Jay Clouse’s podcast launched with a big-name guest – Seth Godin – and has featured a stacked resume of guests ever since. 

But while the names are familiar, the stories you’ll hear on Creative Elements still feel new. That’s because Jay is taking a fresh approach and digging deeper into these creators’ stories, and not just their expertise. 

He’s made many small, thoughtful decisions along the way that all add up to an incredibly well-produced show with raving fans, and our episode of Wit & Wire is full of insightful advice around podcasting, freelancing, and building meaningful relationships.

In this episode, Jay shares…

  • How Jay started freelancing, and why it can be a challenge for new freelancers to get started
  • How Jay and his upside co-host Eric created a unique three-part format for their podcast
  • How having  a niche podcast has helped Jay find meaningful sponsorship partners
  • How Jay has managed to book big-name guests, like Seth Godin
  • What most new freelancers are doing wrong, and how a small shift can help you find your true value and land better, long-term clients
  • Why Jay started his second podcast (Creative Elements) and why he recommends focusing on quality right from the start
  • How community has played a role in his business, and how he creates a truly engaged community in Unreal Collective

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NOTE: This podcast was transcribed by a free AI tool called Otter.ai. Please forgive any typos or errors.

Melissa Guller 0:00
Welcome to Wit & Wire, the podcast that takes you behind-the-scenes to learn how to start and grow a successful podcast that makes an impact.

I’m your host, Melissa Guller, and in each episode, I invite fellow podcasters and industry experts to share their best strategies and advice for podcasters of all experience levels.

Melissa Guller 0:21
Today, I’m excited to be here with podcaster Jay Clouse.

Jay is the creator of Freelancing School, which provides the training and community to help people make a living freelancing. With three courses, coaching, and community support, Freelancing School has the tools to help creatives thrive as business owners. He is also the founder of Unreal Collective, a community for founders, freelancers, and creators.

Jay hosts two podcasts: Creative Elements, a podcast for creatives in the trenches of building their businesses, and Upside, a podcast about startup investing outside of Silicon Valley.

Before we meet Jay, let’s learn a bit more about his incredible offer for Wit & Wire listeners.

Melissa Guller 1:03
Freelancing is on the rise – more people are hiring freelancers than ever before, and there's a huge opportunity for you to be your own boss and make a living on your own terms.

It’s an incredible way to make a living if you're doing it well, but the “doing it well” isn’t so simple.

So many freelancers quickly find themselves in the same vicious cycle of going project to project. Meanwhile, successful freelancers are comfortable marketing themselves, selling projects, and running a business.

Freelancing School will help you succeed as a freelancer, and as a Wit & Wire listener, you can save 25% when you join today. Visit witandwire.com/freelancingschool to check it out, and if prompted, use the code WITANDWIRE at checkout.

Melissa Guller 1:47
So Jay, welcome to the podcast.

Jay Clouse 1:49
I am very excited to be here, Melissa, thank you for having me.

Melissa Guller 1:52
Yeah, same. And to start, I'd love to learn a little bit more about your own freelance story. So when you quit your job back into 2017 What was your initial thinking or your plan?

Jay Clouse 2:03
The thing is I didn't really have a plan. I would was just getting off working for a year at a startup company as a product manager. And before that, I had run a startup company myself. So, basically a year after having a job, I was in the space of, Okay, I started this job because I was burnout, doing my own thing. And now I find myself burned out having a job because this just isn't the life that I wanted. And because the organization was changing directions, I ended up putting in my two weeks notice about a month sooner than I thought I was going to. So I wasn't exactly done with the plan yet. But it just seemed like the right time for me and the organization to part ways. And so I spent the first couple of weeks really just trying to figure that out. I wasn't sure what I was going to do. It seems silly now because for the last Several years like, I've been very much on my own, but I, in my previous business, I had a partner. And so going out on my own for the first time with no partner or co founder or like software we're trying to build, it was pretty unknown territory. But at the end of the day, I just kind of had faith that I could figure it out. And a rough idea of what I wanted to do, I wanted to do in terms of my membership, community and accelerator. And it just took me a couple months to kind of put that together and see if it would work. But it was very much uncertain in terms of what I was going to do. But certain that I could figure it out.

Melissa Guller 3:39
I think a lot of maybe creators will relate to that story. Maybe there's an inkling of something that we feel would be enjoyable to do. But there's a lot of things that I think hold people back from pursuing those businesses or creative projects. So what do you think are some of those big reasons why people maybe don't take that leap into freelancing or their own businesses?

Jay Clouse 3:59
Well, unless you have exposure to it, it's hard to even understand what it looks like. Certainly entrepreneurship was not in my worldview growing up. And I didn't have entrepreneurs as role models. And so it's hard to even connect the dots from where you're sitting today to running your own business and feeling comfortable and confident in doing so. So I think a lot of times people just don't have an analogue or feeling of the path forward. You know, everyone kind of gets started and they think, Okay, the first thing I need to do is make a business plan. That's not something people really spend time on anymore.

Jay Clouse 4:39
But if you haven't been exposed to modern entrepreneurship, it's it's kind of what you think running a business looks like. And then you have some of the other more insidious things that never go away like imposter syndrome or insecure insecurity like it's it's scary and the path that Most of society teaches you is the path of go to college, get a degree, use that degree to get a job, work that job. And for me, my family and my worldview taught me that you work that job until you retire, which isn't really the way that our peers and our cohort approaches the job market anymore. We, we really kind of stay at a place for two to three years at a time. But growing up, I just thought that you pick a career path, you get a job in it, you work it for 30 years and you retire. And it's a real diversion, to think about starting your own thing from that path.

Melissa Guller 5:44
Mm hmm. I think a big part of maybe taking this unknown leap into your own business is like you said, if you haven't seen it before, and you don't know what it looks like. It can feel very risky. And unfortunately, I think a lot of people aren't exposed to people who are running their own businesses or are running a modern business the way that it can look in 2020? And so I think that holds a lot of people back if they've never seen it with their own eyes and maybe don't fully understand it.

