I got paid $1,200,000 to wear t-shirts, I sold my last name twice, I wrote the first-ever fully sponsored book, and I'm currently selling my future. AMA!

Jason Zook
Mar 20, 2018

Hey peeps! I've been doing this entrepreneurial/startup thing since 2007 when I quit my completely biege existence (read: 9-5 job) to dive head-first into working for myself and wearing sweatpants most of the time.

I don't consider myself a conventional person and most of my weird entrepreneurial pursuits over the years are a reflection of that:

2007-2009 - I ran a tiny design firm with a few friends. We started with no connections and eventually designed Kanye West's MySpace page (for 808s & Heartbreaks).

2009 - 2013 - I created IWearYourShirt.com and generated over $1,200,000 by wearing sponsored t-shirts for over 1,600 brands.

2012-2013 - I sold my last name, two times, with an online auction (BuyMyLastName.com) that started at $0 each time and generated nearly $100,000.

2013-2014 - I wrote my first book, but didn't want to make zero dollars like 94% of first-time authors. I created a project called SponsorMyBook.com and was able to make $75,000 before a single word of the book was written. The book, Creativity For Sale, has never been a "best seller" but has made me over $90,000 and sold 10,000+ copies. 

2015 - Now - I've sold my future! Yep. Essentially I bundled all my software projects, online courses, books, etc, and built a community for creative entrepreneurs. The project was BuyMyFuture, but is now BuyOurFuture (includes my wife's projects too). As the name would suggest: You buy our future, but then you never pay us again AND continue to get everything we create - for-ev-er!

2016 - Now - I just finished my second book, and have a weird project before it gets published where I'm trying to get a book deal in a weird way: Dear Book Publisher.

I'm the co-founder of a couple conventional startups:

  • Teachery (an online course platform started in 2014)
  • Spruce Metrics (an analytics dashboard for people who hate analytics)
  • YourPack (a social directory for community owners)
  • ofCourseBooks (a collaborative workbook tool - sold in 2017)

Over the years I've also had a bunch of failures and bad ideas. I used to be a proponent of hustling/over-working. Nowadays I'm a believer in work/life balance, but only because I know it's something I'll work on my entire life.

My personal motto is: You don't get what you don't ask for.

Bring on the questions!


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How did you get the idea to sell your last name?
Mar 27, 9:56AM EDT0
What has been one of your biggest professional regrets and how have you used this regret to motivate you?
Mar 26, 3:06PM EDT0
Could you distinguish what you regard as a stylist, as opposed to a designer?
Mar 26, 1:38PM EDT0
What's your favorite t-shirt of all the tshirts that you wore and why?
Mar 26, 12:07PM EDT0
How do you feel about stretching yourself to learn new things?
Mar 26, 11:57AM EDT0
What are the top five books on your shelf?
Mar 25, 11:51PM EDT0
How do you make sure that your work continues to innovate and grow through the years?
Mar 25, 10:18PM EDT0
How do you measure the success of your projects? Is it all about how much money you make or do you have other ways of defining 'success'?
Mar 23, 3:51AM EDT0
What are your thoughts on the number of startups and entrepreneurs currently flooding the market?
Mar 22, 1:23AM EDT0
What, I your opinion, are some of the things a person should not sell?
Mar 22, 12:55AM EDT0
What exit strategy do you have in place in case you change your mind about the sale of your future?
Mar 21, 9:24PM EDT0

How often do you launch a new project? (just saw your BuyOurFuture page)

Mar 21, 3:15AM EDT0
Is being a successful entrepreneur a combination of talent, experience and education and why?
Mar 21, 1:48AM EDT0
What should young students who aspire to become entrepreneurs, keep in mind?
Mar 20, 11:56PM EDT0
What are the ways in which you enable yourself and your team to stay energized and produce their best?
Mar 20, 11:50PM EDT0

Have you ever thought of getting into the film industry at some point, and if so what kind of project do you think you would interest you?

Mar 20, 8:34PM EDT1
What professional and personal qualities have enabled you to reach the position you are at in the industry today?
Mar 20, 2:38PM EDT0

Not being afraid to be myself and know that will attract some people, while deterring a whole hell of a lot more people. We're conditioned to want everyone to accept us, but that only leads to a constant battle of trying to be accepted. I moved around a ton as a kid, so I dealt with rejection and not-being-accepted a lot. It was tough, but it's immensely helpful when you're trying to put your ideas out into the world (esp weird ones!). 

I realized early on in my entrepreneurial journey that taking feedback and criticism from people who weren't in the same arena I was in was dangerous. Friends and family are great, but if they haven't done what you're trying to do in life (or aren't in the pursuit of it), their feedback and thoughts can derail you quickly. 

I tend to have an unwavering inability to do things the same way as other people. It's a blessing and a curse, because on one hand it helps me come up with unique ideas and put them out into the world. But on the other hand I have a hard time doing "standard marketing" stuff that's proven to work (because it feels so boring and incongruent to who I am as a person).

One last thing is being willing to change. I was super stubborn 10 years ago. I thought I could do it all. I don't try to be a superhero entrepreneur anymore (I avoid the hustle, I'm okay with enough). Instead, I try to surround myself with a few great people, and do things my own way with my own definitions of success.

Last edited @ Mar 20, 3:06PM EDT.
Mar 20, 3:04PM EDT0
Do you think it's best to work in a team or work solo to produce something of utmost productivity and excellence? What are your thoughts?
Mar 20, 12:12PM EDT1

It really depends. For me, I belive in outsourcing my weaknesses. If there's a project I'm working on that can be built quicker (or I'm just completely lacking in certain skills - which I lack a lot of 😅), I will always work with other people. However, I'm extremely picky about partnering with someone, or simply outsourcing work to freelancers, etc. 

I know that I have extremely high standards, which can be difficult to meet when you're also trying to outsource on a budget. There have been times I've worked with other people, paid good money, and felt like it was a complete waste of time and effort. Those experiences are good because they show me that I need to do a better job of communicating what I'm looking for AND I need to make sure I'm working with people who have standards that match my own.

Sometimes working solo is the best way to START. You go as far as you can take a project, then bring on other people to fill the gaps you couldn't complete. 

Mar 20, 1:03PM EDT1
What did you do with the $100,000 that you got by selling your last name?
Mar 20, 9:48AM EDT0
What were some of the first things that you had to learn by yourself as an entrepreneur?
Mar 20, 3:28AM EDT0

Managing money is way harder than everyone thinks. When you get a paycheck on a consistent basis, it's 1000% easier to manage your money. When you have inconsistent income, you have to be ruthless with tracking it. I got into nearly $100,000 in business debt because I had no clue how to actually manage my money. The simplest advice I can give about this is to have weekly budget meetings and be honest about income/expenses. 

Another big lesson is time management. Much like money, when you work on your own your time can quickly get away from you (esp with wonderful creations like Netflix, YouTube, etc). I use Google Calendar to schedule out almost everything in my life and I'm a huge believer in analog to-do lists. I wrote more about this here: https://jasondoesstuff.com/time/

One more lesson: My pride used to get in the way a lot. Not wanting to heed the warnings of people who'd already been where I was trying to go, or at least learning from their mistakes (harder to do in practice).

Last edited @ Mar 20, 1:07PM EDT.
Mar 20, 1:07PM EDT0
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