On Brand with Jimmy Fallon's Ryan Winn talks Dunkin' win: 'I'm absolutely overwhelmed'

Ryan Winn became the first campaign winner in On Brand with Jimmy Fallon.
ON BRAND WITH JIMMY FALLON -- Pictured: Ryan Winn -- (Photo by: Kwaku Alston/NBC)
ON BRAND WITH JIMMY FALLON -- Pictured: Ryan Winn -- (Photo by: Kwaku Alston/NBC)

NBC has a new reality show, On Brand with Jimmy Fallon, where a group of marketing hopefuls go up against each other to prove they have what it takes to market for the big brands. There’s a job and $100,000 to win at the end, but there are small wins along the way.

Part of the process is pitching real campaigns to the big brands. Ryan Winn won that first campaign with Dunkin’ Donuts, and he did come close to one for Southwest Airlines as well. He chatted with us exclusively about his time on the show so far, and what it’s like to see his campaign out there.

GeekSided: Congratulations on the Dunkin’ campaign! What was it like going into that one with this whole new competition?

Ryan Winn: I guess that’s really it. You prepare as much as you possibly can and put your best foot forward. I just thought ‘Control the controllables.” That’s probably the most nervous I’ve ever been pitching something or selling something, though. It’s usually a place I feel comfortable in, but when they put you in that circle pitch pit and you see everybody looking at you, it’s like “Whoa!” It can take your breath away.

On Brand with Jimmy Fallon - Season 1
ON BRAND WITH JIMMY FALLON -- "Dunkin Donuts" Episode 101 -- Pictured: Ryan Winn -- (Photo by: David Holloway/NBC)

GS: Let’s talk the second campaign, where you had people with similar campaigns to yours. What was going through your mind as you realized you needed to tweak it on the spot?

RW: It’s tough with the order you’re doing your pitches in. That can have a lot of influence. We’re all creatives and we all come from different walks of life and have different experiences, so there are a lot of different ideas, but at the end of the day, you’re still pitching the same campaign. There are going to be similarities, so how do you best deal with them to differentiate your pitch?

What better to break away than breakaway pants? I did theater in high school and college, and I like performing, so it’s a place where I’m comfortable. But, as I already said, it’s just about what you can control. I can’t control that somebody else has the same idea, but I can add some flash and flair to spark some interest.

GS: And it worked, because you got picked!

RW: Yeah!

GS: So, going into the second stage with the teams. What were you looking for when choosing your team?

RW: I only got to pick my team for the first round. They were assigned to us the second time. So, in the first episode, I had these first impressions of people, and part of my feedback about the Power Pail was that it was a little one-dimensional, so we needed different demographics, different doers. Right off the bat, Piper’s box design was impeccable, so I knew she was my first draft pick.

Also, I’m not super detail-oriented, but I can see the big picture. I need help putting the pieces in place, and Mahiri was my second pick because of that. He’s detailed and has a sense of fashion, so it made sense.

Then Lauren and Mama Bean. I mean, Sabrina is the warmest, most welcoming person in the world, so I know when you have a challenge with live customers, you need someone like her. She’s in the public eye and very comfortable speaking with people, as you saw in her presentation. It was the dream team.

It is nice working with people and getting their different perspectives, because I’m not the most skilled in all these different areas of what we’re doing in the pitches. It’s a nice aspect of the show.

On Brand with Jimmy Fallon - Season 1
ON BRAND WITH JIMMY FALLON -- "Dunkin Donuts" Episode 101 -- Pictured: (l-r) Sabrina Burke, Pyper Bleu, Ryan Winn, Mahiri Takai, Lauren Karwoski -- (Photo by: David Holloway/NBC)

GS: And there’s going to be a marketing team in the industry anyway. What was it like going up against Bianca twice?

RW: Bianca is a fierce competitor, and I think you see that, right? I feel like there’s a brother-sister type of thing. I respect how good she is, but she’s so difficult to argue against. I’m gonna try and poke the same holes she’s coming after, and it’s a fun back and forth. It’s nothing personal, and we’re just competing, and we both believe in our style.

