My Pops never saw me on TV or heard me on the radio. Which kills me. I was never the last thing he watched before bed, or the first thing he listened to in the morning, but, even back then, he knew I worked hard. Too hard, most days. Years before he died, Dad could already tell I was letting life get away from me. “Don’t forget to pump the brakes,” he’d tell me. “Work is work. It’s the thing we all gotta do, but it can’t be your everything. It doesn’t mean you can’t do a good job, but it can’t be the thing you love or hate the most in life. That’s what your friends and family are for.”
I don’t remember my dad ever once coming home and complaining about work. I’m not saying the job or the people didn’t ever drive him nuts, but he never wore it home. He was never emotional about work, he was efficient, dependable, and always on-time. He didn’t love it, but he was damn good at it. “You can work your entire life for a company, every goddamn day,” he’d say, “then on a routine checkup your doctor will tell you, ‘Sorry, Mr. Weston, you’ve got an ass full of cancer.’ Then what? That job you just killed yourself for is going to seem pretty insignificant. And what have you been doing this whole time? For what? For who? Don’t forget to pump the brakes. Your job shouldn’t be the thing you look most forward to in your day. Save your best for the people who matter the most. They could pay you all the money in the world, but none of it’ll mean squat.”
I’d like to say that I took my dad’s advice, but I so obviously didn’t. I mean, the part about not getting emotional or letting my identity get too tied up in the job came easy. I’ve spent most of my adult life doing what a lot of people would consider dream jobs—playing on TV, hanging with celebrities, travelling the world. But I’ve never used those two words, “dream job,” to describe what I do. I’ve never said I loved any job I’ve had or told anyone this was something I’ve wanted to do ever since I was a kid, like it was some sort of boyhood dream come true. For the most part, I’ve kept work and the people I work with on the outside. I wanted to see how far I could get in the industry without having to buy in to the community. I refused to kiss anyone’s ass, schmooze, or network. I wanted to do this all on my own, with no help, and I became obsessed with success, and not just my own. If I overheard a co-worker talking about how their husband who worked at a bank got a promotion, I’d be infuriated. It would bother me all day. I’d obsess about it. I never felt like a victim, or that anyone was holding me back or was out to get me. I just couldn’t stand the feeling of not doing enough. Like there was someone else out there, at a bank, working harder than me. My jealousy was fuelled by incredible feelings of inadequacy, and it was impossible for me to acknowledge, let alone celebrate, whatever success I had. It was never enough.
For my whole life, I’d felt like I was running on an alternate timeline to everyone else. Although I was the same age as the other kids, I seemed to go through all the big “growing up” bits way before anyone else. But all that was starting to shift by this point, and I began to feel I was being left behind. I was turning thirty and I was working my first on-air job, which is super late in that world. I was no longer the young kid with the big future. Suddenly I was the late bloomer.
This was the early 2000s and the industry was exploding. People who did what I did, playing on TV, were getting incredible opportunities in America. There was a pipeline of talent flowing from Toronto down to the U.S. to work for MTV, VH1, E!, and just about every other cable network that needed a snarky talking head with cool hair. I was all those things too, but I didn’t know the first thing about finding a job in the States, and I refused to ask anyone for advice. I didn’t want anyone to ever know what I wanted in case it never happened. I couldn’t stand the idea of anyone knowing I’d failed.
Seven months after it debuted, the network cancelled Last Call, the bar closed, and I didn’t have to get drunk at work anymore. Most of the production crew and I were moved over to the station’s new entertainment show, called The A-List, which was very much like Access Hollywood only without the access. This was before TMZ, social media, and gossip blogs, and we were doing Perez Hilton–level shit talk before Perez Hilton was even a thing. The show was stacked with talent, and I was doing a ton of celeb interviews. This was another one of those “dream jobs” that made me miserable: my skin would crawl every time I walked into that building. It wasn’t enough. I needed more, I always needed more.
I was pretty sure my new boss hated me, and I was more than sure I didn’t like him either, but we got along in a weird way. Like two people forced to collaborate on a common goal that’s mutually beneficial. Like two divorced parents who’ve vowed to not screw up their kid, so they suck it up and make it work. My boss and I had this thing—this show—in common, and we were both determined to use it as leverage for the next opportunity. I needed him, he needed me, but fuck did we ever not get along. He didn’t know it yet, but he was also my ticket to America.
I spent months researching New York talent agents. Then I paid a video editor who worked on our show a hundred bucks cash to cut together a demo reel for me out of the best of what I had. I remembered someone saying that agents never watched anything past four minutes, and usually decided within the first thirty seconds whether they wanted to work with you or not. My demo reel was three minutes and fifty-eight seconds, and the first thing you saw was me, wearing only a pair of super-small, super-shiny black bikini bottoms, strapped to a bench, getting whipped by North America’s third-best dominatrix. I’m not sure how one becomes a third-best dominatrix, but it was great television. That, by the way, was one of four clips of me doing crazy shit in bikini bottoms that I included on my demo. There was also a clip of me interviewing Paris Hilton, another one with Pauly Shore, and a few seconds in the studio from one of the rare times I’d been allowed to host the show. And not much else. But it was a killer edit, and it moved fast as hell. Was I proud of it? No, not really. But people loved it, and that’s all that mattered.