Jay Clouse 6:11
And who do you ask about it? You know, you have this plan, you have this idea. What comes next? What do I need to do legally or not need to do legally, you know, how do I start selling this thing? How do I even get a space in a commercial building? If I want to have a restaurant or a small shop like those things just seem so inaccessible? If you haven't had direct exposure to it? You just don't even know where to ask. You might not even be aware that Chamber of Commerce's exist, you know?

Melissa Guller 6:42
Mm hmm. I think that's what a lot of my goal with this podcast and even my business was to with the same way you're describing online business. I think that's how a lot of people feel about podcasting. Like it's this mythical or maybe even very confusing, saved only for the very tech savvy. kind of world. And so I'm hopeful that throughout this whole episode, maybe we'll be able to show people a little bit more about what both freelancing and podcasting can be like. So maybe first let's focus on podcasting. you started your first podcast upside. Why, at that time, did you decide to launch a podcast?

Jay Clouse 7:20
So Eric and I are because my co host on the upside, we were talking in, gosh, November or December of 2017. And he was in the finance world. I had for several years been really rooted in the startup ecosystem and startup culture. And I live in Columbus, Ohio. So around that time, we were starting to see more activity of startup companies in the Midwest and in Columbus specifically, getting more national attention and funding. And having been in the Columbus startup ecosystem for about 10 years. There were coastal venture farm venture firms that were reaching out to To me to create introductions to the companies in Columbus that I thought were worth talking to as it relates to investment. And of course, I was happy to do that, because those people were my friends. But also I felt man, if I am providing this this service, this value to a venture firm, helping them find deals that are going to, you know, hopefully, ultimately be very valuable to them. It seems like there was some value I could capture there.

Jay Clouse 8:28
And so I talked to Eric about it. And I was starting to explore what would it look like to start a small fund so that I could co invest with some of these venture firms on the west coast, in the Midwest companies here in Columbus, Ohio. And so we talked about it for a little bit. We both realized that that was a huge undertaking for two millennials who didn't have any direct venture capital experience to try to raise a fund while we're also doing other full time things. So he said, How about instead of doing that, we just kind of mimic what would be like to be an investor by interviewing founders in the form of a podcast. And that was the beginning of upside was basically, we read Jason Calacanis, his book called Angel, which talks about how he does angel investing. And he lays out a three step framework, which is you do research on the company, you talk to the founder, and you write down notes about what you liked about that investment opportunity or didn't like, and then you can revisit that every 612 18 months and see, you know, how was your intuition on that? How is that company doing? And we just use that to create the format of our podcast upside.

Melissa Guller 9:36
I was wondering where your format came from, because you guys do have a really interesting format, where you do the same three parts in every episode, and maybe you can just talk a little bit more about that.

Jay Clouse 9:44
Yeah, it came right out of angel book. We spend the first five to 10 minutes, introducing the company. They used to be a longer segment where we did a lot of our own independent research on the company, but what we found was in the interview, that came out a lot. So we just started the interview. The End Throw a little bit to talk about where it's based. Any funding they've raised to date, anything notable that we saw in our research, but is about five to 10 minutes, then we'll interview the founder for 45 to 60 minutes, talking to them, almost as if we were angel investors. And all those founders are pre series A, so they have raised, you know, usually less than $5 million to date. And then the third segment is just Eric and I, again, talking about what we liked about that opportunity, what maybe scares us about the opportunity, what we would want to see from that company six to 18 months from now, to make us more confident in investing in it. But yeah, that was all straight out of Jason Calacanis. his advice for how to talk to founders and consider investment.

Melissa Guller 10:45
I love that approach. And I feel like maybe listeners today can think about if there are books or formats that they like that they are enjoying in some other format that could be turned into inspiration for a podcast, backbone because I think there's so much more with form Like, I love that you had this set creative format, because so many shows are just doing either them talking solo the full time or even an interview. And those can provide great value. But I think there's so much more room for creativity to explore.

Jay Clouse 11:13
Yeah, that was insight that I have to give Eric credit for his he listens to a ton of podcasts. And he had the insight that we should have something that is structurally unique, and also consistent that can be kind of a hallmark of our show. So that we weren't just another interview show talking to founders, we had something unique about it. And we didn't even think about the show in the beginning as here, meet some founders we thought of it as learn how to invest with us learn how to think like an investor with us.

Melissa Guller 11:44
And who did you find were the listeners for your podcast?

Jay Clouse 11:48
This was a little bit surprising. It ended up being basically three segments. And one of the largest segments is actually venture investors themselves. Usually lower than the partner level. Usually we have principals or analysts or associates at venture firms who are kind of trying to expand their own deal flow pipeline. Then we have startup founders, which is probably actually our smallest audience members. And then we have startup employees. And what's been really surprising upside, we specifically talk to companies that are not based in Silicon Valley, not because we're anti Silicon Valley, but because the aim of the show was to showcase that there are companies outside of the valley that have very good investment potential.

Jay Clouse 12:37
And we still find that maybe, you know, I haven't looked at this, the stats for a little bit, but 25 to even close to 50% of our listeners are actually in the valley, believe it or not. So there are people who are trying to look at the rest of the country and see what are these opportunities like either because they want to start to expand their own pipeline of potential investment or because they're in the valley and looking at man, I really want to move back to where it came from or somewhere else across the country where the quality of life is a little bit higher.

Melissa Guller 13:08
I think that's so interesting to hear. And I love to that you pointed out, it's not that you're opposed to Silicon Valley. But the fact that you did choose to focus on startups that were it sounds like in the Midwest, right? Not just Columbus, but anywhere outside of the kind of standard coastlines. Not only does that set you apart, but it also just gives you the opportunity to tell other stories that maybe don't have a platform elsewhere.

Jay Clouse 13:33
Totally. And that focus has been both a blessing and a curse, depending on what you know, our goals might be for the show, because it is very niche, and that limits our overall potential listenership. But it also gives us the opportunity to really target our direct sponsor outreach and create more impactful sponsorship packages to us and the sponsor that aren't just based in a pure CPM model, because our listeners are so targeted.

