Jay: Well, I’m sitting on a barrel of TNT in this room, and I have a coyote outside the door with a plunger, so – heck yes.

John: Jay makes stuff to help makers. He’s most known as host and creator of Unthinkable: the podcast that shares the eye-opening stories of craft and creativity in business. He’s an ex-Googler, ex-startupper, and current VP of content at NextView, a seed-stage VC firm in Boston and NYC. Jay, take a minute, fill in some gaps from that intro, and give us just a little glimpse of your personal life.

Jay: Yeah, sounds good. So, I – that entirely sums up my career. I like to make stuff for other makers. I’ll give you a really quick story that I think will help people understand where I’m coming from and maybe relate to me a little bit. So, I started my career at Google, like you mentioned, and one day someone sent me a YouTube video. Now, this is a big deal because this video was “Kid President.” I don’t know if anyone listening has heard that, J.L.D., you familiar with “Kid President”? Amazing, right?

I love this video so much, and I ran home that day, and I showed it my friends, and I was – I was hyping it to them. I was selling it as the greatest video that they’d ever seen in their lives, and right at the height of their anticipation – they saw a pre-roll ad – and I was like “egg all over my face”, “Oh, wait. Okay, well, I promise what I was promising you – the great experience, the great video, will happen in 30 seconds. Just – just wait for it.”

And – and I just felt like an ass because I’d promised my friend – friends something they wanted, something amazing, and I got not that at all. I got a frustrating experience. However, the first thought in my head was “Damnit, Eric.” So, why did I think “Damnit, Eric” when I saw the pre-roll ad? Well, because Eric was my colleague at Google who had sold the YouTube campaign to this particular advertiser and I recognized it as his client, and I thought, “Damnit, Eric.” And then the worst thought of my career hit me like a ton of bricks, which was, “Wait a second. I have the same job at Google that Eric has.”

So, that means someone somewhere was cursing the name of the person responsible for a terrible experience in their day, and that person didn’t know it, but I was responsible for that frustration they were feeling. And so, I quit. I’d been thinking about leaving going to a startup and building something people actually want, but I quit because I – I was just sick of trying to force people into wanting stuff, and I wanted to make people actually – or make stuff people actually wanted. So, that was a big moment in my career, and hopefully that story – I think a lot of people – a lot of entrepreneurs can relate to that sentiment.

John: Yeah, I love that. I just love when people actually find their gift, and then find a way to infuse passion into that gift, and go forward with that. And Jay, that kinda sounds like the route that you took. You had to – do your thing. You had actually to live in the world, and work, and grow experience to find out what those pinpoints were that you wanted to serve. But you did, and now here you are today, and speaking of today, you’re the current VP of content at NextView. So, let’s get specific. Within that role, and within whatever you have going on else in your life, how do you generate revenue for your business for yourself?

Jay: Yeah, sure. I’ll give listeners a really quick look at the NextView thing really, really briefly, and then I’ll talk about revenue on Unthinkable. So, as VP of Content, really the name of the job is “Platform”, but I didn’t use that because no one knows what the hell that means outside of VC. But it’s this massive trend that I was fortunate to be really early on here at NextView. Basically, Platform is supporting startups and entrepreneurs in ways that stem beyond capital, and advice.

So, as a seed fund, we’re all about traction. Our capital helps you with that. Our advice helps you with that. Our intros – so I create a ton of content: our podcast, our blog, and resources, and more. Most of it’s public, some of it’s for our portfolio only but it’s all around that same idea. Whatever you’re going through, you’re going from zero to one at the seed stage. So how can we create systematic programs to help startups gain initial traction? And the good news is, lots of firms have started hiring a similar role.

I was very early – I think I had three or four conversations when I started at NextView with my peers. Now it’s a massive trend. That’s a beautiful world for entrepreneurs, I think because now you have all these VC’s trying to out-help each other, instead of out-chess-beat each other, and so, the entrepreneur wins. I love, love, love that.

John: Now, are you a personal investor in any of these companies that are startups?

Jay: No, I’m not. Someday, maybe. But right now I actually don’t have aspirations to move over to the partner track, or do any investments. I love to create. I love what I do day-to-day, and I love building my – my company on the side. So, it’s given me all the joy in the world. So, I’m not looking to stray from that.

John: Yeah, very cool. I remember I – for a while, Tim Ferriss was doing a lot of angel investing and doing that such, and he just found that it was – it got too much for him. He had to step back from the table for a while and reevaluate how he wanted to proceed – if he does even want to. So, it is a different game once you put your money, and it’s involved, and then you start getting all that information.

