Creators On The Rise: Ross Pomerantz on becoming the corporate bro

By 08/23/2023
Creators On The Rise: Ross Pomerantz on becoming the corporate bro

Welcome to Creators on the Rise, where we find and profile breakout creators who are in the midst of extraordinary growth. Today’s installment is brought to you by VidSummit.

You know that scene in the The Simpsons where Homer’s horrible boss pins up that sign: Don’t forget, you’re here forever.

Ross Pomerantz has a sign like that. It says, Sales Are Dope Never Ever Stop Selling.


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Pomerantz didn’t originally set out to be a salesman, but when he ended up in tech sales, he realized something. Salespeople have it rough.

Everybody in sales, it started to resonate. People were like, it doesn’t matter, the culture, the industry, I’ve spoken to teams in South America, Europe, Africa, everybody complains about the same thing,” he says. “Their quota is too high. Their product sucks. They’re not making enough money, and their marketing team is trash. It doesn’t matter what language they speak, which is wild, and so it started to rise and become this thing.”

That “thing” would coalesce into Corporate Bro, Pomerantz’s online persona, through which he makes and stars in satirical videos that simultaneously poke fun at and empathize with the millions upon millions of salespeople who make the world’s industries go round.

Pomerantz has had his eye on videos for a while. He started making them “purely out of catharsis” back in the days of Vine (RIP). He was in tech sales for a decade, making videos on the side, but he knew he wanted to do more. He went to Stanford, and knew coming out of his time there that he wanted to commit fully–not just to short-form videos, but to a longer-form project.

It was a risk. He’d seen lots of other people in sales or consulting who decided they wanted to break out and do something more creative. “They would do it and then they would, at the end, be like, ‘You know what? I’m just going to go back into consulting or banking,’ or whatever soul-sucking mindless job they want to do,” he says. “I was like, ‘I’m not going to do that.’ I know I came here to elevate the business side and do something bigger and better in business but what better to do than start my own, do my own thing and see what happens.”

He committed to Corporate Bro full-time, and also committed to the long-form project he’d wanted to work on for years. It’s called Sales Are Dope (S.A.D. for short), it has eight episodes out on YouTube, and it’s the pilot for what Pomerantz hopes could eventually be a network or streaming show.

We’ll let him tell you the rest below.

This interview has been edited for length and clarity.

Tubefilter: I’m familiar with you and with your videos, but I would love to hear about your background for people who maybe don’t know you.

Ross Pomerantz: I’m from Atlanta, Georgia, originally. I moved to the Bay Area when I was in seventh grade. Everyone’s like, “Where’s your Southern accent?” Kids are pretty ruthless in seventh and eighth grade about accents. I quickly lost my accent. Y’all will come out from time to time but I don’t really speak with a Southern accent anymore. I grew up, my dad’s a journalist, writer. Taught at Emory. Currently teaches journalism at Stanford. He’s a nonfiction author, and so I think you grow up saying, “I don’t want to be anything like my parents.” I thought I was going to be a major-league baseball player. Turns out I’m 5’11. I didn’t throw hard enough. I ended up being a cross between my parents. My mom’s been in the business world and financial services for 40 years. She just retired two weeks ago. My dad’s a writer. I found myself in what we’ll call business writing. Candidly, I graduated college. I went to Occidental in L.A. with zero hard skills, as many athletes do, and didn’t know what I wanted to do and found myself in tech sales.

That’s where all the Corporate Bro things came from. I ended up at Oracle and I was like, “Oh, sick, Oracle. That sounds like a fun company. That’s Oracle Arena. That’s where the Warriors play.” It turns out Oracle is not just Oracle Arena. It is a massive, massive technology firm. Still, could hardly tell you what they do. I ended up in sales, business development they called it. I didn’t know I was getting into sales. Many people know what salespeople are. They don’t have a great opinion of them. If you’ve ever been in sales, it is a very, very soul-sucking job at times because you’re being persistent.

Tubefilter: “Sales are sadness.”

