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Simon SinekSimon Sinek

The Smartest Way To Be Stupid with comedian Matthew Broussard | A Bit of Optimism Podcast

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”: @mondaypunday + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek Simon’s books: The Infinite Game: https://simonsinek.com/books/the-infinite-game/ Start With Why: https://simonsinek.com/books/start-with-why/ Find Your Why: https://simonsinek.com/books/find-your-why/ Leaders Eat Last: https://simonsinek.com/books/leaders-eat-last/ Together is Better: https://simonsinek.com/books/together-is-better/ + + + #SimonSinek

Matthew BroussardguestSimon Sinekhost
Nov 11, 20251h 4mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:002:12

    Comedy as an empirical craft: the math/science of getting laughs

    1. MB

      My love for math and my k- love for comedy and science, I don't think they're separate entities. I was not an artist by training. Uh, I think an artist creates things whose value is measured subjectively.

    2. SS

      Mm-hmm.

    3. MB

      Stand-up comedy specifically sits at an odd intersection in that y- you could almost not qualify it as art because every decision I make is focus-grouped in real time.

    4. SS

      It's empirical.

    5. MB

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

    6. SS

      And, and, and, and instant results.

    7. MB

      Instantly. Instantly.

    8. SS

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

    9. MB

      Yes.

    10. SS

      And comedy, the solution is revealed in that moment.

    11. MB

      Hypothesis, conclusion in a heartbeat.

    12. SS

      In a heartbeat.

    13. MB

      In a heartbeat.

    14. SS

      [music] 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. I was just taught badly. In this episode, we talk about curiosity, finding good teachers, and mothers. This is A Bit of Optimism. [music] 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, you- 'cause comedians pop up in my feed. Apparently the alg- algorithm knows I like funny things.

    15. MB

      Mm-hmm.

    16. SS

      And so you were ra- you were randomly thrust into my day.

    17. MB

      Mm-hmm.

    18. SS

      And, uh, I went down the Matthew Broussard rabbit hole. Like, you like one and then all of a sudden y-

    19. MB

      I'm in your face non-stop

    20. SS

      ... I'm, I'm, an hour later I'm like-

    21. MB

      Yeah

  2. 2:126:17

    From finance to open mics: choosing (and being forced into) the risky path

    1. SS

      ... "Shit, I should start work." You are exceptionally smart.

    2. MB

      Thank you. I appreciate that.

    3. SS

      Like, 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?"

    4. MB

      Uh-

    5. SS

      [laughs]

    6. MB

      Uh, my parents, uh, have, have definitely said that. Uh, I was... I, I've... Yeah. M- 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-

    7. SS

      Math

    8. MB

      ... math to make money.

    9. SS

      'Cause you talk about math principles in your comedy sometimes.

    10. MB

      Mm-hmm.

    11. SS

      So we know that you know, know math. You also seem to like science, and you have an exceptional grasp of other things, like, I guess it's part of m- memory. You just r- I mean, y- y- I mean, we were m- having coffee bef- 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.

    12. MB

      [laughs]

    13. SS

      You know?

    14. MB

      Yeah.

    15. SS

      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.

    16. MB

      Yes. Thank you.

    17. SS

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

    18. MB

      I, so I was, I think, more pragmatic about it than most. I had, uh, my first job out of college, I was working, uh, as a financial analyst, but not, not to the, the, not Wall Street. Like, easy hours, not the craziest pay, nine to five. I made spreadsheets for the most part. Um, I didn't feel a sense of, uh, 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. Um, but I started doing open mics, and I saw obviously-

    19. SS

      Just, just, just for fun.

    20. MB

      Just for fun.

    21. SS

      Yeah.

    22. MB

      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, uh, muddled at first, but there was an overall positive trend that I might have been, uh, towards the higher end of, uh, aptitude for a beginner. And I, I told myself, "Just keep noting where you stand against the ranks and how that, uh, extrapolates towards a career in this, but hold on for dear life to the career path you've worked very hard to have." 'Cause I was still young, but stepping away from that could hurt, and mean I could never potentially get back to the same-

    23. SS

      Right

    24. MB

      ... level that I was on, on track for.

