Episode transcription 

Leigh Kessler:             If I think something is funny, it is, right? If, if I have an idea and I go, "Oh, that's funny." That's, you'd be good, but it is funny. My job is to figure out how do I communicate it to you guys in a way that you get it. Like if somebody ever tells you a story, right? And they think it's so funny and then at the end they're like, "Well you had to be there."

Audience:                  (laughs).

Leigh Kessler:             But no, I didn't have to be there (laughs). You had to do a much better job-

Audience:                  (laughs).

Leigh Kessler:             ... of putting me in the context of understanding why this was funny to you in the first place.

Alexander Kotler:             Have you ever delivered a presentation and felt like your message didn't connect. Perhaps you didn't know your audience. In today's episode we look at the funny side of marketing and business development with Leigh Kessler, a former comedian and now marketer who weaves together technology, brand and stories from the road to help our listeners find your voice. Our guest today is Leigh Kessler, VP of marketing communications at CharityEngine. He is an expert on brand and a former standup comedian, but we've asked him to sit down for a serious talk on tech and brand voice. Leigh.

Leigh Kessler:             Yes.

Alexander Kotler:             Good morning and welcome.

Leigh Kessler:             It's good to be here.

Alexander Kotler:             It's awesome. So give us a little bit of background on what you're doing now with CharityEngine.

Leigh Kessler:             Sure. Well, so CharityEngine is a ... I've been with charity and for about five years. We're a donor management software platform and basically a CRM for nonprofits. We work with very large nonprofits, wounded warrior project, Appalachian trail conservancy, some really amazing organizations and I love working with it. I love the idea of bringing technology and marketing and CRM technology to nonprofits because they often do it a little bit behind the rest of the world.

Alexander Kotler:             Let's talk briefly about the CRM, the technology that you offer and your role as VP of marketing communications with that platform.

Leigh Kessler:             So I would say what we try to do, and I think this connects to marketing, it connects to branding and voice over time, is that everybody talks about the customer journey, right? In our case and nonprofits, it's, it's the donor journey. And what you wanna do is identify over time how people are interacting with you, right? What did they like about you? Where are you relevant to them? Which of your messages are the ones that pertain? And you, you very often the mistake that all kinds of organizations make is using sideload to technology, right? You're focused on the front end experience, but you're not thinking about how that data is gonna transfer into a database that you can attribute data points too, that you can use in the future for segmentation.

Leigh Kessler:             So you can talk to people about the things that are relevant to them. I mean, I would say make the leap to stand up is you wanna talk about stuff that's personal to you and that you care about, but at the same time it has to be relevant to your audience. The beauty of today's technologies, you don't have to just broadcast. You can be very, uh, purposeful when you're talking to specific groups. The concept of AB testing is almost unnecessary because you know, this person, you know, the general idea of, do they let you know 53% of the people like cats versus 47 like dogs. So we're gonna give everybody cats. What if you knew the 53 who liked cats and the 47 to like dogs, then talk to them about the thing that matters. It's gotta be in your voice. It's gotta be relevant, but you still need to be able to pinpoint a message.

Alexander Kotler:             Woof.

Leigh Kessler:             (laughs).

Alexander Kotler:             So let's take a closer look, I suppose at the journey of your customer, of your donor. I think analogically we can have a better understanding of what you're talking about with the connection of frontend and backend.

Leigh Kessler:             Sure. So very often, even the CMS world, right? Content management or , whatever the purpose is that you're getting somebody to interact. Maybe you want them to make a donation or you want them to sign up for an event or you want them to do peer to peer fundraising or advocate for your organization. Reach out to their, their, their policy, peo- policy influencers. Very often they'll get different technology for each of those things. And those each have their own database. And so now you don't know if somebody who took an advocacy action is the same person who also attended your gala last year. If it's siloed data.

Leigh Kessler:             But if you can bring that together, you start to understand who's really engaged, who is a one time transaction and who is a long term prospect. I look at prospects are really just customers who haven't bought yet, right? And you have to treat them that way and constantly engage them, make them feel comfortable with who you are. And that's where having good brand voice and knowing who you are and makes them say your the ones we go to get that information. I like hearing what you have to say about this stuff.

