Founder's Story - He Tried Hundreds of Jobs So You Don’t Waste 10 Years in the Wrong One | Ep. 333 with Gabriel DeSanti Content Creator & Founder of Staj

Episode Date: March 31, 2026

Daniel Robbins sits down with Gabriel DeSanti to explore what happens when content creation becomes a real career engine and a real impact engine. Gabriel explains how he finds jobs through simple DMs, why the series highlights unsung workers more than it highlights him, and how international episodes changed his perspective on poverty, environmental damage, and craft. He also shares the business reality of being a creator, where most revenue comes from brand partnerships, and why he’s building Staj as the next chapter: a job shadowing marketplace that helps people try industries in real life, not just read about them online. Key Discussion Points Gabriel describes his most extreme episode, decluttering a hoarding apartment with millions of roaches, wearing a hazmat suit, goggles, and a respirator while roaches fell on his head. He explains the show is narrated through the worker’s story, designed to give pride to people doing difficult jobs every day, not just to entertain. Gabriel shares his long runway to “overnight success,” starting with gaming videos at thirteen, then years working for YouTubers across thirty countries, before finding his own voice. He breaks down how he lands episodes, usually by searching for workers already comfortable on camera and sending a cold DM to set up a shoot. A standout moment comes from the Philippines, where a basket weaver named Jocelyn inspired massive audience support that helped buy out her inventory and materially improve her family’s life. Gabriel explains creator income realities, where only a small percentage clear six figures, and short form creators rely heavily on brand deals because platform payouts are small. He introduces Staj, a job shadowing marketplace inspired by his trade school rotations, designed to help people test a career path through real experiences. Takeaways Some of the hardest jobs are invisible, and the quickest way to build empathy is to step into someone else’s work for one day and feel what they feel. Finding your creator voice often starts with imitation, but traction comes when the content becomes uniquely you, rooted in your real interests and lived experiences. Brand deal income is seasonal, and creators who do not budget for slower months risk panicking and quitting right before the flywheel kicks in. The best creator businesses do not chase random products, they solve the exact problem the audience keeps asking about, which is why Staj maps directly to Gabriel’s core content. Delusional optimism is an edge, because most people quit during the long stretch when nothing works, but the ones who keep going eventually compound skill, audience, and opportunity. Closing Thoughts This episode is a reminder that careers are not chosen in one moment, they are tested, iterated, and built through lived experience. Gabriel DeSanti is turning that idea into a movement by making jobs visible, human, and accessible, and by building Staj to give people a shortcut to clarity. If you feel stuck, this conversation might be the push to try something real before you commit another year to the wrong path. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

So Gabriel, you are doing something that I always dreamed of doing. You're creating the world's longest resume. And I remember watching dirty jobs as a kid that show. And I always thought like, it'd be so cool to like document yourself just getting jobs and just the whole process. And then when I saw your content, I'm like, this guy is doing it in real life. Like what a time to be alive where you could do that on the internet for social. media and like that can be your life so what is the craziest most unique story or job that you had that stands out oh man a crazy one that that stands out to me is a declutterer or like kind of like a hoarding house cleaner situation so there's this woman um here in new york and she goes and she cleans these apartments and homes that are just in really bad shape. You know, often there's, oftentimes there's trash in every room, you know, up to the wall. You can't even barely open the door. And I went to work with her in one of these rooms in the Bronx or in one of these apartments

in the Bronx. It was a studio apartment. So, you know, we can imagine like it feels like a really tight space. And then with trash halfway up the wall everywhere, it feels pretty claustrophobic. And this was a pretty extreme case. And it's the one that like stands out to me the most because I had to put on like a hazmat suit. I had to wear the goggles. I had to wear a whole respirator mask.

And the most startling part was there was like millions of roaches. So there's like roaches climbing everywhere all over the bed, all over the trash, all over the walls are like falling on our head. And it was pretty insane. Like I knew what I was signing up for, but I didn't necessarily know the extent of it. And that's one that definitely stand out to me in my head. That's insane. Like the crazy part is somebody lived in there without hazmat and stuff, which is insane. So when you're doing this, it kind of reminds you, you remember undercover boss where they're like undercover, then the whole story is around the employee.

