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Kelly Leonard on How to Use 'Thank You, Because' to Disarm Disagreement

Aug. 3, 2022

Kelly Leonard on How to Use 'Thank You, Because' to Disarm Disagreement

"The world we live in right now, no one wants to work together. It's never been this bad, in my experience. If we could just enter rooms with curiosity instead of blame, if we could enter rooms with a 'Thank You, Because' orientation, I think we have a shot." - Kelly Leonard

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In a world of increasing polarization, Kelly Leonard is working to bridge the divide and bring people together by teaching the power of improv. In this episode you will learn:

1. The importance of play, especially as we get older.
2. The power of "Yes, And" to create agreement and understanding.
3. The importance of a shared humanity that includes people who may not think or vote like we do.

"The world we live in right now, no one wants to work together. It's never been this bad, in my experience. If we could just enter rooms with curiosity instead of blame, if we could enter rooms with a 'Thank You, Because' orientation, I think we have a shot."- Kelly Leonard

Kelly Leonard is the Executive Director of Learning and Applied Improvisation at Second City Works. His book, “Yes, And: Lessons from The Second City” was released to critical acclaim in 2015 by HarperCollins and was praised by Michael Lewis in Vanity Fairwho called it “ excellent guide to the lessons that have bubbled up in Second City’s improv workshops.”

Kelly is a popular speaker on the power of improvisation to transform people’s lives. He has presented at The Aspen Ideas Festival, The Code Conference, TEDx Broadway, Chicago Ideas Festival, The Stanford Graduate School of Business and for companies such as Coca Cola, Microsoft, Twitter, Memorial Sloan Kettering and DDB Worldwide.

Kelly co-created an initiative with the Center for Decision Research at the Booth School at the University of Chicago, The Second Science Project,that looks at behavioral science through the lens of improvisation. He also hosts the podcast, “Getting to Yes, And,” for Second City Works and WGN radio that features interviews with academics, authors and leaders such as Brene Brown, Adam Grant, Michael Lewis, Lindy West, Ash Carter and Amy Edmondson.

For over twenty years, Kelly oversaw Second City’s live theatrical divisions where he helped generate original productions with such talent as Tina Fey, Stephen Colbert, Amy Poehler, Seth Meyers, Steve Carell, Keegan-Michael Key, Amy Sedaris, Adam McKay and others.

In 2019, Arts Alliance Illinois awarded Kelly and his wife Anne Libera with their Creative Voice Award.


Paul Vato is an on camera and voice actor, improvisor, podcaster and entrepreneur.

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Kelly Leonard

Paul Vato: [00:00:00]

Ladies, gentlemen, welcome to Paul Vato presents. I am your host, Paul Vato and today my very special guest is Mr. Kelly Leonard. He is the creative director of Applied Improvisation at The Second City Works?

Kelly Leonard: That's it.

Paul Vato: Is that the title?

Kelly Leonard: Yeah, whatever, I've been there a long time.

Paul Vato: Yes, and, yes, and, that's it? Kelly, thank you so much for sharing a little bit of your time with us here on Fireside and then I will convert this into a podcast that will hopefully be seen and heard all over the world. So I sincerely do appreciate you being here and thank you very much.

Kelly Leonard: I am happy to be here and I always need more technology in my life to try to master.

Paul Vato: I sense that you might be a little sarcastic with that comment because I know every time a new app pops up, I'm like, ugh, not another one! I discovered Fireside, it's owned by Mark Cuban and it's a great app.

Kelly Leonard: It's very cool. I had to do a thing on Substack, I was like, what? And then I actually deleted my [00:01:00] TikTok App. I can't do it. I've decided.

Paul Vato: I'm sure that people that know TikTok would tell you that you would kill it on TikTok, but it's like anything else have to post daily if you're looking to grow your TikTok or Instagram, it's not just kids dancing.

Kelly Leonard: Oh no, it's huge.

Paul Vato: The wealth of knowledge that you have would really benefit people on TikTok. I think they would love to hear from you, it's another thing that you have to do, so I get it.

Kelly Leonard: You only have so many hours in the day and you have to figure out where you're gonna put your attention, it's always such a noisy world that we live in and certainly the work that I've done both at Second City and improvisation and comedy, but also working with behavioral science community has taught me I really need to focus on where my attention is and I want that on, mostly on other people, friends, family, in nature and in play. We get old, we get older and we have less and less opportunities to play and that's not good for us.

Paul Vato: That's great that you would say that I've spoken to several people, especially from my early days there at Second [00:02:00] City and in the Chicago improv scene and that seems to be a recurring theme as we get older, we forget that we have to play that we should be playing and Del Close used to mention that as we got older, we forget to play and we have to allow ourselves to do that so thank you bringing that up and hopefully reminding the people that are listening to this, you have to play even as we get older, so thank you.

Kelly Leonard: Yeah, sure.

