I Spent $100,000 to See My Favourite DJ in Las Vegas

“So what’s the worst thing a celebrity has ever done on here?” I asked Barbara, our flight attendant, just after taking off.

It was a year after I sold Audiobooks.com to a private equity fund and my second private jet trip, taking 10 of my closest friends to Las Vegas for three days to see Zedd at Omnia.

Barbara, who was about 60 years old and not taking any nonsense, answered my question about how to be a baller, “Don’t pee on the furniture. And hide anything else you don’t want me to see when I’m serving.”

Barbara was ancient and took so long walking back and forth from the front of the plane we had plenty of time to hide any contraband. I also carefully told everyone where the bathroom was, no sense taking chances.

After I came into liquidity at a large level, I started to VIP everything. I became the king of bribing my way to the front of any line. “Whose hand do I have to shake?” became my mantra.

On my first private jet to Miami after selling my company, I bought the fruit plate and snacks option, which cost $1000. For a fruit plate and snacks. It occurred to me that maybe I was being taken advantage of.

To sort of quote Steve Martin from The Jerk after he lost all the money he made, “I bought a fur lined sink, but I bought some stupid stuff too.” You and me both, Steve.

I got smarter for the flight to Las Vegas, and my wife sweetly volunteered to pick up some gourmet platters from the grocery store for the flight. Then my friends razzed me for not paying $1000 for Wi-Fi on the plane. For fucks sake, it’s a private jet, talk to each other.

But $1000 on Wi-Fi or a fruit platter isn’t really a problem. What is a problem is that the skills required to keep money aren’t the same as the skills required to make the money in the first place. In fact, the risk-taking brand-building behavior that builds fortunes is often exactly the wrong type of decision framework once you have a lot to lose.

So after I sold my company and got more money than I could reasonably spend (believe me, I tried) I found myself making reckless investment decisions that made my reckless spending pale in comparison.

The problem with spending $100k to see a DJ is that it normalizes even worse behaviour.

• Opening a bar in downtown Toronto. I mean, what guy who sells his company doesn’t want to own a bar?

• Opening up six cannabis stores in the middle of COVID. You can’t lose money on cannabis! Wait, you can?

• I can get in to a pre-IPO deal for a sure thing? Wait, let me give you all my money!

I’ve written before that if you invest in things you believe in, if it doesn’t work out financially, at least you did something you loved. The bar, Coffee Oysters Champagne, is one of the best things I’ve ever done, despite costing a couple million. Stupid COVID. I still might make it back some day. Come visit. Buy an expensive bottle of Champagne. Thank you.

Cannabis I didn’t believe in. Won a lottery, got in bed with a bad business partner, lawsuit, counter-suit, wow what happened to all the money? A couple million here, a couple million there, it starts to add up.

I suppose I’ve been lucky. The bad decisions have cost me, but haven’t cost me enough to affect my financial independence. I’ve become a lot more careful in the past two years as I’ve held my breath and waited for the economy to turn around. Pro tip: I’m going to be holding my breath for a while.

With my very first business, Videodrive, I lost $10,000 of my own money along with $90,000 of other peoples’ money, largely on the back of my own hubris, thinking I could succeed in creating a home video delivery business when seven prior entrepreneurs had failed. I told my entrepreneurship professor at Cornell that I would succeed because “I’m smarter than those guys.”

When I related the story to a friend of mine who was a successful entrepreneur, he said, “$10,000 is cheap if it taught you some humility.” Yep, it sure would have been.

And now, 20 years later, I’ve learned a series of more important, more expensive lessons, this time about how to keep the money I already have.

1. The stock market is a casino (except index funds).

2. Invest in things you believe in.

3. Don’t borrow money to make high risk investments.

Big money isn’t lost on spending. It’s lost on investments that go the opposite direction of what you expect.

So buy cool shit if you’re lucky enough to be able to afford it. The $100k to see Zedd was totally worth it. But next time I won’t pay $5000 to have a woman descend from the ceiling on a metal wire to deliver a bottle of champagne. Some things are just unreasonable.

1. COC, my awesome speakeasy bar in downtown Toronto

2. My story about losing $5 million in the stock market on one deal

3. Zedd at Ultra Music Festival in 2023. My man.