Are you finding the same thing as you're doing these jobs? Like there's this whole story around the person that you get to experience this with? Absolutely. Like the videos, they are like a little bit about me and my experience trying the job, but it's also very much like narrated through the voice of this person that I'm joining at work. And my hope is like to give pride to like what these individuals are doing as well because they're really the ones who are showing up and doing this every single day. And you know, they're the unsung heroes oftentimes. So yeah, it is it is a combination of me trying it and highlighting this wonderful person who who shows up and does it. every day. I have to say a lot of people would watch. I think almost everyone in their 20s wants to be a

content creator, maybe like even 30s and below. They want to be content creator. And they're seeing, you've been doing this for a few years, correct? I think 2022 is when you started. Yeah, yeah. So I started this show. Yeah. So you started this show about, you know, four years ago, less than four years ago. That's incredible to get the traction to be able to do this like you're doing. what you think really got you to the point where you're like, okay, this is my full-time thing. I'm going all in. Absolutely.

So really before starting the show, there was about a decade of experimentation in content creation. So I started making gaming videos when I was 13 years old. And that was like my introduction to making content. And back then, like making YouTube videos or making gaming videos, like it wasn't, it didn't have the same weight that it does now. And it was just, I just started doing it because I was genuinely curious about it and interested and was having fun with my friends online.

And then over time, that transformed from gaming content to picking up a camera. And it felt like this similar process, just a different tool. And that's really like when I fell even more in love with it and was like, I want to do this. Like this is, this is kind of for me. And so over time, I was just working for different YouTube. helping them make their content. There's about six years of working for different YouTubers, traveling to 30 countries around the world,

helping them make videos. And so through all of this process, I'm learning how to do this for myself, knowing that one day I'm going to step into those shoes myself. And also at the same time, creating content of my own and experimenting, nothing is hitting, that's for sure,

partly due to the fact I think that I didn't know what my voice was yet. I was like making these videos or like making travel videos for myself for making little vlogs. But like I didn't know my through line or I didn't know like the real purpose behind the content that I was making. So yeah, there was just years and years of experimentation before I got to building the world's longest resume or going to work with people and making this content. And I think once I started doing that, it was like it worked pretty quickly. And I think that's partly due to the fact that I was making videos that were like just me, uniquely me and

like uniquely my voice and things that I'm interested in. And there's like odes to my past in there. And I think that that's why it worked. You know, there was a mistake I made for a while. I was like, okay, I want to become, I want to be like Diary of a CEO. Like that, that's like, I would strive to have a show like that. But then I formulated everything as if I am Stephen Barlett and dire of a CEO, which like, like you said, it's not my voice. And it became unnatural. It was almost uncomfortable because it's like, I'm trying to be something that I'm not. And what I noticed, there was more traction when I'm like, what's the differentiator is me? It's my personality. But it's really hard to ideate how to be

different. So obviously what you're doing is so unique and different. How did you get to the phase where you're like, okay, I'm going to, I'm going to do this because it's so different. It's so unique and then you obviously had to start yeah i mean just like what you said like when you set off and started or whatever part of the process that was you were imitating somebody else that you know was doing a really great job and i think that that's very similar for anyone who maybe find success in their in their path like i started off imitating my idols you know there's there's lots of early influence from uh the people that i worked with and the people that i watched online because that's that's all I knew. And so you go off and you try to imitate them and, you know, put that out and you learn

through that process. And then you're like, oh, like, I like this part of it. I don't like this part of it. And then over the years and over time, it morphs into you and your unique thing. And I think that's, you know, how I maybe found my style. But then in terms of the actual like topic of the subjects being like going to work with people and deciding to make videos about jobs. That's kind of a unique experience to me. So early in my life in high school, I went to a trade school. And in trade school, you have to go through all the different trades and try all the different trades before you pick the one you're going to get certified in. And during this process, I remember thinking like, oh, like, I wish I could just continue to work everyone else's job. I was just having so much fun getting access and exposure

during to all these different industries. And that thought really stuck with me for the better part of like a decade. And during this period of time where I was experimenting with content, trying to figure out who I was, it popped back into my head. And I was like, what if I really did, like, try other people's jobs?

And so that's kind of like how it came to be. So how do you go about trying jobs now? Like, do you call people and say, hey, I want to try your, like, I want to try your job. job and then they're like hang up the phone or you have to like where i always wonder when i watch your videos does the company do they have to approve it like how to what's the i imagine there could be a complex process with being able to like work you know follow someone around you have cameras

there that whole process there it's it's way simpler than i think a lot of people imagine and often starts with me just dmming somebody i use the internet to my advantage in this way so i'll think of a job or I'll be in a conversation with someone and they're like, have you ever done a plumber before? You know, and I'm like, oh, no, I've never done a plumber. Like, let me find one. And so I'll go on TikTok or YouTube shorts or Instagram and depending on the location, I'll type in like New York City plumber and I'll find someone who's making videos about their career. And in this way, even if they have no following, which is usually like better, I know that this person is comfortable being on camera. I know that they either are maybe trying to get a little exposure for their business or they're

