UAC 92 | Education And Entertainment Integration


Education need not become boring when integrated with entertainment. This is what Esteban Gast believes in when he uses stories to send his message. Esteban was a touring comedian in his early twenties while making websites and doing other side jobs. He taught creativity at the college level and co-authored Building Your Creativity: Tools For Having Ideas and Bringing Them to Be, a book on creativity. He worked as President of Kalu Yala, a sustainability-focused institute in Panama and was also COO of Scriptd, a script database and story platform that elevates underrepresented creators. Esteban is a speaker with CharacterStrong, where his favorite topic is on kindness. He helped create various web, tv, and film content around masculinity, empathy, civic engagement, and more.

Listen to the podcast here:

Esteban Gast: Intersection Of Education And Entertainment: Using The Stories We Tell To Shape Lives

Our tagline is all about learning how to live a good life. We get to do that each and every time as we drop new episodes with our mantra being, “Finding intention or having intention in the tension.” Life is filled with tensions. We get to live in the middle of those and that’s what being an up and comer is all about. It’s a lifelong journey and pursuit of that same thing. This is an episode that I can’t wait to tell you more about. I wanted to remind you of a few helpful ways that you can give back to us and to the show. One of the best ways is to scroll down in your phone, hit that five-star rating button on iTunes and maybe even leave us a review. If you drop a few notes, Adam and I can read that. That’s a great way to show your support and help more people discover The Up and Comers Show and this community.

The other great way to help people discover is simply by sharing. If you enjoy this episode, please pass it along to a friend or two that could use it or can glean from our guest and the wisdom that he shares. Last but not least, if you wanted to rep the brand, we have merch available on our website. If you go to, on the top of the header, there will be a little tab that says Merch. If you click that, it will take you to our store on Bonfire, where we’ve got shirts, hoodies, tanks and lots of goodies. Go there and grab yourself something to wear and you can officially be an up and comer by naming and claiming it when you wear those shirts. We’ve got some fun things dropping coming up with the 100th episode. Be excited about that. There will be a little special edition and we also have some giveaways coming up, so stay tuned.

This is an interview with Esteban Gast. Who is Esteban? Esteban Gast is an entertainer, educator and entrepreneur. He’s a Colombian who was raised in Puerto Rico and Illinois and lives in LA. He was touring as a comedian at the age of 23, taught creativity at the college level and co-authored a book on creativity while living in Central Illinois. He worked as president of a sustainability-focused institute in Panama. He was also the COO of Scriptd, a script database and story platform that elevates underrepresented creators. He is speaking at schools with CharacterStrong and has helped create all sorts of web, TV and film content around masculinity, empathy, civic engagement, and more. That is a mouthful because he has done a lot and is a fascinating guy. I’ve gotten to know him through CharacterStrong and he is a gem.

In this episode, we talked about so many things, but a big focus is definitely education, teaching and learning. That’s one of his strongest suits and we dive into that. We talk a lot about the importance of relationships, acting to figure things out, social and emotional skills, how to be interested, the different endeavors he’s started on, including his first company. It was a great conversation and there’s so much that he has to give to this world and to share with you. He’s also hilarious. He is amazing. He is one of the funniest guys I know. I was fascinated by a lot of what he brought to the table and what he’s been up to. Before we get in, I did some research and some of the people that knew Esteban described him as goofy, compassionate, authentic, true to himself, great friend, delighted and delightful, and a dream whisperer. If you want to learn from the dream whisperer, you should keep reading. Send us your thoughts and any feedback you might have at We’d love to hear what you think of it.

Esteban Gast, welcome to The Up and Comers Show.

Thank you so much. Thanks for having me. I’m excited.

It’s going to be fun. I love your home. It’s beautiful. I get to see these amazing flowers, which I became a plant owner. I’m learning a lot about plants and you’ve got some beautiful ones around. I appreciate the ambiance.

I wish I knew more about plans to speak to that. They are plants and they are beautiful. I’m probably watering all of them in inappropriate amounts. It’s an effort.

How many have you killed?

I don’t want to speak about that. Failures teach us things. I don’t think I’ve killed any in a dramatic way. There has been mistreatment over time and I’ll eventually google and be like, “Why have I been not watering you or watering you too much?” I’m a big plant person.

If somebody is giving you time, do not waste it. Do it well. Click To Tweet

We don’t ever think about killing plants but it is a serious thing. They depend on us for life. It’s important. I’m starting to take this responsibility seriously.

There’s one takeaway and if people tweet out and they go, “Super great show.” I should be more aware of the plants at my home than we have achieved.

This is another important fact. In research, I discovered that there was a man bun company out there and I’m intrigued. For those of you reading that didn’t know, I was a former man bunner myself. I was rocking a man bun with two of my best friends. It was nice and curly up top. That was probably a good six months strong, so I’m intrigued by this company.

This is the best place that anyone has started because I don’t think I’ve accidentally stumbled into success and sometimes, there’s a TV show and a book. People focus on that and you come in hot with you having to start a company called Man Bun which is amazing. That’s what people want to know. At that time, I was doing comedy and running a design business but both weren’t making that much money. I was like, “What are interesting side businesses?” I don’t remember what I was reading. I looked up Google words and which ones are becoming more popular and that tells you where the cultural zeitgeist is going. I don’t remember who wrote this down but I thought that’s a brilliant strategy for anything. I saw someone tweet out four democratic presidential candidates, here are everyone’s Google searches. This guy, Pete Buttigieg, more people are googling him so that people think there’s momentum. This is an interesting thing for market research.

We were talking about man buns. This was in 2014 or 2015 and I saw man buns crazily spiked. On a weekend, I was like, “Let’s start a business around man buns.” One of my friends, Kevin, had a man bun so I called him and said, “I want to do something around man buns. They’re popping right now. What do we do?” He was like, “Hair ties. I buy hair ties and they’re small.” Kevin is a super big person. He played football. He’s like, “There are no hair ties for men that are big.” I was like, “Great.” I built a website on Wix for free, had Kevin and a few other friends pose for pictures and built this thing. We bought elastic and made larger hair ties. Here’s where it gets crazy. I’m doing this mostly as a joke and mostly because it’s silly.

I was wondering, what percentage of serious was this?

It was 60% silly and 40% curious, “Will this do something?” The first day we launch is Monday because it’s Man Bun Mondays we get featured randomly in a fashion editor from Huffington Post. They send me an email and go, “Can we use some of your pictures for our Man Bun Monday post?” I was like, “Yes.” On the first day we launched, we were featured on Huffington Post because there was nothing. They were only starting. It was ridiculous. It made more money than comedy. I was touring as a comedian and this design business, which we had literal clients where I was building websites for them with my partner.

Man Bun, for a few months, made more business. We hired a friend to make man buns and we had a small team. It was hilarious because we got written up in these feminist blogs that were like, “This is fragile masculinity.” I was in an interview with them and I was like, “I agree with you, it’s silly. The product is silly. You and I agree that it’s silly.” She’s like, “Why are you doing it?” I was like, “I don’t know. It’s interesting to experiment and it makes money. It’s not hurting people.” It was also in Brooklyn Magazine. I’ve spent years of my life dedicated to creating something and in one week, I’m like, “I don’t know. Man Bun hair ties?” We would laugh and high five, “This will never work,” and that gets the press.

What was the lifespan of that?

It was like a shooting star. We were on fire and it slowed. Who knew that creating business over a trend isn’t sustainable for life? There is no business book that told me this. A friend ran it but he was still goofy. It was still making some money and the friend was emailing me, Venmoing me every month being like, “Here’s the third of the profits.” It would be $200 a month for the next two years. I took down the website because I was still getting emails and someone is like, “I bought a bunch from Australia and you haven’t shipped them.” I texted my friend who was running it and he’s like, “I stopped making things.” I was doing customer service and I was like, “I’m so sorry. We’re going to reimburse you.” After that, I was like, “We should stop this. This is an experiment that went a little too long.”

UAC 92 | Education And Entertainment Integration


That has to be one of the best stories we’ve opened with for sure.

