A Comedian’s Formula for Your Perfect Pitch with Jenn Lederer

| 28-min read Stay updated

If your mind goes blank when someone asks what you do, this episode of the Marketing Mentor Podcast is for you. 

In my conversation with comedian and keynote speaker, Jenn Lederer, you will learn not only how to enjoy talking about your work but how to do it in an entertaining and authentic way.

Here’s Jenn’s baby step: Open the notes app on your phone and make 3 categories: what you do, how you do it and why you do it, next steps – then, over the course of the next week, make a note every time something comes to mind.

This is the beginning of your living, breathing elevator pitch, which can (and should) be constantly changing and adjusted depending on who you’re talking to. 

So listen here (and below) and learn: 

And if you like what you hear, check out Jenn's YouTube channel too.

UPDATE: And the really cool way she shared this episode on LinkedIn -- please comment!

And we’d love it if you write a review, subscribe here and sign up for Quick Tips from Marketing Mentor. 

Read the complete transcript of Episode 483 with Jenn Lederer

ilise benun

Hi there. This is ilise benun, your Marketing Mentor. And this is the podcast for you if, and only if, you are ready to leave the feast or famine syndrome behind, and I mean for good.

If your mind goes blank when someone asks what you do, this episode is for you. In my delightfully deep conversation with comedian and keynote speaker Jenn Lederer, we covered everything from how to use the comedian's formula to develop your perfect pitch—which shouldn't be perfect at all by the way—to what confidence is, always interesting. Plus, how to tell a good story in real time, and so much more. We had a couple technical hiccups that affected the sound quality, especially near the end, but you know what? Who cares? It's a great conversation and I am confident you'll like it. So, listen and learn.

Hello Jenn, welcome to the podcast.

Jenn Lederer

Hi, ilise. Thanks for having me.

ilise benun

Of course. So Jenn, what do you do?

Jenn Lederer

I'm a comedian and keynote speaker, and I help entrepreneurs and creatives storytell their career using a comedian's formula.

ilise benun

Nice. And we met because we're both friends of Terri Trespicio, the amazing Terri Trespicio.

Jenn Lederer

She's the best.

ilise benun

She is indeed. And she's an excellent networker. And so we met at HOW Design Live, in Nashville, but we didn't really get to chat much there, and I was very interested in your HOW session, but it was so packed, I couldn't get in. So why don't we start with you giving me the top line on what it was all about? What was it called and what did you cover?

Jenn Lederer

Sure. It's called The Perfect Pitch - HOW to Talk About What You Do and using a comedian's formula. I teach people how to talk about their work, their value, their passions, what they're interested in, how they differentiate themselves within their industry, in a way that is entertaining and connects you to the people that you're talking to versus trying to be the most impressive person in the room—which nobody likes that person. So how to be human while talking about yourself.

ilise benun

I love that. And I don't know, why do people struggle so much with this simple question: what do you do? Because I've noticed that often, it's almost like your mind goes blank when someone asks you a question about the thing you probably know the best.

Jenn Lederer

Right? The thing that we spend the majority of our time doing, we suddenly are alien to as soon as someone asks us to explain it.

ilise benun

It's bizarre. Why do you think that is?

Jenn Lederer

From what I have seen, there is a dissociation that happens. It's like, as soon as somebody asks us: “What do you do?” we dissociate from ourselves and try to jump into that person's mind and body, and figure out what they want to know about what we do. And so that's where we start to try to be impressive or try to give them what they want. We try to be a mind reader. And now you're not present with yourself and you're really not even connecting to what excites you about your work because you're so concerned with exciting them about your work.

ilise benun

Right. And you referenced “the comedian's formula” and you said you are a comedian. So tell us what is the comedian's formula and how does it relate to this elevator pitch idea?

Jenn Lederer

Sure. So in a comedian's ‘tight five,’ which just means a five-minute set, the point of it is to give people ... usually there's three different topics that a comedian will cover inside of those five minutes.

