Jason Zook’s creativity along with his resilience and go-getter attitude to consistently achieving targets that he sets for himself has inspired me to a great extent.
Today, I’d like to use this opportunity to channel his influence to you to feel inspired and motivated by his actions and entrepreneurial adventures, to be determined to try the same.
Jason Zook started his entrepreneurial journey with a project called “I Wear Your Shirt.” From 2008-2013, he made over $1,000,000 just by wearing T-shirts. The craziness didn’t stop there, he went to sell his last name twice.
He’s an entrepreneur, blogger, author and also runs his weekly podcast called the Action Army. He’s done all sorts of big, crazy projects and taken many risks throughout his journey without any fear of failing.
What Are the Most Influential Habits in Your Life?
A few years ago I decided to stop waking up with an alarm. That, and not looking at any social media, news, or email after waking up has been amazing. I still look at my phone first thing in the morning, but it’s only my Instagram feed and limited to 5-10 minutes (I don’t have social or news apps on my phone). After that, I do my own version of meditation, which is hand-crafting a cup of coffee for myself and my wife Caroline, with no technology, and usually, I’m skimming a Calvin and Hobbes book. Just another 5-10 minutes to myself, with no distractions, and a little bit of joy thrown in the mix. That morning ritual (called InstaCoffeeHobbes) sets the tone for my day.
Another big shift in my life that has been huge, has been moving to a vegan diet. And actually, it’s a whole-food vegan diet. Growing up I’ve adored animals. In another life, I would have been a Zoologist. But I also was a voracious meat-eater. I finally decided I couldn’t continue to eat meat for my own selfish desires, especially when plenty of humans are insanely healthy and active without eating meat. I won’t soapbox about the negative effects of the meat and processed-food industry. All that being said, my wife and I have been whole-food vegan for nearly 9 months and we’ve never felt better, looked better, or been happier.
How Do You Set Goals and Manage Time?
At the end of each year, my wife and I sit down and plan out the next year. About three months later, then entire plan catches on fire and we’re scrambling to figure things out. Okay, okay, it’s not THAT bad. But we do sit down and create rough projections for the year: What projects we want to keep working on. What new projects are on the horizon. Where all of our time needs to be allocated each month. And then we set extremely achievable financial goals for each project. Throughout the year, we have a weekly meeting (Mondays at 2 pm) and we go over our budget, our projects, and how we’re feeling about certain projects and our monthly/yearly projections.
Diving in a little deeper, I use Google Calendar like an assistant. And not just for business. I schedule taking my dog (Plaxico) to the vet. I schedule going to the gym and grocery store. I am pretty meticulous about blocking time on my calendar because it’s what makes the most sense to me and helps me be accountable. If I block two hours of time for writing, that’s all I’m doing during that time. Email isn’t open. Slack isn’t open. I’m ONLY writing. Maybe these tactics have fancy names, I just do the things that feel right and help me get lots of stuff done!
How Are You Modeling Your Life?
The 3.5-Hour Workweek, obviously! Haha. Kidding. There’s no model or framework I follow. We, as humans, are constantly evolving. What works for us now, will feel constrictive and uncomfortable in 6-months or 2 years. I focus on living my life through my values: Control and flexibility. Every decision I make gets filtered through those values, neither of which focus on money or someone else’s idea of success. (And family comes before those values, but that should be obvious.)
I don’t chase making a certain amount of money. I don’t focus on working a certain amount of hours. I do what feels right and I work on things that I feel are A. Making a difference in people’s lives (by being useful or entertaining) and B. Are different and unique.
I will say, because they have helped me get where I am today, these five books are fantastic and the ones I recommend the most: Pam Slim’s Body of Work, Kathy Sierra’s Badass: Making Users Awesome, Jason Fried and DHH’s Rework, Ryan Holiday’s The Obstacle Is the Way, and Greg McKeown’s Essentialism.
Can You Describe Your Work Process and Thinking Behind It?
For every project I work on, I follow a similar path: I come up with an idea, whether from a problem I have, a random crazy idea I have, or a problem I see that affects people that I have some experience with. Then I make that idea sit quietly in the corner for a week. If a week later that idea is still nagging at me, I allow it to have my attention. I’ll share the idea with a few people in my trust circle (people I trust who also create things) via email or Slack channels. They’ll usually have good critical feedback and I can test/tweak the idea from there. Then, I’ll almost always get someone to pay for the idea before I spend any time creating it or making it a real thing. I strongly believe if people will pay for just the idea, there’s a good chance other people will pay for the resulting product or service. Then, I build the smallest, best version of the product I can (I do a lot of my own design work but always outsource development to friends or friends of friends) and put it in the hands of the early buyers. What do they think? What do they like? What else do they want? What sucks? I also share it with my trust circle again.