The fact that I’ve spent several years of my life in stand-up comedy and this business, blood, sweat, and tears making people a website. I make $5,000 a month more than for the first month but more than anything I’m like, “What?”

Of all things, it is almost the most comedic thing to make money off of man buns. If there’s anything that gets spoofed or played on more, man buns were up there. It was cool because you highlighted all the things that you do in living here in LA. It’s much of a what do you do type of culture. How do you do introductions here in LA? Especially with wearing so many hats, do you have different answers for different people? What does that look like for you?

I sit down and I have a PowerPoint presentation and I go through my TED Talk. I have different answers for different people. One of the things that I’m privileged and lucky to do is have this entertainment tech startup. The thing that I don’t know quite what to say is to someone in the entertainment industry because I’m like, “I’m a stand-up and have been a host of things, but I also have this interesting startup that helps gather and look at diversity differently. It’s almost reinventing focus groups and trying to get a better pulse of what movies will do well.” That’s the situation where if I meet someone, do I go, “I’m someone who can make a show for you,” or am I like, “I’m someone who can help you think about diversity and equity?” Outside of that, if I’m being an entrepreneur or whatever, I have different answers. “I do this.” Sometimes I’m like, “I help people tell stories,” and something that’s generic. That can be anyone that can help someone to tell stories. You help someone tell stories.

It depends on the person and situation, but what is your favorite tagline to use in self-description?

People get it if I go, “Growing up, I liked Sesame Street,” and I’m trying to do that for adults. People get education entertainment or storytelling with a purpose. I’m trying to do Sesame Street for adults. People are like, “I can go with that.”

Let’s start there. This is a huge part of your story and also your work. The intersection of education in entertainment and that is a massive theme in all the people I talked to and with all the research I did of who you are as a person and what you’re striving to accomplish. Where did this synthesis come from?

In my early life, I lived in Puerto Rico and I moved to the US and I remember feeling out of place, which a lot of people feel. One of the reasons I felt out of place was because my name was Esteban or my role as a Latino. There weren’t people with those names doing an interesting thing for it. I often thought growing up, “Am I doing it wrong? Am I doing Latino wrong?” My family is Colombian and we have awesome history there and I’m like, “Am I not doing this right?” There’s no one on TV and popular culture like me.

Looking back at the power of stories that I saw on the screen shape how we live our life. Stories are how we shape the world around us. Being a witness and being part of that shaped me a lot. I had this awesome opportunity to be a high school classroom aid for kids transition out of the juvenile detention system in Lincoln, Nebraska. The best way to engage students is through stories because there’s this performative nature. If stories are how we shape the world around us, there’s a responsibility to be intentional about the stories that we tell. Stories are important and that’s why people like Mr. Rogers from Sesame Street to me, you understand that if someone is giving you time, do not waste their time and do it well. Do not tell a stupid story of like “Do you know what’s awesome? It’s money, power, women.”

Your legacy is you’re going to convince someone to get a nicer car that they can’t afford. With all due respect, go screw yourself. That’s insane. If I go there, I’d think about stories and I thought about teaching. I was lucky to be able to teach public speaking and I taught creativity. I went back and got a Master’s and they asked me to stick around and teach. The reason that they were like, “You should stick around and teach us,” because they would get goodish reviews from people being like, “It’s engaging or you think about a lot.” In the world, there is enough information. It’s people communicating that information. The things we need to learn are not like we’re discovering truths that have never been discovered. The things that you and I need to learn, someone needs to frame it in a way that makes sense to us.

To have someone to bounce ideas and offer feedback is invaluable. Click To Tweet

What’s so cool about Up and Comers and the show is, I read a few episodes and some people I connected with because they’ve spoken through the perspective that I thought and some I didn’t and that’s what’s cool. Those are the different things about guests. There’s someone who is reading and go, “Not for me. Maybe I’ll keep reading.” That’s not how about the world maybe there’s someone who’s like, “That’s how I think about the world,” and they’re learning from all the billion mistakes I’ve made. Communicating information is the key to teaching and education. I’m sitting here and I’m like, “The skillset of being a good teacher and telling a good story is practically the same.” I studied a little bit of educational policy. That was the Master’s and I was looking at education and I have a heart for looking at injustice. I’m like, “What is unfair?” Maybe too much to a fault. I’m like, “Things need to be fair.” Looking at the school system in the US it’s not fair to zip code, funds, and things. I remember thinking Sesame Street or these shows, a poor kid and a rich kid watch it the same.

All these things that I was discovering in school and in a little bit of experience, all drove to this truth. I’m like, “The best thing we can do in education if true equality in education is what we see on screen because that reaches everyone.” That’s interesting. Good teaching is storytelling and a little bit of performance and communicating information. If storytellers have a responsibility to communicate meaningful information, I’m like, “I’m saying the same thing.” Over time, I got more and more focused to where I’m like, “This is the thesis, what do I do with it?” I’ve done all the work on everywhere to be like, “This is what I believe in and this is life’s purpose, which is awesome and terrifying to the point of tears, of like, ‘What’s next?’” I can’t go chasing shiny objects anymore once you know what you want to do.

How many years on the path did it take you to find that refined peace?

Several years and those were hyperactive years where I would go all-in often to the point of not valuing community or rest. Things that I’m trying to be better at and years of hyperactive focused years of my life where I went all-in on TV, went to Panama, traveled, did stand-up full-time and I found it not that fulfilling. I did youth speaking full-time and I found it at times limiting creatively. I went in and in.

It’s interesting to highlight that because this has been a common theme. That path of mastery takes 7 to 10 years for any us in any field. That’s what brings about these simple, refined truths, themes or ideas. I’m going to take this core idea and build off of that. Discovering, finding and creating that skill is a 7 to 10 years process almost universally. I was curious and it aligns so beautifully. The other thing that I would love to highlight from what you shared is, even with the man bun example. You heard advice, saw an opportunity and you took action and you would not have gotten to the synthesis without taking action. Bringing what you’re thinking into the world to experiment with it. How do you think about that or the importance of taking action in that? There are a lot of fears and unknowns in that. How did you think about it before and how do you think about it in this new season of life?

I don’t think I’m smarter or anything. I genuinely, truly do not think that. I act and try to figure things out later. When we look at that season of exploration and that’s from educational philosophy. Learning to me is practice plus feedback. That means that we need to practice. If we can find environments where we can practice and we can fail, it’s okay. That’s fine. If Man Bun failed, I spent $50. It didn’t fail. The net there was, I made a couple of thousand dollars, I had fun and I got to hang out with friends, and do interesting things.

The premise that I look for is, “Where can I practice and where can I get feedback?” Feedback explicitly, in the moment, in every single thing I’ve done, I’ve had a partner. That’s 100% true. The book is co-authored, the classes were co-taught, the design business I started was with my partner at the time and there was a co-working space with a different partner, and Man Bun was with Kevin. I went to Kalu Yala, a study abroad program in Panama. I went and I was president, but it was clear that the CEO and I were working together. I wasn’t a traditional president. I came at Scriptd as a cofounder and CharacterStrong stuff that I’m doing with Houston.

Was that intentional whether you were conscious or subconscious in it and all? What do you see as the benefits of the trade-offs of that and looking back on it?

I genuinely realized this, I’m like, “I need a moment to think about this. Everything has been with our partner.” It was probably conscious and intentional. Maybe I didn’t realize that I did it always. To have someone there to bounce ideas and offer that feedback is invaluable. To think that I know to do things is silly and to think that myself and someone else can figure it out on the go seems a little less silly. It seems a little more like, “If there are two of us thinking through this, at least, we won’t fail that badly.”

There’s undoubtedly higher objectivity. That has to be one of the best blessings of having a partner. You’re not as irrational with two people. One person goes, “You’re pretty irrational at times.” We’re subjective by ourselves and having someone else to raise objectivity can’t hurt.

