The Smartest Way To Be Stupid with comedian Matthew Broussard

If you feel stupid while learning something new, you’re doing it right. But if you keep doing the same thing over and over hoping it’ll suddenly make sense - that’s on you. The trick isn’t to push harder; it’s to find a new teacher, a new explanation, a new way in. That’s exactly how Matthew Broussard approaches comedy - and everything else. A stand-up comedian, math nerd, and former financial analyst, Matthew is obsessed with learning and cracking the formula behind how things work. He treats every joke like an equation, testing, refining, and solving for laughter. He’s the creator of Monday Punday, a puzzle webcomic and app, and has been featured on The Tonight Show with Jimmy Fallon, Conan and Comedy Central’s Roast Battle. He’s also made appearances on The Marvelous Mrs. Maisel and The Mindy Project. His storytelling, including his viral tales about his mother-in-law, proves that logic and vulnerability can live in the same sentence. In this episode, we explore the overlap between comedy and leadership—the art of experimenting, iterating, and connecting through honesty. We talk about the hidden work beneath success, the difference between purpose and perfection, and why laughter might just be the purest form of optimism. This is A Bit of Optimism. --------------------------- This episode is brought to you by the Porsche USA Macan --------------------------- Check out Matthew’s Youtube page for his full comedy special “Hyperbolic”: https://www.youtube.com/@mondaypunday ---------------------------

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  My love for math and my love for comedy and science, I don't think they're separate entities. I was not an artist by training. I think an artist creates things whose value is measured subjectively. Stand-up comedy specifically sits at an odd intersection in that you could almost not qualify it as art, because every decision I make is focus grouped in real time.

• 0:21Simon Sinek?

  It's empirical.

• 0:21Speaker 00

  It's extremely empirical. I think that was my draw to it.

• 0:25Simon Sinek?

  And instant results.

• 0:26Speaker 00

  Instantly.

• 0:27Simon Sinek?

  Like math. The math, the solution is revealed in that moment.

• 0:30Speaker 00

  Yes.

• 0:30Simon Sinek?

  And comedy, the solution is revealed in that moment.

• 0:32Speaker 00

  Hypothesis, conclusion, in a heartbeat.

• 0:34Simon Sinek?

  In a heartbeat.

• 0:35Speaker 00

  In a heartbeat.

• 0:36Simon Sinek?

  I was surprised when I invited a comedian on the show that we would spend so much time talking about math. But it's to be expected. Matthew Broussard is a former financial analyst who, let's just say, got forced into stand-up comedy. I found his work on Instagram a whole bunch of years ago and am a huge fan. He's also the creator of Monday Punday, the official name of his channel that is chock-full of comedy and, thank goodness, not much math. This nerd at heart taught me an invaluable life lesson. At various times, we all feel stupid, which very often results in us actually believing we're stupid. I, for one, always thought that I was bad at math. But as Matthew explained it to me, I'm not stupid.

• 1:20Simon Sinek?

  I was just taught badly. In this episode, we talk about curiosity, finding good teachers, and mothers. This is a bit of optimism.

• 1:36Simon Sinek?

  This episode is brought to you by Porsche and their new Macan. And when they reached out to us and asked if I would be comfortable to talk about the new Porsche Macan, well, let's just say, I already owned one. That's actually my car, so the simple answer was yes. So I discovered you on the Instagram. You, because comedians pop up in my feed. Apparently, the algorithm knows I like funny things. And so you were randomly thrust into my day. And I went down the Matthew Broussard rabbit hole. Like, you like one and then all of a sudden...

• 2:10Speaker 00

  I'm in your face, nonstop.

• 2:11Simon Sinek?

  An hour later, I'm like, shit, I should start work. You are... Exceptionally smart.

• 2:18Speaker 00

  Thank you, I appreciate that.

• 2:19Simon Sinek?

  I have to imagine that somebody has said to you at some point, "You're too smart to be a comedian. What are you doing with your life?"

• 2:29Speaker 00

  My parents have definitely said that.

• 2:33Speaker 00

  I was, I've, yeah. My, my, my parents didn't want me to pursue comedy. I was told from a very young age that I had above-average math skills specifically, and that was a very employable skill to have. And that, that skill was luckily fostered quite strongly, and I was able to learn. I was also very curious. I was, I was pretty self-motivated with it. I went to college for it. And it really wasn't until I tried an open mic that I even conceived of the notion that I could do anything else with my life besides use

• 3:06Simon Sinek?

  Math.

• 3:06Speaker 00

  Math to make money.

• 3:08Simon Sinek?

  Because you talk about math principles in your comedy sometimes. So we know that you know math. You also seem to like science, and you have an exceptional grasp of other things. Like, I guess it's part of memory. You just, I mean, you, you, I mean, we were having coffee, you know, before, when you arrived, and we're talking about the oxidization of coffee in a metal container. I mean, the fact that we're having this conversation is ridiculous, you know?

• 3:35Speaker 00

  Yeah.

• 3:35Simon Sinek?

  And it went beyond, "Tastes better not in metal." You know, like, the, the point is, is, is I'm so curious how you picked the path of greater risk. More joy, perhaps. That's a question, I guess.

• 3:49Speaker 00

  Yes. Thank you.

• 3:51Simon Sinek?

  Like, is this a conversation about, "Do the thing you have aptitude for versus follow your, follow your dreams and follow your passions?"

• 3:59Speaker 00

  I, so I was, I think, more pragmatic about it than most. I had, my first job out of college, I was working as a financial analyst, but not, not to the, not Wall Street. Like, easy hours, not the craziest pay, nine to five. I made spreadsheets for the most part. I didn't feel a sense of pride in what I did. It was, it was private wealth management. My job was to make rich people richer. And I didn't have a product I created, so some part of me felt a little empty doing that. Perhaps if I had been an engineer or a coder, and there was an actual product I was creating, I could have taken more pride in that. But I started doing open mics, and I saw...

• 4:37Simon Sinek?

  Just, just, just for fun?

• 4:39Speaker 00

  Just for fun. Uh, uh, well, I mean, I... I thought, wouldn't it be cool to do this full time? But I knew the odds were very low. And I said, let's try it. And the information was muddled at first, but there was an overall positive trend that I might have been towards the higher end of aptitude for a beginner. And I told myself, just keep noting where you stand against the ranks and how that extrapolates towards a career in this. But hold on for dear life to the career path you've worked very hard to have. Because I was still young, but stepping away from that could hurt and mean I could never potentially get back to the same

• 5:17Simon Sinek?

  Right.

• 5:17Speaker 00

  level that I was on track for.

• 5:19Simon Sinek?

  So you were parallel pathing it until

• 5:21Speaker 00

  As much as I could.

• 5:22Simon Sinek?

  Until one path revealed that this is a risk worth taking.

• 5:26Speaker 00

  Yes, well, what actually happened was comedy cost me my job in finance. So I was kind of burning the candle at both ends.

• 5:32Simon Sinek?

  Oh.

• 5:33Speaker 00

  Threw some mistakes on my part.

• 5:36Simon Sinek?

  Because comedy happens late at night if you're an open mic guy.

• 5:39Speaker 00

  Yes, and in California, and trying to do more and more. And it was because comedy was going fairly well that I was trying to move and trying to do more than I should have been doing. I ended up fairly losing my job. And that was the worst day of my life. I think it was October 4th, 2013. I was in California. I didn't have a place to live. I was staying with a friend. Everything I own was in my car and had to figure out like what I was going to do. And I said, well, this is, you know, my bank account is now my shot clock. So let's really go for it. And honestly, not that harrowing. Things kind of worked out within like two months. I started booking college gigs.

• 6:17Simon Sinek?

  Yeah, I'm always fascinated by people who, I mean, show business is a hard business. And I, and, and I'm curious if the internet has made it easier or harder for you. Because yes, exposure is easier. I mean, case in point, here we are because of the interwebs, because of social media. But at the same time, there is so much. There are so many open mic night, you know, little, some talent too, there's some talented people. But there's, so is it better or worse or just different challenges?

• 6:53Speaker 00

  There's a lot to unpack there. Comedy is, stand-up comedy is, the beauty of it is there's low barrier to entry. Yeah. The horror of it is there's low barrier to entry. Right. Meaning you are fighting through swarms of people. An actor at least goes through acting school and has some audition process. Hopefully musicians have to have the aptitude to play an instrument or sing. Anyone can do it, and now anyone can post it online. Comedy is like, anyone can stand on the stage and perform. Yes, and there's also no training for comedy besides getting on stage and performing. There's no school or class you can go to. You have to, to be good, you have to be on stage a lot, but to be on stage a lot, you have to be good. Right. So it's a very difficult track to get started in. The internet, though, the interesting thing with the internet was, I was very fortunate.

