Carolina Conversations: Randy Nelson

By Gayvin Powers

Randy Nelson, author of “The Second Decision: The Qualified Entrepreneur,” an entrepreneur living in Raleigh who sold the first two businesses and is on No. 3, doesn’t plan on slowing down during the second 50 years of life. This month, Nelson talked with OutreachNC about what it takes to be a successful entrepreneur.

Why is it important for people later-in-life to start businesses?

Globally, the age at which people are most unhappy is age 46. The happiness curve goes up from that point and continues to rise at least into our 70s, so translating that statistic into real life…it seems that once we get past the point where our finances are challenged the most (college expenses, weddings, etc.) and our kids are raised, we get a bit of freedom back in our lives. I know that is the case with me; at age 50, all six of our children were past high school and grandkids were on the way!

The second statistic is that the average lifespan of both men and women has risen over the past 25 years, but so has the average time spent living with a disability. For men, we live on average to 78, but we spend the last 10+ years living with a disability. I understand my most productive time will most likely be in the next 10-15 years, which keeps me very focused on building and enjoying now.

Third, there has been research done that shows when the mind starts to slow down, your lifespan also is decreased. My entrepreneurial mind runs constantly, and I am confident that will not make me age any faster but rather keep me young!

In my case, I am 53 years old, and I just started my third business at age 52. Why? I realized that I had way too much gas in the tank still and that I love to be challenged. I plan on building my current business for at least the next 10 years.

I am happiest in my business life when I am building companies, which is where my true passion lies. I highly recommend to everyone who is thinking about starting a business later-in-life to start one that they have a great passion for.

Later-in-life we all have a much clearer picture of what we are great at, what we are not great at and our self-awareness should be very high.

Spending time deciding what you want to do is important. It is just as important to decide what you definitely don’t want to do. Combining your passion with what you are good at is a great starting point!

What made you want to be an entrepreneur?

In the beginning, I was a combination of an entrepreneur and an accidental entrepreneur. In my first business I had partners, and from very early on they were committed to starting their own business. I was the holdout.

I had just completed six and a half years of naval service as a lieutenant in the submarine service and was finishing up my first successful year in a recruiting company with my soon-to-be partners. They were ready, I was hesitant. In the end, the desire to control my own destiny was just too enticing, and I have never looked back. I was energized that the success or failure of the business would be directly related to my efforts.… That was highly motivating for me; a no-excuses mindset has never left me.

I was also highly motivated by observing successful entrepreneurs amongst my family and friends along with the freedom and perks that they seemed to be enjoying (although, as I mention later, perception is much different than reality sometimes).

What do you hope your children and grandchildren will take away from you being an entrepreneur?

Most importantly, what I want them to take away from me is that being an entrepreneur did not take away from them as a son or daughter, or grandson or granddaughter. When all is said and done, I want them to remember me as a Dad and Papa, who was an integral part of their lives!

It is also why my next book, “The Third Decision,” will focus on the personal and family aspects of the entrepreneurial life, and how they are so intertwined,

especially with the business decisions the entrepreneur makes in “The Second Decision.”

My hope, especially in writing the book, is to give them a balanced look at what I did. Every day was not true joy, and even though I always had autonomy, I did not always have control because the economy eventually plays a role in the success of a company in the long run, especially the bigger a company gets.

The facts are sobering: 70 percent of small businesses fail within 10 years, and most mid-sized business under-perform. Sometimes when people see a successful entrepreneur they have the perception that “We have it made,” especially if we have been lucky enough to build a successful business (or in my case, two of them). The reality is that it takes hard work, persistence, luck, risk-taking, focus, creativity, discipline, and many other things to be successful.

I want them to understand that it is a roller coaster ride that sometimes they will love, and other times the ride will make their stomach a bit queasy. Fortunately or unfortunately, the roller coaster ride for an entrepreneur and his/her family is a never-ending ride, because the entrepreneurial mind never shuts down.

On the other hand, I would want them to know that if they are successful, the rewards can be great! In the end, I want them to know that I did what I asked them to do growing up; I tried my best and built my companies with honesty and integrity as their core values.

If your children or grandchildren came to you today and said they wanted to be an entrepreneur, what advice would you give them?