UAC 92 | Education And Entertainment Integration

Even in that experience, sometimes I think about a lot of, “If this fails, what happens?” A friend and mentor, Chad Songy, who started a bunch of awesome businesses, was saying that sometimes I have trouble making decisions and knowing what’s next. He framed it negatively, which I liked. He’s like, “Which would you regret more?” If you would take one of the jobs here, you’re going to look at the other job and be like, “I wish I were there.” It was an interesting way because I’m usually positive. He’s like, “No. Let’s talk about, if this fails, what happens?”

Up and Comers is wonderful. At least, you and Adam get to hang out and your friendship is deeper. No matter what, it’s a win. You’re a busy guy and for you to build in space consistently with a friend is valuable. With Scriptd, I’m with this awesome woman named Denise and she’s incredible. We spent a year and a half together. Some things were exciting, we had some big wins and there were some frustrating things. I’m proud of everything, but I also got to hang out with Denise and learn from her to build interesting teams. There’s also a component of downside protection. If I know at the end of life, the most important things are the relationships and the love that we’ve shared. That means that this business will be hopefully cool because how fun would it be to pay the bills doing something interesting. If not, how fun would it be to spend time with people that I love building something meaningful even if it didn’t happen?

That’s something that I’ve had to learn because I started everything on my own. It was experiencing the limitations of doing things on your own. You definitely raise your abilities and objectivity by two-fold and fulfillment in life because it isn’t about you. It’s about other people and relationships. I want to circle back on learning being practice plus feedback. In these years of this process of education, entertainment and the intersection of those two, what have been the learning strategies? How do you approach learning in different strategies of the ways you’ve gone about it? What are the different themes throughout the journey that you’ve seen?

This is what we were talking about. They’re amazing. The premise of everything is learning, practicing and feedback. How can we build in learning? To me, a good school is having kids do projects and having them fail in an environment that it’s okay to fail. If we’re looking at protection, how can I take as many risks as I can while being responsible? How can I do that? It’s okay if it doesn’t pan out. For me, I was always interested in acting and creating things. Man Bun, I saw that and it’s a website that anyone can build one on Wix, Squarespace, Weebly, or whoever your sponsor is on that one. Anyone can build a website for free. You can sell things so easily. You can write an eBook and have it on your website. There are times where it’s liberating or it’s a little bit scary, but there’s no excuse.

I would love to host a talk show. In college, I went to my campus. I was at University of Illinois, Illini Union and I was like, “I’d love to host the show. I’ll run everything and I’ll figure things out.” I had a jazz band and I’d come out and do a monologue. They filmed it and they put it on public acts. Many times, people want to help. If that fails, nothing happens. If no one shows up, that’s okay. That was interesting I learned how to manage people and what it actually looks like to do a talk show.

I think of those things as, what is the minimum viable product of this and how quickly can we get there in a way where if we fail, whatever? That’s okay. Learning is practice and feedback. That means if we want to learn, we have an obligation to practice. What that means is practice and do we get feedback. If that’s books, podcasts, that’s real-life feedback, what mechanisms are we building in? The easiest way to learn about business is to start a business. You can start a business that’s not like theirs. You can buy things and all the people talk about this, Gary Vee and all the types. It’s because it’s true. Buy t-shirts and try to sell them online and you learn how to market and you learn how to position things.

One thing that was interesting to me is how storytelling is so powerful and teaching through storytelling. Sometimes people get a little bit jaded because the loudest storytellers are people you hear usually have more marketers than anything else. There’s a key difference between people who are storytellers in teaching versus people who are storytellers in selling. It doesn’t mean that they’re mutually exclusive but there’s a big difference. You do see the loudest and see the most prominent a lot of times are the best marketers, which doesn’t necessarily mean I’m the best storytellers or most helpful people to listen to.

Sometimes storytelling feels achy or intense at times. Sometimes if you see what videos have the most likes or something like that, you’re like, “We’re done as a society. This is it. We had a good run, humans. Pack it in.” There’s something interesting about it as a brand. Donald Miller talks about this. He’s an awesome author. He talks about some stuff about storytelling for brands. Instead of saying, “You are broken by this and you’ll be fixed,” saying, “You’re living an amazing life. You’re the hero of the journey. Let us be the mentor and help you continue achieving greatness.” That storytelling will outlast your broken need. It can help now. There are two sides to that. I also think that aspirin sells better than vitamins. As a storyteller, if you’re marketing this thing. Maybe you struggle with and I can help with it. I think about that a lot because a lot of storytelling is a responsibility. You’re getting to that and there are some people who abuse that responsibility.

It’s not a racket. It’s a business. It’s a responsibility and that’s a different heart posture towards it.

When I watch TV or movies, I’m often, “Why did someone make this?” Being where I’m at, I know how difficult it is to make a movie or a TV show. It is years and years and millions of dollars. Sometimes there’s a show and I’m like, “Why is someone doing this?” Sometimes you can tell because someone wants to be famous or buy another boat. It doesn’t have a heart, it doesn’t have anything. Suddenly you’re like, “This is a beautiful meditation with our relationship with technology.” Someone is so passionate about it. You feel it emotionally. For years, someone has said, “I want to tell the story of how addicted we are to our phones.” This is the way that I’m going to do that.

If we want to learn, we have an obligation to practice. Click To Tweet

If we’re at least present conscious or in tune that we know where what heart it’s coming from. Often we’re not present, conscious or in tune and it all looks the same. It’s being with it and being in tune enough to see. That highlights another thing that I’ve been impressed by you and talking to the people, but also being around you and getting to know you. You are one of the most interested people. How do you see things as interesting? How do you grow seeing more things as interesting? That’s an awesome trait and skill for all of us to strive towards.

James Hunter has this quote, “Don’t worry about being interesting. Worry about being interested instead.” There are fun strategies that I like. I think, “How does Thane’s brain work?” I write and I do think, so for me, there’s an interesting incentive of being like, “If I write a character who’s super disciplined, what does that look like?” Truthfully, there’s probably some selfish aspects to it. I wonder what that looks like. I love the phrase, “Always be a beginner.” My wonderful girlfriend, Jackie, says that all the time.

I love the thought of you can learn something from everyone. Genuinely believe in that. If we believe that, I keep going back to responsibility. Maybe that’s a big theme. If we believe that, we have our responsibility to ask people questions and genuinely see what we can learn. One of the things I talked to young people and with CharacterStrong is, sometimes we say things we believe, but we don’t act them out. I’m super interested in that because I do that all the time. I can talk a beautiful game and if I’m stressed, I’m not as kind and all these different things. If I believe and if I tell you that I can learn something from everyone, that means if I’m meeting someone and I’m tired, I’m like, “How are you?” If you’re coming over, I’m like, “I want to know how you think through things.” I believe that my actions should line up with that, which means, “Let me try to get some wisdom from you.”

Do you have a favorite question?

To see how people think is interesting, which I suppose is once they say something. I’m like, “Help me understand how you got better. Walk me through how you make decisions in your life.” Asking people the why behind things is always an interesting thing. There are fun questions. Usually, I’m writing or thinking about weird things. Jackie and I had a big discussion if guilty pleasures are a thing, should we be guilty about doing things or if we can be, “Actions are good, bad or whatever?”

When we were thinking about that, I asked a bunch of people about that. What that does in a way is to invite them to be part of something. If I ask you questions and we’re hanging out and you’re like, “What?” If I’m like, “Thane, I’ve been thinking about this thing. What are your thoughts?” That for one is a bonding moment. I’m inviting you to be part of the story. We’re in this larger story together and I’m learning, picking your brain and saying, “I respect you enough to think about and reflect on this thing with you.” That’s a fun relational activity of, “I’m thinking about this thing. I love your thoughts.” If there are significant moments, every moment in life is equally significant. I’ve asked twenty people about that.

That’s a great question. What’s so beautiful about that perspective and even the one you mentioned before that on the guilty pleasures is, we accept things at face value that don’t necessarily have to or should be accepted at face value. What do I mean behind what I’m saying? Is that a good or a bad thing? Should I accept the culturally prescribed or should I not? What is my personal call on that versus receiving from others what it should be? It’s fascinating because there’s so much of that in life and it’s an evolutionary type of model that we get better at processing things when we categorize it as already classified as this so we have to think about that. There’s a lot more curiosity in the other, which is a great thing to strive for. What is the conclusion that you guys came to on the guilty pleasure side because it fascinates me?