• 7:38Speaker 00

  In the early days of my stand-up, I was favored by the industry, Comedy Central, Conan. I got put on a lot of shows, which was nice. It didn't translate into having a fanbase. Those were the waning days of media, not for me at least. Some luck, some recognition, but I wasn't selling a ton of tickets off of that. Social media wasn't the way comedians were exposed back then. And then the pandemic hit, and then that was really the end of that. Those things don't make stars anymore. I've never been on Netflix. That might be a route, but even that's becoming less of a sure thing. Things changed for me on the business end when, during the pandemic, I realized Comedy Central was asleep at the wheel in terms of copyright issues.

• 8:23Speaker 00

  So I went back, I took my half hour, I took my Conan set, I took every set I did on television. You pulled that footage off YouTube and started cutting it up into Instagram reels and TikToks. And that's when people started knowing my comedy and sharing my comedy and recognizing me. So it was an interesting lesson in, rather than feeling defeated by this, looking at it as an opportunity to use that footage to, you know, I believed in this thing I'd already done. And then I thought, maybe if I can just get people to see this, I could start making an audience for myself. And that, that worked. To an extent.

• 8:55Simon Sinek?

  To an extent. Why is it, and obviously, that's where the wheat and the chaff separate. Because you get more likes, you get more forwards, the algorithm favors you, you'll do better. You'll get a following.

• 9:07Simon Sinek?

  I have a theory, which I'm, that I think comedians make great actors. You know, you look at people with backgrounds in comedy that became great actors, you know, Jim Carrey.

• 9:20Speaker 00

  Robin Williams.

• 9:21Simon Sinek?

  Robin Williams, Jamie Foxx, these are comedians.

• 9:25Speaker 00

  Michael Keaton.

• 9:26Simon Sinek?

  Michael Keaton, really?

• 9:28Speaker 00

  Was a stand-up.

• 9:28Simon Sinek?

  Was he really?

• 9:29Speaker 00

  Yes.

• 9:31Simon Sinek?

  Tom Hanks started doing comedy, not a stand-up, but that was his, so all of these, especially the ones who did stand-up. Michael Keaton didn't know, especially ones who do stand-up, I think they have the ability to become great actors because they get, this is my theory. Because vulnerability and humiliation are something they're attuned to, like, they have been, every comedian has bombed. Every comedian has been humiliated, every comedian has stood there knowing that it is going incredibly badly and you have to finish your set. And what a great actor has to tap into is the ability to be that vulnerable, that sort of perse, to persevere. And comedians just have a good training to be good actors. Comment.

• 10:15Speaker 00

  Can I disagree?

• 10:16Simon Sinek?

  Of course, it's a theory.

• 10:18Speaker 00

  It's a great theory.

• 10:19Simon Sinek?

  Theories are to be tested.

• 10:21Speaker 00

  I think you're right, and the beauty of comedy is the humiliation, is the vulnerability, I think. I really don't think great comedy can last very long without that, without that typically, yeah, vulnerability that makes other people feel less alone. Here's what I think separates stand-up comedy, potentially, and potentially why I'm not as good of an actor, because of being a stand-up comedian. If you were giving someone a massage and they were just completely silent. Would you know what you were doing? You might be good at it, you might not. What if they were telling you, that's the spot, go harder there? And even moaning, or going ow when you hit, hit, uh, bad spots? Which person do you think you would give a better massage to?

• 11:00Simon Sinek?

  Right.

• 11:00Speaker 00

  The, the vocal one. I like, if I can be a bit long-winded here. My love for, uh, math and my love for comedy, I, and, and, and science, I don't think they're separate entities. I, I am, I was not an artist by training. Uh, I think an artist creates things whose value is measured subjectively. Stand-up comedy specifically sits at an odd intersection in that you could almost not qualify it as art because every decision I make is focus grouped in real time.

• 11:30Simon Sinek?

  It's empirical.

• 11:30Speaker 00

  It's extremely empirical. I think that was my draw to it.

• 11:34Simon Sinek?

  And, and instant results.

• 11:35Speaker 00

  Instantly.

• 11:36Simon Sinek?

  Like math, the math, the, the solution is revealed in that moment.

• 11:39Speaker 00

  Yes.

• 11:39Simon Sinek?

  And comedy, the solution is revealed in that moment.

• 11:41Speaker 00

  Hypothesis, conclusion, in a heartbeat.

• 11:43Simon Sinek?

  In a heartbeat.

• 11:43Speaker 00

  In a heartbeat. And then you can iterate endlessly. I didn't, I, I'll change one word.

• 11:50Simon Sinek?

  The same night, yeah.

• 11:50Speaker 00

  Yep, I'll change one word and, and I'll, I'll try one, three different words in the same joke and go, okay. Based on a lot of data, noisy data, but data, I know this word is the funniest. And that's not the whole process, obviously you have to trust yourself more than that because there's too many variables. But, uh, that process is really wonderful to me. And I think it allows, uh, maybe the not most artistically inclined people to be somewhat better at stand-up because someone tells you when you're good and bad. The reason I struggle with acting, especially film acting, is because I don't know when I'm doing well or poorly. And when my brain hears silence, it panics and thinks it's doing something wrong. I think theater actors, um, the, the other side of that is, stand-up comedians and theater actors

• 12:32Speaker 00

  also have had lots of time knowing when they're doing well and knowing when they're doing poorly. And then, then it starts to become.

• 12:38Simon Sinek?

  Craft.

• 12:38Speaker 00

  Yes, and, uh, uh, unconscious competence, the highest level of the four.

• 12:43Simon Sinek?

  Right.

• 12:43Speaker 00

  Yes, so that's very neat to me. And, and, and just looking at it more of a science and empirical feedback loop.

• 12:50Simon Sinek?

  The, little end narcissism, not big end narcissism, but there's a, there's a little end narcissism to that, right? Which is, which is feed me, feed me, feed me, right?

• 12:59Speaker 00

  I think a lot, yeah. I think a constant need for validation, yeah.

• 13:03Simon Sinek?

  And, and is that, um, is that an insecurity? Or is that, uh, is, is it a bug or a feature?

• 13:11Speaker 00

  Oh, uh, both. Uh, yeah, I, I, I think if I could properly validate myself without external sources, I don't think I would need to do stand-up comedy. I think it's a need for validation. I think it's a, it's a, it's a whole. Uh, and I think it's probably common in other entertainers and potentially even business people.

• 13:30Simon Sinek?

  Yeah.

• 13:30Speaker 00

  Would you, would you agree that it's something on your side?

• 13:32Simon Sinek?

  Some of them, I think the ones that are more money-driven.

• 13:34Speaker 00

  Mm-hmm.

• 13:35Simon Sinek?

  The ones that I've met that are very, very money, money-driven.

• 13:38Speaker 00

  Mm-hmm.

• 13:38Simon Sinek?

  Uh, for them, the amount of money that they can achieve or the stock price they can drive, whatever it is, is a direct validation that they're good, smart, et cetera.

• 13:47Speaker 00

  Mm-hmm.

• 13:47Simon Sinek?

  Um, even though there may or may not be that correlation.

• 13:50Speaker 00

  It's the only yardstick they can find.

• 13:52Simon Sinek?

  It's, it's, and it's an, and it's an empirical yardstick. And it's a measurable yardstick. It's a, it's a yardstick that they can hold up to somebody else and be like, "See?"

• 14:00Speaker 00

  Mm-hmm.

• 14:00Simon Sinek?

  Right? And somebody goes, "I disagree." They're like, "But you're wrong, because here's what it says on, on the spreadsheet."

• 14:06Speaker 00

  Yes.

• 14:07Simon Sinek?

  So, so this plays to the trope that comedians are all a little broken.

• 14:15Speaker 00

  Yes. Yeah. I don't, I don't, I think that's a little over, overstating it.

• 14:20Simon Sinek?

  Overstating it, but, but, but the, but that need for, that need for external validation.

• 14:25Speaker 00

  But who doesn't have that? I guess it's just, is the need for validation higher than the fear of failure? And I guess for comedians, that's because I think a lot of people, I guess a lot of people are very afraid of stand-up. But to me, the, the, the result was so juicy that it was worth falling on my face.

• 14:41Simon Sinek?

  Right. That, right.

• 14:43Speaker 00

  Yeah.

• 14:43Simon Sinek?

  The, the, the, the benefits outweigh the risks, which is why you do it.

• 14:47Speaker 00

  Do you get a rush out of speaking publicly? Is that like, you must enjoy it?

• 14:51Simon Sinek?

  I, I think any, but I think there's no avoiding the adrenaline. Standing in front of huge audiences sometimes, there's no avoiding the enjoyment of the adrenaline.

• 15:00Speaker 00

  Mm-hmm.

• 15:01Simon Sinek?

  And I think the, what separates the good ones from the mediocre ones is for some, that adrenaline translates into fear and anxiety. And for, and for the good ones, we've learned to translate the adrenaline into presence and energy and focus. And, and it's all about you. So the adrenaline is my friend.

