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Jason Zook

Entrepreneur who made $1,000,000+ wearing t-shirts. Most recently sold his last name (twice) and his future

THIS CHAT HAPPENED ON January 19, 2016

Discussion

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Jason Zook@jasondoesstuff · I do weird things on the Internet.
I’m that crazy guy who made $1,000,000 by wearing t-shirts on IWearYourShirt.com. I’ve also sold my last name (twice), wrote a fully-sponsored book that didn’t suck, gotten out of $100,000 in debt, and recently sold my future. I consider myself a minimalist and try to live an intentional and authentic life. I’m Jason Zook, ask me anything.
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Carey Beth Elder@eldercb · Marketing, AOL Alpha
@iwearyourshirt If you had a new app to promote, how would you do it? Let's just say you had $10,000 to spend.
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@eldercb oooh, $10k? I'd put that in the bank and save it for dev costs and customer service costs (and probably product improvement costs). Then I'd immediately go to my email inbox and make a list of 50-100 recent people I'd emailed (friends, family, etc). I'd share the app with them and why it was going to change their life. I'd asked for them to try it. Use it. Give me feedback. I'd take that feedback with a grain of salt and see what patterns emerged from their responses. Then I'd improve the app and reach back out to all of them, or 50 new people and ask them to check it out and share it with friends. I'd keep this process going until people couldn't stop talking about the app because of its awesomeness. I don't believe in spending a dime on marketing or promotion until people are craving the product/service.
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Seth Mcleod@sthmcleod · Designer & Developer
@iwearyourshirt @eldercb This is such great advice!
Ryan Hoover@rrhoover · Founder, Product Hunt
Jason! You've come up with some wild money-making concepts. What's the craziest idea you've come up with but haven't done (yet)?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@rrhoover oh hello Ryan! I shared some of my stupid ideas with @daveitferris' question. But truthfully, BuyMyLastName and BuyMyFuture are the two craziest ideas I think I've had. I was pretty scared to auction off my last name. I expected the backlash to be huge. Luckily, I think everyone already knew I was crazy. Hah.
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Kate@katesegrin · Head of Social @ GitHub
Who are some of the people who have made the biggest impact on your life? (Stories, please!)
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@katesegrin wow. great question. off the top of my head: Seth Godin: For writing "The Purple Cow" which I read while working a 9-5 job. More on this story here: http://jasondoesstuff.com/average/ Joshua Fields Millburn: For showing me the ways of minimalism and giving me the phrase "does this thing bring me value." My Mom: Always supporting every crazy idea I've had... She had so much patience! My girlfriend Caroline: We've been together for nearly 6 years and we've helped each other grow immensely. I think I help her with the business stuff and she helps me not be an emotionless robot. Haha. Ryan Holiday: For writing the book "The Obstacle Is The Way" - This book gave me permission to be okay with my mistakes and failures and see them as important moments in my life. I don't know Ryan at all, but his book is amazing. Pamela Slim: Pam gave me a huge hug after I poured my heart out on a stage in 2013. It took me 8 months to gather the courage to have a phone call with her about feeling lost in life. I owe her a lot for taking that call and helping me through a rough patch. Everyone who subscribes to my email list: This sounds so silly, but those folks (and some Action Army'ers are here) mean the absolute world to me. You could take away every social media site and I'd be fine because I know I have a great list of humans who like my weirdness and support my projects. I'll forget other important people and they'll email me and yell at me: SORRRRY!
Ben Tossell@bentossell · newCo
What would you do if you were 22 today?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@bentossell let's add a bit more context to this... I'm me, just graduated (shitty) college, and I don't know what I want to do with my life. I would set a plan to try to intern/work for cool companies I admire for 3-6 month stints. Startups. Big companies. Local businesses. Try to soak up as much knowledge and experience as possible to figure out what I would want to be doing. I'd also keep learning CSS/HTML because it's a skill that never gets old if you own an online business. Oh, and I'd take shots of Goldschläger because... 22.