trying to educate an audience on why their industry is important. And so I find that those people are really great candidates to be on an episode. And that's like really where I start. And if I can't find someone in that way, then I like go outside and I start like researching or like going through my external network trying to find like someone who works in a specific position. But really it just like starts with a cold DM. Isn't it crazy how connected? I was thinking about this this morning. I messaged somebody on LinkedIn and I was like, I can't believe I message this person on LinkedIn. If it was 20 years ago, there would be no way I can get a whole. Like nobody would allow me get in touch with this person, right? There's always some sort of gatekeeper somewhere.

But the fact that you could just DM somebody and you get in, I mean, what a time is, tell me about an experience that you've had outside the U.S. because obviously, obviously, Obviously, there's really unique jobs in the U.S., but what about outside the U.S.? What is a really fascinating experience you had? So I went to, man, there's so many. So far, I've been to the Philippines, India, Indonesia, and Mexico. So those are like the international episodes that I've been able to film. And I've had so many great experiences like through all of those.

One that really sticks out to me is in Indonesia. I went to work cleaning some of the dirtiest rivers in the world. and we were like in the rivers every day you know water up to here you're in a wet suit you got the boots on you got the gloves on and you're just like cleaning trash and it's like this this experience like in my memory to this it goes way beyond like just making a video it goes like into impact and like you know we know that there's a trash problem we know that there's plastic problems but until you like are actually there and like can experience it for yourself i don't think most people understand the depth of the problem.

And so that's just like an episode that really stands out to me because I was able to put myself in a place where it was just very eye-opening. And I was excited to try to bring more awareness to that cause through that video, which it did. It did really well. Yeah, we live in a bubble in a sense that you don't know really what happens outside the bubble until you travel, which is why I love to. travel. Let's talk about the Philippines because that has a special place in my heart. I frequent

to the Philippines. What was one of the jobs there? Yeah. So the job that is it doesn't just live in my head. It lives in my heart is with a basket weaver. Her name's Jocelyn and she weeds products out of local grass, Benig. I think it's pronounced Benig. And she works in a cave and it's like this local community of women who like work in this cave because it's a natural like temperature. It just neutralizes the temperature throughout colder times or warmer times. It just kind of like stays, you know, a very similar temperature. So they weave these products in this cave. And, you know, a part of what I ask people is how much money they make just to bring awareness

to what you can make in all these industries and in these places. and she made significantly less than we had expected. And like, it's backbreaking work. Like you're sitting like crouched over every day. You're working with your hands, with your feet, and you're just making products for 10 plus hours a day. And they take ages to make. And it's very intricate and it's an art and it's beautiful.

So I did this video with this woman Jocelyn, and we gave her some money. and it was very like heartfelt. And then we put it out for the world to see. And then it took on just an entirely new life of its own. And like the world like accepted her with like open arms. And we raised a bunch of money for her. And we were able to buy out her entire inventory of product.

And then also like plus additional like thousands of dollars on top of it to help her and her family. and she just had a son. She has a little son, and I believe she just had another child recently. They were able to like, just buy like basic things that they needed. You know, like they bought a refrigerator and they were able to like put a wall on their kitchen so their kitchen wasn't outside. And it was just, it's a very touching story. And like being able to facilitate that, whether that was intentionally, not intentionally, like,

the fact that that was able to come to fruition, like, that's like a dream. That's a dream come true. And so that's a story from the Philippines that like, just like, you know, lives right here. I love that. I need to check out these baskets when I'm there. When you, what's the emotions that go over you when you watch a video like this? You see what happens based on the reactions. And then you realize that you're also living out your dream of being a content creator.

a video creator. So you're living out your dream. You're doing what you're most passionate about. You're helping somebody bring awareness. And that awareness is also impacting them maybe for the rest of their life. What emotions when you think about that? Like it's the coolest thing in the world. And it's so special because it's like, this is like, this is what I want. This is everything I've always wanted. And I get to wake up and do this. And I'm like just so privileged to have that opportunity to do that and then hopefully help other people along the way. It's a it's a dream and like sometimes it feels like that, you know, but it still feels like that. What am I saying? Like, yeah, it's the coolest thing in the world. So you brought up something earlier about I, it's so

interesting how you do ask people how much they make, right? I love, because normally when people are doing that in shows, it's always like people doing things and they're making millions or billions of dollars, right? Like, when is the first, how old are you? How old are you? when you made your first million, right? Like all those shows, right? So it's good to see, like, reality of most people, not like the top 0,001%. But as content creator nowadays,

because I think a lot of platforms, unfortunately, what we've seen is they pump out a lot of money in the beginning, they get everyone in it, and then they start to drop what you can make and then, you know, people need to diversify. What are like content creators? What can they make nowadays? Yeah, absolutely.

