← Founder's Story
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
00:27:43
Daniel Robbins talks with creator Gabriel DeSanti, who’s building the world’s longest resume by job shadowing real workers and documenting what careers actually look like. Gabriel shares the most intense job he’s done, cleaning a hoarding apartment in a hazmat suit while roaches fell from the ceiling, and explains why the series is really about the people behind the work. They also break down how he built his voice after a decade of experimentation, why brand deal income is a roller coaster, and how his new startup Staj turns job shadowing into a marketplace so anyone can test a career before committing years to it.
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- [00:01]
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- [00:30]
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- [01:09]
Interviewer
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 joke job that you had that stands out?
- [01:48]
Gabriel Desanti
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 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. Often times there's trash in every room, you know, up to the wall. You can't even barely open the door. And I, I went to work with her in. 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, you 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 respir 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. I knew what I was signing up for, but I didn't necessarily know the extent of it. And so that was that. That's one that definitely stands out to me in my head.
- [03:08]
Interviewer
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, and it kind of reminds me of, 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 a. This whole story around the person that you're ex. You get to experience this with?
- [03:31]
Gabriel Desanti
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 this every day.
- [04:02]
Interviewer
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.
- [04:16]
Gabriel Desanti
Yeah, yeah. So I think I started this show.
- [04:19]
Interviewer
Yeah, 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. Yeah. You think? Really got you to the point where you're like, okay, this is my full time thing. I'm going all in.
- [04:36]
Gabriel Desanti
Absolutely. So really, before starting the show, there's 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 kind of for me. And so over time, I was just working for different YouTubers, 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, you know, how to do this for myself, knowing that one day I'm gonna, like, step into those shoes myself. And, you know, 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 or 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 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. And I. I think that that's why it worked.
- [06:40]
Interviewer
No, 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. I would strive to have a show like that. But then I formulated everything as if I am Stephen Barlett and Diary of a CEO, which, like you said, it's not my voice. And it became unnatural, and 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. Is me. It's my. My personality. But it's really hard to ideate how to be different. So you 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.
- [07:27]
Gabriel Desanti
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 finds success in their. In their path. Like, I started off imitating my idols. You know, there's. There's lots of early influence from 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. Like, I was just having so much fun getting access and exposure into 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.
- [09:11]
Interviewer
So how do you go about trying jobs now? Like, do you call people and say, hey, I want to try you? Like, I want to try your job. And then they're like, hang up the phone. Or you have to, like, I always wonder when I watch your videos, does the company. Do they have to approve it? Like, how. 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.
- [09:36]
Gabriel Desanti
It's. It's way simpler than I think a lot of people imagine. And often starts with me just DMing 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 never done a plumber. Like, let me find one. And so I'll go on TikTok or YouTube shorts or Instagram, and I'll, 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.
- [10:44]
Interviewer
Isn't it crazy how connected I was thinking about this this morning? I. I messaged somebody on LinkedIn and I was like, I can't believe I messaged this person on LinkedIn. If it was 20 years ago, there'd be no way I can get a hold. Like, nobody would allow me to 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. What a time is. Tell me about an experience that you've had outside the U.S. because obviously there's really unique jobs in the U.S. but what. What about outside the U.S. what. What is a really fascinating experience you had?
- [11:20]
Gabriel Desanti
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 wetsuit, 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 like 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, through that video, which it did. It did really, it did really well.
- [12:29]
Interviewer
Yeah, it's, it's weird. 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 frequently. To the Philippines. What was one of the jobs there?
- [12:45]
Gabriel Desanti
Yeah, so the, the job that is it, it doesn't just live in my head, it lives in my heart is with a basket weaver. Her name's Jocelyn and she weaves products out of local grass. Beni, I think it's pronounced Beni. And she works in a cave. And it's, 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, 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 back breaking work. Like you're, you're like sitting like crouched over every day. You're working with your hands, with your feet and, and you're just making products for 10 plus hours a day. And they take ages to make and they're, it's very intricate and it's, it's, it's an art and it's beautiful. So I did this, this video with this woman, Jocelyn, and, and we, 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, just 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. That's a story from the.
- [15:11]
Interviewer
This is Mike Bolo of Lexicon Valley, and I'm Bob Garfield. Are you one of those people who sometimes uses words? Do you communicate or acquire information with, you know, language? Hey, us too. So join us on Lexicon Valley to
- [15:28]
Gabriel Desanti
true over the history, culture and many
- [15:30]
Interviewer
mysteries of English, plus some rice cracks. Find us on one of those apps where people listen to podcasts.
- [15:39]
Gabriel Desanti
Philippines that like, just, like, you know, lives right here.
- [15:42]
Interviewer
I love that I need to check out these baskets when I'm there. When you. What's the emotions that. 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, video creator. So you're living out your dream. You're doing what you are 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
- [16:16]
Gabriel Desanti
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.
- [16:41]
Interviewer
So you brought up something earlier about I. It's so interesting how you do ask people how much they make. Right. I love that 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's the first, 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.001%, but as a content creator nowadays. Because I think a lot of platforms, unfortunately what we've seen is they do, 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, what are like content creators? What can they make nowadays?
- [17:25]
Gabriel Desanti
Yeah, absolutely. It's a very, it could be very lucrative, you know, if you're, 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 4 to 6% of only 4 to 6% of content creators are going to make over $100,000. So you know, the largest portion of creators aren't going to make a hundred thousand dollars. I am super lucky to be in that, you know, 4% that does make over a hundred thousand dollars. But like that journey that there was 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 a year and then I was like working as a freelance director, maybe made like 50, 60 thousand 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 a hundred thousand dollars and then I've, I doubled it in my third year and then hopefully will, you know, continue. I'm on track to do the same as I did last year, but hopefully we'll see an increase.
