10 Lessons Learned From 10 Years as an Entrepreneur

By Kirill Bensonoff 

When I first started out as a young entrepreneur, I created a business agreement with my fellow tech pal on a napkin at a Boston bar. If I could look back and give myself any advice, I would hone in on the following 10 lessons I’ve learned from achieving success by weathering the storms and re-investing in the pursuit every step of the way.

Have Confidence in Your Abilities

My parents immigrated from Minsk, Belarus (then USSR) to the United States when I was 11 years old. With $200 between them, they had to be willing to work hard and have confidence in their abilities to survive. Even if/though you come from humble beginnings, always have confidence in your abilities.

Mature Fast: Know When It’s Time to Grow Up

In later years, I found that school was neither inspiring nor educational. Instead, I spent those years focusing on having fun. I always maintained a small business to help with expenses. From ages 16 to 22, I spent a lot of my free time following my dreams of becoming a DJ, going to clubs, raves and festivals. It wasn't until I turned 23 that I decided to get serious as a tech entrepreneur. You have to mature fast in life in order to be an entrepreneurial success.

Rely on Yourself

Bootstrapping has always been an important approach to my life. I had to rely on my own money and hard work to succeed, and I had to remain frugal. I could never count on my parents to finance what I wanted to do. I’ve always had a job and often ran a business in parallel. When bootstrapping becomes a way of life, it opens up new opportunities.

Look for Inspiration All Around You

My inspiration has always been my uncle Leon, a successful web entrepreneur and one of the early pioneers in the web hosting industry. I’ve found it important to tap into life and stay inspired by reading about what others are doing. This has helped me stay innovative, inspired and wanting to do more. Inspiration can be all around you if you take the time to look for it.

Think About What You Say and Do

After becoming an entrepreneur, it's important to realize that no matter the size of the company, when you are the CEO, the buck stops with you. Even if you have a full executive team, most important decisions will depend on you. You’re ultimately accountable for your business decisions, so invest careful time and thought into making them.

Don’t Be Afraid to Learn From Others

Some of the lessons you’ll learn are outside of the four walls of your business. In my case, I had a great deal to learn from my business partner Alex, who was my hiring manager at the time. We ate lots of Asian noodles together and dreamed big. Don’t be afraid to learn from others: They can be a powerful source of ideas that feed innovation.

Never Stop Looking for Innovative Business Opportunities

My first real business was a web hosting company. I sold the company after about a year for five figures, which was great for me at the time. Soon after, I started my second, higher premium web host. Never stop looking for innovative business opportunities. You might be surprised where you find the ideas.

Shoot for the Moon (But Have a Parachute)

I like to think of being an entrepreneur as a long-term adventure. Alex and I founded our current startup with a back-of-the-napkin business plan and $20,000. The company grew into a brand with over 50 employees and nationwide customers. In 2015, I founded another startup, which started as a side project. Dream big, shoot for the moon, but always make sure you have a parachute.

Get Comfortable as an Entrepreneur

Being the captain of your own ship is not for everyone. Being an entrepreneur is a 24/7 job that requires 100 percent focus and commitment. At peaks, there is no time for family, fun or friends. You have to be ready to commit your life. I’ve found that a true entrepreneur gets things done with no excuses. They think ahead, roll up their sleeves and do what it takes to succeed.

Maintaining a work/life balance as an entrepreneur can also be difficult. I find myself thinking about work on the weekends and at nights. Try and get a good night’s rest, as sleep will ultimately improve your productivity. The problems you may try to solve late in the evening can be resolved with much greater insight if you’re energetic enough to focus on them clearly. Understand that entrepreneurship is a way of life. However, you still have to find a work/life balance and make time for family.

Continue to Push Yourself to Succeed

Whether you're in your first or tenth year, you need to continue to push yourself to succeed. Sometimes doing so requires a fresh perspective. Always be learning and expanding your horizons. Talk to your customers as much as you can. I continue to solve challenging problems, learn new things and seize new opportunities I haven't tried before.


Kirill Bensonoff currently holds leadership positions at ComputerSupport.com and Unigma.

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