Betting My Music Journalism Career on a Poker Tournament

For much of my 20s I was obsessed with music festivals.

Like any collectors item I wanted to experience them all, and even enjoyed duplicates of some of my favorites. Since my first music festival in 2011 I’ve attended Bonnaroo in Tennessee, Coachella in California, the New Orleans Jazz Festival (obviously in New Orleans) on two separate occasions, Montreal’s Osheaga three times and New York’s Governor’s Ball twice, but the one I want to tell you about today is a little-known festival called Life is Beautiful, held in downtown Las Vegas.

The first time I attended the event with two friends I was blown away by how the event pushed the boundaries of what a musical festival could be. The second time I attended the event it was one of the best weekends of my life, despite significantly crippling my music-writing career. It would have been much worse, however, if not for a poker tournament and a Dave Grohl guitar solo I will remember the rest of my life.

I first heard about LIB (which is what the cool kids call it) the winter before the inaugural event in 2013. Though it didn’t have the same prestige to the festival-going community as Coachella or Bonnaroo there were a few elements that made it irresistible:

1) It was being held in the empty lots of old downtown Las Vegas as part of a revitalization project

2) It had a pretty incredible line-up for an event of its size

3) The food was supplied by some of the top chefs on the Vegas Strip, who weren’t allowed to charge more than $10 for any dish (no matter their cost a few blocks over)

4) It was being produced in partnership with Cirque du Soleil, whose acrobats and performers joined musicians on stage for surprise collaborations

5) It was in Las Vegas, and what 20-something doesn’t like an excuse to head to Vegas with a couple friends for a weekend?

Despite my passion for music and my career as a freelance journalist I had never covered a music festival before in any official capacity. At the time contributing to Rolling Stone was still a pipe dream, as was interviewing a genuine rock star, but I had started doing some freelance music coverage for a little-known publication out of Chicago called Consequence of Sound. In spite of a rather painful falling out with the publication’s founders I’m still an avid reader, and strongly recommend the website to any music (and now film and TV) lover, especially those based in and around Chicago.

I first reached out to the publication to do a “music festival survival column,” and later pitched them on an interview with the founder of Life is Beautiful, a man named Rehan Choudhry. I spoke to Rehan just a few months before the event’s second iteration, and as he spoke about the headliners (including Lionel Richie, Kanye West and the Foo Fighters) about this year’s food lineup and the Cirque du Soleil Beatles tribute, I knew I had to find a way to attend. The fact that I couldn’t afford to go, and that none of my friends could either, wasn’t going to deter me.

Beatles Tribute — Life is Beautiful, Las Vegas, 2014

I pitched Consequence of Sound on the idea of covering the festival, and they agreed, though they only offered me a total of $200 to write 500-word blurbs on about a dozen artists. To put that into perspective, I’d normally expect closer to $1 or at least $.50 per word, putting the assignment’s true value somewhere between $3,000 and $6,000.

There were also other red flags that I was too excited to acknowledge at the time, including the fact that they wanted me to cover multiple shows that were scheduled to take place at the same time, and the fact that they wanted me to write a total of about 6,000 words in one weekend while also attending the festival. Half a decade later I’d still consider that an impossible task, even with an otherwise empty schedule for the weekend.

Still, they were the only music publication willing to give this inexperienced freelancer a shot at covering an entire festival on his own, and their letter of assignment was all I needed to get a free media pass to the event, which itself saved me $350 on admission. Despite having to pay for my own flight and hotel I didn’t consider the assignment a loss; someone was paying me (even just a little bit) to cover a music festival. That in and of itself was a dream come true.

In hindsight, I was at best naïve and at worst a little stupid for not even entertaining the idea that it might be a complete disaster.

The first sign of trouble was when I arrived in Las Vegas straight from a major tech conference in San Francisco and checked into the hotel, only to discover that I only had enough funds to pay for the first of my four night stay. I had plenty of cash in my account ready for the trip, but failed to anticipate the high cost of living in San Francisco.

I paid for the first night at the Paris hotel in Las Vegas and was told that they could hold my reservation until the next morning, at which point I’d have to either come up with the remaining $600 or vacate the hotel. With the festival kicking off the next morning I couldn’t afford to spend any time switching hotels the next day, assuming I could even find somewhere to stay on my remaining budget of about $50 a night (less if I wanted to eat that weekend).