She’s really good at what she does. I wouldn’t say I’m intimidated, but I get excited for that competition. It was an experience! I learned a lot from Bianca just on her preparation and the way she goes about her arguments, and she pushed me to be better. I mean, iron sharpens iron, and that’s what it felt like in those pitch battles.

GS: How was it picking the holes in Bianca and Mahiri’s pitches in the second episode?

RW: When I went to college originally, it was for pre-law, so I do enjoy debating and picking weaknesses and pointing out strengths, but it’s also tough. It’s not meant to be a personal attack. You’re just trying to look at it logically, because you’re still talking to human beings. You’re not competing for points on a scoreboard, and you need to represent your idea first, and not diminish other people’s ideas in order to win.

When it came to Southwest, you can see Mahiri had the flare they were looking for. I can put my strengths out there and call out his weaknesses, like I thought a superhero theme was more about safety rather than leg space, but ultimately, it’s subjective. You’re pitching real people, and if you don’t sway enough, then that’s out of my control. Mahiri had a really good win.

On Brand with Jimmy Fallon - Season 1
ON BRAND WITH JIMMY FALLON -- "Southwest Airlines" Episode 102 -- Pictured: Ryan Winn -- (Photo by: David Holloway/NBC)

GS: What was the pressure like going into the second pitch knowing there was an elimination coming after it?

RW: That pressure was bigger than me winning the account. It’s just realizing that you have this amazing opportunity to work for On Brand and work with Jimmy Fallon. I knew I was off to a hot start, and that was great, but every other contestant, every other person, people who are becoming my friends, it’s just as equal as big of an opportunity for them, and no one wants to go home. You hate to see that door closed for anybody, and you sure as heck don’t want to be responsible for that door closing.

I knew that BT had not had the best reception on his first two pitches, and I was doing the math in my head that he could potentially be at risk. I tried to argue my butt off, but there was a lot of pressure. I got emotional. It was difficult for sure.

GS: I think you all got emotional.

RW: Yeah, it’s crazy. You’re forming a bond with these people that’s unlikely anything else. You’re working with them on a daily basis, learning from them and learning from the different walks of life and their life experiences. If you’re open to it, it can allow you to grow in a lot of ways. It’s like developing this family. You know you’re competing against each other, but there’s a lot of mutual respect in the sense that we’re all working at the same agency, and we’re on the same team.

GS: With each round, you got the initial pitches and then feedback to create the final product. What did you take from them?

RW: For Dunkin’, it was that everybody’s a doer, and I had that at the top of the pitch. All these people come from different walks of life, but we’re all getting things done, and we need fuel to get it done. They just wanted the packaging to represent that, so I went with the old-school vintage Power Pail. There was just some modulation there, with different types, like the class pack and the health care pack.

With the plane wrap, it was to be more inclusive. We wanted a variety of people from different ages and races, just all these demographics, showing off these different types of legs and different outfits.

When you’re hearing feedback from the client, it’s what they want, so you know there’s no confusion. When you’re pitching these big companies, the bottom line is their demographic really is everybody, so the message has to be as inclusive as possible with the brand messaging.

On Brand with Jimmy Fallon - Season 1
ON BRAND WITH JIMMY FALLON -- "Dunkin Donuts" Episode 101 -- Pictured: Ryan Winn -- (Photo by: David Holloway/NBC)

GS: As my last question, what’s it been like to see your marketing campaign at Dunkin’?

RW: I’m overwhelmed with gratitude and love. My family came out to watch the premiere, and we all just watched it here, right behind me. Then we went to Dunkin’ the next day and got our Power Pails. Just seeing the support and how it’s generated community and family and love, that’s what it’s all about.

And to be able to experience this with a client like Dunkin’! I never, in a million years, thought I’d be pitching to them, let alone actually have a marketing campaign rolling out with them. It’s been incredible.

On Brand with Jimmy Fallon airs on Tuesdays at 10/9c and Fridays at 8/7c on NBC.

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