The first social media influencer, crashes & rises

Over 10 years ago, I interviewed Jason Zook about how brands paid him to wear their shirts on social media.

Every day of the week, without a break, he’d broadcast himself live, post YouTube videos, take photos, Tweet, etc. He showed followers his life, and promoted brands the paid him.

How much money did he make? What happened when he crashed? How did he rediscover himself? Listen. It’s worth it.

Jason Zook

Jason Zook

Wandering Aimfully

Jason Zook is the founder of Wandering Aimfully which is a membership community for client-based business owners who want to transition into selling digital products.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of Mixergy, where I interview entrepreneurs about how they built their businesses. And 10 years ago, I interviewed today’s guest for the first time and get his model back then. He had a company called, IWearYourShirt. And he would get paid by companies to wear their shirts on social media. He would do it on sites that are dead like Ustream, on sites that are very much alive like Twitter. He would every day, it felt like all day, be visible promoting the t-shirt, doing live Ustreams where people could talk to him and hang out with him. Creating videos, I think it was for YouTube. I’m I right Jason?

Jason: Yeah.

Andrew: Where you would create videos for each sponsor. And these people, I think the model was on January 1st, you would pay him $1 to wear your shirt, for him to wear your shirt. January 2nd was $2 and would just keep building up as the year went on. He’s nodding, so I’ve got it. I thought the idea was fantastic. I thought the business behind it was fantastic. It turns out it wasn’t as fantastic. I thought it was incredibly grueling. We’ll find out how grueling it was. But the interesting thing was, that it was just a lot of attention around it. And he was really good at using social media at a time when most people didn’t get it, didn’t get the power of it.

And as a result of that interview and his success, I’d suddenly started getting a flood of people who are basically copying him saying, “Our whole family’s wearing t-shirts. We want to do the family t-shirt. Can we be on Mixergy?” I think, “Well, maybe once you get some traction, I guess.” Someone would come in and say, “I wear hats. I wear people’s baseball.” I guess, but not yet.

So the thing took off. I wondered what happened. He then did a bunch of other things, which we’ll find out about. And where he ended up is today, he’s running a company called Wandering Aimfully. It’s a membership community for client-based business owners. In addition, he’s got a new book that’s coming out by the time this interview is up, it should be out. It’s called “Own Your Weird: An Oddly Effective Way of Finding Happiness in Work, Life, and Love.”

And by the way, we say own your weird, I didn’t totally get into his weird stuff. He changed his name. He had somebody pay him, actually three different companies, he auctioned off his last name. They paid him to change his last name at three different times. He had this thing where he was selling his future. He said, “Look, I’m a creative person. I’m about to sell stuff. I don’t know what. Buy my whole future.” And then people started buying that and talking about that. So he’s really good at creating creative stuff that gets buzz online, and I want to find out about the business behind it.

We can do all that with Jason Zook. He is the creative we’re going to be talking to. We can do all that thanks to two phenomenal sponsors. The first will host your website right and whatever weird idea you have. They will host it. Bring it to HostGator, really. And the second if you need a developer to take your idea to the next level, to take your business, to take your team to the next level, you got to level up by going to Toptal. I’ll talk about those later. First. Jason, good to have you here.

Jason: Good to be back. Ten years ago. What?

Andrew: Yeah, man. Yeah. I’ve been doing this for a long time. I’m only into things that are long-term. I’m like a long, stick with it type of person. I see people that’ll start doing podcast, after the fifth one, it gets a little tiring, they give up. No, not me. I’m a marathoner. All right, let’s talk about this. At your height, how much were you making with the t-shirt business?

Jason: So in total, it made over 1.2 million in revenue over the five years. The first year, when it was just me, as you talked about with the, what I call now bump sale pricing, so the $1, $2, $3 pricing, that first year made over $84,000.

Andrew: Wow.

Jason: Just myself wearing t-shirts. But as you alluded to, I worked every single day. I was on social all day, I made a video every day. This is before the Casey Neistats of the world. This is before everyone understood what Instagram influencers and YouTube influencers were like. It just was me being a weirdo in Florida, wearing a t-shirt, promoting on social media the best I knew how and just trying to have fun. I mean, that was really the whole idea of it. But yeah, as you alluded to, like, it didn’t work out long-term.

Andrew: Why not? It feels to me like you’re talking $1.2 million on a t-shirt wearing business . . . Yeah, it’s over five years, I would think it wouldn’t be maybe a huge hit, but that seems like a success wear. What was at your height? What was the annual revenue?

Jason: Yeah. So, first year, it was just around 85, second year, about 200 because I doubled the price, went to a second person, third year, just under 500,000, and then fourth year, just over 500,000. And so I scaled up to five people wearing t-shirts in the third and fourth year. But the problem was, is that the expenses were a fixed amount. So I had seven people who I was paying, myself included, which was the lowest of all of them, hilariously, as most founders find out with.

But the variable of revenue was very low in the beginning of the year because of that bump sale pricing. So I had, like, $30,000 in payables in January, but I made $1500. That really led me into . . . Like, I had banked a lot of cash from the first two years. I didn’t spend it all, but at $30,000 every month, that quickly ate into my cash. And by the third or fourth month, I was broke. I had no money to pay everybody. Even when the calendar was selling ahead of time, it just ran out and I didn’t have any cash, and that kind of killed the business.

Andrew: And then how did you handle it when you didn’t have enough money to pay people?

Jason: I did a couple of things. I begged family for money, and luckily, I had an amazing bit of family that, you know, had some money they could lend me and, you know, I didn’t ever get a chance to pay my grandparents back. You know, they were able to just forgive that. They were like, “Hey, you know, we looked at it as giving you a chance to succeed.” And that’s tough. Like, those are some of the decisions that you make when you run your own business that you don’t think about and that can carry weight for a long time.

But, yeah, in 2013, when I finally decided to shut everything down, I truly felt like a failure. Like, I just honestly felt like I spent five years of my life, all this time, like, 1,600 videos I created on YouTube, all of these accolades, interviews with people like you, and being on the “Today Show,” and other stuff like that. But for what? I had $100,000 in debt when I finished that business, and I just felt like, I can’t hack it, you know, as a business owner. And so, yeah, there were just a lot of revelations there about, you know, trying maybe to run, like, a more standard business or to create something that was more simple where I’d have to show up every day.

Andrew: Don’t take this wrong way. You know I like to be open and have, like, open engagement. Were you a failure then? Like you said, you felt like a failure. Maybe it was a failure. You were a failure. Five years of doing this and you are $100,000 in debt. Your grandmother is even taking a hit on this.

Jason: Yeah. I think two things happened. Number one, I don’t think I knew enough about business, just in general. Like, I don’t think a lot of entrepreneurs actually learn profit and loss, and expenses, and how to manage money, and how to manage people. And there are so many variables that I just couldn’t figure out fast enough because every day I was still filming, hosting a live show. Like, I was not only running the business, I was a piece of the business, you know, constantly going. So I think that was the first thing.

And I do think the second thing was a little bit of I grabbed a really great time in social media. Like, to me, those were, like, the peak years of social media growth. I think now, it would be so hard to do IWearYourShirt now because it’s not different at all. Like, there’s so many people doing some variation of it, so it just wouldn’t work. And I just don’t know if that business had a long-term.

Andrew: I don’t know about that. I don’t know if it does have a long-term thing. But are there people doing variations of this that I’m missing out on?

Jason: I think vloggers all pretty much do this on YouTube. Like, people who make daily videos on YouTube or even weekly, I think they do exactly what I was doing without the promotion of a company. They’re just shit . . . Because that’s all I was doing. While I was promoting the company, I was really more . . . I had an hour long live video show every day. I barely talked about the company. I just talked about my life. And so I was not, like, live vlogging my life, and that’s what everybody’s doing now.

Andrew: I get that part, but I actually feel like the hook was, we’re all watching you, get more money from this. And that’s kind of interesting. The other part of the hook was, were there people paying you just to wear a t-shirt? And it was a very creative thing. I actually don’t know that people are doing this. Yes, vloggers are showing their lives publicly, and that part is the same. But that hook of, I’m getting paid to wear t-shirts. Let’s see what I do with this is kind of interesting. I could see it even working today, with more established mediums picking it up like Instagram, like, YouTube.

I could also see that one of the models that . . . One of the things that I loved about your model back then was, everyone whose t-shirt you wore had an incentive to promote what you were doing. It’s like, “Hey, look, I just paid this guy to wear a shirt.” They would promote the fact that you were doing it. And that was a nice built-in promotion mechanism.

