EP017: Laughing Your Way to Better Sales with Jon Selig

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Jon: Fast forward to today, I performed for about 12 years. I did everything from dive bars to clubs to little festivals. But the very first time I was on stage, I saw the parallels between sales and stand up. I’m like, “oh, this is like presenting to an executive team, except they’re slightly drunker and the budget’s already been spent to come into the club and the alcohol.”

Joel: My name is Joel and I’m a recovering nerd. I’ve spent the last 25 years bouncing between creative jobs and technical teams. I worked at places like Nickelodeon to NASA and a few other places that started with different letters.

I was one of the first couple hundred people podcasting back in the early aughts until I accidentally became an IT analyst. Thankfully, someone in the government said, “Hey, you’re a nerd that talks good.” And that spun me off into the world of startups, branding, and marketing, for the same sort of researchers and startup founders that I used to hang out with. 

Today, I help technical people learn how to get noticed, get remembered, and get results.

On Nerds That Talk Good, I want to help you do the same. I talk with some of the greatest technical communicators, facilitators, and thinkers that I know who are behind the big brands and the tech talk that just works. 

My guest today took an unconventional route from enterprise sales to stand up comedy, then found a way to bridge the two. And after 12 years of selling enterprise resource planning, business intelligence, and professional services for companies like Oracle, Jon Selig made a hard pivot into stand up comedy, chasing his dream of never selling tech again, but we’re going to talk about how all that worked out.

Along the way, he discovered that sales and comedy share more than just tough crowds. He’s now the founder, creator, and chief of stuff at Comedy Writing for Revenue Teams. He helps Sales professionals sharpen their messaging, connect with their audiences, and inject a little humor into the pitch. He’s worked with teams from Broadcom, Citrix, Microsoft, and more, proving that comedy isn’t just entertainment, it’s a powerful communication tool.

So, Jon, thank you so much for joining. I have been wanting to have you on for a good while now.

Jon: Thank you for having me and I’m delighted to help you fulfill your dreams of having me on your podcast.

Joel: All right, we can stop right there then. We’ve done it. So, so we met before the cyber marketing conference that we both spoke at, and I was very interested in the session that you did, which I want to dig into and what you do as a comedy writer for sales and revenue. But I want to open up just first with the nerd origin story.

I alluded to a little bit, but you tell it much better than I do. So why don’t you grace us with that that hero’s journey?

Jon: Yeah, I don’t know if I’m a hero, but I’ll tell you the journey. So I look at like so many so many who didn’t know what the hell they wanted with their lives. I ended up in sales and I ended up at a very good sales school. I ended up at Oracle. I worked in consulting and I’d worked in banking a little bit, but like, and at a at a dot com.

Which dates me a little bit, but should give some people an idea of my path. And, it was a time, it was like the dot com bust. And, there was a lot of uncertainty, and if you didn’t have really hard skills, it was like, well, what do you do? And I ended up getting a job at Oracle which I had heard of, I didn’t really understand what they did.

But it was, they were hiring people to do something called business development consulting which sounded like really, like, like prestigious, like, oh, I can be a consultant to help Oracle develop their business. Not fully understanding how large they were. And when I sort of went to the interview, They broke it to you that despite what the job description said, this is a cold calling role.

And I got to make 40 dials a day to help uncover new opportunities for the enterprise applications team. And I almost walked out of what was a group interview. There was like 40 people there applying for like 10 roles or something like that. A lot of MBA types who were in a similar boat to me.

Not knowing what’s next. And I ended up getting the job more or less the next day. Like I, I went through a kind of their process. I had to present to the guy who ended up being my manager and we had to prepare a presentation in advance. They told us that before I even interviewed, I delivered this presentation and I just said to this, skinny guy from Dallas sitting in sitting in the room, the only guy in the room.

I delivered my presentation on my friend’s business and I said, “do you have any questions?” He says, “dude, I don’t know what you just presented, but you’re going to fit in fine around here.” And so I apologize to anybody who doesn’t like my Southern accent or my Texas accent, but I got the job and it was really a fantastic experience because I didn’t really understand what sales was. I didn’t understand, I didn’t understand a lot of things and it was a really great education, ending up in sales at Oracle.
 

I moved from a cold calling role to a inside sales role. And really the thing that flicked a switch on for me that this is a career for me is, forget being a salesperson, your job is to be a business consultant to help companies solve very specific business problems. Oracle solves so many, at least their business applications do.

And their technical products like Database do as well. But you’re not trying to like close business, even though that’s exactly what you’re trying to do. You’re trying to help them solve problems. And if we can help them solve a problem, we continue having a conversation. And if we aren’t able to, we tell them, “listen, I don’t think we can help you, but maybe here’s a vendor who can.”

