How Selling T-Shirts and Furniture Taught Me to Be a Successful Tech Entrepreneur

The first career goal I ever had was to work in finance after graduating from college. However, I was still in high school when I got my first taste of entrepreneurship, and it left a strong impression.

In my senior year, a few friends and I started a small operation selling T-shirts and other school-related paraphernalia. Other students loved what we made, and we had a blast for a few weeks, raking in a small fortune (a few thousand dollars) before the school administration shut us down.

It was fun at the time, but I didn’t think it was life-changing. I still wanted to work in finance — but I graduated in 2008, when the financial crisis hit. All the firms I was interested in had either shut down or were bleeding employees and in no position to hire.

Focused entrepreneur working on his startup

I needed a job, so I chose an entry-level sales role with an office furniture company — not the sexy job I was aiming for. I was the low man on the totem pole, yet before long, I learned a great deal about finding clients, negotiating deals, managing teams, completing projects, dealing with manufacturers, and many other necessities required to run a business.

It gave me the confidence that I could start my own business, which I realized I had wanted to do since selling T-shirts in high school. Then, I had an idea for a hybrid travel agency and booking platform, something similar to TripAdvisor, which was very different at the time. For months, I stayed up at night researching every corner of the industry and planning the ways my company would be better than the rest.

I had saved enough money to explore the opportunity, so with no backup plan, I quit my sales job to diligently pursue my idea. After creating a business plan and the strategy behind my unique offering, I felt I was ready to start making partnerships with hotels and airlines to kick things off. However, during that process, I quickly learned that there were some flaws in my model and that I had not considered the legal restrictions in that industry. Ultimately, I didn’t pursue the business any further, but I did learn from the experience.

Lessons I Learned the Hard Way

As I pursued my travel agency idea, I learned two very valuable lessons. First, I discovered that I was truly passionate about the process of building a business — figuring out how to get it started and dreaming about how to make it grow. Second, I learned the importance of market validation and that without a viable product and a market that wants it, a business will fail. I was lucky to learn that second lesson without wasting too much time or money.

These lessons stacked on those I learned starting in high school. My pseudo-business selling T-shirts was the first time I learned about product-market fit. My time selling office furniture showed me that most companies, regardless of market, operate similarly. And fully pursuing entrepreneurship helped me tie it all together.

Clothing designer and maker

If you, too, have a passion for entrepreneurship, use the following steps to help you pursue it and stay dedicated throughout the process:

1. Stoke Your Passion

A recent survey by recruitment firms Accounting Principals and Ajilon found that 80 percent of workers in full-time positions are either open to or looking for new jobs. Part of the reason so many people aren’t tied to their current positions could be a lack of passion. And in my experience, a lack of passion is a big reason that many people choose the entrepreneurial path. You can explore a lot of ideas and get excited about some for a few days. The only ones worth pursuing, though, are those you see yourself happily running for the next five to 10 years.

Choose the idea that keeps you up at night with excitement, the one you can’t wait to tell people about, even when you aren’t trying to build a business around it. You’ll enjoy creating your business more that way, and you’ll avoid becoming stagnant from being stuck with an idea you no longer love.

2. Flesh the Idea Out

It’s important to follow your passion, but don’t do so blindly. Spend a lot of time researching your idea before investing in it. I saved a ton of money, time, and credibility because I realized early that my travel agency idea wouldn’t work. Do your research and find your product-market fit, or you might be doomed before you even get started.

Market research includes everything from reading industry association publications, online searches, understanding relevant federal and state commerce laws, understanding the market’s unique demographics, and most importantly, speaking to others in the industry or your specific target market to learn from them. Doing this market research is the only way to accurately gauge your idea’s potential for success and whether it’s worth the effort.

3. Become Your Business

Research documents, business plans, and spreadsheets will help you flesh out your idea, but once you decide to run with it, accept that you will become your business. It won’t be summer camp; you’ll need to commit to its long-term success, reputation, and sustainability. If you aren’t prepared to commit five-plus years of your life building this company, turn back now!

If you are committed, then realize that a successful company requires more than just having a sound, well-researched idea. Your company will likely consist of a team of people, and your company’s identity will include the principles and values you and your team adhere to. Your people need to unify and embody everything your company stands for — from conducting business in good faith and operating well as a team to negotiating successfully and providing excellent customer service.

Software development team working on a project

Putting It All Together

Fast-forward a few years from my first entrepreneurial experience, and I’ve now built several successful companies. With each new endeavor, I realize how much I still have to learn.

The greatest lesson any of us can understand is that experience is the best teacher. If you’ve never started a business, I strongly advise working for at least one well-respected company first. Learn from the company and the people around you: what to do, what not to do, how to handle difficult situations. You’ll learn a ton, and best of all, you’ll be getting paid for this education. Then, start plotting your next move before pouring all of your energy into your passion.