From that point, I tend to have a workable prototype. I look at the immediate must-have features and build a long-term features list as well. I try to think 6-12 months ahead of time, just to make sure I’m building something that still meets my values and my interests. If it does, I’ll usually build a pre-launch website of some sort, build some buzz through my email list and maybe social channels, and start talking more about the project until it launches. Then, when I’m getting ready to launch, I write out low goals and high goals for the launch. The low goals are realistic customer and revenue numbers that I know I can hit with just my own effort, the high goals are pie-in-the-sky numbers just for fun. For me, a product launch is never the finish line, it’s actually the starting line.
I write all my own copy but have an editor (Chantel Hamilton) who is amazing. My wife Caroline is also critical in the planning of my projects, but also the crafter of the words. As mentioned, I tend to do most of the design work. And believe it or not, Google Calendar and a pad of paper are my trustiest to-do apps.
What Do You Eat for Breakfast?
95% of the time: Rolled oats with coconut oil, chia seeds, coconut or almond milk, cinnamon, and a smidgen of salt (yes, 1 smidgen). The other 5% of the time I make biscuits from scratch, usually a vegan recipe from The Minimalist Baker that’s amazing. My wife calls me the “biscuit fairy” on these mornings.
No thoughtful reason why these breakfast choices. I just like them and I’m too old to eat Fruity Pebbles.
How Do You Train Your Body and Mind?
Body: My wife and I do weight training 3-4 days per week. I’m our personal trainer, but not because I studied that, I just enjoy picking random exercises for us to do. We typically always super set 2-3 movements together. For example, we’ll do 12 bicep curls, to 12 shoulder presses, and then 12 squats all with dumbbells in hand. We keep workouts to 20-minutes max. Lots of fun music blasting in the background, with random dance breaks. I try to do yoga 1-2 times per week, but it’s very short and just to get my body moving while I’ve been standing at my desk all day.
Mind: I read and watch almost nothing online. I’m juggling so many projects at once that I learn by doing. Which, as we all know but rarely admit, is the best way to learn. I realized a few years ago that reading books by well-accomplished people is great, but it’s useless unless I work my own way and apply their tactics where it makes sense. There’s no one-size-fits-all formula for anything, so I just do what feels right at certain points in my life. That and I know how easy it is to get sucked into reading and watching more things, instead of actually creating and working.
How Do You Meet and Connect with People?
I’ve mentioned how quickly life changes a few times, and this is one area that’s changed drastically for me. I used to do a lot of public speaking and loved being at conferences. There’s a fantastic energy at in-person events and I strongly advocate people attend them. But, I’ve moved away from that phase of my life. The same can be said for social media: I was super active on all platforms, especially Facebook (and any new platform that popped up). I’m curious by nature and loved trying a new app or service. But then I stopped one day and realized I was doing it for the wrong reasons. I wasn’t just being curious, I was trying to be popular. Trying to get more Likes, RTs, etc. Ew. So I stopped. I quit Facebook. I tweet very infrequently. I look at Instagram once, maybe twice per day. My use of social media has decreased to 2% of my overall time (and I know that because I did a 30-day experiment tracking my time recently!)
Where I do spend the majority of my time connecting with people is my email inbox and Slack. I love these two communication channels for two different reasons.
Email: I love the one-on-one-ness of email. If someone sends me an email, I reply. There’s no assistant. No man-servant. Just little ole me. And I love that. I know it matters to people because it mattered to me 12 years ago when I emailed Seth Godin out of the blue and asked him a marketing question. He replied! I was through-the-roof excited at the time (I was also working at a 9-5 job I hated at the time). That simple interaction with a popular guy like Seth Godin set me on a path to always be accessible and available to folks who may look up to me and want to email me and ask for advice. Whether I have any worthwhile advice is a topic for another conversation!
Slack: I have one main community now, the BuyOurFuture community. These folks have purchased lifetime access to everything my wife and I have created, or will ever create in the future (hence the name). It’s an amazing group of 300+ entrepreneurs, small biz owners, artists, musicians, doctors, heck, there’s even a professional bowler in the community! I spend all day hanging out with these folks and chatting with them about life, work, and other random things. The other Slack channels I use are for collaborating on my many projects. Slack is fantastic for one-on-one or small group conversations about project to-dos, customer service, etc.
What Are Your Sleeping Rituals?
