Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

The Dumbest Thing I Ever Bought

31 Jan 2024 · 0 min

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Christian Osgood bought a massive resort property that consumed enormous time and resources. He hired a team with no hospitality experience, so he and his wife ended up managing it themselves. Financially it worked, but strategically it was the wrong move.

What's the dumbest thing you ever bought? The dumbest thing I've ever bought? Oh yeah, Robin Hood. The dumbest thing I ever bought was the largest property we ever bought. It was a huge resort that took a bunch of our time, a bunch of our resources. The other thing we did wrong there is I built the wrong team. I put the players I had who are not hospitality players on a project they weren't equipped for, and the team fell apart. So I now pretty much, my wife and I, run the entire resort, and we hate it. It was a good purchase, but it was the wrong purchase. That was the biggest mistake that I think we made in our business.