Sales Reframed | How to Turn Cold Calls Into Warmer, More Authentic Connections

Reframe Takeaway

After listening, you’ll understand that breaking through isn’t about being louder. It’s about being more personal, more prepared, and more persistent than everyone else trying to get their attention.

Episode Guests

Tyler Hilton: Musician, Actor (One Tree Hill, Walk the Line)

Shari Wenk: Sports Agent, Author, Collaboration with top athletic trainers

Mike Bickerton: TV Producer (Amazing Race Canada, Blown Away)

Jack Oremus: Entrepreneur

Top Episode Learnings 

1. Personalize the Outreach and Demonstrate Your Capability. Effective outreach is specific. It reflects real understanding of the person you’re trying to reach. Don’t just tell them you can help – show them how you can solve their problem or add value.

2. Persistence Builds Trust and Opportunity. Big opportunities often take time. Jack Oremus meticulously crafted his pitch to Yes Theory — and even then, he had to try multiple avenues before it reached them. Mike Bickerton remembers a team that auditioned for The Amazing Race Canada for ten years before finally making it onto the show. Shari Wenk nurtured a professional relationship with Tim Grover for eighteen years before they published a book together. Their stories remind us that “big breaks” rarely happen overnight – they’re almost always the product of showing up, day after day.

3. Rejection Isn’t an Ending – It’s Information. Every outreach, audition, or pitch offers data. A “no” often means something about the timing, fit, or readiness isn’t quite right. The best performers treat rejection as a data point, a cue to adjust, refine, and continue forward. What separates those who break through from those who don’t? They keep going.

Resources Mentioned in This Episode

"Should I Open This Email?" — Research study by Carnegie Mellon University on email subject lines and open rates

"Cold Emails are the New Cold Calls" — Article by Eric Janssen and Ryan Standil in The Globe and Mail's Leadership Lab 

Jack Oremus's Yes Theory Application Video — "I want to join the Yes Theory team" 

Yes Theory — YouTube channel and digital media brand 

The Amazing Race Canada — Reality TV competition series 

Blown Away — Netflix glass-blowing competition show 

Tim Grover — Personal trainer to Michael Jordan, Kobe Bryant, and Dwyane Wade 

Winning: The Unforgiving Race to Greatness - Tim Grover with Shari Wenk

Relentless: From Good to Great to Unstoppable - Tim Grover with Shari Wenk

Case Example: The Listener by James Christensen Painting

Transcript

ERIC JANSSEN: I have a framed print in my office of a painting that I love by an artist named James Christensen. It's called The Listener. And I think it's a great depiction of what the modern world, especially the modern professional world, can feel like.

In the painting, there's a sea of cartoonish characters all clamoring over one another. We've got clowns, musicians, politicians, military-looking people, animals, you name it. And they're all fighting for the attention of this one solitary, peaceful figure in the middle of the frame. And I can relate to that guy. I think we all can. Sometimes it feels like there's this cacophony of noise in our daily lives, and we're all struggling to find the mute button.

The average working professional now gets upwards of a hundred emails every day. And research shows that people who get more than a hundred emails a day respond to less than 5% of them. And that's just email. Add to that LinkedIn messages, Instagram DMs, Slack, Discord, Bluesky, and every other channel and platform that exists. And pretty soon you feel like the guy in the middle of the painting.

So here's the thing. When you're in sales, your job is to be the one voice in that sea of sameness that actually breaks through and connects. Your mission is to grab their attention and turn what could be perceived as an interruption into interest.

Hi, I'm Eric Janssen, an entrepreneur turned sales professor. And I have a simple mission, to change the way people think about sales, because sales isn't just a job skill. It's a life skill. And this is Sales Reframed, a podcast brought to you in partnership with Ivey Executive Education.

This time around, I'm joined by musician and actor Tyler Hilton, sports agent and best-selling author Shari Wenk, award-winning TV producer Mike Bickerton, and the dynamic entrepreneur Jack Oremus. And our topic, how to warm up your cold calls.

Digging into your background a little bit, there's a story around you doing cold calling a radio station.

TYLER HILTON: I was playing a bunch of coffeehouse gigs when I was 15. And I was covering this guy named Jonny Lang, this blues singer who was a teenager. My dad's like, they're giving away Jonny Lang tickets on this radio station. You got to call in. And I was like, I'm not doing that.

ERIC JANSSEN: That's Tyler Hilton. He's a musician, actor, and author. You might have seen him on the hit show One Tree Hill or maybe playing Elvis in the Johnny Cash biopic Walk the Line. Tyler comes from a family of musicians. When he was young, his dad heard him singing and playing around the house. He immediately recognized his talent and encouraged him to get out and start playing in public to build his confidence.

