Sometimes I get criticized for my attitude and how I present myself. It’s never been easy for me to deal with strong, opposing personalities. Sometimes, I confess to going too far with pettiness and I take things personally. I’m only human with it and often they are personal attacks. I then get over it and go about my day. For a good 30 minutes though I can be a child about life.
When I was younger I was criticized for acting like I knew everything and being pompous. Now I get criticized for downplaying my intelligence. I guess you can’t please everyone. No matter what I do, some people love it and others hate it.
I spend a lot of time learning stuff and I’ve acquired a wide set of knowledge. I go out of my way to talk to strangers and learn new things about them. Somewhere along the way I became an interviewer. While some people think I’m trash, I’m very good at keeping a conversation going past 2 hours. I thought it’d be fun to go over my process a bit.
From music to album reviews to interviews
On June 2, 2012 I stepped onto a stage and performed for the first time as HSR (at some point I discovered the city of Hamilton had beaten me to that name and rebranded to Holden Stephan Roy).
Over the next 4 years I tried to figure out how to hustle music. I got to a point where I was performing at least once a month and could sell like 10-15 tickets to a show. Then on a day where I had 12 people there for me, a brawl broke out outside. Believe it or not, my network was too scared to go to shows for the following year.
I was still in my anti-salesmen era and had too much pride to participate in the local scene unless I was booked. I was older than most of the people I was performing with and had a full time job with overtime to manage. Those are excuses, I was just selfish.
While I made a bunch of music and got some skills performing, I only had one song stick and even then I had no idea how to promote it. So in 2016, Chris, Daemon Kalah and I launched Behind That Suit. That’s right, Chris Chrome is as much BTS as I am at this point, despite it being my brand in principle. We started a podcast that evolved into a bunch of album reviews.
Half a million views and about 450 reviews, and other experimental content, later it became clear the review game wasn’t it. The world wanted reactions and I wasn’t into that format. We made long ass album reviews most people didn’t care for. Over time everyone dropped off and it was me doing reviews by myself.
At one point even Bonnie was doing lyrical breakdowns. She had gotten involved for a while. She’s reviewed a LOT of classic Hip Hop.
Inevitably I missed music and realized we had this podcast platform. I had dabbled with interviews a couple of times by chance. My second interview was with Houston underground legend K-Rino.
The thing about interviews is you actually meet the other person and create a connection. I wanted more.
Interviews are a networking tactic
My strategy at the time was to leverage my platform to make new connections in the city. Platforms like Joe Rogan, Joe Budden and Drink Champs had shown me longform conversational content was going to be the future. People were less interested in the concise and polished and wanted to see natural conversations that unearthed deeper truth.
Not all people, but the people like me, who I create content for.
The K-Rino interview had gone so well I was pretty confident I could do more. In the summer of 2019 I had a trip to Toronto planned and hit up the homie Clarity. I went by his studio and filmed this clumsy AF interview:
Over the next year I had several people come by the crib and do some interviews. COVID kicked in and still we had interviews here and there. My biggest hurdle at the time was getting people to actually want to pull up. Scheduling issues were a nightmare and several interviews got postponed. Once over a snowstorm.
Still by the summer of 2020 we had done about 15 of them. All in person. I appreciate all of those people. Then Legault said no one could come to my crib and after some procrastination we started on Twitch. Over 2021 I hosted over 150 interviews. I met so many people in the city and I went from relative obscurity to a name that people recognized.
Like many artists of my language, I was frustrated with the lack of platforms trying to interview me. Like many of those same artists, I had no real idea what to do next. So I started capturing the oral testimonies of Montreal Hip Hop artists. I became a platform that filled a need people said they wanted.
The world reopened and things changed
Once the world reopened there were IRL shows. A lot of why I entered the interview game was to create opportunities for me to perform. I found myself at a lot of concerts in 2022 when we were allowed outside again in Quebec.
While I was allowed back outside, so was everyone else. All of a sudden people weren’t home at 8:00 PM ready to see if their friend would bring them up across the 2 hour interview (I know why a lot of you watched). Slowly but surely the numbers died down.