• 15:20Speaker 00

  Yes.

• 15:21Simon Sinek?

  Uh, it makes me better at what I do.

• 15:22Speaker 00

  Mm-hmm.

• 15:23Simon Sinek?

  Um, but- I mean, of course, of course, it feels good. Nobody can deny that. And of course, I like it when I get it. The question is, do I need it? And I don't.

• 15:36Speaker 00

  What is the part of what you do that is the most satisfying?

• 15:42Simon Sinek?

  So I am driven. The hard thing for my work is, and when you make the difference between sort of the scientist and the artist, you know, the empirical versus the subjective, which is, though I have empirical metrics, you know, I have views of videos and I have forwards and I have, you know, book sales. And those things are indicators to me. But the thing that drives me is impact. What means the most to me is that I'm undoing everything Jack Welch ever did. Like, I want to reverse everything that man broke in capitalism.

• 16:16Speaker 00

  The why?

• 16:17Simon Sinek?

  Yeah.

• 16:18Speaker 00

  Yeah.

• 16:18Simon Sinek?

  But like, I have a, I have a, I'm chipping away, you know? And, and like, the people that drive me and inspire me, so like, the, all the founding members of the American Women Suffrage Movement all died before the first woman voted.

• 16:38Simon Sinek?

  None of them, none of them, none of them lived to see a woman vote. What I'm, what, the reason that inspires me is they still never gave up. It was never in their grasp, yet they continued because their metric was momentum, not result. They obviously wanted the result. They would have preferred it happened in their lifetime. Of course, we know all these things. But the ability to, to, to measure momentum and have the peace of mind to know that upon my death, others will take this torch and continue without me, and that means my work was worth it. That, to me, is super inspiring.

• 17:13Speaker 00

  That's very noble. That's really wonderful. I think my ego is too strong that I, I need to see it and get credit for it, anything I'm a part of. So I'm not a good person. But that's lovely. Like, it's like generational starships. That's, I read a lot about, like, in sci-fi, it's like, it's a common thing in sci-fi. A spaceship will take off towards whatever other star and the original inhabitants know they will die before it gets there. But their children, their children's children might see the, the new world.

• 17:43Simon Sinek?

  Don't get me wrong. I, there's no nobility here. I like instant gratification. I like results, like, you know, I, I, I like all those things. You know, it's not, it's not an either or, it's a both.

• 17:54Simon Sinek?

  And The mindset, the infinite mindset that's required to have that has some very different standards, which is I have no choice but to rely on people, need people, trust people. I have no choice. I can't be a lone wolf. It just, then it would never work. Right. And so, and again, not better or worse. And I think the opportunity for all of us is to understand where we're selfishly driven. Totally fine. And where we're, where we're not.

• 18:31Simon Sinek?

  We interrupt this episode to have an ad with authenticity. This episode is brought to you by Porsche and their new Macan, which is my actual car. I had it before they called. I didn't want to make some ridiculous, over the top car commercial.

• 18:50Simon Sinek?

  So instead, we went out to a closed track to have a little fun. And just to keep me humble, they brought along race car driver Patrick Long. And if I'm really honest, it did get a little over the top.

• 19:05Simon Sinek?

  So I'm not gonna lie, right? So I have a Porsche Macan 4, an electric Porsche. And it has three modes. It has comfort, sport, and off-road. I thought the off-road setting was a joke. It's a frickin' Porsche. It's a race car pedigree. Like, they put it there, I don't know, in case there's some wet leaves on the road and, you know. But we're now about to do an off-road test here, where I'm gonna drive up an extremely steep dirt road. And so I think- Yeah, look at that. We're gonna come down that. That's ridiculous. So I'm about to eat my hat. So basically, the radar is flashing because it thinks I'm gonna hit another car. That's how steep this, this road is that I'm going up.

• 19:50Simon Sinek?

  Where's my handles? The fact that I'm going up a hill and I can't see anything but sky, and I'm convinced that, like, I'm gonna go over the top here and die. But here it goes. This is, this is amazing! We're about six, eight stories up in the air right now. This is ridiculous. I'm just like looking straight down at the ground. This is so ridiculous.

• 20:15Speaker 00

  It's wild.

• 20:16Simon Sinek?

  Ridiculous.

• 20:17Speaker 00

  It's so wild.

• 20:18Simon Sinek?

  That was incredible. I'm not gonna lie. I thought the whole thing was a farce and it's not.

• 20:24Speaker 00

  Like you said, the grip, I feel like there's these claws or like a spider, how it sort of just grabs whatever it can as it's coming up or down.

• 20:32Simon Sinek?

  That's super cool.

• 20:33Speaker 00

  You did a great job there.

• 20:34Simon Sinek?

  Oh, thank you very much.

• 20:43Simon Sinek?

  Do you still do math?

• 20:44Speaker 00

  Yes.

• 20:45Simon Sinek?

  Like for fun?

• 20:46Speaker 00

  I tutor.

• 20:47Simon Sinek?

  Oh.

• 20:48Speaker 00

  Which is great.

• 20:48Simon Sinek?

  At what level?

• 20:50Speaker 00

  I'm lucky. There's this volunteer organization I work through, college. So I greedily go for kind of the classes at very much the end of my range. Because those are more fun than going back to the earlier stuff. But college, a lot of like engineers, calculus, calc 2, calc 3, linear algebra. Those are the fun stuff. I'm trying to do something. I think it's like maybe like a partial differential equations this semester. And I'm like really having to catch up between sessions on stuff I didn't learn that well the first time, so.

• 21:21Simon Sinek?

  It is amazing how opposite we are.

• 21:23Speaker 00

  You don't like math?

• 21:25Simon Sinek?

  I don't dislike it. I don't have an instinct for it. Like I can, I can, I never, I'm very proud of this, actually. I've managed to go through all of high school and college and never took calculus. So I don't know anything about calculus. I don't know what it is. I understand algebra, I understand geometry.

• 21:46Simon Sinek?

  And trigonometry, you start to lose me.

• 21:48Speaker 00

  Trigonometry sucks. There's some bad stops along the way. It's like a series. There's gonna be episodes that are duds, but you look at it in its entirety.

• 21:56Simon Sinek?

  Calculus I know nothing about.

• 21:57Speaker 00

  Calculus is a function. The function is you put in x, you get a y, right? And you can get a curve with that, right? Yeah? Calculus is just, well, how steep is that curve? That's it.

• 22:08Simon Sinek?

  And what's the practical application of calculus?

• 22:10Speaker 00

  Uh, the steepness of a curve would represent the, uh, oftentimes the speed. If, if position, building a position, the steepness is the, uh.

• 22:18Simon Sinek?

  So the application is physics and things like that?

• 22:20Speaker 00

  Physics, a lot, I mean, yeah, physics, chemistry, a lot of stuff, finance, and then speed, and then acceleration. If you take another, if you go another level deeper, it's acceleration. But if you reverse that process, if you have, uh, the graph of speed, then you take the area underneath it, and that gives you the distance. That's basically calculus in a nutshell.

• 22:38Simon Sinek?

  I have to say, that's interesting.

• 22:41Speaker 00

  Now, I could really, this is, this is what I'm really passionate about. If I, if I, if I could restart and didn't have to do comedy and wanted to do another dream, it's that math education is, it, it, we're doing it very wrong. What good mathematicians, I believe, possess is the ability to hold big pictures in their mind and manipulate them, um, which is a, a, a good gift, and it gives people, uh, some abilities. But, but what I think is, is needed is just making those pictures. Those pictures don't exist, those videos don't exist. There's concepts I learned in college that I, I, I thought I knew, and I went through the process, and I struggled to learn them, and I applied them.

• 23:21Speaker 00

  And then now, twenty years later, I'll see a ten-second video on YouTube, and I go, that's what that was? That's what was happening? You never showed me that. You never showed me in three dimensions with colors and moving images what was happening. And now that I see that, everything I did is unlocked. If you just had those visuals, not everyone's gonna understand math, but if you had the proper, we're teaching math with a static image drawn on a chalkboard. It should be done by the people at Pixar. It should be dimensions of time, three dimensions of space. And yet we're limiting to zero dimensions of time, two dimensions of space.

• 23:56Simon Sinek?

  Here's what I'm taking away from this, this is, and light bulbs are going off, right? And now I realize we're actually more alike. Which is, what you and I both do is we take complex ideas and we make them that people understand it, either so that you have clarity or you can find the humor in the thing. Mm hmm. Right, because it's the kind of the same thing. Mm hmm. Right, which is, you're, you're, you're pointing out the absurdities of life, the absurdities of your mom, you know, and, and you, it's presented in a way, like what makes a great comedian from an okay comedian is that you're presenting in a way that there's, that I can relate to the story, which is why I find it funny. Mm hmm. It's not just the story, right? It's not just the funny thing that happened. The telling of it matters.

