Ep. 350: How to Thrive as a Creative Business Owner with Jay Clouse of Freelancing School

I'm so excited to introduce you to this week's guest on Pep Talks for Side Hustlers, Jay Clouse of Freelancing School!

After deciding to build his own way, Jay has taken what he knows about building products, companies, and product companies and applied it to creative businesses. Jay is the founder of Unreal Collective, a community of creators. Whether they are technology founders, freelancers, agency owners, or podcast creators, Unreal helps them determine critical next steps and achieve them.

Jay has worked with over 100 creatives and freelancers through Unreal. His clients have built launch sites for space flight, had multi-million dollar exits, six-figure crowdfunding campaigns, left their jobs to go full-time freelance, and bootstrapped technology companies!

Push play to listen to this week's episode, or read the full transcript below!

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Shannon Mattern: Welcome to episode 350 of Pep Talks for Side Hustlers. And I am so excited to introduce you to today's guest Jay Clouse. Jay helps creatives thrive as business owners and shows you how to become your own boss. He is the creator of Freelancing School, host of the Creative Elements Podcast, and author for LinkedIn Learning, teaching product management and freelancing. So Jay, thank you so much for being here. Can you share a little bit more with our listeners about how you got to where you're doing all these incredible things? Tell me your origin story.

Jay Clouse: Arguably too many things, right? It's great to be here. Shannon. Thanks for having me. I would say over the last decade I've really explored a bunch of different forms of entrepreneurship, which in and of itself is a small miracle because growing up, I didn't have any exposure to being an entrepreneur or starting businesses. Kind of found that route in college when startups were just very, very sexy. And I thought that is what I want to do. I want to be Mark Zuckerberg. I want to start something that's a billion dollars. It's gotta be technology. I'm going to do that. And so I helped co-found a company right out of college. It was a digital ticketing marketplace. We had some success, we went through an accelerator, we sold the company in 2015. Then I went and worked for a venture backed startup. And through those two experiences, I just realized the startup life is really intense and not necessarily the way that I want to be my own boss. I realized at that point that autonomy was really important to me. But the startup life is really intense and also fairly risky in the way that startup companies, you really have to commit like 10 years to doing this one idea and hope that it pays off really big or it pretty much goes to zero and you're starting all over again. And we weren't really talking at the time about the creator economy the way we do now. And that still was not yet in my purview. But then I started freelancing because I realized I want to be my own boss. And I think I could convince people to pay me to help them without being a full-time employee. I didn't even have the word freelancing in my vocabulary at the time either. So I started freelancing and that brought me into this world of the creator economy, started working with LinkedIn Learning on courses, realized I could produce my own courses. And all along the way just realizing the people I love working with, and I love serving, our other creative professionals who also have an itch to be their own boss, but they're not quite sure the way to do that. So that may be freelancing. It may be digital products. It may be something else. But that's kind of where I live now is helping people find that route and get up to speed, actually earning an income.

Shannon Mattern: I can so relate to that journey. I did not have any examples of entrepreneurs in my family. I didn't even have anybody in my family go to college before I went to college. So it was like the epitome of being successful was get good grades in high school, go to college, get a good job out of college and then work the most steady stable job that you could possibly work, making sure you have good benefits, 401k, so that hopefully someday you can maybe retire early, maybe in your like mid sixties. And then you get to like have the retirement lifestyle and travel and do all the things. And so for me, it was like, I craved autonomy too, you know? And it was 2015 when I discovered the Smart Passive Income podcast. And was like, wait, I could teach people? Because I did web design and marketing for my day job. I can teach people to do this and get paid by the companies? And so that's the path that I went down. I don't know about what your experience was, but everybody I knew thought I was crazy to walk away from the job that I was walking away from. So what was that experience like for you?