Alexander Kotler:             We're gonna make that transition into brand voice in a second. But what I wanna focus on-

Leigh Kessler:             I'm I forcing it?

Alexander Kotler:             Yeah (laughing). This whole voice thing, just-

Leigh Kessler:             Sorry.

Alexander Kotler:             ... yes, yes, you have a very forceful voice.

Leigh Kessler:             Yeah.

Alexander Kotler:              I want to examine the power of insights. You're able to understand perhaps even after ex interactions with various touch points of your brand, when someone is gonna convert from being a prospect into a client and having a desiloed system.

Leigh Kessler:             You don't necessarily know it until you have it, right? I look at uh, I look at, I always look at as an example and now it's kinda common, but when it came out, it was a big deal was the Facebook 10 year anniversary. Remember the videos that came out Facebook 10 year anniversaries. And that was their big thing and that, you weren't logged into Facebook and they made a video of you, right? And here's the day you start it and , here is the, your, your first three pictures you posted. And here was the ... and over this time, here's what's gotten the most likes. Here's what got, you know, x, y, z. And they personalized it. But that was all data points, right? They just had a way to present the data points back to you that you were able to, they were able to show you that stuff, but all they were doing was looking at what's the number three picture?

Leigh Kessler:             You know, what, what got the most linked likes second most likes. When Mark Zuckerberg started Facebook, he wasn't thinking, "You know what I'm gonna do at the 10 year anniversary, what I'm gonna do is I'm going to make a video. Personalized video for everybody." But because they had the data they could. And the point is gathering data early on about every little thing somebody does gives you power down the road. , sort of the, the , the theory, the best time to plant a tree was 20 years ago. The next best time is today, right? The longer you wait and gathering data and understanding things, the longer it's gonna be till you can utilize it. So just making sure you have some thought as to what the points you wanna gather about people so that you can use that later on, even in ways you don't realize.

Leigh Kessler:             But you go to an ad agency, they'd say, "Oh, we'd love to do this and talk to these people. Can you pull up that group?" If you can't pull up that group, then you're wasting everybody's time. But if you can, then the ad agency says, "Oh, wow. Like we can actually do something pretty cool."

Alexander Kotler:             So then the next best time for us to start talking about brand voice might be now.

Leigh Kessler:             Good (laughs) 'cause I'm out of the other stuff.

Alexander Kotler:             That's great. And happy friendiversary by the way. So, what's really unique to me about your story, or perhaps even your perspective, is that before you were the VP of marketing communications, before everything else that you've done in your career, or perhaps even at the same time you were a standup comic, tell us a little bit about that.

Leigh Kessler:             Sure. So I yeah. All I ever wanted to be was a standup comic. I loved it as a kid. I fell in love with it as a kid. It was the thing that I just never stopped wanting to learn more about. If I could watch it, if I could read it, if it was on, I just wanted to understand it. So I'm as much of a student of it and have always been as much as somebody who loves to perform it and love to perform it. , I was very lucky that, uh, you know, a lot of people say, "Oh, I hear comedians are very dark and they're very disturbed people." And there are a lot just as there are in anything. But they're also very positive people too. They are people who just love this world of being in entertainment and making people laugh.

Leigh Kessler:            I was fortunate that I had parents who were very supportive of it and knew that that was something I really loved focusing on. My, the lesson I got from my father was a great one. My father loved what he did. My father was an intellectual property attorney. And so, and he loved his work. I mean, he truly, if, I know you guys have a lot of people in the legal world. If anybody knows Sterne, Kessler, Goldstein & Fox, my dad was at Kessler. So founding partner in a, in a firm, a boutique firm focused on this one thing. And his lesson to me was always just do whatever it is you want to wake up and do every day.

Leigh Kessler:             The, you know, one your best case scenario is you make a lot of money doing it. Worst case scenario is at least you're doing what you love every day. So that was a very important lesson for me in pursuing that as a career. So when I graduated from college, I studied psychology in American studies. It was always about understanding people, did radio to fit, you know, to be on mic and practice, that kind of thing. Moved out to LA, got started in stand up and work my way up. And stand up is merit based. I mean, you, you start with your first three minutes and you get to five and you get to six and seven, and that's not very good, but it's enough that maybe somebody brings you an emcee or you know, and you're the opening act for something.

