An Espresso Martini Won’t Solve All Your Problems — But Two Might

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I woke up at 5 a.m. a few weeks ago, stressed out of my mind. I couldn’t take it anymore. After selling my company and semi-retiring, I had built the perfect life, and now it was all crumbling down. My business partner was abruptly gone and I was left holding a bag full of problems I didn’t choose. 

Instead of a sedate life of socializing, writing a newsletter, and taking my kids to hockey games, I was suddenly managing over a hundred employees and having to figure out how to stop hemorrhaging cash across four ventures. 

I couldn’t do it.

I decided I was going to burn my life down. I would stop writing. I would close the businesses. Everything would be simpler. 

I got out of bed and said to my wife, “Honey, I’m stressed. But I’ve realized that I’m doing it to myself. All I have to do is shut down all the stuff that’s freaking me out and I’ll have plenty of time for the kids, plenty of time for you, and I’ll really be able to enjoy life. At 5 p.m. today I’m going to put locks on the doors of the restaurants and walk away.”

“Uh, you’re not actually going to do that are you?” she said, eyes wide. 

And in that moment I realized I wasn’t actually going to do that. But knowing that I could do that has made a world of difference. 

As my friend Annie Trevaskis says, it is much easier to bear a burden that we choose than one that is thrust upon us. By mentally shutting down all the stressful projects in my life, I could mentally start many of them back up again and tell myself in the process — I chose this.

This curveball I was thrown had me suddenly operating two cannabis stores, a cocktail bar, and a restaurant. All of them losing money. So what did I do?  

I immediately sold the cannabis stores, turning a substantial paper loss into a substantial cash loss. Cannabis was a terrible business to get into because I did it to make money, not because I had any interest in cannabis. 

I wanted to sell the restaurant, Marked, but my kids love the place and begged me not to sell it without at least trying to make it profitable. I never wanted to own a restaurant, but I have fantasized about owning a nightclub… maybe Marked could become an amazing club with a few modifications and additional investment.

The cocktail lounge, Coffee Oysters Champagne (COC), has always been my baby. I love going there every weekend, but I haven’t been responsible for managing the place. I decided that I might as well refresh the lounge too. 

It’s a lot. 

Thank god, I’m blessed with an understanding wife, amazing staff, and supportive friends. That’s not an accident. Surrounding myself with marvelous people has been my priority for decades, a lesson learned from the years leading up to my bankruptcy, when I didn’t trust many of the people closest to me — much to my detriment.

I’m also not in a hurry. When you surround yourself with greatness, every moment is fun, and the destination becomes much less important.

My biggest stress in the past few years has been angst from losing 20 million dollars in a series of bad investment decisions. Cannabis stores and a restaurant I had no interest in, a stock market I had no expertise in, and a global pandemic I had no control over — each contributed to an overwhelming sense of financial and personal defeat. 

Now here I am contemplating investing more into my restaurants. How dumb can I get? But what I’ve realized is that I shouldn’t look at my recent setbacks as the pattern. The pattern is a jagged series of gains and losses from the very beginning of my career. The falls are part of the rises; they’re not about failing. They are about learning. And the learning leads to the next rise.

I know now what makes a restaurant successful and what makes it a failure. I know better how to select business partners. I know how to cope with stress. I know not to invest in the stock market (other than index funds).

So I’ve re-cast my past decade. I haven’t suddenly forgotten how to be successful. I’ve been learning a whole new set of principles for this stage of my life.

Onward. Upward.

Now, I’m getting better at prioritizing. I’m getting better at saying no, and I’m getting better at deleting emails. 

I have shut down some parts of my life. I’m no longer trying to grow my newsletter or subscriber count. I’m not trying to write regularly. I’m not reading as much. I’m playing fewer video games. 

And oh my god, am I having fun experimenting with new projects at the restaurants. 

At COC, $5 espresso martinis for people starting their nights, because espresso martinis make everything better. An interactive shot experience that only a manager can order for a table. A new and improved speakeasy entrance. More immersive entertainment, more options for guests. 

At Marked, a rebrand from restaurant to supper club. What do we call it? We’re going with an aviation theme. Runway 06, or Manifest? We went with Runway 06, although it hasn’t been publicly announced yet. Oh wait, I guess I just announced it. Better sightlines, a state-of-the-art sound system, a deeper themed experience with flight attendants instead of servers, a hidden first-class lounge, and… lasers. LASERS!

When I’m not stressed out, this is the most excited and active I’ve been in a long time. I’m not thinking about failure now, I’m thinking of ideas. I love being in the restaurants every night, welcoming guests and talking to staff about how to improve the experience.

The days are flying by as I grow and leverage an amazing team to create and execute a new vision for hospitality in Toronto. We’re going to show Miami and Ibiza how it’s done. I’m not thinking small; I’ve never thought small. It’s been a decade coming, I’m finally waking up. I’ve got the power. I’ve got the team.

There is a time to try and a time to fail. There is a time to lick your wounds and remember what you learned. 

There is a time to dream. 

This is the time to soar.

1. Shameless self-promotion alert: I had a good long talk with Ronan Levy on his “Good Long Podcast”.

2. Annie’s excellent post on the nature of problems.

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