Top 10 Things that Entrepreneurs Don’t Like Doing but Ultimately Do by Brian CalifanoAs we approach our ten year anniversary, we have learned a lot about entrepreneurs, small business owners, and what it takes to successfully run a business. David Letterman, the well-known late night host, used to have a segment on his show called The Top 10 List. Since he left in 2015, we think it’s time to bring that back and provide AcceleratingCFO’s Top 10 Lists of things we have noted over the past ten years. The next series of posts will be a tribute to both our clients and colleagues as well as an acknowledgment of our ten year anniversary in February 2024.


#10. Delegate non-essential duties to others: As an entrepreneur you bring unique and uncommon skills and experience to your clients that cannot be easily found. Writing checks every month is something that anyone can do under your guidance. A critical lesson that entrepreneurs learn is to let go of duties that others can do. 

#9. Overcome fear of taking on additional debt: Even though interest rates have risen over the past two years, the need for funds to fuel growth has never been greater. Entrepreneurs need to understand that money is the blood flow of its business and that without it the business will struggle and often cease to exist.

#8. Take eight minutes for yourself: It’s important to calibrate your mindset before you start your day. Every single successful business person states that their morning routine helps to establish the framework of how successful their day is. Whether it’s meditation, exercise, or reading, establishing a strong morning habit is imperative for your mental health. 

#7. Hire the best person for the job (instead of someone you already know): Although it’s a blow to your ego, surrounding yourself with people smarter and more capable than you is vital to growing yourself and your company. You cannot do it alone — and hiring talented people to work for you is something that will enable you to elevate your skills set and challenge your core values. 

#6. Trust the hybrid environment: Technology has transformed the workplace from one of physical presence to a mix of virtual and in-person attendance. Be flexible when possible to adopt workplace policies that welcome individuals who are valuable to your company and can contribute independently with minimal supervision. 

#5. Understand what a CEO does: As the leader of the company, everything that you say and do sets the tone at the top. It is important to always maintain a positive outlook for your employees and customers so that they can rely on you and trust you in good times and bad. 

#4. Hire a qualified finance leader: Whether you have a full-time or fractional resource, your Chief Financial Officer is a person who aligns the financial goals of the company to its mission statement. They are more than a scorekeeper — they are a finance partner who will be the source of solid analytical skills and data interpretation. 

#3. Say No: There are many shiny objects, whether that’s opportunities or people. Entrepreneurs and business leaders need a discerning eye. Sometimes the golden opportunity is just a bad egg. 

#2. Manage by analysis (not emotions): All entrepreneurs will ultimately face choices that they know in their mind is correct but tugs at heart strings. Some of the toughest decisions made are done so because either the marketplace or the financial performance dictates it is the right thing to do. Weather i’ts shutting down a plan or laying off employees as part of a cost reduction, relying on data and information often is something doesn’t come naturally to entrepreneurs. But without sticking to facts and figures, many companies underperform or close because of an entrepreneur’s inability to act decisively. 

#1. Take the Plunge: A life without challenge is a life not worth living. Being an entrepreneur is not always a bed of roses, but living your life the way you want to and creating a business from scratch is both rewarding and fulfilling. We spent many years in jobs that we felt bored at because we didn’t have the courage to create our own business. However, once we got the courage and the game plan to create our business, we have never looked back. For all of you reading this, and perhaps wondering “If I only had ____, I would definitely start my own business,” we say: get off the sidelines! Entrepreneurship may not be for everyone, but if you have the urge and the passion, we encourage you to go for it. 

Take-away: If you are looking for a Fractional CFO or wondering what a Fractional CFO does, please contact us at

Share this

Posts That Might Interest You

This site uses analytics, cookies and/or other 3rd party technologies that may have access to your data, which are used to provide a quality experience. If you do not agree, opt out and we will not load these items, however, necessary cookies to enable basic functions will still load. Visit our Privacy Policy to learn more.
Contact Us:
Email us at for requests involving data we collect. View our Privacy Policy for more info.
Opt In / Out:
To change your opt in settings, please click here to opt out or in. Or, close this popup.