Aaron White - Having Courage in Your Convictions

I’m really excited to share this next interview on the Idea Maze with Aaron White.

This was a unique interview in a bunch of different ways.

First, this is my only interview thus far with an entrepreneur who has primarily been a CTO or technical co-founder in the past. We chatted a little about how involved a technical co-founder is in the idea maze as well as the unique pressure of transitioning to the role of a founder/CEO.

Second, Aaron is the first guest I’ve had on the podcast that was previously a VC. We had an interesting discussion around the things that he struggled with in that role, including the ways that it is emotionally different and more draining than being a founder and operator. In particular, you have the negativity of investing, where you spend most of your time focusing on the problems of an idea and saying “no”. There is also the jarring context switching where you go from evaluating an investment to full-press “sell”mode with both the entrepreneur and the other investors in one’s firm. It’s a very different psychological mode compared to business building.

Third, Aaron is my first guest that is diving head-first into the current AI revolution. We cover a lot of topics here given his extreme optimism around AI and the very broad surface area of opportunities that this innovation presents. In particular, we spend some time discussing the insane rate of change, progress, and competition in the space that makes jumping head first invigorating but also quite terrifying. It’s kind of like trying to traverse a maze that is constantly changing and shrouded in a dense fog. Aaron talks about a few metaphors that he uses as core pillars that he is building against, including his encouragement that “apps are people too”.

And finally, woven through the whole conversation is Aaron’s personal journey of learning to have courage in his convictions. He speaks openly about why he lacked some of this courage in the past, how that manifested itself even in situations where he was very right, and how that drives his path forward.

There is a ton of richness to this episode, as well as some amazing sound bites. I hope you take a listen and find tons of value from it. If nothing else, you’ll hear a sound bite that Aaron shared that will haunt me for many years:

“Failure is a great teacher, but she has infinite lessons”

Infinite lessons indeed :) Enjoy!