Jason: Yeah. For sure. I mean, I definitely leveraged all of those things. You know, as soon as the company would come on board, I’d email and be like, “Hey, how often you get someone to pay your shirt?” And they reply back, “Never.” And I go, “Okay. Well, post about it on Facebook.” You know, like, it’s marketing for you, just to say that you did this. And that did lead to a lot of the growth. It’s why, you know, in the first year 10,000 people came to the website every single day. And they just wanted to see what shirt I was wearing, just like you said. You know, in some ways, I do think you’re right. I think it could succeed today. I think I’m so jaded, just because I spent so many days consecutively working so much time.

Andrew: That’s the part that sucked. You were doing it all live. And that’s the part that made it fascinating for us to watch this hamster on a wheel until the hamster fell apart. But until then, the hamster on the wheel is really fun to watch.

Jason: Yeah. Yeah. And I think, you know, if I was to do it now, I would take weekends off, be a week or two ahead of myself. You know, batching, we all know about that.

Andrew: We don’t want to see that. We want to actually see whether you’re going to fall or not. If you think about Casey Neistat, it was interesting because he would do it even on the weekends. That idea that he’s taking it to a limit. All right, maybe weekend’s off, but we’re not going to let you build up a backlog. We want to see Candace actually kill you or not. I get that. I remember that you had other people doing it. I wonder, were they able to keep up with the work that you were doing? Were they able to do this every single day be out in front, have something to say, even when they were sad, even when they were tired?

Jason: It was tough. It was tough on them. It was a lot to ask of someone to show up 365 days a year and put on a face, you know, for a company because that was the other big thing too is you can’t really have a bad day when you’re wearing someone’s logo and they’re paying you to do it. Like, when you’re vlogging, have a bad day, that’s part of the story. But when you’re representing Pepperidge Farm, as a company like Pepperidge Farm is going to be pissed if I show up and I’m not having a good day. And that does take its toll.

I mean, I remember having lots of conversations with the people that, you know, were awesome at their jobs at wearing shirts, but they had a bad day, they went through a breakup or, like, we had to give a pep talk. And be like, “Hey, you got to show up.” And that’s tough. That’s a lot to ask of people.

Andrew: I know. And I hate having to give people pep talks about it. I’ve got to tell you. I’ve had really bad days, where they were family issues. I show up here and I do interviews, you can’t tell today I’m having a bad day. You can tell that I’m actually really happy now that we’re here. As soon as we’re on, I’m on. But I’m having a bad day because we clustered way too freaking much this week. Every minute of my day was scheduled for all four days. Tomorrow, I have a little bit of time off because I’m going away next week, but I can still show up. It’s hard to find people like that. And it’s hard to know whether somebody’s got that until you put them through it, right? You don’t know if somebody can finish the marathon until you get to mile 22 and that’s when you start to see what they’re made of.

Jason: Yeah. Absolutely. And also, when you run your business, no one is going to [inaudible 00:11:24]. We all know that, right? So you can find star performers, you can find rock stars, and I really do think I did in all the shirt wearers I was able to hire, but, you know, I cared more about the business than they did. I had more to gain from the business succeed than they did. So they’re only going to work so far and then they’re going to go, “Okay. Like, I’m done for the day.”

Andrew: And also I think the fact that you are paying them salary is shocking. I would have thought what you do is say, “We’re going to get paid based on results. So January is going to be painful. December is going to be glorious. You’re only going to get to glory if you suffer through the pain. You got to make it through July to get it.” But you’re smiling and laughing that off. That actually is a good model. I think maybe you’re too nice of a guy.

Jason: Yeah. Well, and I just think that that’s also part of running a business where you decide, what do you want the culture to look like? What do you want things to look like for people? Do you want people to constantly be hungry and like always have to do that? Maybe that works for some people. I just wanted people to really enjoy the fact that they were getting paid to wear t-shirts for a living. So I didn’t want them to feel like, “Hey, you have to perform and earn your money.” I wanted them to feel like, “Hey, the money’s fine. You know, you have a salary, you’re comfortable in that. I want you to have the freedom to create every day and not have to . . . ”

Andrew: That’s a mistake. I feel like that’s a mistake. Am I right?

Jason: I mean, it’s hard to say whether it would have worked better or not. You know, like, maybe it would have crushed their souls. It’s very difficult to know that.

Andrew: That’s great entertainment for people to see that their souls are crushed. Like, “Look, the agreement is when you break, and when you fall off the wheel, we have to talk about it. And maybe then what you get is a little bit of money to get off the wheel. But until then, you got to keep going.”

Jason: Yeah. There’s no doubt about it. One of the original ideas that we had when I went to five people is to how to be almost a reality show, right? And so you would click the person on the website and you could see what was going on in their lives. And you’re totally right. I mean, the more interesting thing is when you’re pushing people to the edge, but that just wasn’t in my nature. Like, I’ve never been that much of someone who, you know, cares about those things. I just really wanted to tell stories and to have fun doing it, and to just be this weirdo who was wearing t-shirts for living, and just had this kind of crazy business that people looked at him and was like, “What? How can you do this?” Because I always loved those businesses, like, the Million Dollar Homepages of the world and those things.

Andrew: That’s kind of what inspired you. By the way, I didn’t know your background. One of the things that I always admired about you was, this is the smallest thing, but I think it says a lot. The photo that you had when you were doing IWearYourShirt was you with a miniature t-shirt that’s like cardboard in your mouth that said IWearYourShirt on it. So I could see the logo in your mouth, which made it a little bit more interesting, but it was also like a t-shirt. I wondered, like, how did you get that? I know this is like a very petty, small thing to bring up, but I think that your design sensibilities extended to that little thing and I wondered how you put that together.

Jason: Yeah. I care about the details a lot. And I think that a lot of times, that’s actually what can separate someone who has a good idea to someone who has a great idea is it can be the same idea, but it’s the details that actually make it stand out. It’s the branding, it’s the experience, it’s the little things like my t-shirt business cards. Like, I just had an idea of, “Wait, all these little stuffed animals have t-shirts. What if I just, like, get rid of the stuffed animal part and use these as my business card?” And those things were like $3 apiece. Like, they were not . . .

Andrew: Oh, these were business cards that you had printed up that said . . . ?

Jason: Oh, yeah. I had it in my backpack when I would do public speaking and I would give them out afterwards. And it would cost me like . . .

Andrew: Three bucks.

Jason: $3 to give out like 100 of them. But everyone took photos of them at the time. Everyone talked about them. Like, no one takes photos of a business card and, like, shares it. They’ll keep the photo, but yeah. I would get pictures of those things showing up all over the place and it was just a great thing of marketing. So I’ve always had kind of an eye for those details. I really care about the details. And I try and think . . . I think that’s what makes a weird idea work is not just that the idea is weird, that you also can execute it to a degree that someone goes, “Oh, Wow. You really thought about everything here.” And that’s what kind of makes it worth talking.

Andrew: Give me an example of something else that you’ve executed. You can go even forward in the story and then we’ll go backwards to how you got started. But give me an example of some weird thing that’s made better by you because you care about the details.

Jason: Yeah. So look at, like, when I sold my last name for the first time, you know, I could have just done an eBay auction because that would have been weird. It would have been on eBay. This is the guy’s last name. But instead, I had it built. Like, I had my own auction system built. I paid a developer to do it. But then it wasn’t just, “Hey, I’m going to change my last name online,” which would be easy. I could just go into Facebook, and go into Twitter and, like, update these things.

No, I went to the courthouse, I sat in front of a judge, I hired a lawyer. I changed my name legally. I went to the DMV and sat at the place that we all hate, and I changed my name legally so that I could have that license to take a photo of. And that’s why things like “USA Today” and the “Today Show,” these businesses and media outlets said, “Yeah, we’ll have you on,” because I go further than just, “Oh, I just changed it online,” and not a big deal. So those that just go one step further that most people won’t do.

And it’s awkward. Those things are tough. Like, that’s the opening of the book “Own Your Weird,” is the story of the first time I sat in the courtroom getting ready to change my name. And I was so nervous, I thought it was going to, like, go to jail for changing my last name. I did nothing wrong, but it just was, like, putting yourself out there, those comfort zones that you kind of break out of, that’s what ends up being some really great stories that people can tell and become marketing for you.

