#63: Jay Acunzo – How to tell great stories with a professional speaker and veteran podcaster

June 29, 2021

#63: Jay Acunzo – How to tell great stories with a professional speaker and veteran podcaster
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Jay Acunzo is an author, speaker, and showrunner. He's the host of 3 Clips (recently acquired by Castos) and Unthinkable, which he describes as Radiolab for creators.

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Jay Acunzo is an author, speaker, and showrunner. He's the host of 3 Clips (recently acquired by Castos) and Unthinkable, which he describes as Radiolab for creators.

Jay writes a weekly newsletter called Playing Favorites, a membership called Make What Matters, and in 2018 he published his book, Break The Wheel: Question Best Practices, Hone Your Intuition, and Do Your Best Work.

With a combined 15+ years of public performance and creative projects working with companies like Google, ESPN, and HubSpot, Jay's goal is to demystify the creative process – because anyone can make things that make a difference. 

In this episode, we talk about how Jay built an appreciation for creative nonfiction, what it takes to be a good speaker, the storytelling frameworks you can use, and why Tension is at the core of a good story.

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Jay Acunzo 0:00
Really I love telling stories. And I think stories are problem solving vehicles. Inherent to a story is some kind of tension. It's like the carbon element. And without tension, you don't have a story.

Jay Clouse 0:13
Welcome to Creative Elements, a show where we talk to your favorite creators and learn what it takes to make a living from your art and creativity. I'm your host, Jay Clouse. Let's start the show.

Hello, welcome back to another regular episode of Creative Elements. I hope you enjoyed last week's crossover episode with Ryan Hawk of The Learning Leader Show. That was a fun one to put together constructing an episode of this show. But pulling myself out of the host and interviewer role. It was a little bit tricky. So thanks for humoring me. But this week, the world is back to normal. And I am here to interview another fantastic creator that I can't wait for you to learn from. Over the last couple of years. I've heard a lot about today's guest. His name is Jay Acunzo. And there seems to be a lot of overlap between people who like my work and people who like his work, because not only was his work frequently referred to me, but people began telling us both on Twitter that we should collaborate. Jay is an author, a speaker and a showrunner. He started his career in marketing working with ESPN, Google and HubSpot. By the way, if you've never heard of the term showrunner before, think of it like a lead producer for a high production show, television or audio, and now having spent a lot of time following Jay's work, it's that level of production and care that he puts into things that really stands out for me. He currently hosts two podcasts. One is called 3 Clips, which was recently acquired by a podcasting platform called Castos, and the other is called Unthinkable, which he describes as radio lab for creators.

Jay Acunzo 2:04
Unthinkable started as a side project, and I wound up driving actual business my way but not directly, not through like sponsorships. Instead, it was speaking gigs. It came in the form of sales of my book, Break The Wheel. And then about two years into running Unthinkable. I started to get inquiries from brands to make shows for them.

Jay Clouse 2:23
So Jay made a documentary series called Against The Grain with a company named Help Scout. He created a podcast called Exceptions with a company named Drift. He even made a short series called I Made It With My Friends Over at Podia. And along the way, he was making a living on stage as a speaker.

Jay Acunzo 2:41
I mean, I just get this charge. Every time I step on stage. There are so many people who love this brand. There are even people in the world who get tattoos of the logo on their legs. For example, no, totally kidding. No. Can you imagine? Absolutely not. I would no longer be married. No. But people do that. To be able to travel around the world and make other people feel things or ask big questions. I mean, like it's, it's addicting. It's it's the best job in the world.

Speaker 1 3:10
So warm round of applause for Mr. Jay Acunzo.

Jay Clouse 3:17
Jay is a consummate and well respected storyteller. And that's not by accident.

Jay Acunzo 3:23
My grand delusion, I'd say aspiration. But let's be honest, this sounds like a bit of a grand delusion is to be the Anthony Bourdain of workplace storytelling.

Jay Clouse 3:34
And he's been doing that for years through his work with Unthinkable his book Break The Wheel, and his newsletter Playing Favorites. He says his goal is to demystify the creative process, because anyone can make things that make a difference. And to get there, we have to cut through conventional thinking in search of something better.

Jay Acunzo 3:53
I just feel like what Bourdain did his cnn travel show was called Parts Unknown. And I think the parts that were unknown were not the geographic ones. I mean, yeah, sometimes you didn't know that place. But his skill was to sit down with people who were just living their lives, and to bring out profound meaning from the seemingly day to day. I mean, that's, I wanted to say magic, but that's a skill. Think it's a learnable skill. And there's some things that maybe were ineffable about Bourdain, for sure. But that central skill applies to the workplace.

Jay Clouse 4:26
So in this episode, we talk about how Jay built an appreciation for creative nonfiction, what it takes to be a good speaker, the storytelling frameworks you can use and why tension is at the core of a good story. I'd love to hear your thoughts on this episode. As you listen. You can find me on Twitter or Instagram @JayClouse, give me a shout and let me know that you're listening. I'd love to hear from you. But now, let's talk with Jay.

Jay Acunzo 4:58
Yeah, I mean, I learned I'd rather Make the thing that you're trying to consume, then be responsible for the thing interrupting that. I remember to pluck out one specific story I was when I was working at Google. I was in ad sales. And I remember somebody sent me a YouTube video that I'd watched like five times throughout the day, and I went home to my, my, then three roommates, because I was in my early 20s, living in Cambridge, Mass. I was overselling it to them to say the least I was like, This is the greatest thing you'll ever see. And you know, it's funny, uplifting, it's well produced, like, just you just got to watch it. And they were like, Okay, and then he knows the height of their anticipation. I hold my laptop, I went to the URL, I click play on the video. And of course, what happens is not the video playing but an ad. And it was before the skip button. So I felt, I felt ridiculous. And then I had this second thought, which was probably only possible for me, and maybe five other people working at Google at the time to have the thought was dammit, Eric, because Eric was my colleague at Google, who had sold this advertiser on the idea of doing YouTube pre roll ads. So it's like God dammit, Eric. And then one of the worst feelings I've ever felt in my career, right on the heels of that was this like, not in my gut, because I had the same job at Google that Eric had, which means that someone somewhere had a worse moment in their life, however short, because of the work I did, and given the fact that it's Google, and YouTube, that scale meant it wasn't one person. It was 1000s, if not hundreds of 1000s if not millions of people. My success was predicated on the fact that I would introduce millions of moments of frustrating experiences into people's lives. And that is not why I got into the workplace. That is not what I exist to do. You mentioned ESPN, I wanted to be a sports journalist. I want to write columns and feature pieces and tell stories about you know, I often joke these like saccharin stories about like an athlete's hero's journey. I wanted to do that stuff. I love that stuff. And I didn't find a foothold in that industry. It was 2008, the economy was in the tank. And ESPN told me they had a job lined up for me full time after an internship. And I was in their PR and comms department and the economy prevented me from getting that job. And my ego took a big blow and, but I got very lucky with that job at Google, or so I thought I hated it. I hated doing these things that basically interrupted the experiences that people actually wanted. And so I quit Google, I got into content marketing and content creation and never really looked back.