Leigh Kessler:            Literally the first 10 minutes. And when you're an emcee, your job is to really just take the bullet, right? You've gotta turn the audience. Woody Allen has a great line, which is for comedy to work, the audience has to know that they're an audience. And so a stat- as the emcee, your job is to bring people's focus into, "Okay, we're doing a show now everybody so start paying attention."

Alexander Kotler:             Listen in everyone at home (laughing).

Leigh Kessler:             And then, so keep, kept on doing it, getting better. You get to middle and eventually I was headlining. So I was constantly learning. You gotta become a pro before you do anything right? The fundamental is you don't have the fundamentals, you've got nothing. You could have the most amazing six minutes of comedy ever tonight's show ready. But what's gonna happen when they book you into a casino and you've gotta do an hour and you don't have it. So you really have to learn how to do it. You have to learn how to do it under the worst cases. It's easy to go into a room that's hot and everybody's into it and the audience is great and you go up and it's just like perfect.

Leigh Kessler:             But what do you do when the audience isn't into it? When the emcee or the middle have not done it? There's an obnoxious person. The room is weird. The air conditioning is uncomfortable. How do you get that audience to pay attention and follow you and go with you? And that's really where professionalism in comedy is.  So that was my first five years was just learning how to do that. That I could be paid as a headliner to go on the road. I was more, I was fascinated with standup and that's what I, uh, as a, uh, a headline type act. I wanted to do an hour. I don't wanna just you stand up to get on TV or something. I really wanted to know what's it like to have people laugh at you for an entire hour. And that's an amazing thing, but not easy to get to.

Alexander Kotler:             I've had people laugh at me for an hour, but, uh, (laughing)-

Leigh Kessler:             It was called fledging.

Alexander Kotler:             What are some of the things that came out of it 'cause clearly you've transitioned away from comedy or at least you've integrated it into what you do now.

Leigh Kessler:             Sure. So what I learned was, you have to figure out who you are. You have to tell the audience who you are. , and that usually has to come out right away. The first 60 seconds or 90 seconds of a comedian getting on stage are really are what are going to determine whether this is going to go well. And if it doesn't go well by 90 seconds, you have about another 90 seconds to readjust so it does go well. After about three minutes of it wasn't going well it's an uphill battle. You can get them and there'll be okay, but it's not gonna be an easy ride.

Leigh Kessler:             So I, you, it's fascinating if you look at what a comedian ... what's happening when a comedian comes on stage, right? That are, they've gotta be comfortable, right? There, I always compare it to somebody. You get into a car with somebody who's a nervous driver and they get in and they turn the key and they're like play adjusting the fiddling with everything. They keep looking back, they're not ready to go. And you're sitting in the passenger's seat thinking, I'm not really comfortable with you as the driver here (laughing). You're never gonna enjoy the drive. But if you get in with somebody who just turns on the radio flux, the thing looks back, puts it in reverse and goes backwards. You're like, all right, I'm pretty sure I'm gonna enjoy this drive. So you need to be able to show people, "I'm pro, you're in my hands." That's a big part of it.

Leigh Kessler:             They need to ... if you're going to be talking about stuff for an hour, they need to know who you are. So that first three minutes of your act you have to make them laugh, but you also have to communicate who are you? I mean in my time I was talking about I'm Jewish, I'm suburban. I played sports. I'm not a tough guy. There was a lot of stuff that I put in the first three minutes so that for the rest of the show people understood who I was. If there's anything I've learned from the world of standup and continued on, it's the concept that specificity is universal. The more specific you are, the more everyone gets it. The more general you are. People can't really attach themselves to it 'cause they don't know what it means.

Leigh Kessler:             So that was one of the really amazing things I learned about standup was how you have your voice, be comfortable expressing who you are so that everything is within context and it makes sense. The other side of it was, and that's like road comedy as I talked about you doing an hour. Then here in the city when you're trying to be in TV or whatever you're doing showcase clubs. Think of something like Last Comic Standing where you're watching people do three minutes apiece. There's certain comics, right? They're so different visually they come out, they seem different. But I'm an, I'm a white Jewish guy (laughs). Heterosexual guy. There's, we're a dime a dozen.

