Sam’s Journey to Meet The Queen of All Media
Sam East, a Toronto radio DJ, was just minutes away from conducting her first interview on National TV. To add to the stress, the person she was going to talk with was none other than the Queen of all Media, Oprah Winfrey. Oprah, as it turns out, is also Sam’s hero. That Sam found herself in this position was the culmination of a set of highly unlikely events that sets her story apart from a run-of-the-mill “I met someone famous” story. Sam’s unlikely path into radio, along with her willingness to be herself all contributed to this moment.
The Toronto Raptors’ loss in Game 5 of the 2019 NBA finals helped, too.
From an early age, Sam knew that she wanted to connect with people and entertain them and The Oprah Winfrey Show fed that desire. “Even as a child, there was something that drew me to the way she spoke, the way she connected with people, the way she told stories. Even though Oprah is an undeniable superstar known all over the world, when she is talking, it feels like she is talking just to you.”
After University Sam followed Oprah, briefly, into the TV world. She says, “For a while, I was working at CBC News in Toronto behind the scenes as a producer. My goal, even going through broadcasting school at Ryerson, was: I will be the next Peter Mansbridge! I want to be a serious news anchor.” Her time at CBC, however, was short and the job ended.
At this early-career crossroad, Sam recalls her feelings of hope and determination along with fear and confusion. “That really kicked my butt. I’m sitting there on EI [Unemployment Insurance] and I’m thinking, ‘Ok what do I actually want to do? Is it going after these news jobs or is it something that I really want?’ I had my heart set on TV, but I wasn’t getting anywhere. I was trying, I really was. A friend of mine said, ‘Why don’t you try radio?’
That suggestion was something that Sam needed to work through. She recalls thinking, “Naive, ignorant, early twenty-something Sam was like, ‘RADIO? Radio was obsolete! You’re not going to go into radio!’” Yet, she realized early on how wrong she was and goes on to say with a laugh, “So I made, potentially, the world’s worst demo. It was a fake demo, because I had zero on-air experience, like ZERO! It was awful. I sent it everywhere you could imagine.”
It happened that a small market radio station was looking for a new co-host for their morning show. CKSY in Chatham-Kent, Ontario saw potential in that awful demo and eventually hired her. Sam says, “People love to point out, ‘Man, you were you so green. You didn’t know what you were doing!’ As green as I was, it was instantaneous how comfortable I was and how in my element I felt. I didn’t love waking up at 4:30 every morning, but I loved doing what I did.”
For those three and a half years, Sam continued to develop her on-air style and hone her craft. She began to develop a presence on social media along with creating content to complement her on-air duties. The morning show was a good fit, as it allowed her to combine her ability to connect with people with a flair for being goofy. She was new to the industry, but to her listeners she was fearless. She could be funny, she could be serious, and she could connect with people.
Eventually, circumstance and opportunity made it time to move on.
“My mom,” Sam continues, “who I am extremely close to, was battling breast cancer. At the time, in 2017, it was a newer diagnosis. I knew, especially when she was going through the radiation, the mastectomy, the chemo, I needed to be closer to her. It would be next to impossible for me to go on with life three hours away from her.
“Around that time, I was offered a job in Kitchener, which is just an hour away from Toronto. I was able to move back in with Mom and be with her through all of that while also being able to put the work in to move forward with my career.” No one could have known at the time, but this decision put Sam on the path that would lead her to Oprah. “Virgin is part of Bell Media,” explains Sam. “There’s a lot of branches to that. Bell Media is in TV and radio markets across Canada.
“I went from doing a morning show in Chatham to what they call ‘weekend swing’ in Kitchener. That in itself was an adjustment. It made me so nervous. My first day? Oh my God, I hope no one was listening! I was back to being green again. I was a solo jock and I didn’t know what I was doing. I wasn’t comfortable or in my element. It was a nice way for me to make a lot of the mistakes and grow and help me up to where I am now.”
Kitchener was followed by a short stint in London, Ontario, which led to a call up to the major market of Toronto. Here she continued to develop her on-air persona and began to put even more effort into her online content. Today, Sam’s social media is filled with snippets from her life, sometimes funny and goofy, and other times introspective or inspiring. There is a distinct Oprah-like influence within them.
The Queen of All Media was close, but yet so far away.
