023: Jason Zook T-Shirt Designer, YouTuber and Author Who Sold His Name Twice

Self-published, to a sponsor-driven book, to a traditional book deal!

Inspired by Seth Godin’s book, Purple Cow, Jason Zook is known for a variety of things, one of which is making over a million dollars wearing T-shirts. He also sold his name twice and auctioned them off – one of them was Jason SurfrApp. Jason is also the author of Creativity for Sale which he wrote in only two weeks.

[01:50] Writing Jason’s First Book

Jason admits to not being an avid reader up until 2013. In fact, he reckons only reading a total of five books in fifteen years since high school. He suspects it was the explosion of the internet at that time where you no longer have to read books since you get to read articles or blog posts.

Meanwhile, Jason had to shut down his T-shirt business in 2013 and trying to figure out what he was going to do next, he just found himself really lost. So he decided writing some of the stuff and just blogging about it.

With only $9 in his bank account at that time, he was over $100,000 in debt. Then his friend, who was working for a book coaching and authoring company at that time, encouraged him to write a book. But not a book reader himself, he really didn’t think he was able to do it. Sure, he was already into blogging at that time so his friend gave him the idea to continue doing it, just in a longer format.

Indeed, he considered it, but his only concern was how to end it. For him, the ending doesn’t exist. He still hasn’t figured it all out. He just didn’t have any idea that he could actually end the book in any way he wants it to end. This got him fired up to finally write a book.

Moreover, he had this brilliant idea of having sponsors at the bottom of the pages. It was an opportunity for him to get some money while being able to create an interesting story behind the book. At the same time, it gave him that creative outlet to express all the things he wanted to.

[05:50] Be the Purple Cow

After graduating college in 2005, Jason was working at an office as a designer and everything in the office was beige. He couldn’t really complain about anything, but every single he felt completely unfulfilled. Then a coworker emailed them about The Million Dollar Homepage where it gave him the idea that you can basically sell anything.

Then, Seth Godin’s book, Purple Cow, landed on his desk. The book talks about how you look around and everyone’s a black and white cow. but you can be the purple cow. You can be the one that stands out!

Jason points out that there is a purple cow in all of us. And this is what he realized as he moved into this phase of his life. This led him to leave the 9-5 job and start his own design company along with his friend.

You Have to Do the Work, Too

By 2008, their clients were asking them about social media. And so he had this idea of connecting businesses to the people on social media – in a human way. When they built and launched the website, 12 people showed up in the first 48 hours. He describes this as a little disheartening, but at the same time, it gave him that realization that you can’t just put something on the internet and expect everyone to show up. You have to actually do the work and promote it.

This led to five years of intense work which involved filming a YouTube video each day for 889 days straight. At the same time, he was hosting an hour-long live video show. And still managing the clients and doing all the sales, marketing, and accounting. With only two people when they started, they grew the company to five people in the third year. Jason also had this notion to grow and scale and do all these startup things since that was all he was reading about. And all this has left him still unfulfilled and frustrated.

But had he not experience all of those things, he wouldn’t have had a single page to write. So it was all worth it!

[13:15] How He Sold His Last Name Twice

Jason would describe being like a goofball and living a weird life selling those shirts each day. In fact, he was sponsored to cruise in the Caribbean and he was asked by Reuters to write a journal so he could publish his world adventures. At that point, he knew you can literally do anything since someone will be interested in it because there’s always a story to tell.

A Brilliant Idea!

Meanwhile, he was talking with his mom over Skype about her divorce and distraught, he decided to also sell his last name and find a different one. And this planted a seed in his mind about selling his last name. At that time, he had three different last names and there was no attachment to his last name on his part. And wanting to help the business side of things, he did a quick research about people selling their last names. And there was none. But having built that confidence from having been paid to wear T-shirts for a living and getting sponsored cruises, he knew he could be the guy who could sell his last name.

And so he did. He had a developer put together an online auction site designed just for him. When the site went live, he was expecting to make $5,000 in a 30-day auction. Lo and behold, by the end of the first day, the bidding has gone from $0 to $33,000.

Success Doesn’t Happen Overnight

But this wasn’t just an overnight thing. He wouldn’t have done this when he hadn’t put all the work in and no one had ever heard of him. This was all thanks to his four years of shirt business where he had already built that community. The first auction ended at $45,500. Then he did this again the second time because he was writing the book Creativity for Sale.

