How (not) to launch a t-shirt company

I launched a t-shirt company when I was 23 after recently graduating college. Prior to this point I had been making good money playing online poker. The government had just officially illegalized online gambling and the idea of getting a real job was so devastating, I had no other choice than to follow through.

It’s somewhat mind blowing how little information was available in 2006 to launch a physical products brand.

Back in 2006, Alibaba was not yet a thing (that I knew about anyway) and there were few resources online for discovering how to manufacture private label products but screen printers were fairly ubiquitous. There were also far less design resources than there are today so I hacked a logo together in photoshop and got ~200 t-shirts printed in 4 colors and various sizes.

Additionally, there was no easy way to accept credit cards in a respectable way. Sure, you could punch a user out to Paypal and have them pay there but it was an awful customer experience. I’d estimate it would take 15 clicks across 3 different windows, each that could not be branded and possibly at the end of that journey the customer would end up on a non-branded thank you page.

So I finally found a crude shopping cart that allowed me to quasi brand the pages and presented a fairly seamless experience for the end customer.

And I launched.

This was my first introduction to the idea that Field of Dreams was a lie.

If you build it, nobody comes.

This is one of those lessons that sticks with me today and I always laugh when people share their hot new idea with me and think that the only thing they need to do is get the app developed or product created.

Far more important than the product itself in the early days is driving traffic.

Somehow, some way a kid found my site within the first month but wanted to pay via check as opposed to credit card. To make up for my crappy designs, I thought the selling point of the shirts would be that I would donate 10% of profits to charity.

This apparently resonated with my first customer who wanted to purchase the shirts for a church retreat. He “bought” 10 shirts and had a tight deadline to receive them prior to the retreat.

I received his check in the mail and shipped them out immediately to meet my new customer’s tight timeline after wrapping them in black tissue paper to make the unboxing experience cooler.

Back in those days (maybe still, who uses checks?) checks took about a week to clear after depositing. Everyone knows where this is going but a week after shipping out my first order, I learned that my first deposit to my fancy new business checking account bounced.

I reached back out to the customer but he was a ghost. Had I really been desperate for the $150 bucks I could have probably tracked him down with the info I had but I just let it go.

Fairly quickly, I realized this wasn’t going to be a get rich quick scheme and with my high rent apartment that I locked into back when poker profits were good, I needed to get a real job.

I got super lucky and found a tech startup and fell in love with the team and the industry and the t-shirt company died shortly after.