To give you an idea of, if you followed me on social media, if you watched a longer set, if you came to one of my shows, this is the kind of thing that you could expect to get more of. So I basically give people the three topics for you to explore and create stories around—which is answering the questions: How do you do what you do? Why do you do what you do? And what's next in what you do?

ilise benun

I love the question, “Why do you do what you do?” Because first of all, I think not many people get asked why do you do what you do?” They're much more focused on the how and the what.

But I think the why is of much more interest, and everyone has a different reason for doing what they do, even if 10 people are graphic designers or copywriters—which is a lot of the people who listen to me—but they really struggle with this question. And I'm liking this idea of bringing the why into it. So maybe, if I asked you, Jenn. You said you're a comedian and a keynote speaker. Why?

Jenn Lederer

So this is actually one of the things that I very recently kind of nailed down—which is another part of this that I emphasize to people is, you're going to be talking about yourself and writing about yourself for a long time, usually, before you start to actually clarify these answers and really feel them as true in your body.

And what I've landed on is why I am so passionate about storytelling and teaching others to storytell is because it's how I've realized that I was queer. It's actually how I got to the core of my own truth, and I started seeing the patterns of the jokes I was writing and the things, the themes that I kept going back to. I was like: whoa, whoa, whoa. Who is this voice? Who is she?

And I've just found and seen in my own clients ... listen, unfortunately, you're not going to all come to the conclusion that you're queer.

Like, sorry, not everyone's going to have that arc. But you do get to peel back your own layers and figure out why you do what you do, how you do what you do, and what makes it so different.

And there's a type of connection that you build with yourself and your business and the stick-to-itiveness that's required to be your own boss, that in those moments where you want to quit, in those moments where you're second guessing everything, when you are really connected to your story, it helps you to keep going and it helps you to use your voice.

ilise benun

All right. So now I have too many thoughts all at once, and I'm just going to pick one and hope the other ones come back.

So I was actually listening to Yuval Noah Harari this morning on a podcast, and he was asked also about his realization that he was gay. And he basically said, "I know it's possible not to know something so core about yourself, "because that was the question: how can you not know?

And so when people really struggle with who they are, especially as it relates to what they do and how to talk about it—because you're not going to go around telling everyone that you're queer or you're whatever it is—but I just was thinking about this. You called it in a previous conversation, “a spiritual experience where you meet yourself” and it sounds like that's what you're referring to now.

Jenn Lederer

Yes, and even before I was focused on storytelling ... you know, I've been my own boss since 2009, and I met every space of resistance within myself through building a business. Every excuse I have to buy into scarcity, to believe that I'm not enough, to focus on everything but my own lane. All of those patterns that keep you small are going to come up when you run your own business.

And when the buck stops with you, and when the truth is, if you don't show up, there is no money coming in, you have no choice but to face these things within yourself.

You know, there's a lot of ways that we can hide from ourselves in life. Not when you're a business owner. You really can't afford to hide from yourself; you have to keep showing up. It's a spiritual experience.

ilise benun

Right. So interesting. I mean, now you're making me think about confidence, and a lot of people, especially people who struggle with this question and blank out when they're asked: “What do you do?” seem to also struggle with a lack of self-confidence. And you sound like someone who's very confident. But I also know that often people who sound confident aren't always, or in certain situations, they don't feel that way. So I'm curious, do you think of yourself as confident?

Jenn Lederer

Okay, so what's interesting is I decided to look up the definition of “confident” and “confidence.”

So, confident, they say, is feeling or showing confidence in oneself. And I was like, well, that's a useless definition. So let's look up confidence: the feeling or belief that one can rely on someone or something; a firm trust.

So if we go with that definition, yes, I believe that I see myself as someone with confidence because when I look at my path so far, what I see is someone who, no matter what, gets up again. No matter what, I have my back. I have the ability to pivot, to change my mind, to speak my truth, even when my voice shakes. And that has shown me that even when I don't feel confident, I can rely on my confidence that I have my own back.

ilise benun

Well, it sounds like you're describing being your own best friend.

