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Watch Us Build Our Next Business, Wandering Aimfully, In Real-Time

Watch my wife and I build our next business (Wandering Aimfully) in real-time! This is no small feat for us. I’ve been hinting at this project here and there, including a mention in my State of the Union at the beginning of this year. This is the business baby my wife and I are having together[…]

Keep Your Standards High and Expectations Low to Succeed in Life

Whether you’re just getting started, working on a new project, or simply trying to fight self-doubt, keeping your expectations low and your standards high is the ultimate plan for success. It isn’t easy to become a great designer, speaker, painter, musician, business owner, etc. Becoming great at anything requires having the opposite of what people[…]

Do You Have To Practice Meditation To Live A Happier And Healthier Life?

I know I’m not alone in seeing the rise in popularity of meditation and wondering if I’m missing out on having a better life by meditating. The idea of meditation makes total sense to me. There’s science that’s proven its value. Adding more calmness and stillness to one’s life is absolutely something that I believe[…]

State of the Union 2017, and Preview of 2018

Another year, another handful of lessons learned! I’ve come to appreciate the value of reflecting on a year as a whole (in life and business) and then sharing my thoughts and findings. As a self-employed person, it’s very easy to get caught up in “the work.” Keeping your head down and trying to do ALL[…]

The Business Analytics That Actually Matter

When you run an online business, it can be very easy to get caught up wondering which business analytics actually matter. Is it your social media follower numbers? Your total website traffic each day/week/month? How much money you make every minute of every hour of every day? (Oh Google Analytics, I want to love you.[…]

What It’s Like to Sell a High-Value Product, A Two-Week Video Journal

If you’ve ever wanted to see behind the scenes on what goes into selling a high-value product, you are in the right place. I’d like to start this two-week video journal off with a huge disclaimer: These videos are meant to be a confessional of sorts. Very little editing or bells and whistles added. Why?[…]

Here’s an Easy Way to Decide Between Being a Specialist or Generalist

One of the toughest questions I’ve wrestled with during my time as an entrepreneur is: should I be a specialist and focus on one thing, or be a generalist and explore multiple interests? AKA: Specialize, or nah? You may be struggling with the same question. Trying to figure out what your “niche” is, or whether[…]

How To Become a Master at Finding The Best of Anything

Wayyyy back in my entrepreneurial journey (around 2006), I was a co-founder of a tiny design and development company. It was actually an amazing gig with two super-talented guys. We regularly met in person and shared random ideas and thoughts for things we could build that would get attention for our design and development services*.[…]

Writing Better Sales Copy, Are You Selling or Helping?

Whether you’re writing email pitches, website copy, newsletters, or any other form of writing that sells your product or service, sometimes it can feel like a painful slog. One small mindset shift has really helped me when it comes to writing sales-related things, and that is to change your thinking from: >> I’m writing this[…]

How We Spend Our Money and Different Ways To Invest Yours

While the title of this article might suggest I want to show you how to spend all your money, it’s really an article about the different ways to invest your hard-earned cash. Let’s talk about voting with your dollars, living a rich and full life, and understanding the fragility of being a human being*. *Sorry to[…]

Break Out of the 40-Hour Work Week, The Working To Live Framework

Do you constantly find yourself wishing you had more hours in the day? Do you feel like you have very little extra time to spend with family and friends? Are you running your own business, but feel like your business is actually running you? What if you stopped letting your business dictate your lifestyle, and[…]

Challenge All of the Assumptions, Especially Your Self-Limiting Ones

Whether you’re looking to succeed in business or make changes in your life, the first step is to challenge your assumptions. Our brains have this mystical, magical, and commanding power over us. We know this. We even acknowledge it. But it can be incredibly difficult to challenge our own thoughts. Phrases like “I don’t think[…]

How Will People Describe You When You Die?

