Building the world's largest resume™️
Creator Conversation with Gabriel DeSanti, full-time creator
Welcome to “Creator Conversations,” a weekly feature on Paid Partnership where I interview a prominent creator, agent, marketer or industry professional to discuss wide-ranging topics from outreach to negotiation to content.
“How much do you make a year?”
The often taboo topic has spawned an entire career for one NYC creator who’s at the heart of the man-on-the-street community.
Enter, Gabriel DeSanti.
Gabriel is on a mission to create “the world’s largest resume” through highlighting fascinating humans across the world while showcasing their jobs to his audience.
What might at first seem like another quirky content series on some “get viral quick” scheme, Gabriel’s mission runs deeper than that - He is genuinely curious to explore the world of work and showcase the types of opportunities that may exist for folks like himself who may not have pursued a traditional education to workforce pipeline.
Gabriel and I used our high-speed, encrypted Brooklyn internet to link and discuss:
World’s Largest Resume
Power of publishing on LinkedIn
Man-on-the-street content in 2025
Exclusive look into his next venture
And more!
Neil: Before we get into your background and content, what’s your take on man-on-the-street creators in 2025 given the proliferation of the format?
Gabriel: Oh man, I think as long as you're telling a story in your unique way and voice, it's great. It's a format that's working and expanding, and we're seeing more people pop up. It's funny because we were all kind of friends and started around the same time—especially the New York group. We really supported each other in that effort. As long as someone coming in now is telling their own story and not just copying someone else, I think it's great.
Neil: Two follow ups: First, who were you friends with? And then second, do you actually see younger kids in the streets? Is there a second wave coming?
Gabriel: Go to Washington Square Park—everyone has a tiny microphone, interviewing someone, I swear [laughter]. My buddy Caleb Simpson is the one I really started this with, and also Dan Churchill.
Neil: I just know Caleb through Timm Chiusano, but love that you all are in the mix. Caleb does the house content, right?
Gabriel: Of course, Caleb does the house tours. Around the same time, we were talking to Dan Churchill. He doesn’t do this series anymore, but he used to stop people and ask how much they spent on groceries. Then he’d ask to cook them a meal in their kitchen. He’d go to their house and whip up a meal with whatever was in their fridge. If there wasn’t much in there, it became a challenge—he had to get creative with what they had.
Neil: That's so savvy. So you all actually came up together, learned from each other and remained friends?
Gabriel: Yep, remain really close. Caleb's one of my best friends, and I see him the most out of anybody.
Neil: I love this. You’re known for trying to build the “world's largest resume.” Can you explain that tagline?
Gabriel: I try people’s jobs for a day. I go to work with them and see what it’s like. The real mission behind the series is, yes, I’m building the world’s longest resume—but what that really means is helping people make better informed decisions about their careers. If I can educate someone on what an industry looks like—whether it’s introducing them to a job they didn’t know existed or helping them realize it’s not for them—that’s valuable. Both outcomes benefit the viewer. That’s the mission behind the videos.
Neil: I've never heard you explain that. It's so wholesome, much more background than “Oh, some sick viral video online.”
Gabriel: It’s deep. A layer beyond all of this is that I went to trade school in high school. There, you had to try all the trades before choosing one. Looking back, that was the early inspiration—10+ years ago—for what I’m doing now. I remember thinking, I wish I could do everyone’s job, and it’s wild to see that come full circle.
I wish everyone could have that kind of experience. You learn what you like—but more importantly, what you don’t like. That hands-on exposure was invaluable for my career. It helped me move faster, because I could try different things and rule out what wasn’t right. A lot of finding what I wanted came from running from what I didn’t want.
Neil: Similarly, I feel like it's so important to understand what jobs are out there and exist. I remember graduating college applying for like “Director of XYZ” with no experience, and didn't realize why my applications weren't working. And that's the advice I try to give a lot of students that reach out.
Platform wise, I know Instagram and TikTok continue to perform well, but your goal also extends to your personal LinkedIn, where you document each job. Tell me more about this.
