You might have heard: Amazon’s co-founder and chief executive Jeff Bezos is leaving the building. He is handing the company’s reins to Andy Jassy, the current head of the fast-growing and very profitable Amazon Web Services. Even though I already wrote about the Amazonian Transition, at the nudging of a friend, I decided to look at Bezos’ decision using Bezos’ fabled “regret minimization framework.” Regret Minimization Framework is a simple question: Will you regret not doing this in X number of years?

A very long time ago, Bezos said, “I knew that when I was 80, I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed, I wouldn’t regret that. But I knew the one thing I might regret is not ever having tried.”

Using the RMF, leaving now makes perfect sense. Those who have worked with Bezos say that, for him, time is the most valuable commodity. Amazon is not the right way for him to spend that time. Here are some reasons:

  1. In the wake of the COVID-19 crisis, Amazon is at a high point. It surpassed quarterly sales of $100-billion. Can this fantastic year be surpassed, especially with looming regulatory challenges and growing mistrust in all quarters (not only of Amazon but of all Big Tech)? 
  2. The general attitude towards Amazon and technology behemoths is going to force these giants to play defense. Bezos is better at playing offense. Just look at the history of the company. As I wrote in my piece, Jassy is a more erudite and pugnacious executive to helm Amazon during the next phase of the company. 
  3. Automation and the continuous encroachment of technology into average lives are givens. And so is the increased intensity of confrontations with politicians, regulators, and other civic-bodies a non-stop barrage.
  4. Blue Origin started two years before SpaceX, only to be overtaken by Elon Musk’s crew. Bezos is a hyper-competitive individual in everything, so this must not sit well with him. He name-checked Blue Origin in an email to employees, so don’t be surprised to see him spend significant time at the rocket ship company. And why now? Space technology is having a moment — just like the Internet did in the mid-aughts. 

“Bezos’s decision to step down also reflects an uncomfortable reality for one of the wealthiest people in the world: The walls of his highly compartmentalized empire have been crumbling for some time,” Brad Stone, the author of a book on Amazon, and soon to be published a follow-up on Jeff Bezos, writes in a must-read insightful analysis.