Jackie believes that to assign guilt to behaviors that we find rewarding is okay. We can reckon with the fact that sometimes watching the Kardashians when we’re tired is okay and we’re not bad people for it. I believed the opposite. Acknowledging that something is guilty doesn’t mean that we feel bad but it acknowledges, “I want to be the best version of myself. This isn’t aligned with that version, but that’s okay.” I’m recognizing that I’m not the best version and that’s okay. I can eat ice cream and hang out. I can refuel and be the best version of myself.

At the end of the day, that’s the same function but a different form. It’s a different form that accomplishes the same function. That’s saying, “Let’s not be in bondage to this guilt. Let’s recognize what it is.” There are different perspectives on what it is but still the same function. What is the guilty pleasure for you?

There’s no such thing. No. There is such a thing. I don’t even know where I believe anymore. I need to work more on guilty pleasures. I want to feel more guilt. I feel enough guilt. I take a lot of naps.

UAC 92 | Education And Entertainment Integration

Education And Entertainment Integration: From an educational philosophy, learning is practice plus feedback.


This is great because this is one of the things that people might not know about you. You’re a great napper. Where does this napping expertise come from? What is the key to a great nap?

First is be avoidant of work and responsibilities and feeling overwhelmed. When I feel overwhelmed, I’ll take a walk but often I want to nap. Sometimes I don’t even nap. I’ll set an alarm for 15 or 20 minutes and be in bed and not think about the work. I do that a lot, as Jackie knows. I’ll be like, “There’s so much going on. I need to nap,” which means lie in bed for fifteen minutes and gather that energy to return to life.

I know you’re not a huge cup guy but have you ever tried coffee or tea naps?

When you drink it and you nap and wake up, I should do that.

I’m the same way sometimes. In those 15 to 20 minutes, you don’t even sleep. You lay there and reset. It’s truly resting. I also hear that there’s something about being in a car that snoozes you fall asleep. That seems dangerous.

It’s when I’m the passenger. I’m trying to be super intentional about sleeping more. There have been times in our life where we are so focused or we’re like, “What’s important?” It’s work. Sleep is one of the things I’m trying to value more. I’m trying to sleep more but I am still underslept so I can fall asleep instantly anywhere. If someone’s not talking to me if I get in the car and we’re starting to drive and Jackie is looking up directions and there’s one minute lull. I’m done and she’s like, “Babe.” I’m still like, “Have I been asleep for five minutes?” I don’t think this is worth it. I’m asleep.

Before we move past education, I’m fascinated by the educational policy. This is such an issue because it’s a system we built and it’s been there, it’s so big and stagnant due to size and complexities. How do you see education and what trends or what direction do you hope or envision for it going?

It’s easy to see where the future should be going. If you look at automation, all of the information is available. This is one of the themes. Every kid can go on Wikipedia and find everything out. They can do calculations on their calculators on their phones and all the different things. The things that schools should be teaching are social and emotional skills which are the ability to form meaningful relationships, so it should be super relational. A teacher is someone who gives you information but also a teacher is someone who loves you, models positive behavior and setups spaces and situations for you to fail and it’s okay.

The second thing is creativity. If you look at it from a global scale, the statistics are insane. There are more English speakers in China than in the US. China has fifteen cities and over ten million people. There are more PhDs in China. Some of these stats may be slightly wrong but I don’t think they’re that wrong. They may be wrong but there also may be spot on right. How do we compete in a global economy? The thing that we are good at is creativity. We’re good at outside the box thinking and the American entrepreneurialism and enterprise spirit of innovation. A startup in a garage, that’s an example of American exceptionalism.

If we look at how to compete on a global economy, that means creativity, entrepreneurship. It’s teaching all of those different things, which means getting away from whatever the test and creating workers who are in a factory doing the same thing. It boils down to relationships and creativity, so it’s social-emotional and creativity because school isn’t necessary. You don’t need school. What is the purpose of school? Everything is the same. Learning is practice and feedback so a school is a place where learning can happen. It’s where kids can practice and be given feedback. If they’re not doing that, the school and educational system that doesn’t prioritize that is going to be in trouble, as we’ve seen.

Don't worry about being interesting. Worry about being interested instead. Click To Tweet

When did you learn how to learn for you personally?

I remember in college thinking I can go for things and by doing that, I’m learning a lot more. I remember this guy that I’m super inspired who’s a good friend, David Schwartz. He started this company called We Are Lions. It’s an apparel company designed and put together by individuals with disabilities.

Did he write a book as well?

He might.

Maybe it’s different David Schwartz that wrote The Power of Full Engagement?

No, this is different. David started this company in sophomore year. I remember being like, “What? You can do that?” He wasn’t in business. I remember that it broke all these paradigms of business students who start businesses. You wait until college is over and you do something interesting. It totally shattered everything. I remember I was writing for the newspaper at the time and I was like, “I want to do a profile on this guy.” I did this profile on him and we became friends and I’m on the board of We Are Lions. It’s a Disney story. I’m thankful and I do nothing on there except be like, “David, I still am inspired by you and I love you to the moon.”

That’s what’s so cool and you’ve talked about this a little bit, but when people do difficult things or when people are pursuing things, it gives you permission and all of a sudden everything breaks down. I’m like, “I can start a business and not be in business.” I don’t have to wait to do that. I don’t have to wait for the right time to start a business. I can start a business. David wasn’t from a wealthy family. I can drop ship and worst-case scenario, I lose a couple of $100 and some hours of time. All of a sudden, every excuse you build up and every box that you put yourself in or in others comes shattering down when a random person who’s studying marketing does the thing, and you’re like, “I’ll do that.” I remember I started doing more stand-up, a fun web series and I started being like, “There are things I’m going to do in this life and I want to get started.”

It is interesting because college was about the same time for me too. That’s probably a common theme because not necessarily us, but that’s a systemic thing from the system. It’s so counterintuitive to the way education is wired. Education is wired to get good at the game of education, which is getting good grades. Education is given and learning is fought for. Learning is a fight. You have to work for it. The way I like to process it, the path of most resistance equals the path of most learning. It takes a lot of effort and energy. Your equation of practice plus feedback is huge in that too. That’s a common theme because of the system and that it’s almost until college we’re finally like, “This is what learning actually is. It’s not necessarily education but it’s possible and it’s more self-driven than others driven.” The commonalities are interesting.

I remember thinking that learning is transactional. Someone would be telling me something and that totally flipped off that it can be me or a group of people doing something and finding out things along the way. No one’s giving me information. No one is telling me that the Civil War started on this year, which is important information to know but that’s all I’ve known is one person stands in front of the classroom and goes, “This and this,” and you’re like, “Thank you for teaching me.” With David’s learning and even following him as he starts this business and being like, “How do you email someone from China who’s your manufacturer?” No one’s telling you how to do that and you’re like, “I’m still learning.”

You brought up something that a lot of people had mentioned about you personally. You referred to what David did in giving yourself permission. That was a common theme. A lot of people mentioned that you are such a great person of giving other people permission to be who they are and to do what they want to do. That’s a cool gift that you developed. Was this the catalyst starting point for that practice for yourself and for others? Talk to me about that part of your personality or what you strive to do.

UAC 92 | Education And Entertainment Integration

Education And Entertainment Integration: A teacher is someone who loves you, models positive behavior, and sets up spaces and situations for you to fail and it’s okay.


That’s generous. The people are nice. If you look at it statistically, the fact that we’re not hungry is 40% of the world. We’re in the top 60%. The fact that we have homes kill another 30% so we’re in the top. The fact that we went to college. We’re talking about college when it’s time to do that. In the game of life, we have won so much. It’s an unbelievable margin. There are people running a marathon and we’re at the last mile and we can see the finish line. There are a few different things in terms of encouraging people. When someone is like, “I’m thinking about doing something big or I’m taking this leap.” I’m like, “You’re made to do your incredible things.” I don’t think anyone is made to do anything small but also, that’s an uplifting way. It’s also a statistically significant way. It’s like, “You have such a gift and you’ve been given so much in such a gift.” Instead of giving the privilege like, “If you want to make candles instead or sit on a desk.” Not only should you try that, but you’re right to try that and you are doing a disservice if you’ve got this thing in your heart that you’re not going for.