Jay Clouse: Well, in college, I didn't know what I wanted to do afterwards. I told you I helped start a company after I graduated, but at the time I thought, well, I want to go where the money is. I want to go into finance. Then I realized, gross. Finance is horrible. Then I thought, well, the money is also in either investment banking - but, again, finance, so I'm not going to go that route - or management consulting. And so I started interviewing with management consulting firms and I couldn't pass the math portions of the case interviews. And so I didn't get a job there. And I said, all right, screw it. Everyone's telling me that I should be doing this startup thing anyway, I'm just going to do it. So I didn't have like a traditional job experience because right out of college, I was doing the startup route. But after we sold that company and I took the job at the venture backed healthcare startup here in Columbus, I worked there for a year, realized I wasn't learning anything anymore. I was making really good money. But I remember calling my parents one day and just saying, Hey, I quit my job today and I probably will never have another job. And they're just like, what do you mean? What if you get a good opportunity? And I was like, nah. Not going to be for me. Little did I know a few years later, another one of my businesses would be purchased. And now I do have a job working with SPI and Pat, which is really, really fun. But yeah, people have definitely not understood what I was doing and looked down upon it at times. But then you come out the other side of it, where they start seeing you all over the place and they're like, why do I keep seeing your name places? Why do I see that you're doing this and that? This is crazy. How did you do this? How can I do this? It's like, well, you gotta be doing the things I was doing for four years that you're looking down on that wasn't paying me anything. And that's just kind of the story.

Shannon Mattern: So you said you're super passionate about helping other people who are just like you, want the autonomy, want to have a creative business, helping them make that happen. Tell me a little bit about how you work with people to do that.

Jay Clouse: Well, it began as a mastermind program, essentially, where I worked with a lot of creative professionals. A lot of them were early stage freelancers or kind of considering going out on their own. They might not have had the word freelance in their vocabulary. We would meet every week for an hour in a small group for three months. And I would help them go from A to B. On the backside of that we had a Slack community where I continued to help them and connect them with people and it was really rewarding. That business and that kind of format that I created was what was purchased by Smart Passive Income. Along the way, I started realizing that these people I was helping, especially in the freelance or creative services realm, they all had the same problems. And they were related to the business aspect of their business. They related to sales and marketing. And I was coming up with frameworks and systems that helped people, but repeating them a lot. I pitched the course first to LinkedIn Learning, about doing a freelancing course. And they said, this is great. Let's make it. We made it. I said, this is awesome. But I want to expand on this even further and go beyond some of the constraints that are put on you from that environment. LinkedIn just has a very specific way of doing courses. And I wanted to have longer videos. I wanted to do screen shares. I wanted to create my own resources and things. So I built Freelancing School as this platform to help people make a living freelancing. And instead of picking any one vertical, even myself, I flexed into a bunch of different types of freelance roles. I'm not gonna teach you how to be the best copywriter or the best designer or the best engineer, any of those things. But I can teach you how to build a business that actually gives you the freedom and flexibility that you want. I can teach you how to market yourself, and I can teach you how to sell more projects or earn more on your projects. And so that's predominantly what I do with Freelancing School now.

Shannon Mattern: So people bring the skill to you and then teach them how to turn that skill into a freelancing business.

Jay Clouse: Yeah. A lot of creative professionals, they know everything they need to do fantastic work. That's not the hard part. The hard part is you get into freelancing because you want to earn more and you want to have more time for whatever you want time for, a family, traveling, or even just like building digital products and things. But the tragedy is unless you really get good at being a business owner and know how to run operationally a business, you don't get rewarded with more money or more time. And a lot of freelancers find themselves working more than ever before and earning less. And that sucks. That's really, really bad. So I want to help curb that off. The math is pretty simple. If you can invest in a couple of courses that teach you how to earn more as a freelancer, that pays off very, very quickly, and I'm happy to do that. But again, like I said, it's, it's more about teaching you sales techniques, teaching you marketing techniques, teaching you the things that you need to do to run your business and have cash on hand, be able to pay your taxes. Things like that, that most of the people I worked with struggled with.

Shannon Mattern: Oh yeah. If we could have met back in 2014, when I first decided that I was going to quit this job, and my first idea was web design. Right? Because that's what I was doing before I heard of Smart Passive Income, and affiliate marketing and all of that. I was like, I'm just going to hang out my shingle as a freelance web designer because I have this skill. I literally had no idea how to price my services. No idea how to hold boundaries, no idea how to market myself beyond word of mouth, which led me to not the right kind of clients, you know, all of those things. And I didn't even know... this podcast is my public service a lot of times.... because I didn't even know there were resources out there that could help me with all of these things. So I learned the hard way. And it took me three years to build my business to the point where I was comfortable quitting my day job. And I could have done it in six months had I just had help.