Jay Clouse 7:25
Wow, kicking this off with a strong story, which I love. Going back to this, this little nugget you dropped about sports journalism, and you're interested in being a sports journalist. I had a similar interest in college. And that came from a love of sports, not a love of storytelling. When did you start to appreciate storytelling as an art form?

Jay Acunzo 7:43
I came up a Bill Simmons fan like millions of other people who felt like I saw myself in part, at least a tone of voice that I appreciated from him as a writer, and others like him, you know, like the the early version of his columns were a little bro he for my taste, but I saw the fact that he was able to just be himself be a fan and still tell stories and appreciate things and, and right from an emotional perspective, instead of this, like, old school journalistic approach, which said that you had to be a vessel you had to remove yourself. It was about collecting facts and distributing those facts. And don't get me wrong, a profound service to the world that we need more of, but just not what I wanted to do as a writer. I wanted I loved creative nonfiction in school, for example, where it wasn't just the gathering of facts and reporting of those facts. It was inserting your own subjective points of view and belief, right down to the ability to just describe how something made you feel in the moment. You know, there's a cliche in sports writing where you open a feature piece on an athlete by kind of like describing something seemingly mundane about their work or their day, as the strong open like,

Hey, opened his locker.

Right? Jay Clouse sat down on the bench. It was the same bedsheet sat on for 16 straight years, right? And so like, it's an mundane thing, and then yet, you amplify it with a little bit of an open loop, because you're like, 16 years, what's the deal with this bench? Right? So that's kind of like a little cliche in sports journalism, but I fell for all that stuff early on, and I really wanted to pursue that kind of writing. And so, you know, I think the reason if I had to summarize it is sports provided this nice microcosm of the human experience with a nice, neat set of rules and characters and storylines. So it was like, it was like a snow globe, I could hold up and turn over and find interesting stories. And so when I was a student, for example, I started writing a sports blog, called All Star blog. com still waiting for the big money offer for that URL. I still own it still live gathering digital dust, but I started to write that kind of stuff. I started to try and mimic my heroes. And what I found Jay was like, I think I have a I have these two talents, which is a flair for the dramatic, which helps in storytelling, and a love of the dramatic like those saccharin stories. And then also like a built in ability to mimic people that I admire fairly closely until I figure out what my version of that is. And that that couldn't have happened if I didn't A, fall in love with this more colloquial style of sports journalism, and then B, start tinkering on the side, like using these digital tools that were emerging like blogger at the time to just make stuff and just put in the wraps.

Jay Clouse 10:19
I am so jealous that you had a creative nonfiction class in school because it strikes me that literally all I do right now is creative nonfiction. And that's like a beautiful title of it. And that's a beautiful way of thinking about it. And in large part due to your work, I'm thinking more and more about storytelling. And so seeing this and appreciating it is different than explicitly understanding and deconstructing it. So like, if you came up with Bill Simmons fan, at what point did you realize that Oh, his style of journalism is different? And I can do storytelling, while being nonfiction? When did you actually appreciate that structure?

Jay Acunzo 10:54
I would imagine, I mean, it's hard to say exactly. But if I had to try and put my finger on it, I would imagine it was probably when I started to write columns in the student paper, as a student and as a college student, and had people say nice things about it. I think we undervalue qualitative feedback, especially in our age of like, analyzing and measuring everything through technology, some of the best signal, especially early but I think always is qualitative is a small number of people reacting in big ways. So you know, I have this hypothesis, and maybe this is a book someday, that a lot of the creative people we admire, had people early in their lives, tell them like, hey, you're kind of good at that you should do more. And then you go, oh, and then you do more. And then people say, Oh, you're so good at it, you do more. And so the body of work you're able to build before there's any stakes. Besides playing, there's any stakes professionally, it actually does add up to a more successful creative career. And maybe that's actually the thing, maybe you become an illustrator, because people said you were good at drawing, or maybe it's a tangential thing. Like, you used to play a lot of music, because people said you were good at music. And there's something about that craft that now translates into your professional life as a journalist. Right. So that's more tangential. But I do think it was, it's very simple. Like we always look for something sneaky. I think it was just getting addicted to the process of creating because it made me feel and the feeling I knew it was instilled in others, and getting that small signal that yes, like confirmed, people did feel that way, too.

Jay Clouse 12:23
I love that. And I totally agree with it. in the infancy of this show, which I think the show is still in its infancy. The most powerful feedback I get is qualitative. And people saying, This is my favorite show. Unbelievable piece of feedback that keeps me going day after day. And I feel like you're right, that's probably the precursor to seeing quantitative feedback, because for 10,000 people to love something, you probably have to have 10 people who love something, or it's not going to get there. I want to zoom in a little bit more on storytelling, you mentioned you have this flair for the dramatic. How does that play into storytelling? And if it makes sense to introduce this now, I also want to explore what makes a good story?