It's a very, it can be very lucrative. you know, if you're doing, if you find yourself in the right place. But I think there's a statistic that came out this year that like four to six percent of only four to six percent of content creators are going to make over $100,000. So, you know, the largest portion of creators aren't going to make $100,000. I am super lucky to be in that, you know, 4% that does make over $100,000. But like that journey that there was a, for sure like a journey to get there, but it was kind of crazy how fast it did happen.

Like I went from years of freelancing for other people, you know, where I was making 40, 50,000 dollars a year. And then I was like working as a freelance director, maybe made like 50, 60,000 dollars a year. And then my first full year as a creator, I made less than that. and then in my second year, I made more than $100,000. And then I've doubled it in my third year and then hopefully we'll continue. I'm on track to do the same as I did last year, but hopefully we'll see an increase. Where are people getting paid now? Is it brand deals?

Is it from the platform? What do you think like the mixes are nowadays? It really is going to differ from like creators or creator. So like one of my best friends who I worked for and lived with for a long time. You know, he's a long-form video creator. And so he has, you know, a good chunk of money that comes in every single month from his YouTube ad sense, from people watching his videos. And at this point, his catalog is eight years old. You know, there's eight years of videos that compound on each other.

So that amount theoretically just grows and grows and grows over time. So, you know, he's making good money every month just from videos that are in his catalog. And then on top of that, he has brand partnerships. But for him, like, I believe that it's a little more even. For me, as a short form video creator, I do have a lengthy catalog of videos, but the platforms definitely don't pay as much in terms of the, you know, a dollar per thousand views. And it's, yeah, I mean, it's so insignificant. I would say, like, my monthly take home from videos is like 10%.

So the other 90% for me is coming from. brand partnerships and you know that could be a little stressful as a creator because you need to continue to line up those brand partnerships and make sure that there's you know money that is still coming in month to month and it's a little more um yeah there's just some unexpected it can be a little more unexpected so you have to make sure that it's everything is still flowing in that regard it's entrepreneurship one month you're really high next month you got zero then the other month you're 10x and then they're negative 50 it's that's a biggest that's one of the the biggest learnings that I've had is like I call it brand deal season like November

December is the best month best months of the year for I think all creators because it's when all of the advertising dollars are being spent around the holidays so it's very it could be very easy to fall into a trap of like oh my gosh like I just landed all in all this money like I'm good but then January like really like the first half of the year is a lot slower so you You have to like, my first year where I made like over 100K, I got like four months into the year and I was like, oh my gosh, like, am I going to have to go back to freelancing? You know, there was a moment where like I thought that that could happen. So I had to learn like it comes, it comes and goes and you have to make sure that it lasts

if you want this to be a lasting thing. Never said better. It comes and then it goes and then it comes back. It's a, it is the roller coaster. So let's talk about stage. is I think there's a big push right now for people that are content creators because they don't want to rely. They don't want to rely on only brand deals or partnerships and then payments from the platforms. But then they also see huge value in building something on their own that maybe they could sell exit.

Maybe they could do something with that. That might even be way bigger than all the other stuff. And you're leveraging your audience and community. What are you doing there? Yeah. So Stage is a company that I'm starting that is started. It's launched. It's public.

That is a job shadowing marketplace. And so it allows people to book a job shadowing experience in an industry that they're interested in. And it's a baby of my videos. It's from feedback that I've seen from my audience of saying like, how do I get into that industry? Like how do I even get started? How do I find a career?

How do I pivot in my career? And then it's also informed from my time in trade school. And I was like, what if I could create? that a similar experience to that's a little less formal than going to back to school. And so the idea is that you can job shadow, you know, lots of different industries on your way to finding a career or pivoting in your career. And it was what I decided to go into in terms of like a business for, for me and for my content instead of, you know, creating a physical product or merch or anything, stuff like that.

like I just had no interest in doing that. Sure, that would be way easier. I promise you, like building a business that's never been done before is way harder than making videos. But I do believe in like the long term, you know, benefits of that, both hopefully for myself and for the people who use Staj. I think the biggest mistake that people make is they create something that they think the world needs, but then the world reacts and doesn't need it.