Jay Clouse: Yup. Knowing how to structure things, knowing how to price yourself, knowing how to lead conversations and sell projects, and simple stuff like budgeting and taxes. Yes, you can probably figure some of it on your own through a couple of years, but those couple of years may be pretty painful and maybe so painful that it causes you to go back and get a job pretty soon after that. I mean my first year of freelancing, I didn't understand cashflow. I went broke. I didn't have money to pay taxes. I had to earn a ton of money, none of which I got to use because it all had to go towards taxes. And that's all avoidable stuff if you're aware of it and you go into this with eyes wide open. But we often find, or I often see, that creative people think that creativity and business are at odds with one another and they're almost actively resistant to embracing the business. But again, the tragedy is, if you don't do that, it's not going to reward you with the time and financial resources that you want to live the life that you want. So you kind of have to get over that and realize that business is not good or bad. It's the way you operate it and the way you embrace it and the value that you put onto it.

Shannon Mattern: I think that's so interesting that you bring up creative people think that business and creativity are at odds. And the way that I see this manifest itself with a lot of people in our community, and a lot of listeners to this podcast, is pricing, where they feel guilty about charging sustainably, and all of the thoughts and everything that come around pricing. What do you see with that in your community?

Jay Clouse: Pricing is definitely a big one. But even before pricing, it's being able to bring up the idea of selling anything. A lot of times people just have a lot of baggage with selling anything and saying this is what it costs, regardless of price. And I like to just try to give people the image of you're selling services, but you're still selling a solution or something that is tangible in a way. I went into Starbucks this morning. You look at their board. They say, here's what we have. Here's the price for it. No one is forcing you to buy anything. And usually you go up there and you pay the money, you leave and you're happy. Selling services is the same thing. You can approach it the same way. Here's what it costs. Here's what it is. You can have it or not. You're making an offer to these people. You're not twisting anybody's arm. You're not forcing them to do anything. But I think we're grown up in a way that we only recognize sales when it's done poorly. And so we start to put baggage onto the term 'selling' as a bad thing. But sales happens constantly. And when it's done well, it's invisible. And you can be that person doing sales well invisibly because people appreciate what you're bringing to the table. And they walk away happy that they invested in your services and in your help. It's a hard thing to get over. But it's really important.

Shannon Mattern: I love that you just said when it's done well, it's invisible. Because yes, I think that we all have had that experience where we're feeling like super pressured by someone in a sales experience. And I think you really put your finger on exactly what it was for me back in the day where I didn't want to make people feel the way I had felt before. And so I very much resisted selling. I knew I had to kind of tell them that I had something, but like in a very wishy washy, maybe if you might want to kind of way. But if you're doing it well, like you said, it's invisible. People are finding, not finding you. You're still going out there and finding people. But you're talking about things in a way that it's like, this is your choice. I'm here to give you all of the information that you need to make the best choice for you. And if it's me, awesome. And if it's not me, awesome. But I want you to feel confident either way.

Jay Clouse: We also have this problem of separating ourselves from our knowledge. So we think about a price and we think would I pay that? And our immediate answer is, of course I wouldn't pay that because I can do it for free. Of course you can do it for free, you're the one with the skill. But I can tell you sitting here now as a business owner that hires a lot of freelancers on a pretty regular basis now, a lot of the things I hire people to do for me, I could do, but it's more worth me spending money than the time to do it. Anybody that you're potentially going to work with, maybe they could spend the time to get the skill that you have, but time has a cost. And most people are happy to spend money right now, as opposed to the time to do it themselves or first, learn it so they can do it themselves. So you have to realize that. Like you're saying, you're making an offer. You're not forcing anybody to do anything. You're saying, here's everything you need to know. I'm going to make you comfortable that I understand your problem and that I feel confident I can deliver the solution. Here's the price. And I would love to work with you. There's this really great story that I like to tell of a director. I was listening to a podcast and this guy was an actor, but he had just taken on a director role. And he said the difference from being an actor to a director is when you do casting as a director, everyone who walks in that door, you're looking at and saying, I hope you are the person we're going to cast for this role. I hope you can solve our problem for us. And we don't have to do any more of these auditions. Meanwhile, the actors come in and they feel like they're under pressure. And they feel like the person on the other side of the table doesn't want them to win. But you have to realize everybody wants their problem solved. They want you to be the answer to their problem. They're rooting for you. So if you embrace that and make them feel comfortable that they're making a good choice, often they'll go with you because they just want the problem to go away and they're ready to stop price shopping, or looking around at options and move forward towards a solution.

