Luck: How Freestyling At A Pizza Shop Linked Me To Paying Gigs With Plomberie (Brass Band)
- Holden Stephan Roy
- Mar 30
- 15 min read

There are tons of unlucky people out there and I used to be one of them but thankfully I learned you can change your luck for the better.
Once upon a time I went to A Pizza in Sherbrooke, Quebec for an event hosted by the restaurant.
I ate an absurd amount of free pizza and made an Instagram story about it being… free.
Will E. Skandalz chastised me like that’s not the wave, they are our hosts and I should promote them. Later on a little lady with a trumpet pulled up and began playing away and I freestyled, over her trumpeting, what can effectively be described as an ad for A Pizza.
This little trumpet lady was so impressed she invited me to come freestyle with the band at their next performance. I took a leap of faith and pulled up at a little farmers market in the middle of nowhere. There weren’t a lot of people there but it was fun and I got invited to the next one.
Turns out I had tapped into the touristic region of Sherbrooke’s cultural efforts. I performed in front of city councillors who enjoyed what I did and this led to more invites and inevitably a cut of the bag. This one moment of guilt at a pizza store led to literal invoices for “rapping services”.
When I set out to perform with Plomberie, I never once stressed the money. In fact, many times I was surprised after the fact, that the gig was in fact paid. While I appreciate the money, it was more about seeing how people in other parts of Quebec got down.
I got to perform at cool festivals with these Quebec hippies that are so far from my Montreal life that it truly inspired me.
I got lucky meeting Plomberie when I did, so today I wanted to explore how luck is really being prepared when opportunity strikes.
I ended up with a song about a snake:
Before we get into it, if you are in Sherbrooke, I’ll be performing with Plomberie on April 11th at 9 PM, word is a new song will be written by then. Also if you want to increase your luck with having your audience receive your message as intended, hit me up and let’s work.
Life Update: Managing the connections created by lucky moments
The last couple of weeks have been a sleep deprived mess of playing catchup.
When you do get your luck meter full, and opportunities appear, your time management skills will be tested. I’ve been blessed with the problem of too much to do for so long that the stress is normal. In truth it’s not normal and I need to find better ways to handle everything.
My social media storyline effort became another example of a lucky break. It isn’t random. My last article outlines the strategy that went into my decision making. It’s lucky because this time people see the vision and want to build with me.
The day to day of managing the project is brutal. Trying to think of new things to film is tougher than I thought it would be. Unlucky for me the project now involves a lot more people, which means I need to have backup plans and contingencies in place for when people bail.
The strategy is sound, I’m still figuring out the tactics to keep it sustainable.
I’ve also been pretty burnt out so I’ll be on vacation next week where I’ll have a chance to really organize the project on paper.
On the lucky for me side, more free beats have appeared in my life as I continue writing and recording my #DADDYISSUES project. There are now 7 songs in at least some state of completion, with two, maybe 3 left to write. I just bought my third round of studio hours with Merker and as the costs go up, so does the effort to pay for it all.The first track “My Father’s Son” drops April 25 on all platforms.
I’m also going through the time consuming task of preparing for taxes. It seems like Uber is profitable after all is said and done. Between Uber and the food promo gig I am in a decent place to keep pushing forward and paying for everything. It still means the writing pace for these articles will stay at one a month.
My last song dropped March 21st, let me know what you think.
The last little update is that I just dropped 2000$ on blank shirts so I can launch my “PICKL’D” clothing line properly. Everything is just about ready to go. I’m pretty excited to have samples ready for the public by my Porchfest performance in May.
Anyone who stays a paying subscriber for 12 months will get a free shirt sent to them with whatever design they please, I got the nice quality stuff, they are worth it.
All of these projects exist because of lucky encounters with people where both sides saw the potential. I used to have terrible luck where as my mom put it, “Trouble followed me around with a capital T”. Now I just enjoy the Feel Good Shhh as I make my money, pay my taxes and hustle hard.
Let’s look at how I “changed my luck”.
The Law of Attraction is a real phenomenon
While I can’t prove this with hard facts, anecdotally I’ve seen this playout like clockwork.
The law of attraction says that positive output attracts positive results and negative output attracts negative results.
