CUT Former CEO & Founder: Michael Gaston


Mike was born & raised in Seattle by two very young parents.  Growing up, he had a clear sense of what was right from wrong, and was never afraid to speak up about how he felt about something or to assert his opinion.  He remembers being profoundly depressed throughout his childhood.  Mike admits that he felt a pressure from society and his mother to do what he was 'supposed to do.'  Attend a college, get a job that pays well, and live a standard life.  Eventually his desire to just live in the moment and desire to become some sort of artist would begin to surface.

He left Seattle University after one semester, and decided to travel the world on credit cards.  Although it was one of the greatest experiences of his life, meeting different people and developing deep relationships with people across the world, he admits he came home dead broke and in debt.

When he came back, he attended the University of Washington and got his B.A. in English & Humanities. He then got a job at Boeing, which he admits he disliked so much that he eventually ended up self-terminating.

Mike would go on to pursue his passion of creating art through videos.  He worked for free several times, worked for a non-profit, and worked for a CBS show before landing a job at a studio where CUT would eventually rise from.

CUT was born in 2015 and has since acquired over 10 million YouTube subscribers, sharing videos and stories that go viral.

Podcast Transcript

Note:  There may be errors to this transcript (some funny, some confusing - we used an automated transcription software!)

00:00:04 Ash Faraj: Hey guys, welcome back to another episode of ExecuTalks. It’s the place to connect with today’s top executives.  I’m your host Ash. In this episode, you will get to hear from the founder and former CEO of CUT, Michael Gaston. CUT shares stories through videos that go viral. Since they’ve been founded in 2015, they’ve acquired over 10 million subscribers on YouTube.

00:00:32 Ash Faraj: Hey guys, real quick, Season 3 is coming up soon. Before we get into the show, I just wanted to let you know that we’re launching ExecuTalks Video very soon. If you’d rather watch interview highlights to get peoples’ stories or you learn better through video, we will soon have that available. Also, if you’re feeling stuck in your career and you’d like someone to talk to, I’d love to be there for you. Shoot me an email at and I’d love to connect.


00:00:59 Ash Faraj: Mike was born and raised in Seattle. Growing up, he had a clear sense of what was right from wrong and was never afraid to speak up about how he felt about something or to assert his opinion. He remembers being profoundly depressed throughout his childhood. Mike admits that he felt a pressure from society and his mother to do what he was “supposed to do”; attend a college, get a job that pays well, and live a standard life. After high school, Mike attended Seattle University and left after just one semester. He decided to travel the world on credit cards. Although it was one of the greatest experiences of his life, meeting different people and developing deep relationships with people across the world, he admits that he came home dead broke and in debt. When Mike came back, he attended the University of Washington and got his bachelor’s in English and Humanities to fulfill his mother’s desires for him. He then got a job at Boeing, which he admits he disliked so much that he eventually ended up self-terminating. Mike would go on to pursue his passion of creating art through videos. He worked for free several times, worked for a non-profit, and worked for a CBS show before landing a job at a studio where CUT would eventually rise from. In 2015, CUT was born and has since acquired over 10 million YouTube subscribers, sharing stories through videos that go viral.

00:02:28 Michael Gaston: Hey, how are you?

00:02:30 Ash Faraj: Hey Mike, how are you doing?

00:02:31 Michael Gaston: Look at that hair. Look at that quarantine hair.

00:02:33 Ash Faraj: Oh, my God. [laughter] So, how are you? I think last time we talked you were giving me elbow, and… It was like pre-shutdown, but it was like you were still sick and stuff.

00:02:45 Michael Gaston: Yeah, no. I’m suddenly doing a whole lot of stuff.

00:02:50 Ash Faraj: So, Mike, what’s your favorite book?

00:02:52 Michael Gaston: Right now, my favorite book is Octavia Butler’s Parable of the Sower. And then, for non-fiction, there’s a book called Black Imagination that a friend of mine wrote, her name is Natasha Marin. It was part of a conceptual art piece that she did where she invited black people to share an idea about blackness with her in her art series. She’s a black woman. What’s wonderful about this is you read it and it feels meditative. It feels like an invitation to see blackness through a lens that isn’t filtered by whiteness.

00:03:36 Ash Faraj: Favorite movie?

00:03:37 Michael Gaston: Oh man, Ghostbusters. I would say Ghostbusters or Brewster’s Millions.

00:03:45 Ash Faraj: Public figure you look up to?

00:03:47 Michael Gaston: There’s a writer for The Root who I really respect, Michael Harrington. I would say this guy. I love him. He does a  wonderful of just conserve, like breaking down, this moment and contextualizing it against history. There’s a local State Senator, named Joe Nguyen, who I’m really impressed by because he really sticks up for shit that matters locally. And then there are other people like, you know, I’m a big fan of AOC. I know that seems like corny or cheesy in the moment, but I think she actually lives the things that she says.