I sent that package to twelve New York agents. Six got back to me and four of those wanted to set up meetings. I couldn’t afford the flight, so I had to wait for my boss to send me to New York to do interviews for our show. That way I’d be able to piggyback on the work trip and get him to pay for the whole damn thing.
One meeting lasted less than three minutes, one agent didn’t show, another turned me away while I was still sitting in the lobby. I’d been sitting in the waiting area for about ten minutes when he walked out of his office to introduce himself. I stood up and did all the right things.
“Hang here for another five minutes,” he said, while looking me up and down but pretending to check his watch. “I’ll be right with you.” He disappeared back into his office.
Twenty-five minutes later someone else walked out and told me I could leave.
“Do you want me to come back later?” I asked. “I can change my flight no problem.”
“Noooooo, that’s okay,” she told me. Really stretching out that “no” part.
However, the fourth agent loved me and wanted to sign me on the spot. That’s how the agent game works: three will think you’re shit and maybe even tell you to your face all the things wrong with you, then one guy likes you so much they prep the paperwork even before you arrive. This agent, the one who liked me, ran a mid-level shop out of a tiny office on Lexington Avenue and had helped a few Canadians deal with the immigration and visa stuff in the past. He knew what he was doing. He was around my age, had thin hair, and was much shorter than me, but his suit was incredible. Two-button, single-breasted, and custom as hell. I’d never seen that colour blue in my entire life. This dude looked like he loved money. His clothes were beautiful, but his desk was a disaster. He had all the paperwork already out, propped right on top of a huge stack of files and headshots, ready for me when I walked through the door. I signed on the spot.
He talked like a New York agent from the movies. “Loved the stuff with the whipping. The dominatrix stuff.” He beamed. “Really edgy. Really real.” I could tell that he’d only watched the first thirty seconds of my demo, but I didn’t care. “We can make money together,” he said. “We’re going to make some good money together.”
We shook hands and I skipped across town to do the interviews for the show I was currently working for, then hopped on a quick flight back to Toronto. I didn’t say anything to anyone. Not even my family.
Two months later I had my first big-time American TV job offer. In Orlando friggin’ Florida!
“It’s a morning show they’re building—a brand-new show,” my agent told me. “They’re looking for four hosts, and they really like you. No crazy sex stuff, but they liked your interviews.”
You have to believe me when I say that even though it was Orlando, this was just about the most flattering thing anyone had ever said to me. It charged me up. I racked up more confidence on this one phone call than I’d felt in years. This was the validation I was looking for. It was pure, and I did it all on my own.
But Orlando?
“It’s a syndicated show, which means it will be national,” my agent continued.
Okay, go on, I thought. Now we’re talking.
“Syndicated to small and medium markets throughout the States. So, no New York, no L.A., no Chicago or Dallas.…” He went on and on, in detail, about all the cities the show wouldn’t be in. But still, this was America—my way in. I just needed to get there. This is what people do: go down with a job offer, have someone else take care of all the visa and immigration nonsense, crush it, and hunt for the next opportunity. That had been the plan for years. I needed this.
“I’ve dealt with this team before,” my agent said. “They’ve produced a ton of syndication, and they’re really great with moving expenses. People tend to not want to move to Orlando, so they’ll take care of everything, put you up for a few months. And they pay well too.” Before I could even ask, he added, “We can negotiate, but you’re probably looking at something in the two-fifty, two seventy-five range.”
He was so casual about it, like a $275,000 a year offer was normal to him—and it probably was. To me, this was more money than anyone had ever made in the history of my family. I felt I somehow owed it to every single one of them to jump at this. To me, this was all the money in the world. Even if I went down for two, maybe three years, I could live like a king in friggin’ Orlando and still send enough money back home to Rich so he wouldn’t have to carry our mortgage without me. I could even double up on payments and pay that sucker off years before we thought we ever could. This job, and all that money, would kickstart our future in a way I could never have dreamed.
“Think about it,” my agent told me. “We have a little bit of time. Let me know when you can jump on a quick call with them, then we can get you on a flight down to meet them. But they’re really into you, so I think we have some power here.”
This was a shit ton to take in. It took me three days to even get over the shock of it all, and when that happened, when the shock wore off, it took me about one hot minute to decide I wasn’t taking the job. There was no way. I didn’t want to call them, or fly down, or even see how high we could negotiate that number. I didn’t want to know because the number didn’t matter. I wasn’t going.
My agent was pissed. He begged and did that agent manipulation thing they all do, trying to get me to at least talk to the Orlando people, to hear them out, to wait for a formal offer in writing before deciding anything. After all, there was a ton of money on the line here.
“No,” I told him. “No, thank you.”
That was the last time I ever talked to that agent. I never told anyone about the Orlando offer, or how much I turned down. It was like it never happened.
I didn’t want to be alone. I’ve never wanted to be alone. That’s the simple and the from-the-heart truth. That’s why I turned down that kind of payday. How long would it be before I made even one friend down there? I couldn’t come home to an empty house. I’ve never come home to an empty house. I couldn’t work those hours, up at 3 a.m., crazy long days, and work that hard to not have anyone to share it with. I couldn’t do that, any of it.
Rich was my anchor. I still hadn’t processed Pops dying, and I was scared I might crack. What if all the stuff I had stacked came crashing down? What if I needed my brother and he wasn’t there? There was an emptiness in me that for years I filled with self-destruction, self-loathing, and self-harm. But loneliness was what I really feared. I couldn’t be alone.
Not for all the money in the world.