Andrew: I want to come back and talk about how you changed your name. Let me make sure that it’s a really big letters in my notes here. But before we get into that, you’re a designer, which I hadn’t known before. And you did some work for Kanye West. How did Kanye West become a client of yours and what did you do?

Jason: So, yeah, I graduated with a degree in design from college, got a 9:00 to 5:00 job. So, for three-and-a-half years, I just worked in the corporate world, didn’t do anything weird, didn’t do anything unique. But I had a friend who also hated his 9:00 to 5:00 job. We kept meeting. We were having burgers and fries every Thursday. And we just were talking about how much we hated our jobs. And it was just like an outlet for it. And one day, we just were like, “What if we start our own design company? Could we do that?”

He was an incredible designer, still is an incredible designer. And I was like, “Well, I think I can handle the client-side. I’m not as good at design as you. So why don’t I just try and get us clients?” And really, that was just me emailing friends, which is actually how IWearYourShirt got started too. But I was just emailing friends and say, “Hey, do you need a website? And this is 2007, 2008. So we’re like, you know, crafting websites back then you’re on Dreamweaver, whatever.

But, you know, the guy, Dennis, was such a good designer. So he was really a fan of The Brilliance, which was a blog that was huge back in that time. And they brought it back recently. It was dead for a few years. But it’s these three guys. Chuck, Ben, and Virgil. Virgil is now . . . He worked with Kanye for a long time and now Virgil’s, like, super famous in the fashion world, like, really well-known. But back in the time, in 2006 and 2007, I had no clue who the people were. I just knew that Dennis loved them.

So I emailed them and was like, “Hey, my co-founder loves you guys. If you ever need design help, we’d love to help do something, even for free, just to work with you.” And I remember I became good friends with Ben over email. And one thing led to another, he was like, “Hey, I think that Kanye actually has some work that we needed.” And we loved Kanye, of course. And it ended up being his Myspace page for the “808s & Heartbreak” album, which is just so funny, right? Like, that date set of that time, like, the big thing was designing his Myspace page. So we didn’t get to work with him. Spoiler alert, we worked with the Universal, the record label, at the time.

Andrew: But you did work on his projects through somebody else. And this got you kind of started. And then what did the idea for IWearYourShirt come from?

Jason: So, as we grew, I mean, we only had, like, 10 or 15 clients with that small design company because we were two people. We didn’t need that many. But as we grew, people started to see that I kind of had a mind for marketing. Like, we’d have calls and we talked about design, and I would just throw ideas at them for different things they could do that had nothing related to the design itself, just more their business. And so then people start asking me like, “Hey, Jason, you seem like you’re kind of cutting edge,” which I wasn’t, “but what do you think about Twitter, and Facebook, and YouTube?” So this is 2007, 2008. I had no idea. Like, I had a Facebook account, but I never used it.

And I went and looked at all these platforms, and I started to see, “Wow. This is interesting.” There’s so many people in here, already, that are just sitting around and talking. And then I have brands that I’m on a literal phone with, this is before an iPhone, so I had to hold the phone. And I’m talking to these companies, I’m like, “Wow. these brands want to be in front of these people and there’s no way of that happening right now. What if there was some one in the way?”

And I think, probably, I was watching like an infomercial at the time, late at night. I was like, “Oh, this is happening on TV.” And you hear on radio, “Oh, this is happening on radio. This isn’t happening on social media, someone promoting these brands to these people.” And so, yeah, you know, for some reason or another, I thought I could do it, even though I didn’t use any of these things, but they just looked accessible enough. And yeah, that was really the spark that led to it. It was these clients basically saying like, “What should we do on social media?”

Andrew: And the brilliance of it was not let’s buy ads on people’s pages that are the same as banners, but let’s be a part of it, and I will be the crazy thing, the weirdo who’s going to get you there.

All right. Let me talk about my first sponsor, then come back into the story. My first sponsor is a company called HostGator. If you Jason or anybody else is looking to host a website, you owe it to yourself to go check out, especially, if you’ve got a crazy idea that you want to bring to the world. Jason, did you have any crazy ideas that didn’t go anywhere, that you just launched to the site and when you saw it, you said, No, not really?”

Jason: Yeah. My buddy, Paul Jarvis and I created a site called EmojiBombs a couple of years ago. And it was basically, we wanted to write the backstories to the emojis that we all use so that there could be, like, a full backstory to each one of them. And we got about seven or eight into them. And we did this in like a 24-hour build. And then we gave up. Because we were like, “First of all, this is ridiculous.” And we tried to get people to pay in advance to, like, hear the stories. And, like, no one wanted to pay for it, obviously.

Andrew: Did you get to do the domain for it, the whole website?

Jason: Yeah. We had EmojiBombs. We had a website, we had a logo, we had everything for it. I think this was a couple of years ago. Now we let it all die.

Andrew: I’m on the site right now. Actually, it’s not fully dead. I don’t think . . .

Jason: There’s still some stuff. Yeah. There may be some stuff on our site that we kept. Yeah.

Andrew: What was the big downside of having created it or the upside of having created it and then having it go nowhere?

Jason: Yeah. So what I really love about weird ideas, especially like EmojiBombs, one that doesn’t work is it’s not necessarily that site has to be successful for it to be a successful project. It’s the fact that we did it and we can talk about it. So at that time, Paul, and I were just interested in drumming up some attention for our creative work that we were doing, whether it was online courses or other things that we were building. And so we just wanted something that would capture people’s attention.

So even though EmojiBombs as a business failed, we kind of knew it was not going to be successful, but we were just going to try it anyway. It drew a whole . . . I mean, thousands of people came to that website in the first week that it existed, that never would have seen our stuff. You know, we promoted it on Product Hunt. We did all of those things. And so it created this marketing buzz for us. And that’s where I think that some of these weird ideas, they can have a lot of legs that you don’t even see or unintended outcomes that you don’t see. Which is why, for me, like, I love owning my weird. It’s why I wrote the book. It’s why I live this ethos because it does have unintended benefits that you don’t even see just by putting yourself out there.

Andrew: That’s not at all what I was expecting, but I’m glad to hear that. What I was going to say was, I found that even the things that don’t really work for me, helped me learn something. Like, I was creating videos of all my past interviews when I got started and it was painful for me to stop doing it, but I didn’t have enough time to do that and the interviews. And still, even though I considered stopping it a failure, I learned so much about video editing from it. I now know enough that I can know what I’m asking people when I need video edited. It allowed me to create courses which create videos with entrepreneurs who are coming on and didn’t know jack about publishing, I would do it.

So even the failures end up teaching me something. But you’re right. The way that you do it because the ideas are so weird, so our there, so creative, so innovative, so weird, they end up getting you attention. And so I’m going to say that to anyone who’s listening to us who has a couple of weird ideas, things that maybe are going to go somewhere, maybe not, take them over to HostGator. It’s super cheap hosting. When you go to, you get the lowest price they have available. Put it on there. Sometimes when you start to create the idea, it takes a life of its own and goes different from what you imagine. Sometimes when you put it up there, it’s kind of stupid, and you want to shut it down.

The failure is not starting, the failure isn’t putting it up there and then seeing that it doesn’t work, and closing it up. It’s totally fine, start it, close it up, move on to something else, learn from it, share it, whatever works for you,, super low price. It will allow you to create websites fast, lots of them, if you want to. Kill the ones you don’t love and continue with the ones you do.

I can read you a feature list and they got feature list up the butt. That’s wrong for me to say. They’ve got feature list up the wazoo. Everything you need is in there and they’ll scale with you. But frankly, just go to because it’s low price, you’ll be supporting me by using that URL. And it just works. It’s hosting that works.

All right. So you had this idea. You started selling t-shirts, you started getting people to pay, you started posting. We were talking about that in the ups and the downs. When you closed it, let’s jump over to that. How did you announce it? I don’t know how you announced it to the world. And how did you announce it to the people you were working with?

Jason: Yeah. I mean. It had been a slow enough burn that I don’t think, like, you know, many people were too surprised because I had to let all the shirt wearers go that were working for me toward the end of 2012. I just couldn’t sustain the salaries. So I think it was, like, August, 2012, I let all of them go, which was really hard because I let them go on Skype. Like, we were all virtually working. I mean, it’s not like I could fly to their towns and let them go face to face, even though I would have liked to have done that. Again, I just care a lot.

But once people started to see that they were going . . . I mean, and this is also where, you know, you talk about watching the reality happen and then people really knew that things weren’t going super well with IWearYourShirt. And that’s when I basically just said, like, “I have to go away from this calendar model.” First of all, I’ve now worked almost 1,200 days straight, at that time, like, literally, 1,200 days straight. And I just have to take a break.

