Episode #16: Jason Zook

Our guest today is one of the most creative entrepreneurs in the world. We present to you Jason Zook, a guy who made a radical shift ultimately deciding to leave his “beige world" once and for all and embark on one of the most colorful entrepreneurial journeys of our time. 

Jason started out by getting companies to pay him to wear their T-shirts for a living. He then sold his last name, twice, and then wrote the world’s first ever fully-sponsored book. Now he is in the middle of what might be his craziest stunt yet. He’s quite literally selling his future, and he’s doing it so he can help creative professionals take action and make money doing what they love. 

This is the fourth episode of the second season of the Hacking UI podcast, 'Scaling a Side Project'. In this season we interview designers, developers, and creative entrepreneurs who built and scaled successful side projects  that we admire.

The Side Project Accelerator We are launching the second batch of the 

Side Project Accelerator in early October. Spots are limited, and we expect it to sell out fast. You can sign up for the waiting list on the program's page and you'll get notified as soon as registration opens so you don't miss it. 

Key points from this episode:

• Learn how Jason made money as a first-time author, with his book fully sponsored by 204 companies.
• Understand why it is important to Jason not to copy someone else’s success, but to put his own unique twist on things instead.
• What does it mean to “steal with pride”, and how does Jason use this in his creative process?
• Find out how Jason grew I Wear Your Shirt into a successful company by using the strategy of selling first to prove that someone wants to pay for it.
• Learn why it’s not the first email that matters in growing your business; it’s the follow-up email.
• How did Jason use his dog to raise money for charity?
• Find out how Jason got $30,000 in the first 24 hours selling his last name the first time, and $50,000 the second time he sold it.
• Understand how Jason leverages the talents and skills of freelancers to build and grow his business ventures, pulling on their unique strengths to create a successful team.
• “The idea is only as good as your ability to get it out into the world and have people pay for it and use it.”
• Learn how Jason went from having $9 in his bank account to writing a fully sponsored book and making a profit of $75,000 before even writing a single word of it.
• Find out why Jason strongly believes everyone has the amount of time they need, but that they’re just not willing to sacrifice to work with the time that they have.
• Understand how finding balance means that life is more than the things that you create and that you just have to figure out what works the best for you.
• Most people have a scarcity mindset; find out why it is important to understand that there is always more to be had, especially as a creative entrepreneur.
• Learn why you should not make a product/service perfect the first time and instead get it out into the world so that the improvement can begin.
• Understand how the exact strategies that can help someone else to their success, may not get you there; personal adaptation and application is key.
• Find out why one of the biggest mistakes entrepreneurs make is selling their time alongside their products.
• Learn how growing an audience that believes in your idea is better than “buying” an audience with free giveaways and bonus material; bonus material should instead by used to surprise your loyal audience.

Links from the show

• Jason’s website
• Jason’s Twitter (@iwearyourshirt)
• Buy My Future, Jason’s current project
• Jason’s first business
• Buy My Future breakdown article
• Million Dollar Homepage
• Steal like an artist, book Jason mentioned in the show by Austin Kleon

Transcript The transcript of this episode, will be ready soon. Check back tomorrow 

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About The Hacking UI Podcast The Hacking UI podcast is hosted by Sagi Shrieber and David Tintner, a designer and developer who are also both entrepreneurs, bloggers, productivity/time-hacking maniacs, and all around tech geeks. 

We started this podcast off with the 'Scaling a Design Team series' where we spoke with design leaders from top notch companies like Facebook, Apple, InVision, and Intercom, to discuss team structures, responsibilities, and workflows.

A few months ago we quit our day jobs to work on our former side project, Hacking UI, full time. So we found it fitting that our second season of the podcast should touch on that subject. The second season is called 'Scaling a Side Project', and we'll interview creative entrepreneurs that we admire in order to get them to share their tips, experiences and secrets to success.