    25. SS

      So you were parallel pathing it until one-

    26. MB

      As much as I could

    27. SS

      ... un- until one path revealed that this is a risk worth taking.

    28. MB

      Yes. Well, what actually happened was comedy cost me my job [laughs] in finance. So I was kind of burning the candle at both ends and-

    29. SS

      Oh

    30. MB

      ... uh, through, uh, uh, some mistakes on my part [laughs] and, and so just-

  3. 6:177:31

    Stand-up in the internet era: low barrier, high noise, new gatekeepers

    1. SS

      Yeah. I'm always fascinated by people who... I mean, show business is a hard business.

    2. MB

      Mm-hmm.

    3. SS

      And I, and, and I'm curious if the internet has made it easier or harder for you because, yes, exposure is easier.

    4. MB

      Mm-hmm.

    5. SS

      I mean, case in point, here we are because of the interwebs, because of social media. Um, but at the same time, there is so much, there are so many open mic night, you know-

    6. MB

      Mm-hmm

    7. SS

      ... little, like... And some talent, too.

    8. MB

      Mm-hmm.

    9. SS

      There's some talented people, but there's... So w- is it better, worse, or just different challenges?

    10. MB

      There's a lot to, to unpack there. Comedy is... Stand-up comedy is, the beauty of it is there's low barrier to entry.

    11. SS

      Yeah.

    12. MB

      The horror of it is there's low barrier to entry.

    13. SS

      Right.

    14. MB

      Meaning you are fighting through swarms of people. I mean, an actor at least gets, goes through acting school and has some audition process, hopefully. Musicians have to have the aptitude to play, uh, an instrument or, or sing. Uh, anyone can do it, and now anyone can post it online.

    15. SS

      Comedy is like anyone can stand on the stage and perform.

    16. MB

      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.

    17. SS

      Yeah.

    18. MB

      You have to... To, to be good, you have to be on stage a lot, but to be on stage a lot, you have to be good.

    19. SS

      Right.

  4. 7:319:04

    Building a fan base with clips: repurposing legacy TV sets for TikTok/IG

    1. MB

      So it's a very difficult track to get started in. Uh, the internet, though, the interesting thing with the internet was I was very fortunate in the early days of my stand-up, I was, uh, favored by the industry, Comedy Central, uh, uh, Conan. I, I got put on a lot of shows, um, which was nice. It didn't translate into having a fan base. Those were the, the waning days of, of media. Uh, not for me at least. Uh, some luck, some, some recognition, but I wasn't selling a ton of tickets off of that.

    2. SS

      Mm-hmm.

    3. MB

      Uh, social media wasn't the way comedians were exposed back then. Uh, and then the pandemic hit, and then that was really the end of that. You, those, those things don't make stars anymore. Uh, I've never been on Netflix. That might be a route, but even that's becoming less of a sure thing. Uh, things changed for me on the business end when during the pandemic I realized Comedy Central was, uh, asleep at the wheel in terms of copyright issues. 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, uh, 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 and rather than say, feeling defeated by this, looking at it as an opportunity-

    4. SS

      Yeah

    5. MB

      ... to use that footage to... You know, I, I, 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, uh, an audience for myself, and that, that worked to, to an extent.

    6. SS

      To an extent. Wh- why is it... And obviously talent- that's where, that's where the wheat and the chaff separate-

    7. MB

      Mm-hmm

    8. SS

      ... because you get more likes, you get more forwards-

    9. MB

      Mm

    10. SS

      ... the algorithm favors you, you'll do better.

    11. MB

      Mm-hmm.

  5. 9:0412:50

    Do comedians make great actors? Vulnerability vs silence and the need for feedback

    1. SS

      You'll get a, you'll get a following. W- I have this theory, which I'm... That I think comedians make great actors.

    2. MB

      Mm-hmm.

    3. SS

      Uh, you know, you look at people w- who, with backgrounds in comedy that became great actors, you know, Jim Carrey, um, uh-

    4. MB

      Robin Williams

    5. SS

      ... Robin Williams, um, uh, Jamie Foxx.