I feel like the luckiest person. My parents set some money aside and I got a few scholarships and I graduated early to not keep paying college. I have no student loans. I have friends who are paying $2,000 a month. I’m living in this nice house for basically that in student loans. I’m like, “I don’t know. That thing scares me.” I feel like the luckiest person ever and what that does is, it motivates me to be as generous as I can and go for things as boldly as I can. It’s easier said than done. I still live in fear and have all these blocks for myself. It’s easy to encourage people because people are remarkable. They can do more than they believe. If someone is asking me, “Should I go for this thing?” I’m like, “Yes.” You’re asking me and you’re sitting in a car from your job. The gifts that we’ve been given, let’s do something with that.

When I ask people to describe you in a couple of words, one of my favorite ones was dream whisperer. That’s a cool categorizing of what that was. When someone shares a dream, you’re like, “Do it.” You’re whispering to them to do it. In giving permission, do you find it easier to give permission to others or to yourself? Which one is harder?

To others, it is so much easier.


I love this saying, “We teach what we most need to learn.” “Wise people take their own advice.” I’m in a unique position with speaking at schools or doing whatever. I’m often giving advice. In almost every time I do, I’m like, “I’m often if not, the majority of the time, horrendous at taking my advice.” I would need to listen to me a minute ago, encourage myself and be like, “You’re right,” because I’m still paralyzed by all of that, which is the reality of that. It’s with others because I have a few blocks from me. One of the things I’m doing is going to meetings, TV shows, web series with me and it feels ego which is goofy because it shouldn’t. I’m going into meetings and it feels weird to be like, “Do you know who you should buy? Me.”

With Scriptd, we have all this database of underrepresented writers and I would go in and sell who they are and how talented they are. That was a lot easier for me. There are weird blocks there that shouldn’t be there and I need to overcome, especially if I want to find any means of success. Also, maybe the curiosity thing. It’s awesome to hear people talk about the things that light them up. Especially if they’re not doing it and you can see them imagine this version of themselves or of the future where they do it. That is so interesting and beautiful. That’s such a gift that people allow you to know what their heart truly is about. I want to dive in there and that’s much more interesting to me than myself being like, “What am I about?” That’s where I usually go and take a nap.

Who was the person or the people in your life that gave you permission? Who were those dream whisperers, if any, for you?

There are so many. I feel so lucky that Jackie is someone that I’d like to spend my life with and to have a life partner who encourages those whispers is one of the most valuable things. Also with everyone and friends too. I hope that you and I as friends are always like, “Yes. Thane, you’ve been given so many good friends.” It’s a seemingly natural disposition, discipline that I admire. I’m sure that the truer stories are more than natural. In anything you do, you’re the best learner so you’re going to be fine. You can be like, “I’m going to do something that’s totally the opposite.” I’ll be like, “Great.”

If you’re fired up about that, I’ve got full confidence. It’s also the people we surround ourselves with. I’m ridiculously grateful to say a bunch of people. Specifically to Jackie, who is next to me. My parents were supportive. They were super supportive. Sometimes they weren’t always as informed. They’re Colombian immigrants, they don’t know quite how the comedy system works. There are funny things where my mom is like, “Write to SNL.” I’m like, “It’s a little more difficult.” I’m thankful because as the son of immigrant parents, many people in my position are like, “They want me to go into this path.” My parents nudged me here and there like parents are supposed to do. They have resigned to the fact that I’m living a strange life and they love me and support me through that. What a gift to have parents for me to be like, “Mom, dad, I’m pitching these web series where I’m talking about blank and I’m pitching this TV show about blank.” They’re like, “Great, we love you.”

Comedy offers often a redemptive take on things that haven’t gone as planned. Click To Tweet

That is such an important perspective or lens to view the world from. We all have the ability to do that. We all have the ability no matter where we’re at to see life as a gift and not gain. There’s a great book I read called Living Life Backward. It’s summarizing in more modern form the book of Ecclesiastes from the Bible and King Solomon’s wisdom in that. A lot of it is vanity. If we chase after the wind, we don’t realize it’s about people. It’s saying that we all have the ability and power to view life as a gift and use it as such. That’s an empowering place to be, regardless of where you’re at. Everything can be viewed. That’s our choice and our responsibility, as you were saying.

If you have one person who says, “You’re a capable person.” All of those are gifts. From there you start finding more people and you start putting and bringing some of your ideas to life and having more people be like, “You’re capable.” Even they felt like, “You’re someone who does things.” That’s amazing. Most people don’t even do the things you’re doing. I love those perspectives. We’re not saying anything revolutionary new but hopefully communicating the same ancient wisdom of having a choice of how to see it. I could also make an argument that there are not enough people who believe in me. That’s a compelling argument I can make.

In Hollywood, the majority of things are rejections. I can talk about all the times that people are like, “No, you’re not handsome enough,” which is ridiculous or, “You’re not Latino enough.” “You’re not white,” all these different things. There’s a compelling argument to be made that there are not enough people who believe in me. A much more interesting argument to make, one that will result in happiness is, “Many people believe in me.” That is the greatest gift I could ask for.

It is powerful. Education is a huge theme here. One of the things that I was fascinated to learn about in research, but to know your perspective on is Kalu Yala. This is an amazing endeavor. For people who aren’t familiar, which probably most people aren’t, maybe a little snippet about what Kalu Yala is. I would love to know about your experience there and what it taught you about education.

Kalu Yala is an off the grid sustainability institute. It’s basically a study of broad program for college-age students. It’s literally off the grid. There’s no hyperbole. You take a three-hour bus into a small town, and from there, you walk a three-mile path and you’re in this community. It’s sustainable so we have our own farm, solar power, hydro-power and we have all these different things. It’s built around a few different principles. If there’s a thesis on a lot of the things I’m doing, one of the takeaways is experimenting. Where can we practice and receive feedback?

What we’re doing there is we’re experimenting. We’re practicing what civilization looks like differently. What does a city look like when it’s completely sustainable? Is that okay? Do we miss things like peanut butter? We had this local economy. We had a coffee shop for people. We played around with currency and all these different things. One hundred college-age students come there every semester. There are 50 staffs to run a whole town. We have different people like professors, tourists or retreats come down and people maybe are there for nine months during research. It’s an amazing place. It’s super vibrant with tons of interesting young people who are all dedicated to exploring what life can look like in this utopian place.

The truth is that it is complicated. It’s no utopian but it’s interesting. I learned so much. I was lucky that I had the honor to be the president there and work closely with the CEO and Founder, Jimmy Stice. I was there for a little over a year and it was awesome. I got to hire a bunch of people whom I love and trust. I got to see Kalu Yala through an interesting evolution. We were growing. We started this incubator for people to start businesses, which was phenomenal. I’m a social capitalist so I was also interested in testing out these theories of capitalism for good. What does that look like? Which was interesting.

It was such a dream. If you were like, “Let’s design a city and a town. Here’s what I believe living should look like,” and you go and do it. It was fascinating. From there, we got a Vice TV show from some contacts that I had in the entertainment industry and some people that Jimmy, the Founder, CEO knew. We all got together. Ondi Timoner, she won sundance a few times and had a movie premiere at the south. She’s a phenomenal director. She came down and we made a show for Vice. It’s called Jungletown if you want to find more about stuff. I was super lucky to be there during this period of time and it was awesome. I lived in a tent for over a year. I walk to a clean water source to brush my teeth every morning and night. It was the Panamanian rainforest, which is rain so I was there during the rainy season where it rains all day. You’re in a tent working on the farm. It’s funny because I was president but it was a community living. On the farm, I’m doing everything.

It’s fun talking about now, but there are incredible highs and lows. What was that low point on that trip or that journey?