So, it was with joy that Sam received three tickets from her boyfriend to attend the “Oprah Winfrey Presents: Your Path Made Clear (Discovering Your Life’s Direction and Purpose) Tour.” Oprah had just released a book and was promoting it across North America in a stadium tour. The Queen of all Media was scheduled to perform on June 14 at Scotiabank Arena in Toronto. Sam would be there, finally getting to have a live Oprah experience.
Then, the Toronto Raptors lost Game 5.
The Raptors were in the 2019 NBA Finals with a good shot to win the whole thing. Most of Canada was enjoying the run, and the thought of a championship team north of the border was exciting. As the top seed in the finals tournament, the Raptors held a home-court advantage with games one, two, five, and seven scheduled at Scotiabank Arena in Toronto. Their championship run just happened to coincide with Oprah’s Canadian tour.
Large venues like Scotiabank Arena have complex show calendars and Oprah’s date was likely scheduled months before the Raptors made the finals. Game Five could have been the clincher, but the Raptors lost by one point, forcing a game six with a game seven back in Toronto a possibility. Scotiabank Arena was forced to cancel Oprah’s show. It would not be rescheduled.
To say Sam was disappointed is an understatement. She, however, dealt with it in a truly Sam East fashion – she made a funny video. It starts with a sad Sam, addressing the camera stating, “My name is Sam, and I am an Oprah superfan.” What follows is a lighthearted but authentic short video of how gutted she was to find that she would not get to see Oprah in person.
A yellow “Wet Floor” sign, modified to read “Caution: Sad Oprah Fan” stands next to Sam, curled up in a ball, with inconvenienced co-workers stepping over her. The scene cuts to Sam, staring out the office windows, despondent and finding no joy in the summer street scene outside. Finally, she is forcibly removed from the premises as she seeks to find a solution to her problem. It’s a clever video, purposefully over-dramatic, and very genuine.
Sam says, “I remember editing this video on iMovie on my iPhone 6 and then posting [it] on my show that I host on Virgin Radio. And then I thought, ‘Uh, God. This is so silly. It’s not even funny. People are probably going to roll their eyes at me. I should just take this video down.” Fortunately, she let it ride and the next day proved interesting.
“I was finishing up some work that day around five o’clock,” Sam says, the moment still vivid in her memory. “I was about to head out and then I saw a notification drop down from Twitter that said, ‘Oprah Winfrey replied to you.’ I thought, ‘Yeah, ok, it’s probably just an Oprah fan account responding to my Twitter.’ I went on with my work for a second, and then I thought, ‘Maybe I should check that out. Just in case. See what that’s all about.’”
Sam could not have been more shocked. “The legit Oprah sent me a tweet! My hero, my idol, sent me a response to the video I was so close to deleting.” The Tweet read “Hey Sam! Come see me in Montreal. I’ll save a seat for you.”
Sam’s natural reaction was disbelief. She says, “A response to the video I was so close to deleting and she was inviting me somewhere? This didn’t add up! There’s no way this is happening!” It was real, however. Oprah Winfrey, herself, had invited Sam to come to the next show, in the next city. “I remember running and screaming up and down the halls at work, bursting into other radio stations. Live radio was happening, but I was just in hysterics.” Soon, someone from Oprah’s team contacted Sam and arranged for three tickets to the Montreal show. “Honestly,” she says, “ I felt nothing could top this moment.”
She was wrong.
A couple of days after the Twitter exchange, Sam got a notice from her company that they wanted to talk to her about the Oprah situation. “They wanted to put a video together,” Sam relates. “They do that all the time, I didn’t really think anything of it.” Sitting on a stool, the camera captures the magical moment when she is told that, while in Montreal, Iheartradio wants her to conduct an interview with Oprah. “Yeah, well, they ambushed me a little bit,” she happily acknowledges. Her stunned silence is quickly followed by a moment of disbelief and then tears of joy as it dawns on her that she is now days away from not only seeing Oprah Winfrey but actually getting to meet her as a media professional.
The meeting was to have two parts. First, Sam would have a few minutes to Interview Oprah as a member of the iHeartRadio media team. Following that, she had been given access to the VIP Meet and Greet. It was a dream come true, and one Sam was ready for. She states, “this whole thing was a lot to process, but I quickly needed to get my crap together because in two days I would be in Montreal and I’d need to maintain extreme professionalism while meeting and interviewing,” her voice turning to a whisper, “my hero.”