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
A few people asked questions about how I'd actually do this. So here are some additional thoughts: 1. I'd make a list of all the awesome companies that I want to spend stints at. Put them in a Google Doc. Probably start with 10-15 companies. 2. I'd research them. I'd add notes to each one of them in said Google Doc. This research would include what they do for marketing, who they target, who are people active on social media that work for the company. Do I know anyone who might be connected to them? I'd research that and write it down. 3. In that same document, I'd write thoughts on what value I could provide or if I had any ideas for their business. I'm not going to help them make an extra $10M in 6 months, but bringing creative ideas to the table always helps. Plus, it shows I have initiative and I'm not looking for a free ride. I would also outline what a 6-month plan could look like and why it's valuable to them that I will only have a short time period, but I'll be super motivated. 4. I'd create creative pitches for these companies. This wouldn't just be an email. I'd create simple landing pages or short videos explaining why I'd be a good fit and what I could do to help out. I'd only use email to send the creative pitches to them. 5. I'd start pitching the companies one-by-one and do them in batches of 3-5. This way if some say no, I'm not waiting forever for each company. I'd most likely create a Google Spreadsheet to keep track of my email pitches and subsequent follow up emails (because those will be necessary - you have to follow up). 6. I'd expect to hear NO, so I'd keep believing in myself and learning from each company that turns me down. Never assuming that just because they don't have room for me in their company that I'm a bad person, unqualified, or are not worthy. 7. Once I landed the first company, I'd start working with them, but I'd continue my journey of pitching other companies so I could have a few lined up. I'd try to focus 90% of my time working for the company that said YES and 10% of my time focusing on trying to land the next company for a 6-month stint.
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Daveit Ferris@daveitferris · Heartfuse
@iwearyourshirt I'm pretty certain you've considered an idea that ultimately was even too outlandish, even by your standards - can you share one or two of those and why you didn't follow them through?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@daveitferris hmmmm... what weird thing haven't I done that I've thought of? Probably creating spanx for guys. Just reading that sounds terrible huh? This was during my time right after college when I was trying to figure out how to do something besides a 9-5 job. Oh, I also wanted to start a "mail your enemies dog poop" business. I'm glad I didn't follow through with that.
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Daveit Ferris@daveitferris · Heartfuse
@iwearyourshirt @daveitferris Terrific! Thanks for my next two business ideas! 5% cut sound fair?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@daveitferris hah! Can I have a board seat too? ;)
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Daveit Ferris@daveitferris · Heartfuse
@iwearyourshirt @daveitferris we'll talk about that on Spanx Saturday. Don't be late!
Ben Tossell@bentossell · newCo
What is your favourite idea that you've worked on?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@bentossell You can't pick just one baby! But seriously, IWearYourShirt has provided me with so much over the years. My start. Growing an audience. Giving me the permission to be my authentic self in everything I do. And one heck of a rolodex to use for all my future ideas. Even though that business "failed" at the end, I wouldn't change a thing from it and appreciate it so much more each and every day.
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Alp Behar@alpbehar · Co-Founder, Upicnic
If you were to take money out of the equation, what would you say is the best thing you did?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@alpbehar selling my future. I'm giving people maximum lifetime value of my work. Regardless of the money, it feels really cool to know these people believe in me enough to buy into something so intangible.
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Chaib Yusuf@chaibyusuf · Creative Entrepreneurship Trainer
@iwearyourshirt how to discover our passion ? & when we must stop working on a project even if we love it?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@chaibyusuf If you have to "discover your passion" then I don't know how to help you. You should know what you are passionate about. Write it down. Keep it in front of you. If you want to build a business around a passion, be careful. Instead, find something you're really excited about and that you think can make an impact on people's lives. This article I wrote might help you (it came from a lot of people emailing me asking the same question you just asked): http://jasondoesstuff.com/start As far as stopping working on a project? That's really hard to figure out. I think it's okay to quit things though. Quitting frees up time for new things and new opportunities. Too many people (and I'm guilty of this too) get stuck in sunk cost bias. We've spent time/money on a business and don't want to let it go. If it isn't working (making money or helping people), then stop and move forward. But also don't give up after a month. If you want to build something of worth and value, it's going to take time. I'm in my 10th year of being an entrepreneur and I only feel like I'm starting to figure all this stuff out!