And so I kind of took a little bit of a break, like, a couple of weeks off. And then we just kind of redid the IWearYourShirt website to be more video creation company. And I didn’t even know what we were going to do. But I just knew we still had a bunch of sponsors that wanted videos. We still had people who wanted exposure and for us to create stuff. And so that’s what we did, and kind of strung that along for about six months.

And then I just knew that the writing was on the wall. I couldn’t make enough money from doing these kind of one-off videos from companies. And also I was just so burnt out, Andrew. I did not want to open my camera. I didn’t want to put a smiling face on. I just wanted to be done with that project.

Andrew: It’s what I imagined.

Jason: Yeah. And so, in May of 2013, I put up a post on Facebook, that was the big thing, I put up a thing on the IWearYourShirt website and just said, “Hey, I’m taking a break. I’m not dead, I’m okay. But I’m also not feeling great either. And I just have to be honest that things did end well. And I didn’t even admit I was $100,000 in debt, you know, both, like, my grandparents and just credit cards. I had maxed out, like, nine credit cards to keep paying for things.

And I had to figure out how to take care of that because IWearYourShirt was not going to be that thing that did that. And that was kind of, like, a period of exploration for me of just figuring out, “What do I want to do next. Like, Who am I? What can I bring to the world? Am I ever going to have another good idea?” Kind of, like, a little bit of a midlife crisis at that time.

Andrew: I get that. How did you deal with it? What was the thing that allowed you to . . . ? What was the worst thing that you did, in retrospect, during that bad period and how did you get out of it?

Jason: I mean, I’d like to say the worst thing I did was I ate Chick-fil-A every day for, like, six months straight because I . . .

Andrew: Did you put on weight? Because I remember you as a fit guy.

Jason: I put on 50 pounds.

Andrew: Wow.

Jason: Yeah. Luckily, I’m six foot four, so I could hide it well. But I mean, like, you can find, I did a 90-day challenge to finally get rid of that weight because I was just so upset with myself. But yeah, I mean, I put on a bunch of weight. I couldn’t sleep. You know, I think it was probably some of the darkest time for me of, you know, this business kind of dictated my life. I put all of my self-worth . . .

Andrew: You couldn’t sleep because you thought the world thought you were a failure or because you thought you were a failure? What was going through your head that kept you from sleeping?

Jason: Well, the thing that kept me from sleeping the most was the stress and pressure of money. So, you know, when I got rid of the salaries, you know, that took a little bit of the weight off, but then I had all this debt. And so that was staring at me, you know, every single time I logged in any site that had any money related to it. I always laughed at my like, you know, you have the pie chart where it’s like, “Here’s all your assets” and, like, mine was just all red. It’s just it’s like a gnarly red.

But yeah, it was really tough. I mean, I can make light of it now. But I remember I had a speaking gig that I still had booked and I had to show up for it. And I got on stage and it was just right before I was shutting down IWearYourShirt. And it was like this, right? Like, they want to know like, “Oh, what are you doing? Like what’s going on? Blah, blah.” And I finally told the guy, I was like, “I can’t sit up here and pretend like everything’s okay. Like, I have to be honest with where I am right now.” And I just, like, blacked out for the rest of that talk. I didn’t physically blackout but, like . . .

Andrew: You don’t remember what happened. You were just speaking.

Jason: I just was speaking from the heart. I was being emotional. I’m never emotional.

Andrew: And you admitted openly how it was?

Jason: I admitted that I had debt. I admitted that I, you know, thought I was a failure. I admitted that, like, I couldn’t just look at a video camera anymore as weird as that sound.

Andrew: Yeah. I get it.

Jason: Yeah. And I finished that talk. And, you know, you would think like, okay, everyone’s going to be like, ” All right, get off the stage.” Like, you know, bummer. But people stood up and applauded. I mean, people came up and gave me hugs afterwards. People basically just said, like, “Wow. Thank you so much. Like, it’s comforting to see that someone who has had all these great accolades actually goes through this crap that I’m going through in my own life, in my own normal day to day.” And I think really, that was the first time that it showed me that I could be vulnerable, and I didn’t have to feel guilty about it. I can actually feel empowered by it. And I could be honest with people and say, “Things are going perfectly,” and people aren’t going to, like, scatter like bugs when you turn the lights on.

Andrew: And then, what did you do to get yourself out of it after the Chick-fil-A period?

Jason: The Chick-fil-A period of 2013. Yeah. Honestly, I think two things probably helped the most. Number one, an amazingly supportive wife. My wife, Caroline is just so unbelievably . . .

Andrew: Were you married . . . ? You got married while you were doing this?

Jason: We got married in 2017, but we were together through pretty much almost all of it.

Andrew: Got it. Yeah. I do remember saying, how is this guy going to get, like, a date when he’s that visible online? And then you told me I think, at the time, that you were dating somebody. Okay.

Jason: Yeah. I was lucky because I don’t think I would have had any time to, like, swipe app at all to find anybody. Like, it just wouldn’t have happened.

Andrew: And then also, at the time, it felt a little bit weird to be that open, but who knows, maybe that would have attracted somebody to you. But I got it. I felt like, all right, the one safe thing that he has, in a very weird environment with no break is at least he gets to go and be with someone at the end of the day and decompress, instead of feeling lonely after the cameras are off. I do remember that being a little bit comforting to me, for some reason. Okay. So you had your wife and you were telling me about how you snapped out of this.

Jason: Yeah. So she was incredibly helpful. I mean, just I could, you know, talk about all these things with her or try to. I mean, it still was really hard for me to be emotional or to speak about any of this stuff. And then I had lunch with a guy, not Chick-fil-A, actually a different restaurant. And he kept asking me if I would write a book. He’s like, “You got to write a book about this story. It’s such a good story. You’ve learned so much stuff.” And I felt like, “How can I write a book when the ending really sucks?” You know, no one wants to read the ending of the hero ends up not winning the day.

And he said, “Why don’t you let the end of the book figure itself out? Why don’t you just write the first part and see what happens?” And I drove home from that lunch. And actually, the first thing I thought about was not, “Oh, what could this book be about?” It was, “Oh, could I do this in a weird or interesting way? What if I got sponsors to sponsor every page of the book?” I already had a whole bunch of experience with sponsors. And then that became exciting because it was a money-making opportunity. I could make some money. It became something where I could, like, you know, kind of like push the industry in a different direction I’d never seen before.

Andrew: The fricking cover even had a sponsor, right?

Jason: Yeah. Yeah. Treehouse, an amazing company.

Andrew: Ryan Carson, yes. Still doing great. His business. You know what? Here’s the thing about you that I’m watching you, I’m interrupting you, as you’re telling this because I’m watching your whole body change as you get into the creative part of it. Like, the creative part is so such a draw for you, instead of the business part of it.

Like, I remember, actually, when I was trying to figure out where Mixergy’s revenue was, I don’t know if I contacted you, or maybe I wanted to with the idea that I said, you know, I’m doing videos all the time, I was doing them live anyway, for these interviews, I’m doing one a day. I think that having you sell t-shirts on me would be interesting. I don’t want to sell them, but I would wear a t-shirt in every interview and then we have that. And I thought that’s kind of an interesting model since human beings now are the asset that’s being published. Maybe he’s got a new type of banner ad that you can click away from.

But I thought it was me not reaching out to you that kept that stuff from happening. It turns out, it’s just that’s not the way you think. You’re not thinking like Gary Vaynerchuk. I’m building a lot of attention so that I could then day trade it as he calls it, sell something to it. You’re thinking, “This is such a creative project,” right?

Jason: Yeah. Totally. Yeah.

Andrew: That’s who you are.

Jason: Yeah. I get so much personal fulfillment from . . . And I don’t mean to just keep shilling it, but it’s true. It’s owning my weird. Like, I get so much personal fulfillment with the idea.

Andrew: No, I get that.

Jason: Being creative and executing it. Honestly, as much as money is nice and it’s helpful to have, I don’t get fulfillment from making gobs of money. Like, it just is not something that fills my . . .

Andrew: Our producers always ask our guests, “So what was the business you had growing up?” We just kind of check out to see people’s enthusiasm and memory, though. You said, “Look, I’m not that traditional entrepreneur person. Yeah, I did have a lot more thing at one point, I quit pretty fast.” It’s not who you are.

