Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

Learning the Process While Paying the Stupid Tax

6 May 2026 · 1 min

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Christian Osgood calls it the "stupid tax": the costs and mistakes you pay the first time you try a new real estate project. His friend Matt Hawkins, an experienced operator, lost massive time and money on a 150-unit prison conversion due to contractor delays and permitting issues. The only way to cut those losses is to learn directly from someone who has already done it.

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No matter where you're at in real estate, you have to pay the stupid tax to get there. Now, what do I mean by that? I'm actually in the basement of one of my good friend Matt Hawkins' house. He has 150 units, no partners. He's been investing for a long time. Tons of experience, tons of renovation. He did a prison conversion. Every contractor went way over time. Almost all of them went way over budget. Permitting took forever. What should have been a 6-month project took multiple years. And it's not because he's not a fantastic operator. In fact, I'm up here to learn from him today. He's one of the best operators I know. But if you haven't done something before, the first time you do it is the dumbest you'll ever be. He's learned a lot. He could do the same project again way better, way faster with a better team. Even when you have a ton of experience, you still pay to not know what you didn't know. The only way to bypass this is to find people who've done the thing that you want to do and learn as much as you can from them as fast as you can. Which is why I'm here in New Hampshire today.