People are drawn to those that present positive energy and avoid people who are negative Nancys and hate having fun. Something I noticed on Drink Champs, all the successful people knew how to smile and make others feel at ease. I control whether my actions and attitude put forth something perceived as positive or negative and I collect people in my life accordingly.
When I was younger I had low self esteem and constantly attacked the world around me. I had an excuse for literally everything wrong in my life and it was never my fault. After years of this, nobody wanted to work with me and I was not very popular.
One day I got frustrated and just started learning about success (I’m 140 or so books deep). My output changed and while my attitude remains questionable to this day, I went from being a value drain to a value add. When my attitude finally stays positive, I’m sure I’ll find even higher calibre people in my life.
I had to learn the hard way that the attitude part is worth more than the hustle part.
In 2021-2022 I was building a local buzz and attracted a lot of attention. With those new eyes watching I chose to talk poorly about many people venting frustrations I felt no one had cared about for years. While some complaints were valid, more often than not it put a negative stain on my relationships. It wasn’t just working with me, it was taking on whatever baggage and drama that came along for the ride. This led to many of my efforts being stunted and fizzling out.
Now that I’m back on my positive energy promoting the city wave, people want to play nice with me again. It helps that my intention is to own my failures while promoting others. Even in some cases shedding light on problems we need to tackle, while taking on the role of the villain.
My actions will yield whatever outputs they do. If I find that things aren’t going my way, I take a look inward to see how I really feel about things. If it’s all sourpuss, maybe it’s time for a change. Or a vacation. My attitude can get bad when I don’t get enough rest.
A huge component of luck is the person providing the opportunity liking me. If I am sitting there being a miserable person, ignoring my blessings, it signals I’ll ignore the blessings of this charitable soul as well. They see my actions and don’t need my words to tell them.
I also realized that staying home like an old hermit was blocking my blessings.
Luck is unable to find you when you are hiding at home
Yes there is a lot to be said about social media success but that is hard work and most people aren’t down for it.
For the majority of people out of sight really is out of mind. When I am at home streaming, the people at the show only remember the people at the show. Even successful social media runs are rarely a solo person game.
Chances are that the same work will end up bringing you outside anyway.
For the rest of the population weary of internet-based networking, there are real life encounters. When I think of my corporate successes, they are largely based on people seeing what I brought to the table, literally. When the company switched to work from home and we went chat based, I felt myself become invisible to senior management.
I am not blaming anyone I worked with, my actions and inability to adapt did that to myself. If I’m being honest I was losing motivation and stopped being the value add I used to be. I certainly had opinions though, but most people stopped seeing any of the good work I did anymore.
Now I did push really hard on Twitch and the internet with interviews in an effort to provide value, make the most of COVID and meet new people. This did a lot to introduce my social media self to the world. This was a net positive in my life.
Once I was able to get outside and shake hands and look people in the eye, things changed. People weren’t just avatars, they were actual humans who now acknowledged my presence. Over time more and more humans noticed me and this led to more “lucky” moments.
When I used to do Hip Hop Karaoke, the folk at Sovereign Music Movement folk noticed me and told me they’d book me one day. Eighteen months later they popped up in my emails with an invite to be the featured guest at Big Bang Montreal. When it happened it felt so lucky, but in truth my efforts put me in front of interested eyes and that led to a cool moment.
It also taught me luck works on its own timeline.
This is why keeping a positive attitude matters so much. When I am marketing myself right, people are going to know a version of me and have expectations that are shattered because my real life attitude is poopy. I’ve burned a few bridges by not being friendly with literal fans and supporters offering to help.
Once my peers began noticing me, they started paying attention in ways I wasn’t used to.
In some cases luck came as the result of years and years of failure. The homie Flacko Bayo started elevating my life because of my consistency, despite failure. He recognized something in my work ethic worth investing in. We developed a podcast and it really helped elevate my life.
Meeting Flacko in real life elevated our relationship. Internet friendships are full of cultural gaps and ignorance. Flacko had been to Montreal, so he already had that bridge to my home. By visiting NYC and building that bridge to his home, I was able to share experiences he had talked about online. More importantly, he could introduce me to people in real life.