Gabriel: I love being on LinkedIn. It’s becoming more normal now with the rollout of new features, especially video, but it’s always been perfect for my content. I make videos about people’s jobs across different industries—and LinkedIn is the job platform. It’s the ideal place to highlight people and their careers, and to educate an audience in a way they haven’t typically seen on that platform.
For me, it’s not just about getting views. It’s about reaching a new audience, and that’s what excites me. LinkedIn offers access to a completely different group of people I don’t see anywhere else.
Neil: That's cool. But then you even add the jobs to your own resume, which I didn't even know until yesterday when I popped over. That is such a macro-level marketing play. Like you're not even making a video about that. No one else might even see this. It's a little Easter Egg.
Gabriel: I love it. I have on my LinkedIn that I worked at the NHL—which I think is hilarious. I also listed that I was the Mayor of New York, and it even had the official logo, because it pulls from the company’s auto-generated data [laughter]. I literally list every job I’ve ever worked on my LinkedIn so people can track the journey. I actually need to update it—I think I have to add 30 or 40 more positions.
Neil: I know in a recent interview with #paid that you skirted this question - but you must have a couple videos/people/jobs that are your favorite or most memorable?
Gabriel: One of my most memorable videos is the taxi driver story. Sometimes you walk into a situation thinking it’ll go one way, but the person you meet takes you on their own journey—and then the internet takes it even further.
The video with Billy, a taxi driver, is a perfect example. I never know what I’m walking into, and I definitely didn’t expect the story he shared. Billy told me how he used to work the night shift at the restaurant in the World Trade Center. On the morning of 9/11, he was asleep—but he had been at work just hours earlier. After the towers fell, he lost his job and started driving a cab. He’s been doing it ever since.
He told me that story almost in passing, but it hit me hard. It gave so much depth to who he is and why he does what he does. I knew I had to include it. When the video went out, people embraced it. The response was overwhelming.
The new World Trade Center saw it and reached out, asking if I was still in contact with Billy. They wanted to invite both of us to dinner. I called Billy and asked if he was open to a surprise—he said yes. So we went back together. He hadn’t been there since 9/11. It was emotional. He brought his girlfriend, and during dinner, he cried—I cried because he cried. It was a really special moment that only happened because we told his story.
That video means so much to me—not because being a taxi driver is glamorous, because it’s not. It’s tough, long hours, a grind. But the story, the world’s reaction, and what it led to for Billy—that’s what made it unforgettable.
It’s happened a few times now. I can try to predict which videos might go viral, but in the end, the world decides. And that’s what makes it special.
Neil: Wow, incredible. Appreciate you sharing - Real humans, real stories. I think particularly in New York City, where there are so many people, so many tales, so many stories.
Speaking of NYC, your collaborations with NYC Gov featuring “Rat Czar” and Mounted Sergeant (below) were amazing and received so well on social - How did this connection arise?
Gabriel: Very early on—probably three months into starting the series, and I’ve been doing this for about two and a half years now—I got an email from NYC Gov. It was from this amazing girl named Avery. She’s still there. I think she started as an intern, and now she’s pretty much running the show.
Avery’s a total superstar—just wants to tell cool stories. She really believes in storytelling through politics and connecting with the next generation. For her, it’s about helping young people understand why they should care and get involved. So she’s always looking for creative ways to make that happen.
Three months in, she reached out and asked, “Do you want to go to work with the Mayor?” I was like, Absolutely. Who wouldn’t want to be the Mayor of New York City for a day? That’s a great addition to the world’s longest resume.
It actually took about a year and a half for that to happen, but in the meantime, we started checking off other boxes—like going to work with the “Rat Czar,” the Mounted Unit, and the Mayor’s photographer. I didn’t know this, but by law, the Mayor’s photographer has to document everything the Mayor does. That blew my mind.
So, yeah, NYC Gov reached out, and it’s turned into a really great partnership. The videos themselves aren’t necessarily political, but do aim to be informative, like the rest of my content. But what they do is get me into rooms I couldn’t access on my own. For example, the Department of Sanitation turned me down three times. But because NYC Gov wanted the video, they made it happen.
It’s a win-win. I get to tell stories people want to watch, and they get to reach an audience in a new, authentic way. There’s real mutual benefit.