Jason: No, not at all. Yeah. So getting back to the book story. When I wrote that book, that was so cathartic to me to just air out everything. And luckily, I had an editor who was like, “Well, we can’t really, like, bash this person or this company that was horrible on the backside that no one saw, because they are well-known. They’re like a Fortune 500 company. Let’s not do that. You can get sued.”

But there were those instances, there were those things where I’d held all of that in and I’d not talked about it at all, and writing it out, even though I was a terrible writer in my first book “Creativity For Sale.” I look back and I’m like, “This is an embarrassment.” But I think we all look back in our early work as embarrassing as we should. But it helped me so much just writing, getting all that out of my head, getting it onto a paper, Word doc or whatever, was so, so helpful.

And then the creative part of the project, like you said, like, that lit me up. That got me excited because just writing and publishing a book, it would not have been fun for me. It wouldn’t have done anything for me. But the sponsorship part, trying to get these sponsorships trying to come up interesting . . .

Andrew: That got you . . . That was fun again.

Jason: Yeah. I built a whole website, And I could make all of these cool ways of, like, people knowing, “Oh, there’s these sponsors are getting talked about,” but it’s not going to look like ads you, like, cut out of a book. Like, it’s going to look seamless and fun. Again, the details, right, going back to what you talked about earlier. And you can read it through on Amazon, people will say like, “I expected to hate . . . ”

Andrew: I’m going to read it right now, actually. “If you’re at a crossroads in your life, this is the perfect book to pick up. I’ve been unhappy in my career for a long time and I know I’m not doing what I meant to be doing, the passion is gone. I’m not kidding you.” And he goes on.

Here’s another person, 64 years old says, “The last portion of this book made me realize that I also have an emotional void that I fill with things that I purchase just to purchase them, had attempted to build a t-shirt business back in the ’80s, but that led to a vehicle.” And it goes on and on, and on. And this is what people said. This is, like, the connection that you had with these people.

Jason: Yeah. Yeah. I mean, you want to say, like, you’ve written a book, and it’s a best-seller or whatever, and that’s all fine, and well, and good. But those are the things . . . I get those emails. Like, people who don’t leave reviews, they just email me and still email me, those are the things that I love. Those are the things I’m so happy about. I’ve got a swipe file, you know, on my finder where I just grab these emails, I screenshot them, I save them. And when I’m having a bad day or when things aren’t going well, I’ll just peek in that folder and feel good about myself, and go oh, . . .

Andrew: I need to do that.

Jason: . . . I am making an impact. I am doing things. Even if today, the numbers are down or the business idea isn’t working or revenue is, you know, taking a hit. Let me go back to actually what fulfills me up and, like, makes me happy.

Andrew: Let me get into a little bit of gossip here. Evan White, you guys were partnering up. He was your PR person, then he became the second person to wear a t-shirt. What happened there?

Jason: Yeah. You know, I think Evan would admit too, we were both a little bit naive about what was going on and how IWearYourShirt was working and, you know, all of the different things. And we had a verbal agreement of ownership of what that could look like with IWearYourShirt.

Andrew: From the beginning? From the beginning?

Jason: From the second year, when he started wearing shirt. You know, because Evan wore them for the whole second year with me and did a great job with it. He tore his ACL through it. And, like, you want to talk about seeing the real. Like, he had his surgery while wearing a shirt.

And yeah, I mean, he was an incredible worker, an incredible guy, super creative guy as well. But I think we had some conversations. And again, this goes back to, like, I just didn’t understand business. And we talked about percentages of ownership. And we never wrote it down. We just were having conversations. And when things started to go south and when things weren’t going well, you know, it almost just seemed like he was still trying to show up for money or for ownership, and I was just trying to survive. And it just didn’t go well.

And those conversations, I think, especially when one person is carrying all the weight to everything, you know, it’s really easy to be the person who doesn’t have to answer all the emails, and do all the work, and manage all the people, and all the things. And that led to a lot of consternation between us. And eventually, we just kind of fell apart and we had an amicable separation. Finally, we got lawyers involved and wrote up an agreement, and agreed upon, like, a very small settlement of sorts, if you will. And it sucked.

Like, I really do hate it because I talked to Evan every single day for almost two years straight on the phone. And we were really good friends. He came to my place, I came to his place. But I’ve found that over the years, this tends to happen with founders. Like, you can fall apart. You can have the business tear you apart. And that can be part of the game. It doesn’t have to be, but it certainly is something I’ve learned to structure relationships differently when we’re starting, get terms nailed down, be more realistic about terms and understand what kind of the long-term that that looks like.

Andrew: All right. So let me talk about my second sponsor and then we’ll get back into why you decided to change your name. And the first name change happened before the book. The book, I think, corresponded with the second name change. Am I right about that?

Jason: Yes. Yes. You are.

Andrew: Okay. The second sponsor is a company called Toptal. One of the people who I’ve gotten really close with because of these interviews, a guy named Justin Hartzman. I connected with him before doing my interview with him. And he’s really good about texting out of the blue. Are you good at texting out of the blue?

Jason: No, not at all.

Andrew: I suck at that. I don’t know where the guy gets the nerve to text me or, like, the guts to text out of the blue and go, “Hey, how are you doing,” or whatever, thinking that . . . He’ll add like, little things about whatever. He’ll even call me out of the blue, “I’m just driving to pick up my daughter from school, wanted to say hi.” Who the fuck does that?

Anyway, because of that, I’ve actually become friends with the guy. I actually really enjoyed talking to him. And he’s the guy who runs a company called Needls. I interviewed about how he has this automated software for placing ads and so on. He then just gets into crypto, like every fricking person. I feel like crypto is a magnet for a certain type of person. He’s, like, the hustler type of guy. He’s the guy who has to have a bunch of companies and maybe some real estate on the side and more.

So he gets into crypto. He creates a company called CoinSmart. Now he has a team of people at Needls, says, “You know what? CoinSmart, I’ve got really good people. I’ve got really good money in this business. I need to have somebody to watch them and give me some feedback, and give them some feedback.” He goes to Toptal, he says, “Andrew, I’ve heard you talk about Toptal.” He calls up Toptal, well, technically, types in their URL, I hope it’s /mixergy or else I’m deleting the fricking name from my phone. But He hits that button and he gets on a call with a matcher. And what he asks for is somebody to come in and overlook the work that his new developers are doing on a site called CoinSmart. And I found that there are many people who have access to developers, have access to a network of people who get them developers, what they really appreciate about Toptal is that Toptal has the best of the best.

Even if their whole team isn’t Toptal, having some high-end people look over the work from Toptal, guide them, create something for your company that they’ve already done for other companies will be a huge win. So, Justin, is one of many people who I’ve interviewed. Derek Johnson is another one who I’ve interviewed. Many, many people who I’ve interviewed, many people who’ve listened, have signed up for Toptal.

If you’re out there listening and you need a developer, you’re going to try every other way. I’m not going to tell you not to. I’m not actually going to pretend that you’re not going to. You’re going to try everything else and then Toptal will be your last choice. When you say, “Okay. I’m tired of this. It’s not working. I really don’t love the people I get.” Toptal, one phone call with them, they’re going to put two or three people, in my experience, two or three people in front of you, you will see that they are almost perfect matches. You’re going to struggle to figure out who to hire. And when you hire the one that you want, you’re going to love them. And if you don’t, they’re not even going to charge you. Really, get details on this.

Actually, Jason, this is why I actually have to read the exact thing because they want to make sure that I’m saying this exactly right if I’m offering it. Here we go. Mixergy listeners are going to get 80 hours of Toptal developer credit when they pay for the first 80 hours, in addition to a no-risk trial period of up to two weeks. If at the end of the period, you’re not 100% satisfied, you will not be billed. Nobody does that. Really top as in top of your head, tal as in talent And if you want to know how it works, just text Jason or text Justin, excuse me. Text Justin, say, “Hey, Justin, how are you doing? Just thinking of you. By the way, how’s Toptal out for you?” His phone number is up. I bet he’ll even love it.

All right. Are you, like, a friendly person? I know you travel a lot as a kid and that helps you become, like, better with new people. Are you somebody who talks to strangers?

Jason: Yeah, I don’t I’m, like, the most extroverted person ever, but yeah, I don’t mind. I don’t mind other humans, most of the time.

Andrew: I talk to strangers. I’m not good at talking to friends.