00:04:21 Ash Faraj: Favorite vacation spot?

00:04:23 Michael Gaston: Mexico. A friend of mine has a house in Todos Santos that’s like on the water and it’s incredibly quiet. You can fish off the beach and just chill out. It’s kind of in the middle of nowhere. It’s wonderful.

00:04:36 Ash Faraj: Favorite dessert?

00:04:37 Michael Gaston: Man, that’s a hard one because I got a crazy sweet tooth. I’m just going to go with cake in general.

00:04:43 Ash Faraj: Favorite childhood memory?

00:04:45 Michael Gaston: I remember I was like five. I remember this by the way. I was five. My uncle called the house, and I answered as a five-year old. He was like, “Hey! I need to talk to your mom.” And I go, “She’s busy right now.” And he’s like, “What do you mean she’s busy? Go get her.” I’m like, “I can’t. She’s busy.” He goes, “Why? What’s going on? What about your dad?” I’m like, “He’s busy too.” And he’s like, “What do you mean?” I’m like, “They’re humping. They’re humping right now.” And he’s like, “Oh, okay. Bye.”

00:05:14 Ash Faraj: And you were five? [laughing]

00:05:15 Michael Gaston: I was five. My mom found out later that I said that, and she’s like, “Wow, do you even know what humping is?” And I’m like, “Yeah, it’s when you close the door and there’s lots of noises.”

00:05:25 Ash Faraj: [laughter] Oh my God, that’s funny. Speaking of your childhood by the way. Can you paint us a picture of who Mike was as a child?


00:05:36 Ash Faraj: Hey guys, hope you’re enjoying the show so far. Just a quick reminder that every rating and review helps us help more people. If you have just five seconds, and I know you do, please leave us a quick rating and review on Apple Podcasts so we can grow organically in order to reach more people and help more people. Now back to the show.

00:05:56 Michael Gaston: Sure. I mean, I was fairly obnoxious, you know, like the nice way of saying is precocious as a child. I loved writing and I loved drawing. I fancy myself a poet. People thought of me as one of the class clowns. I also had a very clear sense of what justice was. I remember telling people like, “No more bullying. Just no more. We’re not doing that.” Because there were a couple of kids in class who would try to bully other kids, and I was just like, “No. No one is going to have that anymore.” That was in seventh grade. I remember what happened was a friend of mine, he wasn’t like the type of kid who would hit people but he was the type of kid who was always pulling other kids’ cards in terms of a very assertive authority. He would often try do a thing where he would be like, “Hey, we’re not sitting with this kid today,” and then everyone would move. I remember one day he did that, and I was like, “Dude, that is stupid. I’m not going to move. I’m going to sit with this kid.” So, I sat with that kid. Then the next day, my friend was mad at me for doing that, and so he goes, “Okay, no one is sitting with Mike.” I was like, “All right, cool,” and I just went and sat down with all the ladies.

00:07:17 Ash Faraj: Interesting. What was the relationship like with your parents?

00:07:20 Michael Gaston: Well, it’s funny. I’m actually pretty close to both of my parents now as an adult, but there was lot of tension when I was growing up, especially with my dad. We did not have a good relationship. We constantly fought. Multiple times nearly coming to blows. They had me when they were 22. I remember growing up and they would say things like, “Aren’t you glad that you have such young parents? We’re so much younger than your friends’ parents.” And I was like, “It’s terrible. It’s terrible because you guys don’t know anything and you’re super impatient. If you had maybe waited some more years, maybe you’d be better parents.” That was the type of relationship that I had with my parents.

00:08:02 Ash Faraj: If there was one person in your childhood who had a significant impact on shaping your life’s principles, who would that person be?

00:08:13 Michael Gaston: It’s funny because I can recall different people for different reasons. I’ll say that there’s a kid in my class, his name was Jorge Morales, who I would still consider a friend. I just haven’t seen him in years. Jorge gave me a book. The book, it’s not like a terribly good book. I think it was called The Illuminatus Trilogy. But it was a book that was filled with a lot of different philosophical ideas, like solipsism and stuff like that. I had never read anything like that. It made me really curious about different philosophical concepts. As a result of it, I just started… Whatever I could find I would read. Until that moment, this was in seventh grade, I had a very sort of like surface-level understanding of the “why’s” behind the choices I was making. After that book, and after even my relationship with Jorge, I just became a lot more reflective about everything and the types of books I read were very different.

00:09:14 Ash Faraj: As human beings we tend to remember how we felt throughout our lifetime. What emotions do you remember feeling frequently throughout your childhood, throughout your teenage years up until you went to college?