    6. MB

      Mm-hmm.

    7. SS

      The- these are comedians.

    8. MB

      Michael Keaton.

    9. SS

      Michael Keaton. Really?

    10. MB

      Was a stand-up.

    11. SS

      Was he really?

    12. MB

      Yes.

    13. SS

      Uh, uh, Tom Hanks started doing comedy.

    14. MB

      Yeah.

    15. SS

      Not a stand-up, but that was his, it was...

    16. MB

      Yeah.

    17. SS

      So all of these, e- especially the ones who did stand-up, Michael Keaton, didn't know, especially ones who do stand-up, I th- I think they have the ability to become great actors because they get... This is my theory, because, um, vulnerability and humiliation are something they're, they're attuned to. Like-

    18. MB

      Yeah

    19. SS

      ... 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 the, what an act- a great actor has to tap into-

    20. MB

      Mm-hmm

    21. SS

      ... is the ability to be that vulnerable, that sort of pers- to persevere.

    22. MB

      Mm-hmm.

    23. SS

      And comedians just have a good training to be good actors. Comment. [laughs]

    24. MB

      Can I disagree?

    25. SS

      Of course.

    26. MB

      Okay.

    27. SS

      It's a theory.

    28. MB

      It's a great theory. I, I think-

    29. SS

      Theories are, are to be tested.

    30. MB

      I think you're right and the, the, the beauty of comedy is the humiliation, is the vulnerability. I think... I, I, I really don't think great comedy can last very long without that, without that, um, 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, uh, because of being a stand-up comedian. Uh, 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?

  6. 12:5015:36

    Validation, insecurity, and adrenaline: bug or feature?

    1. SS

      The little N narcissism, not big N narcissism. But there's a, there's a little N narcissism to that, right?

    2. MB

      Mm-hmm.

    3. SS

      Which is, which is feed me, feed me, feed me.

    4. MB

      Mm-hmm.

    5. SS

      Right?

    6. MB

      I think a lot, yeah. [laughs] I think-

    7. SS

      Like, 'cause-

    8. MB

      ... a constant need for validation, yeah.

    9. SS

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

    10. MB

      Oh, uh-

    11. SS

      If-

    12. MB

      ... 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 hole. Uh, and I think it's probably common in other entertainers and potentially even business people.

    13. SS

      Yeah.

    14. MB

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

    15. SS

      Some, some, some, some of the, some of the-

    16. MB

      Yeah

    17. SS

      ... I think the ones that are more money driven.

    18. MB

      Mm-hmm.

    19. SS

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

    20. MB

      Mm-hmm

    21. SS

      ... 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.

    22. MB

      Mm-hmm.

    23. SS

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

    24. MB

      It's the only yardstick they can find.

    25. SS

      It's the, it's, it's, it's, and it's an, and an, and it's an empirical yardstick, and it's a measurable yardstick. It's a me- it's a yardstick that they can hold up to somebody else and be like-

    26. MB

      Mm-hmm

    27. SS

      ... "See?"

    28. MB

      Mm-hmm.

    29. SS

      Right?

    30. MB

      Mm-hmm.

  7. 15:3620:34

    Impact vs results: Simon’s infinite mindset, momentum, and the iceberg metaphor

    1. MB

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

    2. SS

      So I am driven... The, the, the hard thing for my work is it, and when you, when you make the difference between sort of the, the, the, 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.

    3. MB

      Yes.

    4. SS

      But the thing that, that drives me is, is impact. What means the most to me is that I'm undoing everything Jack Welch ever did.

    5. MB

      [laughs]

    6. SS

      Like, I want to reverse everything that man broke in capitalism.

    7. MB

      The why.

    8. SS

      Yeah.

    9. MB

      Yeah.

    10. SS

      But like I have a, I have a, I'm chipping away.

    11. MB

      Mm-hmm.

    12. SS

      You know? And m- and, uh, like the, the people that drive me and inspire me, so like the, all the founding members of the American women's suffrage movement-

    13. MB

      Mm-hmm

    14. SS

      ... all died before the first woman voted. None of them, none of them, none of them lived to see a woman vote.

