Recently I had a great conversation with one of my readers who found me through my contact form. His name is Sam Smith, a senior in high school who started his own T-shirt business using a company called CafePress. I told Sam that he is wise beyond his years to be thinking about financial freedom at such a young age.

This conversation brought back a lot of memories for me, because when I was his age, I was in the T-shirt business as well. Talking with Sam helped me realize how far technology has come in the last ten years, giving a young entrepreneur like Sam opportunities that were far beyond my imagination when I was in his shoes.

In the Old Days…

Back in the 90’s, when I was a senior in high school, a good friend named Chad Kalal and his coach started selling T-shirts for their soccer team. They were so successful, they started JOXX: a business that eventually included five retail stores and over 300 wholesale accounts from all over the country.

I was so interested in entrepreneurship that I volunteered to design shirts for free in exchange for learning about how their business worked (funny, my film career started the same way), and the knowledge I gained was priceless.

My unpaid design job turned into a paid job when I produced their first color catalog, and I eventually ended up as their director of marketing. (Click here to see a portfolio of some of the catalogs I produced for the company. See if you can find me in the pictures! (hint: I appear three times!))

After JOXX, I started my own T-shirt company by designing shirts for college groups while attending the University of Nebraska-Lincoln. (Click here to see a portfolio including some of my designs.) That gig kept me busy, but helped me pay for college.

I left the T-shirt business after college since back then it was very labor intensive. Designing the shirts was just the beginning. To get them sold, we paid thousands of dollars for color catalogs, mailing campaigns, and trade shows. T-shirts had to be ordered in minimum quantities of several dozen, which cost more money. Once we found someone to buy them, we had to pack and ship the shirts as well as provide customer service for the customers.

This kind of work is WAY more responsibility than an 18 year old should have! Kids in high school and college should be enjoying some of the best days of their lives while they still can, not spending all-nighters trying to meet deadlines and taking out huge loans to start businesses.


Today, young designers like Sam have an opportunity to do something that I didn’t: they have the ability to start a T-shirt business AND enjoy life at the same time.

After all the blood, sweat, and tears Chad and I lost in the ’90’s, I have to say that I am dumbfounded at the services that CafePress offers entrepreneurs. You see, the problem with creative types is that they love the creative process of starting a business and therefore excel at it; but they hate the mundane mechanics of actually running a business and sometimes fail because of it.

CafePress takes care of all the boring stuff so you can just concentrate on being creative. Sam explains it like this:

CafePress is a great site, meant for those with the creativity and drive to provide the designs and marketing for an online store while the CafePress warehouse takes care of any stock, printing, shipping, and billing. For a Photoshop junkie like myself, it’s a real jackpot.

Basically, you just submit your designs to your own store on their website (kind of like an eBay store. CafePress sets the wholesale price of your shirts while allowing you to set the price and profit margin. They take care of the mind-numbing business stuff like taking orders, packing, and shipping. You take care of the fun stuff like design and marketing.

CafePress offers two kinds of stores to its users: free stores and premium stores. I started out running a free store for a few months before I realized its limitations. Free stores have a limited selection of products, only allow one design per product, don’t allow custom HTML or CSS. I realized that with all the ideas I had, establishing a bazillion free stores (each with a different URL) was a bad idea.

So I decided to take the plunge and invest in a premium store. I pay $6.95/month to have the ability to upload as many designs as I want, customize my store (as well as advertise with other sites), and really create a good environment for visitors.

Possibly the best feature of Premium stores is that they give “blanket” controls for the owner that allow store/section-wide changes to price, printing method, description changes, etc. This makes the process of setting up a new section very efficient.

What’s remarkable is CafePress’s ability to print one shirt at a time, eliminating the risk they take on your designs. Back when you had to buy screen-printed shirts by the truckload, you had to make damn sure you had a great design before you printed 500 of them. Now, you can put a bunch of designs up at your CafePress store, keep the ones that sell, and ditch the ones that don’t.

Another added benefit is that the customer gets to choose their own shirt color, which would have been impossible back in the day. People love to customize, and CafePress gives you this ability without any added effort on your part.

My favorite thing about CafePress is that it requires no initial investment. I can’t stress enough how important it is to stay out of debt when you start a business. If you can create income streams with little or no initial investment, you take out all the risk.

Passive Income

Those of you that read this blog know that my thing is finding sources of passive income to develop the time freedom needed to pursue creative endeavors.

You see, back in my T-shirt days, I used to think that the key to wealth was starting a business. I quickly realized that wealth without time is worthless. In college, my business took up so much of my time that I could barely enjoy myself.

Now, I look for income streams that are extremely low maintenance, or passive, even if they generate less money than actually owning a business. If your income streams don’t require you to be there, the number of streams you have is not limited to the amount of hours in your week.

Although I have not yet tried CafePress, my suspicion is that it fits along these lines. It doesn’t seem like a million dollar income stream (because you don’t have the same control over your products that you would have in your own business), but it does seem like a passive stream. Once you have designed your shirts and set up your marketing system, you could walk away forever and still collect an income stream as long as your designs were in fashion.

What college kid wouldn’t want an extra few hundred bucks month after month for a few week’s work? Who knows, if your designs are good enough, and they take off, maybe you could earn a few thousand. The fact that you don’t have to be there to ship and field customer complaints makes this worth doing.

Check out Sam Smith’s CafePress store by clicking this link to reward him for helping me with this post.