TYLER HILTON: My dad's like, you got to play some of these songs you're singing at a coffeehouse. And I was like, what? That's a hard no. I would feel like throwing up every time at an open mic when it's like, this is where all the worst people come to sing for the first time. And even then, I was like, I'm not good enough to be up there, you know?

ERIC JANSSEN: But Tyler pushed through the nerves and started playing in public venues, and eventually, he got comfortable in front of a big crowd. Turns out he was also comfortable enough to call into that radio station, with a little prodding from his dad.

TYLER HILTON: He's like, you got to. I feel like they're going to love it. And I was like, why would they care about-- I was a freshman in high school. And somehow he convinced me to do it. I was like, hey, I'm calling for Jonny Lang tickets. She's like, what kind of stunt are you going to do on the air for the tickets? And I was like, nothing that crazy. I'm going to sing a Jonny Lang song on my guitar.

And she's like, OK, can you sing me some of the songs? So I put the phone down in between my legs, and I sang it. And I was like, this isn't crazy. People were doing crazy [BLEEP] for these tickets. And she was like, hold on, I'll put you on the air. And I was like, is that because it was really bad or really good? I didn't understand what the catch was. And they put me on the air. It was a nationally syndicated show.

And then afterwards, they were like, yo, you can have the tickets as long as you call us tomorrow after the concert and tell us how the concert was. So I called them back, and they said, hey, can you play another song? We got a lot of calls. People really liked your voice. And then they just kept having me on their show over and over just because I called in to get these free tickets. And they gave me my first fan base. They helped me do my first record.

ERIC JANSSEN: Tyler's call to the radio station turned into something much, much bigger than a free ticket. It was the spark that launched his entire career.

TYLER HILTON: Everything came from that one call in for the tickets. Crazy, way outside of my comfort zone.

ERIC JANSSEN: I want to go back to that story that Tyler told for a second, because I think it's easy to look at it like this once in a lifetime, right person at the right time moonshot story. I mean, most of us are not super talented musicians who happen to also have Hollywood actor levels of charisma and good looks, right? But if you dig into it a little bit, his story has takeaways for how we approach sales specifically when it comes to those crucial first attempts to connect with a potential customer.

I wrote an article for The Globe and Mail's leadership lab a few years ago called "Cold emails are the new cold calls." And in it, I give a three-part framework for how to improve response rates in cold messages. One, personalize, two, be concise, and three, demonstrate capability.

And when you think about it, Tyler did all three of those things on his call. In just a few seconds of conversation with a producer, he managed to stand out. He personalized it. He showed that he wasn't just some random kid calling in for free tickets. He was able to quickly show that he knew the artist, he knew the songs, and he had talent to showcase. He was concise.

When the producer asked what he was going to do, he had an answer and had his guitar at his side and he definitely 100% demonstrated capability. It only took him a few seconds of playing guitar and singing over the phone to show the producer that he was good. He got there really quickly. And by doing those three things, he made it obvious to the producer that putting him on air would be a win for everyone. Tyler wasn't just asking them for something. Rather, he made their job easier too.

SHARI WENK: I don't say cold calling, but you have something you want to put out there, and you have to have a method for doing it. I don't personally believe in having this is the process. I don't think it's the five-step process to better sales. That may work for some people. It has never worked for me. But I'm not a five-step person.

ERIC JANSSEN: That's Shari Wenk. She's a sports agent and best-selling author. She's the founder of the SLW Agency and has negotiated hundreds of millions of dollars in deals for clients like Terry Bradshaw, Sam Smith, Dennis Rodman, Walter Payton, Randy Johnson, Nolan Ryan, Skip Bayless, and dozens more.

I wanted to talk to Shari for this episode because so much of her professional career has hinged on grabbing the attention of a potential client and making the case for herself as the best possible person to represent their interests. She doesn't like to use the term herself, but I'll say it anyway. She is a master of the cold call. Just a quick side note, I actually pitched this interview to Shari by sending her a direct message on Instagram. It was a cold call. So when I had a chance, I had to ask her why she said yes to us.

SHARI WENK: You got me at a time when I had some clarity. I had some bandwidth. You hit me repeatedly. You were persistent. You were very clever in how you were persistent. You were showing you're a serious person doing serious work, and you care about what you're producing here.

ERIC JANSSEN: When I reached out to Shari, I pitched the interview as something that would have value for her. I thought this might be a chance for her to access and speak to an audience that might not already be familiar with who she is and what she does, but would be aligned with her message and actually excited to hear about it.