    15. MB

      Uh-huh.

    16. SS

      What I'm, what, the reason that inspires me is they still never gave up.

    17. MB

      Mm-hmm.

    18. SS

      It was never in their grasp-

    19. MB

      Mm-hmm

    20. SS

      ... yet they continued because their metric was momentum, not result. They obviously wanted the result. They would've preferred it happened in their lifetime.

    21. MB

      Mm-hmm.

    22. SS

      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.

    23. MB

      That's-

    24. SS

      That to me is super inspiring.

    25. MB

      That's very noble. That's really wonderful. I think my ego is too strong-

    26. SS

      [laughs]

    27. MB

      ... that I, I need to see it and get credit for anything I'm a part of [laughs] So I'm not a good person.

    28. SS

      You, you-

    29. MB

      But that's lovely. It's like, it's like generational starships. That's, I, I read a lot about, like in sci-fi, it's like, uh, it's a common thing in sci-fi. A, a, a spaceship will take off towards whatever other star, and the original inhabitants know they will die before it gets there-

    30. SS

      Right

  8. 20:3424:58

    A calculus primer and a bigger point: you’re not bad at math—you were taught badly

    1. SS

      Oh, thank you very much. [upbeat music] Do you still do math?

    2. MB

      Yes. Yeah.

    3. SS

      Like, for fun?

    4. MB

      I tutor.

    5. SS

      Oh.

    6. MB

      Which is great through-

    7. SS

      At what level?

    8. MB

      Uh, I'm lucky. There's, there's, there's this volunteer organization I work through, uh, college.

    9. SS

      Uh-huh.

    10. MB

      So I agreeably go for kind of the classes at very much the end of my range.

    11. SS

      Uh-huh.

    12. MB

      Uh, 'cause those are more fun than going back to the earlier stuff. But, uh, college, a lot of, like, engineers. Um, calculus, calc two, calc three, linear algebra.

    13. SS

      Wow.

    14. MB

      Um, those are the fun stuff. I'm trying to do something a l- uh, I think it's, like, maybe, like, uh, partial differential equations this semester, and I'm, like, really having to catch up between sessions [laughs] on stuff I didn't learn that well the first time, so.

    15. SS

      It is amazing how opposite we are.

    16. MB

      You don't like math?

    17. SS

      Um, I don't dislike it. I, I don't have an instinct for it. Like, I can, I can... I never-- I'm very proud of this, actually. I 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.

    18. MB

      Mm.

    19. SS

      I, I understand algebra.

    20. MB

      It's heartbreaking.

    21. SS

      I understand geometry. Um, uh, and trigonometry, you start to lose me.

    22. MB

      Trigonometry sucks.

    23. SS

      Okay.

    24. MB

      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-

    25. SS

      But calculus I know nothing about.

    26. MB

      Calculus is a function. The function is you put in X, you get a Y, right?

    27. SS

      Yeah.

    28. MB

      And you can get a curve with that, right?

    29. SS

      Yeah.

    30. MB

      Yeah. Calculus is just, well, how steep is that curve? That's it.

  9. 24:5831:34

    Learning without self-blame: find seven explanations, embrace feeling stupid

    1. SS

      ... or the way I explain an idea... 'Cause, 'cause I, 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 com- 100%. I m- there is not a, a, an ironic m- m- nothing, there's nothing ironic about that. Which is, uh, as a kid with ADHD in, in high school, I struggled to read, I stuggled, struggled to study. I couldn't learn by rote. Like, and so I still gotta pass high school.

    2. MB

      Mm-hmm.

    3. SS

      So you have two options. Fail or figure it out.

    4. MB

      Mm-hmm.

    5. SS

      So what I learned to do was be really good at asking questions, get really good at, at, at listening. I had to attend class, I couldn't cut school.

    6. MB

      Mm-hmm.

    7. SS

      'Cause if I cut... And when I was in college, I had to choose professors who were good at explaining, 'cause I could never rely on the book to catch up.