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Chaib Yusuf@chaibyusuf · Creative Entrepreneurship Trainer
@iwearyourshirt @chaibyusuf " Choukran ^^ " it's the arabic " Thank you "
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Marta Antonelli@antonelli039 · Co-Founder, Upicnic
@iwearyourshirt I don't mean to get too personal too fast, but what do you want your legacy to be?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@antonelli039 I don't think about legacy at all. I believe that if you care about what legacy you're going to leave, you're focused on the wrong things. I know that wasn't what you meant, but I just wanted to make that point. If I'm being 100% honest, I don't care if anyone remembers me in 100 years. I'm a spec in an enormous timeline. Probably not the sexy entrepreneurial thing to say, huh? What I do believe is that I want people to know I am 100% truthful and honest. I'd love to be remembered for being unique and helpful, but I'm not naive. I don't have a huge spotlight on me or the pressure to do ridiculously world-changing things. I like the tiny glimmer of light I have.
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Marta Antonelli@antonelli039 · Co-Founder, Upicnic
@iwearyourshirt Being remembered as truthful, honest, unique and helpful sounds like a pretty great legacy to me. But I love the point you're making. Being an entrepreneur is often associated with delusions of grandeur - plus, who am I kidding, we all want to do well for ourselves. But I find utterly refreshing to find someone who has achieved and is still relatable and down to earth.
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@antonelli039 👍👍👍
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Chaib Yusuf@chaibyusuf · Creative Entrepreneurship Trainer
@iwearyourshirt it seems that you're a multitasking person ... what are the skills needed to work on diffrent creative projects in the same time ?!
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@chaibyusuf I believe multitasking can work, when you don't actually multitask. :) I write down daily to-do lists and force myself to block off time on my calendar for tasks. A couple things that help me get a lot done: Not keeping my email inbox open all day. Closing all social media sites and removing those apps from my phone (along with all other notifications). And figuring out when my maximum output times are for certain to-dos. I wrote an article about getting in your "creation zone" http://jasondoesstuff.com/consum... With a few of my projects I have great partners. So I can rely on them to do things I'm not good at (my weaknesses). I try to always partner with people who have opposing skill sets, otherwise, we'd both be trampling all over each other.
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Farmer Brad, LLC.@farmerbradllc · Owner - Hobby Farmer - Farmer Brad LLC.
@iwearyourshirt If you were to make a minimalists mobile app like Tinder what question would you have it ask?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@farmerbradllc I don't even know what this means... haha
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Charles Alexander@charlesalexnder
"This is not your practice life." - Best sentence I've read in weeks. No question from me, just thanks to you for being awesome.
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@charlesalexnder I give all the credit to my buddy AJ Leon for that one. He's an incredible writer. More of his work here: http://aj-leon.com/pursuitofever...
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Preston Long-Lamoureux@pmlonglamoureux · @Prog_Code Staffer | Progressive
@iwearyourshirt -only if i knew how to get one.. lol If you could change one decision that you have made in your past, what would it be and how would that change where or who you are today as a public figure?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@pmlonglamoureux I think the only change I would have made would have been to skip college and continue dabbling in building websites and things on the Internet (this was 1999). Instead I went to college and skated through it for five years, losing all my entrepreneurial steam until 2007. But honestly, that may have changed my entire trajectory of where I am today. I fear the butterfly effect... 😁
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Emily Hodgins@ems_hodge · Operations @ Product Hunt
@iwearyourshirt how many T shirts did you have to wear?! What does 'a day in the life of Jason' - look like?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@ems_hodge Hi Emily! So, from January 1, 2009 - May 6, 2013 I got paid to wear over 1,600 different t-shirts. In that time I amassed about 3,000 t-shirts (lots of people sent me random shirts in the mail, it was weird). Nowadays, I own about 40 t-shirts and I get my favorites from CottonBureau.com - I love supporting aspiring creative folks! My day? I bet you'd find it really boring... I wake up around 7am and check Instagram only on my phone (no alarm or anything). I don't have social media apps on my phone anymore. After 5-10 minutes of scrolling through beautiful photos I get up and make coffee (chemex or french press). We have a Bluebottle Coffee Subscription (so good!). I make coffee for 5-10 minutes with no technology. None. Some days I'll read Calvin and Hobbes while making coffee (it's the best, ever). Then I got to my desk and read and answer emails. For about 30 minutes I'll do this and then I'll spend an hour writing. Whether it's article ideas, business ideas, or just random thoughts. I've written over 1,000,000 words in the past two years and thrown away 90% of them. The hours between 9am - 5pm are spent working on all my various business ventures, doing interviews, answering emails, etc. I only check social media a few times in the day (only once for FB). At 5pm I walk my awesome dog Plaxico with my equally awesome girlfriend Caroline. The rest of the night is a complete crapshoot. Hah. I'll either work, read, relax, exercise, or go see a movie. All that being said, some days I only work for 2 hours and spend the day reading or offline. I used to be a workaholic and live the HUSTLE life. Now I just want to enjoy the life I've created for myself through my work.