• 24:38Simon Sinek?

  And, and math and, and, and adjacent subjects have always been, for those who have the math mind, quote unquote. It never occurred to me that it was just being taught badly. It's being taught horribly. That if you taught me math the way you tell jokes, or the way I explain an idea, because, because I, people, people think that I'm joking when I say this, but I think of myself as an idiot. And I, I mean that 100%, I mean, there is not a, an ironic, nothing, there's nothing ironic about that, which is, as a kid with ADHD in, in high school, I struggled to read,

• 25:19Simon Sinek?

  I struggled to study, I couldn't learn by rote, like, and so I still got to pass high school. So you have two options, fail or figure it out. So what I learned to do was be really good at asking questions, get really good at, at listening. I had to attend class, I couldn't cut school, because if I cut, and when I was in college, I had to choose professors who were good at explaining, because I could never rely on the book to catch up. Yeah. Right? And that skill of learning to survive and, and, and turn my ADHD into an advantage rather than, than a, than a deficit, gave me this capacity in the future, which is when I hear complex things that people are trying to explain to me, I have no fear, I can't have

• 26:03Simon Sinek?

  any fear, it's a survival thing, it's not a courage thing. I have, I have no fear to say, I don't understand, can you explain it differently? And then they'll try again, I'll say, is this what you're trying to say? And I'll say it in simple terms that I can understand.

• 26:16Speaker 00

  Yeah.

• 26:16Simon Sinek?

  And I go backwards and forwards and backwards and forwards and backwards and forwards, until I be like, and I'm drawing little pictures and using metaphors and analogies, simply because my little brain is trying to understand this complex thing that you're trying to explain to me. And eventually I understand it, because I've boiled it down to something very, very simple.

• 26:30Speaker 00

  Yeah.

• 26:31Simon Sinek?

  So simple, that not only do I understand it, but I can then tell somebody else. And then they go, got it. And I get all the credit, which is not fair, for being the expl- but I was just trying to understand the complex thing in the first place. And where it fails is when the person's trying to explain it to me and they can't, then I can't understand it, because I don't have that analytical kind of mind that just understands, you know, sort of math and equations.

• 26:54Speaker 00

  No, but people don't understand it quickly. This is, this is, I think, the great myth of, of people who-

• 26:59Simon Sinek?

  No, no, no, people do. People can do math in their heads very easily.

• 27:02Speaker 00

  No, no. I, I, like, this was said by someone else, I think it was said by, uh, uh, Matt Parker of Stand Up Maths. But he said that, that, that we all, anyone who studies math is, is, is constantly bombarded by frustration, but you embrace the frustration. You know that you're going to feel pain.

• 27:20Simon Sinek?

  Yeah.

• 27:20Speaker 00

  And you're going to feel anger. And then in one moment, all of those negative feelings are going to snap to positive feelings. And that's the moment of understanding. And, and what people who pursue any kind of field of study know is that you have to look it in the face and not back down. That's the moment where-

• 27:36Simon Sinek?

  But where can you adjust? So like, when I see, when I look at financial information, like for the company, right? I always ask the finance person, show me a chart and a graph. Like, show me, uh, show me, I, I want to see the visual. I want to see the trend. I want to see the profit and loss done in pretty pictures, because then I can understand it. When you just show me huge spreadsheets of number, I just gloss over.

• 27:58Speaker 00

  Sure.

• 27:58Simon Sinek?

  I struggle. But some people, like, they look at those huge spreadsheets and they're like, ah, you're one of those people.

• 28:04Speaker 00

  No, I mean, well, the, the analog for me would be, uh, I'm constantly trying to learn new things in math. And the first read will always feel, make, I'll feel like an idiot. But I know, like, you should feel stupid.

• 28:15Simon Sinek?

  Yeah.

• 28:16Speaker 00

  Feeling stupid is part of it. And admit that you're stupid, admit you don't know. And I will, I will look at one thing, read it, go, I don't like that. And I'll look up several different, different ways of explaining it. Until the seventh one, I'm like, this time I get it. And I'll also have to read it over and over again. I, I, I, I don't think- That it's necessarily some people just inherently get it. They're just willing to admit they're stupid. And like you're saying, I love it. Keep simplifying it until there's one aspect of it you get. And then what's the next thing you can add to that?

• 28:41Simon Sinek?

  What you just said was absolute genius. No, no, no, no.

• 28:46Speaker 00

  Give me too much.

• 28:46Simon Sinek?

  No, no, no, no. What you just said was absolute genius, which is a perfect, like, which is what we do when we feel stupid is we watch or read the same thing over and over and over again to try to understand it, each time blaming ourselves for being stupid. What you're saying is, and this is the genius, show me seven different ways to explain it until I understand it.

• 29:08Speaker 00

  Mm hmm.

• 29:09Simon Sinek?

  Right? Which is whether it's a leadership concept, or a financial concept, or a scientific concept, or any kind of concept that you're struggling with.

• 29:15Speaker 00

  Mm hmm.

• 29:16Simon Sinek?

  It's okay to feel stupid. It's okay to maybe reread it once or twice, but then go seek out. And this is where the internet is the greatest gift.

• 29:24Speaker 00

  It's wonderful.

• 29:25Simon Sinek?

  Which is you can go down a YouTube rabbit hole.

• 29:27Speaker 00

  Yes.

• 29:27Simon Sinek?

  And have, and you can start, you can hit play and be like, eh, and you can play until somebody, somebody it makes sense to you. And then you'll understand this difficult concept. And by feeling a little less stupid in that moment from that explanation, A, you're learning how you learn, but B, now you have the grit because you're not blaming.

• 29:47Speaker 00

  The patience and the humility.

• 29:49Simon Sinek?

  Because here's what we're doing, right? I feel stupid. It becomes a, it becomes a story to ourselves. I am stupid. And then you just, I don't do math. I don't understand math. I'm no good at math. What the story should be is I have yet to find somebody who can explain math in a way to me that I can understand it.

• 30:06Speaker 00

  Yes.

• 30:06Simon Sinek?

  That is the correct mindset.

• 30:08Speaker 00

  Plus some patience, plus rereading it.

• 30:10Simon Sinek?

  I, I, like, people thought that we were gonna be funny. The, the, the.

• 30:17Simon Sinek?

  We have Matthew Broussard and we're gonna talk about learning. Uh, but no, but this is.

• 30:23Simon Sinek?

  I never want anybody to feel dumb again. This is gonna be my mantra. I'm gonna say-

• 30:27Speaker 00

  Or we're all dumb. We all feel dumb all the time.

• 30:29Simon Sinek?

  We all, but the mantra is, don't blame yourself, blame the way you're being taught.

• 30:35Speaker 00

  Yes. And have patience with those teachings. And you're talking about communication. There's two, learning takes someone who's patient enough to learn and someone who's patient enough to teach. And again, I'm very familiar with concepts. Can you tell me a different way? Can you tell me a different way? Can you tell me a different way? Because what might unlock it for me might not for another person. I've been doing something lately that's been something I didn't do in college. Which, I'm sorry, the internet comment. I think about that so often of when I was in college and I was trying to understand a concept and one of my harder classes, singular value decomposition, let's say that one, because it sounds smart. The only thing I could do was go to Wikipedia and read the page for it. You know who wrote that page? My professor.

• 31:18Speaker 00

  My professors in college wrote all the Wikipedia pages for the concepts we were learning because it wasn't widely shared knowledge at that point. Now, if I wanted to understand that, there's seven YouTube videos I could watch.

• 31:30Simon Sinek?

  Yeah.

• 31:30Speaker 00

  And perhaps the fifth one is when I really get it, because they did a good job with the visuals.

• 31:34Simon Sinek?

  Yeah.

• 31:34Speaker 00

  I've also been reading math textbooks, just to learn things I've always wanted to learn. At a snail's pace, but something I didn't realize was I thought I was just not good at reading math textbooks because I'll read one page, think I get it, and the second page, my brain goes to mush. Like the endurance over two pages, it's like, it's like when you're bad at swimming and you try to swim, you get across the pool, you're like, that was easy. And then you can't make it to the next wall. And then I talked to someone who was a math PhD, they go, that's how it is. One page a day is a great rate. It's just that hard.

• 32:02Simon Sinek?

  Wow.

• 32:03Speaker 00

  And the people who accomplish it forget how hard it was or want you to think they're smart. And it's that hard for everyone. I feel that way about comedy. Every, every line I have that makes the crowd laugh feels like a miracle. And it's like, I think how rarely I write two jokes in the same day.

• 32:19Simon Sinek?

  Yeah.

• 32:20Speaker 00

  Like, every, every punchline you hear is one day of my life and that was the accomplishment for that day. Even if it's just like three words that get like a chuckle. It's such a, it's- What's, what's, who's famous line, if you saw the work put into it, it would not be impressive at all?

