Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

The Cost of Partnership Mistakes

12 Apr 2026 · 0 min

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0:29

In this brief YouTube conversation, Christian Osgood reflects on the financial impact of mistakes made within his partnership with a colleague (referred to as Cody). He acknowledges that while they have generated millions together, the cumulative cost of their errors is substantial, ranging from five to eight figures. Specific examples include an opportunity cost exceeding $2 million from a missed Robinhood deal, five‑figure legal settlements and fees, and six‑figure earnest money that was tied up for years. Osgood emphasizes that despite these costly missteps, the overall value of their joint successes far outweighs the losses.

Cody and I have a very successful partnership. I think we have gotten ourselves or each other into trouble nearly as often as we've had a victory. However, fortunately, the value of the victory has massively outshined the exorbitant cost of mistakes. If you had to put a dollar figure on it roughly, and we'll just say number of figures, 5, 6, 7, or 8 figures, how much do you think that we have cost each other by making mistakes along the way to the— for context, we've made millions of dollars together. How much do you think the two of us have cost each other?
Well, the opportunity cost of just Robinhood alone was north of $2 million for me from the actual loss of capital. Yes. Had that money been placed into multifamily that we could have pursued otherwise that we didn't. Yeah. I mean, just that deal was a couple million dollars.
So there we go. That puts us into the sevens already. And then we've had, had five-figure lawsuits that we didn't need to be in that we were able to settle, but still cost, you know, low five figures of legal fees, low five figures of settlement fees. Had six-figure earnest money tied up for years. It's— that would have been so helpful.
I remember us sitting down, it's like, if we just had that money, we would not have any problems right now.