So ended up selling for Oracle for two and a half years. Ended up joining an Oracle partner and I spent another six and a half years there and helping them grow their grow their practice from, I don’t know, we were like six or eight full time people when I started; about 35 people when I left and doing everything from cold calling, inside sales to field sales for these guys being a full cycle sales rep and hit a wall at that point where, for, I won’t get into the reasons, but I started to question, like, is this what I want to do with the rest of my life? Talking to customers about things that like, the business issues I understand, but we also started selling things like business intelligence projects and the technical architecture behind data warehousing and stuff like that. And that was a world I didn’t really feel super comfortable in. I started to ask CIOs, like, “what ETL tool are you using?”

And I realized, like, not only do I really not understand what ETL is, I’m not even sure I know how to spell it. And, the letters are pretty, the letters are pretty clearly right there. Or the spelling is right there. And so, I was looking to make some, shake up my career a little bit.

And I decided what better way to shake up your career than make zero money whatsoever. So I pursued stand up comedy, but not to become a full time comedian, just to immerse myself in the new world, learn some new skills, meet some different kinds of people, and maybe change the trajectory of my career.

Fast forward to today, I performed for about 12 years. I did everything from dive bars to clubs to little festivals and even produced some overseas fundraiser comedy tours. But the very first time I was on stage, I saw the parallels between sales and stand up. I’m like, oh, this is like presenting to an executive team, except they’re slightly drunker and the budget’s already been spent to come into the club and the alcohol.

And so I started to really think about like my sales background and marketing background, even to some degree, to understand like, how can I connect with these people who’ve come out for a night of entertainment? I really ended up watching a lot of the people the other performers on the open mics that I was on.

And I’d learn a lot by watching them and how they weren’t connecting with audiences. And learning how to read the room. I was a little bit lucky. I started a bit of an older age. A lot of comedians who start, they’re young and they only know what they know. They don’t know how to relate to a group of older people who might be in the room that night. So I started to, again, really compartmentalize or document those parallels between sales and standup. And what are, why are comedians not getting better? Why are they failing To connect with audiences. Why are they failing to elicit emotional reactions? And eventually I said, you know what, I could do a couple of things with my sales and my comedy backgrounds.

I can deliver, I can help salespeople become better communicators. I can help salespeople better understand their buyers, their audiences. I can help salespeople understand why their audiences care about them all by using the comedy writing process. To help them achieve that and if I can help them get a little funnier, a little more personable and use humor to connect even better.

I will say that’s, it’s a bit of a revisionist history. When I started, it was what you described. Like I helped sell salespeople and marketers use humor to, to connect, to make prospects laugh around real problems that they solve. And and start more conversations. But over time, it’s evolved based on feedback from my clients is that the process of writing humor is powerful sales and marketing enablement.

And, it doesn’t matter if we write a great joke or not just putting sellers and marketers through the process of what comedians go through to craft material is a great way for them to internalize who their audience is and why they should care about them. So I hope that, that was a really long winded answer to a very simple question.

Joel: No, that was absolutely perfect. It wasn’t a tight five. It was a tight eight, but that’s okay. 

Jon: I would say a rambling ten. 

Joel: I was really excited to sit in on your your session, which was really fun where you started out basically saying, “look, we’re not going to walk out of here being hilarious.

And the objective is not to to, to knock people out with a great joke, but it’s to understand human inclination to connect,” I think is really what it comes down to, which is your comedy process. But you have some great, lines. I was I was reviewing some of the videos on your website and I will link to that in the show notes.

But you said your opening line that always works, that always kills, you get sick of it yourself. And I think that is one of the major problems that technical communicators have is we always want to say something different. But there is value in doing the work up front, having something written down that you know works.

And it might be the hundredth time you’ve said it, but it might be the first or second time an audience has heard it. How do you know when you have something that works? When you’re Developing.

Jon: so I’m going to answer this question by let’s get a couple of things on the table first, and there’s a very good chance I’m going to forget your original question, because I have the memory of an elephant, a dead one. Look, stand up comedians, people think they’re making it up as they go along, but that’s not what they’re doing.

That’s improv. Improv comedy is about creating unrecreatable, unscripted moments. Comedians, their job is to make it look improvised and unscripted, but it’s actually quite carefully scripted, honed, iterated, crafted, whatever words you want to throw in there. And they’re trying to create repeatable moments, repeatable reactions from audiences.

So look, if you’re a technical resource and you’re trying to connect with your audience, you got to figure out what’s going to flick on their emotional switches. Like, why are we on this call today? So let’s say you’re you’re demoing a solution. They’re all on the call because they’re probably on the call because it’s been determined that you could help them solve a problem.