- [18:38]
Interviewer
Where are people getting paid now? Is it brand deals? Is it from the platform? What do you think, like the mixes are nowadays?
- [18:45]
Gabriel Desanti
It really is going to differ from like creators or creator. So like my, one of my best friends who I worked for and lived with 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 AdSense 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, you know, a lengthy catalog of videos, but the platforms definitely don't pay as much in terms of the, you know, dollar per thousand views. And it's. Yeah, I mean it's, 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 can 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, 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.
- [20:12]
Interviewer
One month you're really high, next month you got zero. Then the other month you're 10x and then negative 50.
- [20:19]
Gabriel Desanti
It's, that's a biggest, that's one of 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 have to like my first year where I made like over 100k, I got like 4 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, 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.
- [21:09]
Interviewer
Never said better. It comes and then it goes and then it comes back. It's, it is the roller coaster. So let's talk about stage is. I think there's, there's a big push right now for people that are content creators because they don't want to like, they don't want to rely on only brand deals or partnerships and then, you know, payments from, 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?
- [21:46]
Gabriel Desanti
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, A little less formal than going 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, in doing that.
- [22:49]
Alex Canceroitz
Sure.
- [22:50]
Gabriel Desanti
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, I do believe in like the long term, you know, benefits of that, both hopefully for myself and for the people who use Stash.
- [23:06]
Interviewer
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 out with like a skincare brand that is not really needed. There's a million just because they think 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 you know, something that you people don't really resonate with. It's almost like you're, you're, you're creating a business that your audience doesn't really want or need.
- [23:44]
Gabriel Desanti
Yeah.
- [23:44]
Interviewer
Versus this. I love the idea that, I mean, that's awesome. I got, I want to go, thank you. I might use it so I can film myself shadowing. Like I want, I really want to go through the interview process. I feel like I want to. 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. Yeah. And I want to see help set it up.
- [24:08]
Gabriel Desanti
We could help set it up, you
- [24:10]
Interviewer
and I. I want to do a job with you.
- [24:12]
Gabriel Desanti
I'm very much building stage in public. And we are working on, like, what our business model is. Like, we offer a direct to consumer option. So, like, 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.
- [24:37]
Interviewer
I love building in public, but I hate building in public. You ever. Do you ever have the fear like you're about to push the upload button or who is someone on your team is going to press the upload button and you're like, I don't want to do that.
- [24:51]
Gabriel Desanti
I mean, always, like, always, it's. It's hard to be vulnerable or like, ask for help or put out something that's unpolished. But I, 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.
- [25:09]
Interviewer
I like that done is better than perfect. Final question. So I wrote. 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?
- [25:30]
Gabriel Desanti
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 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 that a lack of. Better word, like, how. How long can I eat shit before, like, it works? And I was just like, think I was just willing to do that and do whatever it took to. To get there. So I think a lot of the years leading up to this was go. Just going through those motions of, 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.
- [26:35]
Interviewer
Hey, I like that delusional optimism.
- [26:39]
Gabriel Desanti
You gotta be a little crazy.
- [26:42]
Interviewer
You gotta 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, you know, that's like the concept, which I think is 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 gonna work 80 hours so I don't have to work 40 hours kind of thing. Like, you have to be a little crazy 100% because it doesn't really make any sense. 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.
- [27:26]
Gabriel Desanti
Like, I. Yeah, I agree. I wouldn't either. And I, I can say that because I did have like a formal job. I was working as an entry level engineer, straight, when I finish trade school, and I did that for two years. But I couldn't imagine, like, being an employee again. Like, it, 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.
- [27:54]
Interviewer
Wouldn't be where you're at if, if you don't. 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. I wish. I think you're in your 20s, right? Late 20s.
- [28:08]
Gabriel Desanti
I'm 28.
- [28:09]
Interviewer
Yeah, 28, 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. Yeah, A lot of time ahead to build so many things. But if People want to. How can they sign up for Stage?
- [28:23]
Gabriel Desanti
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 Stash 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.
- [28:52]
Interviewer
Man, it was great having you today.
- [28:54]
Gabriel Desanti
Thank you so much.
- [28:55]
Interviewer
What's your IG handle, Gabriel, Period.
- [28:57]
Gabriel Desanti
Desanti.
- [28:59]
Interviewer
Gabriel Desanti, the one and only. Thank you again. And I'm excited to one day go on a job with you. I'm.
- [29:05]
Gabriel Desanti
You got it. You gotta come. Maybe I'll bring you undercover at the hotel.
- [29:11]
Interviewer
Undercover Boss. There you go. Thanks, Gabriel. Thanks for your time.
- [29:16]
Alex Canceroitz
Hi, this is Alex Canceroitz. I'm the host of Big Technology Podcast, a longtime reporter and an on air contributor to cnbc. And if you're like me, you're trying to figure out how artificial intelligence is changing the business world and our lives. So each week on Big Technology, I bring on key actors from companies building AI tech and outsiders trying to influence it, asking where this is all going. They come from places like Nvidia, Microsoft, Amazon, and plenty more. So if you want to be smart with your wallet, your career choices, in meetings with your colleagues and at dinner parties, listen to Big Technology Podcast or you get your podcasts.
- [29:52]
Interviewer
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