Jason: Yeah. I think it’s just one of those things. Some people really are thoughtful about friendships, and they want to stay in touch. Like I had a good friend, Dru, who would, same thing, like, call me out of the blue or whatever. I’m like, “How does he think about this.” And I think it’s just, they think about it. They just did natural, whereas, we’re in a different brain space somewhere else thinking about other things or whatever, and it just doesn’t even land for us.

Andrew: I feel like we are bad friends for them. They probably go off and find other people who think about them. The one thing that I’ve done recently to kind of stay in touch with my friends, I did a project with them. I did this push up thing where I was trying to get to 100 pushups in a row and I got the app for it. And I brought in a few friends on iMessage. It just kind of built up to, like, four or five people who are doing it and then I hit 101 pushups, and then we were all done, right? But I did it again. And now it’s giving us something to chat about. Now, we’re not just talking to say,” Hey, how you doing?” But it’s like, “Here’s my number, I posted today. You get to give me a thumbs up,” or whatever. And then we check in with each other a little bit and we move on. Give me a project to talk to you about, I’ll talk to you. Just chatting, no.

Jason: Yeah. It’s fun, though. Hey, congrats on getting to 100, I tried the 100 pushup challenge, and then I got to, like, 60 and just gave up.

Andrew: That app is really good. I think if you find the right app . . .

Jason: I did it back when it was only a PDF. So I think I need to try it again with the app.

Andrew: Here’s what the app is good about. It builds you up slowly. And in a reasonable way, it forces you to work long-term. It’ll take like two months to get to 100. And I’m good at that, as we talked about. And I do find that it helps if you’re kind of texting with people. If you want it on this group, I’ll text you in, then we’ll have a reason to talk. But don’t say yes if you just want to, like, hang on the wall. Don’t say yes. All right, let’s go into name change. Where did you get the idea to change your name, the first time?

Jason: I got a text message from my mom asking if we could hop on Skype in 2012. And I had never Skyped with my mom before. So something was up. And we hopped on Skype and when I saw her face pop up, she was crying. And it was a really tough moment. I mean, I was already going through crappy stuff in business, at the time, in 2012. But to see your mom crying and emotional, like, that was really tough. I grew up with a single mom. So, you know, especially, it meant a lot to me.

And she said, “Your father and I are going to get a divorce.” She’d been with this guy for I think, like, 12 or 13 years at the time, and I was bummed. I mean, the circumstances really sucked. And I was like, “Well, I don’t want his last name either.” You know, I just kind of off the cuff joked with her. I was like, “Well, I’m just going to sell my last name and, like, shove it in his face publicly that I’m getting rid of his last name.” And she laughed. And, you know, we talked about the rest of thing. Then I couldn’t stop thinking about that. I couldn’t stop thinking about this potential of, like, “What if I sold my last name? I really do now have this last name, I do not want any more. What do I do? Where do I find a last name?” It was my third last name in my life, at the time, because I had other stepfathers and had been adopted.

Andrew: With each stepfather, you’d get adopted and get a new name?

Jason: Yeah. So, you know, the name, Sadler, I’d only had for, you know, third of my life at the time or whatever. So I just had this last name I didn’t want. And it’s funny, now, many years later, I got a tweet from a guy today asking me how he could sell his last name. So I get these from people all the time. You want to talk about like leveraging an idea. I thought about being a last name pimp for a little while, but it felt really weird to, like, be selling people’s last names.

So, yeah, I couldn’t stop shaking this idea. And basically, just thought, “What if I did an auction for this eBay style. Like, that seems kind of, like, a fun thing to do.” I built a website around this and just said, “I’m just going to change my name and I’ll go full-on. Like, I’ll do this. I’ll legally change it. I’ll change it on social.” And the thing that I had at my kind of side for this was I built up a following. So this was four years into building all of this presence, having all these media, fun things. And so people had heard of me in a lot of different ways, which was really cool. So selling my last name would be, like, a whole another splash of fun for this.

Yeah. So I built the site. The auction started at zero dollars in the first 24 hours. I expected this thing to make $5,000 to $10,000, total. So, when the auction ended 5 to 10 grand, I would have been happy. That would have been crazy and fun. First 24 hours, the bidding was up to $33,000. It blew my mind. I went to bed and I was smiling at ear, not because of the money, but because of the validation of this weird idea. Like, why would someone do this? But it just was exactly what I thought it was going to be. People would get attention for it. And even people as they bid, so when you submitted a bid, it would change my last name on the site. So people would bid like 12 times in a day just to have their name up continue to be there and linked. I don’t know the details, right, like the little things.

Andrew: Yeah, I wouldn’t have thought of that. Yeah.

Jason: Yeah. And I even had a leaderboard of, like, the past 10 people. But then, we also have fan leaderboard of names that people submitted. I feel like Jason Cheez-Its was, like, the number one at the top for that because I got rid of all the porn names that people, bit of [hell 00:45:56] there for those, to get rid of those. But yeah, so the auction ended, the company,, ended up being the winning bid at $45,500 for the first thing. The marketing guy actually called me right before the timer was about to expire. He was like, “I’m $5,000 over what I was allotted to spend on your last name, you better not screw us over.” I’m legit. I’m a real person. I’m not going anywhere.

And so they won the auction. The next day I announced it on “Fox & Friends” and “USA Today.” And that was, like, the big reveal. And they ended up calculating. They got $250,000, a quarter of a million dollars in earned media in the first month from this. And for them was a huge win. They’re like,” Okay, that’s it. Like, we couldn’t get a quarter-million dollars in earned media if we paid for it. It just would not even be worth it for us.” So I lived with that name for a year Jason Headsetsdotcom.

Andrew: I thought you even went by Headsetsdotcom? Yeah, dotcom. Right. Yeah.

Jason: Yeah. Yeah. D-O-T-C-O- M. This is, like, the best thing ever. I would check into hotels, they’d go, “Name on the reservation,” and, like, after a couple of them, like, I know it’s coming. Jason Headsetsdotcom. They go, “No, not your company name. What’s your real name?” Like, “No, no, that is my real name”. And so I would have this like 5 to 10-minute loop that I would get stuck in when I would check into things. So, yeah, I lived with that name, and then sold it for a second time. So I did it two times. Made 50 grand the second time and it was just a crazy journey. It was fun.

Andrew: How did you get . . . ? Do you regret it a little bit that your book touched so many people’s lives and still on the cover, it’s Jason SurfrApp, If I remember right, I got to find a tab with that, right?

Jason: Yeah. That was the second company. No, I don’t regret it at all. I love it. I think it’s fun. I mean, people have still found me regardless, right? So, if you google Jason SurfrApp or whatever, like, you’ll find your way back to me, you know, my nice name now. That’s my forever last name as I like . . .

Andrew: And by the way, if I just search for SurfrApp, it just occurred to me, I don’t even know what it is. All I come up with is you. There is no SurfrApp anymore. Is there?

Jason: Yeah. The surfing app, Surfr, S-U-R-F-R, I believe still exists. I mean, I don’t think I’ve checked on it in a while, but I think it’s still around. It was basically like Yelp for surfing. So, like, finding great surf spots, finding food around surf spots.

Andrew: Okay. I finally found it. I have to do two words to find it. If I do it as one word, you come up only. If I do it as two words, I get an app that . . . All right, it’s not really going as strongly as Headsetsdotcom, let’s say.

Jason: Yeah. Yeah.

Andrew: All right. But I get it. How did you get on “Fox & Friends?” How did you get that publicity?

Jason: So I had a bunch of contacts where I had already done a bunch of different things. So, you know, through the IWearYourShirt years, I would get emailed by a producer out of the blue and they’d say, like, “Hey, we want to have you on this segment of CNN or of CNBC or whatever.” So I just kept all those people in a spreadsheet and just basically, kept it for a rainy day whenever I’d come up with new ideas.

So when I came up with the by my last name idea, I knew that it was a really short time window for media and, I mean, 30 days, especially back then. So I just emailed all of them. I was like, “Hey, I’m doing this crazy project. You thought shirts was weird, now I’m selling my last name.” And most of them didn’t care and they were like, “Oh. whatever.” Like, email sort of finishes and, of course, I probably forgot to email them.

But “Fox & Friends,” at the time, was like, “We want you to reveal it on our show. Like, we’ll have you kind of, like, here. We’ll go to a studio.” And I was like, “Oh, reveal it on a show? That sounds fun.” So I did that. I, like, held up, like, a little goofy sign and it was fun. Like, it was a fun way to do it. Would I go on “Fox News” now? No. But we’re seven years later, so things have changed quite a bit. But it was fun. It was fun at the time. Being on the cover of “USA Today,” like, that was super bizarre and weird, and just a funny thing to do. But yeah, I don’t regret it all. It was a lot of fun, that project.

