How to Act Like a Billionaire... and Increase Your Shot at Making It Big
I’ve worked for 4 billionaires.
Billionaires are different. They think differently. They invest differently. They act differently.
How? Billionaire Big.
Elon Musk thinks big. Why not go to Mars?
George Soros invests big. Why not take on the Bank of England?
Richard Branson acts big. Why not build an airline from music expertise?
These Billionaires aren’t you and me. Or are they? Could we act like them? Should we act like them?
They embodied “Billionaire Big” before they became rich.
I’ve worked for 4 billionaires:
One was a felon (since pardoned)
One founded a mutual fund company (“lucky” selling at tops)
One founded a hedge fund (voted most likely to die in high school)
One was a crypto pioneer (online poker player who never held a traditional job)
It’s one thing to look at Elon Musk or George Soros, guess how they are, and try to emulate them off the press. Instead, we’ll explore the people I’ve worked with and what traits you can take on to be Billionaire Big, greatly increasing your chances for Real Wealth.
My first job after my MBA at USC was working for the since pardoned felon Michael Milken.
He was the famous (infamous) “junk bond king”. He broke all sorts of securities laws.
Imagine the school bully, selling parts of his lunch. No one wants the yucky parts. So he makes you, the investor, buy the yucky parts with the understanding that this will earn you the opportunity to buy a piece of a Snickers bar the next day. Because everyone is buying the yucky parts for a chance to buy the Snickers, it looks like everything has strong demand. This is how Milken made sure all his debt deals were purchased, good and bad. This practice is illegal but effective.
Why would you want to learn from a criminal?
Venture capital was not developed enough in the 80s for large, bold investments. Milken used his control over the junk bond markets (forcing investors to invest against their will) to ensure the US lead in various technologies. While it was illegal, he had a vision. His force sped up our timeline. And yes, he broke the law.
Top lessons I learned from Junk Bond Billionaire, Mike Milken:
Your reputation is everything - he spent years building it back and got pardoned
Historical perspective will put you in rare company - research the past
Don’t confuse power (regulators) with brains, but respect power.
Keep fresh eyes - be open to changing your view.
After working for Milken, I built a track record managing $1 billion at an insurance company.
This track record won me a job working for my next billionaire, the founder of a mutual fund firm.
He developed a set of 3 investing principles (timeliness, sustainability and positive catalyst) that powered his entire career. People underestimated him as a simple momentum investor, yet he sold at the top and bought at the bottom in multiple industries, time and time again. He gave me starting capital to run my own fund.
Top lessons from a Mutual Fund billionaire:
Simple and easy is a competitive advantage.
Find a strategy that works and do it over and over.
Following the trend will give you 90% of your returns for 10% effort
New environments, new markets, new economies have all been seen before.
After running the #1 fund in the world for the mutual fund billionaire, I worried that with my fund up 495% in 1999, and the index I competed with up 150%, that markets had gone up more than fundamentals. Simply put, the average business in the US (the index) had not had its sales go up 150%, and instead we were seeing slowdowns in many industries, thus the market seemed poised for a pullback.
In November 1999, I joined a hedge fund where we could make money in down markets.
My boss was a reclusive hedge fund founder and billionaire.
He had 3 analysts responsible for the same number of stocks competing firms had 50 analysts handling. He was also voted most likely to be dead by his high school class. He was bold yet could be very cautious. He arrived at a coffee shop to speak with a class I was mentoring and his clothes were so ratty, they mistook him for a homeless man.
Top lessons I learned from a Hedge Fund Billionaire:
Ask open-ended questions. You don’t know what you don’t know.
Don’t get lazy. He still drove around visiting companies personally with me.
When you believe in something, start with a one-third position. Average into positions.
When it goes in the opposite direction you predict, ask better questions, then exit or add another third. Repeat.
I worked for a young billionaire crypto pioneer.
He was a former professional online poker player, paying his way through college and early life via poker earnings. He never held a traditional job. You may again wonder what you could learn from someone with such a different background.
Top lessons I learned from a Crypto Pioneer:
Let others talk first. Listening makes you smart.
Think big, win, and take the winnings to think big again.
While thinking big, always measure your expected return, like poker.
Don’t wait for the laws to catch up, act, AND don’t break the law, work with regulators.
I’m still in disbelief that I’ve had the luck to work for so many brilliant billionaires.
All 4 founded their own companies, which is a great way to build (or destroy) wealth, and there are so many ways we can act Billionaire Big in our own lives to smooth our path to real wealth.
Being Billionaire Big is about the small as well as the big. Half of my lessons from these 4 billionaires are about “smaller” habits of sticking to what works, such as visiting companies or listening well. These smaller habits provide a foundation to act big in a smart way.
Here’s how to be Billionaire Big
Form and keep great habits:
Listening is smart. Ask open-ended questions and let others talk first.
Start with a one-third position, even when you believe in something.
Don’t get lazy. Keep measuring expected returns. Protect your reputation.
Repeat a strategy that works. Do it over and over, and stay open to changing your view.
So you can think and act Billionaire Big:
Think big, win, and take the winnings to think big again.
Follow the trend to get 90% of your returns for 10% of your efforts
Historical Perspective: New environments, markets and economies have been seen before.
Respect regulators’ power. Don’t wait for the laws to catch up, act, AND don’t break the law.
Should we act like billionaires?
Yes! Act Billionaire Big is about setting yourself up for success.
Each day, I ask myself: am I thinking, investing, and acting Billionaire Big?
Are you?