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Why I Stopped Running A $1,000,000 Business and How To Know If You Should Quit Your Business

Wandering Aimfully Through Failure

Why I Stopped Running A $1,000,000 Business and How To Know If You Should Quit Your Business

For five years I poured everything into a dream idea until I simply couldn’t do it any longer and had to walk away. Let’s find out if you should quit your business.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Did I ever tell you about the time I ran a $1,000,000 business? I think most of you are familiar with my time as the IWearYourShirt guy, and if you’re not, you can read the whole story in my first book. In a nutshell, I came up with a crazy idea in 2008, ran my butt off for five years to grow it and scale it, made seven figures in revenue, accumulated six figures in debt, hit my breaking point, and then shut the whole thing down and walked away.

My first failure in business. Womp womp.

But now that you know the end of the IWearYourShirt story, let’s back up half a sentence to that breaking point I mentioned. What was it, how did I realized I’d hit it, and what triggers should you be watching out for in your own business?

After generating $1,200,000 in revenue in five years, I decided to shut down my IWearYourShirt business and completely walk away from it.

When IWearYourShirt was growing, so were the dollar signs in my eyes. THIS WAS THE NEXT BIG THING! (I told myself.) I made nearly $90,000 the first year, and it was loads of fun. I was getting press and media attention around the world. I had big-name companies reaching out to me. I had “fans,” which was really odd.

Jason Zook IWearYourShirt in 2008

(A hilariously awkward walk down memory lane: The first “photoshoot” I did for IWearYourShirt promo photos.)

During the first year of IWearYourShirt, I received more external validation than I had had in my entire life. Up until that point, I was a nobody. I’d done nothing worth talking about. This was my moment to shine. The external validation showed up in many ways:

As time went on with IWearYourShirt, I craved more. More validation. More growth. I saw other entrepreneurs becoming successful at the same time and I wanted to be on the same “level” as them.

I read stories about startup founders getting venture capital funding, and I wanted that. I heard about companies hiring lots of employees and that sounded like something I should be doing. I heard all the multi-million dollar valuations and assumed that’s what I should be striving for. Everything I was thinking was growth-focused, and if you’re a smart cookie, you might know where that train was heading.

In 2011, I saw my first glimpse that there might be an issue with the IWearYourShirt business model, and the business itself. The way IWearYourShirt made money was by putting an incremental price on each day of the calendar year. This meant that the early months of the year didn’t bring in a ton of revenue. Add on top of that I was trying to grow the amount of shirt wearers (employees) in IWearYourShirt (who all required a standard monthly salary).

Here comes the not-so-delicious recipe for business disaster and when you know it might be time to quit your business…

While IWearYourShirt had a decent cushion of money in the bank from the first two years, I still lived off that money. When January 2011 rolled around and I needed to pay $25,000 in employee salaries and business expenses, the shirt-wearing calendar had only generated $2,500 in sales. I knew we were in trouble. The cash-flow of IWearYourShirt just didn’t make sense, neither did me trying to take on ALL the roles in the company: CEO, CMO, CFO, COO, any C’s and any O’s, I was doing it. Oh, and I was also still the head shirt wearer, donning a shirt, creating content on social media sites, filming a YouTube video, hosting a 1-hour live video show, managing customers, and answering upwards of 300 emails per day.

You can hear that disaster train screaming down the tracks, can’t you?

I was able to juggle money, rob Peter to pay Paul, and borrow money from family, but all of that only lasted until early 2012 (when I tried to continue growing, without fixing the actual flaws in my business model).

By the summer of 2012, for the first time in my life, I had accrued business debt. And it wasn’t just a few thousand dollars. I was in the hole over $75,000.

I can distinctly remember those summer months in 2012. Asking myself: How the hell did this happen!? Everything was going so great??

IWearYourShirt was being talked about everywhere. I was living the so-called entrepreneurial dream. Yet, here I was, in debt, completely stressed out, insanely over-worked, and not seeing the writing on the wall. Something had to change. Something had to give. The disaster train was continuing to bear down the tracks toward me.

When everything is crumbling down around you with your business, you will reach a breaking point.

In 2013 I attended a conference in Fargo, North Dakota, where I was a featured speaker for a small, but awesome, group of fellow “misfits” (entrepreneurs, doers, thinkers, artists, musicians, etc). The event was appropriately called Misfit Conference.

Jason Zook at Misfit Conference 2013

When I took the stage, everyone expected to hear my story of t-shirt wearing success. Many folks in attendance had heard of “the t-shirt guy” and were ready to listen to all my business victories and triumphs. But something in me just couldn’t do it anymore. Something in me couldn’t pretend everything was okay. I was in debt. I hadn’t had a good night of sleep in months. I gained nearly 50 pounds. I had just let go of a few employees to be able to afford to pay our bills.

Instead of telling my story of success (which I’d told countless times from countless stages before that) I shared my failure-ridden behind the scenes of IWearYourShirt.

I don’t remember exactly what I said. I remember the beginning as I held nothing back and shared how I was chasing all of these growth metrics and other people’s ideas of success. And then I remember the end of my talk, seeing tears in some of the audience member’s eyes as they stood and clapped. It was a complete blur for me, but apparently sharing all my mistakes and failures really resonated with my fellow misfits.

As my wife, Caroline, and I flew home from that conference, we sat on the plane and had a tough conversation about how we were living our lives and how IWearYourShirt was impacting us (my wife worked for my company for the last two years). After listening to other speakers at the Misfit Conference share stories of minimalism, avoiding the trappings of society, and carving out your own path and definition of success, all the light bulbs seemed to go off for us. For five years IWearYourShirt had been an incredible ride, but the time had come to step off that ride and get on a new, less bumpy, rickety, unpredictable, and soul-sucking ride.