Andrew: BuyMyFuture, I feel like I kind of lost track of you for a bit. And then suddenly, I see BuyMyFuture on like Product Hunt or something. I go, whoa. And look, I thought I was the only one who knew you and still, like, followed you. And then I saw all these people get excited about what you’re doing because they followed you too. It’s like, there wasn’t this big community of Jason fans that I knew existed, until I saw, I think it was Product Hunt or somewhere where you launched BuyMyFuture. And all these people said, “I love this guy. He keeps coming up with interesting stuff.” And I realized, “Oh, I’m not alone. There are a bunch of people.” What was the reason for that?

Jason: Yeah. So, in 2013, when I was in the Chick-fil-A era, the state of despair, I had to find some other way to make money. So I had to sponsor my book project later in the year. So I didn’t have any money basically from, like, April until the end of the year and so I had to find some way to make money. And I did some public speaking. But the other thing I stumbled into was creating online courses. And so, again, I was so burnt out from all this stuff. I just wanted something easy. I wanted something that, like, I saw people making money and I could just try it.

And so I actually just cobbled together my own online course. And for the first, you know, a couple of months, didn’t make very much money from it, but I ended up making enough to kind of sustain. And then I got interested in online courses. And I built one with my buddy Paul Jarvis, about writing a book. And then we build one about personal branding. And then I help my wife build one. So one thing led to another ended up with, like, six online courses and then two software products. And I had to market and promote all of these, and I don’t have employees. I, like, don’t want employees from my IWearYourShirt history.

Andrew: Just to be clear, the thing that you told me we learned from this before we got started was you said,” Look, I wish I would have just kept it small instead of trying to become a Silicon Valley success story with all these people.” Am I right?

Jason: Exactly.

Andrew: Yeah. Okay. And so you said, “Look, I’ve got all this software, I’ve got all these courses. I’m not going to repeat my mistake. I got to keep it simple.” And then, continue. Sorry.

Jason: Yeah. Exactly. So I don’t want to hire people. I don’t want people to manage this. And I have to manage them and all that stuff. What can I do to, like, make it simple? And I remember I was just having coffee one morning and the idea hit me. What if I package it all together? Okay. That’s not too interesting, like, people bundle things before. But what if I also included anything I would make in the future with that bundle. So you not only buy and get the stuff, for the rest of my life, you get anything I make at one set price.

And I was like, “Oh, this is really . . . ” You know, it’s like maximum customer lifetime value for me, probably. I’m, like, one customer paying me $1,000 and then maximum, what I called Jason value, which sounds douchey, but I promise you, I didn’t think of it that way. It’s like, “You’re going to get the most value out of me as possible.” And it just seemed interesting.

So I kind of came up with some different ideas of names of things. And BuyMyFuture was the one that just kind of stuck and put the website together, put a whole . . . like, had a copywriter help me write everything. And then yeah, put it on Product Hunt. You know, I had an email list of my own. And it launched. And 178 people bought my future for the two weeks that it was opened in 2015 for the first time. And made $178,000 selling my future. And a lot of those people are still now in our Wandering Aimfully community. Like, they’re kind of grandfathered into our newest stuff. And they’re still getting value from things. They’re still getting all the new stuff. We create new software, new courses, new workshops, all . . .

Andrew: I think that would be so scary to people. I don’t know what I’m going to create in the future. What if I do this? What if I do that? How do I get it? But I like the guts behind it, too.

Jason: Yeah. You tend to find that . . . And I think this boils down to, like, I’m just genuinely a good person. And as we talked about, like, I just care about people. So I think what people realize is when they go to buy, they’re not like, “Oh, this guy is, like, a cutthroat business guy.” And like, “Yeah, but it’s like, no, he’s just a dude who likes creating fun things. Like, I want to support him, A. I want his stuff, B.” And sure, if I don’t get a whole bunch of things for years, I’m going to be okay. And we’ve . . .

Andrew: No, I mean risky for you. I think a lot of people would have come up with it, would have said, “What if I sell gold necklaces, then I have to give them a gold necklace?”

Jason: Yeah. And, you know, there were some terms in there too. Like, if I have a project with another person, you can’t automatically have that because there’s someone else involved. So I thought through some of those things, but yeah, we’ve continued to give value to those people for years. And what you realize too, is if you were to think . . . This is kind of what my hesitation was that all these people are going to buy and then I’m not going to have any more customers for things.

But what you realize is that there’s a big pool of people out there. And even the 178 people that bought this, it’s 178 people. If we’re being honest, that is not very many people, so you’re going to find more people, more people are going to find you. And that’s what we’ve continued to find over the years. You know, and even though we have now 500 people that have fallen into that BuyMyFuture, and then my wife and I combined to BuyOurFuture, you know, 500 people, we’re giving them all of this stuff, but it’s all stuff that digital products that, you know, we’re not doing physical goods. We’re probably never going to do those things. You know, with books, we can get PDFs and stuff like that. So it tends to work itself out.

Andrew: What if you do do physical products? What if you decided, you know what? I’m actually going to create a t-shirt?

Jason: Yeah. If we did that, we would just have to factor that in. I mean, that’s a promise that we made to people. So we go, “Okay. We have 500 times X amount of, you know, whatever our cost is, that has to be factored into however we start this business.” And if we can afford that, cool, then we’ll do that. But otherwise, maybe we have to wait until that makes sense financially for us to do that.

Andrew: You called up the first few people who joined, who bought BuyMyFuture. Why did you call them and what did you get out of that?

Jason: So, yeah, I did 49 phone calls. This is kind of, like, customer discovery calls. I’d never had actual conversations with customers, which is just bizarre to think about.

Andrew: Even all those people about your t-shirts and name, you didn’t talk to them before they bought anything?

Jason: Never had a phone call. I mean, maybe one sales call, but I never had a call with them afterwards. So the calls that I had were people who had bought courses from me, and I wanted to just talk to them about the idea, but then hear how they talked about it.

Andrew: Ah, it was not people after they bought? It was before they bought.

Jason: Before they bought.

Andrew: They bought your course, and you said, “Let me tell you about this thing I’m going to sell.” Got it. Okay.

Jason: And what I heard was, the way that I thought about BuyMyFuture was not how they saw it.

Andrew: Tell me, what was the difference?

Jason: So I thought about it is like, “You’re going to get this bundle of stuff and you’re going to get value forever.” What they thought about was,” Oh, I’m going to get immediate access to you and to your mind, and to your things.” Because, of course, I’m going to email them back. Like, these are people who are buying my future. I didn’t even think about that. That’s just, like, a natural thing that, like . . .

Andrew: I guess, I still don’t even understand what they mean.

Jason: Just having, like, a direct access to me. Like, I think a lot of people when they buy a course, or anything, or a book, they don’t feel like they have access to the person who created it. And maybe they don’t. Like there’s, you know, gatekeepers, and assistants, and all of that. For me, it’s like you get direct access to me. So you get to email me, we can talk, we can hop on a call.

Andrew: And you just took it for granted that that was coming along with it because they’re coming along for the rest of your life? You realize they valued that more than all the other stuff. And is that why you came out with the Slack community?

Jason: So that was the other thing. So that first thing was, like, direct access to me. The second was, they were like, “Oh, are we going to be able to know who else bought so that, like, we can be in this, like, little community together?” You know, I was like, “Why would anyone care?”

Andrew: Me too. I would think that.

Jason: Like, you’re on Twitter with other people and they didn’t want that. They wanted, like, a private community. And that community has continued to thrive for years. And it is such an amazing community and people still love it. So those two things were really great. And just the verbiage that they used as well, I used that in the sales copy on the site because it was how they talked about it. And I don’t remember the specific phrases, but it was just little things that the way that I said it didn’t resonate. But then the way that they said it back, multiple people said it that way. And I was like, “Okay. This needs to go, like, in the headline or buy a button or whatever.” I’m sure I have it written down somewhere. But those were the really important kind of things I heard from those calls.

Andrew: All right, and now you’re working on Wandering Aimfully, and the website is What is this?