• 32:36Simon Sinek?

  Yeah, yeah.

• 32:37Speaker 00

  I, I think for me, maybe for other standups, maybe not, it's just not an easy process. It's laborious, but that's what it takes to make something that's engaging. And I, I imagine you feel the same way about your work. It's just, it's not easy.

• 32:52Simon Sinek?

  It's, it's, my process is a little different. I'm curious, I'm curious, are you good at crowd work?

• 32:58Speaker 00

  Like? No.

• 32:59Simon Sinek?

  Okay.

• 33:00Speaker 00

  No, I need to learn how to listen better. I think that's the problem.

• 33:02Simon Sinek?

  Okay. Cause the people who are good at crowd work, when they're good at it, it's a thing to behold.

• 33:06Speaker 00

  It's cool.

• 33:07Simon Sinek?

  It's a thing to behold.

• 33:08Speaker 00

  They're patient, they have, it's, that's, that's like a, a real zen state. You have to be calm, you have to make the crowd feel like they're okay. You have to take what they're saying, know when to ask another question, or know when you have enough stuff to put together.

• 33:20Simon Sinek?

  Yeah.

• 33:21Speaker 00

  And when to have emotional responses, when to try to be clever, when to just try to repeat back what's happening. I would love to be better at it.

• 33:28Simon Sinek?

  One, one thing that I love about your work is, first of all, super vulnerable. Like you share things, I don't know if they're jokes or if they're true. Cause I know there's some truth, but I also know that, you know, when you get on a good idea, you can play with it. But I just watched a bit about your inability to please your wife.

• 33:47Speaker 00

  That is 100% true. Yeah, that, that, that is.

• 33:50Simon Sinek?

  I mean, like, does she want that out there?

• 33:54Simon Sinek?

  I understand that you don't mind. I understand that you don't mind having it out there. There's two players in this game.

• 34:00Speaker 00

  She was a very good sport about that. For a while I was like, can we talk about this? She was like, oh, that's a lot. And then I think at one point she was just like, you know what? It's a good thing to share with people who feel the same way, both men and women who struggle with that.

• 34:14Simon Sinek?

  Yeah.

• 34:14Speaker 00

  And it might make people feel more comfortable about themselves and more comfortable in the relationship. So it's a good thing to share with people.

• 34:20Simon Sinek?

  Yeah.

• 34:20Speaker 00

  I'd love vulnerable. I love, to me, it's my favorite part about comedy is when you can share something that you're embarrassed by. And now instead of being embarrassed by it, you feel a sense of community with other people who feel that. Or you, you. Even if that doesn't work, then you've made people who don't have that vulnerability feel better about themselves for not having it.

• 34:38Simon Sinek?

  Right, right.

• 34:38Speaker 00

  So everyone wins.

• 34:40Simon Sinek?

  But it is, it is the quintessential court jester, right? Which is, I'm gonna say the thing that everybody's thinking, but I'm gonna make it okay. I'm gonna make it okay.

• 34:48Speaker 00

  Make people feel less alone.

• 34:49Simon Sinek?

  I have to believe that a lot of your bits started conversations that were for the, were for good. And it's only because your work, I'm astonished how often you are so vulnerable. Whether it's about yourself, your upbringing, even talking about, you know, racism and some of, and hot topics. You'll go there. And, and I just find it very impressive. I've so enjoyed, and I kind of remember how long ago it was when I first discovered your work. But I've, I, I, your work is getting, for what it, for what it's worth, it's getting better and better and better.

• 35:21Speaker 00

  Thank you. I really appreciate that.

• 35:22Simon Sinek?

  Yeah.

• 35:23Speaker 00

  Thank you. That's very kind.

• 35:25Simon Sinek?

  Was that always, were you always that kid that didn't mind being embarrassed, that didn't mind being vulnerable? Like, so how did you learn it?

• 35:30Speaker 00

  Kind of through stand-up. Early on in stand-up, I was just trying, I, I, when I started, I wanted to be brash and offensive because I thought that was cool.

• 35:38Simon Sinek?

  Andrew Dice Clay style?

• 35:39Speaker 00

  Yeah, and, and I, I kind of realized later that was more, that was not me being tough and edgy. That was me actually being weak and insecure, needing to put others down to, to feel some sense of superiority.

• 35:52Simon Sinek?

  Did it get laughs?

• 35:54Speaker 00

  Sometimes.

• 35:55Simon Sinek?

  Yeah.

• 35:55Speaker 00

  Sometimes in front of other people who liked, who liked that. I, of all people, James Comey's memoir was, was, it really shaped me. There was one chapter, I, I can't imagine a less funny person than former FBI director James Comey. But he had, I, I think it was, it goes to speak of how not funny people can sometimes have the best observations about comedy. He had a whole chapter talking about the sense of humor of the three presidents he worked under.

• 36:27Simon Sinek?

  Right.

• 36:28Speaker 00

  Which is Bush, Bush Junior, Obama, and Trump. And he said, "All three were notably funny guys, very funny people. Bush Junior and Trump would often make laughter at the expense of others, which did not equate to good leadership."

• 36:46Speaker 00

  Versus Obama would make jokes at the expense of himself, which would uplift others and bring out the best in them. So, sure.

• 36:54Simon Sinek?

  Maybe, but, but, but anyway, moving on, moving on.

• 36:58Speaker 00

  Ignoring the politics of that.

• 36:59Simon Sinek?

  Ignoring the politics of, of the comment. I, I get it.

• 37:02Speaker 00

  The idea that, and that was, that was also for me, a, a great thing of, a, a learning experience in that, um, if there's going to be a victim to the joke, why not me? I'm, I'm, I'm the consenting party.

• 37:13Simon Sinek?

  Right. It's a victimless crime. Yeah.

• 37:16Speaker 00

  And, and, and not just victimless, it, it, it helps other people. I think I, I somewhat possess a bit of status that a comedian wouldn't typically possess. You take a, a picture of a comedian, you often think of like a dirtbag, someone down and out.

• 37:30Simon Sinek?

  Yeah.

• 37:30Speaker 00

  Um, uh, I've had, I think to see me take a tumble is, is, is, is maybe a little more satisfying.

• 37:38Simon Sinek?

  Right.

• 37:38Speaker 00

  Cause I started falling from a little higher.

• 37:41Simon Sinek?

  Yeah.

• 37:41Speaker 00

  Yeah.

• 37:42Simon Sinek?

  So do you remember the first joke, the, the first risk you took at self-deprecation? This new style? Do you remember it?

• 37:48Speaker 00

  Uh, yeah, I was, it was, uh, uh, I was doing jokes about looking like an eighties villain and it was getting a laugh. And then people came up to me after the show and you get a lot of great feedback from just drunk people.

• 37:57Simon Sinek?

  Yeah.

• 37:57Speaker 00

  Not just empirical feedback during the show, but drunk people will come up and just really say blunt things. And some guy was just like, yeah, you look like a douchebag and I didn't like you. And then you started talking about looking like eighties villain. I'm like, oh, this guy's not bad. And I'm like, what if we just, what if we, instead of trying to do that with tricks, just say exactly what he's saying? And I, I think I was at Sacred Heart College and I was doing a show and I just said, I look like a douchebag. I'm guessing you already didn't like me before I started talking. And that was like, oh, I'm cutting straight to the chase there.

• 38:26Simon Sinek?

  Right.

• 38:26Speaker 00

  I'm acknowledging what they think of me before they've even put it together themselves.

• 38:29Simon Sinek?

  Right.

• 38:30Speaker 00

  And now, now they're more malleable because I've kind of maybe subverted their expectations and, and shown awareness that they're like, you take the reins, actually. If you, if you're on top of things, you, maybe you know what you're doing. We'll let you, you've taken yourself down a peg in a way that we find satisfying. Um, yeah, keep going.

• 38:51Simon Sinek?

  And now, it's, and, and does your mom know the way you talk about her?

• 38:56Speaker 00

  Yes, she's fortunately very, she doesn't mind it.

• 39:02Simon Sinek?

  She sounds like an absolute caricature.

• 39:05Speaker 00

  I've, I've barely painted the picture with my stand-up of how, how well she is. I've included the parts that are digestible. She likes, she doesn't mind anything. The crazy part was the, I don't know if you saw the airport story.

• 39:17Simon Sinek?

  Oh, I saw the airport story.

• 39:21Speaker 00

  That's, I, I can't stress how true that story is.

• 39:23Simon Sinek?

  Do, do you want to tell the airport story for those who haven't seen it on the YouTube?

• 39:26Speaker 00

  I'll, I'll give the introduction. I was, I was dropping her off at the airport and had to shortly thereafter come back and pick her up. She went to check in. They were giving her trouble over paperwork for bringing a dog in the plane. She forgot, I swear to God, she forgot the word manager and said, let me speak to your master. And that was, that was where the story starts.