Jay Acunzo 13:00
Sure, you know, I mentioned Google, that I went to a small startup. And I ran their content marketing team, which was me. And then I hired a small team of writers and designers to produce content that educated people on how to do good marketing. And I worked for a couple marketing, tech companies, publishing content that teach marketers how to be good marketers. And then, you know, for the last few years, I've been out on my own creating shows primarily about the workplace, about creativity in the workplace, about business as a force for good, you know, podcasts and documentary. And I'm in love with narrative and docu style and storytelling. I do love interviews. I hope I'm a decent one decent interviewer. But really, I love telling stories. And I think stories are problem solving vehicles inherent to a story is some kind of tension. It's like the carbon element. And without tension, you don't have a story, you just described a bunch of stuff. It's like a statement of fact. And so you can really boil down a story to its like most foundational, basic, simplest formula, I call it the one simple story, which is status quo tension resolution. And the the thing that gets me is in the corporate world, a lot of people say what they do is storytelling, but they create case studies, or they create slogans, or they just dole out statements of fact. But we've been learning storytelling since we were children, like, in the US, The itsy bitsy spider. Okay, How simple is this? The itsy bitsy spider went up the waterspout. That's not a story. That's a description that is kind of like how people in the corporate world that I was surrounded by for many years. think of themselves as storytellers. The itsy bitsy spider went up the waterspout. It's not a story until down comes the rain and washed the spider out. Now there's some tension. Now there's an open loop that you want closure, like we're hardwired to want that resolution to the story. Now that you've introduced that tension those questions on your mind, and you can apply this in the center of that story, which is a nice arc to it. It doesn't fall flat it arcs up or you can open with tension you can open with a question. The itsy bitsy spider went up the waterspout. Down came the rain and washed the spider out what happens next well the sun comes out and the spider done did that thing you know what I mean? Like, that's now a story. And we've known this since we were children. And for some reason we get into the professional world, maybe because it's uncomfortable, maybe because we're scared of asking a guest to wade into that water, if we're an interviewer, maybe because you work for a corporation, and you're not sure that that level of emotion is warranted there. But stories need tension, they need a sense of drama, you have to open questions and people's minds before you can then resolve them before you can show them a better way before you can inspire change, or action or all these things we want, especially in the workplace where we're, you know, trying to build our businesses and leave our legacies. So for me, the more of a nose, you can have to root out what is broken, what is wrong, what's under explored what change is needed here. That's all the raw material, that's the carbon element, so to speak of, of storytelling, because again, without carbon, you don't have life. And so without tension, you don't have story.

Jay Clouse 15:56
After a quick break, Jay, and I dive deep into storytelling frameworks, and how to tell a good story right after this. Hey, welcome back to my conversation with Jay Acunzo. Before the break, Jay was just talking about the role of tension in storytelling. And I wanted to open up that door a little bit further, because he's using that word specifically, instead of the more common words like problem or conflict. So I asked him to go deeper in explaining how he thinks about the role of tension in storytelling.

Jay Acunzo 16:27
There's like three phases, I think of a storytellers career. So first, as you don't use any tension. And you know, in the in the marketing world, you write a lot of how to blog posts and tips and tricks and lists and things that you and I are very familiar with being content entrepreneurs in the digital age. And then you start to realize, Oh, I can use some tension. And so you insert a central question, or you kind of like agitate the peep the frustration people feel before then solving it. And it could be the same exact article, rather than say, everybody knows that a better podcast open, you know, Jay, you have strong opens to your episodes, everyone knows a better open to your podcast episodes means more people will likely listen and finish the episode, Here are six tips. For better opens, you might say something like, the most important thing about a podcast is how you start. Because how you start sets a tone for everything, but and there's that tiny little dollop of tension. Most of us don't do this, most of us open with this type of thing or that type of thing, or that now I'm agitating the pain, I'm bringing up the tension a little bit more. And so what can we do to open stronger, there's more tension, there's a question. Well, today, we're going to explore six things, right? So that's a very simple tweak, where it's a little bit more story style, it's not a narrative that you're creating. And that's the difference, right? I think a lot of times a narrative does have some kind of conflict or problem. But the way you communicate in in little bits can just have more tension, which makes it inherently more gripping, because people are wired to want closure. And the central technique to all this is called an open loop. So an open loop can be grand, like who will sit on the throne at the end of Game of Thrones, or it could be very, very tiny, which is just me inserting a pause when I speak, or saying yeah, I think you might be onto something Jay. But have you considered this other thing? Right? So that's like probably the tiniest form of an open loop. And so just the way we present information, the way we communicate, can grip people can bring out the emotions and can help people decide, oh, yeah, I'm gonna continue on this journey with this communicator and the storyteller, because I can't wait to see what happens next.

Jay Clouse 18:32
Okay, I want to take this opportunity to show a little bit of Jays storytelling handiwork in action, he was just talking about strong openings. So I pulled about 60 seconds of his three minute opening of a recent episode of unthinkable. The episode is called creative reps. And Jay starts by sharing a few quotes from famous writers and creators about their creative process. I'm going to let him pick it up from here, but I want you to listen for the open loops.

Jay Acunzo 18:58
Few things ever feel simple. It feels like a lot to reach the heights of those creators we admire who sit there saying it's actually really simple to make things that matter. I used to think, oh, that's because these people have some kind of special gifts. But then you do this work for a little while and you realize, Oh, right. The Muse isn't real. Creativity is practice. It's a craft. Those amazing creative people that we admire are the byproducts of their countless reps. And somewhere along the way, as they put in those reps, they realized that the most important thing to focus on are those simple things that add up. And maybe you and I can take that same approach each of us in our own work and apply it not to the distant project or career we hope to build, but to the very next Rep. So I'd asked you in creative work. What's a rep?

It's messy, it's complex, or is it ke ke ke keep it going. It's unthinkable stories of creative people who break from convention to make what matters most. I'm Jake Acunzo.

Jay Clouse 20:11
The two open loops here that stuck out to me were when he mentioned that these creators weren't born with something special and that the Muse isn't real. You immediately think, well, where does it come from then? And he closes that loop quickly saying that creativity is a practice. But the major open loop here is the question right before the theme music when he says, What's a rep? This is the central question he wants to explore in this episode, which you can tell by the title itself, creative reps, and he used the intro of the episode to lay out the reason why he wants to explore it. Okay, before we go back to the interview, we have to spend some time talking about one of the most common storytelling frameworks you'll ever hear about called the Hero's Journey. The Hero's Journey was made popular by a writer named Joseph Campbell. And if you look hard enough, you can see it at the heart of most popular stories. There are three acts in The Hero's Journey, each with five to six stages for a total of 17 steps. I really recommend digging into this when you have some time, but for the purposes of this episode, I'll try to hit the highlights. The three acts are departure, initiation and return. In the departure, the hero begins in a familiar situation and receives some sort of information that calls for them to head off into an unfamiliar situation. It's Frodo leaving the Shire to destroy the ring, it's Simba leaving Pride Rock. At first, the hero refuses to act but received some sort of help from a guide, Gandalf in Lord of the Rings. The guide helps the hero take his first steps into the unknown where the second act initiation begins. In initiation, the hero faces a lot of different challenges. They earn items and knowledge that help them with completing their quest. Through the initiation, the character gains a deeper understanding of themselves or the world in it prepares them for the final challenge, also called the ultimate boon. The ultimate boon is the goal of the journey itself. It's Frodo destroying the ring or Simba coming back to fight Scar. And once that is achieved, we reach Act Three, the return. Once the goal has been attained, the hero returns to their ordinary world where they can reintegrate and benefit society as a whole even becoming the guide for someone else. With this in mind, I asked Jay about his favorite storytelling frameworks.