Well, how does that problem affect them? How does it affect their technical objectives, their business objectives? How does it affect their emotions? And once you understand those truths, you’re in a position to find a a creative way of communicating that and hopefully, flicking on that emotional switch that makes them go, “that’s funny because it’s true.”

So I like to call it like roasting your prospect pain, like what are they struggling with and why does it suck for them? And getting specific around the suck. And once you have that line, it shouldn’t be boring because making people laugh is a drug. There’s a reason why people get addicted to doing stand up comedy, myself included.

It’s because, we like that validation. I never did it for the attention. Validation I’m on board with. Like, I wanted to know that people liked my weird ideas and my thoughts and that they saw the same things I did. That was very empowering. And for anyone who’s delivering a demo or having a technical discussion, if you could make your prospect or your audience laugh right up top around a powerful truth that they’re struggling with, they’re going to view you as a credible, trusted subject matter expert, and they’re going to like you.

And they are going to give you all their attention. They’re going to be all in. So I don’t think that you should get bored by delivering the same bit of humor that works again, that works every call you should embrace that and use that as your superpower.

Joel: Yeah, it’s part of my personal model. I borrowed from Aristotle. You have to make them like you before they can understand you and build trust. And it’s that sandwich of connecting and building trust that the technicals are almost well, they’re, it’s second, but they come in third, almost, as a priority.

I’d love to not recap your full workshop, but I would love to talk through how you see a joke. How you see, why do people laugh? I’ve recently re watched your replay that they posted up.

But now that I’ve sat and thought through it, I’m like, these are frameworks and truths that I don’t see a lot of people doing when they’re developing messaging. And maybe that’s because I don’t come from the sales side. I come more from the marketing side. But can you recap a little bit of your of the process, not to give everything away?

Jon: I’ve learned I can give it away. And then like, I don’t know if everyone knows how to do it. Cause I think some people, after a certain point in life where we’re wired a certain way and. Not always able to take what’s, like, I can give everyone the instructions. Can they create a great joke?

There’s always a, there’s always someone in my workshops who like, they’re like, “Oh my God.” And they see the dots. They’re able to connect those dots and make connections between everything I’m saying and like they have that that something in them where they watch a lot of comedy and they’re able to see how it all unfolds and create something from it all.

But let’s also, let’s again let’s define a joke. So a lot of people when I use the word jokes, they think I’m talking about like, something that their uncle tells the Thanksgiving table, this long winded story about, various clergymen entering establishments of ill repute and saying offensive things to each other.

A long winded story. That’s not what I mean by joke. It’s not an inaccurate definition, but to me, like stand up comedy, the art form has evolved. It’s a little more long winded these days and audiences have more patience. But a while ago, Your objective was to make audiences laugh three times in a minute. And to do that, you needed to develop like short, punchy, one or two liners that offered some relevance to the audience, and then subverted their expectations of what they thought you were going to say. So a joke to me is like a one or two liner that, that, shines a light on something relatable and relevant and usually painful. 

Joel: Hmm. 

Jon: or for the listener or the audience, it subverts those expectations and it gets that emotional reaction.

It gets people going. “That’s funny ’cause it’s true.” Or “that’s absurd. That’s just funny. Cause it’s exaggerated.” And like there’s lots of jokes or formulas at the end of the day, like you said they’re structures. And if people learn how they work, Shouldn’t be too hard for someone with a decent sense of humor to try and assemble them.

There’s a bit of, yeah, it’s a bit of the magic eye puzzle. I forget if I used that. Forget if I said that when I, when you saw me speak, but, you can capture all the subject matter on paper and words and phrases, and then you got to like stare at it for a while. And like the good stuff will pop out and you’ll see it.

You’ll see that’s the joke. And then it’s a matter of just wording it and structuring it a certain way. So short, quick humor has this ability to capture attention spans and demonstrate that relevance. Again, flick on emotional switches and get people to like you and trust you within 5 to 10 seconds.

Does that answer the question? Because I knew I’d forget the question

Joel: Yeah, absolutely. The formulaic, setting up an expectation and subverting it, but doing it in a way that’s authentic and true, maybe a little bit exaggerated or unexpected. And I think there are people who do it well, unprompted or if things just come out, but you have to have your ears open for it.

Several years ago, I was at the RSA conference, I was saying basically, all of these companies look and sound the same. All of these companies look and sound the same. And I got little head nods. At the moment I said, “all these companies look, sound, and smell the same.”

I got chuckles. And my ears went up and I realized what I was doing there was throwing in that absurdity, that little unexpected, you know, they, they think they know what they’re, what’s coming. I, I would call that almost a pattern interrupt. Um, But what are some of the other tactics or formulas? Do you have a grand theory of the the atomic elements of humor?

Jon: Grand Theory of the Atom? No, I don’t. And if I did, it wouldn’t be any different than what’s out there. I’m not claiming to reinvent any wheels. I think like a good, like a simple formula for people to process is comparing two very different things. We say X is like Y because, and then give them the because.