Melissa Guller 14:08
Are you comfortable telling us a little bit more about what that model is? And how sponsorship has played a partner show?

Jay Clouse 14:13
Yeah. You know, most most podcasts that have meaningful sponsorship, do it based on their overall download numbers. And that's top 1% of shows shows that are getting, you know, 50,000 downloads per episode. We were just never going to hit that number. So for us, we wanted to look at well what is valuable about our show and about our listener, we realize that we have a listener that is very targeted, you know, I mentioned that it's venture investors, it's startup founders, startup employees, these people are able to make buying decisions, and their relationships with certain partners can be really valuable.

Jay Clouse 14:53
So for us, our first sponsor was a law firm that mostly represents startup companies. And so not only could we advertise that law firm to our listeners. But all of our guests on the show, we would say to them, Hey, if you're looking for a law firm that works with startup companies, we have a partner that, you know, we've vetted, we feel strongly about, and we're happy to make an introduction. Our second sponsor very similarly was a talent recruitment agency. So we said to them, if you're, you know, about to raise your series A, which most of our founders were, think about talking with integrity, power search, our partner who helps you find really great talent here across the Midwest. And those were partnerships that we were able to structure by just reaching out directly to people within those firms and building a relationship and saying, This is what we know about our listener. This is why we think it's valuable to you. And it's easy to pay off a higher CPM, when your listener is very, very targeted.

Unknown Speaker 15:50
And not only is it going to the listener, but even the guests on our show, we were able to make some connections that way. I think that's so helpful to hear you talk about because I do think That there's maybe misconceptions in both directions as consumption. One is that the only way to earn money podcasting is to have a giant audience and to get sponsors to pay you based on Download numbers, and there are so many other ways that you can earn money as a podcaster. But on the other end, I love what you're sharing, which is that through building relationships and having such a targeted audience, it feels like it's a win win for everyone, because I'm sure that the partners that you did work with ended up sure like making sales, but your listeners probably really valued your curated recommendations because it was so applicable to what they were doing.

Jay Clouse 16:34
And we we went above and beyond and creating the ad creative for that show, specifically with the law firm, instead of just saying, hey, this episode is sponsored by Taft law. Here's, you know, 30 seconds of a blurb about Taft. What we did was we worked with their attorneys, and sourced specific legal questions from our audience and pose those questions to the attorney and recorded them live on air responding to those questions. And so not only were they showing that okay, TAF is the sponsor of this episode. Here's a little bit about them. But there's also showcasing that they know their stuff. It showcases their personality a little bit. And it was just a much more useful ad read than just a quick blurb about TAF. That is just basically you know, 60 seconds saying the TAF exists.

Melissa Guller 17:27
I think that's such a great idea much more engaging and personal to and then, like you said, it helps them feel like people instead of just you reading about yet another sponsor.

Jay Clouse 17:37
Totally. It prevents a little bit of just the tune out because there's some reward to listening. You're learning something.

Melissa Guller 17:45
Great point. So, upside is still active. Overall, what have been maybe some of the biggest benefits that have come to you from doing that podcast before we talk about your second podcast?

Jay Clouse 17:58
Yeah, upside has been active for more than two years, we just had our two year anniversary. We've published every single week since starting that show with the one exception of a couple weeks ago, while the country was really recognized reckoning with the Black Lives Matter movement, it just didn't seem like our place to take up space that week. But some of the biggest lessons that we've learned on that show or some of the biggest benefits, more than anything, it's been the network, the people that we've met, and had the opportunity to talk to who have introduced us to other people.

Jay Clouse 18:32
Eric, and I joke that usually the best part of the conversation is actually before or after the interview, usually after, because you have you know, 45 minutes of talking with somebody and building rapport and you're asking a lot of these questions. And if there is something that they feel compelled to share with you because they're starting to know you like you have a relationship with you. But they don't want to say it on air when you stop recording. Now all of that opens up and they and they tell you a little bit deeper of a story about some of these things that they're not really comfortable sharing publicly, but they think is useful context for you and what you're doing. That's been awesome. And most of our guests come from introductions from past guests, you know, we we are trying intentionally to talk to founders and certain underrepresented cities across the country. And so yesterday, we just talked with a venture investment, venture investor in Bozeman, Montana. And we said, Hey, we haven't talked to a single founder in Bozeman, but we think Bozeman is interesting. Can you introduce us to one of your portfolio companies that's pre series A, and that will almost certainly yield a founder in an interview that is pre series A in Bozeman, Montana.

Jay Clouse 19:43
Similarly, we've talked to people we've said we want to get into, oh, aging, who's an investor that researches or invests in aging startups. So I think, you know, that community that you build personally we've we've even sent a monthly email newsletter just to guests of the show that introduce other founders who've been on the show. So investors might be interested in introduction, we've introduced you know, the investors that we talked to the founders in our network might be introduced, interested in an introduction. It's really been all about the network. That's where the biggest value for us has been. And any piece of content that you create, you have no idea who that's going to reach. People get enamored with really big numbers, and these ideas like that. But even if you have a small audience, you never know that one of your 200 episodes might reach the co founder of this startup that you've admired for a really long time. We just released an episode with an employee at one of the largest private companies in the world, and the President of that company shared the episode. It's like, okay, our first billionaire has shared an episode of our show. And that's not stuff that we set out to do, but it's kind of a fun, natural Course events.

Melissa Guller 21:02
I love that you talked about the network and even just the value of getting to know people, because that's my personal favorite part about podcasting as well. And when people do focus on, you know, the downloads, the big numbers and all of those metrics, I mean, much as I'm a numbers girl, I think it's easy to overlook the power of just connecting with one guest as the host or your episode connecting even with just one listener, because there are a lot of one to one relationships that go on in podcasting that aren't talked about maybe as often.