Death on the Internet is a weird thing. Social media accounts, websites, articles—there are so many lasting reminders of a person’s existence these days. One hundred years ago when you died, your friends and family were left with only their memories of you and maybe a handful of physical reminders. Your off-the-cuff opinions and thoughts[…]

Everything You Need To Know From My Experience With SEO averages 350,000 visitors each year, and 64% are from organic search results in Google. This is what I’ve learned about SEO in that time. I have a caveat I’d like to start this article with: I’m not an SEO expert. I don’t do SEO for a living. Truthfully, thinking about SEO gives me a[…]

Finish Lines Don’t Move Toward You

Every finish line in life or business is something YOU have to move toward If I’m being honest with myself, I’ve put off important tasks too many times. The main reason is that the important tasks are often the difficult ones. And even worse than being difficult, these tasks don’t provide any immediate gratification or[…]

Competition is Good and How To Use It to Your Advantage

Shift how you look at competition in business from a negative to a positive Recently, I remembered a moment at the very beginning of IWearYourShirt. People often ask if I ever had an “a-ha” moment with that business. A moment when I clearly knew it was a good idea worth pursuing. In September 2008, there[…]

Why I Redesigned My Site for the Umpteenth Time

Every good thorough website redesign article starts with an origin story, right? How this website got bitten by a radioactive spider. How it kept its dark secret from its family and friends. And how, every night, this website would squeeze into homemade spandex and a mask, fighting the Google robots and Internet trolls for what[…]

What You Need To Know About Community Building For Your Online Business

Community building has been one of the most important things I’ve done for my online business. Call them friends, subscribers, tribe, or whatever noun is haute at the moment. A community is a group of people organized around your ideas. And it’s something you must have if you want to succeed as an entrepreneur. A[…]

Getting Things Done and Taking More Action

We live in this weird time when anyone can make anything from almost nothing But they (and you and me) have to take action to do it. And many people don’t. You’re reading this article because you want to be among those who do. I never set out to be an “action” person I wasn’t[…]

The Difference Between Getting Paid and Making Money

Making My First $13 I’d made well over $13 before 2008. In fact, I had a perfectly acceptable 9-5 job that paid me thousands of dollars per month (as many of you reading this probably do). But on one morning in 2008, I made $13 on my own. My own money that came from an[…]

Hearing No and Dealing With Rejection

Dealing with rejection is a necessary evil to achieving success I want you to imagine a number in your mind—a guess about how many times I’ve heard “no” to my ideas. Whether it was trying to convince companies to buy my t-shirt advertising space, place a bid to own my last name, sponsor a page in[…]

The Obstacle Is The Way

The most important book I’ve ever read is The Obstacle Is The Way Speaking in absolutes is one of my least favorite things. It’s something I try not to do in my own life, and it can cause me cringe-worthy feelings when other people do it. Here’s what I mean when I’m referring to speaking[…]

We’re All Selling Something, So Overcome The Fear of Selling

Selling is not reserved for “salespeople.” We are all salesmen and saleswomen. People who sell things come in all shapes, sizes, and varieties. You’ve probably purchased something from one of them in the past hour/day/week (without thinking you were buying from a salesman/woman). Every time you spend a dollar, it’s because someone convinced you that[…]

I’m Quitting Facebook

Dear Facebook, It’s time we took a break. We’ve been together for over 12 years. Kind of hard to believe, right? I remember when it was just you, me, “the wall,” a few silly pokes, and a couple friends sharing tidbits about our lives. It was innocent. You were trying to figure yourself out, and[…]

There’s Nothing Special About Today

There’s nothing special about today. There’s nothing special about this week. There’s nothing special about this month. It isn’t the start of a new year. It isn’t the perfect time when the stars align just right. There’s no magic in the air that’s going to help you. But you don’t need any of that, anyway.[…]

Are You On The Field or In The Stands?

Are you the type of person who should be building and creating? Unlike professional sports, owning your own business doesn’t require physical gifts. You don’t have to be freakishly tall to build a piece of software. You don’t have to be able to bench press a VW Bug to write a book. You don’t even[…]

How To Write Better and Overcome The Fear of Writing

3 years and 3,000,000 words later, I know how to help you write better You’re not a writer—Stephen King is a writer. You can’t write anything about marketing—Seth Godin has written it all. No one wants to read your opinions—everyone has their own opinions to sort through. You have no writing credentials. You didn’t go[…]