    8. MB

      Yeah.

    9. SS

      Right? And that skill of learning to survive and, and, and, and ch- turn my ADHD into an advantage rather than a, than a, than a, a deficit-

    10. MB

      Mm-hmm

    11. SS

      ... um, 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 any fear.

    12. MB

      Mm-hmm.

    13. SS

      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, and I'll say, "Is this what you're trying to say?" And I'll say it in simple terms that I can understand.

    14. MB

      Yeah.

    15. SS

      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.

    16. MB

      Yeah.

    17. SS

      So simple that not only do I understand it, but I can then tell somebody else-

    18. MB

      Yes

    19. SS

      ... and then they go, "Got it."

    20. MB

      Mm.

    21. SS

      And I get all the credit, which is not fair-

    22. MB

      Mm

    23. SS

      ... 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-

    24. MB

      Mm

    25. SS

      ... then I can't understand it 'cause I don't have that analytical kind of mind that just understands, you know, sort of math and equations.

    26. MB

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

    27. SS

      No, no, no. People do.

    28. MB

      Sure.

    29. SS

      People can do math in their heads very easily.

    30. MB

      No, no. W- No. I, I, like, th- 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, a- anyone who studies math is, is, is constantly bombarded by f- frustration, but you embrace the frustration. You know that you're going to feel pain-

  10. 31:3435:25

    Comedy craft realities: slow progress, crowd work challenges, and why vulnerability works

    1. MB

      Um, I've also been reading math textbooks, uh, just to learn things I've always wanted to learn. At, at a snail's pace, but something I didn't realize was I thought I was just not good at reading math textbooks, 'cause 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 and you get across the pool and you're like, "That was easy," and then you can't make it to the next wall.

    2. SS

      Right.

    3. MB

      And then I talk to someone who's a math PhD, they go, "That's how it is. One page a day is, is a great rate. It's just that hard."

    4. SS

      Wow.

    5. MB

      And, and the people who accomplish it forget how hard it was or want you to think they're smart-

    6. SS

      Right

    7. MB

      ... 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.

    8. SS

      Yeah.

    9. MB

      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, what's, what's... Uh, who, whose famous line, "If you saw the work put into it, it would not be impressive at all?"

    10. SS

      Yeah, yeah.

    11. MB

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

    12. SS

      My process is-

    13. MB

      ... not easy

    14. SS

      ... it's, it's, my process is a little different.

    15. MB

      Mm-hmm.

    16. SS

      Um, I, I'm curious, I'm curious, are you good at crowd work? Like-

    17. MB

      No.

    18. SS

      Okay.

    19. MB

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

    20. SS

      Okay.

    21. MB

      Mm-hmm.

    22. SS

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

    23. MB

      It's cool.

    24. SS

      It's a thing to behold.

    25. MB

      They're patient. They have... It's, that's, that's, like, a, a real zen state.

    26. SS

      Yeah.

    27. MB

      You have to be calm and 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.

    28. SS

      Yeah.

    29. MB

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

    30. SS

      One, one thing that I love about your work, um, is first of all, super vulnerable. Like, you share things [laughs] 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-

  11. 35:2538:51

    From edgy to self-deprecating: leadership lessons and choosing a ‘victimless’ joke target

    1. SS

      Was that always, were you always that kid that didn't mind being embarrassed, that didn't mind being vulnerable?

    2. MB

      No.

    3. SS

      Like, so how did you learn it?

    4. MB

      Uh, kinda through stand-up. Early on in stand-up, I was just trying any... I, I try- when I started, I wanted to be brash and offensive 'cause I thought that was cool.

    5. SS

      Andrew Dice Clay style?

    6. MB

      Yeah. And, and I, I, I kinda 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. Um-

    7. SS

      Did it get laughs?

    8. MB

      Sometimes.

    9. SS

      Yeah.

    10. MB

      Sometimes in front of other people who liked, who liked that. Um, I [laughs] of all people, James Comey's memoir, uh, was, was, uh-

    11. SS

      [laughs]

    12. MB

      ... it really shaped me. There was one chapter... Uh, I, I, I can't imagine a less funny person than former FBI director James Comey.

