Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

"Friend" squatted then stole his Rent

24 Oct 2025 · 1 min

Watch on YouTube

0:46

In this personal anecdote, the speaker—an inexperienced first‑year rental property investor and single parent—rented a unit to a friend without a written lease, assuming trust would suffice. The friend sub‑leased the property to another tenant, stopped paying rent, and eventually moved out, leaving the speaker to confront an unoccupied house and a new tenant with a lease. The speaker attempted an eviction, which resulted in the tenant leaving voluntarily, but the speaker incurred a $6,000 loss for that year. Reflecting on the experience, the speaker highlights key lessons: always use a formal lease, rigorously screen tenants, avoid renting to friends, and consider cash‑for‑keys as a proactive exit strategy.

Chapters

Well, since I'm not a real landlord, I couldn't trust a stranger, so I rented to a friend. And then, you know, it's a friend, so who wants a contract between buddies? So I didn't have a lease. I was a single parent. So this is in my first year of investing. It's been a decade since I've had a late or missing rent payment. But in that first year, wow, rent became late, late became never. So when I went to the house to talk to him, he didn't live there. He had moved out, rented the house to somebody else with a lease. So he was doing it better than me and he was making money. So I went through an almost eviction with that tenant. They ended up willingly moving out. I didn't know about cash for keys at the time, but I probably would've done that. I lost like $6,000 that year. But the biggest mistake was a real landlord would find a lease, screen tenants, not rent to a friend. Sometimes people just get shitty, but subleasing and taking a profit to not pay you and then be like, oh yeah, we're buddies.