To Succeed In Business You Must Listen To Your Gut

On the path toward becoming successful in business, it’s easy to get off track and not listen to your gut It’s easy to let a shiny new idea or opportunity derail our progress. It’s human nature to let ourselves get pulled away from doing the actual work of getting where we want to go. Since[…]

Why Businesses Fail, Stories of People Not Showing Up

I’m constantly amazed at some people’s lack of ability to show up in business Some statistics say 9/10 new business owners fail within their first year. Others say it’s 75% failure within the first 6 months. A newer study says 50% of businesses make it five years. I used to believe that it was a[…]

The Gluten-Free Business Plan You Can Stick To

There is no perfect plan for anything, especially not our health or our businesses In 2016 I turned 34 years young. A completely unimportant and inconsequential birthday. But one thing slapped me in the face as I was getting ready to put on my party hat and bash my gluten-free cookie-filled piñata (I didn’t actually[…]

You Shouldn’t Do It

I love Nike’s slogan: Just do it. It’s a great motivator. There are lots of difficult things in life that you should do anyway. But for this article, I want to tell you why you shouldn’t do it. And what’s “it?” Starting and running your own business. You shouldn’t do it because it takes effort Are[…]

Do It Differently

Doing things the same way brings the same results, here’s why you should do it differently In 2013, it was measured* that there were 152 million blogs on the Internet. Google tells me there are 248 million results for the search term “portrait photographer.” A quick search on Amazon, and there are 50 million published[…]

Why You Should Focus on Enough Instead of More

There’s a culture of more going on right now. More money. More social media followers. More customers. More attention. More. More. More. As someone who’s fought to have more of everything in recent years, I’ve learned I don’t actually want more anymore. I want enough. I want enough money to live a comfortable life. I[…]

Why I Gave Up My Verified Status On Twitter

When almost anyone can get verified on Twitter, is it worth being a verified account anymore? One morning in August 2012, I woke to a very weird email. The email was from Twitter, and it was alerting me that my account had been granted “verified” status. I knew what verified accounts on Twitter were, but[…]

An Inside Look At The Tools I Use To Run My Business

Running an online business sounds a lot like sitting on a beach with nothing more than a laptop and sand between your toes. Except, if you’ve ever tried to actually use a laptop on a beach, the glare is awful, you have a terrible wifi connection, and you’re constantly worried about sand getting in your[…]

The Keys To A Successful Business Partnership

Business partnerships can create opportunities to work on bigger projects or try new things When deciding to collaborate with someone on a project or start a new business with a partner, there are a handful of important steps to take before moving forward. Having worked with multiple partners on multiple projects over the years, I[…]

Outsource Your Weaknesses To Run A Happier and Healthier Business

By confronting and outsourcing your weaknesses, you free up time for things you’re better at Wouldn’t you rather focus on doing things you’re happier doing? Things you are able to provide more value with? A few questions to think about: 1. What is the total time every day you spend on tasks you don’t enjoy and/or[…]

Define What Success Means To You Based On Your Art

The more you create, the more you’re able to create without over analyzing and putting pressure on yourself I finished a Skype call with a guy named Ash. We chatted about content creation and distribution (specifically writing, like these articles). In that call, Ash asked a simple question: “With the content you create, how do you define[…]

Find Your Flavor of Minimalism

One of the most profound changes I’ve made in my life has been becoming a minimalist I hope the word minimalist doesn’t turn you off, because I’d like to explain the benefits of minimalism and why I believe with every fiber of my being that you should try to find your own flavor of minimalism. Before[…]

Learn The 3×333 Method, or How To Get 1,000 Tasks Done

1,000 tasks?! Is that possible? That’ll take a lifetime, right? No way it could take a sensible amount of time to accomplish 1,000 tasks or to-do items, right? That’s what I used to think too. Enter the 3×333 Method. You want to get more done in your life and business, right? I mean, if you’re reading[…]

Put Down The Toothpick And Pick Up The Hammer

The story of The Statue of David and how it relates to worrying about the imperfections in your business. Imagine a giant block of Italian Carrara white marble. It’s over 20 feet tall, it weighs over 6 tons, and it’s your job to turn it into a beautiful statue. Imagine the pressure you feel: your reputation rests[…]