So I’ll give a perfect example. There’s a joke structure called the rule of threes. Although the one I’m going to share, the joke I’m going to share, it’s a, it follows a rule of three, but it’s also a little more like an analogy, I guess is the best way to put it. So there’s two kinds of rule of three.

The first one you offer a bit of insight or a statement of some kind that’s relevant to the audience and like, Oh that’s relevant to me. I’m going to listen. And then it’s the punchline comes in a list form. And the first two you list three, three things. And that, that, that’s three qualities or characteristics.

associated with what you’re trying to say. And the first two are in line with what you’re expecting or what the listener is expecting. And the third comes out of left field. 
 

And the other one is basically where there’s, you’re comparing two different things, and you list three things that they have in common. The last one being, the funniest one, or the one that gets the big laugh. So I worked with a company called Neo4j, they develop graph database technology, and that is the database technology that’s behind the algorithms that feed us all these dumb videos that we know. On, on apps that we hate, like TikTok, Instagram, and Facebook ,and YouTube. And it replaces the need to use a relational database, which is like the old school databases that serve up all kinds of information.

When we search and query online. And so these guys were trying to write jokes for software architects. At financial institutions who were trying to like find fraud detection patterns. Like that was the use case for what we were writing jokes for. So the joke that they wrote, I didn’t write this is “your relational database management system is like Darth Vader, terrible at relationships, big in the seventies and easily corrupted.” So that’s like, we listed three things and we’re just comparing, we’re listing, we’re comparing two different things and we listed three things they have in common and the last one should be the one that’s going to get the biggest laugh.

Joel: I think in the workshop when you had us do that, the one that I came up in, in my head and I’ll of course butcher it, is if we don’t do x, our sales pipeline will be like a toilet slow backed up and the cold colder than Wisconsin in winter or something like that.

I don’t remember what it was. And but the, I think that. The point is, you’re looking, if you have this idea that you’re going to fill this you’re going to go after a particular formula or you’re going to use a particular framework, that can sometimes be limiting because you might stop thinking of things after three.

So I’d love to, to talk about the cutting room floor and how you get people to. pull out more and bring more. One of the challenges I have with my clients is I, ask them their Big Idea and they’ve got a preconceived notion and they get stuck on that. And it isn’t until we break their brain or soften their brain a little bit that they share more.

And I think, like you said, comedy is about going that extra mile and going to the absurd. When you’re working with sales folks or technical folks you have any tips and tricks for how do you get them to step out of their comfort zone a little bit? 

Jon: Well, look, you can’t write a joke, unless you unpack the reality of a situation and document it. So the first step is to answer a lot of questions and all of, look, I like to help my clients write jokes, not just about the problems they solve, but the implications or impacts of not

them. So very often I’ll work with sales teams and I’ll say, Hey, “you solve for problem X. What happens to your target persona if they don’t solve for target for problem X?” They’re going to waste time and money is the most common answer I get. And I’m like, bleep bleeper. Sorry. I’m just, I’m self censoring myself here because I’m going to call them a nasty name.

Every business and technical problem on the planet costs them time and money. You need to be really specific about what those root causes of the wastages of time and money are. You need to show them you understand their world inside out and document as much of that as you can. Think of it as a bit of a chain reaction and document all the ripple effects on how it’s impacting other stakeholders.

Don’t even think about money and time. Just get specific around, so for example, if you have poor podcasting software, you’re gonna have a lot of technical glitches. You’re gonna have to spend a lot of time in edits. You’re gonna have to maybe reschedule your guest because the podcast didn’t come out correctly.

All that wastes time and all that wastes money. But by mentioning this to you, like I’m showing you, I understand, well, you’re a podcast host and you need the right tool.

Joel: Yeah, and that’s where the narrative comes in because you’re putting them in a situation as opposed to presenting a an antiseptic outcome. And I think as technicals, we want to boil everything down to antiseptic outcomes. And so you almost, have to do “yes and.” The so what?

Jon: Yes. and. 

Joel: I’d love to know some of your maybe without naming clients, but some of the the tactics that you’ve brought to clients that have worked, that you’ve been surprised about, or how you maybe were challenged with particular industries, because, you came out of software and services and consulting. But now you’re in front of companies, like Neo4j and you have to learn about their products and their technology to a certain extent.

What’s been one of the most exciting challenges or teams that you’ve worked with? 

Jon: What I love about what I do is coming from a consulting background and selling ERP software and business intelligence, you’re, again, you’re still a consultant. It’s a bit of a different vehicle you’re taking to deliver consulting. It’s through software sales. And you’re learning about different industries and what the key KPIs are and what they’re trying to achieve.

