May 10, 2019

Successfully Failing: What I Learned From Failing My First Startup

Tom Nassr
CEO & Co-Founder
“Experience is what you get when you didn’t get what you wanted.” — Randy Pausch

Most startups fail.

This is a well-documented fact, and it’s probably not news to you.

Of course, statistics can be misleading, and you’re probably better off not just thinking about yourself as another set of data on a predetermined path.

But the reality is that most startup founders must confront failure at some point, no matter how well they’ve prepared or how hard they work. I know I certainly have.

The first time I faced failure as a founder was with a company called Qustir that I started in my freshman year of college with some classmates. It was a digital coupon app, made before RetailMeNot burst out on that scene. The idea was to generate a barcode on your smartphone that, when scanned at a cash register, would automatically apply discounts already available in the Sunday newspaper. Millennials don’t cut coupons, or even read newspapers, so why not give them a way to enjoy the discounts that companies are already offering? That was the essence of our idea.

The name came about as a portmanteau of “coupon” (spelling changed to ‘Qu’ for maximum trendiness) and “stir” (because we were ‘stirring up the pot’). We thought we were being clever, but it turned out that it was just difficult and confusing for people to read.

Branding issues aside, Qustir’s early days were actually pretty promising. We competed in the CT New Venture Competition, won some money, and thought that it was only a matter of time before we revolutionized the coupon industry. Between the sheer amount of time and money wasted on transporting coupons, the reception cycle between retailers, suppliers, distributors, wholesalers, and coupon collection facilities, the industry looked ripe for disruption.

Having no technical skill whatsoever, and being completely unaware of the tools real UX/UI designers use, I defaulted to Keynote to make screen mockups. I figured that if I made screen mockups, I could raise money, hire a developer from China, and have it in the app store by the end of my Sophomore year of college. That couldn’t be farther from what actually happened.

Though we had the screens, we didn’t have a clearly-defined user base, we didn’t know how the coupons would be added to the app, and we didn’t have the technical knowledge to build it. It turned out that raising money for an idea that had no traction, no validation, a vaguely-defined market, and a weak business model is harder than we’d thought, especially in Connecticut.

An enormous amount of my time (probably 6 months or more) was wasted with “perfecting” a pitch and pushing pixels making screen mockups. By the end of my sophomore year, my two business partners were about to graduate, and Qustir wasn’t something I really wanted to invest more time in. I thought it was a great business opportunity, but it just wasn’t a good fit and we never did the necessary groundwork to make it succeed. After all, I was a 21 year old trying to run a business that revolved around coupons, but I actually barely went shopping.

After I ended Qustir, packed up shop, let the domain expire, and plopped the files into an “Archived” folder, I tried to move past the experience and push it out of my mind. The partners of the company split up on less-than-ideal terms, which was a hard thing for me to grapple with and understand. A deep sense of suboptimal execution on my end left me feeling anxious and like I wasted time, money, and energy. I tried to kill the memories, and hide the failure from myself as much as possible. Someone asking about Qustir would put a damper on my whole day. It was not a healthy way to deal with the process.

Eventually, I developed a different perspective on what I had accomplished. Starting my current company, a digital agency called Checkmate Creations, made me rethink the experience that I had previously defined as a complete failure. That was when I started to leverage old contacts, reconnect, self-analyze and start understanding that I don’t understand everything. That was when I realized that I had built something with a lasting impact with Qustir, even though it wasn’t a financially successful venture.

What I realized was that I had gotten a lot out of Qustir in the end. For one thing, it was a great excuse to meet and talk to people. I’m not sure if it was the quality of the idea, or my relentlessness in reaching out to make connections, but people took my meeting. Once I was in the door, I just told my story. I tried to answer the question “how did you get here?”. It turned the conversation into something more personal, rather than a banal transactional meeting about coupons. In the process, I built a solid network, and gained invaluable practice in the art of the pitch. Lessons like these outlast any single startup.

Given these gains, it made me reconsider my concept of “failure” in entrepreneurship. Yes, in a technical sense, Qustir failed as a business. It never made money or gained a user. But did I personally fail if I learned something from the experience? Over time, I’ve come to think of the end of a startup in terms of failures and successful failures.

A failed startup is a failure of the entrepreneur to extract useful resources, assets, or knowledge outside of the lifespan of the startup.

A successfully failed startup is what happens when the entrepreneur can up-cycle the time already spent on the failed startup into their next venture, in any way possible.

I was able to up-cycle the small but engaged network I gained through Qustir. For my personal development, I had pitch practice, including the experience of pitching in front of hundreds of people. That’s not something that most people have an opportunity to do. After all, if I could confidently pitch a business that was a total failure in front of hundreds of people, I could only imagine pitching a business that actually delivered value. That’s what I find really exciting now. With Qustir, I thought I could deliver dollars. Now I know I can deliver value.

Up-cycling your past experiences doesn’t just apply to the business world. Any difficult situation can be up-cycled into an opportunity for value; it’s just up to you to be aware of your experiences as they happen, and to analyze them carefully after the fact. Then, you can apply what you learn to further your personal growth, improve your confidence, and continue the pursuit of your passion.

The key is patience. Entrepreneurship is a long, long game. Your “prime” probably isn’t at 25. It’s likely going to be closer to 55, or 65, or 85. Failing at your first hurdles might feel like crap now, but with the right attitude, those scrapes and bruises can teach you what you need to know to get back up and clear the next ones.


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