Going Against the Flow: James Kenigsberg, CTO of 2U

James Kenigsberg is the CTO and Member of founding team at 2U. At 2U, Kenigsberg has translated his passion for technology into creating award-winning learning management platforms, client relationship management systems, mobile applications and cloud-based architectures. Their team is working with forward thinking universities like Yale, UC Berkeley, Northwestern and NYU to create a future where online students globally have the same rights and responsibilities as their on-campus counterparts.

Prior to 2U, Kenigsberg led the technology and product team at The Princeton Review where he created and managed the company's award-winning assessment products. He was also formerly a part of technology and product development teams at Thomson Financial and Ogilvy & Mathers.

James Kenigsberg

What does entrepreneurship mean to you, and what underlying characteristics do you see in successful entrepreneurs?

James: Passion combined with fearlessness are key traits of an entrepreneur. Start with passion - the contagious passion is what gets people to buy into and support your ideas. From there, you have to have no fear. Entrepreneurship is believing that you and a few close friends are the best people to execute on whatever it is you're passionate about. You will meet people who will tell you that your ideas won't work, or that they can do it better. But you have to stand your ground and have no fear. If you are the best, you will make it happen. Between the hard work and the wearing of many hats, having passion and fearlessness will carry you through the stresses of being an entrepreneur and will ultimately drive you toward success.

What are you most proud of in your professional career? If you could do something over in your life, what would it be?

James: My biggest accomplishment has been building a team that is constantly innovating at 2U. Being able to bring together the right people, choose and create the right technologies, and manage the team so they all work well together, has helped us achieve the breadth of technology we are able to offer to our university partners and their students.

If I had to do it all over again, I wouldn't have wasted so much time looking for jobs that fit my skillset. I should have been looking for jobs that inspired me. I didn't have passion for the company mission in my previous jobs. They were good jobs, and they provided me with necessary skills, but at 2U, our work is changing the world. We're helping non-profit universities expand educational access to students worldwide in fields including social work and business analytics, and that is something I'm truly passionate about.

Tell me about an instance where you had to go against the flow to realize your goal.

James: When we started 2U, building platforms on cloud technologies like Salesforce, Amazon Web Services, and other software-as-a-service providers wasn't yet a popular business practice, but we knew that was how we wanted to build 2U. Today, it's a no brainer; everyone is in the cloud. But back in 2008, we heard a lot of doubters say, "real businesses don't do things like that, they don't hire SaaS companies." We took a leap at 2U and did it anyway, and it's been one of our best business decisions.

What is one piece of advice you would give to fellow experienced entrepreneurs, to keep in mind as their business grows?

James: Continual learning is an integral part of every position in business. Experienced entrepreneurs and managers need to keep expanding their knowledge base, and looking to only senior staff shouldn't be the way. It's time to flip the script: look to your junior staff for mentorship and training by tapping into their skillsets and interests. Spending time with those in the trenches on a day-to-day basis can teach you a great deal and will help you evolve as a leader. You'll gain new perspective that will allow you to become a better manager and be able to more deeply understand how your employees work on a day-to-day basis.

Where do you draw inspiration from?

James: I like watching how younger generations are doing things and learning what they're passionate about. It's fascinating to me how serious my kids, Viktor and Daniel, get about computer games and coding, through things like Minecraft. Being in the education industry, I'm also drawn to understanding where and how younger generations are learning. I want to be on the forefront of anticipating those trends and to develop new ways of thinking. I never want to be too old to be able to connect with them and be able to discover new things.

If you were to give advice to your 22 year-old self, what would it be?

James: Seek out mentors. Don't spend your time concentrating on making money or searching for jobs; search for mentors to help you succeed personally and professionally. I wish I would have found my mentors much earlier in life. They put me on the right path for my career and helped me become successful. Look for mentors outside of your office, at events like industry Meetups or through your network.

Follow James Kenigsberg at @JamesKenigsberg, check out the other interviews in Going Against the Flow series at http://www.huffingtonpost.com/charu-sharma/ and join this movement to empower 1 million female entrepreneurs on goagainsttheflow.com.