Jay Acunzo 22:31
Right, I mean, you can point to the hero's journey. Dan Harmon, the showrunner behind community, and Rick and Morty. He has his own version called the story circle.

Dan Harmon
The so called story circle is my attempt to remove all of the hard and repeated work from the task of breaking a story, we do an eight step story process here, I call it an embryo, you've got a character that you can identify with, that has some kind of need wish, in completion causes them to go across a threshold where the story changes direction, they go down a road of trials, searching for something, they find it, whether they like it or not, it kind of kicks their ass, and they come back to the world they started in having changed, you need to go search for something, find it, take it and then return changed.

Jay Acunzo
Sometimes some of the best episodes, he will start in different places on the circle versus followed, like, you know, the first node and then around the circle, he goes. So the structure is profoundly useful, not only as a way to reset when things get away from you, and remind yourself, but also constraints breed creativity. I mean, every study on creativity shows that. And so these processes, these techniques and systems and models, they're all forms of constraint. I don't think I ever I never looked into Joseph Campbell's hero's journey. I never map a story to it. But I think I can sense when, you know, a good example is I created this episode of my show, Unthinkable, which is a narrative style podcast. And we were exploring this concept of the gap between people's taste like what you can envision creating and skills, what you can actually create. And there's a gap that's created. And Ira Glass made that very famous with his quote about the gap.

Ira Glass 24:11
All of us who do creative work, like you know, we get into it, and we get into it, because we have good taste. But it's like there's a gap, that for the first couple of years that you're making stuff. What you're making isn't so good, okay, it's not that great. It's trying to be good, it has ambition to good, but it's not quite that good. But your taste, the thing that got you into the game, your your taste is still killer. And your taste is good enough that you can tell that what you're making is kind of a disappointment to you. You know what I mean? A lot of people never get past that phase. A lot of people at that point they quit. And the thing I would just like say to you with all my heart is that most everybody I know who does interesting creative work. They went through a phase of yours, where they had really good taste, they could tell what they were making wasn't as good as they wanted it to be. They knew it felt short. It didn't have this special thing that we wanted it to have. And the thing I would say to you is, everybody goes through that. And for you to go through it, if you're going through right now, if you're just getting out of that phase, you got to know it's totally normal. And the most important possible thing you could do is do a lot of work.

Jay Acunzo 25:13
And the idea is, everyone faces this in their career. And the solution is to put in the reps, do a lot of work, ship, reflect and ship again, you know, arrive to the next wrap somehow improved. And I wanted to talk to six different creators in my membership group about how they experienced that. So everybody read their take on the quote, they read the quote, We splice it together, and kind of a chorus of voices. And then I had them answer some prompts to reflect on their experience of that, well, I had two or three people in a row and that edit, say, yeah, this quote deeply resonates with me. And then the fourth person I listened to this is before I cut it together, said, Does this quote resonate with me?

Speaker 2 25:50
All right, on to the questions. Does this quote resonate with you? And why? Kind of this quote, kind of resonates with me, but not really.

Jay Acunzo 26:02
And it My first reaction was to be like, so this person's not making the final cut. But then I was like, No, actually, it's important that we explore this from a well rounded point of view, it's important that we turn the problem over from different angles. And it's also important for the final experience, just the linear entertainment experience for a listener to get a person or two that completely agrees with the opening of that episode, and then get met with somebody who messes with that. And so I mentioned, I think there's different stages of storytelling. The first is no tension. The second is actually what we started with today, which is that central tension, I think the third is you mess with tension, like you ensure that people know, hey, I'm creating something that's an approximation of reality, reality is a total mess. And sometimes there's an answer, but most times, there's not an even what there when there is, it's bespoke. it's applicable in your context, but not in someone else's, or to different degrees. And so we're going to raise more questions than we actually answer in this experience. And you know, my storytelling idol Anthony Bourdain was a master at that messing with tension, there was not like a nice clean answer to everything he explored. And so having that voice, who actually was a dissenting view, from everyone else, saying, oh, the gap from Ira Glass, that quote resonates with me, to me, that was like an ability to say, you expect this to go in one direction. That's not true to reality for this to be a great story. But I call that phase three story. I have to mess with tension, I have to be comfortable getting uncomfortable and making you the listener uncomfortable to because that's real. And then I have to trust you to sit with that feeling. And try to make sense of it rather than spoon feed you an exact answer.

Jay Clouse 27:35
How have you continued to improve your own understanding and skill around storytelling, because you can read books about storytelling, but I almost get a sense like you are modeling and then shifting more so and I'd love to hear how you think about it.