One of Shari's biggest clients is Tim Grover. Today, he's a businessman and motivational speaker, but most would recognize him as the personal trainer to some of the most elite athletes in the world. He's worked with Michael Jordan, Kobe Bryant, and Dwyane Wade, just to name a few. Shari told me that even for someone working at Tim's level, when it comes to adding new clients to the roster, they're still making cold calls. And her strategy? Try making them a little bit less cold.

SHARI WENK: So the first thing I do is think about, who do we know? Who do we know? Do we know anybody connected to this person? Is there any connection whatsoever? Did I see you at a thing? Did I run into you somewhere? Do I know someone who works in some capacity with you? Look at their LinkedIn. Who do you know in common? Is there somebody that can make an introduction? Look at their Instagram.

Listen, it doesn't hurt. Send a note. Bob, I love your work. I admire your posts. I have a great opportunity. Or I have a da, da, da. Watch what your competition is doing, watch their interviews, find out what are they doing out there. And how can you then position yourself to be competitive with that?

If you're in that type of business or the product, the industry that you're in, you better know it inside and out because when you're going to talk to somebody about it and you don't sound informed, someone else is going to sound more informed than you, and that's who's going to get the business because you just haven't done your homework. And it's too easy not to do homework. There's no excuse. It's all right here. Everything you need 100% is sitting there. No excuse. None, none.

Don't be a clown. It's as transparent as can be. If you're dealing with successful people, they know. Don't wait to be invited to that party. A lot of people do. Can I pick your brain for 15 minutes? You cannot. My brain is not to be picked. Can I buy you a cup of coffee? No, that doesn't work for me and/or for my very busy clients. They're like, you made it too easy for them to say no. Can I? Should I? No.

Just give them what you want them to see. I'm going to send this to you. Put it in a form that you can literally communicate it in the way that you're trying to communicate with them. Throw them a link to something. I'm going to show you this. I'm going to let you see it right now. You might catch their attention.

ERIC JANSSEN: And part of catching their attention is making clear what's in it for them. That first message shouldn't just be about how great you are. It should be about how great you could be for the customer. Going back to that Globe and Mail article I mentioned earlier, the one where I talked about how to write a successful cold email, there's something I didn't actually talk about in that article.

You can think of it as step 0 of 3 maybe. And that's the subject line. When someone opens their inbox, all they see is your name in the subject line. And those two things are going to make or break the decision to open that message. And remember, professionals are responding to maybe 5% of the messages they get.

I imagine you, like me, have at some point experienced that all-consuming existential dread of trying to write the perfect subject line for an email. It's bad enough when you're writing to someone that you already have a relationship with, but when it comes to writing a cold email, it can be really tough.

Thankfully, some really smart folks at Carnegie Mellon did some research into what makes an email worth opening and published it in a study called, should I open this email? Here's how it worked. The researchers conducted what's called a think aloud study. That means they asked people to go through their inboxes in real time and verbalize whatever they were thinking as they completed the task.

They were looking for the commonalities that led to the email actually being opened and read. What they found was that really effective email subject lines share two things, inferred utility and curiosity. Curiosity is a little more self-evident but also a bit counterintuitive. Turns out that participants in the study were actually more likely to open messages when they had moderate levels of uncertainty about the content.

So maybe it's a case where you're writing to someone you know, but the subject line is vague or mysterious enough to pique their interest. They know you're a serious person. So you wouldn't be sending them spam. So what is it that you're sending them?

Conversely, maybe this is someone you don't know, but the subject line manages to catch their eye because of that inferred utility. It's just specific enough to make them wonder, who is this person that seems to have the answer to my very particular problem?

But there's a catch. One thing that has a big influence on whether or not a person opens an email is demand, which is to say how busy a person happens to be or how many demands are being placed on them at that particular moment. So that means you want to do everything you can to make sure that before you send that first email, the person on the receiving end already knows your name. Personalize. On average, it takes seven impressions before someone's familiar with you.

OK, so that Carnegie Mellon study focused very specifically on email, just like my article in The Globe and Mail. And that's because until pretty recently, email was the go-to for real business communication. AI tools have really disrupted the status quo. And while in my personal opinion at the time of this recording those tools aren't quite there yet, things are moving really quickly.

So I want to stress that what we're talking about here are principles, not tactics. Whether it's an email or meeting someone at a networking function, or dropping an IM on whatever socials, or phoning into a radio station, I believe the principles are the same. So let's talk about that idea of demonstrating capability a bit more. It's not just something that matters in an email.