State of the Union 2015, and 2016 Preview

Inspired by my friend Paul Jarvis and the habit-building machine James Clear, I decided to write my own 2015 review and 2016 preview. My state of the union. Originally, I hesitated to write this article and realized why I was hesitating: I was afraid I might have to admit I’d failed, or that I’d find[…]

How To Fire Your Bad Clients and Bad Customers

In 2009, I ran into my first bad client. If you’re reading this article, I’m guessing you’ve had a bad client or customer too. While running my IWearYourShirt (IWYS) business, I encountered clients of all shapes and sizes, but up to that point (and a count of 161 previous clients) I’d never dealt with a[…]

Learn To See Beyond Boundaries

What if you didn’t do things the way everyone else did them? What if instead of walking the paths of other people, you created your own paths? What if boundaries actually became opportunities? During the recession of 2008, when companies were cutting back all spending, I decided it would be a good idea to ask[…]

See Behind The Scenes: How We Work and Travel

It’s taken us a few years of trial and error, but we’ve figured out how to run our businesses efficiently no matter where we are. The life of an entrepreneur is a funny thing. Some days you find yourself not being able to remember the last time you ate a meal or took a shower,[…]

The Ethical Guide to Building An Audience The Right Way

Over the years, I’ve tried building an audience using every tip, trick, and hack out there. I paid for fans on a Facebook Page (when that was a thing) and bought followers on Twitter (I was a big deal in Malaysia for 24hrs). I’ve even bribed people with giveaways of iPads, MacBooks, heck even cash![…]

Find Courage, Happiness, and Gratitude

What would you do if you completely froze on stage in front of hundreds of people? I decided to do that on purpose. I stood on the side of a stage, moments away from getting up in front of 200+ people. The woman who was speaking before me asked me: “what are you going to[…]

Understand That Feedback Is Dangerous

Feedback has a 10th degree black belt in the art of derailing progress. Be very careful with feedback. I’ve always been fascinated by the music industry. Not necessarily the labels, insane deals, and celebrity status but more the process of how a new album or song is created. See, for the most part, musicians create[…]

Avoid Burnout

In 2012 burnout hit me like an unsuspecting right hook from Floyd Mayweather. “You can’t sustain this.” “You need to take a break.” “Eventually, you will burnout.” Those were things that were told to me again and again in 2009 as I embarked on a business that operated 365 days out of the year. My[…]

Create More Opportunities By Turning Off Consumption Mode

By avoiding the process of creating and staying in consumption mode, you’re denying the world your gifts. Today is the day you admit you’re in consumption mode. Today is the day you flip the switch to creation mode. Today is the day you draw a line in the sand and say, “I’m done consuming!” We’ve[…]

How To Manage Time Better and Make More Money

Managing your time can be a pain, but if you figure out how to manage time better, you will make more money. Remember the fortune teller Ms. Cleo? She had a bunch of infomercials a decade or two ago and in a deep Jamaican accent would say “Call me now…” Well I’m putting on my[…]

Understand The Gap in Entrepreneurship that No One Wants to Publicize

Your level of success should be measured by your own values, not against Elon Musk’s plans to terraform another effin’ planet. Entrepreneurs are often glorified for their one big project that sells to a large company for an absurd amount of money. But for the vast majority of entrepreneurs, this is not actually the case.[…]

Why I Left Jacksonville

Jacksonville has way more to offer the world than just a football team and its physical size. Thanks for everything Jacksonville. I called Jacksonville home since August of 2000 when I moved down there to attend Jacksonville University. Before Jacksonville I lived in Arizona, California, Virginia, and New Jersey. Jacksonville is the city I’ve spent half my life[…]

22 Weird Things You Didn’t Know About Me

Let’s peel back a couple layers. I’m all about embracing my indifference these days. I no longer care about sharing the perfect article or the meticulously edited photo. Life isn’t perfect and neither am I. So let’s do it. Let’s give you a better understanding of who I (Jason Zook) am as a person. 22.[…]

My 25,000 Email Subscriber Mistake

Don’t build the wrong audience just because you want more subscribers. Build the right audience and focus on nurturing it. A few years ago, I put my first email signup form on a website (for my IWearYourShirt business). I had no clue what I was doing, but several people had told me I needed to[…]