Jay Acunzo 27:51
Yeah, I'm profoundly self taught. I'm bad at recommending books, and shows and things that, that study this and analyze this stuff. I like to study people that I admire people I don't understand and, and just try to make sense of what they do and mimic. You know, I think the humble way to say this is maybe maybe a synapse doesn't fire correctly in my brain where some people see their heroes and go, Wow, I could never, and I see my heroes and go, Wow, I want to try that. And I think the actual real version of that is I'm profoundly privileged. I'm a white sis male from the northeast of the United States born when I was born two wonderful parents. The door was ajar for me. And I had wonderful people saying, there's the door, here's how you push the door, here's what's on the other side of the door. And my hard work was doing that. But the door was ajar for me. And so maybe that's the reason I can look at someone and go, I'd like to try that versus sit on my hands and say I could never. But that's how I have learned over the years is like, I'm inspired by something. I want to understand how they did it. And then like, Is there a structure to it? Is there something underlying it, and then go try it. And that's evolved over the years to be a little more conscious. Like I mentioned, Bourdain, when I first started on thinkable. It was a show for the creative side of marketing. And then I talked to my listeners, and they were a lot of people were in marketing, but a lot weren't. There was something else tying them together. And it was this like journey element to understand creativity in the workplace, and answer big questions and tell stories about that stuff. There's some time thread throughout it all. So I need to find like a better structure than resembling a lot of marketing shows. So I sat with a notebook and tried to extract what Bourdain did underneath his episodes. And if he ever saw that, he'd probably say, this is not what we do at all. But I can at least approximate, here's this one episode. Here's the structure. I'm going to try using that and mold that with who I am, you know what I mean? And it'll be such a false sense of precision by doing that, that it'll inevitably be more me than him, but it'll give me some guardrails. And so I did that for a while. I call that an extraction, having no idea if anyone else out there does this stuff. I gave it a name, so I could teach it but and that was useful. So that's kind of how I learned it's like, study the people I like, try to understand is there a process underneath what they do? steal it, borrow it, reshape it, and then eventually leave it behind or break it as I find the next wave of the things I'm creating.

Jay Clouse 30:08
I love that. And I'm starting to see that it's a little bit of a pattern for a lot of the creators that I look up to as they follow a similar trend where it's not. It's not reading explicit instructional material, how to do this. They're just looking at their own heroes and modeling after it. I think it opens up a new, more profound sense of enjoyment for the types of things that you enjoy. Like right now, Mallory and I are watching the OSI, which I am not afraid to. And having having dabbled in one documentary project over the last few years. It just changes the way that I watch television and movies. And it's so funny. I think it probably drives me nuts all pause the screen and be like, Did you see that? Why did they do that? Why did they have that person go through the door at that moment? that hadn't been a conscious choice? But why why did that add

Jay Acunzo 30:50
you you're bringing up something that I struggle with all the time, I do the same thing with like documentaries, or we're listening to a podcast in the car. I bring up those like production considerations or curiosities to my wife. And she's the same thing. She's like, just watch it. And I remember a mentor of mine. His name is Andrew Davis. He's a wonderful writer, and speaker and storyteller. And you know, worked for Jim Henson's company and CBS. He knows his story. He knows production. And he said he cannot watch TV anymore, especially, you know, nonfiction, without analyzing it. And it destroys his ability to experience it and actually heard that from ESPN writer Buster only when I interned there. He's a wonderful baseball writer, and one of my heroes. And I remember asking him I was doing this series, when I was in ESPN, PR to promote the personalities through press releases and stories about the talent. And I got to interview Buster only it's like, oh, my God, it's amazing. humble guy, amazing human gave me recommendations for books to read about baseball for my thesis at the time in college, which was about the use of baseball in American literature. Awesome human. Exactly like his public persona, which I was encouraged by, they say don't meet your heroes. But if your heroes buster, only you should meet Buster only. And I remember asking him as part of the piece I was writing about him. You know, he grew up in Vermont, I think he was actually a Yankees fan. And I asked him like, how does your job change your perspective on this, and he goes, I'm not a fan of a team anymore. I'm a fan of the sport. So it's really hard for me to get like super geek level excited or put an individual up on a pedestal with a few rare exceptions, because I'm a fan of their craft. Right. I'm a fan of like, the things they're able to do and the stories about, you know, the stories about storytelling and the techniques about storytelling, and all those things like that's what I love. And so I love seeing a creative person show up as their best selves in their work, more so than I'm like every single person that we all expect a creative person to admire. Oh, they're amazing, right? Like, it's hard to be a fan of any individual. I love the collective. I love the craft, and I'm a fan of that.

Jay Clouse 32:51
When we come back, Jay, I dive deep into how he built his business as a creator. We talked about his start in podcasting, speaking in more, so stick around, and we'll be right back. Hey, welcome back. Jay began his business Unthinkable Media in 2015. With a background working at companies like Google, HubSpot, and even venture capital, Jay had a lot of opportunity in the corporate world. So I asked him what convinced him to venture into the unknown and pursue life as a creator.

Jay Acunzo 33:24
In 2014, or 15, I had a friend who worked for a nonprofit and in Boston, and their job was to connect the nonprofit world with the tech sector and you know, have knowledge tools and advisors flow from the for profit role to the nonprofit world. So they connected tech and nonprofits in Boston. And he sat down with me, we're talking about their content and content marketing and content strategy. And he was asking for my opinion. And I said, you know, you should host the podcast. And he goes, Oh, that's interesting. I'd never considered doing that. And I was like, Yeah, and I should host it. And he goes, Oh, have you? Have you ever hosted a podcast before? And I was like, here's the thing. No, but I was like, super excited to try and be looking for an excuse to it. Again, the synapse not firing in my brain being like, I like radio lab. Let me try that as an individual forgetting that radio lab as a whole team, like, not a rational thought. And so I tried, you know, I tried a narrative style show, did three episodes, learned a lot. Looking back on it. I sound profoundly bored. I hadn't found my voice on the microphone. You know, in the moment I sounded, I thought I sounded professional. And I'm planning it back. Nope. But I tried three different episodes. And my friend left the nonprofit and they shuttered the show. But by then I had enough momentum, and I had a taste. And so I pitched my bosses to do a show. For their firm. I'd worked for a VC firm at the time. And that show kind of unleashed me creatively. Because they they said, Yeah, and it's all you it's, you know, you do it, go. And so I built this podcast called Traction, which is creative and clever stories of how startups start. From NextView ventures, I'm Jay Acunzo, and you're listening to our brand new podcast Traction, or at least you would be if we actually launched in. So congrats, you're clearly someone who gets their hands on the earliest versions of things. And actually, we wouldn't expect anything else, from anyone listening to this show. That's because Traction is going to be about the creative and unusual things that entrepreneurs do to scrap their way towards initial traction in an important area of their business. We've all heard that as a startup, you have to do things that don't scale. Well, what are those things? This podcast will explore those stories by talking to founders, executives, investors, and journalists, all of whom did something clever, scrappy, atypical, or downright brilliant, to get started doing pretty much anything. And we got a ton of press, and it wasn't based on our reach, we had very few episodes, I think like Episode 13. I remember, Fortune magazine wrote about us. And they ranked us among all these competitors with like, hundreds of episodes. And it was because we'd really developed the show, we figured out a premise that was different and refreshing. We figured out a format to the episode, again, that structuring those constraints, the storytelling arc to it. And then we did some, you know, creative wrinkles on it. Like I did some music and some narration and some some sound design. And I was like, Oh, that's it. That's what this takes. So I launched unthinkable right at the same time, because I was like, well, I want one that's mine, that I control. There are no stakes, because I want to tinker more than the day job will probably let me do. And I wouldn't feel right, testing it on turf that I you know, want results for at least I want to respect the fact that my bosses are giving me this creative freedom here at the firm and unthinkable started to get some inbound requests for me to do things like public speaking, making shows for brands, which I'd never considered doing before. And so I booked a couple paid speeches, I had a couple inquiries to make shows, I was starting to make a little money. And at that point, I was like, I need more time. And so I was ready to go at that point, like a year into this process. And I guess what I'm trying to convey, Jay is, there's a lore of the entrepreneur that you have to leave with two feet. And it's super risky. I worked for a venture firm, we invested in like 55 companies, by the time I left these entrepreneurs, they're taking some risks, for sure. But when you hear them explain their business ideas and product, it's inevitable in their minds, it's logical, they're made, and they're also mitigating the risks through testing, you know, through getting some traction, etc. So that's what I decided to do, I'm not going to build a SaaS product, but I would mitigate the risk, get some actual revenue, get some traction, some strong signal from a few people saying they love what I do, as a way to ease out the door and instead of leap, and ever since then, I've been teaching and or making shows for brands, authors, you know, etc. And my own as well, I don't think double, I think kind of carries the whole body of work. It's like the biggest flag that I planted.