Shannon Mattern: Yeah, and it's not like you went to their house and kidnapped them and brought them to your store and said, you must buy something. They found their way to your website or to your social media profile or to your podcasts or to your webinar, whatever method you're selling, they found their way there for a reason. And so it's your responsibility, I feel like, to share with them how you can help them solve their problem. And it's a win-win when it's a creative skill that you have that you love to do and it solves someone else's problem. We win at life when we get to make money doing that. So tell me some of your favorite transformation stories from some of the people that you've met along the way with Freelance School.

Jay Clouse: Oooh. I won't use any names because I didn't ask their permission, but one of the first clients that I had in the accelerator program or the mastermind program, if you wanna use that terminology, that I ran, they were a copywriter and they were working for a company full-time and just not earning much at all. And they decided 'I'm going to go out on my own'. And within a matter of months they had earned back their first year's salary. And year two we worked together again and they were doubling that salary. And now they're building digital products, they're running their own programs. And it's incredible to watch. And what they just needed was a little bit of a structure because they were already ambitious, they were already super talented. Maybe a little bit of confidence in some early clients. But they would come to the community and say, here's a question. We would be able to answer it, either I would, or someone else in the community. They would take that and run with it. Most people innately have what they need. When you surround them with the right information, resources, support, encouragement, they can really flourish. And some people need more encouragement and more resources than others. But that was really, really great to see. I've had a lot of students go through the Freelancing School courses, and there are a couple of resources in there that I think pay for the courses themselves. One of them being a proposal template that I've personally used. And people are like, wow, I just sold my biggest project ever using this proposal template. One being a CRM that I use to manage a bunch of different client projects and different stages of where the deal is. All of that. Every time someone goes through that and says, 'well, I just sold my biggest project ever'; 'I've earned more than ever before this year;. 'I just signed a new project in a matter of a couple of weeks; it's really rewarding in that way because I've been the person that got into freelancing to have more time and have more money, and then felt like I've neither of these things. So when you can give that back to people, it's really great.

Shannon Mattern: So I was literally just having another interview just before this one and we were talking about the same thing that, you know, I ended up in the early days recreating the same trapped feeling that I had at my corporate job, because I didn't know how to do things differently. And you mentioned that you went through, you know, I got into this for more time and money, and I found myself at a point where I didn't have either of those. What was the shift for you that you needed to make to break out of that to where you are now?