Jay Clouse 21:33
Totally, any one relationship can very quickly and very drastically change your life. There was a large part of the the work that I do now is based in online courses. And that started because one person found one YouTube video that I put up just to host on my own website. She worked for LinkedIn learning, and she said, I think you should make online courses for us. I didn't expect that to happen. I couldn't have anticipated that and when you create content You put it out. That's the opportunity that you're opening yourself up to, you don't even know what you could see.

Melissa Guller 22:05
Wow. So I didn't know that part of your story. I know that you've got your online course. And I was gonna ask you about freelance school a little bit, but can you tell us how that YouTube video I guess then transformed into what is now Freelancing School?

Jay Clouse 22:17
Totally super bizarre story that again, you couldn't really reverse engineer and expect to work out but it's just a testament to the power of content. I was still working at the startup company, and I was a product manager. We had a local meetup that was looking for speakers, I volunteered, they said, Can we do it at your office and I made that possible by checking with my company. And we did that meet up in our sort of communal meeting space. The the natural benefit of that is we had a really nice camera that was set up to record all of our meetings that we could share with remote employees. And so I just recorded the talk. We had a motion graphics designer on staff Words and time and I said, Hey, can you take this video and overlay the slides on the drop down display that's in the back of the video to make it look really nice. And he did an amazing job. And I just thought, This is awesome. I'm going to put this on my website. And to put it on my website I had hosted somewhere, so I put it on YouTube.

Jay Clouse 23:19
I don't have many videos on YouTube, I actually have a lot of videos on YouTube, but they're all just for hosting. And I have no expectation of getting viewership from YouTube. But that video, which was called product management, one on one, I put it up in 2016 or something. It has, like 12,000 views or something now and at the time, it was in the top three results for the search phrase product management. And I guess at LinkedIn learning, they were looking to expand their product catalog in their courses. And the content manager was researching on YouTube for people to talk about product found me and thought that I could present well. And so she reached out to me on LinkedIn about applying to become a course instructor. And I went through those steps and got approved. And that was the beginning of making online courses, I created a few product courses for LinkedIn, which opened up the door to create some freelancing courses as my own career kind of moved from product to freelancing and small business. And yeah, I've been working with them for a few years now. And that led into creating my own independent courses and all of that. It's just because I put a video on YouTube, so that I could host it on my website.

Melissa Guller 24:28
I love hearing that because I think too often many of us I think even myself included a few years ago, it takes so much I think to put that first something out there, whether it's a first podcast episode, your first attempt at getting the client a YouTube video, but as happened to you, you never know what could come of just one video and maybe for some people, it's not the first one. Maybe it takes 20 videos 50 podcast episodes, but I think something that is, you know, the myth of the overnight success, it masks the fact that sometimes it really just does take one video or one piece of content to really elevate what you're doing into a whole new world.

Jay Clouse 25:05
Yeah, very, very low downside risk, very high upside potential, because people mostly just remember the stuff that was good. And usually they don't see most of the stuff that you put out. And that could be a bummer if you look at it that way. Or it can be really empowering to say, I'm just gonna keep putting stuff out that I believe in that I think is good. And the stuff that catches awesome, the stuff that doesn't, you know, sign around, that's fine.

Melissa Guller 25:27
Mm hmm. I forget which artist I like, maybe Austin Kleon talks about this, where what a lot of the greats have in common isn't necessarily that they were innately gifted, although maybe they were. But what they did was they just kept creating daily, they put out art, poetry, music, whatever it was, and then some of them turned into hits. But if they hadn't produced the vast quantity like the sheer volume of their work, then perhaps we wouldn't know them as household names.

Jay Clouse 25:54
Totally, totally everything is a lottery ticket. The 80/20 rule certainly applies. To content creation, and you see it on Twitter right now the people who have the fastest growing followings on Twitter and get the most airtime, they're, they're just tweeting like 10 to 20 times a day. They're putting out a ton of stuff. And some of it falls on deaf ears, but some of the catches and ultimately, if you pick up three followers or subscribers for every one that you lose, you're going to grow quickly.

Melissa Guller 26:24
Mm hmm. Well, I really want to talk more about Creative Elements, your other podcasts, but I believe Freelancing School did come first. So can you tell us more about the founding story of Freelancing School?

Jay Clouse 26:36
Yeah. So back to your original question of when I quit my job. The first thing that I thought I would do is facilitate mastermind groups basically bring together five small business owners and meet with them on a weekly basis, outline a path to success for where they are in their business. And then you know, ultimately help them get there on that path. That's what I thought I would be doing today. To make a living as an entrepreneur, and I'm still doing that to this day, I thought that I'd be working predominantly with startup founders. And it started that way, because I had an immediate network that were startup founders. But what quickly happened and has continued to be the trend for the last several years, is more and more freelancers, and client based businesses have come to me for that program. Because they are incredibly talented, they do awesome work when they find and work with clients, but they aren't as familiar with the actual ins and outs of running a business. And ultimately, if you're going to be freelancing, if you're gonna be running your own business, if you're gonna be self employed, you have to be confident and adept at running a business or you're gonna run out of money, you're gonna burn yourself out, you're not gonna have a good time.

Jay Clouse 27:48
And I loved that. I loved working with those people. And so naturally with LinkedIn learning, I kind of moved from product management into a really large freelancing course for them. That was the basis of me saying, Okay, well, I've already researched and created a ton of this content for LinkedIn. Most of my clients are client based businesses or freelancers. I'm going to productize more of what I know in the form of courses and I build off of that LinkedIn content, I really went deeper on it made it longer. And made more videos as part of the curriculum to put that under the brand of freelancing school to help anybody who is a current or aspiring freelancer, very quickly get up to speed and earn a very viable and comfortable living. Because when you get into freelancing, you do it because you want flexibility and control. You want a high quality of life where you decide how you spend your time, who you work with. And if you don't know how to run a business, you just don't find that reality. It's just a lot harder. You find yourself working more hours and you work before earning less. You don't have benefits because your healthcare isn't as good as it was at the company. And a lot of freelancers look at it and they say, What am I doing this isn't actually giving me a higher quality of life than I had at a job. And they go back. And that's a bummer to me. Because it doesn't have to be that way. freelancing can be an amazing way to realize that quality of life that you aspire to. You just have to be comfortable with your finances and marketing yourself, selling your services, positioning yourself. There's a lot of stuff that as an entrepreneur in the startup world, I just looked at as Okay, how do I create and position products that a lot of creative entrepreneurs lack, and I wanted to help them with?