[18:50] Overcoming the Impostor Syndrome and Building Your Writing Muscle

Jason admits there were times he’d ask himself whether he’s been pushing himself too far. But he believes that those are the moments he knows he’s doing the right thing. Those are the ideas that light him up. Those are the things he values a lot as a person. And he gets personal satisfaction from seeing an idea grow. It’s like creating a painting in his head and then turning that painting around for everyone to see. He doesn’t care if someone buys it or even if a lot of people see it or not. He just wants to get his art out of his brain and into a physical or digital form in a way that someone else could see it exists.

When he wrote Creativity for Sale, he was having all these impostor syndrome thoughts in his head. But he went on to just write anyway. He realized that the way he writes is the only way he’s going to write the book anyway so just do what you have to do and just let your natural voice come out of that. Hopefully, people will enjoy that. If not, that’s okay.

Just Write

Now, he has written about 4 millions words total and he has thrown 90% of those away. That’s because he has given himself permission to accept that his words may not be the most pristine but he was going to write more. He just needed to get them out and build that muscle. Then eventually, you get to find your voice and your writing style that people can resonate with.

Moreover, Jason recommends not to even stress about what you write. People don’t always want to read the perfect prose. So just do it in your own unique way and that is your own purpleness coming out of you. Then you stand out and come out unique for everyone to enjoy.

You can write all these things. Keep them in folders and even delete them. And if something keeps coming out of you and you think you need to publish it, then it was probably a very strong idea that you could write it a hundred times. It doesn’t matter if you throw it away because it’s going to keep coming back.

So what got Jason to just get through writing his first draft was to just write it and then just cut everything out. And if there was something he really loved, then he could just write it again and put it back in.

[24:40] Jason’s Two-Week Writing and Editing Process

With an insatiable ability to get things done, Jason decided to just write his book in two weeks. He’d basically write as much as he could throughout as many hours in the day. The only thing that was different every day was trying to force himself to sit somewhere different in his house. He found that sitting and writing on his desk for two days made him really uninspired and motivated. And just changing this with as simple as sitting down on the couch or in other places in his house, he found that he was the most proficient at writing when he was standing in his kitchen bar and typing. Hence, although it was challenging, this made things much easier for him because he didn’t have to force himself to sit and be in an uncomfortable place, He didn’t have a strict amount of hours to write every day. Instead, he only told himself that it has to be done by the end of two weeks.

In editing the draft made of 65,000 words in those two weeks, he had his wife help him reorganize it and he had his book coach. For him, he considers her as a therapist as they explored a lot of topics since he still was hanging on to a lot of baggage that he didn’t want to share.

Consequently, Jason says that writing his first book, almost every part of it, was one of the most cathartic things he had done for his life and his business. It’s about being able to get all the stuff out and get out of his chest. His editor was just asking him questions and then she did a big structural edit of it.

[27:50] Your First Draft Is Always Awful

Jason points out that you need to accept that everyone’s first draft is awful. I recommend you read the book Bird by Bird by Anne Lamott which talks about that shitty first draft. You don’t magically leap from playing high school football to being in the Olympics. That said, everyone’s draft is awful no matter how good of a writer you are. And the people that cared too much about perfection? They never get to write a thing.

Jason adds that this is because you get paralyzed by that notion of perfection. But none of those things really matter to the people reading it. And besides, it doesn’t mean you’re going to have to publish your first draft.

Furthermore, Jason sees the importance of just telling stories and let the readers decide if they’re good or not. So he realized by the time he was writing his succeeding drafts that all he has done is writing stories from his life and was wondering if anybody really cared. His editor then shared this little secret to him – that it’s the only thing people care about. It’s not just all the lessons learned or the tips and the things you can avoid. It’s the stories behind them that people can relate to and see themselves in the stories. Or it’s about letting them have a mental picture of what’s going on that would resonate and stick with them.

So they did the first draft in two weeks and did the structural edit in a month. In about two months, the book was fully formatted and ready to be published on Amazon.

