Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

I got sold on a LIE

23 Dec 2025 · 0 min

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In this brief monologue, Christian Osgood recounts his personal experience managing a multi‑building real‑estate portfolio and reveals that, contrary to popular belief, real‑estate investing is far from passive for him. He describes waking up at 10 AM to collect physical rent checks, driving around each month to gather about $40,000 in paper payments despite 80 % of tenants paying online, and managing seven properties. Osgood characterises this hands‑on work as a “ripoff” and advises anyone seeking a truly passive investment to instead allocate funds to the S&P 500, which he believes will perform well without the active effort required in real‑estate management.

I got sold on the lie that real estate is a passive investment, and it's not. I got up at 10 AM today to pick up all these freaking checks. This is building number 1 of 7. Now, 80% of my tenants pay online, but I have like $40,000 of checks that I have to go get here myself manually, and this is not passive at all. This is a lot of work. I have to spend the first of every single month driving around a portfolio. This is a ripoff. If you're looking for a passive investment, just throw your money in the S&P. It will do fine.