The Startup Playbook, 2nd Edition

Chapter 21Your First Investor Meeting

Even having done investor meetings for many years, I (Rajat) still make mistakes. One meeting was particularly painful. Our existing investors had introduced me to an investor whom they felt was quite interested. I setup a conference call as there would be multiple partners on the phone.

When I got on the phone, I proceeded to jump right in and walk through the business. The investors were seemingly engaged and asked a lot of questions that were all over the place, which made for a chaotic meeting. At the end of the meeting, I asked them what they thought, and the answer was, “It would have been a better meeting if you had a presentation deck and we had walked through that.” Sunk.

I didn't do enough homework to know that this investor was more formal and structured in their approach. Further, even if I hadn't done that homework, I should have asked at the beginning of the session whether they wanted me to walk through a presentation or they preferred an informal discussion.

With only a few chances and a small investor community, mistakes like these can torpedo a fundraising process quickly. This investor passed on our opportunity, and likely they will never invest in one of my companies because of this first impression. There are so many amazing opportunities that they see every day, so why would they invest in somebody who didn't have their act together?

This particular example irked my existing investors, as well, who had put their reputation ...