Neil: As it relates more broadly to brand partnership, brand collaboration. How are you viewing those nowadays?
Gabriel: Honestly, because of my format—and I stick to it—I have so much fun with what I do. I put myself in rooms and shoes I’d never be in otherwise, whether it’s through a brand partnership or not. But a lot of times, those partnerships help amplify the experience even more.
Take the NHL, for example. I’ve been on the ice twice now—once during a live game. The stakes were high, and you guys just threw me in there. In what other world would I get to do that? [laughter]
Getting to work with brands like that helps me keep telling these stories, which is what really matters. Brand partnerships are essential to the core of what we’re doing because they keep it going. And I genuinely enjoy them. I say yes to the ones I believe in—because I think they’re great stories to tell.
Neil: Is there anything you wish brands would think through more in advance, before they reach out or they pitch you?
Gabriel: A lot of times, there’s this groupthink where people say, “We know we want Gabe,” but they’re not exactly sure what I’m going to do. The NHL was very specific—“Gabe is going to go do this job”—and I was like, Yeah, that’s awesome.
But honestly, I don’t think that groupthink is a bad thing. Even if they’re unsure, I can often bring a perspective they hadn’t considered. That’s part of the value.
Neil: Are you opposed to brands selecting the individuals? Is that not preferred, or is that okay? Because a brand could want to highlight xyz employees.
Gabriel: I do have deals where the brand is specific about who they want me to go to work with. That usually comes with some minor back and forths, but at the core, if it’s a great story, I’m usually aligned.
Neil: I know other creators who remain steadfast that they must choose an actual, random civilian. For a brand, I think that can be scary to say, “alright, Gabe, you're just gonna go pick anyone out there.” You can see both sides.
Gabriel: I think if you’ve been doing this long enough, you get to a point where you just want to create the kind of content you’d make regardless of whether a brand is involved. The mindset is: If I had unlimited resources and full access, this is the video I’d make. That’s what we aim for—because we know that approach works and so thats kind of how we pitch.
But every brand has its own guidelines, legal considerations, and layers of approval. There are a lot of cooks in the kitchen. Sometimes, creative freedom has to be sacrificed to support the financial sustainability of what we’re doing. It’s not necessarily a bad thing—it’s just a balance we’re constantly navigating.
Neil: Good perspective. What's the future look like for Gabe? Any goals, milestones, big dreams?
Gabriel: I’m two and a half years in, and I still wake up excited to do this every single day. I’m doubling down as the job guy, and that’s not stopping anytime soon.
My dream—like I said from the beginning—is to help people make better informed decisions around their careers. That’s why I’m working on a startup called Staj—spelled S-T-A-J. It’s a job shadowing marketplace that lets people explore different industries through hands-on experience.
I want to give people the chance to see what a job actually looks like. That’s my legacy project—something I’ll be working on for a long time. And it’s launching in about a month.
Neil: Wow, that's super impressive. I don't even know about it.
Gabriel: No one knows! No one knows. But it's time to talk about it.
Neil: Our millions of readers are about to find out. Are there other people in this space? I've never even considered that as a formal function.
Gabriel: It doesn’t exist—so we’re trying to build something entirely new, and that comes with its own set of challenges. There are platforms that connect you to mentors or let you book calls with experts for advice, but nothing outside of a formal internship or trade schools that lets you actually experience different jobs.
With Staj, the idea is to offer short-term job shadowing—just one day or even a half day. You could shadow seven different roles in a week if you wanted to. It’s about giving people a real taste of different careers without having to fully commit. That kind of access just isn’t available anywhere else right now.
Neil: Sounds like the perfect opportunity to combine your passions and interests.
Gabriel: My videos are the engine—my baby. In my funnel, the most important thing is waking up tomorrow and making the next video. That’s what keeps my world spinning.
But what I keep seeing from the community is this sentiment of “Wow, that’s my dream job” or “How do I even get into that?”—no matter what job I’m showcasing that day. That kind of feedback, paired with my own experience in trade school, is what sparked the idea for Staj.
That’s the dream: to bring this to life and give people real access to explore careers in a way that hasn’t existed before.