How to be a Fearless Entrepreneur with Jason Zook

Jason Zook, formerly known as Jason Sadler, Jason HeadsetsDotCom and Jason SurfrApp is the founder of IWearYourShirt. He’s an action taker, unconventional marketer, and fearless entrepreneur.

In 2008, he saw the growing influence of social media and decided he could utilize those platforms in a new and unique way by getting paid to wear sponsored t-shirts for a living. Each day, he represented a different company online using social media sites like Facebook, Twitter, YouTube, Ustream, and Flickr. That’s right, Jason was paid to wear t-shirts for a living. Pretty sweet gig if you ask me.

He’s worked with over 1,500 clients that have included professional sports organizations, advertising agencies, Fortune 500’s, startups, and more. He also previously co-owned a web design company, and in 2013 and 2014, he auctioned off his last name to the

In 2014, he wrote his first book, Creativity For Sale, which he self-published by crowd-sourcing over $75,000 worth of sponsorships on the bottom of each page of the book.

Aside from his sponsored antics and insatiable need to scratch his entrepreneurial itch, he’s incredibly passionate about his family, public speaking, helping other entrepreneurs, sports, technology, cars, and his dog, Plaxico.

So now that you know a little bit about Jason let’s get straight into it!

What inspired you to start IWearYourShirt?

Back in the days of pre-Snapchat and pre-Instagram social media, I was a co-founder of a small web design company. I wasn’t using social media (this was 2008) but our clients kept asking me about it. Naturally I looked into Twitter, Facebook, and YouTube and saw the communities that were growing there. There were so many people already discussing their favorite companies, brands, etc, but there wasn’t a way to connect the companies with these people on these various platforms. IWearYourShirt was my plan to create the first social media advertising company and be the face behind it. The t-shirt part of it emerged when I was standing in my closet one morning and making the difficult decision of which shirt to wear each day.

Why did your typical 9–5 job simply not cut it for you?

I don’t like real ladders, let alone corporate ladders. The idea of climbing the ranks at a company, getting fancy new titles, and business cards never sat well with me. Plus, I have control issues and don’t like being told what to do. All of those feelings made a 9–5 job impossible for me. Recently I reflected on a pivotal moment for myself in 2006. I wrote about that here if you’d like to know more.

What does an average day in the life of Jason Zook look like?

Probably pretty boring for a lot of people. A few years ago when IWearYourShirt was active it may have been more exciting (filming a daily video, hosting an hour-long live video show, etc). Nowadays a typical day looks like the following: Wake up without an alarm. Check Instagram on my phone (nothing else). Roll out of bed and put on a pot of coffee. While the coffee brews, I read a handful of Calvin and Hobbes comics. When the coffee is done I open my laptop, the Letterspace app and write between 500–1,000 words before checking any social media sites or my email inbox. The majority of that daily writing gets thrown in the trash. After that I’ll check email, work on my various projects, take a few phone calls, and take multiple breaks throughout the day to play with my dog Plaxico or distract my girlfriend Caroline from her work.

You always seem to come up with the most amazing and frankly zany ideas. Where do they come from?

Space. Not like outer space, but space in my days/weeks/etc. I can pinpoint actual moments in time when I’ve come up with my various ideas. Almost every single one has come during a time of stillness, devoid of notifications and the Internet. IWearYourShirt happened late one night while lying in bed, unable to fall asleep (pre-iPhone next to the bed). BuyMyLastName came on a Skype call with my Mom where I was doing nothing else. SponsorMyBook happened over lunch at a Tex-Mex place with a friend. The Bundle of Awesome happened in an actual cabin in the woods while I was taking a social media detox. Teachery happened while driving down a quiet beach road with my girlfriend with no music on. Product to Profit popped in my brain while walking my dog one afternoon. The one thing all of these have in common is that I was away from my computer and devices. I gave my brain the space to think, compute, and create. I also try to limit the control social media and the Internet has on me. It’s highly addictive and insanely counterproductive.

You have frequently mentioned your love for Calvin & Hobbes. What is your all time favorite strip?

I can’t pick one strip. I just can’t. I mean, if you forced me to, I’d pick the final strip where Calvin and Hobbes are on the snow sled and Calvin is saying “let’s go exploring.” We all need to do more exploring in life, especially in nature without technology. Listen, I love technology, we just need a damn break from it here and there! Sorry, got a soapbox there. My favorite C&H book would be “The Essential Calvin and Hobbes.” The title does not lie.

What advice would you give someone who’s feeling stuck in their job or simply in life?

Change things. Change your rituals (especially in the morning). Do more things for yourself, especially things that make you happy but that aren’t destructive. Find and create more space in your life. Challenge yourself to do things you wouldn’t normally do. Read a book way outside your normal reading categories. Close your laptop. Turn off your phone. Go for a walk. Quit more things: Quit your crappy friends who hold you back. Quit watching TV. Quit being lazy. Quit complaining. Quit spending money on useless stuff you don’t need. Quit a project that you don’t think you can quit because you’ve already invested too much time/money. Invest in yourself.

What books would you highly recommend anyone reading?

I’ll give you my top three right now:

I also have a reading list I constantly update here.

What are the biggest challenges you have found to come with the life of an entrepreneur?

Hmmmmm… This is a tough one. One of the hardest things is balance. How do you stop working on things you love working on to make sure you keep your relationships with family, friends, loved ones healthy? How do you know when it’s time to give up on a project? How do you swallow your pride and admit you were wrong? How do you avoid going into debt to chase a dream you truly believe in? I know it’s a weird answer to ask a lot of questions, but those are things I think are the toughest when it comes to being an entrepreneur. I wrote an open letter to entrepreneurs that’s gotten passed around the web quite a bit.

You are now doing a podcast with your uber talented girlfriend, Caroline. How has that experience been?

It’s been really great! The podcast, called “Sleeping With The Boss,” has no business angle (at the moment). We simply wanted to work on a project together and see where the experience led us. Caroline used to work for me when IWearYourShirt was active, but when it closed up shop in 2013 we simply worked together in the same room (not on the same businesses). This podcast was a way for us to reconnect and share our experiences of living together, working together, and loving together. We think there are a lot of “entrepreneurial couples” out there who can really relate to our lifestyle and circumstances.

So what’s next for you? What projects are you working on as of late?

I have a ton of stuff I’m working on right now. Probably too much. The thing I’m most passionate about is my email list. I know that sounds odd, but I’ve done email marketing wrong over the years and now I’m really investing heavily in it. My email list, The Action Army, gets all my best content first. They get access to all my projects first. They’re a group of creative entrepreneurs who are building, making, creating, struggling, and hopefully learning from me. I have an online learning platform called Teachery that I co-founded. There are tons of online course/teaching platforms out there, but we’re carving out our own niche. We know everyone has a skill to teach and we think the majority of online course platforms suck (with exception to Fedora — and yes, I just complimented our competition). I’m also, finally, creating a product based on the incremental pricing structure I created with IWearYourShirt called Bumpsale. I’ve used it on a few projects this year (Bundle of Awesome and Product to Profit) and can’t wait to let anyone in the world sell their stuff in a super unique way. I also have two podcasts, do some public speaking, consulting, and I spend a ton of time answering emails. Oh, and I have about 4 more projects I want to work on this year, as well as a second book.

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