To this day the majority of the interviews I hosted on Behind That Suit have less than 100 views. Funnily enough, all 9 political interviews I did in the 2021 Montreal election have passed 100 views, with Sue Montgomery (ex-mayor) being the least popular one. I realized I didn’t know who to vote for so I created a way for me to learn stuff.
I wasn’t doing this for the views, however you’d figure there’d be at least a core audience engaging with the content after all that time. Perhaps I failed to nurture and direct the people. I’m not passing the blame, our marketing was bad. If I could go back in time I’d make a whole ass intro pack explaining how things worked and why they needed to promote it.
Still, the lack of views makes people feel like the show is less good. There is less desire to participate. Meanwhile if each episode had 500+ views now, people would want to jump on more. There’d be a couple of Patreon folk by now. Now the main interview show is on a hiatus but I have not stopped podcasting.
How I approach interviews
I don’t do a lot of research for interviews anymore. Most of the people I talk to don’t have extensive catalogues of information for me to reference. Believe you me, any time I have talked to people that were “out of my league” like, Immortal Technique & General Steele I watched other interviews. A lot of the local people have limited stuff outside of social media. I always bumped their music or content though. That mattered more to me.
When I started doing interviews I tried harder to look into people. Sometimes I’d even do prep calls with folk to cover topics and content ahead of time. Mostly it didn’t add a lot of value. My genuine surprise at hearing about stuff for the first time on air, made for better content than a well researched Q & A session.
Also, everyone does Q & A sessions. My background with this media style is in conversational podcast formats. Super informal, as if we were all in the room toking and having a chat energy. I looked into what made guys like Joe Rogen and N.O.R.E. stand out and realized they got excited about things the guests said, that the guests were not expecting. That made them get all warmed up and willing to spill some tea. They showed intense, active listening.
I realized that you can avoid asking questions directly a lot of the time. You need a really good foundational question, one that grounds them at a place in time. I chose 5 years old as an anchor. Then I walk them through their life like a documentary.
I picture their story like a Wikipedia page and then fill out the timeblocks. Everyone has the following journey:
Young days
Beginning of school
High School
College/young adult shenanigans
Beginning of hustle
Then you focus on that
Work your way until the present day.
Ask some pointed questions about stuff like TikTok and AI.
Interview done. I’m there to get people to tell me the stuff that no one will ever ask about on most other interview shows. It’s barely an interview. It’s truly more a “conversation with” thing. It’s just easier to call it an interview.
If you guide people correctly, you just respond in a pointed enough way to get them to speak more. You don’t even need to ask a lot of questions.
The present day podcast hustle
We have not stopped making content. In 2023 I went to NYC a few times and did a bunch of in person interviews. Learned a lot about sound, gear and dealing with the border.
Littyyy Bro Flacko & I started Our PRSPCTVS last year to keep our brand alive since interviews in person are costly. Now, Mondays at 7:00 PM EST, we are there spitting our opinions on random news stories. A lot of Kanye West & Jay-Z stuff. A lot of NYC stuff.
Then on Tuesdays at 6:00 PM EST we have The Trainman Report with Alex Montagano. This is the beginning of my foray into city politics and civic issues. We do a weekly podcast show where Alex and I update the community on whatever news we think of, inviting guests on to share their story and add their PRSPCTVS.
One day I may bring Bridge The Gap (my interview show). We are certainly going to do more PRSPCTVS episodes (the other interview show with Flacko). In the meantime it’s about working on the right things that make sense. There is more interest in us talking about bike paths and Katt Williams than there is in us talking about local rappers.
Once I can flush out my team a little more, which means making more money, then I can move forward with doing all the stuff I want. For now I’m focusing on branching out beyond where I’ve been. This blog is an example of me sharpening a new sword for the world.
Thank you for reading my little recap. Anyone who reads this wants to get more involved can hit me up.
Live Long and Prosper Everyone