Ross Pomerantz: You’re pushing people. Sales are sadness, that’s exactly right. I started making videos. Purely out of catharsis back in the Vine days. Early days.

Tubefilter: Oh, Vine. Oh, wow.

Ross Pomerantz: Yes, I’ve been doing this for a minute now. It was a side gig. I am 34. Ugh, god.

Tubefilter: [laughs] I’m 30. We’re close. 

Ross Pomerantz: It’s fine.

Tubefilter: It’s fine!

Ross Pomerantz: Yes, exactly. I know I age myself, but people were like, “Oh, fuck, Vine. Yes, I remember Vine.” Real ones know. Made videos that turned out, for me, it was purely, again, just because sales were really tough and I was like, I looked around one day, and I was like, “How are all these 20- to 40-year-olds closing these million-dollar deals with Fortune 100 CEOs? We don’t know what the hell we’re talking about. We don’t know what we’re selling!”

Yet, here it is. It’s happening. All in this building called Twin Dolphin, which was right across the street from Oracle’s beautiful campus. You see it from the freeway. You’re like, “Wow, that must be a cool place to work.” Then the salespeople were in the shithole across the street. It was just a frat house.

Tubefilter: Oh, that’s so classic.

Ross Pomerantz: Yes, I describe it as a frat house with a dress code. I basically was in tech sales for almost 10 years, and on the side, I was doing this thing. It turned out that sales is the same across the world. A lot of people are like, “Oh, you do this niche thing.” I’m like, “It is a bit like niche but it’s the largest, oldest profession on Earth. There are probably 50 million salespeople on Earth. If you aren’t in sales, you know what sales is.”

Everybody in sales, it started to resonate. People were like, it doesn’t matter, the culture, the industry, I’ve spoken to teams in South America, Europe, Africa, everybody complains about the same thing. Their quota is too high. Their product sucks. They’re not making enough money, and their marketing team is trash. It doesn’t matter what language they speak, which is wild, and so it started to rise and become this thing.

I felt, watching Silicon Valley, which is obviously a beautiful perfect depiction of the Silicon Valley but from the engineering and founder side, I was like, “Where’s the sales team?” There were a couple of episodes where they briefly mentioned they’d play on a little bit of the trope of sales. The most common profession in Silicon Valley is sales. We’re the largest group of people. Nobody likes us, but why aren’t we talking about it? I had this dream for probably six or seven years to write this thing. I’d written different versions of it. I’m not really in the Hollywood game and so I figured I would self-finance it and try to raise money to do it myself.

That’s more or less what happened. I was going to go to Second City in Chicago. I was about to move. I got into their comedy film school there, but then, lo and behold, a miracle happened. I got into Stanford as well. So I called up Second City. I was like, “What should I do here? I’m creative. I want to be around creative people, but Stanford is also Stanford. So what?” They’re like, “Go to Stanford, you dumbass.” I was like, “Okay. All right. From the admissions director, that makes that decision pretty easy.”

It allowed me to keep working on the Corporate Bro stuff. I was close to home, which meant my crew, my friends, my family, all my unpaid labor, we could just make videos still. [laughs] That’s what basically [Second City] said. They’re like, “You could come here, but you already have a portfolio. You have an audience. That’s what people are trying to do here, so go to Stanford, do your thing.” I basically said, “If I do this, I have to do something creative.”

I became the creative director for the GSB Show, which is a big theater production. You get about 200 people involved, dancers, band, actors. You write it. It’s an original musical. Then I also shot a pilot for Corporate Bro as well while I was there. Went to L.A. for four days. It was just truly a masterclass in mediocrity. It was dogshit, to put it lightly, but it was a lesson I could only learn.

Tubefilter: The Southern came out. I heard it. The Southern came out right there.

Ross Pomerantz: [laughs] Yes. I got fired up. It was bad. It was one of those things that you can only learn by doing. It was an expensive lesson. I do a lot of speaking and I do a lot of brand deals and things like that. It’s always been just money into this account so one day I can finally shoot what I want to do. One day I can invest in the content I want to make.

