David Waring – CEO Interview

by | Nov 6, 2020

David Waring

Co-Founder and CEO of FitSmallBusiness

When did you know you wanted to start your own company?

I started collecting cans and selling the aluminum when I was 5, so I pretty much new I wanted to have my own company from the beginning.

What was your original idea for this company, and are you still doing that (or did you pivot, if so, what is the new focus and why)?

Our original idea for the company was to provide a how to site with product and service reviews for small businesses. While there are other companies who did this already, they were focused primarily on providing information to internet businesses and new businesses. We felt like the information for existing brick and mortar small businesses was lacking, and launched FitSmallBusiness.com to fill that gap. While we have expanded in recent years to do some content around startups and internet businesses, the core of our focus and audience is still the brick and mortar small business owner with an existing business.

How long did it take you to finally take the leap, and what was it that pushed you over the fence?

I started my first company when I was 27 which ended up not working out and leaving me dead broke at 30. So I needed to go back to work for several years to rebuild my net worth, so I had enough money to support myself while launching this new venture. That took me about 3 years at which point I decided to take the leap again.

Who inspired you to pursue your dream, and why do you think they believed in you?

My father. He taught me about business from a very young age and taught me that it’s ok to take risks. The worst thing that can happen is it doesn’t work out and you have to start over. Not the end of the world.

Who is your favorite mentor and why?

While I don’t know him personally, I read a lot about Jeff Bezos. I like how he has built a very large business by remaining laser focused on what’s best for his customers and how he has remained consistent throughout many years in his vision.

What was the hardest thing about starting your company, and what did you do to make it through the first stage?

The first year is a real grind and it’s hard to know if what you are doing is working. Having a business partner to work through the uncertainty with was a big deal for me.

What has been the hardest lesson to learn?

When a business grows quickly, you have to change how you operate constantly because what much of what works from an operational standpoint for a small company does not work well for a larger company. This is a tough lesson because often times the same thing that makes you successful as a small company will work against you as a larger company.

What has been the most amazing thing you have experience while running this company?

TGrowing a business from 0 to 8 figures in revenue with no outside investors has been awesome.

What is the weirdest thing you have experienced while running this company, and how did you react to it?

Someone smoking in a video interview. I let it go at the time not to be rude but did not move the person forward.

What is the best decision you’ve ever made while running this company?

Choosing a great business partner.

What is the biggest mistake you made while running this company, and why do you think it happened?

Bringing in an outside executive team instead of promoting people from within. Since this was the first time I have been the CEO of a large company, I thought I needed outside help in order to run the company effectively when we got to a certain size. I believe this ended up working against our success and since removing that team and focusing on promoting people from within we are executing much more effectively.

How has the coronavirus pandemic affected your company?

It has hit us but not as badly as I would have expected.

What keeps you passionate about your company?

Delivering the best answer to small business owner’s questions.

What daily routine have you developed to help you take care of your mind, body, and soul?

I meditate and exercise 4 days a week. Meditation to start the day and exercise to break up the day.

What one thing would you like people to take away from this interview?

Don’t be scared to follow your dreams.

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About the Community

On the podcast, Sean talks with entrepreneurs about the reality of their struggle to succeed, as well as answering questions from the community, and sharing nuggets of wisdom from his own life.


Discover through these amazing episodes the courage to open your mind, heart, and soul to the world so you can be the best entrepreneur possible, respect the people you work with, and improve the world with your company while not hurting others or yourself in the process.

Sean Weisbrot

Sean Weisbrot

Sean is an entrepreneur, investor, and advisor based in SE Asia for over 12 years. He is passionate about Psychology and helping others improve themselves.
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