Melissa Guller 29:39
Mm hmm. I love that. I think that it's maybe not intuitive that if you want to start your own business or be a freelancer, that you are actually opening a business, even if you don't maybe use that word at first like you are in the business of you. And there are so many skills. Unfortunately, they can be taught through great programs like yours, but it's probably not the very first thing that people think Have I have to imagine that they're asking questions like, how do I get clients? How do I earn money? And maybe what do you think are some of the skills for lack of a better word that are freelancing? Because I do think maybe there are misconceptions too, about what we're talking about where people are hearing consultant, writer designer, but I feel like I've heard you talk about much more than that as well.

Jay Clouse 30:23
Oh, my gosh, I mean, there are almost limitless skills that are freelancing. I mean, ultimately, what you need to be able to do is just showcase your skills as a solution. That's the thing. People buy solutions. They buy outcomes, they don't buy skills. And really the only solutions they're looking for are, I want more growth, whether that's in revenue, or profit or followers. They might be looking a little bit towards vanity, they might say I want to look more like my competitor. They might be trying to lower cost, but ultimately, if you can show how your skills map to a solution One that turns $1 from the business owner into $2 for them later, you know, that's a generalization. But if you can show that this pays itself off, you're not gonna have a hard time selling your work. But a lot of people go out and they say, I'm a copywriter who needs a copywriter. And that's not what you need to say you need to say, Okay, what is your business? You're an e commerce retailer. Okay? Would you like to have more customers? Would you like more customers renewing those things map to business outcomes that they care about, and maybe the solution that is better copy on their landing page or better copy in their transactional emails, but that's not what they want to buy. They want to buy the outcome. So you sell them on the outcome, and then you show them the path for getting there, and that uses your skills.

Jay Clouse 31:45
But outside of that, I mean, there's any number of skills that you can use, the way that I freelance now, it doesn't even really fall into the skills that you expect. Maybe some of my freelancing is copywriting, but it's also podcast strategy. It's community building. It's sales coaching, no, like, these aren't skills that you would go on Upwork and necessarily say, here's what I can do and just get products or projects that easily. It's it comes from me building relationships with people, understanding the problems they have in their business, and saying, I can solve that. And doing that. And usually that combines a number of skills. I actually think you are a more valuable Freelancer when you can sit at the intersection of multiple skills, and show that I am unique because not only am I great at copy, but I'm a good marketer too. And I understand how I can implement ConvertKit into your website, I can help you create these email funnels for your website. The more skills you combine into one person, the more likely it is that you can create a holistic solution, and that's what people want to buy.

Melissa Guller 32:51
And to be clear, though, when we talk about combining all these multiple skills, we aren't necessarily saying try to be the everything for everyone, right?

Jay Clouse 32:58
No, certainly not. I think It's it's best to start where you feel most comfortable and kind of branch out from there. And to me, it's more valuable to have strong, long term relationships with clients than just try to crank through a ton of clients who want a little bit of help on this thing. Because, you know, if you are a copywriter, and you do a project with a client who started with just wanting to rewrite their about page, you can then show them, okay, this is the result that you saw. And I think we have opportunity to do X, Y, and Z. And sometimes in improving those other or doing those other projects, you will learn new skills. And then you can take that next client and say, Okay, I'm gonna do this for you. But I also noticed that you have the opportunity to improve this area of your website or this area of your business. And I've experienced doing that. We just have to do X, Y, and Z. You will learn things in the course of action when you're really trying to just solve for problems and create actual business value for whoever your client is. And that makes you more valuable over time. But the the problem or the the danger that I see for a lot of people who don't want to, or are afraid to or uncomfortable with building the relationships with clients, they'll go to a marketplace like Upwork. And if if you have jobs coming to you on Upwork, that's great. If you don't, it's kind of a race to the bottom on pricing, and you're not building a ton of equity in yourself as the freelancer, and that will burn you out pretty quickly.

Melissa Guller 34:33
This has all been really helpful. I know I'm personally taking a lot of notes, even just about, you know, building the relationship starting with something and then kind of developing. Those are things that can apply, obviously, to freelancing, but now, I'm curious to hear how you think this could apply to podcasting. Like when you talked about, you know, showcasing your skills as a solution or yourself as something or someone who could solve problems. Do you think that there's an application there for a podcaster as well?

Jay Clouse 35:00
Yeah, I think so I think it mostly ties to, who is the audience that you're creating this for? And why do they need what you're making? And why is it different than the solutions they already have out there? So for your show here, Wit & Wire, you're helping people really learn some of the nuts and bolts about podcast strategy, which you don't hear a lot of shows a lot of shows. It's kind of like a, I'm talking this successful podcast, and we're kind of going off the cuff. But the more tactical you get, that's attracting a listener that says, I'm actually trying to learn the craft of this, and less just hear from new interesting people. Anything that you're creating, you should get crystal crystal clear on who is this for? Why do they need it? Why is it better than their alternatives, where you're gonna have a hard time carving out a dedicated listener base? Mm hmm.

Melissa Guller 35:52
I love the question too. Like why is better than the alternatives because it doesn't have to compete based on quality maybe in the way people are thinking it's not that you have to have the bigger guest or the better microphone or any of those things. But if you're talking to different stories, even though I was upside, you were choosing to spotlight companies that weren't in the standard regions. Or maybe you have a different perspective, because you're a woman or you're a minority, and there aren't a lot of people talking about your topic in your space. I think there's so much opportunity for people to stand up and speak about something and really stand out.