Jay Clouse: There were a few things. Part of it was pricing because I was underpricing myself and didn't understand the impact that had on my cashflow. Cashflow is a concept that I think people don't understand or think about enough, especially in a world where you're doing a lot of client work and you have different payment terms. So you may land a big contract, the big client. But if they only pay you on a net 90 basis, sometimes net 60, sometimes net 30, that means even though you signed that project, you're not going to see money for awhile. Especially if the net 90 happens after the project is completed. You could spend months after you've completed a project not having cash in hand. And when you're an independent freelancer, that's really important. That cash might be your rent. And so you start to understand the urgency behind 'I need to start a project now' because actually realizing the return on my effort might be months from now. And people will get themselves into a place where it's like, oh wow, I am going to run out of cash next month. And I don't have a project in the pipeline. What am I going to do? Because it takes sometimes a month after project ends to get that in pocket. So that was something that I had to learn. I had to learn how to manage my own money also because when you work at a company, they set aside money for taxes, they pay for health care. You have to learn how to enroll yourself in healthcare. You have to start bucketing your money for different types of expenses. I put a profit first system in place for my business last year. And it has been life-changing in terms of peace of mind and how I know how much I can spend on certain operational things. Things like freelancers that I hire now. I just hired a writer. And I had to look at my bank account and say, what can I budget for this writer? But it was easy because I have a dedicated checking account to operational expenses now. And I have a second account dedicated to taxes and I just don't touch it. Money comes into an income account. I put 30% of that aside in a tax account. I never touch it. Tax time comes, I have plenty to cover it. And then all that's leftover, I get a refund from myself at tax time. It's beautiful. And then I think the last thing that helped me kind of break out of that was I start thinking about my time differently and doing things like theming my days and time boxing. I realized that I didn't like to have client meetings on Mondays or Fridays. I'm in control of that, most of the time. I can make my client call days and meeting days in the middle of the week. I can keep Mondays and Fridays open for deep work days on client projects, or my own stuff. And it was really as simple as just making those days unavailable on my Calendly and using Calendly to book all of my goals, for the most part. So all of that really helped me get better control over my time and my money.

Shannon Mattern: I can resonate and relate to so much of that. I have a saying, Mondays and mornings are mine. So I do not schedule anything on Mondays. I don't schedule anything before noon. I try to keep Fridays free. Fridays are normally for masterminds or kind of professional, personal development stuff. And then you to hold those boundaries for yourself because no one else is going to hold those boundaries for you. You have to hold them for yourself. I love that you put 30% in your tax account. I also have a tax account and I do the profit first method as well. And it is, it's just like, oh, I get a bonus. I paid my taxes and here's bonus money that I've already set aside. And I also actually spent this weekend setting up You Need a Budget, YNAB, for my business because I, like you, have the operating account. And I have a spreadsheet. But I didn't have any projections out beyond just like, I keep track of what happened in the past, but I wasn't doing a whole lot of forecasting for the future. And I think that's where a lot of my anxiety would come in where I'd be like, well, I have this money, but I don't know if I can do that. And are we going to make as much money next month as I did this month. And I was just constantly obsessed, and check my Stripe account, my PayPal account, even though it always came in. I know I'm doing the work, but just having that one extra system where I'm projecting for all of these expenses forward, I can see, 'oh, we're fully funded for at least the next three months today, I guess I can stop worrying and just get to the business of doing the thing'. Right?

Jay Clouse: Totally. And that's something that takes a little bit of practice to do. You and I can preach about how you should be doing it. But until someone really puts a system in place and starts to work through it and experience it, experiencing it is just different than hearing it. And when you experience it, it starts to play out all these cascading effects, mainly on your peace of mind and how you make decisions that are just so incredibly uplifting and encouraging and empowering. So I totally understand what you're saying.

Shannon Mattern: So with the way you structure your week, what does a typical week look like for you in your business

Jay Clouse: It's a little bit different now because the client services arm of my business, which was kind of back-ended by a community, that's what was acquired by SPI. And so now I work part time for SPI and I not only have to manage my time for my personal business, but I have to manage my time for SPI. And that means that my client services part of my business is no more. Sometimes I'll do consulting, especially on community, but most of my income for the business now is digital products, podcast, sponsorship, affiliate revenue. And so that's changing my life in a different way too, because talk about projections. It's really hard to project how much money is going to come in in digital product sales this month. It's been fairly consistent, which blows my mind. Because I'm not doing anything consistently that would say this is why you sold as many dollars in digital products as month. So it's hard to trust projections and be like, am I really going to make that again next month? How could that be true? But it just keeps happening. Anyway, I have a similar rule now for mornings. Mornings are mine. Unfortunately, a lot of our team meetings are on Mondays. So my Mondays have been taken away from me. But mornings and Fridays, I still really, really try to keep to myself. And the reason that I block mornings, I wouldn't necessarily say I'm a morning person in that it's not easy for me to wake up in the morning all the time, but my best creative energy is definitely the morning. And it will be zapped and gone by mid-afternoon or by the time that I start doing calls. I just lose that. So I try to keep mornings open for work time, whether it's my own independent projects or whether it's the work I'm doing for SPI. And then the afternoons are typically group meetings. I lead the community team, so I have to be on top of that. But I also have a team of freelancers and assistants for my personal businesses that I have to be in support of. I do a lot of podcasts interviews for Creative Elements. Those are usually in the afternoons. So it's pretty busy. It's getting harder and harder to find some that deep work time. I find myself doing Saturday or Sunday morning podcast editing a lot these days, unfortunately. But trying to pull those boundaries back to the weekends and evenings, which means I usually have to wake up a little earlier.

