“I’ve Hit Rock Bottom and Bounced Back Enough Times to Know It’s a Good Thing”, Building a Renowned Media and Entertainment Company With Kevin Bourne
Listen to the episode on Spotify and Apple Podcasts | Watch on YouTube
Listen to the episode on Spotify and Apple Podcasts | Watch on YouTube
“I've learned to analyze life and see the good in the bad moments. I’m willing to be inconvenienced temporarily if it means achieving something better in the long term. I’ve noticed that many people focus on short-term discomfort instead of realizing that if they push through it, something better is on the other side.”
In this episode, Kevin Bourne and I explore the power of reinvention and embracing the in-between moments in life. Kevin shares how his journey—from shy kid to political staffer, media founder, and now film and TV producer—has been fueled by constant growth and a willingness to evolve.
Kevin Bourne is a cultural visionary and powerhouse in Canada’s arts and media landscape. Kevin is a journalist, on-air personality, branding and marketing strategist, and CEO of SHIFTER Entertainment— a company creating film, TV, digital content, and live experiences with industry giants like New Balance, Paramount Global, and CBC.
Through SHIFTER, Kevin has covered Canada’s premier red-carpet events, from the Toronto International Film Festival to the Canadian Screen Awards, and has engaged in conversations with luminaries such as Kevin Hart and Ava Duvernay.
In 2023, Kevin’s expertise was recognized with prestigious accolades: he was a Golden Globe Award voter and a Rotten Tomatoes Tomatometer® approved critic. He remains deeply committed to championing Black culture and entertainment alongside his wife and business partner, Koliah, ensuring their collective work amplifies underrepresented voices and celebrates creative brilliance.
Whether co-curating Ottawa’s 40-year Hip Hop exhibit or pitching ideas in Hollywood, Kevin has stayed committed to his vision: to empower others to believe that anything is possible.
This episode is for you if:
You are focused on building for longevity, not perfection.
You want to learn how to pivot between different creative industries, from journalism to TV and film production.
You’re curious about how to build a media platform that serves local communities and fills gaps in the market.
You’re exploring how to take immediate action on your ideas to avoid losing momentum and motivation.
You’re navigating the process of rebranding yourself while balancing multiple hats in creative industries.
Looking for a specific gem?
[00:28] Kevin’s origin story and early influences
[02:10] Kevin’s Barbadian heritage and his parents’ creative nurturing
[05:03] Full-circle moments: From childhood acting to entertainment
[06:57] Kevin’s personal and professional growth after moving to Ottawa
[10:56] How the lack of media in Ottawa led to the creation of Shifter Magazine
[14:26] The journey from camera operator to founding Shifter Magazine
[20:45] Kevin’s philosophy on acting quickly on ideas to maintain momentum
[24:00] “I’ve given up on having a clear, distinct brand at this moment”
[24:29] Why Kevin doesn’t subscribe to moving in silence [completely]”
[25:18] Managing multiple roles while pivoting from journalism to TV and film
[40:16] “I’m always willing to be inconvenienced temporarily for a better life”
[32:44] The importance of building in public and evolving your brand
[50:00] Embracing change and restarting to achieve long-term growth
🎬 This interview was edited by Chara Ho, Co-Founder of Zesty Nobody
Conversation Transcript
Naomi Haile: Could you start by sharing a little bit about your origin story. You're the child of two Caribbean parents. What did you love doing as a kid?
Kevin Bourne: Yeah, so I grew up in North York, Toronto. My parents immigrated to Canada from Barbados in 1975, and that's a big part of who I am—being someone of Barbadian heritage has always influenced me as a person. My parents put me in acting when I was a child, and to be honest, I didn’t even know why at the time. It was only this year that my mom actually told me why she did it. She said it was just in case it was something I might want to pursue one day, so she wanted me to have that option.
I found that odd, because, you know, for Black Caribbean parents, putting your child into acting and that sort of thing isn’t very common. They usually focus more on education. So having me involved in acting and all sorts of creative activities—like piano lessons—was different. I was also involved in a lot of other creative things, like playing piano and saxophone, singing in choirs, and all that. It did a lot for me, honestly. My life was very creative, and I’ve always loved that. From a young age, I knew I loved telling stories. In elementary school, I loved writing and grammar. I was obsessed with it.
It makes sense now. I would crush spelling bees. If I lost, I would almost cry—I was so passionate about words. I even picked up French quickly. I was part of the first group ever in French immersion in Ontario, and my parents put me in as soon as it was available. I had a knack for languages and picked up French very quickly.
