Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

Entrepreneur's Journey from Basement to Success

5 Apr 2026 · 1 min

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0:49

In this brief clip, Christian Osgood recounts the humble origins of his first venture with partner Cody Davis. They launched their business from a boss’s office basement, filming with an iPhone and a ring light, without any real estate assets. After securing their first contract, they set an ambitious goal to scale to 100 units. Osgood emphasizes the importance of iterating—recognizing early, imperfect work, repeatedly improving, and using that history as proof of long‑term progress. He frames this iterative mindset as the single most valuable lesson for any entrepreneur.

Chapters

When I first started, we did, I had a business partner named Cody Davis and we started in our boss's basement of his office with an iPhone and a little ring light. And that was, and we didn't own any real estate either. It was us talking about how we're going to close this deal. We had just gone under contract. I'm like, we're going to buy this deal and we're going to scale to 100 units. Follow the adventure here. The lighting was terrible. My outfit didn't fit me well. Uh, just two guys in a basement. You have to go through the iterations of, hey, we did the thing and we continued to do the thing. And now you go back and you, you now have the proof of like, hey, they've been doing this for a long time. And you can go all the way back to the beginning, back when we were terrible at it. And it just adds to the proof of like, oh yeah, he didn't used to be good at this. Yeah. And now he is. And you're always getting better. I, I love, I think this is the most important thing that anyone can learn as an entrepreneur.