How To Become Insanely Good at Getting Things Done with To-Do Lists

I want you to get better at completing tasks, managing multiple projects, and enjoying the feeling of accomplishment on a daily basis! To-do lists are essential to getting things done. Lots of people ask me how I juggle so many projects, businesses, and ideas at one time. The answer: I’m a to-do list aficionado. I[…]

You Are Not Average

You don’t have to stay on the path of average. You don’t have to let other people control your circumstances. I’m not average. I’m special. I’m different. It’s a really weird thing to type these next few words, but I teared up while writing those three previous short phrases. I don’t think I’ve ever actually[…]

Why I Don’t Believe In Luck

Luck has this amazing ability to show up after all the hard work has been put in, and often times, after someone has lost hope that their effort will pay off. For as long as I can remember, the saying, “you just got lucky” or “that person is so lucky” has always made me cringe.[…]

Think Reinvention — Not Resolutions

Resolutions are short-term fixes. And, unfortunately, they go uncompleted year after year. This cycle of incompletion dilutes the power of making resolutions, and leaves us buying into a broken system. We all do it. We write a list of resolutions and 99.9% of us fail miserably at sticking to them. Trust me, I’m as guilty as the next[…]

Do A Social Media Detox

Taking a social media detox for a month really opened my eyes to the feelings and motivations I have using Twitter, Facebook, etc. Here’s what living without social media for a month is like. Most people won’t admit how much social media means, or has meant, to them. For me, social media has been my life[…]

An Unexpected Lesson About Business and Life From LeBron James

This article will have nothing to do with how LeBron James plays basketball and I hope you can suspend your like or dislike of him and/or the sport of basketball for a few minutes. For those of you who aren’t familiar with the story of LeBron James, let me very quickly catch you up to speed: LeBron was[…]

You Don’t Get What You Don’t Ask For

90% of people are afraid to ask for things. Is that a real statistic? Nope. But I believe it to be a true statistic, if not higher than that. We, as humans, are afraid to ask for things. We’re afraid to ask people to buy our products. We’re afraid to ask someone out on a date. We’re[…]

How To Overcome Resistance, Self Doubt, and Fear

Recently I was on a call with a fellow entrepreneur and while discussing why they hadn’t put their new project out into the world the person said this to me (something I hear often): “But Jason, I’m not like you, I can’t just, you know, do stuff… Launch things all the time and take risks. It’s not[…]

See Behind The Scenes of How We Built Teachery

If this is the first you’re hearing about this, I’m sharing an unfiltered behind-the-scenes look at how I’m building my next online business. Get caught up on previous updates here: Part One, Part Two, Part Three, Part Four, and Part Five. What’s in a name anyway? Gerlando (my co-founder) and I never really loved the[…]

Surround Yourself With Good People By Building A Trust Circle

Building a trust circle is not difficult. These people are, most likely, already in your life and helping you. I stumbled into having a trust circle in 2012. I had built relationships with people through social media, through attending conferences, to wearing t-shirts for them, and felt a certain level of trust with them. When the idea for BuyMyLastName[…]

6 Ways To Boost Your Creative Thinking

Being able to think outside the box is a learnable skill. You just have to be willing to try new things. Many people think you’re either a creative person or you’re not. While I agree that some people may be slightly more predisposed to thinking creatively than others, I think creativity is a muscle that[…]

Learn From Weird Al Yankovic and the Anti-Marketing Mindset

You can’t just create whatever your art is and think strangers worldwide are going to stumble across it. You may have noticed Weird Al Yankovic made a roaring comeback. He released a new album and amassed over 20,000,000 views on YouTube in just three weeks in 2014. His album hit #1 on the Billboard Charts, the first[…]

The Opportunity Cost of Not Showing Up

You have the potential to lose so much more if you never take a chance. I left the “security” of the 9-5 world back in 2007. At that time I was three years out of college, had a good job (by other people’s standards), but found myself very unhappy. The people I worked with were fine. The work I[…]

Increase Creativity and Do Better Work By Taking Time Off

I can remember it clear as day. The first year of IWearYourShirt was coming to a (fun and profitable) end and people were emailing in to congratulate me on pulling off such a crazy idea. Besides the accolades, there was a message that got repeated over and over: “Jason, you did a great job with the first[…]

You Have an Idea For a Business or Project, Now What?