Leigh Kessler:             So how do I differentiate myself then and again, it's being specific and explaining to people who I am and it's what, it's the clothes I'm wearing. It's my voice, it's my smile, it's my hair cut. All of that leads to them understanding who I am. That's the only way to get them. If they don't understand who you are, they're never gonna be able to attach themselves to you.

Alexander Kotler:             There's an interesting clip that I saw a view less from your standup, but more from your presentation where you use the phrase you had to be there to get it right.

Leigh Kessler:             So that's the idea. When you tell somebody something funny sto- somebody tells a funny story, people don't laugh and they say, "Oh, well you had to be there." No (laughs) you didn't have to be there. You had to do a better job of communicating. What was funny about in the first place. Put the person in that context so they feel what it was that you saw funny in the first place. And that's where you get to date. I mean, going back to the beginning of the conversation about data, like you gotta workshop things. I may have an idea. I know it's funny.

Leigh Kessler:             It's gonna take me a number of times before I've clearly communicated to the audience what it was that I thought was funny in the first place and that's getting it wrong. And that's bombing and not getting the joke right. But every comic records every set. And you go back and listen and you hear what, what was good, what did we, why did it work this time and not last night? By recording it, by getting data, you can analyze what works about it and what doesn't. But you need to know that people aren't going to get who you are necessarily right away, even though you think you know, you have to communicate and explain it and be specific.

Alexander Kotler:             One of the things that's really fascinates me and I really liked how you're tying all of this together in some ways that's supposed to be my job, so I'm glad you can have my job and do it. However-

Leigh Kessler:             I'm a genius-

Alexander Kotler:             (laughs).

Leigh Kessler:             And you have to deal with that.

Alexander Kotler:             I'll be hble. Nevertheless, putting it in a sales and marketing context, the variable is you don't know how your audience is going to respond. You may know because you're in a certain city, you have a little bit of information, you do your research, you're still going to go into a sale and know a little bit but not necessarily know enough. So how beyond the specificity, the three minutes of time that you have to deliver your first joke, can you use what information you have and come in to close an opportunity?

Leigh Kessler:             I think it's starts with, and it does go back to that first three minutes. You have to show them you're gonna take care of them. And you have to show the audience that I'm the professional, you're in good hands. And even in marketing and your website, your website can't be confusing and make people guess at what you would be able to do for them. It has to address specifically that you're gonna do this and here's how you do, here's how you're going to solve their problem. They came to it, you're showing you get it and then , and then you, they show. Once you've engaged them there and kind of convert it to the sales concept is that now once they trust you, they'll open up to you and they'll have a conversation and a dialogue, right?

Leigh Kessler:             So they'll explain, okay, now we talked about that. What's your specific need that I maybe don't know about? But they trust you. They see who you are and they believe in you. The same thing would be the case, uh, uh, of being a comedian is that I've got you and you believe me. If something's off or there's something I don't know, by this point I've gained the trust of the audience that I can reference the fact that that didn't work. And we can talk about why it didn't work. And maybe there's genius in that moment. And I'm hilarious in that interplay, that ad libbed interplay. That's also, that's part of the product I'm selling. But I really think it starts with you, you asserting to them that you're the pro and they'll give you leeway to later.

Leigh Kessler:             A quick story. I was in Tulsa, Oklahoma where I was doing Wednesday to Saturday. I think Tulsa Comedy Club was ago. And I'll never forget. I, I had a bit about the always worked. And I would do the road. I would do cruises. This bit always worked. It was about Chinese food. And I talked about duck sauce and I would, and every night when I do this act, this joke, it, it didn't go anywhere. Like it literally would fall flat. And I was like, get in my head, I'm thinking, I don't get why this doesn't work. On the last night, the emcee, now I've done five shows, this is the sixth show. I brought it up to him and said, you know, it's funny that joke always works and it's not.

