What I Told the Investors Writing Big Checks

I recently raised a lot of money for a new investment. A lot of money. At least it felt like a lot – both to me and the investors.  When dealing with people who are writing checks for large amounts of money, you should let them know what to expect in return. So I thought about trying to set their mind at ease but instead I decided they don’t deserve to feel easy about taking a risk – they deserve to understand the risk as well as possible. In this case the investment seemed low-risk to me, but nobody can predict the future and I don’t want to burn my relationships.

So, at the very moment they were signing their checks, I delivered what may be my best line yet.

I said, “Just so you know, I’m going to go cash your checks. Then I’m going to head to the casino.  I’m going to gamble. And I will lose all your money because I’m a terrible gambler. And if you’re not okay with that then don’t give me your checks.”

After everyone laughed I made sure they understood I was serious. I still got all the checks and something else – the freedom to invest boldly.

The future is brimming with opportunity. Aren’t you excited?

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