00:09:31 Michael Gaston: Depression. Unhappiness. I had severe depression and anxiety came later for me. I remember being depressed in second grade and all the way through high school, like a profound kind of depression. I remember there were a couple of moments where I could have gone the wrong way and then a friend helped me. Disappointment in what seemed like a not very interesting track for life. Like I said, my mom was very intense, you know, having come from the Philippines. I could do everything that you’re supposed to know how to do like in fourth grade, but I knew how to do it in kindergarten. I was a kid who was just bored because I could read everything. I could do all the math. Like nothing was interesting. But you were kind of on this progressive track. It was like, you have to know how all these things, so that way you can get in this good school. And once you’re through this good school, you get into this good school. Then after that one, you’ll get into this one. Then after that you get a good job and then you can do all these things. I just remember, like seventh grade was sort of like a formative year for me because I just said, “None of this makes sense to me.” Like this sort of series of things that I have to do in order to do what? So I can end up in a place where I have a job? So I have a house, and I have all these things? It’s almost like I could predict the rest of my life and it was boring. I had no interest in it. So I started to reject all those things. As a result, I ended up, you know… I remember at one point I dropped out of college and traveled the world. Ended up living with a poet on the Southwest Beara Peninsula by Ireland. He was my mentor and I would just read poetry, and study poetry, and write poetry every day. And I would have to go fish for food every day because I had literally no money. I started living a different kind of life, one where it was like, okay, what are the things that I’m really interested in? I’m not going to worry about what kind of return on investment I’m going to get. It was like a life that was actively rejecting a lot of the expectations that my mom, in particular, had set up for me. It’s this weird sort of like, you’re allowed to be an artist as a hobby, but otherwise you need to go have something more practical. I just started rejecting all those ideas. I was actually planning not to go to college, but my… As part of this whole guilt trip scenario where my mom, she had been planning since I was a child that I was going to college, so I ended up doing that. I mean, you also raised me as a Catholic, so I guess I’m just steeped in guilt. Let me go do that. So I went to SU for a year. At the same time, my grandfather on my dad side was essentially dying. He had diabetes and he couldn’t see. He had no more feelings in his left hand or his left leg. He had experienced multiple strokes, multiple heart attacks, and they couldn’t afford someone to help him. So it was my grandmother and then me. When you’re in college you have classes at different times, so I could go over there and help him. I would literally help him use the restroom. I would help him take a shower. I was getting progressively more and more depressed at this moment. I remember, at one point I told him, “I just got to get out of here because I don’t want to be in the school. I love you, but this is not… I don’t want to see this anymore.” He’s like, “I don’t want you to see this. I want you to leave.” And he’s like, “Just go. Just leave.” Then I just left the country and then I didn’t come back for a long time.

00:13:09 Ash Faraj: You didn’t have a plan? You just like…

00:13:11 Michael Gaston: Yeah.

00:13:12 Ash Faraj: Wow. Where was your first stop?

00:13:15 Michael Gaston: It’s funny. When I left my girlfriend at the time wanted to travel. She was from Poland. I went with her to Poland and then traveled around a bit. But then she had to go school, and I just continued. Then I ended up living with that poet, who I had met on a study-abroad trip during my first year in college. He welcomed me and allowed me to stay there and continue my independent study. I just lived there for a while. I also made like weird excursions to Mexico and various other countries, just randomly. Then I came home and completely broke. By the way, I’m going to be really candid with you. I think I told you this when I met you a long time ago, but I had traveled multiple times. I had done the kind of traveling that everyone talks about, the backpacking through Europe and that kind of thing. When I kind of cracked and I was like I got to get out of here, I just decided that I was going to travel differently. So instead, and I thought about it, I was like how can I rob a bank? I was thinking like this. How can I rob a bank and not go to jail? Then I was like, ah, I’ll just take out a bunch of money on credit cards. So that’s what I did. I took out a crazy amount of money on credit cards, and I traveled first class in a number of different ways. I would bring a satchel with me, and I would buy clothes whenever I needed it.

00:14:42 Ash Faraj: So you came back. You attended U-Dub, right?

00:14:45 Michael Gaston: Yes.

00:14:45 Ash Faraj: And then you studied English and Humanities. Then after that, I assume, those feelings of depression came back. You got a job at Boeing, which a lot of people… some people that don’t have jobs would wish to have, work for Boeing. What was Boeing like?