That’s what happened. Two years after that shitty pilot came out, three years after it came out, I rewrote a bunch of things, changed the world a little bit, and got a legitimate production team down in L.A. It’s shot with the technical aspects that could go on Netflix tomorrow. Could go on any streamer tomorrow, from a technical standpoint. Maybe not from a writing/acting standpoint. I wanted to leave nothing on the table. If this is the only time I get to do it in my life, which hopefully it won’t be, I don’t want to leave anything on the table. It’s one of those, “We could do this. It’s going to cost a little more. We could do this.” I’m like, “I don’t care. Just do it.” I know it’s going to add up. This is the dream here. I wasn’t saving this money to buy a house. I was saving this money to shoot this thing. That’s what I did. That’s the short-form version of it. Ups and downs in there.

@corporate.bro Nice try Mr Prospect… but im not that desperate yet…. Yet. #Quota #SalesAreDope #salesrep ♬ no – kenzie !! 🤍

Tubefilter: When did you move out of sales and do this full-time?

Ross Pomerantz: I worked through my first year of business school. I was working for a virtual reality startup as one of the founding members, the sales lead there. It was cool. I was selling to sports teams. It was a brain gym software piece. It’s like if you can measure everybody physically in the NFL combined, why not measure their brain processes too? Being a former athlete, also a big video gamer and sales guy, it hit all these pieces of what I like to do. I got to be the voice inside the video game. It was like, there’s an acting piece to it.

I was watching all these people who were super educated. They’re like the median person at Stanford. Their name is Danny and they went to Yale, and then they worked at Bain or BCG for three years. That’s just what cookie-cutter Stanford person is and it’s for worse or for worse. They would all say, “Wow, I want to make this career pivot. I want to do something different. I’m here because, yes, I’ve been in consulting, but I want to be a product manager. I want to do something else.” They would do it and then they would, at the end, be like, “You know what? I’m just going to go back into consulting or banking,” or whatever soul-sucking mindless job they want to do.

I was like, “I’m not going to do that.” I know I came here to elevate the business side and do something bigger and better in business but what better to do than start my own, do my own thing and see what happens. Throw myself to the fire. Granted, I was already making decent money on the side doing this, but it was always kind of a scary thing. If I don’t do something that day, if I have a bad day, the business has a bad day if I’m by myself, right?

Tubefilter: Yes.

Ross Pomerantz: I’m very much a team guy. The thing I love about productions is there’s a bunch of people there. I missed playing baseball. Being a content creator is, for me, very lonely at times. Especially not being in L.A., I don’t have a lot of people to collab with and so forth. I went in on it. 2020 is the short answer to that and I’ve been doing that pretty much since I graduated.

Tubefilter: What is your current approach to making videos? You went full-time and then you went all in on Corporate Bro. What does your digital presence encompass now?

Ross Pomerantz: I’m on every single social platform. In fact, I would say the one differentiator for me, the most I’m dominating is on LinkedIn. I know everybody’s like, “What, LinkedIn?” It is an interesting angle because I’m on this middle ground of demographic where me, personally, I would say I’m a younger human inside than out, but I don’t consume YouTube in the way that so much of Gen Z does for entertainment. I mean, I’m all over YouTube. How do I edit this? How do I do this type of effect in Final Cut? How do I do all these things? I’m on YouTube, but I don’t seek it out for entertainment specifically. I don’t have it on my TV. For me to go in and cast something that’s a whole ordeal.

This group of people on LinkedIn, they’re more like me and older, and it’s very evergreen for me because a lot of them, like this content concept for them feels very fresh. There’s not as much competition for me on there. Obviously, what I do is business and professional related. I try to make it edutainmainment in a lot of ways.

Tubefilter: Are you video heavy there too or are you doing text as well?