It was like a ‘90s sitcom plotline come to life: I had one night in Las Vegas to come up with the money, or I’d never realize my dream of covering a music festival as a professional journalist

I only had about $65 cash on me, so I did what I felt was the most logical solution at the time; I entered a poker tournament with an entry fee of exactly $65.

There were about 35 competitors in the tournament, each trying to place in 4th or better to get a share of the prize money. For me, however, fourth wouldn’t have been enough for another night at the hotel, and second or third would only buy me one more night. I had to go for broke.

After the first hour of the tournament I was down to the last of my chips, but a few lucky cards and a few unwise moves by my competitors turned things around for me. After the second hour we were down to only a dozen or so players, and I had the most chips by far.

One by one the remaining players were taken out until it was down to just myself and two others, duking it out for the top prizes. By the start of the fourth hour we were down to two, and I had a commanding lead. It didn’t take long for my chip pile to swallow theirs, and four hours later I was crowned the champion.  

Poker tournament payout sheet, Las Vegas, 2014

I remember literally shaking in disbelief as I approached the counter where I received my prize: $758 in cash, minus a generous tip for the dealers. I took my winnings and ran as fast as I could to the hotel lobby, where I paid for the next two nights in crisp hundred dollar bills.

I had a Muhammad Ali-sized ego as I arrived at the festival the next morning, high off a series of unlikely victories, sporting my purple and green “media” wristband (see obnoxious selfie below). Despite the enormity of the professional challenge ahead of me I felt like I could accomplish anything, even afford to have a few drinks as I ran from stage to stage with my little red notepad jotting down a few lines about each performance as I went.

Obnoxious selfie with media wristband. Life is Beautiful, Las Vegas 2013
Obnoxious selfie with media wristband at Life is Beautiful, 2014

After each day of the festival I’d return to my hotel room and punch out as many words as I could about each of the artists I had seen, but could barely get through my daily quota of 2000 before nodding off and doing it all over again.

When I recall the festival now, five years later, only two things really stand out; running between stages to catch enough of each show to jot down a few notes, and Dave Grohl. After bolting to the headlining stage on the third and final night of the festival midway through the Foo Fighters performance I found myself so far back into the crowd I could barely see the legendary frontman, but fortunately he was kind enough to come to me. I didn’t even notice the pathway that split the crowd into two until he ran through it and stopped about 5-feet away from where I was standing, and busted out an extended solo (see pic below) .

Dave Grohl, Life is Beautiful, 2014

I thought there was no way COS could expect me to submit this giant report the day after the festival ended, but I was wrong. At the airport the next day, still a few thousand words short, I asked the editor in chief when he needed to see a draft to which he responded “this afternoon.” I asked if he could wait until I landed 5-hours later, and he reluctantly accepted, not that he had much of a choice.

I was exhausted from a marathon week on the west coast as I wrote the remainder of my reviews on the airplane. I know the draft I submitted was sub-par, but I felt it was still usable. Evidently the editor in chief felt differently.

“Okay. Well, I’m only paying $100 for the coverage,” he wrote in an email the next day. “I rewrote entire sections and there were typos galore. I spent two hours on it this morning.”

I responded with an apology and an explanation, and thanked him again for the assignment. I offered to help in any way that I could, and swore it would never happen again, but it was too late. Consequence of Sound sent me $100, and has never responded to my emails since.

Girl Talk performing at Life is Beautiful, Las Vegas 2014

That was the end of my music-writing career, at least for the time being. After that I refocused on my careers and future-of-work reporting, that story next. In all my years freelancing I’ve never submitted work so bad that a client refused to pay me my full fee, and I probably would have been more upset about the whole situation if I hadn’t just won a few hundred in a poker tournament, and gotten 5-feet from a Dave Grohl guitar solo in Las Vegas, all without having to buy my own wristband.

Five years later, I still look back on it as both one of the best and worst weekends of my career.

On Taking the Leap Into Freelancing

I’ve done a lot of scary, crazy and bold things in my now 7-year career as a freelance journalist, but none more so than kicking off the career itself.

I tested the waters as a freelance journalist on a part-time basis in the late autumn of 2012, and took the full plunge early in the New Year. Studies show that most choose self-employment out of a disdain for their boss/job, for more control over their careers or to make more money, and I guess my reasons were a combination of all three. At the same time I’ve always been very independent, so much so that when the concept of freelancing was first introduced to me it felt like an inevitability.

