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Why I Angel Invest

Angel Capital Association

I’m sharing my thought process because perhaps it will nudge some of you to angel invest too! I consider myself a furiously curious person, and angel investing is one of the most rewarding ways I’ve experienced to satisfy this curiosity. THE ORIGIN I was the Founder & CEO of InboxDollars from 2000 to 2019.

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What Angel Investing & Florida Condos Have in Common

Both Sides of the Table

And so it happened that between 2000-2008 I was the biggest buzz kill at dinner parties. They have marked-up paper gains propped up by an over excited venture capital market that has validated their investments. Logic tells me the following: It is hard to make money angel investing. I avoided much of this.

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Angel Investors Do Make Money, Data Shows 2.5x Returns Overall

Gust

I began studying angel investing returns about 10 years ago as a result of a problem I couldn’t resolve: The investing world seemed certain that angel investors were rubes. Conventional wisdom dictated that they made reckless investments in very early-stage ventures mostly doomed to fail. and the U.K.,

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Turning the Camera on Chris Dixon

Both Sides of the Table

He and I once took different sides of an debate about whether “VC signaling&# in early-stage deals is a serious problem or not. So it was fun to turn the cameras on him for 45 minutes for a special “NY edition of This Week in VC&# and hearing his views. I’ve also found him to not be dogmatic either.

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Venture Capital Q&A Session

Both Sides of the Table

People assume that I’m biased because I’m a VC and think you should always get the highest valuation possible. The A round was done in February 2000 (end of the bull market) and my B round was done in April 2001 (bear market). But if you do this early (pre VC) then the price points are pretty low. This is wrong.

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What’s the Real Deal with AngelList?

Both Sides of the Table

Still, as a VC I value proprietary dealflow & long term relationships. I know it was over heated when a deal where I wrote one of the first checks on (as an angel, not VC) went out on AngelList. Mostly, I don’t believe that a VC not being on AngelList is “anti entrepreneur&# – it is not.

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What would you do if told to “fail fast?”

Berkonomics

Reduce further expenditures of remaining capital and protect the assets purchased with the original investment. My favorite story of a fast failure was of a technology incubator started in the year 2000 with optimistic money from several angel investors, including me. A personal story of failing fast.