So yeah, I was always a creative child who loved words and storytelling. Eventually, my parents moved us to Mississauga for a better life. That’s where I grew up, between North York and Mississauga. I come from a small, close-knit family. I’m the youngest—I have an older sister. And that’s pretty much it!
Naomi Haile: Very cool. When you told me about getting back into acting, and how your parents had put you and your sister into commercials and auditions—pulling you out of school for these activities—it really struck me. That’s such a cool thread from your early years, and now it's resurfacing as you return to entertainment. Hearing you talk about it and reflecting on how those early experiences are coming full circle is fascinating.
Kevin Bourne: It’s one of those things where you look back and think, "Okay, I feel like I’ve been prepared for this path," whether you believe in God or the universe. I believe most people can look back at their childhood and see, even in seed form, hints of what they would become. It’s like you’re not the tree yet, but you’re a seed, and there’s evidence of what you’ll grow into when you reflect on your childhood. For me, missing school to go to auditions, being on sets, and now being on my own sets, casting people—it really feels like a full-circle moment in life.
Naomi Haile: Yeah, especially when your parents nurture that. I don’t know what your mom saw, but she saw something and thought, “Hey, this would be a really good space for you to explore and play.”
Kevin Bourne: Definitely. And I think it's interesting because parents don’t always nurture you in areas where you don’t show obvious signs of interest or talent. I was a shy child, not rambunctious or extroverted, so it wasn’t like I was giving off clear signals that I wanted to be an actor. I often wonder, what did they see? Because I didn’t really show evidence of being this outgoing performer.
Naomi Haile: Yeah, you wanted to be on screen. So, when you were at York University, you studied political science. Shortly after, you moved to Ottawa and entered the world of politics as a political staffer on the Hill. What shifted for you during that period? What did you notice about the media scene and landscape there? And what came next?
Kevin Bourne: The first big shift was within me, personally. I went to Ottawa as a shy person, and moving to a city where I didn’t know anyone really forced me to come out of my shell. I had to network, talk to people, and get to know them. I had no safety net—no group of friends I could retreat to. I literally had to rebuild everything from the ground up, in terms of relationships and connections. So, it fundamentally changed me as a person. I couldn’t afford to stay shy. It felt like being kicked into the deep end and having to learn how to swim.
On the political side, working on Parliament Hill was interesting. Parliament is such a historic place, where people like Sir John A. Macdonald and other significant figures have walked those halls. You feel that sense of history and responsibility. Being there gave me a new understanding of the rest of Canada. Coming from Toronto, where we do tend to think of ourselves as the center of the universe, I didn’t really care much about the rest of the country. But my time in Ottawa, working in Parliament, gave me a new appreciation for Canada as a whole.
In Toronto, you meet people from all over the world, but in Ottawa, I met people from all across Canada. My friends were from Saskatchewan, Newfoundland, and other places I hadn’t really known much about. It gave me insight into different parts of the country that I hadn’t even realized existed.
This broader perspective definitely shifted my outlook, but so did the responsibility that comes with working on the Hill. It’s an interesting place because one poorly worded email can have serious consequences. There were times I was dealing with the Prime Minister’s Office, the press, and other key players. I’d be about to hit send on an email and think, “Oh my gosh, this has to be right.” The weight of responsibility was intense because what I sent mattered—it could be spun the wrong way or taken out of context. That level of responsibility was something I hadn’t experienced before.
It definitely translates to business as well, where you have to represent yourself well and make sure you’re careful with how you communicate. That sense of responsibility was new for me, and it was a lot to carry. It’s one thing to study political science in a classroom, but actually being in that environment is something else entirely. I loved the job; it was one of the best jobs I’ve had, but it was also intense. Once I left, I had to detox and stay far away from politics. I haven’t gone back to it since, but it remains one of the most rewarding experiences I’ve ever had.
Naomi Haile: Wow, yeah. That attention to detail, where every word carries meaning and every word matters, really translates to your work in PR, communications advising, and working on the entertainment side of things. So, when you were working as a political staffer—I'm not sure if it was called Shifter Magazine at the time—was that when you started getting involved in meeting artists and people in music? How did that all come together?
Kevin Bourne: Yeah, it happened. When I first moved to Ottawa, one of the first things I noticed was the lack of media on the scale I had experienced in Toronto. I kept thinking, "Where's the media?" To me, even though people consider Ottawa a small town, it's still the capital city. I expected big-city media—something exciting and flashy. I kept asking, "Where's the media?" but no one seemed to care. So, I thought, "Maybe I'm supposed to do something about this." That's when a friend and I decided to take action.