[31:40] A Drive to Write More Than One Book

When he decided to write Creativity for Sale, his thought process behind this was looking a bit ahead of things. He was looking for an opportunity to do something that he hasn’t seen done – being an entrepreneur that does weird things, accrue a bunch of stories over the next couple of years, and be able to share his experiences and lessons with people seeking to take on an entrepreneurial journey.

So he thought that Creativity for Sale was just the first of many books since he’s definitely going to have a bunch more stories, more experiences, more lessons.

[33:05] Watch Me Write!

Trying not to be long-winded on his second book, he also wanted to take up a notch and do something he hasn’t done before. And this was to write his draft publicly for everyone to see. So people could literally see Jason typing every single world. He then designed a little markdown editor that has no tools. You just write so you can’t get distracted by any formatting font. He had this developer take this design and build it as a web application. Before he finished writing, he already reached out to a couple of sponsors, Podia and Acuity Scheduling. This way, he’d have money to hire an editor since he was going to need one.

For this, he was setting writing hours so people could follow. He wrote from 9 am to 1:30 pm every day. On his end, all he could see was the writing editor. But on the front end of the website, there’s a little chat box. And anybody watching from anywhere in the world could see Jason type every single world.

Giving Him a Reason to Show Up

Moreover, this also got him to show up every day. He had no excuse since people were waiting. And this made it easier for him to open up the writing editor since he knew he had all these people watching. He had to write for them and he had to show up for them. He did this for two weeks and it was a fun experience!

[36:38] Again, Your First Draft Is Always Shitty

Funny thing, Jason knew it was going to be a shitty first draft and it did surprise a lot of people. He stresses that your first draft has to be bad otherwise it’s not going to keep going. It needs somewhere to start.

It’s our current educational system where people are trained to be editors but they’re just tricked as being writers. That’s why no one thinks a writer wants to write. We’re told do as little work as we can to get the grade we can. So we don’t write, we edit. We become fixers of words just to make it pass the test.

[37:43] Some Truths About Writing

First, realize that books don’t have to take forever to write. Secondly, your draft, no matter how much effort you take, won’t be good unless you want it to be a textbook. But people don’t read textbooks.

Also, when writing a fictional book creativity is key. Writing is a team sport, too. In fact, Jason suggests having this public experiment of presenting the characters and the plotline of the story. He’s going to write a version of the book and I’m going to do the same. Then see what happens next. Wouldn’t this be cool?

Another thing to keep in mind is that everything is original just as everything is borrowed so you have to be okay with that.

[43:15] Don’t Let Anyone Tell You That You Can’t Do It

It’s sad how kids are being taught that they’re not creative enough to write. Don’t ever think about that kind of limitation. Or that you don’t have the tools. Don’t get told you’re not creative enough. Instead, just do something and keep moving forward.

Writing doesn’t have to be done the way you’re taught. You can do it in silly ways. It’s your message and your uniqueness that people show up for.

It’s actually funny how it’s all about you but it’s also less about you at the same time. Jason agrees on this in that with all those projects he launched, he thought of himself as being kind of self-centered as everything was about him. But then at the same time, with the WatchMeWrite project, for instance, he saw people in the chat that began to form friendships.

[48:35] The Action Army Podcast And Wandering Aimfully

Although Jason likes writing, he also misses how you’re able to express yourself through a video or audio. But having been burnt out on filming over 1,500 videos for his shirt business, he sought the power of audio through The Action Army Podcast. It ran for 100 episodes. The podcast was something he considered as a form of therapy.
Currently, Jason is working on a new show with his wife, Caroline, which is called Wandering Aimfully.
Ultimately, Jason’s wish is for people to realize that you can take control of your life and you can do something you want to do no matter how big or small that is and no matter what version of success that brings to you. In fact, none of that matters, but it’s just doing something and feeling empowered for having an idea which you actually made it happen. You did it and so you could do more!

Episode Resources:

Wandering Aimfully


Creativity for Sale by Jason Zook

The Action Army Podcast

Purple Cow by Seth Godin

Bird by Bird by Anne Lamott


Acuity Scheduling

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023: Jason Zook T-Shirt Designer, YouTuber and Author Who Sold His Name Twice023: Jason Zook T-Shirt Designer, YouTuber and Author Who Sold His Name Twice

023: Jason Zook T-Shirt Designer, YouTuber and Author Who Sold His Name Twice