Kevin O’Hara is a serial entrepreneur and successful executive with decades of experience leading and innovating. He most recently founded CUE.

I started my career working for a very large company, but today I consider myself a serial entrepreneur having founded or co-founded five businesses. After I made my transition to being an entrepreneur, the two questions I have probably been asked more than any other are: how did your career change so much? And, what constitutes a good idea for a new business?

In my case, the answer to both questions is highly intertwined. I will address each question in separate blogs.

When I started my career, I went to work for a very large construction company in Omaha, NE. Because nobody told me anything to the contrary, I assumed that I would work there until I was 65 and then retire with a nice pension.

I loved my job, and I loved building things so the 40-some years of work ahead of me were going to be enjoyable. But a funny thing happened along the way. I transitioned from helping to build things, to helping to build businesses, to building businesses.

In the mid-eighties, the first competitive communications networks started to get built using fiber optic cables. Peter Kiewit Sons, the company I was working for, contracted to build a tremendous amount of these early networks.

One of the companies they contracted to build the network for was a start-up that required Kiewit to do a fair amount of due diligence prior to committing to building the network. That diligence identified an opportunity for Kiewit to invest in the start-up and provide the capital to allow them to expand dramatically.

The company was renamed Metropolitan Fiber Systems (MFS) and as part of the investment, Kiewit insisted on performing all construction and engineering: I was tasked with overseeing all the work.

A couple of years later, I was asked to join MFS with a much broader role. I continued to grow professionally, get promoted, and ended up as one of the senior officers for the company when it was sold in 1996 for $14.6B.

While this was a tremendous personal and strategic success, I admit that I didn’t think the idea was very good at the beginning and I only joined the firm reluctantly. Besides not fully appreciating the size of the business opportunity, I was concerned with the level of risk associated with going to work for a start-up. Plus, the career track was not well defined. However, I learned that you can make a much bigger impact on the business, learn a tremendous amount beyond your area of specialization, and potentially make a lot more money if you are part of a successful start-up.

Based on the success of MFS, I joined the former CEO and CFO of MFS to help start Level 3.

While the opportunity at MFS was created by a regulatory change that allowed competition in what had historically been a monopoly business, Level 3 was started to take advantage of a revolutionary advancement in technology that we believed would be difficult for any of the incumbent carriers to adopt. It was radical enough that the disruption created by this technological shift could completely upend the industry.

While there were some difficult times along the way, the strategy has proven to be correct, and Level 3 today is a $10B + annual revenue business and one of the few survivors in an industry that looks nothing like it did 20 years ago.

Since leaving Level 3, I have started 4 other businesses. I have sold 2 of the businesses and the other 2 businesses are at an early stage.

The decision to leave a comfortable situation with a large corporation was scary. However, once I made the decision to join my first start-up I committed myself to making the transition successful. 25 years and 5 companies later, I know I made the right decision for myself and have a hard time contemplating ever working for anyone else. There are trade-offs between the two paths to be sure. But when I found myself not fully engaged 2 years ago, the decision to start another company prevailed, and that company is CUE.