You also learn how to boil things down to simplicity a little bit better through this process, because the more complex you get, the more bigger chance your message is going to get lost. So I’ve worked with a couple of companies who I’ve delivered some interesting results for. One is a company called PowerChord and they, their software it’s, put it like this.

I’m going to have trouble explaining it. And that’s exactly why it came to me. So their CRO called me up one day and he’s like, “Hey, we exhibit a lot of trade shows and people come to our booth and they’re like, PowerChord, what do you guys do?” And here’s the best way to explain it. They’re like a CRM for manufacturers of high consideration goods. who sell their products through dealerships. And the problem that they solve is marketing. The manufacturer will invest dollars to drum up online leads and they’ll flip it to a dealer, but there’s no central way of funneling that lead to the dealer. There’s no way to keep track of that, the life cycle of the lead.

Like where’s that at? And sometimes guess what? The dealer might represent the competition and they might close the competition. So they might, Hey, it’s like, like you’re paying for the marketing to generate leads, you’re giving it to a salesperson, the salesperson’s closing completely, closed selling the customer a completely different product, which is like not a good use of your marketing dollars.

Like, it’s quite the opposite actually. And that’s a lot, that’s a lot to explain. So, they’re exhibiting these trade shows and they weren’t having the right conversations, people weren’t getting it. And like I, I wrote them a whack of jokes. And like there were a handful of okay ones. They were a small sales team including the CRO, about six salespeople, the CRO and one senior sales guy.

They each took two jokes that they like, they each took one joke that they liked, so two total. They weren’t even that funny, they were just good little analogies. And they used that to really provoke conversation after conversation at the trade show booth. People got what they did and that led to 100k of net revenue in just two months.

In that same period, they took the jokes and I helped them build a bit of a playbook for cold email. And they got another 60K of net new revenue in that same two months off of cold email. So they closed about 160K of net new revenue in two months from just using these jokes to lead into their outreach communication with net new prospects. So that, that’s one example.

I have another client called TrustArk. And TrustArk is a SaaS that helps privacy and marketing managers manage their global privacy compliance efforts. So all the laws relating to cookie consent are changing all the time. Uh, And if you’re not keeping up with those laws, you’re going to be out of compliance.

You’re going to get fined and maybe get bad press and stuff like that. So a common challenge that those guys have is the marketing manager, marketing leadership and privacy leadership will go to the CEO and say, “Hey, like we need a better way to manage our global privacy compliance efforts. Can we have some money for a software that’ll help us do that?”

And the CEO is like, “I don’t Nah. I got other things to worry about.” And the joke I wrote for them “is CEOs remind me of my parents. The only thing they understand less than technology is privacy.” Right, and it’s simple. It’s good. You don’t even really need to understand the business to get it like and that’s what’s good about that one But it’s short. It’s quick It makes a point and it allows the buyer to get to the but seriously folks part. So those guys close some revenue off a cold email not quite sure how much I’ve heard varying numbers from leadership but the real value of working with me, according to their now CEO, was the process of crafting the jokes, helped their new hires, who were in the workshop, better express what problems would they solve for who, express it in simple English, and allowed them to ramp quicker.

Two of their six new hires hit quota in their first quarter. The other four still hit six figures. The team hit numbers. So ramp time is lower. They hit numbers. And he told me, this is the real value of what you do. And he was happy with generating some revenue from cold email, but he was happier that reps knew how to start and have a meaningful conversation.

Joel: Think that the process is what’s important is doing the doing the thought work, right? You could come in and write a book of jokes and hand them off. And if people don’t connect with the joke, they’re not going to connect with the audience that they’re that they’re presenting to which I think is a big challenge with technical communicators and companies that outsource and sort of abdicate their responsibility for figuring the words out or make the brand look good that they’re losing that.

And I think we’re also losing touch, through a lot of technology. Technology is big. I’m a big user of AI, but I’m a big detractor of letting it do the thinking or the work for you. And I think a lot of people hand over too much and formulas are good, but formulas are also need to be broken.

And I don’t, I’m not so sure that AI is to that point where it can do that independent creative thought but it can be useful. I think you talked a little bit about AI in in your workshop and how it might be used just to churn. Cause that’s a lot of the need is just to look at things in different directions.

Have you dipped into that? Do you recommend that people use it or are you staying away from it for now?

Jon: I’m torn because I think sellers and marketers and technical people who are customer facing, before they touch AI, they need to go through it and think it through and learn it manually because AI is not going to learn anything for you. It’s not going to have a conversation for you with a prospect.

At the end of the day, we, work, like I said, salespeople and marketers need to put on their consultative mind hat consultative mind hat. I don’t know what that is. Their consultative hat and mindset. Because like when we create marketing materials, do customers really care about the new features, the bells and the whistles? They care about, like what they’re trying to achieve.