Naomi Haile: Can you pause for a second, Kevin? When you were in Toronto, I guess you're comparing it to what you experienced there. For some context, can you share what your life was like in Toronto when you were in university? What exactly are you comparing the blankness of Ottawa to?
Kevin Bourne: Just being a consumer in Toronto, I started doing a few things here and there with artists, but nothing too crazy. The culture of Toronto is unique—when you're born and raised in a big city, you don't realize that the energy you bring to life is different from smaller markets. In Toronto, I was actually pretty corporate. I didn’t do anything creative until I got to Ottawa, to be honest. I was a suit-and-tie organizational development consultant, a full-time entrepreneur, and I spent a lot of time in church. My life was very structured.
But being born and raised in Toronto, there’s a certain hustle and pace of life that shapes you. There’s this ambition—this drive to achieve. When I moved to Ottawa, that entrepreneurial energy just wasn’t there. The ambition I was used to in Toronto didn’t exist. I remember the first day we drove into Ottawa, I went to a McDonald's to get food, and I was like, "Why are they so slow?" The pace, even at fast food places, was different. I was used to everything being fast, efficient, and high-energy.
As a consumer of media, especially things like MuchMusic, I was always inspired by people like Moses Znaimer, who founded CityTV and MuchMusic. He influenced a lot of what I did later on. The energy in Toronto was just so different from Ottawa. While Ottawa has since grown into a bigger city, back then, it felt incredibly slow. It was like I had moved to Timbuktu. That’s the main difference I noticed—not to take anything away from Ottawa, because it's a great place, but the energy and pace were so different from what I was used to in Toronto.
Naomi Haile: Yeah, that was a bit of a different path, but you were talking about how Shifter came to be and the spaces you found yourself in while in Ottawa. How did that happen? Was it very organic, or did you reach a point where you said, “I have to do something about this”? And what did you do next?
Kevin Bourne: So, I started by doing camera operating at Rogers TV, specifically in the sports division. Once I realized there was a gap in the media scene, I thought, "Okay, let me get my foot in the door." That’s when I started doing camera work. Then I met a friend from Ottawa who was originally from Montreal, and he suggested, "You should start an online magazine that covers this, this, and this." Usually, when people give me ideas, I’m like, "Yeah, whatever." But this one really resonated with me. I felt like I was supposed to do it.
About six months later, one of the pastors at my church also came to me with an idea for a magazine. I thought, "This is the second time I’m hearing this. Maybe I need to act on it." So, we launched the magazine, which initially had a faith and culture component. However, a report came out about what the Ottawa music scene needed, and everything we were doing aligned with that, except we were approaching it from a faith angle. We had to make a decision—do we keep the faith component, or do we focus on what the city needs? We decided to shift our focus to culture, music, and entertainment.
As soon as we made that decision, we started covering events, and people were immediately interested. They were like, "Who are you guys? Where have you been?" Ottawa really responded to what we were offering. Before that shift, our audience was mostly in places like LA, New York, Toronto, and London, while Ottawa ranked lower on the list. But we realized that since we were based in Ottawa, we needed to focus on serving the city first. Once we established ourselves in Ottawa, we could expand again to broader markets.
We approached everything with a high level of service. Coming from church, we were used to serving wholeheartedly and producing high-quality work, which translated into how we operated in the media space. We wanted to bring that same level of service to the events and artists in the city. So, we went all out—interviewing artists and being present at every event we could. Our goal was to be like CityTV, to be everywhere in Ottawa.
My passion was always about creating stars. I had this fixation on making people feel like stars, even if they were just local artists in Ottawa. I wanted people to feel like they were "somebody" when they were interviewed by us. No one else had that focus. I wanted Shifter to be synonymous with Ottawa, like how New York has Billboard or other cities have their platforms. I wanted people to say, "Ottawa has Shifter." That was always the goal.
Naomi Haile: Yeah, that’s great context, because your decision to position Shifter to align with what the city needed, based on that report, was really strategic—and it’s something you’ve done many times since. What were the signs you saw in the ecosystem? When you went to these events, was it you and some of your friends and peers from church? Did I understand that correctly?
Kevin Bourne: Well, after a while, it mostly became just me, and eventually we brought on Vladimir Jean Gill, who’s still with us today after almost 10 years. It was either me or me and Vlad running all over Ottawa, covering events like crazy. One year, my wife bought me a camera for Christmas and paid for photography lessons. Once I learned how to take pictures, it was game over—I was at every event, every show, taking pictures and writing articles.