Ross Pomerantz: Yes, extremely. Extremely video heavy. It’s still my same videos. I put them on there. Obviously, some things I’m like, “Uh, probably shouldn’t put that one on LinkedIn.” I mean, there’s also others. I run an investment group through my followers. I do a lot of early-stage advisory work. I still use my MBA in a fair amount of ways, and so I have my ear to the streets in tech, mostly because I have to. It’s great for content. I want to be a satirical smarter version of content. TikTok, I play the game but I don’t like it. I like writing scripts. I like writing witty, smart-like scenes, but those still don’t play as well as me lip-syncing to Taylor Swift. That’s very frustrating to me, but it is what it is.

Tubefilter: That’s fascinating that you’re doing well on LinkedIn. I don’t think I’ve spoken to anybody who’s doing well on LinkedIn.

Ross Pomerantz: It’s hard. There is a professional piece to it, and people know I was in sales and people care about the companies I endorse and the products and people come to me for career advice all the time. There is a piece of me that still has a leg in Silicon Valley and on the more professional side of things, even though my content is absolutely outrageous on there and very much would be considered unprofessional.

I think it’s refreshing to so many of these people who have lived their lives buttoned up and corporate, so to speak, to see it out here. They’re like, “Oh, maybe we can be a little more human in the corporate side of our lives.” The way Gen Z already comes in is probably a little too human when they enter the workforce. 

Tubefilter: I do feel like your videos really nail this interesting satirical tone.

Ross Pomerantz: It all comes from the life I’ve lived. It’s so interesting how the word corporate and professional in and of itself, to me, is a farce. It’s just basically: cover up all your faults. Be this lie. Then when you go home, then you can be real again. “Oh, fuck, I want to smoke a bowl and watch TV.” You can’t just say that at work. To your friends, you can. It’s like you’re seeing companies now promote the whole human. “We recognize that your life isn’t us.” Thank you, finally. Whether or not they actually put that into practice, it’s a whole other thing. It’s an interesting shift. They say it.

Tubefilter: They sure do. What’s an average production week look like for you? Is there a certain number of videos you’re aiming to put out per week?

Ross Pomerantz: Forever it had always been one because I require an office. I would go, I would get friends, family to show up. We would do shoot days on Saturdays. I’d buy everybody coffee and lunch and we’d mess around in an office. Usually, I would come with three or four scripts, and then I’d be like, “Okay, great. We don’t have to do this for three more weeks.”

Obviously, that had a change because all these algorithms are just like, “We don’t give a shit what you post, just post a lot.” I personally can’t stand that. I think my goal is still two a week, which would be like a sketch plus what I’ll call a TikTok, a sound. One that takes very little thought. It’s more of a copywriting exercise. It’s a video meme, so to speak, which to me is more writing exercise, and then just like, whatever visual I want. I say it’s two. I would love to do more. I think it’s hard for someone like me who’s just like, “No, it’s not good enough. I need to edit this better. I need to retake this line.” The world of content, the world of consumers of content, they just don’t give a shit anymore. It’s like, just throw a shitty green screen on TikTok and be like, “I’m in a bar right now or I’m here.”

Whereas I’m someone who’s like, “I’m going to go to a bar and shoot this.” I’m going to go places and shoot these things.” I’m old school like that. I’m just like, “I want to do this better.” It doesn’t mean it performs better. Then I’m like, “Why did I spend 12 hours on this video that didn’t do as well as a trending sound?

Tubefilter: How do you balance, or–how do you reconcile that, I guess, creatively? Because, obviously, creatively, it’s fulfilling to make things that you’re proud of, but then…

Ross Pomerantz: I reconcile it through therapy.

Tubefilter: [laughs]

Ross Pomerantz: It’s true. I think it’s part of playing the game and it’s unfortunate. It is what it is. As long as you’re a social media content creator, you’re beholden to the algorithms, you’re beholden to the platforms themselves, which is terrifying. There’s many times where I have to go back and, “Did I laugh when I wrote this? When I thought of this in the first place, did I laugh?”

That’s what I go off of. My taste is my taste and my taste is usually pretty good. I’m a weirdo so I’m a little unhinged and I’ll do things that people are like, “Whoa, what the fuck just happened? That got real weird.” That’s me and I don’t apologize for that. I will always be like, “That one was for me. I don’t care if this performs or not, that one was for me.” If that happens over and over and over again, I’m like, “Fuck, I should go back to the basics of what gets views of what the algorithm pushes to people.”

