3min chapter

My First Million cover image

Rapid Fire Business Ideas, How to Buy a Public Company, and Mastering Your LinkedIn Profile

My First Million

CHAPTER

Startup Investing - What's the Biggest Investment Miss?

I think competing for deals sucks. I find it very demeaning, trying to convince somebody to let me invest $50,000 in their round. The other thing that's happened is trying to turn $50k investments into $2 million over a 10 year period doesn't really do anything for me anymore. My first startup investment ever was a 100k investment, a company called Chart Boost in 2011 or 2012. And then the company sold in 2021 and I made $2 million. That was a 10 year time span. So I think having to wait 10 years to get cash out is really annoying and makes me like it a lot less. High valuations have also gone really crazy.

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