JACK OREMUS: I think it's very natural to have passions that evolve. As you grow older, the world evolves around us. And so nothing is remaining static. And I think that that's a sign that you're growing as a person.

ERIC JANSSEN: That's Jack Oremus. He's a young entrepreneur who I first met after I stumbled on a viral video that he made. Jack grew up with lots of interests, baseball, real estate development, cooking, beekeeping even. Throughout his academic career, he was always searching for a way to integrate all of these passions into a career.

JACK OREMUS: What makes you unique? What makes you you? And finding the intersection of whatever that crazy combination of interests are, that's going to be the thing that you are-- that makes you one of one in the world. I might be the only person in the world that has an interest in beekeeping, snowboarding, video editing, and developing apps. I don't know how all that's going to fit together, but that's probably going to make me pretty unique.

ERIC JANSSEN: In 2019, he graduated from an entrepreneurship program at USC in California. Coming out of that program, Jack knew that he really wanted to pursue a career at the intersection of coding and digital media. It seemed like a sweet spot between his more creative aspirations and his desire to be a part of the digital infrastructure that helps other creative people get their ideas out into the world.

JACK OREMUS: YouTube and YouTubers, right? They're commanding so much attention. If you look at the views that they're getting on videos, they pretty much blow everything else out of the water if they do it right. And everything's very public. For me, I just saw it as being the future.

ERIC JANSSEN: When Jack started digging deeper into this world, he came across a channel that was run by a digital media brand called Yes Theory. And something about the way Yes Theory was approaching the platform really clicked with him.

JACK OREMUS: For those unfamiliar with Yes Theory, their motto is seek discomfort. And they're always putting themselves in intentionally uncomfortable positions where they're forced to grow as people. That might be something fun like asking a random stranger to go on a flight to Hawaii to cage dive with sharks or trying to sneak into Justin Bieber's Oscars Hollywood party or something like that.

I really resonated with them. I looked at how to work with them. And on their website, they had at the time a pretty standard form. What's your name? Upload this. Maybe there was a resume or CV field, or tell us a little bit about yourself thing.

ERIC JANSSEN: Jack wanted to connect with Yes Theory. And he knew that meant making an impression. Problem was, Yes Theory was and still is huge. With almost 10 million YouTube subscribers, Jack rightfully assumed that their inboxes were going to be overflowing with people just like him coming at them with the exact same ask.

So he needed to figure out how he'd stand out from the crowd. He knew he'd need to make sure his outreach showed that he wasn't just some random kid. He wanted to make it clear that he was a fan of their work and wanted to become a collaborator, but he also knew that everyone who was reaching out to Yes Theory was probably thinking the same thing.

Jack wanted to go one step further than the competition. His first step? Do your homework. Specifically, Jack started watching the video content that Yes Theory was producing and began taking notes. He also took a look at the video reels that other successful Yes Theory applicants had sent in. Could he find a magic thread, a way of standing out and break through the noise? And just so you know, at this point, Jack had no background at all in video editing.

JACK OREMUS: I studied these things relentlessly. I looked at how fast the cuts were, how many cuts there were. When did music come in? What was it exactly that they were doing to stand out in their own application process? What was their story? What were all the things that made them really stand out? And over the course of I'd say about a month, month and a half, I tried to think of all the ways that I could stand out.

And then I started to make my own video. In the back of my head, the thing that I would say I always had in mind was that I was really only making it so Yes Theory would see it. I never made it with the intention of trying to go viral or trying to get anybody outside of Yes Theory to see it really, and that it would be something that they viewed as being impressive enough to the point where they would take me on.

ERIC JANSSEN: Jack put together an incredible video that he titled simply, I want to join the Yes Theory team. It's succinct at 3 and 1/2 minutes and outlines Jack's biography, his interest in Yes Theory, and the ways he hoped he could help take the group to the next level. You can find the whole video on YouTube, which we'll link to in the show notes. But here's a short taste of what he sent them.

JACK OREMUS: I think life is about saying Yes to those opportunities you might be scared of. It means being vulnerable, risking embarrassment and judgment from others. But one of the most beautiful realizations that I've had was that it's not about proving anything to anyone else. It's about proving it to myself. So Yes Theory, I stand before you, asking not to work for you, but to work with you, to show the world the power of saying yes, to actively seeking discomfort, and getting the most out of this crazy thing that we call life.

ERIC JANSSEN: It's really, really impressive. And it demonstrated not only that he was enthusiastic and had done his homework on the Yes Theory brand, but he really pitched himself as a person who could be a benefit to the group, someone who'd be able to hit the ground running and have an impact. He demonstrated his capability.