Jay Clouse 36:24
Yeah, I mean, it's, it's, it's about what is the unique value that you're bringing to this, that they're not getting from the other competitors. And you're right, it doesn't have to be a big name. But if you're trying to compete by just having big names. Now when you have Ryan Holiday on your podcast, your podcast interview with Ryan Holiday is just going to be compared with the other podcast interviews with Ryan Holiday unless you focus that differently in some way.

Melissa Guller 36:48
I do. Also, of course, now want to talk about your second podcast. So you have now a show called Creative Elements. Can you talk about why you decided to start that podcast

Jay Clouse 37:00
Yeah, and I'm really excited about creative elements. It's gotten the best feedback of anything I've ever made, which is not a low bar. But I thought I started thinking about creative elements, probably middle of 2019, which was basically me saying to myself in the beginning, I love podcasting. And I want a show that has broader appeal. And I want to show that's more aligned with the majority of what I'm trying to do. As a business owner myself, I'm trying to help more creatives Be confident business owners, building a life that, you know, enables the lifestyle that they want. upside is interesting. And it's in the the startup adventure realm, which just isn't really aligned with that.

Jay Clouse 37:43
So I started thinking about what would a new podcast look like? And I bring up the fact that it was middle of last year because I probably was in the concept stage and development stage of this for nine months pretty actively before I actually published it. And I started looking at my strengths and I tried it started looking What I could do differently that I wasn't seeing a lot out there already. And I also thought structurally what would be different and unique. And all those kind of coalesced into this idea of creative elements were at the core, I wanted to talk with some bigger names, but people who have made a successful independent living as creators, and not talk so much about their craft, because a lot of these people do a lot of interviews. And usually it's talking about their creative process or how they think about, you know, their work. And to me, I wanted to dig deeper into how did you actually build a business out of this? Because there are so many creators who follow these people. Episode One was Seth Godin, for example, so many people follow Seth Godin and lovely posts out there, but like, how did Seth get the opportunity just to write everyday for a living, you know, how did he build his email list? How do these people build YouTube channels, if I'm an aspiring creator, and I'm looking at these, these idols of mine who have huge numbers of subscribers and clients and customers on these platforms, I wanted to help create more of a roadmap for what did they do to actually build that business. And I was confident that I had some existing relationships with big names that could lead to other introductions of these people, people who were typically difficult to access. And I wanted to make the show unique in that. I'm asking very different questions of these people. And I want to make the roadmap more clear for their followers for how to get to the life that they have, if that's what they want.

Melissa Guller 39:31
What are some of those questions that you're asking? I'm sure they're slightly different for each guest, but maybe to give us an example.

Jay Clouse 39:37
It's pretty different for the guests because I'm trying to look at any platform that you can create on top of I want to talk to course instructors, I want to talk to podcasters. I want to talk to people who are doing paid email lists, YouTubers, people who have giant Instagram accounts, like I'm trying to understand how they built on whatever platform that is, but I'll ask them how this got started. What was the turning point? And what are the small number of tasks that you really invest most of your attention into, to drive the value in either growth of subscribers or in customers, you know?

Jay Clouse 40:15
And a lot of those questions kind of emerge out of the conversation, because I'll talk to Vanessa van Edwards, for example. She has 460,000 YouTube subscribers or something and millions of readers on our blog. And we spent the majority of our conversation talking about a business that I didn't even know existed. It was six years of her doing an education business for parents of teens, helping them connect to their teens in a digital world. I didn't know she did that. And that was the first six years of her business that gave her the foundation to build science of people, which is now this huge, huge creative Empire. It's awesome. And you don't hear that story when you see Vanessa and if you just start following her work and you say I want to do stuff like she does. You forget that, okay, well, she's spent six years of her life doing a different business that taught her how to. Okay, right for SEO, all these people talk about the foundation of my business is really understanding SEO and what people are searching for in my niche, having a client avatar, and writing specific articles for these people to bring them in. Like we get into how they structure their opt ins, all of that. And most these people, you know, they're focusing on, on most shows, talking about the core of their content itself. Vanessa helps people relate to other people. That's what she talks about on most shows. And yeah, we talked about that a little bit on Creative elements. But again, I really want to talk about, but how did that business get started? How does that actually work?

Melissa Guller 41:47
I definitely see how this ties into freelancing school because it seems, although a lot of us have really great skills, maybe it's the marketable thing. It's what Vanessa is known for. It's what you want to sell to your clients. The framework that holds that skill together and helps you actually build the business isn't talked about as much. And certainly, I enjoy learning about it. And I'm excited to keep tuning into more of your episodes myself, because I think taking people behind the scenes, showing them what's possible, helping them understand how the whole business came together is not something a lot of us are talking about. So I'm so excited to hear that you're continuing to find great guests to talk about how they did it.

Jay Clouse 42:26
Yeah, thank you in it's a little bit of a Trojan horse, because most of the clients that I work with are most of the creatives that I know. They look at these people's lives and they aspire to it. They're like, I want to make a living with my work online too. And these people don't talk enough about, hey, yeah, I'm a creative and I associate myself with a creative, but I'm also an entrepreneur. A lot of creatives are very resistant to being business owners, and that is exactly what holds them back. If you don't embrace that and you don't learn what that means and how to do that. You're not going to give yourself Enough time and focus to actually build that reality that you want. So instead of me just some guy beating the drum over here saying, hey, creative, you need to embrace being a business owner so that you can actually have this life. I said, I'm going to hear from the people they idolize and really admire, and let them tell that story. So that maybe that wakes them up.

Melissa Guller 43:20
And I do also, of course, have to ask a little bit more about maybe with podcasting and freelancers, who do you think is the right kind of person to start a podcast now that you've obviously had a couple of your own?