Leigh Kessler:             He said, you know, I meant to say something to you. Here in Oklahoma, like I know what you mean 'cause I used to live on the east coast with duck sauces. But here we don't have takeout Chinese, right? We don't have Chinese restaurants. We have like Chinese buffets. So what that duck sauce is usually in like that big squirt ketchup bottle and it's called orange sauce. They don't know what you're talking about. And that to me was an incredible lesson of I've got this right every time. But I didn't know that fact, but it didn't kill the show because by that point in the act, they liked me and they were good with me. And if that joke didn't work, that joke didn't work. You know what I mean? If that had been my opener and it fell flat, they'd be like, I, I am confused and I don't ... like the nervous driver. I don't trust this guy.

Alexander Kotler:             You should always come with a surefire joke and orange sauce right at the start-

Leigh Kessler:             (laughs).

Alexander Kotler:             ... ready to go.

Leigh Kessler:             Well, but you do, you start with the stuff that you know is gonna work. I mean, you gotta have that opening five minutes that, you know, it doesn't matter what audience I'm in front of. It is concise. It is good. It says who I am. It works every time and I believe it. That's as much as anything that I need to know even if I do that and I don't get a laugh somewhere in that opening, I know I'll get it at other places in this bit, in this five minutes, because I know that that works. And you want the clothes to be the same thing in the middle is maybe where you're playing around.

Alexander Kotler:             That's a beautiful synopsis. If I know who I am, I clearly and concisely can articulate that immediately. We can establish a rapport and trust with our audience. They're going to know who I am and what it is that I'm offering. If you come with insights. If you come knowing your audience, which in some cases you're able to, you can actually share the relevant pieces of information that's going to resonate with them so they'll know who you are and they'll appreciate that you know what they want.

Leigh Kessler:            And the little things, they're comics that maybe they always have a joke about going to a grocery store before they go on stage, they'll ask the emcee, like what's the name of like you're all night grocery store. And that way when they do the joke they'll say, I was at Giant, I was at all these. Just because the, it's that little thing that personalizes and says to the audience, "Oh this guy kind of knows us." He's why I ... he's not just selling, selling, selling, he's talking. And that is a big thing to be able to do.

Alexander Kotler:             So it's specificity plus relevance and personalization, which makes it resonate with the people that are there. This guy is, this guy knows what my grocery store is.

Leigh Kessler:             Right. And, and the other thing is you can't just sell, sell, sell. And I'd say that's another aspect of marketing. Sometimes when a comedian, if things aren't going well, and they've kind of, they don't have the audience, the audience isn't buying what they're selling. They'll stop and they'll do crowd work. And the reason you do crowd work is to say, you know, pull it back in, get in the moment with people again and create something about them you know, "Hey, where are you from? Are you guys on a date? Uh, you know, you have kids?"

Leigh Kessler:             And now you're talking with the audience. Hopefully you're good comedian and you can make that funny. There's little things you do there. , or you can find a way to squeak in a joke that's relevant to what they just said that you already have. And now you can get back on track. But what you've done is you've told the, you've made it about you and the audience engaging and you stop selling and you made it about the two of you having a good time. You, the comedian and the audience.

Leigh Kessler:             And the same on a website. I'm always amazed when I look at websites and they'll have that, that call to action. So clear, but then they're not asking, "What are you here for? You know, what, what are you looking for? What can we help you with?" , even like a search index capability that says that you type in, I'm looking for this and then you show up a Google type results of those things to help people find it. You need to sometimes say, "hey, we've got a lot, what do you need and let's help you with your needs." Let's make it about you versus look how great I am, look how great I am. Look how funny I am, look at how funny I am.

Alexander Kotler:             What's fascinating to me, was the first thing that came to my mind when you started talking about crowd work is we've all given sales pitches and presentations that we can see we're losing our audience. Someone is checking his phone, someone is shuffling through papers or looking at the wall. And it seems like the crowd work technique might be something that people can use within the context of a pitch to bring that audience back in. To make sure that they can realign and get them to focus and pay attention and make sure you're talking to the points that are going to actually interest them.

Leigh Kessler:             Right, exactly right. And sympathy, you know. So let me ask you something. How many clients would you say you guys have? How many clients would you say you're trying to get this year? How ma- right? Just ask them the question, stop selling it and make it a dialogue and it gets you a chance to regive yourself energy. The other side of that, by the way, is when you feel like you've lost the audience from a sales perspective. And that I've learned as a comedian is not to take it personally and not to judge how it's going based on their reaction.