Jenn Lederer

Yeah.

ilise benun

That's interesting.

Jenn Lederer

Yeah, that's a lot of therapy work right there. (Laughter)

ilise benun

We went very deep, very fast, which I always love. But let's try to bring it back to the practical, a little bit. And you were talking about storytelling, and actually one of my clients last week asked, "How do you tell a good story in real time?" And I was curious how you would answer that question.

Jenn Lederer

Usually the best stories are ones that you've told before. They're the stories that you really know. Whether you have a script about it or not is irrelevant, but you know it in your body. There's a way that when you start telling it, you almost are right back in that moment. And again, you're not telling it to try to get some sort of reaction. You're telling it because you’re connected to it.

And when we are interested, when we are excited, when we are lit up, that automatically invites the people who are listening to also be lit up. Right? When you hear somebody talking about their most favorite food, even if that's not your favorite food, you're like, “I don't know. Maybe I want to try it now because this person is losing their mind over this thing. So I don't know. I'm curious.”

ilise benun

What's your favorite food, Jenn?

Jenn Lederer

Okay, so Italian hoagies, specifically from Pittsburgh; that's where I'm from. And it's a certain kind of “sub” is what they call it in the rest of the land. But in Philly and in Pittsburgh, they're called “hoagies.” And it's something that I get every time I go back to Pittsburgh.

ilise benun

And I love the connection that you're making. I have my version of talking about this. You make a connection, or a distinction actually, between being interested and being interesting. And you're saying, what I hear you saying now is, stop trying to be interesting and instead be interested—whether it's in what you love or what the other person does or says or anything. And I call that “using curiosity as a marketing tool.” What do you think of that idea or phrase?

Jenn Lederer

Yes, absolutely. Curiosity gives permission to not have an opinion about the thing. Right? You're just getting information. You're sharing and learning data about a thing. You don't always have to have an opinion about it or feel that it's right or wrong or good or bad. It's just like, can we create a space where this thing can exist and we can get curious and interested about it? That's innately a fun conversation.

ilise benun

Okay, now you're making me think about another podcast. I heard Tom Hanks was on Ezra Klein recently.

Jenn Lederer

Oh, compare me to Tom Hanks right now. Compare me to Tom Hanks. (Laughter)

ilise benun

And he said “authenticity,” because really what you're talking about is: be yourself, right?

Jenn Lederer

Correct.

ilise benun

Relax and be yourself.

Jenn Lederer

Correct.

ilise benun

That's the main message here when you're answering the question: what do you do? And he said, “authenticity is when you share a moment rather than perform a moment.”

Jenn Lederer

Boom.

ilise benun

Right?

Jenn Lederer

Yes, yes.

ilise benun

I just love that idea. And so if we can relax and just let whatever happens in that moment when we're just trying to share the moment instead of doing a performance, essentially.

Jenn Lederer

That's right. And within that, I would say get comfortable with the silence. If somebody asks you: “what do you do” and you feel yourself dissociate, take a minute, breathe, be like: “You know what? Hold on, I'm completely dissociating from my body right now.”

ilise benun

That's right. Say it right, say it. "My mind is blank. Isn't that bizarre?"

Jenn Lederer

Yes. And then they say, "Oh my God, the same thing happens to me. That's why I asked you first, so you didn't ask me."

ilise benun

That's right.

Jenn Lederer

And now you're connecting. And now it doesn't actually even matter what you were going to say.

ilise benun

Or what you do.

Jenn Lederer

Yep.

ilise benun

Okay, so connecting, right? I mean that seems to be the whole point of this question also, which I don't think most people understand. So talk a little bit about this idea of connecting—what the key to connecting is, because we’re kind of circling around it.