So, definitely something you wanna be thinking about, Fire Nation. If you – wanna learn more, go down that road, it’s an interesting road. A lot of opportunities and not just injecting your money into companies – Jay has another opportunity that he does that’s completely different, but just fulfills him in a powerful way. Now, Jay, let’s talk about your journey as an entrepreneur to date. You’ve had the ups and the downs. Let’s talk about the lowest of the low. Take us to your worst entrepreneurial moment, and tell us that story.

Jay: I’ll go back to another startup – we were about a Series A startup as this past company – and – I was preparing this big presentation to my team, and as head of the team I was trying to both inspire, and inform them, and I’ll walk you through why I think I did neither. So, I thought I had this big, unique insight, and – I was wrong. Basically, I was trying to figure out our reader behavior.

We were a media startup, just like Unthinkable. My – my current side business is a – is a content brand. It was a media startup I was working for, and I was trying to get – more insight to my team about what it takes to get a loyal reader to the site. Not just clicks, and page views, and all that stuff. But how do you get depth of a relationship with a reader?

So, I dove into Google Analytics, and I was looking at time on site, and repeat visitors, and I was looking at our subscriber data separately from that – and I found this chart in – in ana – Google Analytics that basically broke down visitors by number of times they came to the site. So – so, picture two axis: the vert – the vertical was like number of times you visited (1, 2, 3, etc.), and then the horizontal was the number of people that had visited the site that many times.

So, you had all these blue bars running horizontally out of the numbers of times people visited. And I thought I had found this golden insight because when the vertical axis went from nine visits, to ten to 15 – it was one bucket, ten to 15 visitors – the bar got huge, and I was like, “Aha! Lots of people who visit more than ten times become super loyal. Look at all these people. There’s a dearth of people in the seven/ eight/ nine visit range, but all the sudden it jumps when it hits ten to 15.”

And I was like, “Guys, we have to optimize everything we do – to get people to visit our site ten times because look at this. This triggers this awesome behavior!” Well, here’s what was wrong with that. Google Analytics showed one visit, two visit, three visit, all the way through nine visit as separate entities, but then they grouped together ten through 15 as one bar.

So, it wasn’t this magical tipping point. It just showed you an aggregate of six different numbers! And as soon as I presented it to the team, I knew it was wrong. As soon as the words were coming out of my mouth, I was – presenting it with total confidence, and really excited, and –

John: So, it dawned upon you during your presentation?

Jay: Oh, my god, yeah. So, here’s my lesson from that. First, practice your presentation, especially if it’s a big one. But really, second and more so, bet on your strengths. So, I am not a very data driven Quant type guy. I’m really good at the Qual, I’m very good at understanding people, and users, and – and experience, and content, and story – things that people love. But I’m pretty bad at trying to dive way deep into the data and parse meaning, and – and I’m much better at hiring to compliment that skill, than I am trying to fake it.

So, that was just – I felt like such an idiot. I sat down afterwards, and I was just red in the face, and oh, my god – thank god the CEO went right after me because he’s a – was a loud guy. He could take some of the attention away from me, but – oh, man.

John: I hear ya, and that’s kinda the one thing, Fire Nation, I do want to – latch onto, with what Jay said is: he should’ve been focusing on his strengths, and that’s what we as entrepreneurs need to realize, is say, “Hey, let me sit down, and actually figure out what I’m good at, what I’m excited about, what I’m passionate by.” Because if I’m good at something, and I’m also excited, and impassioned about it, then guess what? I’m probably going to be pretty good at it. And if I could be pretty good, to great, to amazing? That’s what the world needs.

The world doesn’t need an Okay Quant guy. Jay was an Okay Quant guy, and then he made that mistake. That’s just never gonna go. So, you gotta find people to fill in your spaces where you’re just not good, and you focus on your greatness; amplify that. Now, Jay, that gave you an “aha” moment of epic proportions, so to speak. But you’ve had a lot of those. So take us to one of your greatest “aha” moments to date, and tell us that story.

Jay: So, I’d gone to work for a big company, and I really didn’t enjoy it – not because of the company necessarily, but because I just realized that big companies aren’t for me. And when I left that company I launched a personal blog as I was figuring out what was next for me – this is before I joined NextView. And I named my blog Sorry for Marketing because I had been in marketing technology companies my whole career, and I just wanted to be completely and brutally honest about how I was feeling.