[MUSIC PLAYING]

There were some other pieces in the video, though. You put time into listing out a hundred or dozens and dozens of creative ideas. You had started the development of an app that they could potentially further develop and actually use.

JACK OREMUS: Yeah, there is my story. And then I would say there was the value add piece of it, which was more, OK, how can I actually contribute to the business that you're trying to run? I didn't necessarily view myself as being a video editor.

I think I was also very drawn to the business side. I had the experience in doing mock-ups in Figma for apps, not really developing any, but I really like the user experience. Yeah, I put something very simple together, had that there, tried to come up with as many different ideas that I could, whether it be their video ideas or business ideas, how they can incorporate live events.

ERIC JANSSEN: In addition to the Figma app, Jack also built a website to showcase all of the ideas that he couldn't fit into the video and compiled a database with hundreds of other content ideas.

JACK OREMUS: I really wanted to show that I could think about these larger ideas. Whether or not they did anything with them, it was up to them. But I think at the same time, it was such a great exercise for me to think like that and not only to show them, but I guess as a byproduct, show everybody else too.

ERIC JANSSEN: So in 2020, Halloween 2020, to be precise, Jack uploads his video and nothing. He waited and waited and still nothing. So after a couple of weeks, he regrouped and tried to find a different way in. Yes Theory had an active community on Reddit, and he figured he might be able to generate some interest there.

JACK OREMUS: I reached out to the Yes Theory Reddit community, made a post, said, hey, everyone, I made a video trying to work with Yes Theory. I love what they're doing. I'd really appreciate it if you watched. And then that post itself actually got a lot of traction. And I think it drew a lot of traffic to the video, and a lot of people started to comment. And eventually, the video after that just completely took off.

ERIC JANSSEN: If you look up that video now-- and we'll link to it in the show notes-- you'll see that the top comment comes from the Yes Theory account. And it reads, this is amazing, Jack. A lot of effort and intention put into this. I also appreciate all the references and humor you added. I'm currently not in LA, but I'll message you on Instagram. We'll see what we can do. Thomas.

Remember, Jack was focused. He didn't make a generic video and send it out to every company he thought might need an editor. He picked Yes Theory and focused on making the best possible pitch, one that was tailored to them and showed that he was capable of doing the type of work he'd been asked to do on the job.

After all of that work, after the push to demonstrate that he'd be a great fit, and after seeing the video to the Reddit community, finally, the Yes Theory team did get in touch. And Jack? Well, he got to work with Yes Theory. He landed his dream job. And, of course, that job led to even more opportunities.

JACK OREMUS: It was crazy. I mean, it brought so many opportunities outside of that. And I think what was my initial goal-- I wanted to learn video editing. And over the course of making that one video, I actually learned almost everything that I needed to learn. Or at least if you're looking at the 80/20 of it, I probably learned the 80% that was the most applicable.

I think there were a couple lessons there, one, just not waiting for permission to do the thing that you want to do, right? If you have the motivation, try to go and do it. I'm all for trying to connect with the right people. And I think it still brought me amazing opportunities. It was a great foundational piece really for what came after. And it definitely changed my life.

ERIC JANSSEN: Just like Tyler's story from the top of the episode, there's a lot to take away from Jack's story here. You can think about what Jack was doing as a kind of account-based marketing. That's ABM. ABM means turning off the fire hose of anonymous spam emails and being extremely targeted in your approach to outreach.

ABM is laser focused on opportunities that you've identified as being a good fit, and it focuses on accounts or people rather than markets or industries. That let sales and marketing teams work together, which is more efficient for everyone and tends to yield higher conversion rates. Customers feel heard. The experience feels more personal. And there's a higher ROI all around.

It means looking at what the potential account is doing, what they need, how they're positioning themselves, all of the stuff that Jack did before he sent off his video, and then using all that information to craft a pitch that is surgically honed to grab the customer's attention.

MIKE BICKERTON: I worked on Canadian Idol, So You Think You Can Dance Canada, Canada's Next Top Model, Top Chef Canada. And then we moved out of that into Amazing Race Canada.

ERIC JANSSEN: That's Mike Bickerton. He's a veteran producer in the reality TV world.

MIKE BICKERTON: There's so many different jobs that I do, but mostly what my job is, is to sit across from somebody in an interview like, say, teams on Amazing Race and say, OK, you did the zip line through Banff. You failed. You got eliminated. But talk to me about this. I have to talk people through some things that they don't necessarily want to talk about. For me, sitting there as a producer, I want to know that my editor will be able to take a clear sound bite that somebody's thoughts in their own words and express who they are.