Jay Clouse 37:46
Well, hold on, let me let me go back a step where you said, you're doing unthinkable and you're starting to get requests for public speaking and hosting shows. Those are huge wins. You know, if I'm an independent creator, making something to get that type of inbound attention that is, theoretically also offering to pay me to do something that's amazing. Yeah, what what really led to those opportunities? Was the show growing a lot. Did you start to build relationships from guests on the show? How did that happen?

Jay Acunzo 38:11
Sure. I mean, everything's connected to everything, right. So to actually explain it have to take you back all the way to the beginning. But there's all these dots I can might put down that are a little bit more vividly colored in on the map, like one such dot was, for two and a half years, I built a community group in Boston, called Boston content. And it was like, I found myself in this role called content marketing, had never heard of it before found myself doing something that resembled journalism and an editorial work, but was given a different name. So I built with a woman named Arestia Rosenberg, this Meetup group, and it started as drinks. And then we had meetups that look a little bit more like events. And then we had actual events, and then a website and kind of grew and grew. And, you know, that led to some free speaking gigs. And so as people saw me more, and I collected the community more and provided a platform, that community, you know, it was kind of like it showed me the power of raising your hand and being like, something's broken. And I don't have the answers, but let's go figure it out together. Like there's a jungle in front of us. I'm going to hack away at the jungle, I have a machete but I want to, I want you to have one to like, Come hack away with me. And if you tell me we should go, right, let's listen to that. You know, there's a lot of people who have public personas that they're doling out answers. It's like, I have an answer. Here it is. So now I'm smart. take me seriously. And I had way more questions. And that's just how I approach all my work today. So the community group led to some free speaking engagements, and a little bit of a bigger network outside of, you know, the the tech sector, which in and of itself, being in VC, you have a bit of a public platform. And so I parlayed that into just public teaching for free. I guess what I'm trying to say is, I was a participant before I had anything to promote. All of a sudden, people started asking me for stuff and I was like, oh, how can I get proactive about this instead of reactive? right around the time that I started on thinkable? A friend of mine was starting an agency to help manage public speakers. And I was like, he's like, I need a guinea pig and very similar to the nonprofit friend of mine who with the podcast, I was like, I'm over here, but I can do it. Yeah, why not? And so he kind of showed me the ropes. This is Andrew Davis, he showed me the ropes of public speaking. So now you parlay this mess together, Jay, try to give you a clean answer. You have a community group that I built, where I'm just trying to help other people and also grow myself, you have a side project show that was drafting off the back of like this day job show, but was more ambitious and Messier and more experimental. And then you have a friend of mine, who had a need, and I was willing to help him with that need. And I guess, like, taken together, that led to like the first person saying, we'd like to pay you a small fee to come and speak because we've seen you do some other stuff like that. That led to a CEO of a tech company coming on unthinkable, having a good experience, liking the final edit, seeing what I could offer me proving it and then saying, could you make a show for us? Like it's it's all kind of very messy, and hard to explain in in pithy fashion. I don't know if like one sign can be put over the top of this was his side projects or help others first, but maybe there's some themes in there like that?

Jay Clouse 41:07
Yeah, I think I think it's a little bit of both, right? I've seen that recipe play out in different ways, like the obvious giving first and building relationships that's going to serve you some were somehow down the road no matter what, but I think it is that magic combination moment of, Okay, I'm gonna hang up my shingle and make my own thing. Because then the people who had this goodwill for you who wanted to support you have something to tie that to and say, oh, maybe maybe Jay is available to take on new creative project, because he's doing things on his own. Now, I think there is something to that. As you progressed as a speaker, I would love to hear more about that experience, because a lot of people see speakers and I think I might be able to do that. But it seems profoundly harder than I think we realized from from the seats. So talk to me about what makes a good talk or a good speaker.

