Written by Erik J. Olson. Posted in .

The Struggle of Starting Your Own Business

I received the Entrepreneurial Excellence Award in 2016. It was an amazing honor and the award sits proudly on the bookshelf in my office. As a result of receiving the award, I’ve kept close tabs every year since to see who I know on the list of honorees.

As a member of the Entrepreneurs’ Organization (EO), I was pleasantly surprised when I noticed the abundance of EO members and strategic alliance partners who made the list this year. Of the sixteen honorees, six are associated with the local EO chapter. These members, as well as all of the honorees, are driving the vision and spirit of the business world in Hampton Roads.

Entrepreneurialism is a tough career choice. It can be risky, stressful, lonely, and challenging. Common knowledge dictates that if the risk is large, the reward will be too. While that may hold true for some, it’s more likely that there will be little to no reward for most.

Many entrepreneurs struggle to get their company off the ground, to gain traction in the marketplace, and to get the attention of prospective customers. More entrepreneurs struggle and fail than succeed.

According to the Small Business Administration, 30% of new businesses won’t survive their first two years in business. The outlook is even bleaker after that: 50% fail to reach the five-year mark and only one in three survive to their 10 year anniversary.

To qualify for EO, a company must have gross revenue of at least $1 million. Similar to the bleak odds of surviving long term, the odds of reaching revenues at that level are low.

According to the book ‘Scaling Up’ by Verne Harnish, only 4% of companies reach more than $1 million in revenue. The odds are significantly lower for additional growth. Only one in 10 of those companies (or 0.4% of all companies) will grow to $10 million. After that, a meager 17,000 companies generated more than $50 million in revenue.

Clearly, there is no guarantee when starting a business and the chances are very low that you’ll grow to a million or multimillion dollar business. With the chance of success and riches being so slim, why do entrepreneurs start down such a precarious path?

Most entrepreneurs say they are inexorably drawn to the challenge. Competitive to the extreme and confident to the core, they are willing to battle the odds that others flee. My friend and fellow entrepreneur, Danijel Velicki, often says he started his business because he’s “willing to bet on himself”. It’s a mentality that is present in all entrepreneurs that I know.

2019’s award winners are entrepreneurs who were willing to bet on themselves. They run companies from a wide variety of industries and different business models. There is no “one size fits all” mentality when it comes to entrepreneurialism in our region.

All the honorees deserve recognition. Of those, I’d like to take the opportunity to recognize the six EO members that I know personally who are beating the odds on a daily basis.

  • Richard Braun of The Braun Agency
  • Jeremy Grogg of KEES Vacation
  • Drew Monroe of Prosper Insurance
  • Kimberly Pomares of Courthouse Academy
  • Shelley Smith of Premier Rapport
  • Ben Young of Hybrid Air

EO is also in the unique position to field a proven group of business leaders for the panel on entrepreneurialism being held before the awards show. The panel consists of:

  • Danijel Velicki of OPUS Wealth Management
  • Bethany White of Bethany White Realty
  • John Hall of AG Wraps
  • Scott Prunty of SOLID Structures

Entrepreneurialism is a tough, lonely, and often unrecognized career journey. Recognition of their abilities to start, run, and scale their businesses is a great honor for each entrepreneur who receives this award. Congratulations to all the honorees.

For those who may feel like they’re struggling on their entrepreneurial journey, I encourage you to seek out a group such as Entrepreneurs’ Organization. Organizations like EO exist to help entrepreneurs not only cope with the stress of running a business but to also teach entrepreneurs how to survive and thrive even in turbulent times. Alternatively, there are other similar entrepreneurial organizations such as Vistage, The Alternative Board, and the Young Presidents Organization. The important thing is to find a group that works for you.


Erik J. Olson is an award-winning digital marketer & entrepreneur. The Founder & CEO of Array Digital, he is also the host of the Journey to $100 Million Flash Briefing and daily podcast, the organizer of the Marketers Anonymous monthly meetup, and the marketing and communications chair of EO Southeast Virginia.


Erik J. Olson

Written By Erik J. Olson

Erik J. Olson is the Founder & CEO of Array Digital—a marketing agency that enables its clients to achieve their dreams, fulfill their missions, and impact more lives with their services.

Website Design, Search Engine Optimization (SEO), Online Advertising, Social Media & Digital Marketing.
© Array Digital LLC

Website Design, Online Advertising, SEO, Social Media & Digital Marketing.
© Array Digital LLC