Shannon Mattern: I literally just instituted a no weekend working policy, which has been very challenging for me for the same reasons that you described, because they're quiet. Nobody's scheduling meetings on weekends. Nobody wants any of your time on the weekends. And so it's the quiet time that I could really kind of get focused on deep project work. But then thinking about why I created this business in the first place for that autonomy and freedom and flexibility, and just, you know, time with friends and family. And then I found myself always saying 'oh, I can't this weekend. I have some work I want to get done'. And that type of thing. And three months ago, I started this business in 2014, so three months ago I just started not working weekends. And it was hard at first. It was a challenge.

Jay Clouse: Where did you find that you could carve back some of that time during the week

Shannon Mattern: Hiring freelancers.

Jay Clouse: It was hiring. It wasn't well, I really buckled down and made sure there's no waste of time during the day.

Shannon Mattern: No. I'm very efficient with my planning and I'm not a procrastinator or anything like that. I have very themed days. I can produce a lot of work and I do not need to be the one doing all of it. Like you mentioned earlier, because I'm a techie person. Right?. So that's kind of my Achilles heel. I can do it all and I want it done on this schedule. So I'm going to get it done on this schedule. Now I have to slow down, onboarding and getting these new people up to speed. I had to put the brakes on for a couple of months, which is uncomfortable for a driven entrepreneur to not be able to get this project done next week, because I could if I was going to do it myself, but to bring other people on to do that, now I have to be patient, slow down. So that's where my work is. I can definitely relate to that structure. But yeah, I literally had to just draw a line in the sand for myself and hire to make that happen.

Jay Clouse: I think I need to do the same, especially some of the mechanical or manual stuff on the podcasting side of my business. I could really use some support there, I think. But, you know, there's a whole other kind of accountability that comes when you are hiring and leading people that eats into that freedom if you let it, in a way too.

Shannon Mattern: Yep. Yes. That's my next level that I'm working on. I'm like, okay, now I'm shifting from solopreneur to CEO, and I resisted that level of responsibility for a long time. Because I don't want to be responsible for these people. That's not why I started this business. I want freedom. I want autonomy. And now I'm shifting to oh, if I can learn to be a certain way and learn to run this business a certain way and not model what I saw modeled to me when I was in corporate, I can have that freedom and have an awesome team too. But it's definitely a learning experience. I'm right in the thick of it. I don't even know all the answers. I'm right in the thick of it.

Jay Clouse: I find that the people that I hire, the more they're telling me they're going to cost, usually that's a pretty good indication that they're also going to need less oversight. And I'm finding that probably the best way for me to step in that role that you're saying is to hire somebody really good, even though it might be fairly costly, to be basically like a GM, like a general manager of the business so that the questions and the decisions mostly go to them from the team. And they only escalate the things that they really, really need to, to free me up. But that's a level of investment that hasn't really been practical for the past years of my life. It's probably getting there now, but then that's a new level of risk. And it's just a big investment to decide is this where I want to put a lot of the money that is coming into the business? Do I want to take down my owner's comp and put more of it into op ex. Am I willing to do that? I haven't made that call yet.

Shannon Mattern: Yeah. It's fascinating, these decisions. I always just thought I was going to be a solopreneur. I never thought I was going to get to the point where I'm making those decisions. And it's like having a level of trust, the risk, the money, like there's all kinds of stuff wrapped up in it. And yeah, it's been a really interesting journey to go through that process. But I wanted to ask you about your podcast. Because you mentioned that you have podcast sponsorships. Tell me about when you started the podcast, what it's about, kind of its trajectory and how it operates now?