Jenn Lederer

So if I compare it to a comedian's formula, the point to getting on stage is laughter. That's my objective. Now, on the other side of laughter is connection. So anytime that you are talking to any other human, your objective is connection.

Now, you might do that through laughter. You might do that through an authentic or vulnerable story. But the point is not to convert this person or convince this person of anything. If you look at every conversation as: my objective is to connect, then suddenly you aren't worried about that whole impressing them or being the most interesting person in the room. You are present to: is this person with me right now? Is this person buying into the stories that I'm sharing? Or can I see that they're looking around the room; they can't wait to end this conversation. They're trying to get to the bar. And then, by the way, you can speak to that. There are moments where I have been talking to someone and I'm like, "Hey, I actually don't need to finish this statement. You're free to go."

ilise benun

What did they say?

Jenn Lederer

Honesty is a great connector.

ilise benun

I agree.

Jenn Lederer

One of two things will happen. They will either acknowledge, "Yes, you're right. My brain is all over the place. I apologize, I'm present, I'm here. Please keep going and thank you for calling me out."

Or in that moment, oftentimes they will get really honest. Like, whatever I was saying becomes irrelevant because they will tell me what's on their mind, whether it's something they're really excited about. “I have my wedding coming up soon,” or “My sister just had a baby, and I'm just, I'm thinking about all of that.” Or “Someone in my family was just diagnosed with something; someone just passed away.”

There's all of these human things that are happening in our life all the time. We come to these conferences, we go to networking events, and we think that our wholeness of a person is supposed to be compartmentalized, and we're supposed to only walk in with our business hat on.

It's like, no, come in as a whole-ass human and let me connect with that. So if I see that you are distracted, if I have the confidence to sit in discomfort, to sit in imperfection, and then I am the one to lead that and give permission to be curious about why are you distracted? And then you feel comfortable enough to be honest? Oh my God, we're friends forever. We're besties now because we just connected in a way that actually matters. And again, it's irrelevant whatever I was just saying, because we can skip past all of that and actually connect.

ilise benun

And I think the reality is that we don't connect with everyone. In fact, maybe it's rare when we actually connect with someone, whether it's over the fact that you both love dark pretzels. That's one that I've connected with someone over, or Italian hoagies or a movie or whatever it is. But what about when you don't connect with someone? That can be awfully awkward, right?

Jenn Lederer

I mean, I guess, but you can also just move on. It's really not that big of a deal. Do you need everybody in the world to connect with you? How overwhelming. Could you imagine 7 billion people connecting with you? The introvert in me wants to crawl under a rock.

ilise benun

Right. Right. So it's not necessary. I like to say, “Who cares,” right? “Just move on.”

Jenn Lederer

Who cares? And if you're not worried about being interesting, it's actually a neutral experience. It's not good or bad. We're always looking for alignment. We're always looking for real authentic connection. And if we're not in alignment, let me get out of your way because there's somebody here that you are aligned with, so go find them.

ilise benun

And me too. Right?

Jenn Lederer

Exactly.

ilise benun

We'll both find our people. You're looking for your people.

Jenn Lederer

Correct. It's dating, right?

ilise benun

Now. You talked about wholeness; come in with your wholeness. And that makes me think about the compartmentalizing I see people do between their business mind and their creative mind. So talk to that. I know you have some ideas about that as well.

Jenn Lederer

Yeah, I've been in the entertainment business my whole life and I've done a lot of mentoring in several different avenues. And then in my corporate experience, I see the other side of this where business-minded people are convinced that they don't have a creative mind, and creative-minded people are convinced that they don't have a business mind.

And first of all, everybody is innately creative. That is the human expression and experience. Your creativity might have to do with science and numbers and analytics and how you see the world, but that's still very creative.

And then on the business side of things, Fortune 500 companies are bringing in creative minds to stay relevant, in order to know: how do we pivot; how do we evolve from here? That's creativity. The creatives are the ones who can look at a blank slate, who can look at infinite possibilities, and start to say: “This is the direction that we want to go.”