00:15:01 Michael Gaston: When I went, at the time, Boeing had gone through so many layoffs, so many histories of layoffs, that there was a huge generational gap between the people who were there and the new people they were hiring. There were basically people within 5 or 10 years who were going to retire and then there were like kids straight out of college. There was almost no middle zone. They had been laying off so many people. There was a real culture conflict that was happening. This was also the time where the Dreamliner was being made. Up to this point, Boeing had been known for a certain amount of expertise and craftsmanship in the making of their planes, but when I joined them they were in the process of getting rid of that, or attempting to, in order to squeeze out more profit. I remember it very vividly, within a couple of months, being in kind of an all-hands meeting forecasting the future. It was all about the Dreamliner and how great the fucking Dreamliner is going to be. They go, “Does anyone have any questions or concerns?” and goes around the room. I was basically brand-new. I was an entry-level procurement agent. Then I was just like, “Yeah, I have a question.” “What’s your question?”  “So it just occurs to me that we’re creating a brand-new plane; like brand-new, never been made before. Using materials we’ve never made before or used before with a supply chain that we’ve never done before for a client that’s notorious for claiming bankruptcy. Why? Aren’t you guys concerned? Aren’t you concerned that we’re actually not going to hit these deadlines? Because I’m a little concerned right now that we’re being really overly ambitious. Especially this idea of outsourcing production to these different groups and different countries that have no expertise in this.” They were like… It was like one of those… I recalled being a child and getting the pound in the head for being precocious. There was sort of like -- My manager was like, “What are you doing? Stop it.” Needless to say, the Dreamliner was definitely years late, and it was the result of simple things. Like, for example, I remember when they were building a factory in Italy and they had just figured out, “Oh, shit. We can’t actually build anything here because in Italy you can’t just rip out these olive trees.” You literally have to pull them out and then replant them. So where they were planning on putting a factory they had to literally take out and replant all these olive trees. Or like the fact that there were fundamental differences in communication styles with Japan, or… There’s like so much more additional overhead they put on themselves because they were attempting to please the stock market that it ended up just fucking up the whole process.

00:17:53 Ash Faraj: Did that create a lot of tension with you and management, or whatever, because you were outspoken?

00:17:59 Michael Gaston: No, in fact, the exact opposite. I would say that people who are white-presenting and are straight and dudes, the louder you are the more you get rewarded. The truth is I actually set a task for myself. I was like, “Can I get fired here just by being weird?” I’m not going to be sexist or racist or homophobic. I’m not going to bring a gun to work. I’m not going to do drugs. If I’m just weird, will I get fired? The result was no. I got promoted twice. In the middle of this world where I would do things like busk in the hallways with my guitar, or I would run meetings where no-one knew who I was. I would just show up into these offices and just take over a meeting. Like the louder you are, the more particulate you are, the more you’re going to get rewarded. It’s crazy. What it does it makes it very clear the privilege that you have for that kind of position.

00:18:51 Ash Faraj: At a certain point -- I think it was after two or three years -- you self-terminated was it?

00:19:00 Michael Gaston: Yeah, I did. I totally self-terminated. Boeing has an internal intranet called ‘Total Access’. On Total Access there’s a big red button and it’s the self-terminate button. If you press it then you essentially are quitting. I pressed it and I immediately got a call. The call was from HR. They’re like, “Hi. This is HR. Am I speaking to Michael Gaston?” I’m like, “Yes.” “Did you just press the self-terminate button on Total Access?” I go, “Yes.” “You do know what that means, right?” I go, “Yes. It means that I’m not going to be working here anymore, right?” They go, “Just to let you know, it’s very difficult to reverse this once it gets started.” I’m like, “Why would I reverse it if I pressed the button?” They go, “We’re just telling you. You can’t reverse it.” I go, “Okay.” And they go, “Do you want to reverse it?” “No Ma’am. I pressed it for a reason. Please, I don’t want to be here anymore.” It’s just very insane if you think about it. There’s a company that literally has a self-terminate button on their internal intranet. It’s weird.

00:20:00 Ash Faraj: So, what next? What did you do after that?

00:20:03 Michael Gaston: I left that, and I just got heavy into video. The whole reason why I left is because I made a music video for a friend that kind of took off. I was like, I’m going to do videos now. I think the thing is, when I was young, I always knew I wanted to be an artist. But I thought it would be in drawing or writing because those are solitary activities. They don’t require other people. Film always seemed too hard because you got to collaborate with a bunch of people, or the equipment is expensive, and it didn’t seem real. Then I made this music video for a friend out of nowhere. The label bought it. It was on MTV, and I thought, “Shit, maybe this is doable.” So for the next year, I basically worked for free for whoever would have me because I wanted to know what it was like to work on different film sets. Don’t get me wrong. I didn’t have some vast amount of savings. I was broke. I was dead, negative broke and just barely getting by. Then suddenly, I started getting some work. I was paid because I was starting to learn what to do. Then eventually, I got a job at CBS Radio Seattle as the Video Production Manager for a show, called the Bob River Show. I did that for about a year. Then when Bob moved on, I started a digital humanities non-profit that was all about exploring some of these themes that I ended up incorporating in my work at CUT, but through a non-profit lens. So you go for a year of not making any money. Then you go for a year where you make some money. Then you start a non-profit where you’re making no money again. So then I had to go get a job. When I did, I ended up applying at this company, it was like a marketing start-up. They ended up being the start-up studio that CUT came out of. They provided the seed investment.

00:21:51 Ash Faraj: I want to backtrack, just for a second. The friend that you made a music video for where did you meet him? How did that even happen initially? Was this a friend of you for a while?