I got to embarrass myself in front of a literal WWE dude at a studio one time. That only happened because I took the leap and went to NYC. The more places I go and meet new contacts, the more luck I seem to have in life.
For most things in life success is linked to relationships made along the way.
The talent in luck is learning what motivates people
I find good sales people have proper luck because they can size people up and assess what will motivate them.
Let’s bring this back to music.
If someone were to ask me why they should book me, my gut reaction would be to say because I’m a talented performer.
I feel my songs mixed with the little dramatic stuff I do in between is fun and connects well with strangers. When I run that kind of logic, I find people aren’t receptive. After some research I discovered that all the successful people were talented.
Even if their only talent is capitalizing on luck.
Saying I am a talented artist is akin to telling a lady I’d like to sleep with I’m a nice guy. Nice is defined as pleasant and agreeable (literally). By telling this lady I am pleasant and agreeable, I’m not exactly coming off as titillating, I’m supposed to be nice to her if I want to do the nasty. Instead if I take the time to be imaginative and paint a nice sounding scenario, she may not care if I’m nice and be down to go engage in the fun.
While I love sharing that idea, the more important part is that nice is a relative term. Different cultural groups tend to have fun in different ways. Some people like quiet and prim and proper and some people want to get sloppy drunk and turn up. Going back to that lady, if I am to paint a “nice scenario” I need to know her well enough to come up with something she wants to do.
The first thing I had to learn about luck was that it relies on other people. They say luck is when timing and opportunity collide. To me that sounds like you just need to meet the right person at the right time to get introduced to even more people. I also include being prepared for the moment in the timing part. Sometimes I have met teams ready to move on my ideas but I wasn’t ready to lead and execute. When I am ready for some of those projects one day, I need to accept the reality that either I burned their trust in me or they won’t have the bandwidth for me.
People want to work with people they imagine will be a good fit culturally. I interpret this as people wanting to work with folk they would hang out with outside of work, even if they never do. At the very least, if no one wants to be around me, they aren’t going to want to work with me even if I can make them money.
Every time I see Plomberie it’s a good time. We’re on a similar wavelength as people and it’s easy to just jam with them. Even if I never heard the song before we have a chemistry that just works and I know when to rap and when to stop.
I have the same experience at Growve MTL, which takes place Wednesday nights at Turbo Haus. It’s a fun vibe, with musicians that respect and encourage each other performing to a crowd that is absolutely loving every moment. I’ve had so many people remember me from a Growve performance.
As I set out for the next chapters in my life I am going to need a team of people with similar goals and interests. People who are down to drive for 12 hours in a car with me while we figure out how we are going to make bank. More importantly, people who are comfortable pursuing the strategies and tactics I believe make sense.
That means I need to figure out mighty quick whether or not someone is a good fit for my vision.
Rico Blox has been an amazing partner in my storyline. I was able to make it both mutually beneficial, but also fun for us to create this content. Both filming sessions were great chill sessions. Rico Blox is now excited to build further, tapping into his connections, and increasing my overall luck score.
When I prepare to pitch someone, I take the time to figure out what’s in it for them. When you and I can be selfish together, we can create more than competing selfish interests. It will take some empathy to achieve this goal.
Basically whatever I want to do, I need to figure out why other people will care about it. Making things for me is not going to help me sell my products. I need to understand what drives others to spend time and money.
If, like me, empathy is a learned trait, it’s helpful to find a few people that can be your empathy compass in life.
The best way to increase your luck is to offer loyalty and respect
Whenever I don’t hold down my people, they turn on me quick, which is bad for luck.
There have been moments in my life where my level of shit talk is high.
Unfortunately I’ve leviedd that shit talk against people who were very loyal to me. What this tells people is that if I’m willing to besmirch the name of people who are loyal to me, then I also am willing to besmirch their name. This literally changed my luck.
I went from real upward momentum to a whole lot of people don’t fuck with me. Sometimes I got played but more often than not I did something to someone that had a ripple effect. I wasn’t aware who was listening when I was drunk and talking in front of bars. In my mind I was spitting the truth. In reality I was focusing on a bunch of negative things that brought others down to increase my chances of being great.
Only I’m not an innocent person and I have my own flaws that can be pointed out by others.