So, the posts I wrote there spoke to this idea of “There’s a better way to do marketing. You can be audience first, and content first, and story first.” But I was just completely and brutally honest in everything about that side blog, and it was the fifth or sixth side blog I’d ever launched, and it was the first one ever that actually started to gain audience, and get subscribers, and get shares, and get me featured in other places. And I was like, “Oh, my god. I need to pursue this feeling of just being completely and brutally honest in my work because it’s actually resonating with other people.”

It’s not so scary once you start to do that, and good things started happening. I got invitations to speak, and to guest write. I started doing this on Snapchat, and I was just goofy, and honest, and myself, and – my strategy’s just to have fun, and just be a person, and people want to hear me say there’s some kind of deeper strategy, and I’m looking for an ROI, but really I’m just trying to be myself more and more of my projects.

And then, with Unthinkable, this – this content brand that I have, it’s this huge, bright, loud, flare gun of honesty from me to the world, and it’s gotten more depth of reaction, and – and also breadth than anything I’ve ever launched. And so, this “aha” moment really came from just me saying to the world on my personal blog what I thought about the marketing industry and my own career in it, and good things started to happen.

John: What I think is so important about this message, Jay, that you’re sharing right now is that we have to find our voice as entrepreneurs. And it wasn’t just like Jay could’ve been, “Oh, my gosh. I wish I would have realized this a year ago, or two years ago, or the first blog that I did.” It’s just not like that. It’s not that easy – it’s not just like you can just say, “Okay, I’m going to start now, and just be me, and just be my voice.” It takes time. Jay had to go through struggling to find his voice, to actually find his voice.

Now, of course, it’s going to come a lot quicker when you can just put aside all of those things that we have: that Imposter Syndrome in our head that’s just saying, “who are you to write these words or create this podcast”, and just say, “Hey – I’m going to be me.” So, just know these things, Fire Nation. This is what I want you to really be taking away from what Jay is sharing.

No. 1: you wanna find your voice. But No. 2: know it’s going to take time, it’s take a struggle, but you will get there, but you gotta keep doing the thing to move towards finding your voice. And No. 3: it’s gonna – you’re gonna get there a lot quicker if you’re just you. If you’re just open, honest, transparent, goofy, whoever – whatever is it that you are. If you’re serious, just be serious. Whatever it is that you are – be yourself.

Because whether it’s writing, whether it’s audio, whether it’s video – we as humans can just understand and recognize authenticity, and that’s what we want in this world. So, Jay, that’s my big takeaway, brother. What do you want to make sure Fire Nation gets from your story?

Jay: I – I just think that when you – it’s so wonderful that we can measure, and document, and share everything in this world because we can get better information more quickly. But, that doesn’t mean you should try to imitate or become some idea of success. Because when you try to attack what looks like success, or what other people say is success, you very rarely get it yourself. And even if you do, it’s gonna feel a lot more hollow. So, for me, yes, find your voice. Yes, it’s – it’s difficult, especially when you’re writing or doing creative work like I am.

But, honestly, think about it as a body of work trumping any one project that you do. You need to figure out – yeah, the voice, and my – my calling is for me making stuff for other makers, but all that doesn’t matter. What matters is that I’m trying to build myself a body of work. Because the more you ship your work, the more you find your voice, the more you start to get subscribers. All the things you want as byproducts, as signal that you’re doing a good job creating a body of work, the more that stuff happens. So, that’s the big thing is – is ship a lot of work.

John: The more you ship your work, the quicker you’ll find your voice. That is so true, Fire Nation. Now, Jay, what’s your biggest weakness as an entrepreneur?

Jay: I think I’m pretty bad at – and I learned this through two big company stops: I – I’m bad at running a repeatable machine. I could maybe get good at it, but I dislike it a lot. I’m really good at building it, I’m – I’m really good at saying, “I don’t know what the machine will be, but let me spin up a couple of cogs, and cranks, and test it out.” But once it’s up and running, I suck at saying, “Well, this is now my gear to spin, and I just need to figure out a more efficient way to spin it”, because I get bored, or I get frustrated, or I start chasing the shiny. So, I’m more of a builder than I am a maintainer, I guess.

John: What’s your biggest strength?

Jay: So, I’ve been in this content world for a little while now, and I’ve noticed a lot of people like to take shortcuts, and hollow out the stuff inside the content. I’m really good at that part. I think the way I sum it up is, I’m really, really good at something both nutritious and delicious – in a world where people err on one side or the other.

If you’re a business blogger, for example. It’s smart information. Great – but it sucks to read. Or you’re BuzzFeed, it’s fun to read. Great – but it’s worthless information. I’m really good at marrying the two and producing work that add – adds actual value to you but is a delight to consume at the same time. So, nutritious and delicious content, I think, is – is my big strength.