• 39:46Simon Sinek?

  Yeah.

• 39:47Speaker 00

  She signed off on, I said, are you, can I talk about that on stage? She was, yeah, it's funny.

• 39:53Simon Sinek?

  It is funny.

• 39:54Speaker 00

  Yeah, I'm like, you're, you sure about that? She was like, yeah. The one thing she doesn't like is the birthday card, which I recommend, I can't do it here, but a birthday card she sent to my, my wife. I, I said, Mom, this, this note's really funny. I'm gonna read it on stage. She goes, sure, no one's gonna laugh. And then she saw me do it live and people laugh at almost every sentence as I read it verbatim. And she goes, why are they laughing? I don't like this. What are they laughing at? And I had to explain to her, I'm like, they're not laughing at you, they're laughing at the vulnerability, at you saying things we all think, but keep to ourselves.

• 40:26Simon Sinek?

  Yeah. What's next? What, what's the ambition?

• 40:31Simon Sinek?

  Do you have vision or do you just keep doing the thing you love and it keeps going in the right direction?

• 40:35Speaker 00

  I'm not good about all the things you profess, which I don't have the, the infinite game. I just have the next special and wanting to just kind of branch out a little bit at a time. Perhaps I'd be farther along if I had a, a bigger vision, but.

• 40:48Simon Sinek?

  What do you mean farther along? Like?

• 40:51Speaker 00

  Like, uh.

• 40:52Simon Sinek?

  Like, what does that even mean?

• 40:52Speaker 00

  Be on TV, be on a TV show and bigger crowd.

• 40:56Simon Sinek?

  But is that, I mean, it's like, but you don't want to act?

• 40:59Speaker 00

  I would love to. I love acting. I just find it challenging and not as natural for me. I love acting.

• 41:03Simon Sinek?

  Okay.

• 41:04Speaker 00

  I would, my, I mean, my dream was to do stand up and put out specials.

• 41:07Simon Sinek?

  Okay.

• 41:08Speaker 00

  And I've really accomplished most of that. Like, there's room, but if I, if I, if me, when I started, saw where I am now, they'd be like, you're doing it. Uh, I would love to be on a sitcom. That's always been my dream.

• 41:17Simon Sinek?

  Okay.

• 41:18Speaker 00

  Cause those, those, those perhaps shaped my life more than stand up did, and I shouldn't admit that, but like, 30 Rock, Parks and Rec, Community, uh, and then cartoons, Futurama, Adventure Time, those, those things hold such real estate in my heart. So to be involved with any of those would be the other, like the other box to check.

• 41:40Speaker 00

  And obviously I want to keep making specials. That would be really cool to, to keep putting out long form stand up content.

• 41:45Simon Sinek?

  Is, is, is, is stand up comedy, um, could you ever walk away from it?

• 41:49Speaker 00

  I don't think so. I really like it. I really like the feedback from people and getting to go up there and say things and feeling less alone. I think our phones make us feel very, very isolated. It's this synthetic connection.

• 42:00Simon Sinek?

  Yeah.

• 42:00Speaker 00

  These empty calories.

• 42:01Simon Sinek?

  Yeah.

• 42:01Speaker 00

  Of, of human interaction that make us feel more depleted afterwards. Uh, the human to human part of it, uh, I, I'd feel starved without it.

• 42:13Simon Sinek?

  It's, it's, it's, it's kind of a last frontier, right? I mean, where you can interact with each other and, and when I say each other, I mean, it's, it's up and down, you know, it's, it's comedian to audience, but it's also audience to audience. We, we laugh next to each other. We look at each other. We elbow each other. We point. You know, it's a, it's a, it's different than theater. Theater is a very lonely experience because you sit by yourself. Nobody can see you because you, you can't see anybody. You can only see the back of people's heads.

• 42:39Speaker 00

  The script is set.

• 42:40Simon Sinek?

  The script is set. And, and so it's, it's very different than theater. And to your point, which is where we come for entertainment and we do put our phones away. And, and we have a couple of drinks and we're forced to have a couple of drinks and forced to order some food. Cause that's the business model.

• 42:58Simon Sinek?

  And, and it is, I, I don't think comedy is going away and I don't think live comedy is going away.

• 43:03Speaker 00

  Yeah. I don't think live anything is going away. I don't think anything's, we, we just don't have the substitute for, we think that, cause we can look at something and hear something that it's, that it's the same of just even being here in person versus a Zoom. It's just more dimensions.

• 43:18Simon Sinek?

  It is more dimensions.

• 43:20Speaker 00

  What's next for you? How do you look at growth?

• 43:25Simon Sinek?

  So I

• 43:26Speaker 00

  And how do you balance growth with already feeling like you've done enough?

• 43:30Simon Sinek?

  Okay, there's multiple questions there.

• 43:33Simon Sinek?

  I think of my work like an iceberg, right? So when I was starting and I was just an idiot with an idea, like literally accomplished nothing, no books, no TED Talks, no nothing, nobody knew who I was, nobody knew my ideas. All I had was a theory of what the world could be like and what business could be like, which is basically an iceberg completely submerged. I'm the only one that can see it. And like, the ability to explain it to a couple of people, so they go, oh yeah. It's kind of like a tiny bit of iceberg sticking up. And so when people pay me compliments, what they're looking is what they can see above the ocean. When I think about what work I have to do, I still can only see what's beneath the ocean.

• 44:15Simon Sinek?

  And so no matter what I've done or accomplished, people will say nice things to me, look at all the things you've done. And I'm sort of always a little bit sort of like taken aback because I don't think about it. Because what I think is like, oh, I still have so much to do, you know? And it's kind of like the way you talked about feeling stupid with the math, which is I like learning curves. I like difficult problems, I like problems I struggle to wrap my head around. I like finding different angles to it. And to me, what the iceberg represents is I still haven't cracked, I haven't cracked it yet. I've just sort of made some steps towards it. But for me, it's all about what still lies beneath. And like I said, undoing everything Jack Welch did, that's a real fricking, that's a job, right?

• 45:00Simon Sinek?

  So that's how I think about career and sort of accomplishment. But I also have a very, very different way of going about sort of my whole life. Every performance review I ever had and every job I ever had, every single one of them said, you're unfocused.

• 45:20Simon Sinek?

  And and I believed it because everybody kept telling me, even growing up, studying, you're so unfocused. And my work is semi autobiographical. It's me trying to solve my own problems. And so the discovery of things like the why and the discovery of things like the infinite game helped me understand that I am actually one of the most focused people I know. I'm just focused on a different horizon than most people. And so the way I would describe it is, um, most people are obsessed with the route. I'm obsessed with the destination. Right? Um, for example, you're, um, you, you, you, you walk outside your front door and you see your neighbor packing their car. And you said to your neighbor, where are you going? They go, vacation. And you go, cool.

• 46:05Simon Sinek?

  Where are you going? They said, vacation. I'm like, no, no, no, no. Where are you going? I told you, vacation. And you're like, fine. How are you gonna get to this vacation? And they're gonna, they say, well, I'm gonna take 95, I'm gonna drive 150 miles a day until I get there. And what they're telling you is the route. And that's what most people have. I'm gonna get this kind of job, I'm gonna make this amount of money, um, this is my career path. They have fixed roots, but not 100% clarity of where they're going. Right? And so the route is everything. I have been very different, which is, uh, let's say we're in California now. Where are you going? New York. How are you gonna get there? Don't know. And so it's very opportunistic.

• 46:47Simon Sinek?

  And so when, when a lot of people, for example, they're offered a job that pays more money, they're like, I'll take that one. It pays more money. And I go, well, will that one help me get to New York? No. Well, then I'm gonna turn that one down. And so I realized where so many people are focused on the route, I'm completely agnostic. And the, and if you're focused on the route, that means you're agnostic on the destination. And I know too many people who spend a whole life climbing a ladder, only to get to the end, to discover they climbed the wrong ladder.

• 47:22Speaker 00

  This ties back to calculus.

• 47:24Simon Sinek?

  Say more.

• 47:25Speaker 00

  Okay. Uh, calc, multi-variable calculus and then the classical optimization. I think about this a lot. Uh, um, you're trying to find the highest point. That's what optimization is.

• 47:34Simon Sinek?

  Yeah.

• 47:34Speaker 00

  You can, you can, uh, you can walk north or west, right? You're just trying to pick based on two directions. Where's the highest point? Now, let's say you're walking on a hilly field at night and it's foggy. So you can't see when you're in the top. You're gonna know when you're at the top because your feet are gonna be flat on the ground. Maybe you're at the bottom, but you're gonna, right? So what is the search algorithm? Your search algorithm is you're gonna walk around. And when it feels steep, you can feel your ankles bend a lot. You walk in the direction of the steepness. The more steep it is, the longer of a step you take, right? If it starts to flatten out, then you're near the top. Um, that is what we do mathematically. The steepness, again, that's the slope in calculus. That is, that is actually the math of it. Um, the problem is, what if there's another hill next to you that's higher?