In fact, when my journalism professor first introduced us to the concept of freelancing (shout out to Professor Mark Kearney) he didn’t sugarcoat it one bit: he told us that finding work was a full time job unto itself, that freelance rates haven’t budged for the better part of the last half century and all the challenges associated with fluctuating income.

It sounded terrible, but inevitable. I knew myself well enough to know that it was only a matter of time before I went down the path of self-employment, though I wouldn’t have guessed that time was just two and a half years after graduation.

It didn’t help that I spent the first 8 months of those post-graduation days helplessly unemployed with absolutely no prospects, or that the first gig I did land was for a “digital content” studio that only dabbled in what I would call traditional journalism. That constant strive towards independence had also compelled me to move out of my parents house and into a tiny downtown condo, long before I could afford to do so.

Through my first year of formal employment my boss “started me off” with a pretty low salary but promised a significant raise for year two, approximately 30% more than what I had made in year one. I spent a year on the fence about that job, often thinking about jumping ship, but the promise of a higher salary gave me just enough motivation to soldier on. Of course when the longest year of my life finally did come to an end, the raise that was offered to me was closer to 5% accompanies by the promise of another generous raise in just one more year. I reluctantly accepted it.

I was overall pretty unhappy with the lack of agency I had over my own life, when a former classmate mentioned that an editor of his was looking for some outside help with a project at the Toronto Star’s small business section. I jumped at the opportunity to work for the country’s largest newspaper, well before I figured out how I’d do so while stuck in a tiny, open-concept office from 9 a.m. to 6 p.m. with a boss who wouldn’t be too fond of me side-hustling for another outlet. I could do the writing portion during evenings and weekends, but I needed to speak with sources for these stories, and it seemed unlikely that I could reach them outside of standard business hours.

My first solution was conducting interviews in the stairwell of the office during lunch breaks, but that quickly proved unsustainable. Not only was there a high likelihood of getting caught but the background noise of workers marching up and down the steps during their lunch breaks made it difficult to hear my interview recordings clearly. Eventually I found a new trick. 

My small business stories required interviews with experts in Canada, but they didn’t necessarily have to be in Toronto. If you looked back on those stories (i don’t know why anyone would) you’d notice that most of my interviews were with sources based in Vancouver, whom I’d speak to after 3:30pm Pacific, well after I made it back from work on the east coast.

I kept that up for a couple of months until my uncle connected me with an editor from Canada’s second largest newspaper, The Globe & Mail. He was a business reporter but didn’t recommend that I continue pursuing business journalism, seeing as the field was already crowded and more welcoming to MBA graduates than journalism majors.

In that conversation, however, I told him that I was hoping to eventually become a remote working, full-time freelancer. “Those are all the buzz words our careers section editors are struggling to write cover,” he told me. “You should speak to them.”

So he connected me with the careers editor of the Globe and Mail, who gave me my first assignment in early 2013 with a one-week deadline. For that assignment I took a sick day from work and did the whole thing in one day, which impressed the editor enough to give me another try. After a couple more it started to look like I might actually be able to cover my rent as a freelance journalist, as long as I was fine with a food budget of $25 a week.

Pro-tip for new freelancers; you can get a half dozen bagels for about $4, a package of cheese for $5, and some vegetables for another $5 and if you really want to live large, some canned tuna and mayo for about $7. Throw in a dozen eggs and some bread and that should cover you for a week.

What can I say? Some dreams taste like champagne and caviar; mine tasted like melted cheese on a whole-wheat bagel with avocado, tomato, onion, and a on really good week some tuna.

In January of 2013 I earned enough as a freelancer to cover my rent. In February I made $200 more, and by March I cracked the $2000 mark, but only by $10. That’s when I decided to quit my full time job, and take the leap into freelancing.

The first month I put all my focus and energy into freelance, in April, I earned nearly $6,000, though it would be a long time before I saw a month like that again. Through the remainder of the year my salary fluctuated widely, but in the end I earned almost exactly what my former boss had promised I would make that year, before changing his offer.

When he rescinded his offer I couldn’t have imagined making that amount on my own, while working for myself and doing work I actually wanted to do.

After that my mind was made up: I was going to do this for the rest of my life.

Once I started freelancing other opportunities started to arise too; suddenly I could travel, I could pitch any publication I wanted and I could even start pursuing my dream of being a music reporter. You can read more about that in my next post.