One thing about working on Parliament Hill is that it taught me how to write, which translated well into journalism. I always knew I was a good writer, but working in communications really became the segue into journalism. So, yeah, once I knew how to take pictures and write, I was like, I'm just gonna cover everything and go crazy and all that stuff.
Naomi Haile: Yeah, that's great. Kudos to your wife for getting you that camera and for you actually using it, right? You mentioned something subtle—when two people suggested you start something, and by the second time, you thought, "Okay, I need to act on this." During our last call, you said something that really resonated with me: *If you're not faithful to your ideas, they will leave you for someone else.* You have to honor and respect your ideas, like they're a relationship.
Can you talk a bit more about this, and share any other stories where you've had an idea come up more than once? You seem to be someone who acts quickly, jotting down ideas immediately. So, what's your process?
Kevin Bourne: Yeah, I genuinely have a fear—not just of someone else taking an idea—but of knowing human nature and realizing that if you don’t act on something right away, you’ll lose motivation. So, I’m the kind of person who, as soon as I get an idea, I’m at my laptop starting a document. My wife laughs at me because I’m the "document king." I love documents. Anytime I get an idea, my first instinct is, "I’ve got to write this down." It’s my way of activating the idea and starting the momentum.
I feel that if I don’t act on an idea immediately, it will fade. You can lose the passion and spark, and once that passes, it’s gone. So, when I feel that spark, I believe you have to act on it right away—move on it, do something to activate the idea, even if it’s just getting the ball rolling. I have this fear that if I don’t act quickly, the idea will leave me, or I’ll lose the motivation.
I consider myself a doer. People have told me I’m a "manifester," but I don’t see it that way—I’m just someone who takes action. There’s an element of manifesting that’s beyond human effort, but I think the main way to manifest your ideas is to be a doer. If I say I’m going to do something, I do it. I’m not the kind of person who just talks about doing things. If I commit to something, I’m acting on it.
Every time I get an idea—whether it’s for a show or anything else—I create a document. I even do SWOT analysis documents for ideas. I’ve got a ton of them in my Google Drive because I have to create some sort of motion toward that idea. Otherwise, it could leave me, or I could become demotivated.
I never want to be known as one of those people who just talks and never does anything. Those people bother me. I want a reputation for getting things done. If I say I’m going to do something, it’s going to happen. When I enter a project—like some of the TV projects we have going right now—it’s moving forward. We’re going from zero to 100. When I put my effort into something, it’s going to move, it’s going to get done. It’s not necessarily a strategy; it’s just this sense within myself that I have to get things done.
Naomi Haile: I'd love for you to share some examples because you’ve explored many facets of the creative world. You’ve mentioned writing, producing, directing, and acting. You also had a daily Hip Hop morning show for a stint, and you co-curated a 40-year Hip Hop exhibit with the Ottawa Art Gallery. These are all things that, if I’m not mistaken, you pitched or presented yourself as you were trying to figure out ways to collaborate with more people in the city. You’ve done a lot.
I’m curious—when you wear so many hats, how do you clarify with others in the ecosystem what they should come to you for specifically? When they have an idea, how do they know, “Okay, I need to go to Kevin for this”? How do you manage wearing multiple hats while maintaining a distinct brand?
Kevin Bourne: That’s still a work in progress for me because I feel like you’re always growing and evolving. There have been times in my life where I’ve had a clear brand, but then you start to pivot, and suddenly, you’re in the middle of that transition. When you’re in the middle of a pivot, that’s when you might lose some people because they’re trying to figure out, "Who is this guy? What’s he doing?"
Right now, I’m in the middle of a pivot toward TV and film. When I was just doing Shifter Agency and Shifter Magazine, people knew me as a journalist who also did some client work on the side. But now, people are starting to associate me with TV and film. During these pivots, some people might get confused or feel unsure about what I’m doing, but I’ve had to pivot many times.
For example, when I was in Toronto, I was corporate—suit and tie, organizational development consulting. Then, when I moved back to Ottawa, I became the guy with the camera all the time. When I returned to Toronto to cover events, people would be like, "Wait, you’re the guy with the camera? I thought you were corporate Kevin." So I lost some people who only knew me as "corporate Kevin." It’s been like that during every transition—constant pivots and shifts.
Naomi Haile: Like, reinventing yourself?
Kevin Bourne: Yeah, but it's like, I feel like…
Naomi Haile: Do you see it as a reinvention, or do you see it as a natural evolution—just you, as a human being, following your curiosities?