ERIC JANSSEN: Now more so than ever, TV is a fight for the viewer's attention. People have a lot of options, and convincing them to sign on for something new, something unfamiliar, can be a real challenge. So Mike mentioned that he worked on The Amazing Race Canada. And on the flip side of Tyler's story, Mike has actually been the guy on the other side of those cold calls. He's gone through thousands of applications and auditions from potential contestants on the show.

I wanted to know what it takes to make an impression, to get a call back, and maybe even make it on one of these shows.

MIKE BICKERTON: When I'm screening those casting tapes, it really is trying to figure out, who would I be excited to tell my friend that I just watched their casting tape? That is what an audience does. It's, hey, you have to watch this show that I saw last night. Or, Mom, come in here there's a hilarious woman on the TV that you're going to love.

Or there's somebody who reminds me of Uncle Jack, and he's the worst. And everybody hates him the way that we hate Uncle Jack. You got to come watch this. It's really just, is this person somebody that I want to tell somebody else about? And then do I want to tell a couple million people about them?

ERIC JANSSEN: So clearly, making an impression is important. But there's more to it than that. It's about making the right kind of impression and framing it as something that's going to have some value to Mike and to the rest of the people making the show.

MIKE BICKERTON: The casting for a show like Amazing Race Canada is a lot of volume. We're basically just asking, pick a partner that you think you want to win $250,000 with. A lot of people will say yes to that. A lot of people will submit a tape.

But the show isn't just about just finding people. It's finding people whose relationships are going to be interesting from episode one to episode 10. A lot of times, when people submit their casting tape, it's, I love this show. I would be amazing at this show. You'd be stupid if you didn't pick me. Look at me. I'm Captain Canada.

And to a point, I enjoy a little bit of that. I like someone who's going to be outgoing and extroverted, but I really need to know, who are you racing with and why? You could choose anybody in your world. Why did you choose your dad? Why did you choose your roommate? Why did you choose your ex? I have question for exes all the time. They're fascinating people.

And it's rarely the people that are talking about how badly they want to be on the show, and it's more about just explaining who they're racing with, because at the end of the day, we know that they're going to race an exciting show, but we got to see like, what is the mother-daughter dynamic like versus a sister's dynamic versus a married couple dynamic?

And that's what always I gravitate to in casting tapes is just trying to figure out what category their relationship fits into and what's their motivation. I always try to figure out from people, why do you want to run this race with this person right now? And it doesn't mean that everyone has to say, this is our 40-year wedding anniversary, and we want to do something special. But it's just about seeing why they've picked this person to rely on. And will they be as motivated in the process?

ERIC JANSSEN: It's important to remember that often, whatever it is that's standing between you and a yes is entirely beyond your control. You can do everything right on your end. And for some reason, it just doesn't click for the person on the other side. It's not about selling yourself hard. It's about figuring out if what you have and what you are is a fit for what they're looking for and also making sure that you clearly get that across in whatever format is available to you.

MIKE BICKERTON: I think zooming out, casting is all about packaging yourself, presenting yourself, and being able to deliver a quick synopsis of who you are and what you could bring to the show. So what is your point of view? So I always tell people, just be yourself.

Any TV show that's casting-- they are looking for you. They're not looking for the person that was really popular last season. So don't try and be somebody else. Don't try and play a character. Have an authentic conversation with the people around you, and you will come across like you would in real life to friends and family that know you.

With a show like Amazing Race, there was teams that I saw year over year in the six years that I was casting. And a lot of teams would get callbacks multiple years because you just don't know what the mix is going to be this particular year, how these individuals or teams are going to fit into who is rising to the top.

And one of the most satisfying things was seeing on the 10th season of Amazing Race, four years after I'd left it, a team from Newfoundland and Labrador got onto the show that had applied every single season. Colin and Matt-- they were the most fun. We interviewed them in St. John's a bunch of times. And I was like, guys, you would be so much fun in this race. I get it if you don't want to keep applying, but if you do, I will always put you forward. And then finally, 10 years later, they made it on the show. So very satisfying.

ERIC JANSSEN: Oh, this is good. I didn't have this as a question, but this persistence, right? I think that people will send that initial cold email, cold call, whatever. And then if they don't hear back, they're like, well, I tried. But it sounds like these guys-- was it Colin and Matt?

MIKE BICKERTON: Colin and Matt.

ERIC JANSSEN: Came back. And it took the fourth time for them to actually get on the show.

MIKE BICKERTON: The show, I think, brilliantly played it up because they showed clips of all their 10 audition videos and then welcomed them onto the starting line. And it tells the audience at home like, oh, even if I applied that one time, I didn't make it during that first season with 10,000 applications-- your odds were not very good at being one of the nine teams chosen-- it gives you the cue that, yes, persistence does pay off. And there is a point to, if you want something, continue to work towards it.