Jay Acunzo 41:52
Yeah, I think the way you approach your work really matters. This affects speaking, I think most potently, and keynotes to not bring you know, breakout is kind of a solution lead talk, you're up against lots of others at an event. And someone is self selecting that. Yes, I'd like to hear Jay talk about podcasting, because I am already thinking about a podcast. But a keynote is for the whole event. A keynote is something where you have to deliver something that has high impact helps you think and execute better, but it's not listing out steps to take, because it's a problem led speech instead. Right? I'm trying to help you, you we all agree we have the problem. Right? Right. Great. We're all in a room together. All right, well, let's go on this little journey together to see this work differently. So it's not a how to speech. It's a how to think speech. But you can also frame your work is how to think work. And the same person I've mentioned before Andrew Davis showed me the power of that, where instead of trying to be an expert, being an investigator, asked questions that endures words Google can't answer. And then you go on a journey and invite others with you to try and figure that out. So with Unthinkable, for example, the first question was, Why is there so much commodity content out there? We don't aspire to be average. But we're shipping a lot of average stuff. What's the culprit? Oh, oh, best practices seem to actually be the culprit. That's like 25 episodes into the show, we realize that, well, what's the problem with best practices? Let's go tell some more stories and talk to some more people. Okay, it's these things like we're trying to diagnose this illness. Here. Again, the analogy being today is broken, something isn't sitting well with us. Tomorrow looks maybe like that. That's the mountain peak. How do we get there? I have no idea. Because there's a jungle between us. So let's hack between where we're at where we'd like to go. Come with me, join me on this journey. Well, keynote is like a perfect summary of that journey. So for, I don't know how many episodes, I'm playing that out in long form, with unthinkable and also the associated newsletter, both of those projects are still running, because that's how I frame the work, tackle a problem go exploring. And the keynote is like this really tiny summary of that journey with the best of the best stories, the best of the best insights. And hopefully, the more I refine, and iterate and refine, again, these ideas, some kind of contextual model. It's like we are trapped. We are stuck in this endless cycle. All of these best practices are just part of this constant pattern in our work. They're all just spokes on this ever spinning wheel. First one is on top, then another and on and on this wheel spins. And this wheel leads straight to the one place we don't want our companies and careers to be average. We can cling to the convention and get crushed as the wheel turns. So we can keep reaching out to every new trend in our work, but never really firmly grasp anything in our careers. But if we let go that wheel can spin into total chaos. Are we doomed to this endless cycle? I say no, I say we need to break this wheel and think for ourselves. Like if you're trying to execute on this, here's how to think about it. You know the famous one Simon cynics golden circles. That's a contextual model. All these six questions you can ask in succession to do X, Y, or Z. That's a contextual model. So that's what you're doing. You're asking questions, investigating, telling stories, and then you're getting up on a stage. And you're trying to package this like pretty long form journey into something that's really potent. It's like, you know, I'm Italian. So it comes back to food with me. It's like when you cook a sauce, you're distilling it down, you're letting it cook for hours on end, and then you're giving them the best version of that sauce. But the whole while it was a lot of trial and error, a lot of like, let me toss this in and taste it. Let me let this cook for a little while, like, I don't know, let's try that for once. So framing your work as an investigator instead of an expert, is not only a great way to lead, but it's a great way to inform this like prolific body of work, from a keynote speech to a show to a newsletter, anything that is like enrollment or subscription based, and is meant to really profoundly change people.

Jay Clouse 45:53
I'm in. I'm on board for all of this. I'm Invisalign of thinking, I immediately go to, but what about my own capacity.

Jay Acunzo 46:01
There's a tension right there, well done.

Jay Clouse 46:02
I'm in exactly, in awe of how prolific you are in creating these very story rich production rich shows, previous keynote speeches. But it seems like you could explore endlessly and not actually create anything. So how do you tow that line?

Jay Acunzo 46:23
it for me, it all comes back to writing my newsletter, and I'll break that up into it comes back to writing space, my newsletter. So writing is the engine. writing to me is not an act of sharing what I understand. It's an it's the act of me trying to understand. And so every Friday, I'm like, you know, I know what we're exploring right now we're exploring this idea of the next Rep. We all want big, thriving bodies of work and smash hit projects and all this stuff. We want to close that gap from Ira Glass between what we imagine creating what we can actually create. Well, how do we do that? Well, according to that quote, and I agree, we have to put out a lot of work. It's practice, it's reps repetition, plus reinvention over time, do a thing, do it better keep going. Alright, well, if you really distill it down to its atomic unit, all this stuff is just the summary of lots of little reps. Great. So what do amazing creators do to get to the next rep somehow improved? Is there a process? Is it way too bespoke? to even try to put a formula or technique to I don't know, I have more questions at this point. I'm really early in the next rep investigation. So every week on my newsletter, I'm writing to understand something, I observe something and I'm trying to interpret that it's a metaphor or an anecdote through the lens of that investigation, or I learned something. And I think it does apply, and I'd like to share it here. The newsletters my perspective than the podcast, is others perspectives. It's taking themes that sometimes were from the newsletter, because I got replies as signal. Oh, I should expand this to a whole episode. But sometimes it's just me using my taste to say I think this is worth exploring, perhaps, or it's a big burning question. And so I'm going to go find others to come on the show. And you know, ask them questions, tell their stories, and true to form with the docu style, anything, there's like two types of external voices that I have a guide who can analyze what's happening, give us the why give us the academic view, a guide and a local, someone who embodies the thing we're exploring, they're living it out day to day, you know, in travel journalism, it's the local journalist, or you know, the person who emigrated or immigrated, and they're like, able to interpret what Mexico is all about. And then you go talk to the cab driver, the guide and the local. Sounds like a lot, right? But I have I have that approach to it. But it all starts with just the newsletter, I'm frustrated by something, I gotta write about it. And the more I do, the more I find the focus and find the ideas, and then think, oh okay, this leads to this leads to this. So if you have that one project, which is consistent, you ship it once a week, completely your own, there's no other stakeholder. And the only goal is not the audience you achieve, it's not the money you make. It's just your exploration or investigation of something that frustrates you or you're questioning that little project tends to lead to all this other stuff that if I sound like I'm clear on my work, was not the case at first, if not for that project.

Jay Clouse 49:17
Well, here's the tension. And I think a lot of listeners of this show will identify with, I buy into everything you're saying here. The best practices are what we see as getting the fastest result. And we want fast results. You know, this is something that I'm struggling with internally a lot lately, which which, you know, is you know, do I want to be super specific. So I give a very clear signal. This is why you follow my work, or do I want to be more true to me and make something I think is more interesting and more long term better, but seems like a trade off is slower accrual of people paying attention. How do you think about that?

