13 Clever Money Lessons My Pain in the Ass Boss Taught Me

This guy was the devil’s uncle and he can teach you a lot.

Tim Denning
Ascent Publication
Published in
8 min readDec 12, 2020


Picture by OzgeCebeci

If the devil had an uncle then this guy would be it.

Despite the obvious leadership lessons he taught me about how not to lead humans, he taught me a lot about money. The moment he became my boss I knew it would be over quickly. Over the short time I spent working for him, I took notes of all the money lessons he imparted on me before I became the dearly departed.

The cleverest money lessons come from financially rich people who are poor in all other areas of life. Money can show you the ugly side of life which you can learn from. Here’s what the devil’s uncle taught me.

Invest in yourself above all else.

That’s why he was an ass. All the money he made from holding various senior leadership roles was invested in meat pies, beer and real estate. Not a dollar was spent on self-education.

He had the self-awareness of a 5 year old. He was emotionally unintelligent. His jokes were uncomfortable. His communication style was that of a little boy playing in a sandpit and wanting to destroy all the other children’s sandcastles.

All he would have had to do was spend some of his money on understanding himself. He had childhood trauma; it was written all over his face. He clearly had lots of romantic relationship issues over the years.

You can’t prevent tragedy, but you can learn to deal with it by investing your money in yourself.

You can be rich in one area of your life and poor in others.

He was rich in the work he did. He found a way to “step over dead bodies” (as he called it) and get financially rich off a corporate fat cat salary.

To his credit he was fairly rich in the family area of his life too and prioritized his wife and children. In the areas of friendship, health, fitness, entertainment and travel, he was incredibly poor.

When you meet a financially wealthy person, take a look at what areas of their life they had to neglect in order to get the money. It’s rare someone is a billionaire and…



Tim Denning
Ascent Publication

Aussie Blogger with 500M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship — timdenning.com/mb