Kevin Bourne: I think that’s exactly it. It’s just a natural part of being human to explore different things and evolve. I know there will come a time when "journalist Kevin" will fade out—there will be a time when I’m no longer that. Right now, I need to be, but you’re always evolving. In this particular time of my life, I’ve given up on having a clear, distinct brand because I recognize that I’m in the middle of a transition, a pivot. I need to educate people. That’s why I’m always posting about attending film and TV events. I’m trying to train people to think, “Oh, Kevin’s a film and TV producer.”
If people don’t know about your new path, how will you attract opportunities in that space? You’ll keep attracting old opportunities because people still see you as "agency Kevin" or "journalist Kevin." So, if I don’t actively show people the new version of myself, I won’t attract new opportunities. It’s all about messaging—letting people know, “This is my new pivot. This is who I am right now. This is what I’m doing.”
People on social media often say, “Move in silence” or “Don’t tell people what you’re doing,” but I don’t subscribe to that. I don’t tell people everything, but I do love inviting people into my process, into my pivot. It’s a way of bringing them with me, educating them, and hopefully attracting new opportunities in this new space.
At the end of the day, I’m still figuring things out. What I know for sure about myself is that I’m a storyteller, and that has been the common thread throughout my life. From third grade, when my teacher read my story out loud and praised it, to my obsession with spelling bees, to writing essays and loving essay questions in high school, to crafting speeches on Parliament Hill, the one thing that has remained constant is storytelling.
The art exhibit was storytelling. The radio show was storytelling. Every speech I wrote involved storytelling. So, if I were to summarize myself, I’m just a storyteller who loves exploring different mediums for storytelling. I realized after the art exhibit, "Oh my gosh, I just told a story." I’ve told the story of Ottawa hip hop through articles and a mini doc series with CBC, but the exhibit was me telling that same story through artifacts and visual elements. So, at the end of the day, I’m just a storyteller who loves exploring storytelling in different ways.
Naomi Haile: That was a bar. I asked you that question because I knew it was going to lead to something really good.
Kevin Bourne: I had an aha moment just right here on your show.
Naomi Haile: Yeah, and I think you made so many great points, especially about building in public and training people through messaging. That’s really just branding at the end of the day—teaching people how to associate certain opportunities or themes with the work you do.
A lot of people, during transitions, go quiet because they feel like they haven’t figured it out yet. They think they need to have everything in place before they can share it. But I believe it’s more powerful, from a connection standpoint, to show that, "Oh, Kevin is figuring it out too, just like I am." There’s a certain relief in that—bringing people along for the journey as you work through it.
Kevin Bourne: And that's something I’ve really come to recognize with social media—I'm bringing people along on the journey, and in doing so, I'm building a community. You don’t have to have everything figured out; the power lies in letting people witness your process. One day, they’ll be able to say, “Oh man, I remember when Kevin produced his first show. I remember when he was just going to networking sessions or sitting in recording studios, and now look where he is.”
I’ve had people say this to me because they’ve seen my journey. Back in Ottawa, I was in every recording studio, sitting with artists, trying to be present everywhere. Now, I’m the guy attending events in Hollywood with people like Tracee Ellis Ross and JLo. I want those people who were with me in the Ottawa studios to say, “Yo, Kevin used to be with us, and now he’s in Hollywood. If he can do it, I can too.”
That’s what I want people to feel when they watch what I do. I want them to believe they can achieve anything because I believe I can do anything. Our internal motto at Shifter Entertainment is *Everything is possible,* and I try to live by that. I want to display that mindset so people can see for themselves that if I could go from where I started to where I am now, then they can do it too.
Naomi Haile: That's brilliant. I love that for you. You’ve also had some aha moments recently, like you just mentioned. I think for me, I’ve been a little nervous about not having everything look perfectly polished online. Over time, I’ve learned that I need to let go of that in order to grow and evolve—and really bring people in. I’ve noticed that when I do that, I receive so many meaningful messages from people. It resonates with them, and I realize it’s because I’m being honest.
At the heart of storytelling is truth. Even with acting, some of the most brilliant performances happen because the actors are being private in public, and that’s what creates a deep connection with the audience.
Kevin Bourne: I think people need to realize that we’re building for the medium term. I always have my mind on the medium to long term.
I don’t mind if things don’t look ideal right now because I’m not here for just the moment. I’m thinking about being here in the next 20 years—I’m aiming for longevity.
Who’s going to remember the awkward phase anyway? It’s like going through puberty—you’re not a child, but you’re not an adult yet. You’re in that in-between stage where things don’t look great, but that’s just part of the process.
