Why I Went from Selling a Software Company to Selling T-Shirts

By Ben Weiss
May 4, 2022
Why I Went from Selling a Software Company to Selling T-Shirts

The Mark Zuckerbergs and Evan Spiegels of the world have shown how software businesses can be a fast track to fame and fortune. With a good idea, hard work, and skillful execution, you too can go from rags-to-riches (or, in their cases, riches-to-filthy-riches) and own a Hawaiian island or marry a supermodel.

I too created a software company out of my dorm room. And while it didn’t achieve near Zuckerberg or Spiegel levels of success (they run multi-billion dollar companies; I live in a studio apartment), my seven year tenure nonetheless resulted in an acquisition that bought me a couple of years of financial freedom.

While the positives of running a software company are clear as day, there are marked drawbacks to the gig that often get overlooked. Yet it’s because of these drawbacks that I’d rather create a t-shirt brand than a software business at this stage of my life.

Drawbacks to Creating a Software Company

My previous business sold software for up to $15,000 a year to help college football programs find recruits. But creating software worth that price point required a significant investment of time and money…with no guarantees of a return. We brought on several software engineers to create the product. And once we had something to sell, we then had to maintain and improve the product and hire folks to help with sales, support, and renewals. There was a daunting price tag and time lag required before we finally broke a profit.

Running a software company was an all-consuming endeavor. There was always more that I felt like I could or should be doing to grow the business. And when I wasn’t working on the business, I was thinking about the business. I had to be present in case an urgent product issue popped up on a weekend. And if a prospective customer called at 10pm, I was answering then and there.

And starting a software business requires long-term commitment. As soon as we had paying customers that counted on our software, we had an obligation to provide a level of product quality and service in perpetuity…or else we’d let our users down and violate their trust.

After wrapping up an emotionally draining seven-year-long project, I’m not quite ready to commit to a new, expensive, all-consuming venture with an infinite time horizon. But I still have a desire to create. I want to get my creative juices flowing and work on something that fills me with joy, passion, and excitement.

I’ve been able to find that by creating a t-shirt brand – while avoiding those software company drawbacks.

The Beauty of a T-Shirt Brand

A while back, a friend posted a picture wearing a shirt with an upside-down pocket with a graphic of a cat appearing to fall out. I loved the idea of the shirt…but being more of a dog person, I set out to find a non-feline version that I could sport. My search results for ‘upside-down pocket tee’, however, didn’t reveal many alternatives.

Over the next few days, I found myself swimming in ideas of graphics that I would love to see spill out from the upside-down pocket of a tee. By the time the list on my phone had reached scrolling length, I felt drawn toward bringing the idea to life.

The path from ideation to creation was relatively quick and inexpensive. It took a few weeks and a few thousand dollars to have the product designed and an order of 300 manufactured and delivered. And, my financial downside on the batch is largely capped while the upside is both projectable and appealing.

A t-shirt brand also gives me more flexibility over my time and ambitions. I can spend five hours or sixty hours a week on it. It can stay a one-man operation, or I can bring folks on to scale it up. Sure, the outcome will vary based on the amount of time I invest or number of people involved. But I can thoughtfully choose my commitment level and make the business as big or as small as I’d like.

And while software has continuous use, t-shirts are a one-off transaction. With this t-shirt business, I can quit at any time without letting people down. I have no perpetual obligation to customers.

It’s Simply the Right Time for Me to Sell Some Tees

Is a t-shirt brand inherently a better business to start than a software company? No, it’s certainly not. T-shirts are a commodity. There’s a lot less upside to selling graphic tees than in creating transformative software. And I’m sure I’ll encounter a host of unexpected frustrations while dealing with the physical world of manufacturing and shipping, and with getting eyeballs on the product via digital marketing.

But these are challenges that I’d rather take on at the moment.

There will likely be a time in life when I’ll feel ready to sign up for that next all-consuming seven-to-ten year commitment. When I’ll have enough conviction around a moonshot idea to plunge significant time and money towards it.

But for the time being, I feel comfort in knowing that I can pursue something that interests me in the moment without fearing the trappings of its potential success.

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