Why fixing your pitch won't always fix the problem

A couple of months ago, I wrote about how investor "no's" are often unresolved uncertainty rather than outright rejection. I’d like to go one layer deeper and discuss the difference between what feels risky to an investor and what actually is risky about a business. Conflating them, which both founders and investors tend to do, creates a lot of unnecessary damage.

It reminds me of a story my friend Karen told me. Karen is a multi-exited founder who has raised over $100 million and is now a prolific angel investor. She told me how early in her career, she walked into a room of primarily white men between 45 and 70 years old to pitch her company. No other women were present.

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