[MUSIC PLAYING]

SHARI WENK: You have to have patience. You have to believe in an outcome. And you're working towards something. There's athletes that have gone five, six years in between championships. We have people listening to this that can't go five days if they didn't make a sale, they're ready to quit.

ERIC JANSSEN: That's Shari Wenk again. As a sports agent, she's in the unique position of flipping between being the customer and the one trying to close the deal. She knows about persistence.

SHARI WENK: If I cared about the rejection, I would never be able to get out of bed. Sometimes we get inquiries. I'm like, this is perfect. This is great. The timing works. The schedule works. We're going to get and I quote them. And then they just go away. I never hear from them again.

And I'll follow up once and say, hey. And sometimes they'll come back and say, yeah, the group went in a different direction. I'm good. I'm done. That's it. You know where to find me. Keep in touch. We'll connect down the road. You cannot get emotional about those things even when you think you're at the finish line. You go the distance, right? And you're right there. And it sounds like you're just all set.

And you can't wait to tell everyone. I am like, I'm closing the hugest deal. It's a done deal. Oh, it's a done-- and then it goes away. And you can't believe, and it's embarrassing and painful. You already have the commission spent in your mind. And you know exactly what you were going to do with that, and it went away. That's a horrible feeling. And it happens to all of us at any level. The biggest deals fall apart. It's not just you.

ERIC JANSSEN: For Shari, the long game is important. If Mike's story about a 10-year timeline to make it onto Amazing Race seems like a lot, how about 18 years? That's how long it took Shari to land one of her biggest clients and closest collaborators today, Tim Grover.

SHARI WENK: Tim had reached out to me during his Michael Jordan years. And he had an idea. A publisher had come to him about writing a book, and it was a huge deal. For various reasons, he wasn't sure how to manage it. And he had seen my name in the paper as someone who does sports books, produces them and represents them.

And so he reached out to me. We had a good conversation about it. I negotiated a very big deal for him. And for various reasons, he decided at the last minute not to do the book at that time. So we went to the finish line on that, and it didn't happen. And it was a very big deal to walk away from.

I followed him around with calls, emails at that time, dropping a note, seeing a thing, just keeping in touch. Hey, there's another opportunity here. Would you like to talk about a book? No, not interested, not interested. Thank you very much. Not interested. We would run into each other at various occasions. Hey, have you been good? Great.

He'd call me if he saw a book that was interesting to him. Do you know about this? But no business was done. 18 years passed. In between, that first meeting for the book about Michael Jordan-- training Michael Jordan to the day he called me and said, I need to talk to you, I really didn't even think anything of it. I'm like, I knew eventually you'd come back.

ERIC JANSSEN: I want to go back to Tyler Hilton here because his story is so compelling to me and ties together so much of what we've been talking about. When Tyler called in for those Jonny Lang tickets, it was a combination of preparation and willingness to take a shot that opened the door to some of his earliest public exposure. And it was that same willingness to take a swing that set him up for his appearance on the big screen.

TYLER HILTON: I won this national Shakespeare competition I went to in New York. And I got signed by William Morris as an actor my senior year of high school. Right at the time, I was trying to get a record deal, so they signed me for music and acting. And then I got an agent. But I told them, I'm a musician. I'm not an actor, so you don't have to worry about whatever. I don't know what I was thinking, but that's what I told them. So they're like, OK.

But then this movie Walk the Line came about, and they said, they're looking for musicians to be Johnny Cash's background guitar player. So all we need you to do is come in, sing a Johnny Cash song. And they're trying to cast people to pretty much be extras. So I was like, oh, OK, cool. That sounds awesome.

So I learned a Johnny Cash song, went in to play it. And they were like, do you know any Elvis songs? That was my favorite. All the first songs I learned were Elvis songs. And I played them three Elvis songs. And they were like, OK, cool. Thank you. And that was it. And I was like, OK, that was really weird.

My agent calls. They're like, they want you to come back and read lines as Elvis. And I was like, Elvis? Did they know that I am not an actor? She's like, yeah, they want you to read these Elvis lines. So I read the Elvis lines. Didn't feel like it went well or not. And they called me. They're like, they want to give you this part in this movie.

ERIC JANSSEN: But at the time, Tyler was focused on his music career. And his big a deal as it might seem to be offered a major part in a big budget Hollywood biopic, Tyler had reservations. And he was concerned about being able to play the part without seeming like someone doing a half-baked Elvis impersonation. So he thought about it. And believe it or not, he turned it down. He figured if it went badly, it would ruin any chance he might have for a music career going forward.

