I’ve been very lucky in my career to start numerous businesses that have been successful. Building, running, and growing these businesses has been an emotional roller coaster to say the least. The experience though is a never ending learning process, not just in business, but in how I look at life.

1. In my career, I needed to control my own destiny

While I had entrepreneurial aspirations, out of college, my parents pushed me to get a job. I had started an educational website called EasyBib, which automated citations for students. I thought I could grow it into a larger business, but parents wanted me to get real world experience.

My first job out of college was on Wall Street. I never really wanted to be there. As an investment banking analyst, you often do a lot of mundane work from formatting powerpoints to making photos copies.

I wanted more meaning to my work, and to be in control of how I made money. Doing this kind of work, while it paid well and offered a good career path, felt like I was wasting important time. This never became more clear when I had my first year-end review where I scored lower than all my peers.

At that point I realized I didn’t want others dictating my success. I needed to be in the driver’s seat. I left a few months later at the age of 23 to work on my education business and see if I had the chops to make money on my own.

2. I didn’t enjoy learning in college, but I love learning on the job

I majored in economics, and if you asked me to teach a high school class on it today, I would struggle for words. Much of what I learned in college, I don’t remember today.

In fact, my real education came on the job. I learned the basics of finance during my short stint as an investment banker, but my best education has been the constant trial and error of trying to grow a business. You make so many mistakes along the way that they turn into experiential life long lessons.

While I never enjoyed learning in college, I enjoy learning on the job. It’s a real world environment where you can hypothesize, test, and learn constantly. I find myself more curious than ever, and the emotions of failing and succeeding ensure learnings are never forgotten.

While I can’t remember what’s in the textbook from college, all the long 50-page papers in undergrad prepared me with critical thinking skills. You had to learn to communicate and understand different viewpoints. These intangibles have been invaluable for thinking through and solving challenges growing a business.

3. Opportunities happen when you’re not looking for them

When we started our first business, EasyBIb, we were just high school students. We weren’t trying to be entrepreneurs. As students, we thought bibliographies were tedious. When we were assigned a paper that required 10 citations, the lightbulb went off that we could automate that process with software.

After we sold EasyBib, I stayed with our acquiring company Chegg to ensure a smooth transition. After I left Chegg though, I was stuck in a rut. I had spent most of my career building out EasyBib and other educational products, and I had no idea what to do next.

As I was researching new opportunities, I would find myself playing solitaire online. It was challenging and relaxing at the same time. Moreover, it would help clear my mind.

That’s when the lightbulb went off to start my new venture Solitaired. What if we can tie classic games like solitaire to brain training? I haven’t looked back since, and now thousands of people come to the site every day.

4. You can create your own luck

I often think that I’m a lucky person. For instance, we had the lucky break of the Chicago Tribune covering EasyBib when we were high school teenagers, which super charged the growth of the site. We also managed over time to acquire all our competitors in the space over a period of six years.

I think there is an element of luck with our success, but I’ve realized that I often put myself in a position to be lucky.

When we got covered in the Chicago Tribune at a young age, I emailed every newspaper I could possibly think of. I ended up getting in touch with the right person at the right time at the Chicago Tribune, but it would have never happened if I didn’t reach out.

With our competitors, I forged constructive relationships with them over years. Eventually, once a level of trust had been built, they decided to sell to us. I didn’t pick up the phone and simply get lucky.

This has taught me to always put myself out there to see what happens. Luck doesn’t come to you, but you can try to find it.

5. I want my kids to be entrepreneurial

I can write a book with all the mistakes and failures I’ve had over the years. But these setbacks were really a reflection of putting my best foot forward, trying, and then trying again.

I’ve learned nothing comes easy, but with grit and a positive attitude, you can learn to solve many problems. Your worst case scenario: you have valuable learnings.

While I don’t care if my kids want to run a business one day, I want them to be entrepreneurial in spirit. I want them to learn to solve problems and get back up when they fall. I want them to understand that failure should be celebrated and it’s actually just a learning moment. Those traits will help them in anything they pursue from their personal life to career.

A forever evolving outlook

By putting myself out there with my business endeavors, I’ve continued to learn every day, and with that I’m certain my outlook on life will continue to evolve.

Neal Taparia founded Imagine Easy Solutions, an educational software business, which reached over 30 million students annually. After selling the business to Chegg and serving as an executive with the company, he started SOTA Partners, which invests in the future of education and food, and co-founded Solitaired, which connects classic games to brain training.




Image courtesy of Taryn Elliott.