In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that
have shaped their business philosophy.

Founder and CEO, Varsity Tutors


Varsity Tutors is an online learning platform that connects students and professionals with tutors who provide live, personalized instruction. Users have accessed more than 1 million hours of live instruction on the platform. The St. Louis-based company also offers free online learning tools including diagnostic tests, practice exams, flashcards and questions of the day in more than 200 subjects.

The Mistake:

Not devoting myself full time to my business earlier on.

When I started Varsity Tutors, I was a college student. After graduation, I went to work in investment banking, then in venture capital. So I worked four years full time while running Varsity Tutors on nights and weekends. I was putting in 10, 20, 30 hours a week and I waited for a long time to quit my day job out of concern over making the leap.

Eventually, I made the plunge. Then, I realized how many more things needed to improve. I wasn’t aware of them because I was running Varsity Tutors only a handful of hours a day and leaving a lot to my staff. I wasn’t conscious of all the different levers I could pull to grow the business. I really wish I had given it my full attention much, much earlier on and believed in myself to a greater extent and just quit my job.

From my perspective, if I had done so, we would have grown much faster. A lot of issues had to do with the technology. Because I wasn’t devoting my full attention to it, I didn’t have a good appreciation for all the problems customers and tutors were experiencing.

As a result of really immersing myself in the business after quitting my other job, I realized all the changes we had to make to the technological infrastructure to ensure we could do a better job and keep our customers and tutors happy. When we fixed these issues and invested in a system and platform that made our users happy, the net result was a substantially better growth rate because people were more likely to reward us with their business.

In my heart of hearts, I wanted to be an entrepreneur.

The Lesson:

Now, as a company, when we have an important problem that needs to be solved, we have people totally devoted to that problem. For example, when we’re designing a product, we have a leader who is designated with building a solution because, when everyone is responsible, no one is responsible.

Personally, when an opportunity presents itself, I put far more energy into understanding the opportunity and risks than I did in the past. And my overall risk tolerance has gone up considerably because I have a better understanding of how to solve problems. To a large extent, I believe in myself and I believe in the analytical process as a way to mitigate risks. Early on, despite all the data I had that the business was going well, I didn’t really believe in my own abilities. As I developed better analytical powers, it’s kind of made me believe in data and analysis as a way to prove out different strategies.

Part of my hesitation was the fact I had a really good job that paid well where I got to do cool work. I knew it was a hard job to get and felt bad about the idea of giving it up, despite the fact that, in my heart of hearts, I wanted to be an entrepreneur. You’ll always do a better job when you’re focused on something you’re passionate about than on something you’re not, and I was much more passionate about being an entrepreneur than I was being an investor.

The real learning was that, if you don’t give something 100 percent, you’re going to get a markedly different outcome than if you wade into the water. If you give something your full attention and dedication and brain power, you’re going to get a dramatically better result.

Chuck Cohn is on Twitter at @ChuckCohn and Varsity Tutors is at @varsitytutors.

Photo courtesy of Varsity Tutors.

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