They don’t, they need to better understand this. Like you said, the so what and the who cares and, pumping all that into AI and creating a list of outputs or it doesn’t mean anyone’s going to master that stuff for a conversation. They’re just going to have a list of outputs on a screen.

So I, I still believe that, To become subject matter experts, we need to do this the old fashioned way. Where I think AI can play a role is to help drill down on those problems, those impacts of not solving problems, get really specific. If we learn how to prompt it properly, it’ll help complement and round out our subject matter expertise.

But I think a good baseline needs to be there in the first place. So I think it can be very complimentary. I think it can also provide some good inputs for jokes. But again, you need to know what to prompt. You need to understand how to prompt and to know how to understand how to prompt, you need to understand the basics.

Joel: You have to have the reps in too. Talking about the experience of a comedian and going out and having a joke bomb or something not work once doesn’t necessarily mean you’re going to pitch it out. You have to do some, a lot of introspection and thinking and get those reps in.

And I think that’s what a lot of companies don’t do. They chase a messaging or this is the hot thing right now, or, well, last time we went to a conference, we used this positioning, and it really didn’t work. So, I guess what, I guess the reason I’m bringing that up is maybe it circles back to what, where we started, which was, it can be very tiring sometimes to do the same thing over and over again.

But we don’t know whether it’s we were off that day or that just wasn’t the right audience. Do you have a feel for large muscle movement numbers of, how many times do you try something before you try something else?

Jon: Well, look, I can only talk about my time in standup. And it’s a really good thing you’re bringing up because, I would trot out new material all the time. And look, there’s all kinds of places you could trot out new material, but do you want to do it in front of a hundred people at a show where you’re being paid?

Paid. Period. Because customers are paying. They don’t want to hear you experiment. They want to hear the stuff that works. And to be honest, the people who are hiring you want you to deliver the stuff that works. They don’t want you experimenting. People have paid, they want to laugh. They don’t want to go like, “I don’t understand that. I didn’t get that.” 

So, there’s a whole, there’s a whole spectrum of comedy shows that you can go check out comedians and on the extreme, maybe, I don’t know if left is the right term, but like on one end of the spectrum is crappy open mics that are mainly populated with comedians and not, no audience, maybe a drunk person who’s in the bar drinking and like, it’s just sitting at the bar and observing.

And some people there are comedy nerds who enjoy the process to be quite honest. So I would, what I would do is I’d go to one of these open mics. And sometimes there are a few people sitting there supporting the comedians, some non comedians there. There’s maybe four or five of them in there. They’ve been encouraged to move up and, because we like an audience, comedians aren’t listening to each other, to be quite frank we’re too self absorbed and focused on our own material but there is a value to getting up there and delivering your stuff, even if no one’s listening. It just, it builds that muscle memory it might not tell, if no one’s listening, it might not tell you if something is funny or not, but when there’s four or five people sitting there, I’ll deliver a new joke to them, and if it doesn’t come out anywhere near what I’m looking for, there’s two things that are going to happen. No one will laugh. Let’s say five people are sitting there. Five non comedians are sitting there. No one laughs. And that means either there’s nothing funny here or it needs, there is, it needs a lot of work.

But if I get one of them to smile, like based on what I’m saying, That means I’ve connected with someone and that there’s something here and that I need to edit and refine and iterate this. So I’ll watch my, I film myself. I don’t really perform these days, but I would film myself.

I’d go back and watch it and I’d listen back and I’d go, Oh, I know why they didn’t get this. I was too long upfront. I was too rambly. I wasn’t, the backend wasn’t specific enough, or maybe the wording was. was janky. So I’ll edit it. I’ll literally type it out on paper. I’ll try and figure out a good way to present it.

And then it’s a bit of practice and muscle memory. And then I’ll go to another open mic and I’ll deliver it again. And the second time, if it has legs, we’ll get more chuckles. And then I go, I repeat that process. The third time I’ll really edit out some words and tighten it up. And then I’m doing it usually for a bit of a bigger audience on that third time.

And I’ll slide it in somewhere in the middle of the set. I’ll start off with some stronger material, and then I’ll get to the newer stuff. And I usually have them on my side a little bit by the time I get to the newer joke. I deliver a bit of a tighter message that I have been tested a couple of times, and the audience gives it a much bigger laugh than either of the two shows even combined.

Two previous times combined. And then I’m like, oh, okay, but it’s not like this big, giant laugh. It’s like enough people are laughing and there’s a bit of a rolling laughter to it all. Again, same process. Go back, watch it, tighten it up, practice. Maybe to learn where they’re like, where they’re smiling, where they’re laughing, and learn to iterate the delivery even.

