In one of my worst investor meetings, I was kept waiting for hours by an investor known for making founders wait, which set a negative tone for the meeting.

In a meeting with a famous VC, the investor wasted time asking about my co-founder’s Chinese language skills instead of focusing on our business pitch, which felt inappropriate and frustrating.

I missed out on investing in Dropbox because I canceled a meeting with Drew, which was poor investor behavior and cost me a significant opportunity.

A strong 'no' from an investor is rare; often, you'll receive vague encouragement that doesn't translate into actual investment.

The worst investor meeting can leave you feeling like you no longer want to pursue your business.

If investors are dictating actions to a founder, it indicates a deeper problem within the company structure that needs to be addressed.

After a disappointing experience trying to help a theater producer raise money, I understood that the people who wanted to bring projects to life often lacked the power to do so, relying instead on gatekeepers and investors.

During investor meetings, we faced challenges, including one investor leaving mid-pitch, which highlighted our lack of readiness.

I pitched 75 investors for funding, but we faced rejection after rejection, which made me cynical about fundraising, especially during a time when no one was investing in consumer-driven businesses.