Leigh Kessler:             Sometimes you've gotta look at the circumstances and realize, no, they're with you. It may not be high energy and then there'll be smiling and like, you know, pouncing on every word. But you've gotta be able to be confident in yourself, not get dry mouth. You know, always, I always have water, always have water. That's number one thing in case you get dry mouth. , because when you get nervous, that's the first thing that happens. But to just comfortably be like, I know what I'm doing here. I know why I'm here and I truly believe I have a solution for you. That's what a comedian is doing is I'm, I know I'm here. I'm gonna make you laugh and I'm good at this. Trust me. Come along with me and you'll enjoy it.

Alexander Kotler:             I haven't seen you get dry mouth yet. I see you have water there, you haven't taken a sip. I haven't asked you a question that makes me nervous.

Leigh Kessler:             Oh, you'll know when you do (laughing).

Alexander Kotler:             You actually speak on brand voice and you can be booked. So I want to hear a little bit more about this program-

Leigh Kessler:             Sure.

Alexander Kotler:             ... ask you how can people learn more about how to book you?

Leigh Kessler:             Sure. Well, it goes back to, this is something that came out of when I first ... what got me out of standup and into the, the world of branding and marketing was originally I had created, I did a lot of TV and I was doing the road and that's how I was making my money. And I'd come up with a TV show idea, shot a pilot, I wanted to, I was pitching it to networks. I had a lot of connections because I was doing well, so people would meet with me. But I never wanted to miss a meeting so I didn't want to be on the road all the time. So I wanted to stay in the city. That led to working at an ad. I got a job as a copywriter at ad agency. So I could be local and be able to have meetings.

Leigh Kessler:           That being the copywriter was interesting. But what really excited me about that work was I would spend a lot of time with the brand strategists and that to me was stand up. What they were doing was exactly what comics do, which is finding what are those unique insights, what are the things about what we're selling? For example, we were in the cultural marketing, a client was Philadelphia Museum of Art. What is unique about the Philadelphia Museum of Art that, that it's not the words you write, it's that insight about why people would want to go in the first place. And I just looked at that and was like, it's just like stand up, right? It's, why are you unique? Why are you special?

Leigh Kessler:             And then I went to other agencies and then I got into market research. It was always trying to figure out why are you unique? Why are you special? And how do we get to that? I would do focus groups. Focus groups you're listening for, not for people to tell you what you need to know, but you're listening for what you don't know. What don't you realize about the product you're doing a focus group for? Or the message that says, "Oh, wow, that's really interesting." And all that time I was like, this is stand up. It's the same exact tools. So as I progressed in my career and did more stuff, I was always like, one day I'm gonna do something with this.

Leigh Kessler:            I was asked to speak somewhere. I came up with this. It went very well. And from that it turned into being booked at places, and front of branders or marketers or , you know, entrepreneurs, salespeople. Anybody who's ever been tasked with standing in front of somebody and they say, you have five minutes to tell us why it's you. You've gotta know why it's you. And you gotta know why you're different. And you've gotta present it in an authentic way. And I thought this would be a really interesting way for people to look at that, get that message. There's a lot of people talk about Zig Ziglar, right? There's a lot of people talking about how to do sales. You could book them, but would it be interesting if you heard it in the context of standup?

Leigh Kessler:             Because everybody loves to talk about standup. People are fascinated with it. That's where this presentation came into and it's been, it's been a fun thing to do. I love watching the audience react to it and say, you know, laugh at it, have fun with it, and look at comedy in an academic way, which I did, as I said, being a kid. So that's kind of where I am. You can book it at standupspeaker.com. Check out the website and you'll see all our cool stuff.

Alexander Kotler:             Leigh Kessler, VP of marketing communications at CharityEngine. And you can find at standupspeaker.com. Thanks so much for joining us at RubyLaw Insights.

Leigh Kessler:             Thanks for having me.

Voiceover:                 RubyLaw Insights is recorded at studio 55 and it's hosted by Alexander Kotler. For more insights and detailing RubyLaw and enterprise software developed by Ruby's team tech visit rubyapps.com until next time, have an awesome everyday.