Jay Clouse 43:34
Boy, starting a podcast and starting a business I think of differently. So if we're focusing on who's the right person to start a podcast, I would say really just about everybody, it depends on what your goals are. If your goal is to have a top 1% show that has mega downloads, and that's how you're making your money, then you need to think more about being a business owner and what it means to be a business owner. But if you just want to meet people Get in the habit of habit of publishing. Create some lottery tickets for yourself. I think podcasting is incredible medium. I think it's a great way to learn how to speak and how to ask good questions. And to me, you know, Toastmasters is this massively popular public speaking training program. podcasting is so much more valuable than Toastmasters. Because you can get way more reps. You can hear your recordings, you can talk to anyone on the planet, potentially, you know, Seth Godin is not going to walk into my Toastmasters chapter. And you can edit the whole thing before you publish it. So to me, it's a really great way to learn how to speak, learn how to ask questions, build really incredible relationships where you're getting off on the foot of providing value to that person, you know, yeah, you're getting 30 to 60 minutes of their time, but you're also providing them then with an asset and hopefully some, some new subscribers, followers, potential clients. So you're Starting with the standpoint of flattery and providing value, which is a great way to start some relationships.

Melissa Guller 45:06
And I love that relationships has been a theme throughout this whole episode. And I guess I'd also love to ask one more question about the interviewing, which is, how do you prepare for those interviews, especially with such big names, who people do know a lot about, like you said, but you have the goal of maybe touching on something a little bit different?

Jay Clouse 45:24
Well, the most important preparation was probably the two years I spent doing upside, getting comfortable interviewing in general. But now, I think the two most important activities that I do are one research, do my homework. You've obviously done a ton of research for this interview, which I'm super grateful for. So look at you know what they're doing. But the best research research that I find is actually listening to other podcast episodes with them, especially recently, because that will show you some of the stories that you want to pull out in your show also, but will also give you some of the questions that everyone's asking that you Don't need to ask again. Because you want your show to be unique and not just unique for the listener for somebody that might binge listen to interviews with Bo Burnham like I do.

Jay Clouse 46:08
But for somebody who you want to be a memorable interviewer to the guests, because if they're already doing a lot of shows, they're probably not going to share your episode. Unless there's a reward for doing so. And for a lot of them, they're not going to share the same 45 minutes of them telling their story or saying sharing the same tips that they've done in the past. They want to share a unique and new story. They're gonna say, Wow, that was different. That was a different interview. We talked about different stories. This like, reignited my interest in being interviewed, you know, that's the impression you want to make on these people. So do your homework, listen to other podcasts episodes. And then the last thing I'll say is, I actually think about what I want the takeaway for the listener to be before I start the interview, which sounds maybe a little bit backwards, but in the process of booking guests, you're already booking them for some reason. So make sure explicit. You know, let me give you an example. I recently interviewed Myles beckler. And he is like the go to guy that I get pointed to constantly for affiliate marketing. So if I'm if I'm going to talk to miles beckler, the theme of that episode is going to be affiliate marketing. And could he talk about freelancing? Could he talk about all kinds of things? Yes, but I'm focusing that conversation on affiliate marketing, because he is the guy for that. And that's going to help me craft the questions that I want to ask and really focus that episode so that it makes it more likely to be shared to people who care about that topic.

Melissa Guller 47:31
Mm hmm. I think that's such great advice. Because ultimately, we're thinking about the listener. In the end, we want the listener to have a great experience. I think a lot of my listeners might be surprised to hear that I often spend more time researching than I do in the interview itself, because I want to make sure that I'm asking questions that are going to be insightful that are going to be unique, like you said, that aren't just like every single article that I definitely talked about you in advance of this call. But you also want there be some kind of narrative. And so I always kind of imagine like, what do I want to title this episode? In the end? Because I think that helps me give clarity on some of the questions that I asked or some of the questions that I don't ask.

Jay Clouse 48:10
Totally. And if you don't have that, as a listener, even if you don't realize it, you feel it. You feel like what are we talking about here? How do we get here? Why are we talking about this? When you build more of a narrative arc like you're talking about? It makes the whole listening experience more natural, and you're more likely to keep people engaged and listening through the entire episode?

Melissa Guller 48:29
Mm hmm. Well, I do have one more question. I know, I definitely wanted to hit on because we haven't even talked about your community yet. And I'd love to hear a little bit more, especially because I think a lot of podcasters are thinking about, should I have a community that goes along with my podcast? So can you tell us a little bit more about unreal collective?

Jay Clouse 48:48
Yeah. Unreal collective is really the core of my business. It's that 12 week accelerator program where I put groups together of five entrepreneurs plus me and we meet every week for an hour. On the backside of that we have a private community that historically has been in slack is in slack right now, we'll be moving to a different platform soon. But that's where I spend most of my time online. It's awesome. It's, it's where I have a very curated group of people who have similar interests, similar values, and they're, you know, going after the same goals. Community is one of the most important and impactful forces in my life and the life of a lot of people that I know. If you have a place where you feel safe, and where you feel like you can get answers to questions that you have, you don't feel scared about asking them in front of these people. It can really, really accelerate what you're able to do as a creator or as a business owner. so unreal collective is where I've been doing that and just about everyone in that community has been through the accelerator program at some point. Some people do opt in just as community members and I think more people do In the future, but it's important if you're going to have a community to think about, just like podcasting. Why does this need to exist? Who does it exist for? Why is it different than what they can get elsewhere? And the value of most communities is actually in curation. You know, I've intentionally kept that unreal community small, because I just don't think more than 100 150 people in a slack group can actually feel connectivity between each other. Because the platform is not built for that. And so it's important to think about the platform you're on who that community is for how to make it feel inclusive, yet sort of exclusive in terms of being curated because people value you know, where they can feel safe and seen and understood. And as the champion of that community, you need to create and hold that space, which is a lot more difficult than I think people realize.

Melissa Guller 50:57
I wanted to ask about community because I know you'd made some So many intentional decisions that I don't see, in a lot of other communities. I think we hear the word community and sadly now we just hear, oh, Facebook group. But what you're doing where you have not just limited the size of the group, but who can join and their overall experience and what's talked about and I know you have smaller groups, even right within the group of people who can engage in it, five to seven are much smaller goods, five plus me, so six total, but really five. I think that kind of really intentional curation of every part of the experience is not something talked about very often, but I have to imagine, it makes a big difference. So maybe just some Brief Advice. If a podcaster is considering having a community, what are some things that they should definitely consider doing or not doing in order to maybe hold space?