Sleep is next on my list to life-hack. I’ve slept terribly for as long as I can remember. I toss and turn all night. ALL NIGHT. It sucks. Various activity monitors have told me I get about 2-4 hours of restful sleep each night. I’ve even gone to an ENT doctor to see if I had sleep apnea, which thankfully I do not have. I can feel the effects of my lack of sleep and I’ll be starting to experiment with different things to see if I can find a solution.
I’m almost always in bed by 10 pm. I read on my Kindle, always a fiction book, to wind my brain down. I wake up, alarm-free, between 630-8 am every day.
What Are Your Investing Habits?
My wife and I spent 2013 – 2016 paying off $124,000 in debt. That debt was business debt, life debt (credit cards), auto debt, and student loans. During that time we worked with some awesome financial advisors who helped us craft a better plan to handle our money flow. We barely did any investing during that time, in fact, we only invested in our whole life insurance policies. Every dollar we made or saved went to obliterating that debt. Debt article(s) if interested: The Simple $100,000 Debt Payoff Plan You Can Accomplish.
Once we paid off our debt, we started building up our savings buffer (which we kept in a bank account not connected to our biz + household checking accounts – so we can’t see it or easily touch it). A good friend, Greg Hartle, once explained to me the value of investing in yourself first (well, actually, it’s protection first: hence the whole life insurance). But, by focusing on investing in yourself first, you pour money into your own ideas and products. This works extremely well for me because I create a lot of things. I always have ideas. The BuyOurFuture idea is a prime example: I invested about $25,000 of my own money in building out the idea before it was public and in just three months it netted me $178,000 during the first release in late 2015. You can’t get that type of return anywhere else, and I get to keep all the money and reinvest it in future projects.
I believe in the idea of diversification, so I’m sure I’ll start investing in things like index funds, or whatever all the financial wizards tell me I HAVE to be doing, but I like controlling my own money. I like being the influence on its growth. And I realize, like everything else in my life, that may change completely in a few years.
Our biggest yearly expense is travel, because I don’t want to enjoy my money when I’m old. I want to enjoy and create memorable experiences while we’re able. For me, retirement isn’t even something I think about, because I truly love the work I do. Retirement is something you do from work you hate.
As far as simpler/smaller things: I love voting with my dollars and giving back to fellow entrepreneurs. My friend Jeff Sheldon from Ugmonk is a great example. I’ll buy anything he creates, because I want him to keep creating stuff. Tom and Dan from StudioNeat are the same way for me. I consider myself a minimalist and try not to buy too much stuff, but I also am okay to spend money on products created by people who I hope keep creating awesome products.
What Books, People, Experiences Shaped Your Thinking?
One of the biggest life changing experiences in my life has been the introduction to minimalism. In 2013 I listened to a well-coiffed man talk about his experience with debt, owning too many things, and subscribing to a life that felt foreign to him. That man was Joshua Fields Millburn, from The Minimalists, and his story felt akin to my own. I nearly cried after hearing him talk, because it showed me how many things I was striving for in life that were the wrong things for the wrong reasons. I’ve since applied my own flavor of minimalism to my life and it’s been outstanding. From selling everything we owned and moving across the country, to only owning 7 t-shirts, to constantly asking myself “do I need this thing, or do I just think I do because of carefully crafted marketing and advertising?” I’m a proud minimalist who owns more than 1 chair and 1 wooden spoon.
Walking away from a $1M business was probably the most pivotal move in my business career. IWearYourShirt, the social media marketing company that put my name on the map in 2009, went from an idea in my closet to $500,000 per year faster than I could blink. But I wasn’t ready for everything that went along with running that business. Nor did I actually want all the stress and anxiety that came with scaling up, adding employees, and constantly being in the limelight. I don’t regret IWearYourShirt for a single moment as it gave me everything I have in business today, but I learned so many tough lessons from 2008-2013 while that business was active.
As far as books go: Seth Godin’s book Purple Cow was huge for me in the early 2000’s. It catapulted me from stuck 9-5 er to budding entrepreneur by showing me I should embrace the feelings I had buried inside me that I was unique and could stand out. Ryan Holiday’s book The Obstacle is the Way introduced me to stoicism and has been instrumental in helping me how to stay level-headed and embrace mistakes and failures. I read about 30 pages of Cal Newport’s book Deep Work and immediately got the concept and continued what I was already doing by being hyper focused on individual things at a time.
And last, but certainly not least, my wife Caroline has been the best thing to happen to me since that vegan biscuit recipe! She keeps me grounded. Is the brains between the two of us. Has creativity to match my weirdness. And we’re a constant support for one another. It may be cheesy, but it’s true and I’m proud to end this interview by mentioning her!