So knowing that as a creative mind, you are not only relevant but one of the most important voices in business in staying relevant. But then also that you have the ability to be a business mind. It's innate in who you are also.

ilise benun

What is that, a business mind, to you?

Jenn Lederer

I mean, it's really about knowing how to package. Right? Knowing how to take your creativity ... When I was a talent manager for five years, I did this a lot with my actors, is taking this thing that is so close to your heart, and being able to step away from it enough to look at it from kind of a disconnected place and see, honestly, where does this sit inside of my industry? Where does this sit inside of the conversation that's being had as a whole, and detaching your personal value from it.

“If this pitch doesn't go well, then I am a failure?” No! It just needs to be tweaked a little bit, maybe. Or that pitch wasn't aligned to begin with; you weren't supposed to be working with that person. So being able to kind of create a little bit of space between you and your product or service to speak on it from just a more impersonal way helps, I think, with the business mind.

ilise benun

And starting with the elevator pitch, cuz as you were describing that, I was thinking, well, it starts in that moment where you have to answer the question: what do you do? And realize from a very objective, depersonalized position that it's really not about you, and you want to say something that will connect with the other person—which may not really be about you.

Jenn Lederer

Yeah. It most likely is not about you, at all.

ilise benun

Which is a bit of a paradox, right?

Jenn Lederer

Right. It's like there's you all over that question. And really it is about the audience. It's always about the audience. Good storytelling takes care of the audience. You take them on a journey and they feel safe to follow you.

ilise benun

And I'm curious, then, what you think of my elevator pitch? Because when people ask me, I say, “I teach creative professionals how to get better clients with bigger budgets.”

Jenn Lederer

I love that so much.

ilise benun

Why?

Jenn Lederer

Because it speaks directly to my goal. It's like, of course I want better clients with bigger budgets. That's an easy “yes” for me. It creates an easy sense of curiosity of like, ooh, okay, so how do you do that?

ilise benun

Do you feel like there's a story in there? Is there a storytelling element to just even that simple phrase?

Jenn Lederer

I think the story that's being told in that phrase is a level of confidence and experience. Right? Innate in that is someone who is connected, someone who has a network, someone who probably has been around the block a few times to know enough people to be able to claim this. So I would say the subtext of that story is someone who really knows what they're talking about.

ilise benun

So that's an interesting idea, also, that your story doesn't need to be overt. It could be covert. It could be implied in the description of the effect of your work. That's interesting.

All right, I have a couple more questions and then we're going to get to the baby step. I think what I wanna focus on ... someone asked me this recently also, and I like to ask my guests the things that people have asked me lately. And we've been talking a lot about LinkedIn in a particular group I'm leading and how to reach out. We do “targeted outreach” is what I call it in the Simplest Marketing Plan, when you reach out to strangers, essentially.

And someone asked me: “Well, how do you reach out to a thought leader or someone that you admire and you just wanna ... like you like them and you want to be their friend maybe, or you're not really asking for anything, it's not a prospect. But what would you say to someone like that?

Jenn Lederer

Well, first, what's the energy that you have in the outreach, meaning take them off the pedestal. Whatever pedestal you have them on, remember that you are both human. You are equal. And speak from that place.

And then, compliment them. Show them that you have researched their work; that you are actually a fan. Maybe share one of the ways that their work has inspired or transformed your life or the way that you move through your own work. And really just speak from that place of, if this person is my equal and I really respect their work and I want to show them that, here's a story I can tell that shows that. That highlights that. I'm not asking for anything.

And the other piece to being equal to them is they're human. They have insecurities. They are doubting themselves a hundred times a day, also. So it's always great to receive messages that remind us that what we do matters. It does not matter how big your audience is, how successful you are. Those types of things matter and people remember how you make them feel.

ilise benun

And I'm going to compare you to Tom Hanks again ...