00:22:02 Michael Gaston: I met him in Ireland.

00:22:04 Ash Faraj: Oh, so when you were doing your traveling?

00:22:06 Michael Gaston: Yeah. I met him on that first study-abroad trip to Ireland. He was a senior, and I was a freshman. He was in a band. We became friends on that trip. I remember his stuff was always on MTV. He was in this band called Minus the Bear that was pretty successful in terms of like an indie rock band. I just told him one day that I had an idea for a music video. He was like, “That’s great. I’m glad, but you’ve never made one.” I was like, “I’m just going to make one anyways.” Then I made one and they dug it.

00:22:39 Ash Faraj: Wow, interesting. So I think most people are like, I’m not going to work for free. Can you tell us a little bit about the value of that, like to the people who think that working for free is for chumps?

00:22:51 Michael Gaston: I was operating under the belief that I really didn’t know what the hell I was doing. Even though I made a music video and it had made money, in some cases that was just a fluke. In some respects, it was just sort of like a fluke that I was able to do that. Maybe I had some kind of vision, but everything I was doing I was just sort of making up. There was this belief in my head that I had to get a sense of how everyone sort of works, right? I know that there’s a kind of a trope of hustle culture; this idea of ‘I will work for free. I will do anything.’ The thing is, I never wanted to be a businessperson. I was operating under the kind of an artist mentality about things. If I was really invested in something, I would just immerse myself completely in it. If I wanted to write, it meant that I was going to read every book on writing. I was going to read every book from the authors I respected. I would completely do that. Then I would write without any expectation of publishing it or making any money because that’s what I cared about. So video, it wasn’t like a stepping-stone in order to get more successful, it was just this is the fastest entry point to learn a whole lot about this thing that I really give a shit about right now. That’s all that mattered to me. If I set up like a gatekeeper thing, where it’s like I’m only going to work if I get paid, then people are going to ask questions like, “What do you know?” Well, I’ve only made this one thing, so I’m likely not going to get hired. It’s better for me to not get paid because the experience is going to be so much more valuable.

00:24:24 Ash Faraj: That makes sense. A lot of the people I’ve talked to don’t have much experience, and I kind of suggest that; giving the company a free trial to manage its risks. To a lot of people, it just seems like a bad idea. I wanted to get your thoughts on that.

00:24:42 Michael Gaston: One thing is like, let’s say you wanted to apprentice under somebody. You’re like, “Listen, I will work for free for you for three months or whatever because I just want to learn” or you go to a company and you just try to suggest that. What you really be doing is you’re putting it all on you. You’re saying like, “No, you don’t understand. I’m going to be so fucking good at this. And after three months, not only are you going to hire me, you’re going to pay me way more than other people are because I’m going to be way better. What’s beautiful about that is it’s on you. It’s on you to prove it in that moment, right? Three months is not a long time, even a year isn’t really that long of a time. I worked two jobs in order to graduate through college. At one point, I was waking up at like 4:00 in the morning so I could go to work at UPS. I would then go to class, and then I would go, and I worked again at night at a sandwich shop. I’m not saying this as like some sort of badge of honor, or like anyone has to do this. I’m just saying it from a point of view of like, think about it in the sense of, what do you fuck do you want? What are you going to do for it? If you’re not willing to be uncomfortable for a short period of time because three months is nothing, a year really is nothing. Then you didn’t really want it. That’s what I tell people. It’s not about laziness or anything like that, it’s really about you didn’t want it enough. If you want it enough, you would be willing to do it.

00:26:07 Ash Faraj: Wow, that is powerful. You got to really think about what you want because, if you really want something, you’d be willing to endure pain.

00:26:16 Michael Gaston: Whatever it takes, yes. A year to like figure out whether or not you can be any good at something. The people who are, “No, no. I need to get paid for my time.” I get it. Without money we can’t survive. I absolutely get that. But if you don’t know anything, and you haven’t proven anything to anyone in the space that you actually give a shit about, then no one is going to give you money for it. Not really. So in order to get that kind of information really quickly, like download it into your brain, the type of knowledge that would actually make you an expert in that field, like the fastest way to do it, is just to start fucking doing it for whoever will have you for literally whatever amount that they’ll spend; and if it’s nothing, whatever.

00:27:00 Ash Faraj: That’s powerful. I want to fast forward a little bit. When you were at Stripes 39 -- Stripes 39 is it a parent company of CUT or is CUT the parent company of Stripes?

00:27:11 Michael Gaston: Stripes 39 is a start-up studio that CUT was incubated in.

00:27:14 Ash Faraj: At a certain point during that time, you had like an idea of short films with an emotional punch. There had been investors that invested a quarter million dollars already. They were saying you should copy these other media companies that have already been successful, and you did completely the opposite. Take us through that how you just did completely the opposite of what was suggested to you.