How to know if you should quit a business?

How did I go about quitting my business and how can you decide if you need to quit running a business that’s no longer serving you?

Something I did, and that we should all do more often, is to check in with ourselves. To answer questions like these:

Every decision I’d been making with my IWearYourShirt business was based on external ideas of success: More customers. More employees. More money. More attention. More, more, more.

But when I really sat down to think about it, those weren’t the things that made me happy. What made me happy was having a comfortable amount of money, but not gobs of it. I enjoyed the personal validation of sharing my crazy ideas and antics, but I didn’t need tons of people to see those things or give me praise for them.

Drawing a line in the sand is the first step to walking away from a business that needs to be shut down.

In the Spring of 2013, shortly after attending the Misfit Conference, my total amount of business debt hit $100,000. This debt was owed to family, spread across multiple credit cards (7 of them), and was bills outstanding to vendors we’d used. $100,000 was my line in the sand and I didn’t know it until it happened (please let you number be WAY lower!).

By this point I knew my business had to be shut down. It was limping along, barely supporting us financially, and sucking every last ounce of money, creativity, and energy I had.

On May 6, 2013, I closed the virtual doors of IWearYourShirt. I let my remaining employees go, including myself and my wife.

I didn’t have a plan of attack moving forward, but I knew I had to make a drastic change if I was ever going to get my life back and enjoy working for myself again.

I hope, for your sake, your line in the sand doesn’t have to be $100,000 in debt, being 50 pounds overweight, or feeling like your life is completely out of your control. I hope you’ve made the realization that your business model is broken or that you’re running a business that you don’t truly believe in any longer.

You don’t need to know what to do next to make a difficult decision.

When your business starts trending in the wrong direction it can feel like all the walls are crumbling down around you. Without a clear path laid out in front of you, you’ll want to stick to the only (broken) path you do have. But the longer you stay on a broken path, the longer it takes to find your next path.

For me, in 2013, I didn’t have a next step. I didn’t have another business idea. But I had built something. For five years I’d run a company that brought in a substantial amount of revenue and provided jobs for a handful of creative people (as well as opened a ton of doors for me). Not everything I’d done during that time was wasted effort, and I could use the lessons I’d learn to move forward.

Similar to how IWearYourShirt got off the ground, I started emailing a few entrepreneurial friends for advice. It was only 10ish people in my trust circle, but one person wrote back with a really helpful question. He said something to the effect of:

“Jason, what do people ask you about the most? Would could you teach from your years of experience?”

That was actually an easy question for me to answer: People emailed me constantly asking how they could go about getting a paid sponsorship for their blog, event, etc, since I’d been able to secure so many t-shirt sponsors (and others) during my IWearYourShirt run. The answer to that question led to creating my first online course, How To Get Sponsorships For Anything. The initial launch of that course brought in $32,000 and has gone on to generate over $150,000 in total revenue (plus help me create my first software product: Teachery). Sure, there was a ton of hard work to do all of that, but it was an entire new path I never saw coming.

One of the most important things you can do if your business is struggling, or if you feel lost, is to reach out to someone with experience and talk to them.

After my talk at Misfit Conference, a woman named Pam Slim walked up and gave me a huge hug. Pam and I had chatted on Twitter a few times, and even seen each other at other events, but this was different. She looked me in the eyes and said, “Jason, please call me and let’s chat.” (I’m sure there was much more said, but that’s what stuck in my mind.)

Now, it’s worth mentioning, because I want to let you know it’s okay if you don’t ask for help right away. It took 8 months for me to gather the courage to call Pam. I’m not joking. I thought about her offer nearly every day, but I was scared. I was embarrassed at what she would think. And I had convinced myself that I could figure everything out on my own (stupid male pride!) Getting on an hour-long call with Pam was one of the best things I ever did after shutting down my business. The thing that stood at the most during out chat, and has continued to resonate with me for years, is that Pam explained that IWearYourShirt being a failure didn’t mean I was a failure as a person. Businesses fail every day and I should take the lessons (good and bad) that I learned from IWearYourShirt and move on to whatever was next.

I implore you to find the Pam Slim in your life. They may be an email connection away. They may be someone who’s written a book you’ve read. They may be some sort of business coach you’ve heard about. Heck, they could simply be a family member who’s had business experience.

The important thing is that you talk to someone and don’t try to figure everything out on your own.

Another tip here: Read the book The Obstacle is the Way. I wrote an article entirely about this book as I think it’s the most important book I’ve ever read. I highly highly HIGHLY recommend that book!

Only you can decide to quit your business

It’s up to you to decide if you should walk away from your business, but walking away from my business was one of the best decisions I’ve ever made.

Looking back, it’s easy to see ALL the writing on ALL the walls. I was obsessed with external success metrics and thought I could feel better by constantly striving for more.

I never took the time to establish my core values. To actually write down what things would make me happy. Instead I just picked things I read about in articles, saw on TV, or heard friends gushing about.

I wouldn’t go back and change anything during my IWearYourShirt experience from 2008-2013. The ups, the downs, riding the disaster train, all of it shaped me into the person I am today.

I learned so much about how to NOT run a business. But more importantly, I learned how to measure success through internal validation first.

I continue to learn lessons every day from those five years. I know they’ll continue to provide me immense value, and I hope my story might inspire you to take a hard look at where you get your validation and if there’s a tough decision you need to make about a business that’s no longer serving you.


Thanks to Caleb Campbell for asking me to write this article originally for Why I Stopped.

Why I Stopped Running A $1,000,000 Business and How To Know If You Should Quit Your Business

(Big Fat Takeaway)

Quitting a business doesn't mean you're a failure. Quitting something that is no longer serving you creates space for something new.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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