• 48:16Speaker 00

  You need to wander off the hill to potentially find the highest point. You need to be able to go off that path and potentially explore other ones. So are you finding a local optimum or a global optimum? Uh, I think a lot about that when we're, and, and, and what we're, what we're optimizing for, what we're trying to maximize. Sometimes we look at, we were talking earlier about the, uh, empirical feedback. If we say, oh, these, these results mean I'm doing well. I'm getting a lot of views on my Instagram reels. That's an indicator that I'm, that I'm doing well.

• 48:44Simon Sinek?

  Right.

• 48:44Speaker 00

  What if you get it wrong? A lot of people do. What if, what if I'm doing well because I'm, what if you flip it? Those views are the measure.

• 48:53Simon Sinek?

  Right.

• 48:53Speaker 00

  And now you do everything you can to optimize that. You're going to do a lot of things that are.

• 48:57Simon Sinek?

  Clickbaity things.

• 48:58Speaker 00

  Bad things, just not, not in the intention of what you wanted to create originally.

• 49:01Simon Sinek?

  Right.

• 49:02Speaker 00

  And you're optimizing, you're seeing higher and higher numbers and you think that means you're doing better. But you have to kind of like get the, like you're saying, the destination in mind.

• 49:09Simon Sinek?

  Right.

• 49:09Speaker 00

  Not, not the path.

• 49:11Simon Sinek?

  So you are more visionary than you give yourself credit because you won't do anything just for the view.

• 49:16Speaker 00

  I try to keep, I try to, I will obviously be corrupted by all of these things because I will look at the data. But I will try to reorient back towards what are you trying to make?

• 49:25Simon Sinek?

  Right.

• 49:25Speaker 00

  And that's just what I deem a quality product. Based on, I hope the crowd laughs and I, as long as I believe in it, that's what I'd like to keep making.

• 49:34Simon Sinek?

  This is an interesting question, right? Which is. For, and I think a comedian is a metaphor for a lot of people, right? Which is, I want to do something and I want to be rewarded very quickly to know that I'm good. And social media can hijack and corrupt that system.

• 49:48Speaker 00

  Yes.

• 49:49Simon Sinek?

  Which we know, right?

• 49:50Speaker 00

  Because of, because of measurement.

• 49:51Simon Sinek?

  Right, it's the same feedback loop. And it's instantaneous. You get a like, you get a forward, whatever it is, you get a view, right? It's, it's, it's the same thing as a laugh, it's instantaneous. And the comedian who's obsessed with the laugh, to the point of hurting themselves or hurting others,

• 50:09Simon Sinek?

  versus having a point of view or some morality.

• 50:13Simon Sinek?

  So, what system do you have to not be hijacked by the, the click, the like, the view?

• 50:24Speaker 00

  The laughs per minute even, you're right. Because even your act can be, even in the room, be corrupted by just trying to make those people laugh as hard as you can. You want to do better than the comic before you and you're willing to do things that aren't your own standards.

• 50:34Simon Sinek?

  So what, like, what, what checks and balances are there to ensure that, yes, you're getting more laughs per minute, but there is a framework within which you're willing to operate and, and, and you're not willing to go outside, even if you could get a more, a bigger laugh?

• 50:47Speaker 00

  Esoterically, my own moral compass, my own standards, right? That's harder to measure, though. More concretely, the respect of my peers and making other comics laugh.

• 50:58Simon Sinek?

  The respect of the peers that you respect?

• 51:00Speaker 00

  Yes.

• 51:04Speaker 00

  Comedians had a moment where someone goes, "Hey, great joke." You're like, "Thanks." And you, you look at who says it, you're like, "I should cut that joke."

• 51:12Simon Sinek?

  So it's the respect of the peers you respect?

• 51:14Speaker 00

  Uh-huh. The, the, yeah, the, the people you look up to, liking what you, you can't also, you can't make that your whole thing.

• 51:21Simon Sinek?

  Right.

• 51:21Speaker 00

  Because that can also be, um, uh, uh, an unstable solution to this equation.

• 51:26Simon Sinek?

  Right. Because now you're serving their, your, their moral compass, their needs, their tastes, not yourself.

• 51:32Speaker 00

  At the expense of the crowd and at the expense of your career.

• 51:34Simon Sinek?

  Which is, which is the equivalent of, "I'm gonna do what my boss likes."

• 51:37Speaker 00

  Mm hmm.

• 51:38Simon Sinek?

  Yeah.

• 51:38Speaker 00

  I mean, again, this all translates to math for me. You have three different outputs, right? Respect of your peers, laughs for a minute, and let's say, career success. And you need to put weighted coefficients in front of each one of them and then maximize that balanced equation.

• 51:51Simon Sinek?

  And then how do you factor in the hard to measure your own moral compass? The one that you refer to as the esoteric one.

• 51:59Speaker 00

  That's harder, but because that can also, you can also.

• 52:04Simon Sinek?

  Is that just gut? Is that just feeling? Is that?

• 52:05Speaker 00

  Gut and feeling.

• 52:06Simon Sinek?

  Is that your wife coming going like?

• 52:08Speaker 00

  Revisit your earlier self and what your, what your old standards were, but also don't be so precious. You don't, I don't owe things to my 25 year old self. He didn't have better taste than I do now.

• 52:17Simon Sinek?

  But see, this is now, this is where math fails, me.

• 52:20Speaker 00

  Sure.

• 52:20Simon Sinek?

  Which is, which is, we both acknowledge that the, that the, uh, the esoteric, the intangible, the ethereal thing matters. But it's harder to measure. Nobody else can see it but you. How do you ensure that that thing has the correct weighting, which should be quite a high rating? Weighting, I mean, it should have quite a high weighting. Because we see it in the world, which is when stock price and profit and revenue are the only metric. We see ethical fading happening all over the place because the weighting is like, I believe in objectivity.

• 52:59Speaker 00

  I, I don't know.

• 53:00Simon Sinek?

  How do you do it?

• 53:01Speaker 00

  I will steal one page from a, a great comedian named Mike Lawrence, who said something to the effect of, in comedy, you're as successful as the biggest thing you say no to. And saying no to things is really me, I'm starting to really value the moments I say, I don't want to do that because

• 53:19Speaker 00

  I don't like that. That's not what I represent and that's a corruption of what I'm trying to do. And I'm going to say no to, maybe it's a branded deal or maybe it's a comedy festival somewhere.

• 53:30Speaker 00

  I guess saying no to things also, that isn't answering your question, but like,

• 53:36Speaker 00

  saying no oftentimes for principled reasons is a really good exercise. But do you have an answer? How? I'm also curious because I feel like we're losing our souls, a lot of us, through that ethical fade.

• 53:52Simon Sinek?

  Can I do an experiment?

• 53:53Speaker 00

  Please.

• 53:54Simon Sinek?

  I may be able, this may or may not work.

• 53:57Simon Sinek?

  Love the scientific method.

• 54:00Simon Sinek?

  Tell me, a festival, a joke,

• 54:06Simon Sinek?

  anything that you were involved in in your comedy career that you absolutely loved, that if everything you ever did from this point on was like that thing, you'd be the happiest person alive?

• 54:20Speaker 00

  My gut instinct is when I did Conan for the first time, I was very proud of the material I chose, and I was going to be happy either way because I did it, and then it had a pretty big positive response, which was just icing on the cake. So having both those things go my way, do

• 54:37Speaker 00

  doing the set I wanted to do with no restrictions, without having to

• 54:42Speaker 00

  dumb it down or water it down in any way, and then also getting rewarded for that, that was that was one of my happiest moments in comedy, if that answers it.

• 54:48Simon Sinek?

  But you've done things before that you were proud of, you've done things where you had control over the set, you've done things that had a bump, you know?

• 54:58Simon Sinek?

  Maybe even a bigger bump than Conan. What was it about that experience that stands out from all the ones that are very similar with very similar metrics that makes you want to talk about it now?

• 55:08Speaker 00

  It was early. It wasn't my first, but it was early. It was a show where a lot of comics I really respected were booked for, so when I saw who did it, I'm like, those are people I want to be like. Those are people who are pushing comedy to new places.

• 55:26Speaker 00

  I also got to do a set that probably would have been very much rejected by any other late night booker, and I was surprised that Conan allowed it. I said Volva eight times in a row, and that was neat to me, that the joke had information that people learned. People learned things that they didn't know from it while, while I think getting decently high laughs per minute. Probably to really answer your question, because it was the first time I did that and it paid off. And I feel like I've tried to do that every time since. And then I think maybe if there was another time my set from 2021, I was wearing a denim shirt with floral embroidery on the back. That's the only way I can distinguish the set. But I also did material that was bold for the time in terms of politically being more honest at a time where

• 56:11Speaker 00

  that could potentially get me in trouble and saying how I really felt in a way that I think other people agree with, but were afraid to say. And again, I put it out there knowing it might not make a splash at all, but it also might really connect and I felt it connecting as a result.