There was a lot of being in nature and being away from everything. We’re obviously away from phones, technology, family and community. There were a lot of emotional highs and lows for people who felt free and they missed their community. Life is difficult when you have to prepare your food. Often you have to walk everywhere. Even brushing my teeth I’d have to walk when it’s raining and I’m sad. You’re walking in the rain to the water source to wash your teeth. There were a lot of emotional lows, for myself and for the people I love. That was also tough.

UAC 92 | Education And Entertainment Integration

Education And Entertainment Integration: Acknowledging that something is guilty doesn’t mean that we feel bad in it. It acknowledges it isn’t in line with the best version of yourself in that moment but that’s okay.


A few people left because they were going through such a tough time. There’s no mental health infrastructure. We had a counselor but that was it. Some people who had more serious issues and were like, “I need to go and get prescribed things and see a therapist who isn’t a counselor.” It was all these things. For me, some of the lows were myself being in those places, and also having people I know and love, friends and best friends being like, “I need to leave. I can’t do this.”

The other thing I was curious about is, what is a belief that you formally held that you no longer believe to be true after the experience?

One of the things that I talk about and I talk about it a good amount because it comes up is, I went there and I was a meat eater and I killed a cow and a pig. It was horrible. I remember I was talking about it at breakfast and I said, “I killed this cow and I went to the bathroom and cried.” I don’t eat cows or pigs anymore. I don’t eat red meat. I killed some chickens and I felt okay about that, so I eat chicken occasionally, but I want it to be an ethical chicken. If you haven’t killed an animal for meat, it’s one of the most powerful things. In one instance, it was a 10 or 20-minute thing and it changed my life forever. I often think about that, “What are twenty minutes that can change your life forever?” Which was a beautiful thought and truly going to a farm and being like, “I don’t know if you do this, but I’d love to see how you kill cows ethically.” That was such a powerful experience so that’s one.

The other thing is, the TV show taught me interesting things that I think about in terms of storytelling. Sometimes the audience doesn’t understand complexities and how to do a better job at communicating that. I was like, “I’m a social capitalist.” There would be blogs that are like, “This guy’s in it for money.” I’m like, “No, I don’t think that at all. CEO pay should be capped.” I agree with your policies, people who are yelling at me. I want to tell interesting and complex stories, but I also see that people were like, “This guy is this.” It’s a study abroad program so people pay obviously in a way reduced rate. It’s something like $3,000 for a semester, which is great. We would have them work because they’re in a program in agriculture, so you’re going to be on the farm.

You’re not going to work as a worker. We had workers but you’re going to be on the farm and work alongside the workers once and get to see what that looks like. People would be like, “They’re paying you $3,000 and they’re going and working.” I’m like, “I believe in project-based learning. There are projects and everyone has projects.” I also could probably get better at taking criticism, especially from online trolls. Maybe that’s me, but a belief that I had before with the show, I said, “Let’s tell complex and interesting stories. Let’s talk about the fact that capitalism and businesses can be a force for good and you can coexist in this thing.” There can be capitalism that Bernie Sanders high fives and goes, “This is great.” Even for democratic socialism where we’re saying similar things in different things and I believe in the power of business. Let’s use these terms.

People aren’t going to dive into the fact that I can give a mini thought on how I believe capitalism works and should work. We were there for Trump’s election. I spoke up against and I said, “Trump’s election is the fact that we’re not talking with people we disagree with. If we have conversations with people who agree with this specifically around climate change or environmental causes, we’re not doing much.” We have a responsibility to reach out to people who don’t believe that the climate is changing. Let’s have those conversations because to exclude them does nothing except get more riled up. We don’t speak to them in a way that respects or honors them in any way, even their humanity. I can love someone as a human and disagree with our view.

I spoke up and people were like, “You’re going to give a platform to climate change.” I’m like, “No. I’m never saying that. For science, we communicate science differently.” I’m going on a tangent, but the interesting thing that I learned and I’m thinking about are these interesting points with a few different video projects that hopefully I’m signing and stuff is happening. How do we tell those stories in a way where people look beyond the boxes where they’re not like, “That’s a word I don’t like.” Maybe I don’t need to. I have a ton to learn but maybe what I need to learn is not to ignore the people who go for the lowest impulse and lowest triggers of, “You said this.” I was disappointed in the show’s ability to talk about complex things in people. What I saw in the blogs, reviews, and things is the inability to understand that the world is complicated and it’s all shades of gray. It’s never black and white.

That’s hard. Since it’s a two-sided coin, you can only control one side of the coin. You’re trying to influence both sides, but ultimately you can’t change both sides. You can only control one, which is yours. How can you help influence in a positive way? The other side is always the ongoing question because complex things are that complex. There’s a great quote, “For every complex problem, there’s a simple solution and it’s always wrong.” I get that it’s complex. We’re going to have biases and we’re going to view things from our bias. How can we get outside of our bias to see things from other perspectives and empathize? Those are learned and practice skills.

“Is Vice too general? Is there a specific show that goes for a different audience where I can frame let’s say climate change in this certain way? Is there a show that’s for a more general audience where I can frame it in this way?” Those are the thoughts rolling around in my head. I thought it was a one size fits all. There are people reading this blog. I’ll take responsibility for that as a storytelling error on my part saying, “Let’s tell this story and assume everyone’s at this point,” when people aren’t at that point, and that’s okay. That means, let’s find where those people are at, meet them where they’re at, tell them an interesting story that they resonate with in terms of the dangers and threats of climate change in a way that flips the script and some things that they’re like, “I’ve heard this.”

That’s the layers of our responsibility. It’s something I’m learning more and even in my own work or realm is, we see things so clearly from our perspective but no one else sees it from our perspective. How do we bridge this gap between our perspective and their perspective so that what we see can be hopefully communicated and received from the other perspective? Where does that middle gray area between the two that’s most helpful for both sides? It’ such a dance. I want to talk about what comedy has taught you about education. That’s an interesting piece. I feel that hearing from other comedians on different shows is fascinating. Comedy seems to teach us about life. What has comedy given you?

Comedy and curiosity are linked. Living a curious life is one of the best things you can do. Click To Tweet

It has given me so much. Many nights in a crowded bar where no one listens to me is the first answer. What a gift it has given me. Comedy hecklers, who go, “You look like a property brother.”

What’s the most creative heckler you have gotten?

I remember a drunk girl saying, “You’re not as cute as you think you are.” That hit hard. She could have said, “You’re not that cute,” and I’ll be like, “Okay,” but “As you think you are.” You’re like, “Am I not a seven? I thought I was seven.” I remember that one. It was in Baltimore and I was like, “Classic East Coast.” You associate the whole town with that heckle. If I go to Baltimore, I remember, “You’re not as cute as you think you are,” and just going to yell at me. Comedy offers often a redemptive take on things that haven’t gone as planned. I love my friend Mia Baker, she’s the best. She has this production company and she is a super talented producer. I don’t know where it came from, but she had a sticker for her company and it said “What doesn’t kill you is content,” which is a ridiculous quote I don’t know if I fully agree with but it is a good quote. There’s no denying.

I remember when I was dating back in the day before I found the person. On a bad date, I’d be like, “I can talk about this on stage.” I remember touring and doing traveling a ton to do comedy shows, when something would go wrong, I’d be like, “That’s okay. I can poke about this.” Comedy is forced levity for any situation. They’ll say like, “The rental car people ran out of cars but I rent it.” That’s going to be frustrating. I can be like, “That’s what you do.” That night would be like if I’m a comedian and I come up and I go, “Sorry. There are no jokes.” You’re like, “Why are you here? I don’t understand why you’re a rental car place where I rented a car.” All of a sudden it’s this opportunity to take things not that seriously.

Comedy has been incredible in that. I love thinking about that. In what we were talking about, you also get interested in things. You have to be a tourist everywhere you go with everyone. If I’m walking in my neighborhood and for someone who has this comedy brain literally walks in as a tourist and goes, “Everyone has fences. Why are we obsessed with fences?” From there I’d be like, “It’s so weird. We all have fences but we want to be a community and these fences are stopping it.” Go and go. Comedy and curiosity are linked. They’re the same family. Living a curious life, it’s one of the best things you can do. Comedy is the outlet for curiosity or an outlet that is silly. I want my curiosity to be expressed in silliness.