We’re often afraid of that awkward, transitional period where things aren’t polished. But if I’m going to be here in the next 10, 20, or 30 years—which is what I’m aiming for—I’m okay with that in-between stage. I’m building for the long haul. When I look at people like Kardinal Offishall, Jully Black, Jay-Z, Nas—these are people who have been at it for 25 to 30 years. I’ve only been doing Shifter for 11 years, but I’m aiming for that same kind of longevity.
So, I don’t mind if I don’t have it all together on social media right now. If I lose followers or people are confused by what I’m doing, it doesn’t matter, because I’m thinking long-term. I’m here to stay.
Naomi Haile: When you said "in-between moments," what came up for me is that those moments are still part of your life. They’re not just hidden pieces along a timeline—they are as much a part of your life as the high and low moments. You should show the same respect and honor toward those periods as you do toward your ideas.
Thank you for that. You’ve discussed your transition from Ottawa to Toronto and how you sought out different rooms you wanted to be in, which I found fascinating the first time we talked about it. Could you talk a bit about what you’re doing today? What are the new rooms you're looking to enter, and how are you positioning yourself in the film and entertainment space right now?
Kevin Bourne: Since moving back to Toronto, I’ve been getting more involved in the film and TV industry, which is where Shifter Entertainment comes in. We actually started it when we were back in Toronto. We wanted to create something that encapsulated all the things we were doing—film, TV, digital content, live experiences—because some of the projects we were involved in, like the art gallery work, didn’t really fit within the scope of a magazine. While the agency is still there, we realized we needed something broader that encompassed everything we were doing, which is how Shifter Entertainment was born.
I think I mentioned this before, but toward the end of my time in Ottawa, I found myself in rooms where I was the most influential person there. I don’t mean that in a bragging way, but I realized I had networked across and up so much that I had maxed out my opportunities in those spaces. There was no one left in the room that could challenge me or help me grow. That’s when I knew I needed to get into rooms where I was the least influential person, so I could learn, grow, and take myself to the next level.
I had done a TED Talk, taught as a college professor, and was networked with the Black community, the tech crowd, City Hall, and Parliament Hill. But I knew I needed to be in rooms where I didn’t know anyone and where everyone was operating on a higher level than me.
Just the other day, I was with a client at a big entrepreneurial growth camp for the fastest-growing companies in Canada. My client was on that list, so I was there gathering content. The conversations these people were having about AI and high-level business strategies were unlike anything the average business owner, especially in the Black community, is exposed to. Being in that room made me realize how far I still have to go in terms of decision-making and understanding business at that level, but it also gave me a clear picture of what I’m working towards. You need to be in those rooms to get a sense of what the next level looks like.
I’ve been attending more film and TV networking events as well. Just last night, I went to a BC-Toronto Film Industry meetup, where I had the chance to meet more people in the industry. These are the kinds of rooms I’m intentionally trying to be in right now.
Naomi Haile: Yeah, I didn't realize how big the BC film scene is…
Kevin Bourne: Absolutely. So, yeah, even during TIFF, I attended a Golden Globe Awards party. Since I'm a voter, I was able to go, and I brought my wife along. It was her first time attending an industry event at that level, and we were just there, taking it all in. JLo was sitting right there, Oprah was in the room—everyone was there.
At one point, Demi Moore’s team came up to me and said, “Have you met Demi yet?” I said no, so they told me, “When she comes in, we’ll introduce you.” When she arrived, they parted the crowd and said, “Demi, this is Kevin Bourne. You need to meet him.” I thought, *This is a different kind of room.* It was surreal—being in a room with the top names in Hollywood. And here I am, just a kid who grew up in North York, on Keele Street, now finding myself in these spaces.
Those are the kinds of things I’ve been exposed to lately. When I was leaving Ottawa, I had this vision of where I wanted to be, and now I’m finding myself in the rooms I once dreamed of. It made me realize why I needed to leave a place like Ottawa. A lot of people who leave don’t necessarily *want* to, but sometimes it’s necessary for growth.
Naomi Haile: Out of necessity.
Kevin Bourne: For me, when I first moved to Ottawa, I pictured being there for the rest of my life. I was such a big Ottawa guy. If anyone left, I’d be like, "Why did this person leave?" But then I reached a point where I understood why people have to leave. Now, being in the rooms that I’m in, I’m like, "Oh, okay, this makes sense. This is why."
Naomi Haile: Proximity matters.