TYLER HILTON: I was like, no. I'm not playing Elvis in a movie. Like, yeah. And I'm trying to record my record, and I don't want people to think I'm some Elvis impersonator. And I was like, no, I'm not doing it.

ERIC JANSSEN: And the story could have ended right there, but it didn't. That same cold-calling muscle that Tyler had built up years earlier from calling into that radio station came in handy later that day.

TYLER HILTON: Randomly, I'm in this bar. My friend goes, I think that's Joaquin Phoenix over there. And I was like, oh, whoa. I just tried out for his movie. Then I'm like, I'm going to go talk to him. So I went over, and I was like, hey, man, I just want to say I read Walk the Line. It's so good. That's going to be such a great movie. Congrats. You're going to kill that or whatever.

And he looks at me, and I'm a nobody. And he goes, are you Tyler Hilton? I saw your audition tape. You got to do this movie. And I was stunned. I told him I'm a musician. I'm signed to Warner Brothers. I'm making my record. He's like, dude, Reese and I have been taking guitar lessons and vocal lessons for two years to get ready for this stuff. We are so nervous. And everyone they're trying to cast as the musicians in the movie aren't real actors. They're musicians because they want it to feel authentic. You got to do it.

And I was like, oh man, I said no already. He's like, that's all right. Call and tell them that you're into doing it. I'm sure you could take it back. And I called my agent from the bar, and I was like, [INAUDIBLE], Joaquin talked to me. And he was like, can I do this movie or what? And she was like, I'll call and see if it can happen. And literally, I got that movie because I ran into him in that bar. And I was ready to say no because I didn't want to do something that was out of my comfort zone.

ERIC JANSSEN: And as you probably know, he got the part. The only reason Tyler Hilton got that part was because he walked across a bar and introduced himself. That wasn't talent, and it wasn't fate. It was a decision. And that's the thing that most people miss. They think they're not the type of person who does that sort of thing, or that maybe talking to strangers is an innate talent that you're supposed to be born with. But it's not.

It's a muscle, a muscle that you build one conversation, one email, one ask at a time. And yeah, you might get rejected. You might look stupid. But the life you want, the people you want to meet, the career that you don't even know is possible yet-- they're not coming to you. You have to go to them.

So what's the one thing we hope you take away from today's episode? Take your shot. Send that cold email. Make that call. And when you do, do your homework. Customize your message and demonstrate your capability because you just never know when one uncomfortable conversation could change your life.

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Next time on Sales Reframed, it might seem counterintuitive, but when it comes to sales, research shows that listening is far more important and far more effective than talking. I like to think of it as diagnosing before you prescribe. So who better to talk to than a world-class expert in diagnoses? Dr. Behfar Ehdaie is a world-renowned surgeon at Memorial Sloan-Kettering Hospital in New York. Patients travel from far and wide to seek his counsel on prostate cancer treatment.

But here's the problem. After he was giving his expert recommendation, they weren't listening. So Dr. Ehdaie did something radical. He invited in outside experts and completely reimagined his approach, developing a standardized method for how doctors talk to patients about treatment options. What he discovered about creating structure and communication will change how you think about sales conversations.

BEHFAR EHDAIE: Even in surgery, many of our anatomic books and surgery textbooks are a step-by-step how to do the surgery techniques in surgery. We're very well accustomed to seeing a standardized approach and using that as our launching pad to personalize it. And so we felt, in a similar way, we can create an approach in communication.

ERIC JANSSEN: Thanks for listening to Sales Reframed with me, your host, Eric Janssen. Thanks to my guests this week, Tyler Hilton, Shari Wenk, Mike Bickerton, and Jack Oremus. You'll find links in the show notes to all the amazing things that they're doing.

This podcast is brought to you in partnership with Ivey Executive Education. Part of the Ivey Business School, consistently ranked among the top business schools globally, Ivey Executive Education delivers high-impact learning experiences for organizations and leaders at all levels.

From custom-designed programs to coaching and open enrollment courses, Ivey works with executives and business operators around the world to drive real results. Their mission, like ours, is to turn cutting-edge research into practical insights that help people learn, grow, and succeed in a changing world.

This show takes a village. I'd like to thank our executive producer Sean Acklin Grant and our editorial advisor James Greenhill. Our audio engineer and producer is Carol Eugene Park, and our narrative producer is Michael Catano. Thanks also to our creative directors, Cristina Ball and Michelle Stanescu. Thanks for listening. We'll see you next time.