where he already knew someone, built broker and property manager relationships by showing up in person, and paid for mentorship and coursework to fill knowledge gaps. He also shares a $52 million sale that nearly collapsed when the buyer showed up $5 million short on closing day.
Key takeaways
- Picheny's first syndication took two years of full-time work, and he underwrote well over 100 deals before one closed — he had assumed others in his mentorship group who took that long were slackers.
- Of his 10,000+ units, roughly two thirds are passive LP positions; only about 4,000 are deals he actually sponsors as a GP. He's upfront that citing the full number would be misleading.
- He chose markets (Akron, Central Florida, Kansas City) where he already had a relative or close friend, and Kansas City worked because he spent time there in person meeting brokers and property managers.
- Brokers don't get paid until closing, so they won't bring an unproven buyer to their client. Picheny built credibility by touring properties in the market and grabbing coffee with competing brokers, then closing one deal to prove he could perform.