Jay Clouse 51:50
Well, first, I would think about timing because it's difficult to start a community and get it going. Because in the beginning, if If I invite everyone in at the same time, you have a bunch of people joining a party that doesn't really feel like it's in progress. And people want to join a party in progress. They don't want to join a sinking ship. So it needs to feel like they are getting a unique opportunity. And they're joining something that's already exciting. And that's hard to manufacture in the beginning when it's literally an empty room. So start with some people that you think will be really strong pillar members who are invested in having that community be successful also. So they can start to create conversation and create engagement before you drop in a bunch of new people. Because you just don't want to have that empty room effect where people back off and never come back. To make it feel safe.

Jay Clouse 52:48
Some people call this like the heads on sticks approach, which is basically you lay out the rules as the community moderator and your expectations and the values that you have for the community. And you say I trust Due to apologies, but if you don't, we're going to enforce them. And if somebody doesn't, you need to enforce them, you need to make an example of that behavior and make it a negative example. And if you have to weed people out, you weed people out. Mm hmm. And the tricky balance here is finding a way to be fairly objective in who you allow in so that it's not some sort of subjective, exclusionary, not based on anything measurable type group, like you need to be able to tell people why you would not be brought in. It needs to be fair, and it needs to be explicit. But ultimately, the value comes in curation, you need to make it a place where people feel like okay, this is for me. And that's rooted in understanding who that person is and what they need.

Melissa Guller 53:54
To me, a big takeaway I've had throughout this whole episode is just really knowing who you're for And whether it's the podcast listener, your client, the members of your community, just being really intentional about who that is and why you want to be around those types of people is something that I know. I'm going to take away. And as we do kind of start to wrap up, maybe do you have any final advice or words of wisdom for new or early stage podcasters about their shows?

Jay Clouse 54:22
Yeah, I think podcasting has such a low barrier to entry, which is exciting. You could start a podcast tomorrow. And it's still early days. But I think it's a good idea to be really thoughtful about the long term goals and trajectory of the show. I did, probably more than a dozen interviews before I published the first one. And that was because your guest list is largely determined on your existing guest list. And your guests really dictates the quality of your show if you think about it. Most of This interview has been me talking because that's the way interviews work. So if I'm a bad guest, this is going to be a bad episode. So you need to have good guests in good guests are going to look at your existing guest list and say, is this something that people like me Go on.

Jay Clouse 55:16
And so you want to start with really high quality, high quality production, high quality guests, you may have to pull some strings in the beginning and get people to bet on you, as a person like Seth and I recorded before the show existed. And I pulled that off because I had bought just about every product ever done. When I asked to be on the show, I asked him an email thread that we had already exchanged in the past about the podcasting fellowship, which is his program around podcasting. And once I had Seth on the show, it was easier for me to reach out to people like Vanessa and say, Hey, I'm starting a new show. And I've interviewed Seth, Seth Godin, and James clear, that's just a signal to her that Oh, those people are probably done their diligence. This is probably a good use of my time. And that only compounds over time. But once you start publishing, they're going to listen to those episodes are going to see what is the production quality, like, how did this interview go? Did it seem comfortable? And so I think from the beginning, being intentional about your art, your structure, who it's for why they need it, who you have on the show, starting with high quality is going to serve you if you want to take this seriously in the long term. Mm hmm.

Melissa Guller 56:24
That's great advice. Well, thank you so much for joining, where can listeners learn more about you?

Jay Clouse 56:31
If you're listening to this and this jived with you. You can find me at jayclouse.com or on any social media @jayclouse.

Melissa Guller 56:40
Awesome. Well, Jay, thank you again. It's been such a pleasure getting to learn more about you, your business, your multiple podcasts, and I hope that listeners really enjoyed this as much as I did.

Jay Clouse 56:48
Thanks, Melissa. This has been fun.

Melissa Guller 56:51
Thank you so much for joining us this week. To learn more about Jay and to see the key takeaways and references from today's episode, visit the show notes at witandwire.com/16.

If you enjoyed this episode, I’d love to hear your main takeaways. Share a screenshot or a photo of you listening to Wit & Wire on Instagram and make sure to tag me in your story @witandwire.

Lastly, remember that as a Wit & Wire listener, you can save 25% when you join Freelancing School by visiting witandwire.com/freelancingschool. If prompted, use the code WITANDWIRE to start saving and freelancing today.

Thank you again for joining me, Melissa Guller, in this episode of Wit & Wire. I’ll see you next time, podcasters.

Today’s guest: Jay Clouse

Jay Clouse is the creator of Freelancing School, which provides the training and community to help people make a living freelancing. With three courses, coaching, and community support, Freelancing School has the tools to help creatives thrive as business owners. He is also the founder of Unreal Collective, a community for founders, freelancers, and creators. 

Jay hosts Creative Elements, a podcast for creatives in the trenches of building their businesses, and upside, a podcast about startup investing outside of Silicon Valley. You can connect with Jay on Twitter @jayclouse or sign up for his weekly newsletter for creatives at jayclouse.com.

Connect with Jay

Podcast spotlight: Creative Elements

“It’s never been a better time to earn a living with the things that you make. Creative Elements bridges the gap between art and business by talking to high-profile creators about the nitty gritty of building their creative career.

We discuss the specific elements of their personality, style, or approach that have helped them thrive: elements like focus, vulnerability, revision, and constraints.

By learning how these creators made a living with their art, you’ll feel more confident earning a living on your own terms too.”

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Hey! I'm Melissa, the founder of Wit & Wire. My podcasts have reached thousands of listeners and hit six-figure downloads, and I also hit the charts as the #2 Career Podcast in America for Everything is Teachable.

It’s my passion for teaching that brought me to start a podcast in the first place, and I founded Wit & Wire to help more passionate, diverse creators like you expand their impact and income through podcasting.