There’s a great quote I heard that speaks to it. GK Chesterton said, “The traveler sees what he sees. The tourist sees what he has come to see.” That’s a beautiful way of saying it. You were referring more to being the traveler of seeing what you’re actually seeing, not seeing what you’ve already come to determinately see. That’s definitely a practice. It’s not a default position. What has been the hardest to develop for you as a comedian?

The way that the comedy industry is a little bit old school or a hierarchy. I was telling this to Zack who’s been on the show, the manager of Yes Theory and an overall awesome person. Comedy club owners would say, “Don’t talk about your social media at all on stage. That’s not how we do things.” I was like, “I understand it’s getting in the way of jokes or maybe people are pitching themselves too much.” I’m like, “In that process, I have been everywhere in the career and I don’t have a big following.” The comedy club owners have all the power because they tell me when I go up. They tell me, “We had you already. Email me in a few months.” I don’t have that big of a following where I go, “I’m going to do my own show, but I’ve performed in front of hundreds of thousands.” This doesn’t make sense.

What I’m frustrated by the obstacle of trying to maneuver the business side of it wanting to do good content and not wanting to go rogue. That isn’t the intention but to be like, “How do I maneuver an old school system where there’s a gatekeeper? I tell you when you’re on stage and it’s my preference?” How do I do that while still acknowledging the future, I don’t think as gatekeepers? I want to have a long and sustainable career. That means I’m not only thinking several months but I’m also thinking of 6 to 20 years when I have kids and want to not be on the road always. What does it look like to make a living being silly? Is the gatekeeper going to determine that for me? I resist that. Any gatekeeper thing is rigged.

What I’m doing in LA is trying to maneuver that. There are some clubs that I have good relationships with, mostly in Chicago and St. Louis. What does it look like to do comedy in a thoughtful way? I’m super thankful that I got a little bit of that business acumen so I can take a look at it a bit more objectively. Take a step back and say, “The system doesn’t make sense.” What does an alternative system look like? How do I develop a comedy career by having one foot in the system, that’s okay and one foot outside of it doing the things I want to do and not waiting for an old guy in his 70s named Wally to say, “You can get on stage and I’ll give you $50.”

One of the other things that someone brought up is a cool perspective on what you’re striving to do in comedy. They said, “I love how he does comedy and how he approaches comedy in this new wave of comedic entertainment. Not the dark humor of old and how much life sucks, but more of a positive, ‘You can be funny without being so dark and crude.’” Talk to me about your approach to comedy and your reasons behind the way you approach it.

UAC 92 | Education And Entertainment Integration

Education And Entertainment Integration: Learning is transactional. It can be a group of people doing something and then finding out things along the way.


If someone heard that, they’d go, “That makes sense.” There is an argument that can be made and I can get on stage and go, “I woke up and I was tired. Why do I have to get out of bed?” Go into that. There are these comedy people like Josh Gondelman who released a CD or a record. He’s amazing. He writes for Last Week Tonight. Pete Holmes is a great guy. They’re my heroes in the way that they and I hopefully look and go, “Life is ridiculous.” If things go wrong, that’s a ridiculous circumstance. That’s not someone out to get me or not like the whole system is messed up.

For me, what’s beautiful in comedies is you’re sharing your perspective on life. People are pretty familiar with my perspective. It’s the same power source when I’m plugging in a blender or a toaster. I’m plugging in the comedy to this hopefully, deep-seated belief that life is for us and it doesn’t happen to us. What does comedy look like from that lens of, “Yes, there are ups and downs and all these things.” The human experiment is the goofiest and most absurd thing that has ever happened in the history of time.

We’re these weird hairless apes walking around lost that our own thoughts and distracting ourselves by our own thoughts. Every other animal, it’s like, “Meal,” and we’re like, “What is ease?” We sit right there, plug in that power source and it takes this shape or I plug in something else that’s not a comedy. It’s a more serious form of storytelling. It’s still the same as, “This is a gift.” There’s still work to do. Let’s go out there. Let’s do the work. This is a gift so walk with that knowing that.

What’s the most ridiculous thing you’re exploring?

I have a notebook where I’m always writing ideas. I’m thinking a lot about social media, which is great. For me, everyone became this branding machine. It’s so good that people are writing PR releases to go to college. Have you noticed that? Do you have a younger sibling and they’re like, “I am delighted to announce that I am taking my talents to the University of Miami.” It’s like my cousin and I’m like, “Why are you writing this way?” I’ve thought a lot about that and I’ve been super lucky. I’m writing a show dealing with the difference between our public life and our personal life and what happens when you commodify your personal life, which we’re all doing in social media. There are beautiful takes on that and maybe more cynical. That doesn’t mean that I ignore the good parts but the perspective I’d like to share is, “This is absurd.” Teens are little PR agencies being like, “How can I frame this?”

That’s one thing that I’ve been talking a lot with friends about. It’s going to be fascinating in years what we think when we look back at this time because it is bizarre.

We’ll be like, “Who are we performing for?” There’s a Thane person and there’s a Thane brand for coaching and things, but the people who don’t have it like a normal seventeen-year-old who has an Instagram almost similar to your brand one. You’re writing copy for your social media like it’s lead generation.

That’s the thing that’s tough because it’s not understood on both sides of difference. It’s only understood on one side that’s the difference between that consumer versus a producer. It’s the same platform but two different intentions behind it. It’s not originally intended for that either, so it’s a business adaptation to it that creates that weird tension and pressure to follow suit. It’s fascinating. I want to touch on one probably the most common theme in talking about who you are. I’ve definitely experienced this. A lot of times, I ask people what do people not know about Esteban? Most people that know you will agree that they know that you care about others and you give a sense that you care. Someone said that they don’t think that others know the depth of care that you have for other people to succeed. This is a quote, “Even though he’s a showman and often the center of attention, his biggest goal is always to make other people feel empowered.” What is the motivation you’re in your relationships and your generosity to others? Where does that flow from?

I love that quote because that’s aspirational. That’s what I try to do even if I’m on stage. Hopefully, the goal is often to have people feel seen. There’s this quote by Junot Díaz that I love. He goes, “Vampires can’t see themselves in mirrors.” That’s an interesting character trait and a fundamental level to deny someone a reflection makes them monstrous. As a society, we don’t even have a reflection for them. What I’m trying to do at times with the stories I tell and hopefully maybe the perspectives that I shared is providing a mirror for those who don’t feel that. Maybe people feel slightly less of a monster.

I talked about growing up, and I felt like, “Am I doing it wrong?” No one is like me and I didn’t see myself in the mirror. At a fundamental level, that dehumanizes me. What does it look like to humanize people by telling their stories or by being this mirror for them? What does it look like to humanize people by acknowledging that their story matters? That gets into the why of growing up. There’s no way that I’m more important than anyone else. If I’m in front of a stage, that means I spend a lot of time doing that and enjoy it but there’s a recognition in that. People facing me doesn’t mean that I’m the most important person in the room. It means that the room is set up that way.

Helping others is the way to be happy. It’s also the best tool to remember this life isn’t just for us. Click To Tweet

I understand there are roles to play and most people would be like, “How do I do that?” I think a lot about that. When I speak to young people, I think about how to deliver everything I’m doing but also making consistent eye contact. These are things I literally practice. I’m in my hotel practicing and moving my head around different areas. I don’t know what the answer is but that’s beautiful that people say that. They were spot on the vision, ideally. Sometimes if often than not, I fail but that’s the vision. The vision is to create mirrors for people.

What would you say are the cornerstone habits or the things that help you practice that most consistently?

