Hindsight is a powerful thing—especially when you can use it going forward. Business owners learn many important lessons when looking back at the mistakes or oversights they made when starting their companies.


We asked entrepreneurs the top lesson they learned while starting their business. Here’s how they responded:


Be willing to change your product based on customer feedback.

When I began my college and career guidance company, we sold workshops to schools and organizations. It turned out that no one wanted to buy workshops from an outside consultant, and for one year, we did badly because we tried to force a product people didn’t want to buy. Eventually, we went into consulting students and families directly and grew the business significantly. I learned that it’s extremely important to iterate your product based on customer feedback.

Jason Patel, founder, Transizion, Washington, D.C.


Take risks—strategically.

I’ve learned many lessons over the years, but one that stands out is the importance of risk-taking. Some of our greatest successes came from taking risks that competitors hadn’t taken yet. For example, years ago, when we were still a 10-member team, we were one of the first companies to launch an online purchasing system for travel insurance. Prior to that, customers submitted paper applications with a check or credit card information. Today, that process sounds ancient, but at the time it was wildly innovative. Risks can be beneficial when approached in a productive and strategic way.

Justin Tysdal, co-founder & CEO, Seven Corners, Inc., Carmel, Indiana


Embrace failure, and move on.

The one thing I wish I knew when first starting my business is that failure is an option. What I mean by that is, it took me time to realize that one project or product failing does not mean that the whole company is bad and will collapse. Not every idea the company had would pan out exactly as planned, but as long as we played our cards right, the company could still carry on.

Nate Masterson, CEO, Maple Holistics, New York City


Learn to delegate.

I wish I would have known to hire someone, at least an intern, to help me out, so I wasn’t wearing every hat in the company. I am happy that I was able to learn every position in my company, and get the experience of it, including tour guiding, taking reservations, sales and marketing. But I would have gotten so much further faster if I’d hired someone. It took me years longer to develop my company because I was spending too much time “in” the company instead of on it. Nowadays, I’m much more strategic, and I’ve hired a whole team over the years. Even in my day to day, I’m much better at delegating.

Georgette Blau, founder, On Location Tours, New York City


Line up funding sources early on.

I wish we had started developing multiple funding sources from the minute we started our business. The business initially generated enough capital because it was growing slowly. But as we became more successful and wanted to expand, we found ourselves constantly looking to access additional capital. Just because you have access to capital does not mean that you have to use it. But it can be a lifesaver when you need it.

Nick Disney, owner, Sell My San Antonio House, San Antonio


Don’t let weak employees linger too long.

The hardest lesson I learned is not getting rid of weak people sooner than I did in the first few years of running my business. I spent more time managing them than finding new customers. I knew in my gut they were not up to snuff, but out of loyalty to them, I let them hang around much longer than they should have. It would have been better for everyone to let them go as soon as the signs were there. They became more insecure and threatened as we grew, which was not productive for the team. As soon as I let them go, the culture got stronger and the bar higher.

Paige Arnof-Fenn, founder & CEO, Mavens & Moguls, Cambridge, Massachusetts

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