5 of them are now billionaires or have started $billion-dollar companies
Bosses

Dec 2022


I‘ve had 7 bosses in my career, and 5 of them are now billionaires or have started $billion-dollar companies. From my experience, here’s what separates the ~billionaires from the rest.


Common patterns:


- They ask incredible questions. Even if they aren’t experts on a given topic, within minutes they can reveal the root problem/cause/decision. This skill is used for good (ex: satisfying curiosity) and for evil (ex: testing competency).


- They are totally committed to success. Work is an obsession. Everything can be better. You put in B- work? They’ll call you out on it immediately. There is no work-life balance, work and life are integrated. Ex: One CEO once joined a conference call while on a camel trek with his friends on vacation in Egypt.


- They operate at life's extremes ... Jovial and terrifying. Playful and difficult. All the best things about people, and many of the worst things. All have stand-out confidence. Some have paralyzing insecurities.


- They will quickly pinpoint the most important problem to solve. They may not immediately have the solutions, but they have a knack for finding and articulating the most important problems at any level of altitude in the business, and ignoring the noise.


- They default to action. There is zero procrastination, every task is done quickly. Ex: All of them respond to work emails immediately, within minutes.


Surprises:


- None of them have relentless focus. They are systems thinkers, operating across dozens of things at the same time. They can context-switch in a flash.


- None of them are jerks. Unprompted, they would never screw over employees, investors, or customers. They care about creating value. Positive sum thinkers. Optimists. Unless you take the first shot, then (and this is 100% true for all) “the best defense is a good offense”. Beware. I've seen some vengeful acts, but always as a response. They don't pick fights.


- They default to action. There is zero procrastination, every task is done quickly. Ex: All of them respond to work emails immediately, within minutes.


- None of them have a big ego. But all of them are confident in their abilities. There’s a difference.


- None of them are super-geniuses. Some genius-level employees can replace a team of 100+ great employees. They don’t have that level of raw intellect. They are all insanely smart, but not the smartest person in their respective companies. But, and this is super important, they all hire people smarter than themselves.


Doing these things wouldn’t automatically put you on a path to building a $billion+ company. But there are some juicy lessons in these patterns.


Many of these lessons have helped me become more productive, more impactful, and create more luck for myself and the people around me.