It’s the habit of listening to other people and supporting other people. Nothing reminds you that your goals are as worthy as other people’s goals as you cheering on other people’s goals and trying to build in space for that. Houston Kraft is a mutual friend of ours and he does a great job of sending texts every day to different people. I’ve copied that and literally stolen that from him of being like, “What does it look like to check in with people?” Maybe have a slight system where I know what some of my friends are working on and I can check in here and there. Life is absurdly busy. That doesn’t happen as often that I like, which is always important to acknowledge. Helping others is the way to be happy. It’s what we should be doing. It’s also maybe the best tool to remember that this life isn’t only for us. It’s interesting to have all of the truths rolled up in the fact of being of service to others or sharing the love with others.

I remember one of my friends would send me an audio message of her praying for me. It was so powerful and impacting to me. That’s one of the things I love doing. I’m sending morning encouragements by texts or praying for someone over by voice message. It’s so life-giving to do not only to receive but to give. What is the vision for Esteban? I know that a lot of people that I talked to were curious of what is that future vision you see.

I’m in this interesting point where I’m clarifying exactly what those next steps are and what it looks like. If we look at the last few years, having all these experiences and experiments like the minimum viable product. The first iteration, second iteration and doing all these different things. They’re saying, “I’ve got a little bit of business, storytelling skills, and a resumé. There are TV shows for comedians and all these places.” If the point is to think, “What does this look like and what shape does it take?” I don’t know, which I’m glad that this is Up and Comers. What it does is it implies that I’m getting started.

This isn’t the, “If you’ve reached the high heights, you’ve arrived,” show, which I appreciate, which is also why I’m like, “I’ll do this.” I truly don’t know how much wisdom I have to share. It’s interesting to have someone be part of the journey and go, “I’ve done these things. They’re neat.” I’m figuring out what’s next. There are interesting projects with CW and with production companies that I love like Wayfair Entertainment is incredible. They do awesome storytelling. There are things that are happening and I’m like, “What is next? What’s the big project?” Sometimes it’s easy to not know what you’re passionate about because you don’t have an excuse. I’m like, “This is what happens. Let’s get some skin in the game.”

Commitment is always scary too. To off that a little bit, what would be that legacy that you’d want to leave behind when it’s all said and done?

I gave people a space to feel, seen, heard, and loved in whatever way that looks like. Stories are an interesting way but also hang in with them. If at my funeral, no one brings up anything professional, I’d be all right with that.

That definitely fits with the feedback. What are you most proud of so far?

I went through some pretty major setbacks as we evolve usually in the twenties. I’m proud of how I pulled through those and how I’ve built a life. The great relationship that I have with Jackie and the home that we have, the finances, and everything. I’ve been in not great relationships, not a good financial situation and haven’t thought about things. It a lot of different things. I went through those difficult moments and learned. I’m hopefully learning from those and saying, “This is the base level of relationships, communication and loving.”

UAC 92 | Education And Entertainment Integration

Education And Entertainment Integration: Sometimes you need a kick in the butt and sometimes you need someone to tell you that you’re amazing and you’re worthy.


That’s always going to be the case for us. It’s being proud of getting through some of the lowest lows, not necessarily getting to some of the highest highs.

I wonder if when we’re in those lowest of lows we remember that. I’m going to look back and be like, “I’m so glad that I lived through that.” Those lowest of lows provide a lot of meaning.

What questions do you ask yourself the most?

The juxtaposition of what the world needs and what I am skilled at or what stories I want to tell. I’ve made a list in my journal. I’ll go like, “Here are things and topics that we should be talking more about.” I’ll go, “Here’s a quick story that I can speak to that.” I do that in a good amount. That’s also a good equation and there’s a ton of advice around that, but it’s like, “What does the world need and what am I uniquely equipped to speak to those challenges that the world needs?”

If your body could talk, what would it say?

It would go, “Sleep a little more, not only naps.” They’d go, “Don’t spin this story about naps. They’re not enough.” They’d probably be like, “Slow down.”

If you had unlimited resources, what frivolous thing would you collect?

I like car and shoes. I often think rich people don’t spend their money well. Over 50% of schools don’t have a counselor or social worker. I want a Social Worker Project.

What books have had the biggest impact on you personally?

There are two creativity books in which they’re both on the opposite ends of them combined. There’s a book called The War of Art by Steven Pressfield. It is so good. It’s like drill sergeant creativity. I grew up with a tough Latin mother, so I’m used to someone yelling at me and I respond well. There’s this book called The Artist’s Way by Julia Cameron. It’s a hippy-dippy, spiritual, creativity’s tapping into life source. Both of those are interesting. I revisit both of those a lot specifically that I’m doing more explicitly creative things. I look up passage all the time and they’re both different. I’m in the middle of that. I’m like, “Drill Sergeant, get stuff done. Let’s go.” I’m also like a little hippy-dippy but let’s see what feels good. I love both of those in certain moments. I don’t know if those are the two books that I’ve changed, but there are two books I’ll rank up.

I have The War of Art on my bookshelf. I haven’t dived into it yet. I love having those two sides because in life, there are always two sides of the fence. It’s that tension between where the beauty is and getting books on the same subject on both sides of the fence are so helpful.

That should be an interesting show where you go, “Here’s a book on business success. This book is about discipline. This one is on relationships.” What I like about both those books is, both are true. Both have helped me and will probably speak to the readers but different situations. Sometimes you need a kick in the butt and sometimes you need someone to go like. “You’re amazing and you’re worthy. Take some time and the ideas will come to you.” Sometimes it’s like, “Sit down and write.” Both are good.

That’s why we have our mantra for the show, “Having intention in the tension.” That’s life. There are inevitable tensions that we have to live within and the goal is to have intention within those. If you could send a morning text reminder to every Up and Comer out there, what would you say and why?

The first thing that comes to mind is, “Your story matters and you matter.” The second thing, let’s assume that the Up and Comers have a little bit of self-confidence, I would say, “Do that thing and figure out what that is.” I don’t think it’s a big thing. I have no idea what these big projects and life projects in my life are, but I did the thing with Man Bun and it was interesting. I did the thing where I wanted to get out of the country and do something interesting in education. I’ve done the thing and learn from it. That’d be super awesome if every Up and Comer was like, “Do the thing.”

Esteban, this has been awesome. Where should people be on the lookout? Where should they find more about you? Where should they connect to that?

My handles everywhere are @RealEstebanGast and I’m trying to post silly things on Instagram. That’d probably be the best way. They’re silly expressions of creativity and trying not to think about it. That’s a place where if it’s something that makes me laugh, it’s up there. There’s hopefully some interesting web series stuff coming out of that. I haven’t fully figured out and can’t talk about it. If you’re interested in education, entertainment, that’s what I’m doing. It’s going to be interesting stories. Thanks so much. This was a blast.

Thanks for coming on. Until next time. This has been awesome. Keep up the great work. I’m excited to see what this new season unfolds for you.

It will be good. Thanks.

Important Links:

About Esteban Gast

UAC 92 | Education And Entertainment Integration

I speak, both silly and serious, at middle schools, high schools, colleges, comedy clubs, and conferences. I taught creativity at the college level. I co-wrote a book on creativity. I ran a school in the off-the-grid jungle. I was COO of an entertainment tech company focused on diversity in Hollywood. I was on a TV show that aired on VICELAND and A&E. I started a few businesses.  I’m still figuring things out.

I speak at schools, colleges, conferences, and corporate events. You can find more at Kirkland Productions. For the past few years, I’ve been working with CharacterStrong speaking about kindness and I love it. I’ve starred in a TV show and a web-series made videos for companies, non-profits, political organizations and for fun. It’s been a blast. I’ve been featured in NPR about “soft skills” and Huffington Post about creativity and lots of local press for things as diverse as being a stand-up comedian and being a fan of Pluto the planet. I’ve written some blogs for Medium that mean a lot to me. Here‘s one of the more popular ones.  I also co-wrote a book on creativity. You can find it here.

Follow us on the Socials!
– Instagram
– Facebook
– Twitter

Check out our YouTube!

Leave us a Rating/Review!


Send us an email – theupandcomersshow@gmail.comEducator, entrepreneur, and entertainer, Esteban Gast shares how stories are the best integration between feedback and practice.