And we see this, a lot of creators, celebrities, they come all with like a skincare brand that is not really needed. There's a million just because they slap their name on something. So it's great that you listen to the audience. You listen to the community. And then you went into something that you're known for versus like you said, if you launched a T-shirt brand or something that people don't really resonate with, it's almost like you're creating a business that your audience doesn't really want or need versus. this. I love the idea. I mean, that's awesome. I want to go. I might use it so I can film myself shadowing.

Like, I want to, I really, I really want to go through the interview process. I feel like I was the worst interviewer. Like, I was the worst interviewees. I didn't get jobs because I would like to go and, like, go to the grocery store and act like I want a job and get interviewed. And I want to see it. We can help set it up. We could help set it up.

You and I want to do a job with you. I'm very much building stage in public. and we are working on what our business model is. We offer a direct-to-consumer option, so you could go on and book a stage directly. But really, like, that's not going to be our growth model. And we need to, this year we're focusing on, like, not getting rid of that.

Like, we'll always have that option, but really we need to focus on, like, how we grow this thing. I love building in public, but I hate building in public. Do you ever have the fear, like, you're about to push the upload button or someone on your team is going to press the upload button and you're like, I don't want to do that. I mean, always, like, always. It's hard to be vulnerable or like ask for help or put out something that's unpolished.

But over time, like I've learned that done is better than perfect. You just have to. You just have to. It moves the needle more than like being stuck in analysis paralysis. I like that done is better than perfect. Final question. So we wrote this book, my wife and I, called Unlimited Possibilities. It's about breaking through barriers that you didn't think were possible.

I imagine you've talked about a few today, but, you know, what's the first thing that stands out in your mind when you think about a barrier in your life that you were able to break through? I mean, I think I've always had like a little bit of a delusional optimism around my career and going after what I wanted. And I was, I put my mind to it. You know, I was like, there's, there's no way that this doesn't work at being a creator or whatever, whatever it was that I'm building. Like, there was no way that it wasn't going to work. It was just a matter of time. And like, how much time can I commit to it than a lack of better word, like, how long can I eat shit before, like, it works? And I was just like, I think I was just willing to do that and do whatever it took to get there.

So I think a lot of the years leading up to this was just going through those motions of it, not. working and failing over and over again failing forward like I love the the concept of failing forward and I'm probably still failing forward you know like this isn't the ultimate version of me I'm going to evolve and turn into whoever I am next so I think that like that's been kind of my my journey and something that I'm like carrying with me even now hey I like that delusional optimism you got to be a little crazy You've got to be crazy. There's like a saying, right?

Like you're crazy until it works and then you're a genius. I don't know the whole saying, but that's like the concept, which I think it's kind of like entrepreneurship in general is you think about it. Like you're giving up a guaranteed paycheck to go work somewhere. It's like I'm going to work 80 hours so I don't have to work 40 hours kind of thing. You have to be a little crazy. 100%. Because it doesn't really make any sense. It's like it's you're and you're pretty much guaranteed to fail because more people fail than succeed.

We're all a little crazy. And that's why I think I don't, I've been fired twice. I don't know if I could be an employee again. I don't know if I'd make a good employee to be honest. Yeah, I agree. I wouldn't either. And I can say that because I did have like a formal job. I was working as an entry level engineer straight when I finished trade school.

And I did that for two years. but I couldn't imagine like being an employee again like there's a lot of rigid rigidity around it and I I don't necessarily work well in that in that regard which I think is a strength and maybe a con as well but you know that's me wouldn't be where you're at if if you know so there you go so it obviously is a strength for you and for you I mean you got you got so much life ahead of you like you could do so many things I wish I think you're in your 20s right late 20s I'm 28, yeah. 20, man, at 28, I wish I was doing what you were doing.

You know, like the knowledge, what I know now, if I only knew then, you got a lot of time ahead to build so many things. But if people want to, how can they sign up for Stage? Yeah, so go stage.com is the website. Right now it's just New York based, just because that's where our network is and that's where we're kind of building this thing. And then obviously the ultimate goal is to bring this as wide as we can. So if you're in New York, you can check out Stajj. And I would love to help, you know, help you set up a job-shadowing day experience. Like I said, this year, we're offering them for free.

So it won't cost you anything if you're in New York or if you can get to New York and would be more than happy to set that up. Man, it was great having you today. Thank you. What's your ice you handle? Gabriel, period, Desanti. Gabriel DeSanti, the one and only. Thank you again.

And I'm excited to one day go on a job with you. You got it. I'm going to think that happened with you. You got to come. Maybe I'll bring you undercover at the hotel. Undercover boss. There you go. Thanks, Gabriel.

It's your time. Of course.