Want some business advice from a billionaire? Well, hands down the best work (and life) advice I ever received indeed came in the form of a riddle from one.  

I’m passionate about stalking billionaires. I want to learn everything I can from the most successful people.

That’s why I went to work for one of the biggest billionaires on the planet.

Back in 2016, I talked my way into a fancy venture capital job in Beverly Hills working for one of the most notorious billionaires on the planet. This person is known for creating a company in the 1990s that went from zero to a staggering $50 billion in value in less than three years.

Who better to teach me the secrets of the universe?

And initially, I loved it. I felt important. Immediately, I started working on new deals, confident I would find a new investment for the firm that would make me millions within weeks. This was my ticket to finally becoming a whale.

Yet, only a few months into the job, the billionaire called me into the boardroom. This monster boardroom was straight out of the movie “Wall Street”. The furniture and artwork dripped with money.

The billionaire sat at the head of the table and said, “I like you, Ben. Do you want my real advice? Do you want me to teach you how to change your life?”

No joke. Pinch me. I thought “holy cow, this is my moment!”

The billionaire smiled a sharky, toothy smile and said, “Ben, the secret is you need to start owning things. Stop taking pieces. You will never get ahead taking pieces of other people’s business. The game is played by learning how to own.”

On first blush, of course this made sense. Yet it didn’t seem like some grand piece of wisdom. “Own stuff”, I chuckled. I can do that. I didn’t really understand what the billionaire meant quite yet.

And the billionaire could tell. So he went deeper:

“Ben, you see, everything is designed for the ownership class. When you’re playing for a piece, a commission, a fee, or a percentage of a deal, you don’t get rich. You don’t participate in business multipliers, like when businesses you own get sold. Instead, what you are mostly doing is feeding your own ego. You are trying to feel important. And you try to look busy, and look like you know people. It’s owning that is actually about winning. ‘Owning’ doesn't care about what it looks like. Quit striving to be a mover and shaker, and start being an owner.”

I nodded my head. And I offered my genuine thanks for his wisdom. I wish I could say it changed me that very moment. But it didn’t. The advice was like a strange buddhist koan to me. I sat there confused with his words for months. But I took his advice to heart. Whenever I had a free moment, whether I was taking a run or hitting the shower, I would ponder the billionaire’s advice.

And then a few months later, on the drive into work one morning, it hit me like a load of bricks.

I got it.

That morning, scared as hell, I walked into the billionaire’s giant office. The billionaire had photos of himself playing golf with presidents. He had photos of himself with world leaders and titans of industry. There was literally gold dripping from the walls. And there he sat grinning like The Cheshire Cat behind his massive desk.

Somewhere within that smile, I saw that he already knew my next words.

I said, “I quit.”

I suspect the billionaire knew that I had solved the riddle. In order to succeed, I no longer wanted to be owned. I wanted to now start owning.

Fast forward a few years, and in my view today this advice has allowed me to live and succeed differently than all of these other young tech startup guys and “wanna-be” investors. If working smarter and owning things meant I might go from 0 to $50 billion in 3 years, then it was time for me to drop what everybody else was doing and start to work in a smarter and healthier way.

I quickly started saying no to:

And what did I immediately start saying say yes to?

Based on the billionaire’s advice, I created a 3-pronged approach to my “game”:


The billionaire’s advice helped me see I needed to build my own venture. I quietly started my own S-corp consulting business based on the the idea I can help startups and entrepreneurs become smarter dealmakers. It was long past time that I started to profitably teach others the same rainmaking lessons I had learned along the way.

Within a few short months, my consulting business took off. Instead of trying to take small stakes in startups, I now charge them for my services. This means I’m multiplying the value of my own company every single day. And now that I have focus and clarity, I also now have more customers than I can handle. To this day, my firm has a waiting list of potential clients who are also sick of doing things the old way. They are sick of building businesses that are more concerned with validation and social proof, than results. I’m now helping entrepreneurs better live the advice given to me.  

Info and physical products

With the profits from my consulting business, I recently started to find new ways to serve my customers. While personal consulting is a great product, it’s generally too expensive for many young startups that need our help. So the way we can help more business people at scale is through info and physical products. I can provide nearly the same value as consulting at a much smaller cost.

Software products

The final frontier is software. Software has magical attributes. It scales. (And creates recurring revenue.) So I now have profits from the consulting and info/physical products pouring into developing new software applications. In fact, in 2017, my firm has partnered with another leading Los Angeles Venture Fund in a JV to develop cutting edge gaming software. This time around I own the majority stake in the venture. That’s right!  I went from owning fractions of companies to now owning majority stakes.

Am I perfect? Definitely not. I still find myself playing for commissions sometimes. If I’m not deliberate with my actions, I’ll start to get FOMO with cool Silicon Valley trends of the moment, and focus too much of my time and energy on looking smart and cool. Trying to look smart is a disease. I really try my best to remember it’s not how the game is actually played.

I owe this billionaire a huge round of thanks for teaching me how to get out of the commission game. He was generous enough to help me figure it out on my own. When I started playing the right game, it allowed me to start asking for more in life and business, and it changed my life.  

If you have a particularly great story or a big “owning” victory, hit me up at [email protected] or @benjaminsmith and let me know. I’d love to share your stories with the Capitalism.com audience.

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