Me with partner in 2008 somewhere in Brooklyn

My first business was a complete failure

Featured pic above by Billy, I think, of my business partner and me at our first photo shoot. We had no idea what we were doing. What is that look on my face?

Grand dreams of selling luxury t-shirts swirled in my mind, as I schlepped through Bedford Stuyvesant, the Brooklyn neighborhood in which Jay-Z grew up. It was 2008, and the Great Recession had begun.

I was walking through those streets to get my luxury bamboo shirts manufactured. I was there to build my dream from nothing once stitch at a time.

And I was ready to become the next t-shirt mogul.

It all started with an idea. I thought the world needed environmentally sustainable t-shirts with an artistic flare. It was probably beyond my reach, but I wanted to try.

Someone else did, too. One of my artist friends joined me. We became partners. He designed the shirts, and I handled the business.

But the economy was plummeting into an abyss, and people were scared that this was the end of the world as we knew it. And somehow, bamboo t-shirts from a brand they had never heard of, no matter how beautiful, weren’t of interest to them.

My partner decided to back out, while I forged ahead into 2009, as the stock market got even bloodier. I was determined to make this business work.

I pushed myself beyond what I thought I was willing to do. One of my goals was to get our product into various high-quality stores that sold other casual luxury brands.

I cold called and emailed these stores to see if they would consider my shirts. If that failed, I just showed up unannounced like some feral cat looking for food at their doorstep. Except I didn’t want a meal, I wanted their manager. It felt so invasive and desperate, but I did it anyway.

I had to go all the way. I wanted to know that I exhausted every legal option I could to make this business work. I didn’t want to sell my soul to make a sale, but I was willing to forgo my pride and dignity.

I also sold the shirts online and begged my friends to buy them. And, many of them did (if you did, thank you! I owe you.). I was astonished. I fulfilled the orders in my bedroom, carefully folding the shirts and packaged them for shipping. I was CEO and mailroom boy in my corner office/bedroom.

I came close to selling to a couple of stores, but they all eventually said “No.” And some of them ended up folding in late 2009.

And, as you read in this post’s title, my business failed, too. I failed.

But, I did walk away with an invaluable experience. I was closing myself to this effort and work but not the lessons I learned. There were many.

I’ll share some.

Failing didn’t kill me.
This venture forced me to put myself out there. I pushed it online to my friends. I cold-called and even went door to door, peddling my goods and was rejected over and over. But, I survived. In fact, I felt even better than I had in many years. I felt alive, even in the face of failure. The experience had awakened me somehow. And, I knew that I wasn’t the same anymore.

The truth is, starting a luxury t-shirt line was a stupid idea in 2008. The timing was so off it’s silly. But, for me, it was still worth trying. I will remember the experiences of getting my friends together to do a photoshoot and directing them. Did I know what I was doing? No! But I was just doing it, going for it. That was an incredible memory that has fueled ventures I had later in life.

Here’s one of the shots from the shoot. Thank you, friends!

Work was fun.
Work became fun for me for one of the first times in my life. Most of my jobs were just about me earning a paycheck. There’s nothing wrong with that, but doing work that I also enjoyed was a new experience. It was refreshing.

It’s true that I didn’t earn any money from it, but I was able to spend time with friends and create something out of a mere idea. And, I never wanted to decouple work from fun again.

Pushing myself out of my comfort zone was critical.
I never thought I would go door to door trying to sell t-shirts. Never. But, I asked myself, “Why not? What’s the worst that can happen?” The answer was simple. They could laugh at me and say, “No.” But, to chase a dream, that was worth potential ridicule and feeling shame.

It wasn’t dignifying work. But, when I thought about my dignity as a reason not to try, I realized that I was using that as a means to cover up my fear. I wasn’t really concerned about my dignity; I was just scared of embarrassing myself in front of strangers.

Getting over that hump helped me develop a muscle that I continue to use to this day. Getting my mind around something that makes me uncomfortable and overcoming it has been one of the most valuable lessons that I continue to employ.

As my dreams of becoming a t-shirt mogul vanished, another company I started, a website development agency, was taking off. And many of the lessons I learned from my failure, helped me make the second company a success.

I needed those lessons to equip me for my next venture. You see, failure need not be the end. And for me, it wasn’t. It became a new beginning, a transformation of sorts.

Failure shouldn’t define you. And, if you listen, it teaches you how to succeed.

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