Paul Vato: Let's start maybe at Second City and where you grew up and things like that and I think I already know the answer, tell us a little bit about your family and if they were maybe supportive of the career choices that you've made and things like that. I guess let's maybe put it out there, your father was a Chicago icon, Roy Leonard. I grew up listening to him on WGN, I'm sure that there's a lot of other things , I finally, when I put the two and two together or found out, the internet wasn't as prevalent in the 19 hundreds. It wasn't like you could search someone. Would you mind touching a little bit on that and talking a little bit about your family?

Kelly Leonard: Yeah. So my dad had a television and radio career, in Boston. That's where he started [00:03:00] out that's where he met my mom and his station went rock, and he hosted a talk show so he started sending out his tapes of him on the air and he got an invitation to come sub for Wally Phillips for a week. So Wally Phillips, back in the day, was the top rated radio guy. He had something like a 46 share, which is just no one has that anymore, it didn't exist, so my dad did well and they offered him the show right after Wally so he moved. We were first in Deerfield, I'm the youngest of six kids so I was a baby when we moved, we were in Deerfield for a year and then they bought a home in Kennelworth. We were, I think, Jimmy Carrane's family were the first Catholics in Kenworth right before us. We were the second Catholic family to move in, it was very different in those days.

Being the youngest of six to a dad who, went to a ton of theater and movies and concerts, it was great. I got exposed to so much different kind of culture and really what was funny is most of my brothers went into very respectable jobs, like banking and architecture and [00:04:00] newspaper business, and then when I came home after my last day of college and said to my dad, I wanna be a playwright, he was like, finally, one of my kids wants to get into the entertainment industry, cuz that's what he always loved. So no, he was really supportive and what he did for me, he got me two informational interviews. I interviewed with Roche Schulfer at the Goodman, who's the Executive Director, still, there, and Bernie Sahlins, who was the co-founder of Second City, he had sold Second City by that time and was building a new theater called the Willow Street Carnival and Bernie offered me a job on the spot. He said, come work for me, it starts in six months and I'll get you a gig at Second City in the meantime. Of course, I thought I was gonna be like VP of Marketing, so I show up and I'm escorted to the back bar and I'm a dishwasher, which is just a horrendous job. The other guy who got hired the same week that I did was Jon Favreau, the film director ,and we both had mullets. That's how I started out.

Paul Vato: So this "nepotism" didn't quite work out to your liking right away, if you will, because here you are thinking, oh, I'm gonna, I'm [00:05:00] gonna go right to the front office and they're like getting in the back kid.

Kelly Leonard: Yeah, exactly. No, it was terrible. Look The Second City in those days was filled with alcoholics and sociopaths, so I learned a lot. Mike Myers and Bonnie hunt were on the Main Stage, Jane Lynch was in the ETC, Chris Farley had just been hired in the touring company. It was an amazing time to learn and did not know that Second City created it's show through theatrical improvisation. I was aware of improvisation in a variety of other contexts. I was a Deadhead, I love Jazz, and I did my thesis on the Beat Writer, Jack Kerouac in his spontaneous beat prosody, basically improvisational writing. So I had a yen for that work, but just didn't know how it expressed itself in theater and comedy, and, you work at Second City and you get an education of a lifetime, figuring out how this stuff works, how it gets put together, how it gets taken apart.

I was still writing plays. I moved up to hosting. I then worked in the box office. I left to go work for the Willow Street Carnival, which was a disaster and it folded, and that's why I came back and worked in the [00:06:00] box office, and was trying to write that whole time, and in 1992, outta nowhere, I got offered the job as Associate Producer of The Second City and I took it.

Paul Vato: You truly worked your way up the ranks and almost rather quickly, cuz you started there what, in 88?

Kelly Leonard: Yeah. Yeah. So Joyce Sloan, who was the producer before me, had a series of heart attacks and strokes and I think she always thought her daughter Cheryl would take over, but Cheryl had left the business by then and honestly, there wasn't anyone, and I showed up on time. I'm very lucky in that I was in the right place at the right time. Not that it was easy. The first few years were real tough but I figured out the job and and I think I had a pretty good run.

Paul Vato: You absolutely did. How long were you there in that capacity, was there another promotion and then ultimately...?

Kelly Leonard: Associate Producer to Producer, to Vice President, Executive Vice President of The Second City and then I founded a division called Second City Theatricals that did plays and musicals and other kinds of performance pieces[00:07:00] that still exists today and I did all of that basically from 92 to 2015 when I co-wrote the book, "Yes, And" with Tom Yorton, who runs our corporate division, and then I stepped down. I didn't really know what I was going to do, I just knew I didn't want to keep doing the thing I was doing, and I was able to make this pivot inside the organization after about a year and said, I'm really interested in the learning space. I'm interested in academic insights that would support the theories that we have about why improvisation is so important in life, in business, in collaborating and creativity and innovation. And I started a project called the Second Science Project at the University of Chicago, working with some amazing scientists and all this then reflected back to what I do now, which is in addition to hosting the podcast for Second City and doing a lot of speaking dates and a lot of writing and I do a lot of business development. I find interesting partners for us and we create new stuff, and that's just something that I've always enjoyed doing and I did it for so long on stage. Now I do it off stage.