00:27:47 Michael Gaston: Sure. Stripes was an interesting place because they were known for SEO lead generation and they were kind of the experts in that space. They were really efficient and essentially buying portfolios of sites and then making them number one on Google, and then driving value from them through lead gen, but they weren’t happy in that field. What they really wanted to do was take all the money that they had made and become the kind of company that invested in other models. Video was one of those spaces that they really believed in, but they didn’t know what kind of model could come out of that. CUT was the third sort of iteration on a model. I had come up with a few different ones that were highly built out. It had really strong decks. I just wasn’t happy with any of them. I was ready to move on when the president of the Stripes Studio goes, “You know, you guys are really good at making things that spread virally. You’ve done it many times. Just go ahead and do your own thing.” One of the things I had told him was, “You should just trust me. I have a vision for the kind of content that I want to make.” I told him the model was going to be one where you create really great IP and then that leads to people paying for things directly related.” He goes, “Yeah, go for it.” So, within a couple of weeks, he started getting on my ass because it takes a second to make a video. You sort of have to plan pieces together and our very first video Grandmas Smoking Weed for the First Time wasn’t out yet. It was in that moment that he was giving me a lot of pressure, and the pressure was to adopt the best practices of Upworthy or BuzzFeed. I was like, “Why would I do that?” He goes, “Well, BuzzFeed and Upworthy have all the money. When you have all the money you can afford to buy things. You can buy all the chief technologists, all the data, and as a result of that those companies have the tools that are helping them to predict of being online. What you can do, because there’s only three of you, you guys can sort of draft off of that success and iterate faster than a larger company. And I go, “Maybe it’s because I’m an English major. But I don’t know a moment in the history of anything where a smaller force somehow defeated a larger force by copying the strategies and tactics of the larger force. It just doesn’t happen. So no, I’m not going to do any of that. I’m going to do the opposite.” And it worked for us.

00:30:10 Ash Faraj: I think that goes back to what you did at Boeing where you were willing to speak up. I’m starting to connect the dots from your childhood, being outspoken, not afraid to actually do what you believe. I’m just connecting the dots and I think it’s powerful.

00:30:29 Michael Gaston: Thank you. I was talking to a friend of mine about everything that I’ve been through, the choices that I’ve made, and everything. She was like, “Well, I get it Mike. I get why you would start a company and it would be successful and then you’d be comfortable moving on. Or like the fact that you’re comfortable saying these things to people who are giving you money or you’re comfortable saying these things to different employees. You’re just a very confident person.” I told her, “Actually, I’m really not. I’m pretty racked with self-doubt literally all the time. Like the things that I’m confident in are that most things just don’t matter. So much of success is luck. No one person gets anything done by themselves. I can make all the right decisions and they can lead to wrong outcomes, or I can make all the wrong decisions and they can somehow result in the right outcomes. In a world like that I should just kind of do whatever the fuck I feel like doing.

00:31:21 Ash Faraj: Thank you for being vulnerable too and just admitting that you also have self-doubts because I think that people can relate to that as well. You had like an “Oh, shit” moment -- something I think I read online somewhere -- where you had a bunch of VC money and then you went through a really rough patch because you had to complete your project. I don’t know if it was the same project or a different project, but there was a project you had to complete and then you were just literally hiring people of a resume, like you had no process.

00:31:50 Michael Gaston: This whole starting a start-up thing was sort of like accidental. In the sense that I didn’t really know I was doing it until I was in the midst of it. It is one thing to get a whole bunch of money. It’s another thing to go and spend it. Once I had this money, I had this whole like, “Oh, no. I have to do something with this now.” My ego had written a bunch of checks and now my body had to go cash all of it. How the hell am I going to do that? What I need is adults. And my instinct goes, “I will find those people who are already doing it, who already have these really killer resumes. They’ll come in and they’ll tell me what to do.” That’s what I started doing. The problem is I gave myself no credit for how I got to that point, right? I just figured I didn’t really know what I was doing; that maybe operating so much by intuition wasn’t strong enough. I started overruling my instincts and hiring people that in my gut I was like, “I don’t know if they’re right, but on paper they looked really right.” The result of that was we didn’t get anywhere for like a whole year, because I was trying so hard to make them successful. They were frustrated and I was frustrated. I didn’t know that by trying to make them successful, I was actually ignoring the success of the company. In fact, in some ways, I was hampering their personal development, right? Because if you’re not right, you’re just not right. Just because they’re not right in your company doesn’t mean they wouldn’t be brilliant in somebody else’s. But by not admitting that, by not quickly making the decisions about that, I was actually hurting my company. This is kind of where that philosophy came out of, fell out of that, which was most of us are making shit up as we go along. We’re just literally trying to figure it out. What you have to be like really focused on are the principles that you believe in because the processes on how you’re going to get there is just whatever, it changes constantly. When you’re three people, you’re fundamentally different than when you’re five. When you’re ten people that’s 50% different from when you were five, right? Every time you add people to the company that you’re building it becomes more complicated. It becomes harder. Whatever processes that got you there, it’s not going to be the thing that takes you to the next step. So you’re constantly having to rethink process. The way you survive that kind of constant upheaval is by dialing in completely on your principles. What are these things that I believe. If you’re ever in a situation where you have to compromise on your principles in order to get what you think you want then you know you’re probably making a mistake, because that’s an area you should never compromise on. That’s something that I learned only after I made the mistake of hiring because of resumes.