And the fourth time is usually the time where it gets the big pop. And then you start to like get a feel for it and it becomes part of your set and you enjoy telling it. And that kind of comes through as well. So there’s definitely a process. And to your point, you can’t abandon something if it doesn’t work once you have to iterate it and refine and iterate and then put it out there again and keep that process up constantly.

Joel: I’ve seen in branding, the marketing, “we’re going to come in. We’re going to do some branding and messaging work and revamp the entire website”, and maybe I need to use that metaphor. “You need to trot this out to a couple open mics.

You need to take this messaging to a conference. Try it on a couple calls before you commit to putting it in development and on your website.” And, it’s hard for people cause I think they want to see the big result. They want to rush towards the big show without, testing, having minimally viable messaging is what I call it.

But in technology, we don’t release version 1 or version 0.5 beta, right? We iterate. And so, do you find that’s hard for technical people? They hear something once and they’re going to, they’re going to take it and run with your clients. How do you suggest that they test messaging, in the market?

Jon: Look, to be quite frank, I don’t work with enough technical people. I work with a handful here and there. But they’re usually in the workshop because they have the right personality for it in the first place. So sales teams will invite the more creative ones who are smart to act as mini mentors to the salespeople because the technical resource who’s personable brings it all. Whereas the sales rep, especially if they’re younger and the marketers, they’re a little detached from their buyers. Right? And so look, everything I do is even inspired by a pre sales engineer. I worked with at Oracle. He delivered a joke on a demo. Like I teed off the demo and I tuned out cause it’s really boring stuff.

But some point in the demo, he made this joke about global financial consolidation process that process. And, They laughed and like what I read, what I was disconnected from everything he was saying, I have one ear to it all because that’s my job. And there was just enough like complex finance jargon in there that made them laugh and go that they went, Oh, that’s hilarious.

And I thought he made it up off the top of his head, but I was on another demo with him, same product, a year later, Global Financial Consolidation. He made the same joke. The same point of the demo and he got the same reaction. And I said to my colleagues, do you do, does he do demos for you? They said, yeah.

Does he use the same joke? They’re like, he’s been using that joke for years. And so he knows it works. He knows it makes a powerful point. He knows it gets them on his side and he makes it part of his his script I guess you’d call it. 

Joel: it just came naturally to him, and I guess he saw what worked. You’d said that comedians aren’t listening to other comedians. I had a similar conversation with a motion director friend of mine, and I asked him, I’m like, do you still enjoy cinema? And he goes, “not as much as I did when I was coming up, because now I can see the flaws in it, or now I know how I would do something.”

Do you continue to look at what’s happening in comedy or what’s evolving or are you starting to become a crotchety old man about it? Like, like, like some of us are.

Jon: I was probably a crotchety old man from when I started because when I started, I was in my mid 30s and I had grown up around a lot of comedy and I’d watch like both newer comics of all ages, rehash a lot of old premises, like I’ve seen this before, like, like nothing was new. The ones who were new, yes, I’d pay attention to and that isn’t to say like, look again, I haven’t, I’m not really doing comedy these days, but if I were to go back to it. The only time I would say I don’t listen to comedians is when I’m on an open mic and I’m trying to get my head together for what I’m trying to do. Like, we’re not there to be entertained. We’re there to work on our craft. If I go see a professional there’s two kinds of professionals. The ones who I really admire who are like magicians and are, they make it look so easy that, and they’re funny and I don’t have time to analyze, but then there’s the ones who exactly like you said they work at a pace where I’m like, that’s not how I would have done that.

And that kind of kills my enjoyment of it all. A trend that I really don’t like in comedy is, but it’s also a sign of the evolution of the standup comedy business, so to speak, or industry is these crowd work clips that we’re seeing. Comedians to get booked on comedy clubs and festivals, it really doesn’t matter how funny they are, it matters how big an audience they have.

And to build an audience, we all know you have to pump out a lot of content, and comedians don’t like burning their scripted material on TikTok or Instagram. So they’re doing a lot of crowd work and they’re trying to get viral, like, like unrecreatable moments to go viral. For some people it’s worked, but every comedian, younger comedian, newer comedian, I see doing that and they’re ignoring the craft itself. They just think like, “Oh, I can talk to crowds and. Be funny in the moment.” I’m like, “well, you’re no one’s going to pay for this.” Like for every good moment you get online, that’s worth posting.

You probably have like a hundred that aren’t funny.

Joel: Yeah. And I hear a lot cause I do like flipping through the the comedy comedians on TikTok. And I do. I like the ones that post bits of their set and the crowd work is okay, but you often hear, someone who gets really known for crowd work and then they get a big break or they get a Netflix special and it just, it doesn’t play.

And like you said they’re focusing , yeah, audience build. That’s a great example going back to the conversation I had with with my buddy Joel about filmmaking. So, it’s not the size of the audience, it’s the impact that you’re making on them. 

