Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

My Opening Question to Raising Capital

23 Jul 2026 · 1 min

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In this brief monologue, Christian Osgood explains his standard opening question when raising capital: he asks potential investors to describe in their own words what a successful investment looks like for them. By uncovering the investor’s desired outcome, Osgood can quickly determine whether his current deal aligns with that vision. If the deal matches, the pitch becomes a simple demonstration of fit; if not, he politely declines to present the deal, positioning himself as ethical and trustworthy. He notes that this approach not only streamlines the pitching process but also builds goodwill, leading investors to consider future deals because they trust he won’t waste their time with unsuitable opportunities.

Chapters

My opening question every single time I raise capital: tell me in your own words what a successful investment for you is. What outcome would you like to see in a deal? And if they tell me anything other than what my deal does, I really kindly tell them, hey, I do deals that are like that. This is not that deal. I don't want to show you a deal that I don't think is going to hit your goal. If they share something that the deal does, your pitch is so easy because now you're— all you're doing is you're simply showing them this is what you wanted and this is why the deal does it and how the deal does it. It is the easiest pitch to close. I think it's the most ethical way to close too. Like the discovery question is What do you want this to look like? If it looks like this, I'm going to tell you why I think it's a good fit. If it doesn't look like that, I'm going to politely say no. And what happens is those people usually invest in the next deal because they know that you're not going to put them in a deal that's not a good fit.