00:34:33 Ash Faraj: That makes a lot of sense. You once mentioned that, and I found this really interesting, and I quote, “I tell my younger self that all the exploration, all the seemingly fruitless passion projects, side interests, last-minute travel plans, end up in a piggy bank of creative instincts and skills that are just waiting to be cashed out.” I thought that was really powerful. Can you just expand on that a little bit?

00:34:54 Michael Gaston: Sure. I’ll go and talk at some of these high schools because my wife is a teacher. I feel like it’s a shame how, especially in this moment, the way kids are being taught everything is like going bowling, but with gutter bumpers. Everything is linear path. All you have to do is learn these things and you’re going to be fine. Life is just not like that for the majority of us. It never will be. You’re going to go down all kinds of weird creative cul-de-sacs, like where you’re suddenly saying what am I doing now? I’m like on a fishing boat in Alaska for like a summer because I was broke, but my ultimate goal is to be a hedge fund manager. So how does that relate? Right? People start thinking to themselves, in order to get into business, I need a business degree, or if I want to be an artist, I have to get a degree in art or something. None of those things are true, right? What I’m saying is you should just claim all the things that you find interesting; all those experiences that you got involved in. Claim those things as part of who you’ve become and then you can actually leverage them. I think what often happens is people try to silo and parse themselves up, and be like, oh, I’m not like this person anymore. I hated Boeing. I hated Boeing my entire time there. I can also easily acknowledge that I learned a shitload at Boeing, and that there are things that I learned there that I incorporate constantly in my work today. But if I was stubborn with the self-narrative that I’ve created for myself as an artist, I might reject even the idea of Boeing. I think that’s kind of a problem that happens with people, as they go on in their life, they are telling the story about themselves to themselves. I am this type of person. The reason why I’m successful in this point is because I did “x, y, and z.” The truth is you’re successful because of those things and all the other things you’re not even counting. Claim it all.

00:36:58 Ash Faraj: Exactly. I love it. I read your article obviously about you decided to fire yourself from CUT. But if you can put it briefly, why did you fire yourself from CUT?

00:37:12 Michael Gaston: One of the things I tell kids all the time is you have to ask yourself all the time what do I want? What do I want? Ask yourself that and really know that answer.

00:37:22 Ash Faraj: By the way, do you feel like that constantly changes?

00:37:24 Michael Gaston: Yes, absolutely it changes. There are some things that you might ultimately want that never change. That are maybe a little bit more abstract. I know that I always want to be in art in some way, right? And I know the kind of life that I want, in terms of the types of people I want to surround myself with and the type of work I want to be invested in, but there are a lot of other ones that go into that to too. When I was CEO of the company, I’m being told by all these people externally and by all these social things; we’re told all the time that this is what you should want. You should want to be here because you’re on top of the mountain. If you’re the CEO of your own company and it’s profitable, that’s what everybody wants. The thing is I thought about that. Did I even really want that? And I go, no, I didn’t. What I wanted to do is I wanted to make certain things. The easiest way to make those things was by starting a company, but now I’m in a place where, because we’ve grown so much, I’m now divorced from those things that I was actively doing and that gave me a ton of energy. It was really generative which was like the actual creative work. Now, I’m in a very different role. My role is, I don’t know, being Queen of England or something. I felt like a figure head. It was very unsatisfying. It was hard to kind of give it up because there’s safety in the position. I could have showed up every day and done nothing and everything would have been fine, but the idea of that I found so depressing. I was like, God, I’m making myself soft. I’m not like, who will I be in ten years? Will I be the type of guy who could just do anything, or will I be the type of guy who’s afraid to do anything, because you’ve become so comfortable with themself. I want to keep making things. The only way I’m going to that is if I’m not here. I have to be uncomfortable. I have to put myself in a position of having to do it, again.

00:39:21 Ash Faraj: Congratulations, because I know it’s very recent.

00:39:25 Michael Gaston: Thank you.

00:39:26 Ash Faraj: If you were to meet the 25-year old Mike, what advice would you give him?

00:39:32 Michael Gaston: Oh boy. Floss.