So what do you do currently to keep yourself fresh to keep to keep the humor a little bit.

I’m a big fan of classic comedians. I actually saw Red Skelton in Chicago when I was like eight years old and I will still watch, I would still stop and watch Red Skelton and George Burns and, some of those older comedians over the new stuff. Are you into the, are you, aside from the crowd work, are you into the new stuff or do you try to keep anchored in some of the classics?

Jon: Both. Like to me, funny is funny. There’s some stuff that’s super timeless. Like I think like the quality sitcoms. of the 70s and 80s. They’re like masterclasses in joke writing. So if you watch All in the Family, Diff’rent Strokes, like I was re watching it recently, The Golden Girls, like these shows are written by, clearly by joke writers.

 Watching those old comedies through my, through my more recent experiences that the lens of my recent experiences, you see the structure and you see the brilliance of it all. But I also like a lot of newer comedians. I don’t consume, I’m not some giant comedy nerd who’s always consuming.

I like comedy podcasts where they’re just talking and the ones who I like listening to, I’ll go check out their standup act. So I Sam Merrill and Mark Norman and they’re not for everyone. Nate Bargatze is a big guy and I like what he does, he’s very unconventional. I like Ronny Chieng quite a bit.

So there’s comedians I like and watch and, but I don’t need to consume everybody. It’s, it’s, I find comedy on Netflix can be hard at times. I think it’s better experienced live. 

Joel: Yeah. it definitely is. Just with some closing thoughts. If you had one piece of advice to give to somebody who is they know they’ve got a message, but they stumble over their message or their, or they just can’t get, they can’t switch their brain off to engage their their conversational.

And maybe this is more improv than than scripted. Any advice towards that communicator who’s just like, I just don’t think I’ve got it. Are they hopeless or are there things that we can try?

Jon: Oh, there’s definitely things we can try. Look, first step I would do is like, get it on paper. Put yourselves in the shoes of the person who you’re trying to reach. And look at it objectively and go, why isn’t this getting anywhere? And maybe it’s the language, maybe it’s the phrasing, maybe it’s the delivery, maybe it’s too boring maybe it’s not touching on a need.

Start to ask these questions or ask some other folks. Why is it like, why is, why would this not register? And get some feedback, like get some feedback that where the stakes are low in other words, when you’re doing a demo with a client, the stakes are high and you’re not going to get, if they don’t get the deal, if you don’t get the deal if you’re a pre sales engineer or. or you’re a marketer, like, don’t do it where the stakes are so high. Ask some colleagues or some past clients that you have a good relationship with, like, why, like, why isn’t this registering? And get their take on things. But understand it, like, start, you don’t know, you’re not gonna be able to fix a problem until you know you have one. 

Joel: We should we should launch SaaS demo open mic nights.

Jon: oh God, I don’t know. That can be pretty painful to be quite honest, because I’ve, I think Most, a lot of SaaS salespeople probably would pain us, basically, qualify for this show. So look I say, get it down on paper, figure out what’s going wrong with it, and then figure out how can I iterate this and how can I repackage this using simpler language, simpler phrasing, stuff that could, that people relate to a little bit better and try and find a new way of repackaging it. 

Joel: Well, and, or call Jon because cause you are there to help. How can people follow you, get involved, see a little bit of your work? Drop some plugs and some links.

Jon: Yeah, absolutely. Look, there’s three ways to get a hold of me. One is my email, Jon, there is no H in Jon, J O N. at J O N S E L I G dot com. And of course, that’s my website too, where you can read up on all the grand things I do, whether it’s humor as a service, whether it’s trainings and workshops it’s jonselig.com. And of course, LinkedIn, find me there, follow, connect not posting as much content as I once did, but connect and we can have a

conversation. 

Joel: Well, Jon, this has been a super pleasure. I had a great time out in Philly, hanging out. We’ll have to do Chinese food again, and talk movies. That was that, well, we should have recorded that. That would have been a whole episode the three of us, but. Again, thanks for taking some time helping us understand a little bit more about humor and comedy.

And I will now be a little worried when you see my posts that they might not be might not be landing. So, be kind.

Jon: will, I will. I’ll support it regardless. Thank you for having me. This was a great conversation. And hopefully we can do that Chinese food again in the future. 

Joel: Thanks for joining.

Jon: No problem.
 
 

Joel: If you want links to the resources mentioned on the show, head on over to the episode page. And for information on booking a message therapy workshop, getting your hands on the MessageDeck, to check out my upcoming book, or just buy me a coffee, go to nerdthattalksgood.com/podcast. 

 Until next time, happy messaging.
 

 Remember, you don’t have to speak well, you only gotta learn how to talk good.