I would be honest with them and talk to them about all of the positive and negative aspects of becoming an entrepreneur. The failure statistics are high but the rewards are also high if you can be successful. I would paint a picture that becoming an entrepreneur does give you the autonomy you desire, but it does not guarantee you millions of dollars or beach homes or extravagant vacations. I would tell them what they need to hear rather than what they want to hear, that the critical success factor of becoming a successful entrepreneur is to work very hard and smart every day of your life! One of my favorite quotes I would share is “It takes 20 years to become an overnight success.”

I would advise them that they need to have an intense focus combined with a passion to succeed in a business they can love, and that to succeed long-term they need to have a defendable differentiator in the markets they serve.

I would advise them to surround themselves with peers (I did through Vistage and Entrepreneurs Organization) that are going through similar challenges and have a coach that they rely on who brings a life perspective to them. I have had a Vistage coach of my own for more than 10 years who fills this role in my entrepreneurial world.

I would advise them to add a strong operations leader who will build accountability and systems and alignment into the organization, and this leader will complement the visionary role that my entrepreneurial grandchildren must excel at!

I would advise them that becoming self-aware is one of the most critical skills that they need to succeed. Stephen Covey defines self-awareness as: “The ability to reflect on one’s own life, grow in self-knowledge to improve oneself and either overcome or compensate for weaknesses.” I would go a step further and let them know that a lack of self-awareness is the fatal flaw for an entrepreneurial leader.

Then I would secretly hope that I could help coach them because I would want them to become successful and to be able to balance their entrepreneurial hopes with their personal/family goals!

What is your motto in life?

Up until now my motto was to always move the ball forward, to make progress and get better as a person and an organization, every day.

My new motto includes the above, but now starts with: “Enjoy the ride!” I have a plaque in my office that I look at every day to remind me that is what I should be doing.

In your book “The Second Decision: The Qualified Entrepreneur,” you talk about different roles entrepreneurs can play in their business. Can you break down some of the traits associated with those roles (being a creator, leader or role player)?


The creator is the startup entrepreneur that gets highly motivated to create their new business from the ground up. Some of the traits associated with the successful creator are: independent, innovative, risk-taker (I like calculated risk better than risk, though!), crazy, fearless, maverick, visionary, intelligent, optimistic and confident.


The role-player is the person who wants to transition from the founder and most likely CEO of their own company to a role in which they can focus in an area that they are passionate about (e.g. sales, marketing, and board member). The role-player makes the conscious choice to not be the leader, the CEO. They are passionate about their company but don’t want the responsibility and accountability of having to lead the organization. I believe one of the best gifts I can give to entrepreneurs is the freedom to make this choice, because in the end they will be in a better position in the organization where they can be truly passionate, and the company will perform at a higher level with a CEO who is the right person for the job. The traits of the role-player could be a combination of those of the leader and creator.


The leader is the CEO of the organization. They want to be the leader and are passionate about the role and all the responsibility that comes along with it. Traits associated with this role are: organized, responsible, steady, strong communication and people skills, disciplined, visionary and intelligent.

You will notice many differences between the leader and creator, but what stays the same are their traits as being an intelligent visionary!

For a company to continue to grow, the CEO has to be “the right person in the right seat, at the right time.” By giving entrepreneurs a choice to find the role that they are passionate about, rather than staying in the CEO role just because they were the founder of the organization, I am giving them the freedom to do what they love: to be the leader (CEO), to be the role-player (e.g., sales leader, board member, marketing) or creator (go start up more great companies)! All of the roles are good choices for the entrepreneur; what is not OK is to stay as the CEO and to not do a great job.

What did your military training do to prepare you to become a successful entrepreneur?

My first business, Orion International, places exiting military personnel into the civilian industry after they have completed their active duty service (we have helped more than 33,000 veterans find full employment after their military service). When I would speak to a potential customer who was considering hiring military veterans, and they would ask me why they should do that, I answered it this way:

“They bring leadership, maturity, integrity, discipline, loyalty and many other skills to the table.” I learned that respect is both given and earned…This taught me that everyone was important, that nobody was any better than anyone else, we simply had different roles, and they were all important.”

What advice do you have for entrepreneurs?

For the “experienced” entrepreneurs who are either starting or in the middle of building their own businesses, you will have to make some balance decisions based on the facts that you most likely have earned the “empty-nester” title, you might be enjoying your grandchildren as they grow up before your eyes, and you have also built a bit of a nest egg and freedom that allows you to travel with your spouse/significant other. With a new thriving business, though, you have to decide just how much focus you are willing to give that vs. your personal life…choices, choices, choices!