Having learned my lesson my future moves are going to be based on lifting up others. I don’t have to like you, I can even personally despise you, but I need to publicly put respect on your name. The culture of “calling out the bullshit” has turned into a lot of grown people whining instead of building. I’m ready and willing to do some work to build and so I’m focusing on the little things I can change to create better luck.
On Drink Champs a recurring theme is that if one person is winning, the whole team needs to be winning. Over the years, the record executives and power players who were the most generous with their artists, whether it was free clothing or paid opportunity, are the ones who are revered today. Most of the successful artists interviewed describe with pride how they elevated their peers with paying opportunities to create their own wealth.
Where’s that energy?
When people saw me giving out money in a contest, and putting on for the city via interviews they loved it. When I showboated and acted like I was the best rapper in Montreal, they hated. Respect and loyalty are not terms I’d put next to arrogant and egocentric.
Even writing these articles, the feedback I’ve gotten is that people appreciate the generosity in sharing insight from my mistakes. I find it therapeutic and low key selfish, but if you read my early work and compare it to the recent stuff you’ll find I did adapt. This project went from self-serving to considering you, person reading this, and what I can actually help you with.
Even if it is … lengthy.
I was blessed with a solid run in middle management at a profitable company that built a complex ecosystem. Despite the irony that you reading this probably do know these terms, but ROI, ARO and KPI don’t mean jack diddly to the average human. Since money does care about those terms, access to it is gated by social cues like good jargon.
Think about what a grant writer does, they take ideas and rework them so that the grant gets approved. I know how to structure a project for grant approval because it’s the same thing as pitching the pursestring holders at a company. Thinking bureaucratically is a whole trained vibe.
It was a painful road to learn how to make PowerPoints for C-level executives. If I can create some value for you by helping you be less dumb than me, then my articles are serving their function. The idea is by increasing this paper trail of focused efforts to build, my chances of someone finding interest in helping me increases.
After many failed attempts I finally was able to figure out that a life of service is about helping others grow. By giving them respect, dignity and loyalty, they feel compelled to return the favour. The people who bless me want to see their blessings multiply through my service.
Then they want me to not become cocky and annoying.
Humility is definitely a key to success for luck
By now it’s clear that the more I give to others freely, the more I get back from the universe.
I’m not special. There are lots of people, like you, who work really hard and have a plethora of talents. While I’ve had many “lucky moments” they are always related to my heart being in the right place. Even in my darkest, most douchey moments, I always wanted better for others. But because I was so willing to hurt others to get ahead, I got the luck that came with that lifestyle.
There are so many other factors to consider like being born white, Jewish and male in the late 80’s in Montreal, Quebec. I’ve met people my age in other countries. The way we were raised did not lead to the same level of risk taking and critical thinking.
To my fellow Canadians, being literate and being taught critical thinking skills in school is a privilege in its own right. I was gifted with a lot of moments to gain knowledge, which in turn gave me power. I remember on one date where I was feeling particularly arrogant, I belittled a girl for not understanding how algorithms shape content despite human interest.
Needless to say she did not want to see me again even though I taught her how the internet works. Mansplaining be what mansplaining do. Had I been empathetic, she may have been more receptive to my ideas, even open to the nasty. Instead, I practically laughed at her for not knowing things. Scoffing like an asshole.
Considering how lucky I was to work in a place that taught me those things, it wasn’t the right move for building better luck. People in leadership positions get there because for the most part, they help elevate others. They give people a reason to follow them. If all I do is talk and belittle, no one is going to care how smart I am.
Instead I need to be grateful I was gifted with an ability to read and write well. I can use my gifts to help others and let that signal to others that I’m down like that. I still find it selfish, but it’s based in the pragmatism of communal growth.
The trick to being luckier is to treat people in ways that make their lives better. I’m not advocating for being a doormat, enabling bad behaviour isn’t making lives better. It’s about taking on a life of service rather than a life of egocentrism.
I find it best to have faith, plant seeds and let my luck continue to grow.
That being said if you need help with branding, strategy and bringing your projects to life, holla at your boy. We can discuss your project in a free session and I can let you know if/how I can help. Let’s get that bread together.
Live Long and Prosper Everyone
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