4 Great Reasons To Be Rich (With Caveats)

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I first heard the concept of F-you money when I was a 30-year-old salesman. My boss told me it meant I could say “fuck you” if he told me to do something I didn’t want to do. And because I didn’t have F-you money, I had to do what he told me.

I hated that guy.

I had a problem getting along with bosses in general, and I was fired a bunch of times en route to finally selling audiobooks.com for what I would call “Fuck you and the horse you rode in on” money. I didn’t start the company to get rich. I started it because I couldn’t hold down a regular job.

When I finally got my ticket to ride away from asshole bosses forever, I discovered there were many more pleasures involved in becoming rich. Here are four of my favourites, with caveats.

1. Never being turned away from an event

I’ve learned to walk up to bouncers at a club and ask, “Whose hand do I have to shake?” so I can bribe the right person for a good table. It’s made me lazy. I rarely book things in advance because I like to keep my schedule flexible.

Paying $1000 a ticket so I can bang on the glass and yell, “You rock, Matthews!” at a Toronto Maple Leafs hockey game? Worth it.

Caveat: Your friends may not be able to afford what you can afford and it’s no fun attending sporting events alone. I have resorted sometimes to telling a friend that I got a special deal on tickets, so they don’t feel bad that we got seats in sneezing range of the player bench.

2. Having a personal assistant

Well before I came into money, I had a mentor who invited me to lunch at his country club. I was in awe at the polished mahogany and ever-present service staff. I asked him what advice he had for me if I ever got rich, and he said, “Get a personal assistant and pay them well. It will improve your life more than any other thing you do.”

When I had even an inkling of profit coming in from my audiobook business, I leapt at the opportunity to hire an assistant. My mentor was right, it improved my life immensely. And when the first child of my second marriage arrived, I convinced my reluctant wife to hire a nanny — a personal assistant for her. It may have saved our marriage.

Caveat: An assistant is a professional, not your personal slave. My wife and I weren’t always reasonable, and we had to learn how to manage our assistants. Our current right-hand people have been with us for the better part of a decade, and it’s not an accident. Apologies to the earlier staff that we learned from.

3. Being able to help your friends

I invest in many businesses, usually because I want to make money, but sometimes just because a friend is doing something worthwhile. I don’t have an expectation of a return, and I rarely get one, so it all works out.

Caveat: everyone wants to be my friend. The stream of people asking me to give them money or invest in their businesses is never-ending. Do they think I keep money sitting in a big jar in my foyer? For the twenty people a day who send me “investment opportunities” on social media — I’m not your friend!

4. Owning a bar

A place where everybody knows my name. But sometimes they don’t know my wife’s name, that’s always fun.

I appreciate it when a new bouncer, who I’ve never met, does his job stopping me at the entrance and asking me to wait in line with everyone else. My wife, though, has a “Don’t you know who I am?” kind of reaction.

I don’t know why I find it funny when she gets stopped at the door. Probably because then I get to feel like a hero when I shake the bouncer’s hand and say, “Hi, I’m Sanjay, the owner.” It’s as if, for a moment, I’m Bruce Wayne, whispering, “I’m Batman.”

Caveat: it’s amazing how many people think they know how to run a bar or mix a drink.

Them: “Your espresso martinis aren’t quite balanced.”

Me: “That’s funny because that’s the third one you’ve had tonight.”

There are lots of other great things about having money. A nice house and car. Flying first class. Unlimited massages.

But I also miss the simple pleasure of wanting something and having to sacrifice to get it. When I bought my first expensive ($700) Boss winter coat, it took me two weeks and four trips to the mall before I could convince myself that it was worth it. Finally, my wife got frustrated and said, “Just buy the damn thing or stop thinking about it!”

Having money means I can buy things, but I also worry all the time about people taking advantage of me, and about the astonishingly bad business investments I’ve made more recently.

The fear of having it all taken away from me has been palpable and constant (and sadly, sometimes justified).

My state of mind has improved through therapy and meditation, not with the acquisition of dollars.

Everyone can have some version of the perks I’ve mentioned, and I’ve realized over the years that the F-you approach to decision-making comes from a mindset, not from a monetary threshold.

Plan ahead a little to get good seats at a restaurant or event. Hire someone to do the things you really don’t like doing — virtual assistants and Fiverr are modern miracles.

Bang on the glass and yell, “You rock!” at your kids’ hockey games, and make sure the staff at your local pub know your name. Act like you own the place, they love regulars.

The best things in my life now that I have money? A sunny day. A breath of fresh air. The opening notes of my favourite song. And most of all, the friends and family that I already had.

Make money, there’s nothing wrong with that, but remember that real wealth comes from being a person rich in imagination and character.

Nobody can take that away from you.

1. One of those astonishingly bad business decisions

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