Kevin Bourne: Exactly, right? You want to be among the decision-makers. That’s where you want to be—around people who are developing peer relationships but also in rooms where the decision-makers are present. Those are the people who, if you gain access to them, can really change your life.
I’m trying to get into more rooms where there are decision-makers, but also where there are peers who can help me grow, especially as a screenwriter. I want to be around people who can say, "Hey, let me take a look at your script." Life is a bit like school—you get to grade eight and think, "I’m on top," then you go to grade nine and feel like you’re starting from scratch. By grade 12, you feel like you run the school, but when you reach university, it’s back to square one.
That’s how it felt in Ottawa. I was at the top, but now that I’ve transitioned, it’s like being in grade nine again. I’m learning all over and working my way back up. It’s humbling, but it’s also exciting because every day, you’re learning something new, meeting new people, and discovering new aspects of yourself. It’s an exciting time of growth.
Naomi Haile: Yeah, when we were talking earlier about reinvention and evolving, you made it sound like everyone goes through these phases. But in my experience, when I’m in conversations with some people, there’s often resistance to change. I think it's natural because change is unknown and unfamiliar. Sometimes, people don’t fully measure the cost of staying the same.
When you talked about your earlier fear, I resonated with that. My biggest fear is staying stagnant because, to keep growing, you have to embrace change. You find yourself in situations where what you once thought was your ceiling becomes your floor, and you have to build back up again. But in doing so, you’re growing—you’re becoming 10 times better and more improved than before.
That said, I do believe it’s a choice. You made it sound like reinvention is just the default way everyone moves, but I don’t think that’s the case. Not everyone chooses to embrace change and evolve.
Kevin Bourne: And so that's true, that's actually true. That's actually true.
Naomi Haile: Yeah. So what do you think it is about you that makes you embrace change and want to be the least influential person in the room? Is it your love for learning, or is it driven by your ambition?
Kevin Bourne: I think, first of all, I've had my butt kicked enough times in life to know that hitting rock bottom and bouncing back is a good thing. For example, when I moved to Ottawa, I had to start all over again, and even when I moved back to Toronto, despite being born and raised here, it felt like I had to restart again. I've been through so many restarts, fallen, and gotten back up, that now I can always see the good in the bad. Even during tough times—when money is low, or I’m wondering how we’ll pay for groceries—I can look back and think, "That was actually good."
I've learned to analyze life and see the good in the bad moments. I’m willing to be inconvenienced temporarily if it means achieving something better in the long term.
For example, a friend of mine was upset about renovations in her apartment, focusing on the inconvenience, while I was thinking, "I can’t wait for her to get a brand-new place!" I’ve noticed that many people focus on the short-term discomfort instead of realizing that if they push through it, something better is on the other side.
For me, I'm always willing to go through inconvenience to get to the outcome, no matter how tough things might seem. Also, my faith in God plays a big role—it helps me feel like I’m not alone during transitions and challenges. If I didn’t have that faith, I might be overwhelmed, but knowing that there’s a higher power guiding me gives me the strength to focus on the positive rather than what could go wrong.
I also think there’s more to come for me—I don’t think Toronto is my final destination. I see other moves ahead in my lifetime, and I’m prepared to restart again, even if it's uncomfortable at first, because I know it will be good for me in the long run. I’ve come to accept that my life might never be stationary, and I’m okay with that. My life will always be an adventure.
My mother-in-law once told my wife and me that our life always seems to have another adventure on the horizon, and I don’t think I’ll ever settle into a repetitive routine. I have friends in their 30s and 40s who are already talking about working until they can retire and get a pension. Honestly, those conversations frustrate me. I can’t imagine living like that. I’m always going to chase the next adventure, the next opportunity for growth, the next ceiling to break through.
Naomi Haile: Yeah, when I was 20, I was hearing those conversations because I was the youngest person in my office, working for the public service in Ottawa. I would ask people how long they had been working there, and it was like a glaze came over their eyes—as if they had forgotten how much time had passed. Then, I’d meet others who were counting down the years, like "five years to retirement," and I just remember thinking how grateful I am now for that rude awakening. I realized I did *not* want that to be my life.
That was the moment I knew I had to figure out my next move. I started working evenings and weekends in my consulting role, searching for different opportunities, building community, starting my podcast, and eventually moving to New York. I just remember feeling like taking a back seat in my own life was not an option for me, at all.
Kevin Bourne: I remember a time when my wife and I were leading a small group at our church. Everyone in the group was younger than us, newly married or engaged. Most of them owned homes and had great jobs. I found myself looking at their lives thinking, *Oh man, I want some stability.* I wished I had a house and a stable job.