Jenn Lederer

Yes!

ilise benun

... because he was talking about this in the conversation with Ezra Klein also. And he basically said, when people come up to him and ask him for a selfie ... I don't know if he said he says “no” or something, but he's not really interested. But if someone comes up to him and says, “That time you were in that movie impacted me so much and here's how,” so essentially telling a story, as you're saying, then he really does want to know that because his goal is to have an impact on people. And so when people tell you what the impact has been, I find this too, it is very gratifying.

Jenn Lederer

Yes. That's right.

ilise benun

Really interesting.

Jenn Lederer

Oh God, I'm basically Tom Hanks. So... (Laughter)

ilise benun

I think you would really enjoy that podcast conversation, too.

Jenn Lederer

Yeah, I'll have to check it out.

ilise benun

All right, so, all right. Final question here, Jenn. Do you have a baby step that listeners can take toward their perfect pitch is kind of the through line here.

Jenn Lederer

Open the Notes app in your phone, all right, and have three different areas: How do I do what I do? Why do I do what I do? And what is next in what I do? And for the next week, every day, be open to a different story, anecdote coming to you, and write it down.

Now, here's the thing. These stories are going to come to you while you're in the shower, while you're doing the dishes. Anytime your hands are wet and you're unavailable to write the story down, this is when it's going to come. Okay? So you have to be prepared for that. But I would say just start the conversation with yourself and get curious about these stories.

This is the muscle that I build the most as a comedian, is constantly looking around the world and my world, mining for stories and what it is that I want to share to connect with my audience. And that's how you should be looking at your business. You are constantly mining for stories that showcase you and how, why, what you do.

ilise benun

And I think implied in what you're saying also then is that there's no right answer to this. There's no right elevator pitch. In fact, maybe there's no perfect pitch.

Jenn Lederer

That's right.

ilise benun

And you take all of these elements that come to you over time and not just during that first week. Mine is really constantly evolving, and I keep thinking of new ways I do what I do. And I keep changing how I do what I do, anyway.

So this idea that ... because I think often people (think): “Okay, I got it. Now I've got it,” about their elevator pitch. And I'm like, no, you will never get it. And it will be constantly changing and just get used to it.

Jenn Lederer

Yes. And it should change based on who you're talking to, right? You should read the room a little bit and have, when you have enough stories collected, you can start to know: okay, this story is really going to connect with this person because X, Y, Z.

And so every time you talk about your work, it should evolve and sound different, because as soon as you ‘got it,’ you're going to sound like a robot.

ilise benun

Right? Yeah. All right, we'll probably have to do a Part Two of this because there are lots of other things coming to mind that then disappeared. So...

Jenn Lederer

Great.

ilise benun

I thank you so much, Jenn, for sharing everything you've learned in your process, in your life. And tell the listeners where they can find you online, and if you want to offer something, feel free.

Jenn Lederer

I am at Jenn Lederer on all of the socials and jennlederer.com is where you can go to sign up for my newsletter. I am almost always offering different resources and free things on there. So sign up for my newsletter and you'll get the latest and greatest from me.

ilise benun

Awesome. And that's Jenn with two Ns.

Jenn Lederer

Double N Jenn, baby.

ilise benun

Awesome. Thank you so much. Thanks, Jenn.

Jenn Lederer

Thanks, ilise.

ilise benun

So here's Jenn's baby step. Open the Notes app on your phone and make three categories: What you do. How you do it. And why you do it, and next steps. Then over the course of the next week, make a note every time something comes to mind. This is the beginning of your living, breathing elevator pitch, which can and should be constantly changing and adjusted depending on who you're talking to.

So if you want to build a thriving business on your own terms, the first step is to sign up for my Quick Tips at marketing-mentortips.com. Once you're on the site, you'll find lots more resources, including my Simplest Marketing Plan. So enjoy, and I'll see you next time.

 

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