How Ben Wilson Quit His Job and Took Over the Podcasting World

Before launching How to Take Over the World, Ben Wilson struggled with a job that drained him and a question that wouldn’t go away: What does it take to achieve greatness?

He nearly failed out of high school, skipped SAT prep to play basketball, and had no grand plan - only a deep desire to stay free, follow his curiosity, and avoid the soul-crushing conformity of traditional paths.

In college, he hustled. He double-majored in political science and economics, ran a scrappy but successful campaign for student body VP, and found that success often comes not from being the smartest, but from knocking on more doors, both literally and figuratively. But after several years across consulting and marketing roles, that spark faded. He was relying on stimulants to focus, sleeping pills to recover, and still couldn’t shake the feeling that he was drifting further from a life that mattered.

Then, one morning in 2018, while reading a biography of Napoleon and listening to a podcast, he felt a visceral, painful energy - what Aristotle once called zelos: the ache of seeing someone like you achieve what you haven’t yet. That moment sparked How to Take Over the World, the podcast that would change his life.

Ben’s journey isn’t about smooth ambition. It’s about false starts, deep sincerity and finding the courage to lower the boats—even when no one’s watching.

Follow:
Wouter - @WouterTeunissen on X
Ben - @BenWilsonTweets on X
HTTOTW - @HTTOTW on X

Timestamps:
(0:39) How growing up with an idyllic childhood affected Ben
(2:29) What are the Two Father-Son relationships of great men?
(5:50) What taking responsibility for yourself really means.
(9:23) Why you should value Engineering hardship
(14:47) Lowering the Boats – Consistently going all-in 
(25:10) Why being only ‘adequate’ can crush your soul
(31:52) “I can’t go on like this” 
(34:59) The Three Types of Work
(39:55) Ambition Porn and Zealous Pain
(46:13) What would Alexander the Great be if he didn't conquer? 
(50:13) Why it's better to flame out than burn out  
(51:49) If you’re willing to to eat sh*t – It’s really easy to do whatever you want
(57:19) What can we learn from Napoleon 
(1:02:35) Ask yourself: Have you failed twice as much as the reasonable person?
(1:07:10) How to Pivot (in life)
(1:13:59) “You don’t get experience with time” y
(1:14:59) Learning from Mr. Beast 
(1:23:27) Self-Awareness 
(1:35:01) How to tell an immersive story 
(1:41:15) The HTTOW Vision