Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with J.R. Flatter, Founder of Two Roads Leadership, located in Fredericksburg, VA, USA.

What's your business, and who are your customers?

I help leaders blueprint and build coaching cultures! With four children headed to college, I started Two Roads Leadership immediately upon my retirement from the Marine Corps, as much out of necessity as passion. Foolish me – with education as my top parenting priority - for their entire lives, I had promised all of my children I would pay for any school they could get accepted into! And now they were graduating high school, and the tuition bills started flowing – for MIT, Boston University, George Washington University, and The Rochester Institute of Technology!

For most of my Marine Corps career, I knew I wanted to start my own business when I retired, but I thought I would have to "lily-pad" hop from one position to another until the opportunity presented itself to launch my own gig. However, everything came together as I was transitioning to civilian life. I secured a 90-day contract as my first project – which paid me more in three months than any employer had offered for an entire year's salary. The logic was that if I didn't have another contract on the 91st day, I would accept one of the original offers for employment and start the original plan. 20+ years later, here we are – still succeeding and growing!

The next generation of leadership is in place – and killing it! I rest easy knowing their vision and passion carry us to new heights! And I can focus on Leadership Development, Coaching, and Coach Training – which was my original plan all along – but life and events took the business in other directions!

Tell us about yourself

According to Shakespeare, I am now in my 5th Act of Life in the role of "Justice" with my "round belly… and wise saws…!" As a parent of four grown children and the leader of a global organization, I appreciate the importance and value of creating and executing a long-term personal and professional vision. With this appreciation in mind, my focus in my 5th Act is helping others successfully blueprint and achieve their long-term visions!

What's your biggest accomplishment as a business owner?

My biggest accomplishment is creating a lasting company - with a world-class culture - that can help our team identify and achieve their life goals and objectives!

As I turned 50 years old, I was fortunate to have accomplished my three life goals -educate my children, raise them as a family, and create some financial freedom! So I retired - to an expected next chapter of philanthropy and leisure - but doing so nearly killed me! During this 18-month retirement experiment, I realized my value and calling remained in a "for-profit" business - helping others - my corporate team and our customers - identify and achieve their life's goals!

What's one of the hardest things that come with being a business owner?

In my industry, contracts come, and contracts go - regardless of our success in execution! As such, the hardest part is saying goodbye to high-performers whose work has either finished or gone away!

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Ensure your "significant other(s)" are onboard with your journey. I tell everyone thinking about the entrepreneurial path. Ask your life partner if they are ready to have a third "person" in your relationship - because the business will always want more time, attention, and resources!
  2. The first gig is easy - because we all know someone who knows us and trusts us enough to give us work. The 2nd, 3rd, and 100th become much more difficult!
  3. Live like a starving student in the early days! Don't lease more space than is absolutely necessary to pay yourself just enough to survive and keep your team equally lean.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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