“Self-deprecating humor is really only funny to the people comfortable deprecating you and uncomfortable to everyone else” – Red (Overly Sarcastic Productions)

Very recently I was asking to give a pitch on my company. I gave a rundown of my background in biomedical engineering, to running Trulioo’s Fraud/ML product line and started an AI company. Everytime I give this background, I kind of feel like I’m telling a bunch of business people that I’m better than them, so I throw in a dig at past me. I feel it gets a chuckle, makes me seem less pretentious and more grounded.

Only this time, towards the end of the pitch, this investor called me out on it. He said:

Don’t tell people you’re bad at something. Why would I want to invest in someone who wasn’t the best”

It was a startling realization that I’ve now moved from a environment of stability to an environment of extreme competition. I’m competing with organizations that have millions in their pocket and I need to make sure that I can compete.

When I was in University, I was incredibly egotistical. After working on myself I started to be a lot more approachable and friendlier. I think that was a mistake. I have to be my biggest advocate again.