"Put your best foot forward" – On Brand with Jimmy Fallon contestant Ryan Winn shares how he prepared for his Dunkin’ Donuts campaign pitch

NBC’s On Brand with Jimmy Fallon introduced audiences to contestants competing for a marketing role and a $100,000 prize through brand campaign challenges.

Ryan Winn secured a win with Dunkin’ Donuts in the first campaign, explaining his approach in preparing for the pitch during an exclusive interview with GeekSided on October 3, 2025. As Winn described,

"I guess that’s really it. You prepare as much as you possibly can and put your best foot forward."

He shared insights on how he handled the pressure, adjusted during pitches, and collaborated with his team throughout the competition.

Ryan Winn details his Dunkin’ Donuts pitch preparation on On Brand with Jimmy Fallon

Preparing for the Dunkin’ Donuts campaign

In his GeekSided interview, Winn detailed the pressure of entering the competition and presenting in front of both the judges and his peers. He admitted the pitch environment created a different kind of challenge compared to his usual comfort zone, saying he was probably the most "nervous" he had ever been pitching or selling something.

"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!," he said.

When addressing how he managed to stand out, Winn emphasized focusing on what he could influence during his delivery, explaining the need to "control the controllables."

He also reflected on his campaign message, centered on the idea that "everybody’s a doer." For Dunkin’, his pitch highlighted the need for packaging that represented a diverse audience of busy individuals.

He added that they wanted the packaging to reflect this, so he used the old-school vintage "Power Pail."

Adjusting pitches in real time

Winn explained that in the second campaign, he encountered similarities between his ideas and those of other contestants.

He described the challenge of differentiating his pitch while presenting after others with comparable approaches. Winn said there are going to be similarities, and the key question becomes how to best deal with them to "differentiate your pitch."

To stand out, he added theatrical elements, drawing from his background in performance.

"What better to break away than breakaway pants?" he remarked.

He emphasized focusing on elements within his control, explaining that he couldn’t control that somebody else had the same idea, but he could add some "flash and flair" to spark interest. The adjustment proved effective as his pitch was selected. When told by the interviewer that it worked, Winn confirmed it was successful.

Building the team and collaborating

Winn also discussed the team formation process in the GeekSided interview. He recalled selecting collaborators during the first round based on complementary skills. He explained that right away, he noticed Piper’s "box design" was strong, so he chose her as his first draft pick.

He added that balancing his big-picture perspective with teammates skilled in details was important, which is why he selected Mahiri as his second pick for his "detailed" approach and sense of fashion.

He also highlighted the value of team members suited for customer-facing challenges, noting that Sabrina’s "warmth" made her well-suited for interactions with live customers. Reflecting on the collaboration, he added,

"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."

Stay tuned for more updates.