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Chris Johnson@chrisjohnsonco · chrisjohnson.co
@iwearyourshirt What is your process of choosing topics to write about for The Action Army? What topics or ideas didn't make the cut?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@cjhnsn_ love this question! So I have a Google Spreadsheet that keeps a schedule of sorts for me. I keep a running list of topic ideas in it, just to keep me on schedule. Then I use the Letterspace app (I'm sure it's been featured here on PH) to write thoughts about each article. I tend to give myself 30 minutes per topic and then walk away from each topic for a week or two. Whichever topics keep nagging at me, I revisit and keep writing about. The ones that I think will help people and that have made a big impact for me are the ones I tend to share. I ask a question in the welcome email when someone joins the Action Army: "What's the ONE thing you're struggling with right now?" I've gotten a ton of article ideas from people sharing their struggles (many of which I've been through!). Also, I reply to every email I get through my website. When I notice patterns (repeated questions), I turn those answers into articles.
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Kate@katesegrin · Head of Social @ GitHub
What was the revelation that drove you to live minimally?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@katesegrin Great question Kate. I sat in the audience at a small conference in Fargo, North Dakota in 2013 and listened to Joshua Fields Millburn share his story of minimalism and starting TheMinimalists.com. At that same moment I was $100,000 in debt and was not happy at all (if you can imagine). He and I had a couple things in common and I think those commonalities really inspired me to do something. Trying out minimalism is one of the best decisions I've ever made. I'm soooooo much happier with less stuff. It has really realigned my entire life and what shown me what I value most. I don't mean to drop links in this AMA, but I interview Joshua (a few years ago) and loved his answers: http://jasondoesstuff.com/interv...
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PopGeekHeaven@popgeekheaven · Head Geek, Pop Geek Heaven
@iwearyourshirt SaaS question: you've created a really good SaaS app(Teachery, which I use)! Now, I'm an experienced product creator, selling full-time online for 20 years now..but I've never created a proper recurring product - yet. That's changing in '16. Question is: if I decide to go a SaaS route and keeping in mind my left brain is quite limited and I would need a programmer partner(like you did w/ Teachery), what are the three key things I should keep in mind when evaluating the opportunity with SaaS?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@popgeekheaven SaaS is tricky. Even with Teachery, we aren't swimming in MRR. I'd actually read every damn thing @nathanbarry has written about building ConvertKit.com. He took that SaaS business from something small to a $1M annum biz. Really really impressive stuff. He's way smarter than I am and I continue to learn from his experience. (Thank you for using Teachery btw!)
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PopGeekHeaven@popgeekheaven · Head Geek, Pop Geek Heaven
@iwearyourshirt @popgeekheaven EXACTLY what I've been doing w/ tracking Nathan Barry for the last two years - swallow it all by him, esp. on this subject. (I'm a CovertKit customer, too...)
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Mutasem Dmour@mutasem_dmour
@iwearyourshirt as someone who's about to graduate college with an engineering degree, what advice do you have?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@mutasem_dmour Check out the answer I gave to @bentossell about being 22 :)
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Jay Wallace@mootpt · Entrepreneur
How important is getting there first with regards to novelty ideas?
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Jason Zook@jasondoesstuff · I do weird things on the Internet.
@mootpt everyone has ideas, execution is what's most important. When I started IWearYourShirt people had been paid to stand on sidewalks and wear companies shirts before. I just took the idea in a unique direction that was all my own. There were tons of copycats, but I stuck to what made me different and poured as much of that (and extra hours) into executing my idea. Truthfully, I think competition in any business (or idea) is great. It proves people are willing to pay for that thing!