Jay Clouse: Well, my first podcast I started in may of 2018 with a partner. His name is Eric. And it was a podcast focused on startup investing. So like super niche, super nerdy. Loved the medium. And we still do that show to this day in the business. That business is its own business. That's its own thing. We haven't even brought into this conversation. That takes time too. But I love the medium and I wanted to have a podcast that was more aligned with the core of my business related to freelancing and creativity. And so I started this show. It launched in March of 2020, like right at the beginning of the pandemic. And it was talking to high-profile creators, people like James Clear, Seth Godin, Vanessa van Edwards, Matt de Avella, about how they broke through with their art and creativity, because a lot of these people do a lot of interviews, but they talk about the core of their business. Like James will talk about habits. I want to talk to James about how did you make a as an author? That seems really hard. Tell me about that. And now that the creator economy is a little bit more in vogue, people are curious about that. And so I'm having a ton of fun on that show. And I really go all out from the production side of things. I put a lot of work into the production on it. My sister does custom illustrations of every guest for the show. It's super, super fun. So we're 59 episodes in as of this recording. The shows had 650,000 downloads in the last 14 months or so. And it's been a lot of fun. That's where I'm having a lot of my fun outside of the core of my business. It's just been great.

Shannon Mattern: So two questions for you that came up for me out of that. How do you get people like Seth Godin and James Clear to say yes to a new podcast?

Jay Clouse: Well, Seth and James were literally episodes one and two.

Shannon Mattern: Yeah. Well then there you go. How do you pitch someone and say, Hey, no one's ever listened to this podcast before. It's brand new. You guys are going to be the first. I mean, I'm sure that's probably not what you said. The question is for everybody. How do you pitch someone and get a yes?

Jay Clouse: Well first let me just say that I have a lot of success with cold emails. Access is easier than you think if you write a thoughtful, personable, direct, and short email. For those two examples specifically, Seth has a program called The Podcasting Fellowship and my first podcast was in the first cohort of that program. And we wanted to be a poster child for that program. And so we kept posting on our progress. We got some press for that show. I shared it with him. We had a preexisting email thread about that show that I responded to and said, I'm starting a new show. I think you'd be a great guest. Let me know if you'd be willing to record. We had to book it out like months in advance. But he was happy to do that, which was incredible. James also lived in Columbus. Apparently you and I both live in Columbus, small world here. And I had known him for a couple of years and we would get lunch or coffee a couple times a year. At least up until the book launch. And the book launch catapulted him in his life. And he's just been super, super busy. But again, I reached out to him and said I'm starting to show. Zero obligation whatsoever. Would love to catch up, would love to have you on it. And now that I have Seth and James and others, it's easier to cold email other people and say, here's the type of people that come on this show. And it perpetuates in that way.

Shannon Mattern: So cold emails that are thoughtful, and relationships.

Jay Clouse: Yep, Cold mails, relationships. And it could be direct. It could be fairly indirect. I never ask for direct introductions from my guests to somebody else because it's a little awkward. But I do tell them the type of person I'd like to talk to and say keep me in mind if it seems like a good fit for in your network. And that turns into some introductions, which is great. But yeah, in the beginning, if it's a favor, you kinda have to recognize that it's a favor. I couldn't have gone to Seth and said this is going to change your life and you're going to have so many more followers by going on my podcast. He knows, and it's worth acknowledging, I appreciate you doing this for me. This really isn't going to do much for you. And I always end my emails with zero pressure or expectation. Thank you for the consideration. A lot of times too, when people make cold asks, they just make the timeframe too small. You can write this beautiful email and someone's reading it like, yes, you know what? I will do this. And you end it with, do you have time in the next week or two to talk? It's like, no, I don't. I really, really don't. And now you made me feel like a jerk because I have to turn you down even though I didn't want to, because you want to talk to the next week or two? I am protecting any time in the next week or two with my life. I'm not adding more onto my calendar. So if you say, would you have time to talk in the next few months? Much easier ask. Of course, yes. Let's push it into October.

