Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

#truedialogue

5 Oct 2025 · 1 min

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Christian Osgood bought Robin Hood Village Resort assuming his multifamily rental expertise would transfer to hotels. It didn't. He spent two years struggling with operations before learning that sellers aren't mentors and that hiring someone who knows the business saves years of costly mistakes.

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The biggest mistake that I made when I bought the Robin Hood Village Resort— I did not get a mentor on hospitality. I assumed because we're good at buying hundreds of multifamily rentals, we're able to do this the exact same way, play the same game. When we purchased this, I'm like, okay, well, we're good at business, we're good at real estate, this is business, this is real estate, we're gonna do fantastic. My first 2 years of owning this was unbelievably hard. It was brutal. I had to be on site doing so much of the work myself because I did not know how to run a hotel. If you're going to do any project, work with someone who's already done the thing that you want to do. I made the mistake of assuming 'Well, the seller will show me how to do this.' They're not on your team. They're selling the property. They're trying to get out of the property. Work with people who are masters of the game. Had I just worked with a hospitality person on this first project, if I got them as a mentor, as a partner, however I integrated that, I would have made astronomically more money and so much faster. Any business that you are in, please get a mentor who's done the thing that you want to do. If you want to buy a whole bunch of apartments like I did, go ahead and hit me up, multifamilystrategy.com, or just shoot me a DM on whatever platform you're currently watching this on.