John: I love that phrase. “Nutritious and delicious.” And now, Jay, you have a lot of things going on that you’re excited about. We actually met in person at last year’s Content Marketing World, and just your energy, your passion – it’s contagious. So, what are you fired up about right now, today?

Jay: I’m fired up about this huge, I think, inflection point in my career. But something I’ve been working on for a few months – it’s finally coming to fruition. I call it the Content IP, or Intellectual Property, behind making Unthinkable, my show. So, we took this hiatus, and we’re actually at the time where you and I are speaking now – in the middle of the hiatus – we come back end of August.

But Content IP – think of it as a rundown of how do you write a show consistently. The Daily Show has this. Sitcoms have this. This American Life (the podcast) has this. But – I have now this framework for building a – a repeatable process and a show that doesn’t feel wrote. It helps me be more creative. It helps me sprint faster and experiment and improve quality of product. And to me, it’s unbelievable that the speed and the quality were both enabled with coming up with this rundown.

So I call it the – the Content IP. It’s – if I get hit by a bus, somebody could step in, and hopefully build a really good show in my stead. Or if I want to bring in someone to cohost, or replace me someday, or whatever, but – it’s getting beyond just intuition as the driver of a good episode for Unthinkable, and getting to the spine of what makes a good episode every single week.

John: Fire Nation, speaking of good episodes, we have some good content coming up in the Lightning Round. So, don’t go anywhere. But we’re gonna take a quick minute first to thank our sponsors.

Jay, are you prepared for the Lightning Rounds?

Jay: Let’s do it, man!

John: What was holding you back from becoming an entrepreneur?

Jay: I don’t really wanna build what the sexy startup world seems to be today. Even though I work in tech VC, I don’t really wanna build a software company. It took me a while to come to terms with that. I like content. I like media. I like story, and creativity, and – and being an entrepreneur in that is – is super murky. I think – it’s always murky in every entrepreneurial endeavor.

But more so than, I think, building software, is this idea of “How do you build the life when all you wanna do is create interesting content for others?” So, that held me back for a long time, and it feels liberating, honestly, to get over that.

John: What’s the best advice you’re ever received?

Jay: The caveat is: the easiest way to improve your writing is to write more. But beyond that – read everything that you’re writing softly out loud to yourself. You’ll be amazed at what you find. Your writing will get so much better. Read what you’re writing very softly out loud, and you’ll become a great writer.

John: I do that every time when I read my emails, and whenever I do that, I always catch something that – sounds funny, or is just spelled wrong, or just isn’t right. So, it is key, Fire Nation. I love that advice. What’s a personal habit that contributes to your success?

Jay: So, I tried this recently over the summer, and it’s starting to work for me. But it’s focusing on the one most important thing – in a small list of priorities. So, I prioritize family, fitness, Unthinkable, and NextView. And then, I have one big goal for each: the most important thing. So, for instance, with family: no phone during dinner. With Unthinkable: hitting a target time for scripting an episode.

These are small and attainable, and the goal is to keep changing them and pushing them further out once I reach them. But it’s about small, repeatable steps in the right direction that I can actually attain, and matching that with extreme focus. So, “the one big thing”: I kinda call it that.

John: Can you share an internet resource like Evernote with Fire Nation?

Jay: Yeah, it goes into my personal habits. So, it’s an app – free app, I believe, called SelfControl App, and it looks like a little spade with a skull on it.

John: I got it on my desktop right now.

Jay: Do you? Awesome. It’s so good, right? So, really quickly, for people who are unfamiliar with it: you basically have a blacklist of URLs. So, for me, it’s like ESPN, Facebook, Twitter, etc., and you put a timer over the top. And when you hit Start, you cannot access those URLs. So, it forces you to focus, and it also helps you see your bad behavior.

So, I’ll go to Twitter with SelfControl running in the background, and it’ll say it’s down, and my first thought isn’t, “Oh, right. I should get back to work.” It’s “Wait. Is Twitter down?” And I’ll go to Facebook, and ESPN, and then I’m like, “Oh, my god. I’m doing it again. I’m running through the same URLs. It’s not down. It’s me blocking it.” And so, now I’ve not only prevented myself from accessing that stuff, and getting lost in it, but I’m – I’m stepping outside of my day-to-day, and I’m actually able to see my behaviors, and – and change them. So, I love that app – SelfControl App.