But then, everyone in the group said they wanted what we had. They told us, *You’re living your dream. We’re not living ours.* They had the picture-perfect life—houses, jobs—but they weren’t happy. When I asked the group, "Who here is happy?" no one raised their hand. My wife and I were the only ones who were truly happy, even though we were the least stable, living the full-time entrepreneur life. They were living vicariously through everything we were doing with our business.
It was a big shift in perspective for me, realizing that while I thought they had made it, they were looking at us thinking *we* had made it. It was a reminder that the grass always looks greener on the other side.
Naomi Haile: Two more questions for you, Kevin, before we wrap up. I’m curious to know—though I think I might already know the answer—what has been the best investment you’ve made in yourself, whether in terms of time or finances? And what have the results been for you?
Kevin Bourne: The best investment I’ve made, without a doubt, was getting a business coach. It really helped transform my mindset. Every month, I was paying a significant amount for her services, but the personal growth I experienced and the things she helped me work through made me a completely different person.
There were definitely moments where I saw a financial return in my business, and things started to change, but having her guidance for those four years was invaluable. I paid her a lot, but it showed me that growth is available to everyone—most people just don’t make the necessary investments to achieve that change, whether it’s paying for a coach, buying a book, or taking the time for self-improvement.
I also went on business retreats, paying thousands of dollars, and every time I came back, I felt transformed. That period of having a business coach and attending those retreats was definitely one of the most impactful investments I made.
Naomi Haile: Out of curiosity, what stage was that in?
Kevin Bourne: I finished working with her maybe last year, around this time—late 2022. It was four years before that, so from 2019 to 2023. During that period, I grew a lot. There were months where I saw incredible financial returns because of the work we did together, but for me, the growth is ongoing.
I’m constantly listening to podcasts and audiobooks because I’m really invested in my personal development. I consider myself a high-growth individual, so I’m always trying to improve. I’ve even had to distance myself from some friendships—not completely end them, but put them on the back burner—because I’m growing so quickly, and some people in my life aren’t focused on growth. That gap between us just starts to widen.
But I’d say having a business coach and attending those business retreats were probably the best investments I’ve made. Is that what you thought I was going to say?
Naomi Haile: I actually thought you were going to say relationships—investing in and building relationships. I thought that’s what you were going to mention.
Kevin Bourne: No, no, that’s definitely important too. There are certain relationships in my life, especially now with mentors, that have been transformative. One of the challenges I had in Ottawa was not having access to many mentors face-to-face. There weren’t many people doing what I was doing. But now, being in Toronto, I’ve met so many people who are much further along than me in media, film, and television, and they’ve become mentors to me.
This is my first time being mentored at this level, and it’s amazing. I have mentors now where, if I need access to someone, I can just ask them to connect me. For example, just yesterday, I was trying to get in touch with a production company, and another person had been trying to connect me for a while with no luck. I messaged my mentor and asked, "Do you know so-and-so?" By the end of the day, we were connected. It was like a door opened just like that, something that would have taken me so long to do on my own.
Investing in those mentor relationships has been huge for me over the past month as I’ve been learning more about film and TV. I’d message people whenever I hit a block—if I didn’t understand something, I’d find someone on LinkedIn who did, and ask if they could spare 30 minutes to help me out. By the end of that month, I felt like I really understood the film and TV industry.
So, investing in relationships, getting to know people, and networking has been incredibly valuable.
Naomi Haile: Yeah, for the audience, there’s a book called Who, Not How that you should definitely read. It touches on exactly what Kevin just mentioned. This has been great, Kevin—thank you! What’s the best place for people to connect with you online and support your work?
Kevin Bourne: You can find me on all social media platforms at @KBtheboss_ —that’s my old radio name. So yeah, @KBtheboss_ on all platforms, or you can reach out through Shifter Magazine, as I usually check those channels as well. But my personal handle, @KBtheboss_, is the best place to connect with me.
Naomi Haile:Amazing, awesome. Thank you, Kevin, for taking the time to be here on The Power of Why podcast. And to the audience, we’ll catch you in the next episode. Ciao!
Listen to the episode on Spotify and Apple Podcasts | Watch on YouTube
Connect with Kevin
Website: www.shiftermagazine.com
LinkedIn: Kevin Bourne
Instagram: @kbtheboss
Company Instagram: @shiftermagazine
Connect with Naomi
Website: naomihaile.com
LinkedIn: Naomi Haile
Instagram: @naomiahaile
Twitter: @naomiathaile