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It’s weird to work with a boss who doesn’t give a f*ck.
Normally a boss wants to micromanage people, kiss a$$, get promoted, etc. They’re often a company man or woman that’d do anything for their employer.
My banking boss when I was 33 was bizarre.
As I got to know him, I realized the way he treated his job came down to the fact he was a millionaire. He didn’t need the job for money, so this changed his behavior. He was seeking something more.
It took me a while to figure out what.
Because he didn’t need cash, he didn’t take cr*p from anyone. And people didn’t mess with him or his team. He also didn’t sit in back-to-back meetings.
This gave him a lot of extra free time. And it made him extremely zen.
We’d often sit in cafes for hours talking about the meaning of life. Or we’d go to a 6-hour lunch with a client/lead. By the end of lunch the client felt so loved and entertained, the deal practically closed itself.
I’ll never forget this millionaire boss. He changed my life. He gave me the skills and mindset to retire at 34.
Here are the bizarre habits I stole from him that can change your life too.
1. Be quiet in most meetings
Meetings are full of big egos. They want to dominate the conversation.
And this is why not much gets done in big companies. Everyone is so busy fighting and trying to get promoted that nobody listens. I’d go to meetings with my millionaire boss and he wouldn’t say a word. He just took notes, observed, and listened.
This gave him a massive edge.
People didn’t know what he was thinking. And being quiet gave him much higher status.
The loudest people in meetings are the most stupid. Being quiet allows you to be underestimated. Be the Buddhist monk. Be zen. It's much higher status and will give you an aura people can't describe.
2. Stop working with low performers
The masses are low performers.
The world needs low performers so they can get underpaid, get taken advantage of, be laid off at the drop of a hat, and to do all the boring work nobody else wants to do.
Every workplace is drowning in unserious people who live for the weekend and are dying to take another holiday.
Don’t hate on it. Low performance is a fact of life. But if you allow yourself to be in this category, you’ll get screwed because of it.
Stay away from low performers. Their pessimism and laziness is like a virus that’ll drag you down and give you herpes.
Spend time around top performers instead. The more entrepreneurial ones.
The ones who see problems as opportunities. The ones who use their creativity and imagination, instead of working in admin mode all day and drowning in distractions and phone notifications that never stop.
3. Cheat on your job with a side hustle
I was a stupidly loyal “company man.”
I did whatever the bank told me to do, even if I knew it was dumb or bad for the customer. This made me a people-pleasing kiss a**. Yuck. This is the default path if you bet your life on a corporation that can lay you off with one email and zero f*cks.
My millionaire boss acted differently.
He had side hustles, side businesses, offline consulting gigs, and even board positions at other companies. He didn’t hide it either.
He knew that the most successful people in business have multiple interests.
He didn’t let non-competes and HR policies stop him from having other income sources. He just made sure he wasn’t doing anything dumb or stealing bank clients.
And even if it all blew up, he knew no company would bother suing him. Too hard. Not worth it. And the burden of proof is too high.
After he told me all this, I felt like I had a spiritual awakening.
All my fears started to go away. I was afraid of a boogeyman that didn’t exist. I asked my lawyer and friend Robbo and he agreed (not legal advice).
So I changed how I thought about work and my income. It led me to make $70K USD a month on the side.
The smartest workers are all building stuff on the side. They understand a job is how you get underpaid. Great way to start. Dumb strategy to embrace for 40 years.
Your customers & network are the bones of your first business. Act that way. Start building a business long before you need it. See a job as a form of modern slavery, and a one-person business or bigger as a way to become self-sufficient.
You’re probably too smart to work in an adult daycare for the next few decades and follow nanny police rules while getting told what to do by people much dumber than you. And I’m willing to bet you hate commuting to an office. Don’t do it.
4. Always be closing
I freaking love this strategy.
My millionaire boss had a weird obsession with the movie Glengarry Glen Ross, starring Alec Baldwin. The famous line “always be closing” became a mantra.
I later adopted it.
The way he explained it to me is I should always tell management about the offers I’m getting from competitors. I should let them know recruiters are reaching out to me on LinkedIn every day. He told me:
“Always ask for more money, better job titles, bigger teams to lead.”
If you don’t ask you don’t get, and then you starve. Being proactive is crucial. Don’t focus on what you’re doing now. Communicate the vision of where you’re heading. Think and act like a high performer long before you become one.
This strategy allows you to psychologically challenge management the same way they do to you with KPIs and the constant threat of layoffs. It’s a two-way street.
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