Paul Vato: I love the way that [00:08:00] you've brought together the world of this education, but a scientific approach to improv. Is this only for students at the University of Chicago or is there a course or is there something that you're developing?

Kelly Leonard: We did the Second Science Project for four years and what we developed was a series of orientation programs for University of Chicago, undergrad, grad, and the law school uses them now, we created the executive education program, so we take this out into the corporate world. I think we're about to start it back up with UCLA. My partner, Heather Caruso, who used to be at University of Chicago is at UCLA, we're talking about restarting it. It's many domains, right? We can bring it into the classroom and the Training Center, we can take it to our corporate learning spaces and the thing I love about it is in addition to these programs, we're doing studies.

We have a study, I think it's coming out next year, the concept of "yes, and" and when we teach this exercise, there's already tons of literature and evidence in academia to support why it makes sense, chiefly in behavioral economics, we know that people's default setting is to do nothing or say no, and "yes, and" is like a [00:09:00] nudge to do the other and it's a stepping stone in creativity.

The scientists, we work with ask the question, what happens when what's the prompt for when you don't wanna "yes, and" someone, when you're fundamentally in disagreement, but you need to stay inside the conversation. We discovered, sort of together, that the prompt is "Thank you, because", so if someone disagrees with you, thanking them for their opinion means that they're not, you're not setting off the fear part of the brain or the defensive part of the brain and the "because" is you find some point of agreement, no matter how small, it's usually foundational or purpose driven, things like that and then if you both do that, you have such a better opportunity to get to a place of some form of agreement or understanding, and this is such a powerful technique. We did it with thousands of people, that's why the paper's taking so long to come out, but the world we live in right now, like no one wants to work together. It's never been this bad, like in, in my experience and if we could just, enter rooms with curiosity, instead of blame, if we could enter [00:10:00] rooms with a "Thank you, because" orientation, I think we have a shot at doing this, the reverse is anarchy. And this is not to say, we need to let oppressive systems for individuals, get away with it. We don't. But I think most people want the same stuff, they don't wanna be harmed, they want people to be nice to each other, they wanna live in comfort, all these things.

Dan Gilbert is a professor at Harvard who's quite brilliant and he says that, we share so much more as human beings than we don't that if an alien came down and met one human being, they'd understand 90% of humanity, so we should be able to do this and not be at each other's throats.

Paul Vato: Wow. That's some powerful stuff. It's the first time I'm hearing of Thank you, because", and you're right, it automatically disarms you a little bit, now I'm not gonna go into that defensive of just arguing and not listening and not being in the moment, that's some brilliant stuff. Where can people read about this somewhere or where can we follow along in this journey or, and you're also available, I would imagine to speak at gigs and where can people find you, Kelly, what's the best place?

Kelly Leonard: They can find me on [00:11:00] LinkedIn and Twitter are probably the two places, my podcast drops every Tuesday. We talk with a variety of scientists, academics, creative people, business leaders, about these kinds of ideas. I write about them on places like LinkedIn and Twitter, my Twitter handle is KLSecondCity. Just look up by name on LinkedIn. I love people to connect. Second City gets hired. The Second City works, which is the B2B arm of The Second City, we do hundreds, like anywhere from 500 to 600 learning engagements all over the world, every year. We did the pivot, like everyone else did to virtual, we are back live I'm getting booked like crazy now in live spaces, I think people are realizing what they missed. It was amazing that we could do this. So it was amazing that we could make that pivot. There's a lot of stuff about it that's terrific. But there's nothing that beats human beings in a room together.

Paul Vato: That's a hundred percent I'm in Vegas right now and everything is coming back, we have a big cigar convention. I'm in the cigar world as well.

Kelly Leonard: Yep.

Paul Vato: There's a big cigar convention going on right now and it's so great to see [00:12:00] everyone back and in person and, we still have to be careful, I think, but it's it is, it's so refreshing. I'm glad that we were able to survive and do it through the virtual world, but you're right, we're coming back and hopefully a hundred percent. So that's wonderful. Thank you, thank you for sharing that.

Now you mentioned something that was funny. It's funny that Carrane's family was the first Catholic family in Kennelworth.

Kelly Leonard: Yeah.

Paul Vato: What was there before, or what was the predominant...?

