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.

Investor meetings are a two-way street; both parties should come prepared and professional to foster a productive conversation.

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

I flew to Chicago for a meeting, but none of the partners were there, just associates without check-writing power. I gave a terrible pitch and there was zero interest in investing. You need to have a game plan for meetings, and I was completely unprepared.

Founders should prepare for investor meetings by expecting negative feedback and being ready for tough questions, which helps avoid discouragement.

It's important to prepare for investor meetings by understanding who you're meeting with and what they value, as this can prevent awkward situations.

I conducted monthly investor updates to maintain transparency about our financial health and operational challenges.

Despite early growth, we faced challenges in fundraising, pitching to 150 investors, with most rejecting us due to the perceived unsexiness of our content-focused approach.

I made mistakes in the fundraising process, including not meeting enough investors and assuming a deal was done before it actually was.