Jason: So this has been an interesting evolution. So my wife and I had separate businesses in 2018. I had, very appropriately named because I do a bunch of stuff. My wife had Made Vibrant, which was a community for soulful, creative people. And we had a lot of overlap. You know, people liked both of us. They liked what we were doing, but we weren’t doing a lot of work together. You know, we were next to each other but not overlapping in work. And we decided, what if we combined together both of our things because she has the very, like, emotional, soulful, thoughtful, mindful, creative brain. And I have the creative action taking practical, weird, you know, kind of brain. And those two together, are very interesting business marriage, if you will. And so we just thought, “What if we brought that stuff together.”

And so our first trial run was with BuyOurFuture project. So graduating from by my to buy our, and people really liked it. They liked they could get both of us. And so then we just thought, “Okay. The BuyOurFuture thing is kind of interesting.” It kind of wore itself thin for us. Like, we just kind of got bored with it.

So, if we created this ethos, this Wandering Aimfully ethos that Caroline came up with, we are so exploratory in what we do. We’re so interested in trying new things. But it’s with aim. Like it’s not aimless, which is what you think about when you hear that phrase. That’s the phrase. It’s aimful. Like, we have ideas. Like, we know what we’re doing. We’re smart. We’re savvy at some of these things. So we want to wander, but we also really want to be aimful about it.

And we thought, “Okay, well, let’s help people do what we’ve done.” We’ve gone from both working with clients to making digital products, and making a great living doing it. Let’s bring those people together in one place and have a membership where people can feel like they get a bunch of resources from us, they get access to this community, and they can feel like they’re a part of something bigger. So “Buy Our Future” doesn’t feel like you’re a part of like a bigger ethos. But Wandering Aimfully does because you can latch on to it and you can feel like you’re a part of it.

Andrew: And that does kind of connect now. This is what you’ve realized about yourself. You’re a creative person, you’re not trying to be an entrepreneur, like, extraordinaire. You just want to own the fact that you’ve got this, like, what would have been considered weird or maybe is considered weird thing about you. And that’s what makes you amazing, not the fact that you use that to become the head of a company with 70 people wearing t-shirts and pimping. You’re not going to be the next Gary Vaynerchuk. That’s not you.

Jason: Not at all. Yeah. And, you know, I went down that road a little bit. And I’ve had the taste of the hustle mindset and, you know, the growing the company, the getting more employees, those things, and it just didn’t feel good. And it just doesn’t feel like me. And I love Gary. Gary is a great guy. He’s a super talented guy, but it’s not for me, you know.

And for me, you know, the thing that I think also separates our style of entrepreneurship from a lot of people is a lot of people just see unending growth. You know, like, we could have potential growth forever. For us, we want to cap it at enough. So we’re happy to make a certain amount of money per month and not make more money from that. Could we make more money? Could we make more things? Could we sell more stuff? Absolutely. We don’t care. We’re not interested in that. Because for us, we don’t want to think about the money mindset and, like, the hedonic treadmill of growth.

As much as money is great and it affords you do amazing things, we also know that it can drag you down, and it can keep you from being creative, and fulfilled, and thoughtful. And I know that sounds weird to a lot of people, but it’s also the thing that we just love. Like, we love being able to say, “This is how much money we want to make a month. It’s enough for us.” We’ve defined it for us, not based on anything else and we’re happy to just hit that number and then move forward.

Andrew: What’s the number?

Jason: Thirty-three thousand a month?

Andrew: You do 33? Why is that the number?

Jason: We had just broke it down. We looked at, like, what are our average expenses for six months for business and personal? You know, based on that, what are we going to need to pay, you know, have aside in taxes? How much do we want to give for charitable giving? And, like, what’s a good percentage of that, you know, money per month? And then how much profit do we want to have? You know, and then probably some buffer and, like, other things. We wrote it all down.

Andrew: Thirty-three thousand plus, you want to have a little profit to store away for later.

Jason: Yeah. So out of the 33,000, I think, 10 grand of it should be profit. It’s basically what we’re shooting for, so we’re not there yet. The complete honest truth is that we’re on a journey to get to enough. It’s kind of what we’re walking on.

Andrew: So we are talking about $400,000 a year is what you’re aiming for with this business?

Jason: Yes.

Andrew: Got it. Oh, so you’re saying, “Look, if we do $400,000 a year, our expenses are pretty insignificant for work,” right, but the expenses will come out of that. Got it. How close are you to that? You’re what, 10?

Jason: So we’re at 10, just with Wandering Aimfully, but we kind of look at it, not necessarily that just Wandering Aimfully has to do it. So I have a software product called Teachery, which also is about 10 grand in recurring revenue. We have that plus some random things. You know, like, when you write a book, you get a book deal. So there is a bunch of stuff that works out.

So we’re about two-thirds of the way there and some months are better than others. You know, we have the ups and downs like everybody else. But it’s fun to have, like, a level to get to. You know, like that boss, that Donkey Kong at the top of the Mario ladder in the original . . . like, that’s kind of how we think about this. And in each level up, we try and have fun with it as much as possible, as opposed to just thinking, “Okay. We can make money forever and make all this look . . . It’s like, “No. We have a cap that we want to get to,” and reaching that is kind of a fun journey.

Andrew: All right, the book, for anyone who’s into this type of mindset, and I was going to say into Jason Zook’s mindset, then I realized I should explain. Zook is your grandfather’s last name when you decided to stop selling your last name. You said, “What am I going to take?” And you took your mom’s dad’s last name. Am I right?

Jason: Yes.

Andrew: Paternal grandfather’s last name. All right, so Jason’s Zook’s book is called “Own Your Weird: An Oddly Effective Way for Finding Happiness in Work, Life, and Love.” And it seems like everything that I’ve been reading or every link that I clicked on from your past, seems to just bring me back to a URL that on Am I right? Like now leads to a blog post about that experience, on So everything else . . . You’re nodding so I’m going to say, anything you want to find out about Jason is available at Did I miss anything?

Jason: No, it’s good discussion my friend. Fun show.

Andrew: I like it. There’s so much, like, that I wanted to follow up on and I got to do it. I want to thank the two sponsors who made this interview happen. The first, if you’re now looking to hire developers, look at this, if you took this thing that, like, auctioning pages in a book instead of saying, “I’m just going to pick a quick thing and use that.” You could have, Jason. You really could have. You could have just said, “There’s so many off-the-shelf apps that you could use.” But he said “No, I need it to be my way, I needed it have my special feel.” And you didn’t get carried away with it where you were just over investing in it. But it looked great. It looked Jason’s way.

Anyone out there who needs hire developer to build their business just right, you should go to Top as in top of your head, tal, as in

I want to thank the second sponsor who made this interview happen. If you’re looking to host a website or just get creative and explore what you want to create, go to

And finally, one of the things that I liked about you, Jason, in our very first interview, once we were done, I said I liked the idea. And then we were still recording, but I think we were done with the interview and you said “You should buy a day, you should buy a t-shirt.” And I didn’t have a t-shirt at the time, but I loved that you were even willing to sell me in on the interview. Like, the interview is done, Andrew. Great. You said about buying a t-shirt. I loved it. I loved it. I’m going to do the same thing and end here by saying guys, “If you want to learn from the best of the best entrepreneurs, go to

I bring back entrepreneurs who I’ve had on here to teach courses about the stuff that they do, especially well. One of my latest favorites that came on is Chris Ronzio. He is a guy who had a company that was taking videos of cheerleaders and other things. And one of the things that happened, as the company got bigger was, he didn’t show up to an event, his team just didn’t show up and he said, “This is not a problem of the team. It’s a problem of systems.”

And he geeked out on systems, he systemized his company. He got so good at systemizing that he became a consultant, systemizing other people’s businesses. I guess the word is systematizing but I hate systematizing, systemizing. And then he created software to help people manage their systems. The software is called Trainual. I said, “Listen, I love this interview so much. I’m like bouncing off my seat. Can you please talk to our course producer and create a course, showing us, showing me, showing other people how they could systemize their company?” He said, “Yeah, let’s do it.” And so he is in there.

So many other entrepreneurs who you recognize from my interviews are there. If you want to see the full list, go to And if you sign up, you’ll be a member of Mixergy. And I appreciate you doing that because that’s what supports all the research and work that goes into Mixergy. Jason Zook, thanks so much for doing this. Zook Excuse me, Zook. I keep saying Zook. Zook.

Jason: It’s okay, it goes both ways. In Canada, everyone says Zook, so, you know . . .

Andrew: Zook. Yeah. They say boot.

Jason: They do.

Andrew: They do say it. But what the hell do they know? All right, let me know when you’re ready to do push-ups baby.

Jason: All right, sounds good.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.