Kelly Leonard: Oh, Protestant, White Protestant. So we were the second Catholic family. There was a black family that moved down the street from us, that was the first one in, and this is in the Seventies and I think and slowly a Jewish family. It's more diverse now, it's not that diverse. Kenworth could be referred to as one of these "sundown communities", which is a term for the sort of racist policies of, not letting, you know, people of color and people from diverse communities buy real estate in those places and that was prevalent in the North Shore (of Chicago). I am, of course, it would be no surprise, as you are, [00:13:00] on the left liberal spectrum. The sort of intolerance that our folks complain about on the right, I think I wish there was a little more self-awareness of the intolerance that exists on The Left as well and I think because of the systemic oppression that has, that we see, and we understand and was horrible and we need to change and we need to challenge that can live in concert with being kind. I know the activists who I'm close with, and I'm close with many people in the activist community in particular, Ai-jen Poo, who's part of Super Majority is one of our, my wife and I are best friends and her colleagues, are kind, they fight but they laugh and they talk to people who think differently than them, and they don't see that as a threat, they see it as an opportunity. There's so much change that needs to happen and we've become woke, we've woken up to a lot of the shit. And that's important that we not stop fixing that stuff, these big problems, it's just that we can't let that take away from this idea of a shared humanity, that includes lots of different people who may not [00:14:00] think or vote like we do and that is okay. I grew up not very far from Highland Park. My mom shopped at the Sunset Foods, the grocery store that was right near where that shooting took place on Monday and these events just don't stop happening. I think there's a reason and I think there's a kind of toxicity and poison in our culture and I think a lot of that has to do with us, not respecting difference.

Paul Vato: That is so true. And speaking of race and maybe integration, how has The Second City evolved in that? I could only speak from my experience, I feel like I never experienced it because it wasn't like Second City was saying "no Latinos". There were no Latinos doing improv really, there was just a handful of us and that's why we put together Salsation, which then became Barrio Speedwagon in LA. We did our show Touched by an Anglo at Donny's Sky Box (Theater). I always feel when I speak to people like you, and from The Second City, I always wanna say, "thank you" because Salsation still exists today, 25 years later and The Second [00:15:00] City was a big part of it, you guys allowed us to do our show there and ply our craft. I never felt like I experienced any, " no", improv's not, it's only for white people that, but that's all who was doing it. We're the ones that need to come out of our shell and experience it, it wasn't in, in our wheelhouse.

Kelly Leonard: I think we have to acknowledge, it's complicated, and that there's nuance and we live in a world that isn't especially interested in nuance. I have learned so much during this period and things that I have some shame about in the past and other things that I think are that I'm proud of. If you read Something Wonderful Right Away, which is oral history of Second City, there is racist, clearly racist, viewpoints, spouted by alumni of the theater. That's true. Andrew Alexander, who took a lot of heat when the whole George Floyd thing happened and basically resigned and then sold the business. He started the first outreach program and put resources and money and personnel towards diversity efforts decades before anyone [00:16:00] else in the community was doing that. I think the problem was numbers of people on stage or not enough and there's a difference between diversity and equity that we didn't really understand as a company and I think we certainly started to learn it and we've had very diverse casts for years, but a lot of those people didn't have the support they needed and there were people who definitely had problems. All the people who were running the company essentially are gone and that happened again, George Floyd and COVID and we got sold to, to ZMC a private equity company who I like very much, actually that they've been hugely supportive. We have a great new alumni board, that's pretty diverse and they're gonna be artistic advisors to us and we're primarily led by women and people of color, right now and the old white guy, me, is here to support them. Let me give you an example. So some of the things that we heard that people were upset with was racist art that was on the walls of Second City and I, at first didn't understand what they were [00:17:00] talking about. Our then executive producer, John Carr and I said let's go down, let's do an art audit and let's walk around and see if we can spot what people are talking about. Paul. If you had been with us, you had been "no, like you can't". Do you remember the Main Stage you've got that Dan Castellaneta as Hitler, you have a photo of Hitler, like a guy playing Hitler, there's no context. If you're a Jewish person, you come in, you just see Hitler on the wall, oh, that's not good and then

Paul Vato: But. Okay, yeah.

Kelly Leonard: Anglo people in sombreros, so many people in turbans, and it's like white people. American, Indian headdress. It was like Mike Myers in dreads. It was this close to Blackface.

Paul Vato: I can picture all these because I think maybe like it was Jim Zulevic in a sombrero, I remember seeing that, but you're right, out of context, you walk in and you see, Dan Castellaneta as Hitler, I think instantly go oh, that's from, and I don't remember now anymore what show was from but I'm like, oh, that's an iconic show, from which show was it?

Kelly Leonard: I dunno, I can't remember, it was something in [00:18:00] the eighties.

Paul Vato: Jim Zulevic, I still clearly remember him, he's the one in the Mexican sombrero.

Kelly Leonard: Yep.

Paul Vato: And maybe a sarape. I don't know, maybe I need to be more woke because I would just remember seeing all those and just thinking that they're art, but instantly it tying them into The Second City, but I could see where somebody could walk in and go "what the fuck is this"?

Kelly Leonard: Look, I don't know necessarily that we need to apologize for, comedy that hasn't aged well, as long as WE age well. Like when Seinfeld says he can't tour colleges, I'm like, fucking, you know why don't try update your act then, and by the way, no one has a problem, Seinfeld doesn't do stuff that people get upset about.

The Chappelle thing just drives me crazy. Chappelle is so talented. Like, really? You want to go after trans folks, you think that they're the population that we need to be punching at? Like the suicide rate isn't enough to say you, maybe find a different target. It just doesn't even make any sense to me. You don't have to lose edge. It doesn't mean losing edge. My friend Dolly Chugh who's a social scientist says if we could think about, diversity, inclusion and [00:19:00] equity like we do our tech, we know our iPhone needs to be updated every few months, so does our language and our ideas. It's just updating. It's not surrendering.