Shannon Mattern: I love that because I feel like sometimes people think who would talk to me? This is impossible. I'm new, I'm starting out. I have nothing to offer or just even pitching themselves. And you don't even realize, there are so many people out there who understand that. Like Seth Godin understands that you are a success story for him. So it makes sense for him to come and talk to you. And so just ask. Because you never know. And be thoughtful about it.

Jay Clouse: And some people will say no. And if I did a good job in the first email saying no pressure or expectation, and they say, no, sorry, not a fit, or I don't have time right now, I always respond and say zero worries. No problem. Would you mind if I follow up in six months to check in again? And they're usually like yeah, fine. And then six months from then, they're much more likely to say yes, because they've already told you no once. And they told you to follow up. So most no's are 'not right now' in my mind, if you approach it in a patient thoughtful way. And every 'not now' is just one step closer to a yes.

Shannon Mattern: Well, that's so good. So I have just a couple more questions for you before we wrap up. And this is how did you get to 650,000 downloads in that period of time?

Jay Clouse: Two things. Luck and being on a podcast network. The show has been on the Podglomerate network, it has been since launch. They were incredibly great to work with up through launch, getting a little bit of buzz and helping us have a successful launch. The show has been featured on Apple podcasts and Stitcher and Pocket Casts and Castbox, and a few others. So every time the show gets featured, we pick up some new listeners. And I've had people tell me that it's their favorite show to listen to. And I think that's the bar you have to have as a podcast host, or as a YouTube channel even, to be somebody's favorite, because that means that they're probably going to talk about you and that's where most of the growth in podcasting comes from.

Shannon Mattern: I couldn't agree more. You want to tell people about the best episode that you just listened to and you're sharing it and all the things. So the final question that I have for you is one that I ask everybody that comes on this show, and that is what belief about yourself did you have to change to get where you are today?

Jay Clouse: Oh, wow. This is like fundamentally important, because I had this story I told myself up until 2017 that I was not creative. And I had to get over that to allow myself to start writing and publishing, which led into the confidence to learn a new platform, like podcasting. I really believed that I was very operationally talented, but that I was not "creative" and I didn't have good ideas. And I had to unlearn that. And I had to work with a coach to help me identify it so I could unlearn it. And then under learning was basically an exercise in proving myself wrong. Like just creating things so I could see oh no, I can do this. And then it's a muscle, you know? So yeah, that was a life-changing realization, and then a resolution to change.

Shannon Mattern: 'I'm not creative' to this podcast, to having these incredible guests and all of these downloads and all this success. That's incredible. And I love that you said you didn't just magically switch this overnight. You put some intentional work into that too, to get help and get coaching and mentorship. Because I was a lone wolf for many, many years in my business and things didn't really start to shift until I not only got help in the business for business tasks, but for me to grow into that next version of me. So yeah.

Jay Clouse: Totally. Yep. It's worth investing in yourself and support. They're called blind spots for a reason. You can't see them, and if you can't see them, you can't change them. And so you need to surround yourself with people, at a minimum, that can help you. And sometimes it takes investing in a coach or a community or a mastermind or things like that.

Shannon Mattern: Well, I think that is the perfect place to wrap up this episode. Can you share with everybody where they can go to connect with you and just all of these incredible businesses that you're running and just learn more about you?

Jay Clouse: Yeah. For sure. Well you can listen to Creative Elements in this podcast player you're in right now. You can find me on Twitter or Instagram at Jay Clouse. Everything is linked from jayclouse.com. If you're a freelancer, you'll find your way to Freelancing School there. But I'm pretty easy to find if you just search for Jay Clouse in any platform you're on.

Shannon Mattern: Awesome. And you guys can go to shannonmattern.com/350. I'll link up everything that Jay and I talked about, especially his Creative Elements podcast. Definitely go check that out. Jay, thank you so much for being here, for spending this time with me.

Jay Clouse: Thank you for having me Shannon. It's great to talk about some of this stuff with somebody else who gets it and has been through it. You're pushing me to hire someone like a GM. So we'll have to do an update sometime and I'll let you know if that happens.

Shannon Mattern: Oh, absolutely. I would love to. I would love to. So thank you again. Really appreciate it.

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