I would say the most frustrating thing is I’ll post a video that I know is good and a third of my audience will see it because it’s decided that only a third of them will see it. Even though they press the follow button and have said, “I like this guy’s content,” only a third of the people are going to see it. The way I reconcile it is I go back and forth. I just go back and forth. I have good days, I have bad days, I have good weeks, I have bad weeks, and I just try to make stuff and try not to put too much on it.

Tubefilter: What are you working toward as a creator in general?

Ross Pomerantz: Hell, am I working towards anything anymore? I’m still a little bit in the fallout of this show. The show consumed me for a year and a half. I was making every single creative call at the end of the day. From making spell-checking credits to like writing it and acting it and it was just a lot of work flying back and forth to L.A. I am working towards trying to do a second season. I’m working towards trying to do bigger pieces of content. I want to move more into TV. Ideally, comedy TV.

There’s just not enough comedy going on these days. You can look at the nominations, somehow The Bear is listed as a comedy. That’s where we’re at. Nominated for comedy. It’s so dark. In a couple of moments, it’s funny, I guess, but it’s not a comedy. I would love to get back to the days of Will Ferrell and Danny McBride and when we had these movies that were coming out constantly that were just so funny. We think about the heyday of comedy. I would love to spark that again. Obviously, studios are like, “Does it sell in China?” “Sorry. No, it doesn’t because it’s comedy.” That’s what I would like to do.

I want to move into more traditional like longer-form stuff, which, I know the world is shifting towards short-form, but that’s what I want to do. I would rather spend all year working on one single project and put it out once a year than make the social media wheel of once a week or even three times, five times a week.

Tubefilter: That’s what I was curious about because, to be honest, it doesn’t seem like you’re enjoying the short-form side of things.

Ross Pomerantz: I don’t enjoy it because– Have you heard of the phrase “the ennui engine”?

Tubefilter: Yes.

Ross Pomerantz: That’s where it is. I also, like, you’re a journalist, my dad’s a journalist, you spend time talking to people, researching, looking for…You’re researching the story. You don’t come in with an agenda. There’s no bias there, ideally, right?

Tubefilter: Ideally, yes.

Ross Pomerantz: Ideally there’s no bias and you spend all this time and you put something out, whereas someone goes on WorldStarHipHop and just posts a meme that says like, blankety-blank, like some headline, some inflammatory headline. Everyone takes that for fact and that sucks. We’re moving away from the appreciation of art and that sucks. That bothers me because I just think we’re better than that. You don’t have to enjoy the art. You don’t have to like the art, but you could still be like, “Yes, I could see why other people would like that art.” We won’t watch a video that’s longer than 30 seconds. That someone’s put all this time and it’s like a beautiful thing. We’ll go see Oppenheimer because of the hype and we’ll go billion dollars to make it whatever it was to make it but there’s a lot of creators out there, especially on YouTube, that are putting out amazing content and people won’t sit down and watch it.

To go back to what you said, I do love what I do. Otherwise I wouldn’t do it. For seven years, I didn’t make a cent because I just liked to go into the office with people making funny things. The creative process is awesome. It was similar to playing professional baseball like I had so much fun playing baseball until it was professional because then you’re playing for your job every day.

Every day, everything you do is so much more scrutinizing. I’m not playing for my job anymore but you got enough people, there’s enough trolls on the internet, there’s enough people that are seeing it and watching it that there’s stress behind it. I feel anxiety before I post. I hope it’s good. I don’t want to let people down. I still love making content. I still love the writing and acting and creation and the editing piece and how to make something funny. Then it gets to live forever, which I love as well.

It’s the rat race that I don’t love. It’s the push by these platforms to say just make more, make more, make more, make more. It’s like, “Ah, I’d like to make it at my own speed and not be punished for it.” I’d like to make something I feel good about and then put it out there not because I need to, because you’re not going to show it to people, because I took a week instead of a day. That’s what I like.