Paul Vato: That is such a great analogy, it makes perfect sense. There are people out there that are like, oh, no one will ever get me to change. You're like that's, how can you not evolve?

Kelly Leonard: Why are you proud of that? We wanna be lifelong learners. Like you, you really think you figured it all out. Here's one thing, I'm 55 years old, had a great career happy marriage, kids, all that stuff, success by anyone's regard. I know nothing. What I have learned is that I know so little that the opportunity for me to learn more, to improve, to make new friends, all that stuff, it increases by the thousands, if I express myself with humility, when I walk into a room, when I enter a conversation, I learn so much more. I never want to be the smartest person in the room. If I'm that I'm not learning, and it's a drag. You can learn from anyone. People [00:20:00] have amazing stories and if you give them an opportunity to make space for those stories, your life will be better.

Paul Vato: A hundred percent. That was one of the things that I always try to incorporate. That's one of the things I learned from Del Close again, which was, everyone has a story to tell. Cause I remember we did our show that he directed which was Unauthorized Autobiography, that was one of the things was, everyone has a story to tell. And, Kelly, I try to do exactly what you're doing, I feel like you can learn from everyone, whether it was growing up in Chicago or then being in LA, and then now in Las Vegas, where you meet a cast of characters is the range from the homeless person to the executive casino owner, billionaire, and I try to learn what I can from everybody and be open to that, so thank you for sharing that. What happened to the artwork then, that you audited?

Kelly Leonard: Took it down and replaced it with less, less racist artwork. We took it down and it didn't need to be there, and again, I can't stress enough, how creating a space of inclusion does [00:21:00] not mean you're betraying the most important things about your work, because the most important things are everything you learn there, in the improv field, in terms of, making your partner look good, we still dare to offend, we're gonna cross the line and that's fine, as long as we know how to find our way back, cuz the line changes. This is the other thing, in our contemporary world, that doesn't like nuance, it also doesn't like context, the minute context and nuance, like they shift all the time. My wife is finishing up her second book it's on comedy theory and she talks about the elements of comedy, which include, pain and distance and recognition. When you're making comedy, it's like a mixing board. Sometimes you're dialing up the pain, sometimes you're dialing it down, after the events of Highland Park, do you really wanna make a bunch of mass shooting jokes, probably not that day. Maybe not in a week, three months, four, maybe, and then it's gonna be harder to do it in Chicago cuz of our proximity, our distance to Highland Park. Whereas in Vegas, that might not be a problem, though you've had mass shootings there.

All those elements [00:22:00] are at play and you've gotta constantly be aware because there's no five step, seven step, to anything. Anyone who's trying to sell you a book, that's "all you need" is ripping you off. The great thing about improvisation is that it's not a seven step view of the world. It's giving you tools and suggested practices for engaging other human beings and if you're constantly paying attention to that, like being fiercely in the moment, as I said, making your partner look good, all those things when to add something else to the mix or take something away and that's why I think in many ways, so many people who go through The Second City system have been so successful is not just cuz they learn that stuff on stage, they learned it off stage, it makes them better business people.

Paul Vato: It really does, a hundred percent does. That's something that I wanted to create, which is, this improv for executives and corporate people and business people. It was instrumental because, my first love is entrepreneurship, I don't think we called it that back then but I don't know if you know this, but when I was at The Second City [00:23:00]and studying improv, I started at Improv Olympic first, rest in peace. I interviewed Brandy Stillwell, and every time she says the iO or Improv Olympic, she always follows it up with rest in peace. She's got a great book out too, she's wonderful.

I owned a gourmet ice cream and coffee shop in the suburbs in Geneva, Illinois. It was Oberweis, it was an Oberweis Dairy of Geneva so that's why my journey to improv started a little bit later, I wanted to learn how to do standup and I wound up at the Improv Olympic trying to learn how to do standup and Charna was like, we don't teach standup, we teach improv. I'm like, I already paid you so... and then I fell in love with the artform, then of course, right after that discovered Second City, this would've been in like 97 and a year later, after I think getting kicked off of the team at iO cause I wasn't studying again, but I'd already studied with Del a couple times. I then had the idea of Salsation and we're like why doesn't Second City have, they've got RedCo GreenCo BlueCo why not BrownCo type of a thing. So we're like let's just do it ourselves. I feel like all these things that I learned in Second City definitely applied [00:24:00] to the business person then that I continue to be and when I sold everything and moved to LA and just sold cigars to support my acting habit, the power of "yes, and" is just so powerful and now that you've taken this whole scientific approach to it too that really fascinates me, Kelly, that is such amazing work that you're doing.