If you’re anything like me you have ideas all the time. Maybe your ideas come to you in the shower, while driving somewhere, while reading a book, or during some other activity. For many of us, it’s not coming up with an idea that’s the hard part, it’s what the heck to do next? Recently I got to[…]

How To Get an MBA in Entrepreneurship

A few years ago a friend told me he was taking an “Entrepreneurship Class” and I remember raising an eyebrow. How do you take a class to learn how to be a certain type of person? The word entrepreneur is defined as: a person who organizes and operates a business or businesses, taking on greater than[…]

Fear Doesn’t Have to Paralyze You

The crazy thing about fear is that we aren’t born with it. If there’s one thing I’ve learned about myself over the years, it’s that I’m not afraid to put myself and my ideas out there. For some of you reading this, you’re the complete opposite (and that’s okay!). The crazy thing about fear is that we aren’t born[…]

Which Social Media Platform is the Best?

This has to be the question I get asked most often about social media during interviews, speaking engagements, consulting calls, etc. “Which social media platform is the best?” When people previously asked me this question, my go-to answer was Twitter. It’s a completely open platform (meaning you can find and follow anyone) and it’s completely[…]

The Skill They Don’t Teach You In Any Business Class: Flexibility

Owning a business is not a smooth ride for most people, myself included. You set yourself on a certain path and a hurricane of changes completely derails you. You write down specific goals and they get shaken up by an earthquake of revisions. Being flexible is probably one of the most important skills you can[…]

Define Your Four Freedoms

Through owning my own business and having financial ups and downs over the past few years, my eyes have been spread WIDE open when it comes to money, success, and happiness. There’s this idea in our society that success is measured in fancy cars, big houses, expensive clothing, and luxurious vacations. I previously wrote about societal pressures and how they affected my[…]

How To Have A Successful Kickstarter Campaign

How Mizzen+Main raised over $25,000 on Kickstarter in the first few hours and how you can too. **Update: Mizzen+Main crushed their Kickstarter project and finished with $54,568 in funding (3x their goal!) If you’re looking for the perfect success story for how to dominate Kickstarter and get your project fully funded, look no further than[…]

Don’t Make These Email Marketing Mistakes

The email you see above is an actual email I received after test driving a car. I’ve blurred out the company and their contact information. The point of this post is not to call out the company involved, because they certainly aren’t the only company/people making these types of email marketing mistakes. Take a look[…]

You Won’t Hit a Home Run Every Time And That’s Okay

In the baseball game of life, we take many swings, and most of them don’t end up being home runs. Those swings might be in relationships. They might be in business. Heck, they might even be in games of actual baseball. But here’s the thing, you won’t hit a home run every time and that’s[…]

Interview with James White – Creativity Unleashed

I’ve been to my fair share of conferences and seen my fair share of public speakers, but I had never experienced anything like watching James White on stage. When I saw James speak at ConvergeFL last year I honestly think he had 200 slides in his presentation. And I could have seen an additional 200[…]

How To Deal With Haters and Negativity

Listen, if anyone has dealt with haters and negativity the past few years it’s me. I don’t think that’s an accomplishment many people want, but hey, if you’re not invoking emotions in people, you aren’t pushing the boundaries enough right? Wearing t-shirts for a living, selling my last name (twice), appearing on major media outlets,[…]

3 Huge Opportunities I’ve Said “No” To And Am Glad I Did

I’ve turned away multiple opportunities over the years and here are three that I’d like to share: #1 Turning down a promotion, new job title, and higher salary Before I was wearing t-shirts for a living, I had a handful of real jobs. My first “career” after college was working for a professional sports organization.[…]

A Look at my First Day with the Name Jason HeadsetsDotCom

And there you have it folks, my brand new last name for 2013: Jason HeadsetsDotCom. Technically I’m not changing it until January 1, 2013, but let’s be honest, I’m terrible at waiting for things. I thought it might be fun to take you guys along with me through the craziness that was my first day[…]

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