When Sam Met Oprah
At Bell Arena in Montreal a few days later, Sam was as ready as she could be to interview Oprah, who herself is one of the world’s best interviewers. Suppressing the urge to let her inner fan-girl out, Sam focused. She knew she was prepared. Her note cards with interview questions were placed on the floor where she could sneak a peek at them if needed. She knew, for this moment, she was not a fan meeting her hero, she was a member of the media doing a job.
Sam’s interview was to be the first. As Oprah came around the corner, it became quite clear that she was aware of who Sam was. It started with a high five from the Queen of all Media and an acknowledgment of how Sam’s video had caught her attention. Oprah then proceeded to stand on top of the note cards for the duration of the interview. Yet Sam nailed it; warm and engaging, with some of her excitement bubbling through, but still professional.
Those few moments are seared into her memory. Sam says, “On both a personal and professional level, I knew I had to be as present as possible. I could feel my heart beating out of my chest. I still remember her grabbing my hand for this high-five moment, I remember what that feels like. This is going to sound weird, but I remember what she smelled like. Oprah smells gooood!” she says with a laugh.
“The important thing is that she is so present. I know I keep repeating that, but think of the people you meet and talk to in life and how they are just kind of coasting, they are not there. It’s just such an important lesson. At that moment, in big moments, in everyday little moments as well, try and be present. That’s what I took from that moment.”
All too quickly, the interview was over and Sam was led away for the VIP Meet and Greet. Here, the professional barriers were allowed to come down and Sam was able to tell Oprah how much of her life and career was influenced by the superstar. That day, the warnings that come with meeting a hero were ignored and to great results. “Look,” says Sam emphatically, “ I’ll say this much. Oprah is on another planet. I have met other famous people who I admired in some capacity and I would have, before meeting Oprah, said the same thing: Don’t meet your heroes, because they might let you down.
“This was unlike anything I have ever experienced in my life. She was the most genuine, authentic person, especially for someone of her prominence. She’s exactly what you would expect of her. It’s beautiful, because with all the things going on in her world that we’re not even privy to, yet she is so able to remain present with you. It’s just as you would expect, and incredible to witness.”
For Sam, the interview and meet with Oprah has had a profound and lasting impact. She was able to recognize that she had taken another step professionally. On top of that, the compliments she received directly from Oprah helped to validate her career goals. This turns out to be important. Even though Sam has had many career successes, she still finds a lot of doubt in herself.
Like many others, she has had to periodically fight through what is known as Imposter Syndrome, the feeling that your success is somehow fraudulent or underserved. She says, “Especially with social media, you don’t know what is going on behind the scenes. You just see someone who is smiling and has a great life. You don’t know what they might be struggling with, right?
“Every career move that I have made, from the outside, it might look like, ‘Yeah, I’m doing a great job! No doubts in my mind that I’m going to kill it!’. Every career move I had a lot of doubt. How did I get here? This seems to be moving fast! Is there someone that should be in my shoes right now more deserving of this? It took a lot of working on myself in my own time, and a lot of mindfulness practice. It came to a point [in] summer of 2019 where I had to get a therapist. The conversation around mental health is developing and it’s normalizing, thank God, because it’s common. Almost everyone you know is going through mental health battles. It came to that point where, yes, I could lean on my friends and family, but it was time for some professional help. There’s no shame in it.”
Encouraged by her hero, Sam’s fire is well-stoked. She knows that the competitive world of Toronto radio is the right place for her. She says, “There is a pressure there. Once you get to Toronto. There are a lot of people. Millions of people and many radio stations to choose from. Not just radio stations. Sirius, Spotify, you are competing against all of it. The more eyes and ears on you, the more competition there is, but I see it as high-risk, high-reward. I’m still pushing, and it lights a fire under my butt to try hard every single day.”
About her long-term goal, Sam says, “It sounds cliche, but I would love an Oprah style show. She got to do it all. She got to interview celebrities, but she got to talk to everyday people. She got to hear stories from everyone. She got to have a lot of fun, but she got to do a lot of soul work, too. That’s what I would love. That would be my dream.”
Hard work, timing, and a willingness to be authentic and vulnerable with her audience play in Sam’s favor. And then there is this, from Oprah herself, as she answered one of Sam’s questions, “Whatever it is you come to offer, the offering gets better when you share it with people. “
Sam is proof of that.