Kelly Leonard: So there's a new project that, that we're involved in which touches on everything you're talking about. So I had interviewed Suneel Gupta for the podcast. Suneel is an entrepreneur, the Rise App was his, his brother is Sanjay Gupta. This book he wrote called Backable, was amazing and I actually gave it to my wife to read and she loved it. Suneel calls me, this is like a few months after we did the podcast, and said he had been contacted by Northwestern where he is an alum the Farley School for Entrepreneurship and Innovation and they wanted him to do a class on Backable and he's I don't think I can do it alone, would you want to collaborate? My wife is a tenured professor of comedy and improvisation and a Northwestern grad so I put those two together and she just finished the class and it got amazing response because we were [00:25:00] bringing Suneel's ideas about entrepreneurship and improv practices to these kids who are maybe gonna be engineers and some wanna do startups. Literally, we have a call today and I was looking at all the feedback from the kids and they keep talking about how the status exercises, the storytelling exercise, the idea of "yes, and" as a way to get more ideas. This stuff resonated in a way that they were saying they've not experienced in any of their other classes. It was such a great experience to realize, oh no great practice for being a startup entrepreneur would be putting on a show, cause you have to do everything.

Paul Vato: Yes.

Kelly Leonard: You gotta get the people, you gotta market the thing, you gotta name the thing, you gotta do the thing, you gotta figure out how the money happens. It's oh my God, this is, that is classic preparation for startup culture.

Paul Vato: If you can put up a show and some are very successful, some are not you could definitely create a startup because that's exactly right. How do you get your audience? How do you market it to them? How do you get 'em in the [00:26:00] door? How do you get 'em to come back? How do you get them into it.

Kelly Leonard: It's all of it. It's hilarious. It's like it touches on every fundamental act of beginning a new business.

Paul Vato: That's it. And I've started a few, but I've also taken over a few, but I also feel like it's a fresh start. If there's anything that you ever need from me, or if I can get involved in any. I love this whole thing. And that's maybe why maybe it's just an excuse why I haven't put anything together because I feel like there's gotta be somebody that's way better at this already doing it, but if I could be involved in any way I would love to.

I'm a brand ambassador for a brand called Owwll, two Ws and two Ls, it's an app. I may have already sent you the information. I can't remember. We're looking for experts that can answer these questions and with the kids that you talked about that are the kids, and the college kids that are in the programs we've had a lot that call us it's part of their curriculum now to use the Owwll App to call us. Entrepreneurs or, in the different fields, different experts to ask them questions, they've integrated it into their curriculum. If you don't mind, I'll send you that information and you can [00:27:00] use "VATO" all capitals to sign up and you'll get 10 bucks to use on the app and then you can make calls too, cuz you know, you're an expert at what you do, but maybe...

Kelly Leonard: Not everything. There's the curse of knowledge is a term that gets used, which is one of the problems that you have when you have a domain expertise, is you tend to, see every nail with your hammer and not realize that you might need a screwdriver. I get asked to sit on a lot of panels and a lot of these sort of innovation conferences and they're like, what do you think is the number one stumbling block to innovation and I always say success. Cause once you have a success in an area, you tend to, quite rightly, want to do it again like that, cuz often you're successful again. That is a Law of Diminishing Returns. You can't find me the person who's doing it over and over again, that's actually good. They might be able to sell their, 20th murder, mystery book, it's not good and it's not innovative and they're not breaking new ground. That's what I would like to do. Like I don't, I wanna be done at 55. I wanna make making [00:28:00] discoveries. I want to have excitement and intrigue and all the stuff that everyone else you know gets to do when you're a young person. If you wanna be a lifelong learner, you really do have to exhibit these sort of improv practices every single day, because meaning is made in moments, right? I think we tend to think about meaning and purpose as these huge lofty things, cuz of course they're very important, but they are applied in how you treat the next person you talk to. I guarantee you, if you're in a bad mood, do something nice for someone, there's science behind that, there's plenty of science behind why we are wired to be connected to each other and to do nice things for each other.

Paul Vato: I never understood that growing up, which was like how can giving feel better than getting, but you're right, if you give, when you gift. How can I help you? How can I be of service, to you, type of a thing. It really does make you feel better.

Kelly Leonard: I'll actually say, we don't know each other super well. We known each other though a long time. And I think that's an orientation you've [00:29:00] always had. You always seem like you're someone who's trying to bump up other people and serve in that way and I think that's just a good thing and if we all do that, guess what? Life's so much better, it's so much better, then you don't have things like wars.

Paul Vato: Yes. Yes. At the beginning of 2022, I said to myself, this is the year of collaboration, because I feel like I've always been on my own and it's always been me, it's always been small business. My world just expanded by agreeing even doing this. I just have this thirst for knowledge and people that I find very interesting, such as yourself and your wife, Anne, which I would also love to talk about Anne a little bit, if you don't mind.