00:39:36 Ash Faraj: [laughter]

00:39:38 Michael Gaston: Definitely floss. Stop eating candy because in a year you’re going to become diabetic. Constantly ask yourself what you want. I’m actually very comfortable with the way my life has turned out. The only thing that I wish is that I had done things to be more mindful of my health. I think it’s really easy to ignore your health, and it’s hard to have a good quality of life when you feel like shit all the time.

00:40:03 Ash Faraj: What in your life you feel has given you the greatest fulfillment?

00:40:07 Michael Gaston: Wow, my wife and kids, for real. I know that’s cliché to say that, but I was never the type of person who was like, “Man, I really want to have kids someday.” In fact, the whole idea just gave me kind of like anxiety. I was like, I’m probably going to be that dad who actually doesn’t like his children. Like I don’t know if this is a good move for me. No, it’s been incredibly satisfying because you’re watching these people, kind of like -- One, they burst into existence already with a personality, and then you realize how much potential influence you have on the type of person that they become. That’s far more satisfying than any type of project you’re working on.

00:40:45 Ash Faraj: Wow, that’s great. What has been the happiest day of your life so far that you can remember?

00:40:51 Michael Gaston: I don’t really concern myself too heavily with happiness in terms of like a moment or a destination because I feel it’s more like a practice. Something that you’re trying to practice all the time which is a sense of gratitude and kind of like completeness. Yeah, I couldn’t tell you one moment.

00:41:13 Ash Faraj: That’s fair. By the way, just curious, for somebody in their mid-twenties who may be is feeling that sort of depression and wanting to find themselves, would you say that a practical piece of advice is just go travel? What one piece of practical advice would you give them for someone in mid-twenties?

00:41:31 Michael Gaston: Exercise. Exercise for real. I don’t know anyone who eats well and exercises who doesn’t experience some kind of improvement in their mental health. I would say eat well and exercise. Then the other thing I would say is, if you’re recommended some sort of drug, for example, I’ve been on Wellbutrin for ten years now, do it. I’m bipolar and what’s amazing about it is, my biggest fear is that it would somehow adjust my personality and it hasn’t. All it’s done is prevented me from catastrophizing and from having manic episodes, but the rest of me is just the same as it was before. Then the last thing I would say is, if you’re going to be depressed, then might as well just do whatever the fuck you want, right? As long as it doesn’t, as long as what you want doesn’t inhibit another person’s personal agency, then just fucking do it and see what happens?

00:42:34 Ash Faraj: If you could be remembered for one thing, what would that be?

00:42:38 Michael Gaston: I don’t know. I think of just being like a good friend. I would hope. That’s about it. I just want people to think that I was a good friend to them.

00:42:46 Ash Faraj: In your opinion, what is the most important life skill?

00:42:50 Michael Gaston: Emotional resilience.

00:42:52 Ash Faraj: Emotional resilience. I love that.

00:42:55 Michael Gaston: The ability to take a hit and keep on ticking, right? There’s going to be a number of times where you’re going to be flat out on a mat thinking this is it. You just got beat and then having the wherewithal to kind of be like, whatever, I’m going to get up anyways. I can go and try. So emotional resilience.

00:43:15 Ash Faraj: What is the best advice that someone has ever given you?

00:43:18 Michael Gaston: Someone said this to me. Like a friend of mine said this to me. He’s a poet and he had no… He’s the type of guy that walks around without socks or shoes on and wears linen pants, and he’s Welsh. He’s kind of like a spiritual hobbit. He was always saying shit like this, but one day he was talking about someone who was really difficult in his life and caused a ton of problems for him and was constantly kind of like an antagonist in his life. I was like, “Twigg” --his name was Christopher Twigg -- “Twigg what do you think about this person?” And Twigg goes, “Well, Mike, I was thinking that maybe this person is a bodhisattva.” A bodhisattva is someone that shirks their own enlightenment to help others achieve enlightenment. He goes, “Maybe bodhisattvas aren’t like these nice kindly angels that help you to achieve enlightenment. Maybe they create a ton of friction in your life, and a lot of anxiety, and they’re antagonist, and that’s a challenge for you to grow.” That totally changed my perspective on shit. Now, whenever I’m confronted with somebody who I find unnecessarily difficult, I think of them as a bodhisattva.  Someone who’s actually challenging me to be better than I was, as opposed to being like an anchor on my life.

00:44:43 Ash Faraj: If you were stranded on an island and had access to one meal, what would that meal be?

00:44:48 Michael Gaston: Oh, shoot dude. I feel like I ask myself this all the time. This is like one of my favorite questions. Right now, it’s pho. I totally eat pho all the time.


00:44:59 Ash Faraj: Thank you so, so much for listening. Now before you go, I just like to share some awesome news. We are including subscribers in our interviews with today’s top executives. If you’d like to be part of our interviews, if you’d like to connect with our guests, you need to make sure you’re subscribed to our newsletter on our website and we will notify you when opportunities come about. Or you can email me directly at for specific requests. We hope to see you again next week. Take care.

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