• 56:28Simon Sinek?

  Tell me an early, specific, happy childhood memory, something I can relive with you, not like we went to my grandparents every weekend, but something specific that I can relive with you.

• 56:34Speaker 00

  I went at 21, 23 in my 5K on a road race. I've been running a lot and the road race happened to be right in my neighborhood. So I knew the path. I'd run it most days. And I went a best time on a course that I was very familiar with. So it was middle school.

• 56:49Simon Sinek?

  Like of all the things you did that you could have told me, what was it about this run that?

• 56:55Speaker 00

  I worked really hard for it and I got a result I wanted. And also might have, might have just dipped under one of my rivals' PRs or something like that.

• 57:05Simon Sinek?

  So there's a, you are competitive.

• 57:09Speaker 00

  Yes.

• 57:09Simon Sinek?

  Any other outside of, outside of comedy, anything stand out?

• 57:16Speaker 00

  From my childhood?

• 57:18Simon Sinek?

  Childhood or even your, even your, my financial analyst career?

• 57:23Speaker 00

  A happy, happy moment.

• 57:24Simon Sinek?

  Just something you loved being a part of, something you absolutely loved being a part of.

• 57:27Speaker 00

  I do, I draw and I sculpt a little bit, but I rarely step out of the boundaries of those two media.

• 57:37Speaker 00

  But I really liked, I made the sword from Adventure Time. I really like Adventure Time. And I looked up a tutorial and I got poster board and made like a really big sword and took days to make and lots of cutting and painting and stenciling. And when it came out, it was the biggest piece of art I've ever made. It was large and that was really fun and just a weird thing to do. And no one pushing me to do it and no real reason to do it. And I did it.

• 58:07Simon Sinek?

  Okay, so here's a thread. What's interesting in all, all three of those things required a lot of work. Right? And it required a lot of self motivation. And there was no particular pressure on you for any of those things other than yourself. Right? It's a hundred percent driven by you and the hard work that you're gonna do is gonna make that set good or bad. And in each one of those cases, you're willing to do the work to the point where you find great satisfaction in that you did it your way and you did it for yourself. You said it was my personal best for this run. That it, you know, this, it was, it was, it was, there was familiarity, there was, there was a learning curve that got you there. And in all of those, there was, there was absolutely accomplishment.

• 58:48Simon Sinek?

  But you, you, it's not like, it seems to me that you're not trying to accomplish just for the sake of accomplishment. You're not driven simply to win or be the best or outdo others. It's you like, I think the reason you like a metric. It's a validation not of you or how good you are or how smart you are, how funny you are. It's a validation of the work was worth it. Right? And I think even the way you talk to be, talk to me about calculus. Which is, and the way we, the way you talk about find somebody who explains it to you in a way that you can understand. Find a better teacher. You're not dumb, you just need to find a better teacher. Which is, which is do, it's not just about grit. Cause I think the way a lot of people talk about hard work is just about grind. You're not talking about grinding. You're talking about

• 59:31Simon Sinek?

  being smart the way you learn and if you accomplish something, all of that effort of learning is worth it. And that to me is the interesting dichotomy, which is yes, you like the validation and yes, you like the laughs permitted. Yes, all of that. But all of that is, is, is actually a recognition of the hard work that you've done. You even talked about the quotes that you've made here, which is if you knew how, how, how hard it was to get here. You know, if you knew the effort that it took to get here. You'd be very, you'd be very unimpressed by whatever the quote was. And And even the way you talk to me about like you love tutoring. Because you want to teach people in a way that helps them access something. And when they get the A on the exam, or the B, or whatever it is they're striving for.

• 1:00:16Speaker 00

  When they understand the concept right there in front of me, that's the best moment.

• 1:00:18Simon Sinek?

  That's the best.

• 1:00:19Speaker 00

  Oh, that's it.

• 1:00:20Simon Sinek?

  It's the epiphany, right? And it's whatever the spark is that goes, that was worth it. The ethereal part for you seems to be in the ballpark of. You will know that you've done good work for yourself when the, when whatever the world's metrics are. Look at you and go, that's good. Well done. Well, look at your time. And that will inspire you to want to keep learning, keep pushing, keep doing more. Because you'll discover that that it's not the, it's not the, it's not the result that becomes intoxicating. It's earning the result. It's doing the hard work to get the result that becomes intoxicating.

• 1:00:57Speaker 00

  Yes.

• 1:00:58Simon Sinek?

  Which is the difference between what you're doing and winning lotteries.

• 1:01:01Speaker 00

  Yeah. I feel very considered. That was very astute. I, that, that felt very good to hear you say all of that. Thank you. Can I note a way in which I think we're actually kind of different? And I want to see if we could reconcile this?

• 1:01:13Simon Sinek?

  Yeah, and then I have to conclude, but yes.

• 1:01:15Speaker 00

  Okay, I was watching your thing about bios and people putting their biographies.

• 1:01:20Simon Sinek?

  Yeah.

• 1:01:20Speaker 00

  And you said, I want to be, how did you phrase it? It's not.

• 1:01:24Simon Sinek?

  How I want to be recognized?

• 1:01:25Speaker 00

  Yes, you want to be recognized for yourself and not for your work?

• 1:01:28Simon Sinek?

  The thing that I said was, too many people confuse their identity with their job or their accomplishments. And you can easily see it when you read someone's bio, when it says CEO of, or Oscar winning actor, blah, blah, blah. And they're telling you a position they hold, or an accomplishment they had 20 years ago. The problem is those people suffer from identity crises. Like, like without the job, without the responsibility, they literally have an identity crisis. And so I'm fine with accomplishment and I'm fine with ranks and position. But that's not your identity. And so when I write my bios, I put who I am, then what I've done. Optimist and author of.

• 1:02:10Simon Sinek?

  So I want to know, because no matter what I don't do, I'll always be that.

• 1:02:14Speaker 00

  That's wonderful.

• 1:02:15Simon Sinek?

  What advice do you give people who are told, don't give up on your day job?

• 1:02:20Speaker 00

  Don't, don't hold on to it as long as you can because it's, that's going to be what makes you interesting. You think being a musician or an actor is what makes you interesting? No, the part of you people want to hear about is those salad days and when you struggled. So I would say you are, you are building who you are as a person through that struggle. And, and money is a real thing and you need to have a way to pay your bills because if you become financially desperate, your art will be compromised instantly.

• 1:02:45Simon Sinek?

  Yeah. Any life hacks that you have that help you be more efficient, more productive personally, professionally? Anything that you, any tricks, tricks that you've learned along the way that are now?

• 1:02:56Speaker 00

  Yes. Um, biggest one for me is, uh, I subscribe to Gabor Maté's kind of, uh, uh, uh, musings about, uh, ADHD, that it's a lack of ability to validate yourself, not a lack of focus. So one thing that really helps me every day is when I sit down, I have a to-do list and I, I write a list of all the things I'm doing well. And they don't just have to be work, anything, am I recycling? Am I exercising? Am I stretching every day? Am I creative? What, all of it, no back, nothing backhanded. Well, at least I'm not doing a bad, no, no, no, I'm doing well at, you're doing great is the name of the document. You're doing great is the name of the document. Write all those things out, then start writing my to-do list.

• 1:03:36Speaker 00

  And not only will you enter that task with momentum of feeling good about yourself, the thing you're always driving towards is that, that validation. Um, you'll already have that and you work better when you like yourself. Everyone thinks they work better when they hate themselves. No, when you like yourselves, when it feels fun and you feel good about yourself, you do your best work. Uh, you also then start to get that Pavlovian rush that when I sit to open my computer, I'm already feeling good because I know it's coming and then I don't dread starting my day. I look forward to it. That's been a huge hack for me.

• 1:04:06Simon Sinek?

  Genius.

• 1:04:07Speaker 00

  Thank you. I've stolen it from many people.

• 1:04:08Simon Sinek?

  I'm, I'm, I'm gonna start that one. Uh, Matthew, I could talk to you forever. What an absolute joy to meet you.

• 1:04:15Speaker 00

  This is great.

• 1:04:15Simon Sinek?

  It was super fun and it, like I said, a kind of a personal thrill because I've gotten to know you so well from your videos. It's really, it's really, really fun to like sit across from you. I know your voice so well. Um, yeah, thank you so much for coming in. Such a joy. So much fun. A Bit of Optimism is a production of The Optimism Company, lovingly produced by our team Lindsay Garbenius, Phoebe Bradford and Devon Johnson. Subscribe wherever you enjoy listening to podcasts and if you want even more cool stuff, visit simoncinek.com. Thanks for listening. Take care of yourself. Take care of each other.