I've met this wonderful community here on Fireside, Clubhouse, social audio, I'm working on my travel show where I get to meet people. When I come to Chicago, I would love to hang out with you cuz you're right, we've known each other for close to 30 years maybe, but I've known of you, and maybe you've known of me, but we've never had a chance to do this, so thank you to social audio and Fireside and all that. Now, maybe the next step is in [00:30:00] our relationship, in our para social relationship, is that we get to maybe hang out and break bread together in Chicago, which is my travel show. I think Favreau had a dinner for six or something. So it's so funny, the way everything full circle, but I do owe your wife a big debt of gratitude, and this came up, I just interviewed Jim McCaffrey, who I believe he and I were maybe in level two. I think we figured it out, we were level two and I think Anne was our teacher there at Second City and she was wonderful. I've always had this weight issue and even back then and imagine how much more difficult when you own an Oberweis Dairy ice cream shop? When I bought it, I was 200 pounds when I sold it seven years later, I was 300 pounds. So I gained a hundred pounds in seven years because of this delicious ice cream and anyone that's from the Chicagoland area would instantly know what I'm talking about.

Apparently I was doing a keto diet. Anne was like, what are you doing? Cause I was eating pork rinds by the bag full, and she was like, those are not good for you, what are you doing? Apparently I said something to the effect. I've lost eight pounds. It [00:31:00] was something that came up with Jim McCaffery and I, so I wanted to thank your wife, Anne, I don't know if she's there or not or wants to come on.

Kelly Leonard: She at Second City teaching right now.

Paul Vato: She is. Okay. Wonderful. Do you wanna talk a little bit about your family? A little bit about Anne and what her role is, and maybe even how you guys met, was it at Second City?

Kelly Leonard: It was, Anne was running the box office when I got hired as a dishwasher, and then when I left and came back I was about to get married, not to her and my fiance didn't want me working so many nights. So Anne, I went to her and I'm like, Hey, do you have day box office shifts open? She knew that Joyce, who was running Second City liked me, and this was very crucial, Paul, if Joyce didn't like you, you were done at Second City and if she did like you the gifts were many, whether it's opera tickets or Cubs tickets or meals or whatever, she was very generous with the theater's money. Anne had the great idea of I would work Monday, Tuesday, Wednesday, Thursday during the day she would work during the evening, I'd just work one night, a week on Friday night. Anne was about to get married. Anne [00:32:00]Libra, my now wife of 25 years caught the bouquet at my first wedding. Yeah.

Paul Vato: Ooh, okay. I see how this works.

Kelly Leonard: And then I went to her wedding cuz we're all friends and then both of our marriages fell apart about a year and a half later and we started dating and very quickly realized that we had found the right one. I literally asked her to marry me at Steven Colbert's rehearsal dinner on the dance floor, and she said "yes".

Paul Vato: Wow. Yeah. What a great story, what a great romantic story. Maybe this is a hard question, so did you almost instantly regret getting married and did she maybe feel the same way?

Kelly Leonard: The first time?

Paul Vato: First time, yeah yeah yeah.

Kelly Leonard: The way I describe it is, when I met and fell in love with Anne it was like very similar to when I first got glasses and I realized, oh, there's definition on trees. It just changed everything. It's I, oh, I just wasn't seeing, I didn't know, I didn't know that, that you could be in a relationship with someone that you love, that wasn't acrimonious. I just like it wasn't [00:33:00] my experience up until then. And I don't know if, because I found the right person or who knows how these things work. I think we're highly compatible both intellectually in all the other ways. We have wonderful children. Our son, Nick is 24. He wants to be an actor but he's doing tech recruiting and he is very successful in that. We lost our daughter Nora when she was 17 to cancer, that was three years ago. And as horrible as that is and as difficult as that has been in our life we have weathered it as well as you can as a family and we always stuck together and we had each other's backs and her too. And we tried to make that year when she was sick as full of joy as we possibly could. It was interesting Anne was in class the other day and she has a student and she's God, I recognize that last name and it turns out it's the son of Nora's oncologist, who we loved and it didn't happen by accident, right? It was something that Jen who knows us well and recommended Anne and the class and this kid's terrific, too. He's really good. So it's like, [00:34:00]one of the things about going through that level of tragedy, there's a scientific concept called post-traumatic growth and the idea there is you can respond one of two ways basically when this stuff happens, you fall apart, you drink, you divorce, and that's very common or you try to do what we do. Which is, you can't hide from the reality, but you try to incorporate it, make her memory be something that you cherish and live your life as well as you can live it, and that's the thing we're trying to do, it takes work. Therapy's good, exercise has been huge. I was so outta shape, like when this went down and the year she was sick and one of the promises I made myself was. Gonna get up at five in the morning, every single morning, during the week and work out. And I did that and I lost weight and I gained muscle and I feel better about myself. It's not just that, we were we talking about this before, it's just living life with all the tools, cause shit's gonna happen, really bad shit's gonna happen and this the other thing, the year that she was ill, I kept a caring bridge journal and I was very open about everything [00:35:00] and the year after she died, I shared a lot of my grief journey and I had no idea up until then how many other people were dealing with tragedies because we don't tend to share those and I think we do that at our peril. I think when we are open and vulnerable and we share these things, it creates more meaning for us and meaning for others.

Paul Vato: It really does, and it really hit hard, Kelly. Thank you for sharing that and being so open and sharing. I remember when you guys were going through that and it was just, I was like, it's unfathomable to me. I don't even know what to do or say, or there's anything that somebody can do or say. I don't even remember if I reached out and because it's just I can't even relate to this.