Tubefilter: In some cases, I feel like platforms are really shooting themselves in the foot. Shorts is having a measurable effect on YouTube’s bottom line. Their quarterly earnings have been dropping because people have been watching Shorts without ads for a long time. It was impacting the money they made from their long-form content but they were still pushing shorts as like the new top thing on YouTube.

Ross Pomerantz: They’re watching TikTok and I do wonder what would happen if the platforms, unified, said, we’re going back to long-form content. I remember when YouTube was all long-form content. I was getting screwed during that time because I was only making one-minute sketches. I was like, “I got to make longer stuff if anyone’s going to watch it,” and that’s just funny how it’s all flipped on me. Now I want to make longer stuff. Now I can but I shouldn’t. If they unified and said, “We want longer form content,” what would happen?

The reality is people’s attention spans are just going to zero. You can feel the stress in humanity through it. You can feel the tension of people by like, they’re just scrolling. They’re just looking for something that they never find. They might find a piece of content but they love it and within a second it’s gone. They’ve forgotten about it in that moment. It’s a terrifying thing. It’s terrifying conditioning that’s happening to people and I think that’s what scares me a little bit.

Tubefilter: There’s no longevity there.

Ross Pomerantz: Why take so much time to make something if there’s no longevity to it?

Tubefilter: I feel like a lot of people are thinking about this and not really speaking about it.

Ross Pomerantz: I don’t know, because people keep going back to the well. Candidly, I don’t want to be Corporate Bro forever. I don’t know what Corporate Bro looks like when I’m in my mid-40s. This is just the platform I have an audience. I want to do other comedies. I want to do other random projects. I don’t even need to do my own projects. I just want to work with creative people who push each other and laugh and make stuff, make the stuff they want to make. That’s my goal in life. I just want to be able to make whatever I want to make and do it with other people who want to make stuff too.

Tubefilter: I feel like your audience is engaged with you as a person, just from what I’ve seen of the comments section.

Ross Pomerantz: There’s been a lot of stories where people will shit-talk salespeople. There’s a lot of shit-talking on LinkedIn about salespeople. People have their professional reputation so they can’t say things. I’ve earned the right on LinkedIn to say whatever the hell I want, so I will go with the throat of people. There’s a Robin Hood-esque element to what I do. I can defend salespeople because they can’t get unprofessional or show a rise when people are yelling at you on the phone. You got to keep your composure.

In that regard, I really spent a lot of time trying to put respect on salespeople and help people understand that so much of what sales is is actually making the world go round, because it is. None of these companies, these tech companies, exist without salespeople, most of them. There’s a few that would exist. There’s an engine of people that is selling and pushing and doing these things across the world. It’s the oldest profession ever. There’s a lot of holdup. I want to elevate the profession. There’s still shitty salespeople. There’s shitty engineers. There’s shitty writers, shitty everything.

There’s a piece of that I think a lot of people resonate with in sales. It’s hard. It’s so mentally draining. A lot of my content lets people know it’s happening everywhere. A lot of people feel the same way. That’s the goal. It’s cool when people say that. Again, it was never intended to be anything other than catharsis for myself. It was just cool that it turned out other people felt the same way. Interesting one.

Tubefilter: Do you have any other projects, plans, goals you’re thinking about, anything else you’re thinking about?

Ross Pomerantz: No project off the top of my head. Obviously, these strikes aren’t helpful. There’s things that I’m working on but they’re still in the idea stage. They’re not even worth discussing. They’re comedies outside of Corporate Bro. Of course, the second season would be within Corporate Bro. I’m still writing and working on that. I’m trying to write that more as network television version of S.A.D., which was 10 to 15 minutes long. It was three episodes for network that we broke into pieces because we didn’t have the budget or time or ability to pull off a full season of eight episodes for network television, especially as amateurs.

That’s the goal. How do I do the next one? What’s it going to take to get there? Right now, there isn’t a clear path. I’ll figure it out. If I want to figure it out, I will figure it out. I’m going to figure it out. It’s still early enough that I can’t give you a clear path yet.

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