    13. SS

      [laughs]

    14. MB

      But he had, uh, I, I think it was... It, it goes to speak of how not funny people can sometimes have the best observations about comedy. Um, he had a whole chapter talking about the sense of humor, uh, uh, of the three presidents he worked under.

    15. SS

      Right.

    16. MB

      Which is Bush, uh, Bush Jr... 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, uh, equate to good leadership, versus Obama would make jokes at the expense of himself, which would uplift others and bring out the best in them. So, uh, sure.

    17. SS

      Maybe.

    18. MB

      Yeah.

    19. SS

      But, but, but anyway, moving on.

    20. MB

      Sure. Okay.

    21. SS

      Moving on.

    22. MB

      Well, ignoring the politics of that-

    23. SS

      Ig- ignoring the politics of, of the comment.

    24. MB

      Yes.

    25. SS

      I, I, I get it.

    26. MB

      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.

    27. SS

      Right.

    28. MB

      Um, it's fun for everyone.

    29. SS

      There's no vi- it's a victimless crime.

    30. MB

      Mm-hmm.

  12. 38:5140:26

    Mining family for comedy: the airport ‘master’ line and the birthday card backlash

    1. SS

      Huh. And now, um, it's... And, and does your mom [laughs] know the way you talk about her?

    2. MB

      Yes. Uh, she's, uh, fortunately very, uh-

    3. SS

      She's-

    4. MB

      She, she doesn't mind it.

    5. SS

      She sounds like an absolute caricature.

    6. MB

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

    7. SS

      Oh, I saw the airport story. [laughs]

    8. MB

      Yeah. I, I, there's, there's, I... [laughs] That's... I, I can't stress how true that story is.

    9. SS

      Do, do you wanna tell the airport story for those who haven't seen it on the YouTube-

    10. MB

      Uh, I'll, I'll, I'll give the introduction

    11. SS

      ... on Instagram?

    12. MB

      I was, I was dropping her off at the airport-

    13. SS

      [laughs]

    14. MB

      ... and, uh, had to, uh, shortly thereafter come back and pick her up. Uh, she went to check in. Uh, they were giving her trouble over paperwork for bringing a dog on the plane. [laughs] And she forgot the w- 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.

    15. SS

      Yeah.

    16. MB

      Um, she signed off on that. I said, "Are you, uh, can I talk about that on stage?" She goes, "Yeah, it's funny."

    17. SS

      It is funny.

    18. MB

      So, yeah, I'm like, "You, you sure about that?" She's like, "Yeah." The one thing she doesn't like is the birthday card, which I recommend, uh... I can't do it here, but-

    19. SS

      Yeah

    20. MB

      ... a birthday card she sent to my, my wife. Um, I j- 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-

    21. SS

      Yeah

    22. MB

      ... as I read it verbatim.

    23. SS

      Yeah.

    24. MB

      And she goes, "Why are they laughing? I don't like this. What are they laughing at?"

    25. SS

      Yeah.

    26. MB

      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-

    27. SS

      Yeah

    28. MB

      ... but keep to ourselves."

  13. 40:2647:22

    Ambition, live connection, and what’s next: sitcom dreams and the irreplaceability of in-person laughs

    1. SS

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

    2. MB

      The, I, I'm not ambitious enough.

    3. SS

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

    4. MB

      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-

    5. SS

      What, what do you mean by farther along? Like, like-

    6. MB

      I don't know. Uh-

    7. SS

      Like, what does that even mean?

    8. MB

      Be on TV, uh, have, be on a TV show and bigger crowds.

    9. SS

      Is that a thing now? But is that... I mean, it's, like, but you don't wanna act.

    10. MB

      I would love to. I love acting.

    11. SS

      Oh, okay.

    12. MB

      I just find it challenging and not as natural for me.

    13. SS

      Okay, okay, okay.

    14. MB

      I love acting.

    15. SS

      Okay.

    16. MB

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

    17. SS

      Okay.

    18. MB

      And I've really accomplished most of that. I could... 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."