Kelly Leonard: I think the key is, just be prepared to show up. If you're prepared to show up, some people might wanna talk, they might not want that but if you make yourself known that you're there, if they need them and so many people did that for us. We had a thriving community that was rooting her on, and that she felt. We had friends who pulled so many favors to get like [00:36:00] Hillary Clinton tweeted at her, Oprah Winfrey sent her a whole giant package of swag. The cast of Friends made videos and Grey's Anatomy, cuz that's what she was watching. And we're lucky cuz we're friends with Tina Faye and Stephen Colbert and Steve Carell and all these mega celebrities. It wasn't just that, it was also, school kids from across the world. That only happens if you choose to live openly, it's like a muscular kindness. It's it's hard, it's tough, this stuff's not easy, because you're really gonna be open, you're gonna get hurt again, but again, the opposite is being walled off and I don't think that's good.

Paul Vato: No not at all. So thank you to you and Anne and your family, teaching us, I think, how to live and maybe somebody who will get something from that. I remember that there was a hashtag what was the hashtag, and then maybe you also formed a, some kind of a charity in her name, or is there.

Kelly Leonard: It was #TeamNora still use it on occasion. What happened was both my kids went to Chicago Waldorf School, and they had moved into this new location and had this beat up side yard [00:37:00] and the school approached us and said, look, we're gonna turn this into a park and we wanna name it after Nora. You can go to the Waldorf School at Ashland and Foster in Chicago and Nora's Sun and Moon Garden is this amazing space with all these sort of hidden Easter Eggs with her name on it and wood and steel sculptures and things to climb on and people donated so much money to this thing, they raised millions of dollars in Nora's name. It's funny, it's literally on the drive where I go to therapy every Thursday. So there's something both sad and lovely about being able to look over there and know her memory is alive with all these children, who are doing what Waldorf calls risky play.

Paul Vato: Risky, for sure, cause if you're climbing or jumping or if you're outdoors, I guess that's maybe considered risky play.

Kelly Leonard: I love it. What a great metaphor for everything we've talked about. Like we started the conversation about play and we're coming to a close with it because it's like play involves risk and then in improv, you learn to take risks [00:38:00] and you learn that you're gonna fail, and you get back up. That's what you do.

Paul Vato: I believe it was, and please correct me if I'm wrong, but that there is no innovation in success, we need failure, in order to grow and we need to fall down and get back up and do it a different way and that's exactly the way business is. You're like that didn't work. Let's try it this way. But you're right. After a, while you rest on your laurels and your like, all right, I got this and it's easier and it's done, but then you're not growing you're not bringing it to that next level.

Kelly Leonard: Yep.

Paul Vato: Wonderful. Kelly, if there's anything I can ever do for you, please don't hesitate to reach out. I'll DM you about Owwll, but I'll also when your son's ready and he's looking and you probably have way more connections than I do. I have an agent in Chicago that she would love to, I'm sure, work with him, or at least look at his stuff, it's there. Just let me know. I can't wait to shake your hand, again and hang out and I hope maybe we can do this again, because we've mentioned so many names from our [00:39:00] past that are now, like you've mentioned mega celebrities.

Kelly Leonard: Yeah.

Paul Vato: I would love to to see whose life, you changed and what they would have to say about you. Maybe this is my whole podcast. I know that all these people, you know, Favreau was there at the beginning, maybe you met Vince Vaughn as well. I can't remember if he actually did Second City or not.

Kelly Leonard: No, he didn't do Second City, but he was around the scene.

Paul Vato: Yeah. Yeah. And Tina Faye and Rachel Dratch and Amy Pohler, all these brilliant comedic minds and improvisers.

Kelly Leonard: Yep.

Paul Vato: Kelly, thank you so much for taking time out of your very busy day and the work that you're doing is incredible and I'm glad that that I had the chance to sit here and chat with you for a bit.

Kelly Leonard: Okay. Thanks, Paul.

Paul Vato: Any final thoughts and then maybe where people can get ahold of you, if you don't mind and then I'll wrap it up.

Kelly Leonard: You can find me on LinkedIn, just type in my name and then on Twitter, I'm KLSecondCity and you'll have access to all my content there and just be nice to each other. How about that?

Paul Vato: That is beautiful and very well said. Folks, thank you guys so much for being here and spending a little bit of time with us. I'll have this podcast up soon and [00:40:00] that if I could ask you guys to please follow across our social media, if you go to, but also more importantly, if you're on Apple Podcast or Spotify, if you could give us a like, and maybe leave us a review there that would really help. So just folks, a round of applause for Mr. Kelly Leonard from the world, famous Chicago Second City institution, he's doing wonderful work. So thank you guys so much for being here. Thanks Kelly.

Kelly Leonard: Bye Paul. Take care

Paul Vato: Bye bye. Thank you.

Kelly Leonard

Executive Director of Learning and Applied Improvisation at Second City Works / Author / Podcast Host