Entrepreneurism & the American Dream

By Blog Greg Olson

Is owning a business part of your American dream?

If so, you’re not alone. According to findings from Kabbage, a financial service and data platform, 85% of small business owners believe that being your own boss and owning a business is the American Dream.

Over the past 20 years, I have met with 1000’s of companies and people wanting to start their own business. I have seen incredible successes and some horrible failures. While owning a business is a dream, you need to work to make sure it doesn’t become a nightmare.


Startup 101

As an entrepreneur and Founder of GROWL, I wanted to share our quick list for startups. Over many conversations with business leaders and founders, we’ve found that while these steps seem so simple, many go by the wayside amid business excitement like logos and colors. Use the following to help guide your decisions through the entrepreneurial process.

Correctly Set-Up Your Company

When you’re starting a business, you need to understand your brand and your why. Follow these steps to help get your company set-up for success:

  1. Find a name that accurately represents your business. Then, check for the URL. Many times, you’ll come up with a great name, but the URL is unavailable.
  2. Incorporate and determine the legal structure. Find yourself a good accountant and attorney.
  3. Get your business an EIN to separate yourself from your company and open up a business banking account.

Finance and Accounting

One of the best tips I ever received was to find a great bookkeeper and accountant, and this has been the best investment across all of my businesses. While you may not have studied finance or accounting, there are many required financial reports that you need to understand, complete, and review. Such reports range from profit and loss statements, cash flow, WIP, balance statements, and many more.

Understanding your finances helps you get and keep your business running while guiding investment and business decisions.

Strategy and Plan

It is crazy how many businesses start without a strategy. To be effective, you need to have a plan and work it. Be sure to include the following:

  1. Goals
  2. Marketing
  3. Business strategy
  4. Sales plan
  5. Possible exit strategy/contingency plans

In the beginning, review your plan daily and directly align it with your financials.

Curate a Personal Board of Advisors

A key to my success has been a personal board of advisors and business coaches typically made up of experienced business leaders and industry experts. Personally, my advisors include a financial advisor, lawyer, sales leader, and industry insiders.


When starting your own business, you HAVE to love sales. Can you pick up the telephone and call a random stranger and ask them questions? Can you talk at a networking event and ask for a meeting? You need sales to grow your business.

Bonus tip: create more meaningful connections by picking up the phone and talking to people rather than sending an email or message.

Culture and Team

In today’s world of business, high-performing employees will leave jobs because of toxic work environments; thus, making culture one of the most important aspects of your company. As you get started, you have the opportunity to build a culture that will attract employees and clients alike. My top three tips for culture:

  1. Have a mission and be able to articulate it
  2. Treat employees like your best customers
  3. Keep it natural and model culture from the top

Ask for Help Early and Often

This is a big one. Most entrepreneurs are pretty stubborn. We will burn the midnight oil, stay at work late nights, miss friend and family events, and continue to search for answers by ourselves. I have found that by asking for help early, we tend to be happier and bring in support to figure out the tough times together.

Delight Your Prospects and Customers

From day one, part of your strategy should be about delighting your prospects and customers. This is so important to success that I wanted to call it out separately. Why should you do this? Delighted customers refer other customers and become customers for life. Make it easy for customers to work with you from on-boarding to invoice.

Become an Expert

Many years ago, I had the opportunity to work with Blair Enns, who is a business consultant. He discussed expertise. He asked me: “Are you a mile wide and one inch deep in expertise or one inch wide and a mile deep. Which one do you think is more profitable?” The outcome of this answer is to specialize and become known for that expertise and specialization. It will make a world of difference in your entrepreneur journey.


Final Thoughts

This is a pretty hefty list and one that I wish I would have read before starting out on my own. I look for the calm moments between the ups and downs now that I am older and wiser – or at least grayer. A few habits I’ve developed to help me through my entrepreneurial journey have been:

1. Journaling

To get things out of my head and onto paper. This exercise has helped me solve some of the biggest challenges.

2 Daily meditation

Many find mediation to be silly; however, in today’s world of constant connection to devices and speed of response, I find it one way to give my mind a breather and to help find calm in the chaos.

3. Support groups

Through the daily stress of running a business, finding or starting your own support group of other business owners or founders is immensely helpful. You will find solace in the fact that you are not alone in the stresses of running a business and together find resources and options to move forward.


Entrepreneurial Support

Knowing the stresses of running my own business and seeing the impacts on those in my support group, one of my latest passions is to discuss entrepreneurialism and mental health.

Mental Health in the entrepreneurial community is suffering; according to a study by Michael Freeman of the University of San Francisco. (More here: https://techcrunch.com/2018/12/30/investors-and-entrepreneurs-need-to-address-the-mental-health-crisis-in-startup-culture/)

This study stated that approximately 50% of entrepreneurs and business founders suffer from at least one form of mental health condition during their lifetime. Part of the conclusion could be that you need to be a little crazy to start a business. In all seriousness, starting a business is tough, and there can be more tough times than good.


As you begin your entrepreneurial journey to the America Dream, I’d like to leave you with the words of Richard Branson: “The secret of success is to do the common thing uncommonly well.”

I wish you all much success and prosperity. Need advice, reach out: greg@growlagency.com

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