Miles Bonsignore of ‘Try Guys’ Fame Has a New, Perfect Podcast

Producer Miles M. Bonsignore wants you to break up with your boyfriend.

While he envisions himself, a couple of years down the line, looking out across a vast floor of telemarketers in a full call center dedicated to curating advice requests for him to answer on air in his hit podcast “The Perfect Person Podcast”, for now, Bonsignore will settle for his one-man operation — answering calls on set with his freelance sidekick Will Witwer and giving advice to his podcast listeners.

As the podcast producer for the Try Guys, Bonsignore has worked on podcasts professionally for years. He’s even hosted a couple of episodes of his own “very bad podcasts that just were not good” in the past. As a result, he’s collected quite a bit of experience to apply to his newest endeavor: “The Perfect Person Podcast,” a comedy advice show where Bonsignore answers audience call-in advice requests with the goal of helping his listeners “achieve maximum perfection.”

“It was kind of easier than I thought it would be to start,” said Bonsignore in an interview with The Harvard Crimson. “I was doing the Mr. Miyagi ‘I was doing the training all along to start my own podcast’ thing.”

Comedy advice podcasting is a unique genre, but Bonsignore believes the work he does helps people beyond pure entertainment.

“Oftentimes, girls call asking whether to break up with their boyfriends. And the answer is always to definitely break up,” Bonsignore said. “People are just calling for permission, usually. People know the answer to the advice question that they're asking for.”

Bonsignore grinned, “And you can quote me on that, because it's just a flawless sentence: ‘People know the answer to the advice question you’re asking for.’” He paused. “That's good for The Crimson. That's gonna be front page news.”

Bonsignore’s comedic tone is unapologetically hyper-confident but also appears genuinely passionate. In nearly the same breath, he gives advice to take bubble baths and sensitively unpacks grief and loss.

Bonsignore cites Ben Schwartz, Jake and Amir of “CollegeHumor,” Drew and Enya of the “Emergency Intercom” podcast, and Ziwe as some contemporary comedians he admires. “I think that the way that I talk is fully ripped off of maybe 15 comedians that I really, really loved growing up, and then was trying to love their humor while writing my own stuff and adding my take,” he said. But in “Perfect Person,” Bonsignore pairs this conglomerated humor with real vulnerability, creating a project worth more than mere advice delivery.

“I went through a lot of crazy stuff in my life. And I want to share that in an effort to make people feel seen, not in an effort to gain sympathy,” Bonsignore sighed. “Sharing can be weird because it's obviously performative to share anything on the Internet. But by sharing things, hopefully, if you're being real about it, you are connecting with people.”

Bonsignore knows quite a bit about being real. In his end-of-show segment called “Get Real,” he plays somber classical music and bombards his guests with a series of highly personal questions such as “When was the last time you cried?” Although answers from guests can begin as fairly stilted and inauthentic, the segment invariably morphs into a genuinely hilarious dive into refreshing vulnerability.

“Comedy that's vulnerable generally has stakes to it. People call my show about grief, for example, something that I've experienced a lot. And I feel like that makes me feel closer to them,” Bonsignore said. “If everyone's being vulnerable, you're able to have an inside joke with a huge amount of people. Sometimes they're worse and sometimes they’re better, but generally, we all have similar problems.”

Bonsignore’s current career is a product of a uniquely internet-driven job trajectory. In college, he majored in dramatic art and media production and minored in screenwriting. He always wanted to be a performer, but was hesitant to pursue the typical rejection-lined path of auditions.

“I just thought that if I learned enough stuff, then they can't say no to me,” said Bonsignore.

He spent some time behind the camera at BuzzFeed before being hired by the Try Guys as they started their own production company. He first decided to pitch a podcast to the Try Guys after returning from his hernia surgery leave.

“I was worried that I was falling behind so I just kind of presented all these spreadsheets that I don't even know what they meant and I said, ‘What if we do a podcast?’” said Bonsignore, throwing his hands up with a shrug. “And the guys said to go for it.”

While working on the “TryPod” and several other podcasts for the company, Bonsignore transitioned from only producing content to having a heavier speaking role in the podcast, making a seamless transition from off-camera to on.

“The great magic trick of my career is that I always wanted this,” he said.

Bonsignore’s performance persona has truly blossomed with the release of “Perfect Person” and his renewed focus on independent projects.

“I feel so lucky that I get to do this. And I don't have to make copies for someone who’s mad at me for not ordering lunch correctly anymore,” Bonsignore said. While Bonsignore is still busy — “I’m a busy little boy,” he says — his days are now filled with solo projects, collaborations with other creators, and a day job with the Try Guys.

When asked if he had any advice specifically for Crimson readers out there — “So you’re saying I have a mouthpiece to the Ivy League elite at this point?”— Bonsignore delivered a few key points. “Worry less — a hard thing to pull off but just try. Take a deep breath. And take a bubble bath!”

After finding out that most Harvard dorms do not contain bathtubs, Bonsignore sighed. “You know, you see ‘The Social Network’ and you think they’ve got everything, but then no bathtubs. That’s a problem.”

Lastly, Bonsignore returned to his typical blend of humor and blunt sincerity to deliver a final piece of advice to The Crimson’s readers: “Just be nice to each other, baby!”