Jay Acunzo 49:56
Yeah, I don't know if I do. We talked about having a flair for the dramatic or at least believer intention that story. Like the way I'd interpret my work like if you if you drew a circle, and that's my body of work. And then you put on all these dots, those are all like projects and random things that I'm doing and saying and trying. Occasionally, there's like a bright, single colored line. Here's a blue line connecting a bunch of dots. That's like an investigation that I'm on. Sometimes it's really short, because I feel like it leads nowhere, or I lose interest. But sometimes that lasts two and a half years, which was the case for early Unthinkable, which led to my first book. And then I felt lost again. And now I feel found again, because I'm like, Oh, I have this through line. So I don't know if I stopped to wonder, Well, if I was just the podcast guy, by became known as like, if you want to make a b2b podcast, it's Jay, would things happen faster or better for me, I mean, occasionally that crops up. But it only crops up when I'm not making stuff. It crops up when I'm like, struggling to get to the next thing where I'm trying to overthink the next draft and try to make it great, instead of like, slap down a messy lump of clay and shape it and put down a bad draft. When I start to overthink things, that's when those thoughts might crop up. And so to me, it's like creativity is for solving problems. And I'd like to help others make what matters most. That's my, like shining North Star. And how do I do that? Well, that part's gonna change. And so what am i frustrated by? Well, I can't stand how so many people are so disappointed in their work, that they stop shipping, or they feel stagnant. And so how do I help them? There's enough knowledge and ideas about how to start. But what about when you're, you've shipped something and you're like, it's not it? Or it's not happening fast enough? And maybe that's part of it. Maybe actually, the reason I don't stop to think about this is is that is the problem I'm trying to solve right?

Jay Clouse 51:46
You just mentioned your book. And that is a larger scale creative project. Sure, it took longer than your typical weekly newsletter, with all of the constraints that you have of consistent creation. How did you bucket time for that book? How would you now in 2021, bucket time for a larger creative project? If you wanted to do that? Where would you find it?

Jay Acunzo 52:08
When discussing your writing of your book as an author, what I realize is you're supposed to say it was such a slog, it was so hard. I hated writing the book. I love writing. I mean, I also was a cross country runner in high school. So here I am a student. And I love the punishments that both teachers and coaches dole out. You're going to write an essay about this until you learn your lesson. Great. You're going to go first, you're going to run laps, and fantastic. Like I ran cross country, I chose to the sport, the thing I did was the thing that like the football coach, or actually I play basketball. So the basketball coach would use to punish us, and I'd be coasting. I'd be like doo doo doo doo doo, because I pushed myself on cross country season. And now this basketball running is easy, right? So maybe I'm a masochist. Maybe that's my answer. But I love writing.

I love the process of it. I love how it makes it feel. Makes me feel and I get to make others feel. So every Thursday, I lived in Queens at the time, I would first go to this coffee shop and I'd sit this is what I'd call my golfers waggle. You know how golfers have the same little little motion heading into their swing?

Jay Clouse 53:14
Bowlers too.

Jay Acunzo 53:14
Yeah, bowlers. I mean, you know, baseball, wait, when you're up at the plate, or when you're at the free throw line of basketball, like, you know, I wasn't athletes, I think about this stuff, and I want to read sports, I would walk to the same coffee shop, I was always the first one there, it was down the street from me is very easy to do had no kids at the time, and would get the same drinks at the same chair. And at first it was just organizing all this history in my show all these stories, and then my newsletter. So what I didn't realize at the time was I had i'd sat upon this goldmine of ideas and content in my newsletter in my show that could inform the book. So that gave it a spine. And then I needed to flesh things out the stories in my show that weren't investigated, I needed more investigation. In other words, to flesh out for a book, the ideas in my newsletter that were gut reactions to things but I had to gut check now against the science, for example. So I have the spine rather easily. And then I would explore an outline the rest of that stuff. And then as the outlining finished, it moved to drafting. And so again, every Thursday in the morning, I'm doing that every single week, for however many months it took. And then I realized I needed more time. So no problem. I'm going to tack on a little bit more here or there or there. And the whole key to this was I had to trade off the projects that felt urgent, but actually weren't. I pretty much disappeared from Twitter at the time. I'm really active on Twitter right now. But I had to get rid of it for a time. I pretty much was not able to watch any sports, I pretty much was not able to watch Netflix. So I had to make that trade off. But I let the desire to write a book lead, like the dopamine hit that I got was greater than tweeting, and I'm incapable of doing something that isn't intrinsically motivating. So my trick if there is one is to somehow try I'm convinced myself, or maybe short circuit, the reward parts of these things that oh, this is actually what I want to do more than the other stuff.

Love that. Where do you think you're going? You know, we obviously had a big year of keynote speeches in person going away. But that's probably reopening. So how do you think about your next steps entering 2021, 2022 and beyond.

We draw so much meaning from our work. And yet the content about career in business is so lacking. I mean, back to telling stories with tension, it's flat, or it's shouty, or we're talking about Facebook, Apple, Amazon and Google yet again, or, you know, it's it's trying to out expert, the other million experts, like we need more explorers, we need more investigators who are asking important questions, and then they go on a journey. And I'd like to be one of those people. I don't think I'm ever going to be the individual doing that. But maybe I can inspire a small halo around me, because I speak to other creators to do the same. And to me, that's having an impact. So where I go from here is I'm looking for progressively more sustainable ways to tell stories to make things like unthinkable, the thing I do, instead of the side project or the vehicle to sell a course, for example. And if I can do that, I know I'll be fulfilled. Let's be serious creative work is in some ways, selfish, but I also see it as very generous as trying to help other people and make things that make a difference. And oh, my god Bourdain did that. And so if I can bring even a modicum of that to the workplace, you know, I will look back on a career and feel very fulfilled by that.

Jay Clouse 56:45
I don't know about you, but I aspire to be as thoughtful, clear and articulate as Jay Acunzo. Our time together here really flew by because it was just so easy to lean in and listen to what Jay was sharing. There's a certain magic that comes with being a great speaker and storyteller. If you like this episode, you will certainly like Jay's podcast Unthinkable which you can find in this very same podcast player. You can also follow Jays creative exploration of the next rep by subscribing to his newsletter Playing Favorites. links to both are in the show notes. Thanks to Jay for being on the show. Thank you to Emily Clouse for making the artwork this episode. Thanks to Nathan Todhunter for mixing the show and Brian Skeel for creating our music. If you liked this episode, you can tweet me @JayClouse and let me know if you really want to say thank you. Please leave a review on Apple podcasts. Thanks for listening, and I'll talk to you next week.