    19. SS

      Right.

    20. MB

      Uh, I'd love to be on a sitcom. That's always been my dream.

    21. SS

      Okay.

    22. MB

      'Cause tho- 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. And obviously, I wanna keep making specials. That would be really cool to, to keep putting out long-form stand-up content.

    23. SS

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

    24. MB

      I don't think so.

    25. SS

      Is... Yeah.

    26. MB

      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.

    27. SS

      Yeah.

    28. MB

      It's this synthetic connection-

    29. SS

      Yeah

    30. MB

      ... these empty calories-

  14. 47:221:01:20

    Optimization and ethics: metrics can corrupt—so what keeps you honest?

    1. MB

      This ties back to calculus.

    2. SS

      Say more.

    3. MB

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

    4. SS

      Yeah.

    5. MB

      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 at the top. Well, 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-

    6. SS

      Right

    7. MB

      ... 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.

    8. SS

      Right.

    9. MB

      That is, that is [chuckles] uh, actually the math of it. Um, the problem is what if there's another hill next to you that's higher? 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, we were talking earlier about the, uh, 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.

    10. SS

      Right.

    11. MB

      What if you get it wrong? And a lot of people do. What if, what if, uh, I'm doing well because I'm-- If, what if you flip it, those views are the measure-

    12. SS

      Right

    13. MB

      ... and now you do everything you can to optimize that-

    14. SS

      Right

    15. MB

      ... you're going to do a lot of things that are

    16. SS

      Clickbaity things

    17. MB

      Bad things

    18. SS

      Yeah

    19. MB

      Just not, not in the intention of what you wanted to create originally.

    20. SS

      Right.

    21. MB

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

    22. SS

      Right.

    23. MB

      Not, not the path.

    24. SS

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

    25. MB

      I try to keep... I try to-

    26. SS

      There is-

    27. MB

      I, 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?

    28. SS

      Right.

    29. MB

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

    30. SS

      This is an interesting question, right? Which is for... And, and I think a comedian is a metaphor for a lot of people.

  15. 1:01:201:04:52

    Identity vs job and an ADHD productivity hack: ‘You’re doing great’ before the to-do list

    1. SS

      Yeah.

    2. MB

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

    3. SS

      How I wanna be recognized?

    4. MB

      Yes. You wanna be recognized for yourself and not for your work?

    5. SS

      The thing that I said was too many people, uh, 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-

    6. MB

      Mm-hmm

    7. SS

      ... blah, blah, blah, and they're telling you a position they hold or an accomplishment they had 20 years ago.

    8. MB

      Mm-hmm.

    9. SS

      The problem is those people suffer from identity crises. Like, like without the job, without the responsibility, they literally have an identity crisis.

    10. MB

      Mm-hmm.

    11. SS

      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.

    12. MB

      Mm-hmm.

    13. SS

      Optimist and author of.

    14. MB

      Mm-hmm.

    15. SS

      So I wanna note, because no matter what I don't do, I'll always be that.

    16. MB

      That's wonderful.

    17. SS

      What advice do you give people who are told, "Don't give up on your day job"? [laughs]

    18. MB

      Don't. Don't. Hold onto it as long as you can because it's g- 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 p- you, people wanna 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 [laughs] 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.

    19. SS

      Yeah. Any life hacks that you have that help you be more efficient, more productive, personally, professionally? Anything that you-

    20. MB

      Yes

    21. SS

      ... any tricks, tricks that you've learned along the way that are now-

    22. MB

      Yes. Um, biggest one for me is, uh, I subscribe to Gabor Mate'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. 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 what's coming, and then I don't dread starting my day. I look forward to it.

    23. SS

      Mm.

    24. MB

      That's been a huge hack for me.

    25. SS

      Genius.

    26. MB

      Thank you.

    27. SS

      I'm-

    28. MB

      I've stolen it from many people. Thank you

    29. SS

      I'm, I'm, I'm gonna start that one. Uh, Matthew, I could talk to you forever. The, the-

    30. MB

      That's fine

Episode duration: 1:04:53

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