John: Yeah. When you literally can’t get on those for the amount of time you do – like I just did a test one day for 15 minutes for Gmail, and then I was like, “Okay – I get it. It works. Now I can write an email…” and I’m like, “Oh, shoot. I literally can’t get on Gmail for the next 14 minutes now.” Like, restarting, nothing – nothing works.

Jay: It’s awesome. No, it’s awesome. And here’s the thing – JLD, you probably experience this too: you get lost in your work. And so, now you’re actually – the timer’s up, but you’re still going. You’re still not on the distraction.

John: Still going – the momentum. If you can just start. I love when Ernest Hemingway says he would always finish the day’s work prior with a half-finished sentence. When he just sits down, he just finishes the last sentence with the day before, which he knew how he was going to finish that, but that just got him going – because it’s all about momentum. If you could recommend just one book, Jay, what would it be and why?

Jay: This might be a little weird, but any collection at all of Calvin and Hobbes comics. So good, right? So, I think people today are all “go, go, go”, especially entrepreneurs. We love finding shortcuts, and hacks, and that’s kinda the culture, which has good and bad to it. But I think it’s important to ask and think about the big emotional questions, and really pause a moment to think. And I think you get better creatively, your subconscious helps you solve harder problems.

But these collections are exactly that pace. They have a surprising amount of depth. They kind of help you contemplate the bigger things out of a comic strip, and then on face value they’re just hilarious, awesome storytelling and – and copy, and – and drawing. So, I can’t recommend Calvin and Hobbes enough.

John: Jay, this is the last question, but it is a doozy. Imagine you woke up tomorrow morning in a brand new world, identical to Earth, but you knew no one. You still have all the experience and knowledge you currently have. Your food and shelter is taken care of, but all you have is this laptop, and $500.00. What would you do in the next seven days?

Jay: I literally can’t think of doing anything else but making Unthinkable. Hopefully, listeners see that, and hear that in my voice in the way I approach the show, and the community. But, I’d find the first handful of people that I knew, and I’d grab them, and I’d be like, “I’m making this thing! Come help me make it together.” And then, I’d maybe dole out some of the money to help support that, or the food that I have. I’d – I would go right back to trying to build a community around the same idea: what happens when you follow your creative intuition in business.

John: Jay, let’s end today on fire, brother, with a parting piece of guidance, the best way we can connect with you, and then we’ll say, “Bye-bye.”

Jay: The guidance is: you have to find joy in the process, not the results. And I think, by the way, that gets you better results. So, said another way, you gotta love the idea of building that body of work as your goal – not one hit piece, or project, or idea. So, if you make the process the point, I think not only do you find more meaning in your life but you also get end results. Make the process the point.

The best way to reach me: you can go to Unthinkable.fm. That’s the show homepage. It’s got all my social profile – URLs, as does SorryforMarketing.com. That’s more personal thoughts and snark. And I’m all over the place – Snapchat, etc. I do a lot of behind-the-scenes over on Snapchat. And I do have a gift for everybody listening. So, I mentioned that I’ve been looking at this Content IP idea, and taking months on end talking to people, tinkering on things, coming up with: how do you not only sustain a quality creative podcast, but grow it, and get actual resonance out of your audience, not just empty reach.

So, a lot of people listening, since it is a podcast, maybe you’ve thought of it someday. So, I wanna give away everything I’ve learned. I – I have documented my entire process for writing this very hard-to-create show that I have, and you can go to the URL – it’s – it’s a Bitly link. So, it’s Bit.ly/Firerundown, and again, this took literally months of my time with my team, getting feedback. Months of talking to other people.

So, hopefully it helps you shortcut that, and not copy me wholesale because then we’d have the exact same show. But – but borrow lots of it, and spend way less time preparing, and more time producing it, and getting results, and talking to customers. So, that URL, again, is Bit.ly/Firerundown.

John: Fire Nation, you’re the average of the five people you spend the most time with, and you’ve been hanging out with Jay A. and J.L.D. today, so keep up the heat, and head over to Eofire.com. Just type “Jay” (J-A-Y) in the search bar. His Shownotes page will pop up everything that we’ve been talking about today. These are the best Shownotes in the biz: timestamps, links galore. It’s there.

And, of course, head over to Unthinkable.fm. You wanna find out more about Jay’s show, and that great gift that he has for you will, of course, be in the Shownotes. But if you wanna go there directly, Bit.ly/Firerundown. Jay, thank you for sharing your journey with Fire Nation today. For that, we salute you, and we’ll catch you on the flip side.

Jay: My pleasure, guys. Thanks so much for listening.