Simon Chatfield

Always take care of your customers, and they’ll take care of you.


Simon Chatfield, CEO and Founder of OptimumHQ, is a Software Architect, SaaS Evangelist, and Serial Entrepreneur with over 25 years of experience in the industry. For almost 15 years, he owned a successful software development firm that built custom enterprise software applications for global companies including Apple, ESPN, and American Express. The Chatfield Group also built over 400 custom software systems for small and mid-sized companies with unique business processes. During this time, Simon learned that big and small companies alike faced similar challenges. Business leaders just want software that truly solves their specific needs, and they don’t want all kinds of extra software they don’t need. Pioneering the concept of dynamic data and company-specific workflows, Simon and his team created a new business solutions platform to quickly build complex custom solutions without custom code. Thus, OptimumHQ was born.

Where did the idea for your company come from?

The idea really stemmed from owning a custom software development firm for 15 years and realizing the custom software process is broken. OptimumHQ was founded on the idea of being able to build custom applications without having to start from scratch every time with custom software development. The whole custom software development process – while the outcome of what it can do is amazing – is flawed and quite frankly, it sucks. It takes too long and costs too much. There are too many nightmare project failures. On one side there’s the business that has changing requirements and on the other side is the software developers who are trying to develop the project to scope and the scope is always changing. That whole process needs to change, and that’s where OptimumHQ comes in. With the simple concept of datasets and workflows, OptimumHQ puts the power in the businessperson’s hands to develop their own solutions or work with a Business Analyst or Solutions Architect to develop custom solutions at 10% of the cost and 10x the speed of traditional custom development.

What does your typical day look like and how do you make it productive?

I wake up around 4 am and get all my solo work done first thing in the morning when there are no distractions. And with a full house – my wife, two sons, daughter, newborn granddaughter, and four dogs – it gets pretty hectic! I go to my home office, turn on the TV with news in the background (Fox Business News, Bloomberg, CNBC, etc.), and typically drink an entire pot of coffee while I work. I work on my computer for a few hours, then I do some cardio or lift weights and watch business videos on Youtube or listen to a podcast. Then I get ready to head into the office, which is only about a 5-10 minute drive from my house. Every day is a bit different; it’s usually pretty busy running around town from meetings with partners or clients to internal meetings, but I always try to have fun every day. We have Nerf gun wars at the office, practice shooting hoops, and never miss an excuse to go to happy hour.

After work, I spend time with my family eating dinner, watching movies, playing board games, etc. until it’s time for bed around 9-10 pm. Tuesday is my favorite night of the week: every Tuesday night is reserved for boys’ night, and my two sons and I go out to Buffalo Wild Wings or another fun spot to catch a game on TV and chat about our week. It’s been our tradition for over 10 years. Family is very important to me.

How do you bring ideas to life?

First, I do a quick proof of concept to prove it out, including mocking up the process on a whiteboard or drawing a diagram of how it’s going to work. Once I validate the solution, I hand it off to my team to implement.

What’s one trend that excites you?

The concept of understanding your business workflow is really starting to take off. We no longer really need to tackle that concept with new and potential customers, which makes our lives a lot easier. This is something we’ve been focused on for years, and the fact that the rest of the world is picking up on it is a great thing.

What is one habit of yours that makes you more productive as an entrepreneur?

Clearing the little things off my plate. If there’s a task I can do in a minute or two, I’ll just get it done and don’t put it off. The little things can overwhelm you if you let them.

What advice would you give your younger self?

“Good luck, sucker!” No, but seriously: Earlier on in my career, I would tell my younger self to believe in myself as much as other people believed in me.

Tell us something that’s true that almost nobody agrees with you on.

Software is simple.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Always keep learning. I learned so much after my first endeavor as an entrepreneur and business owner, and I’m still learning all the time. Whether you’re just starting out or you own a dozen successful companies, I think you have to be prepared to keep learning every step of the way. Your work is never truly “done.” There will always be the next big idea, innovation, or risk you need to take to keep moving forward.

What is one strategy that has helped you grow your business?

Taking care of your customers. If you take care of your customers, they will not only do more work with you but they will refer you to other potential customers. I make sure that spirit of taking care of the customer first is in every aspect of my business and every department (not just sales and customer success). One of our core values is doing the right thing for the customer.

What is one failure you had as an entrepreneur, and how did you overcome it?

I don’t believe in failure, I just believe in finding out the things that don’t work and overcoming that.

What is one business idea that you’re willing to give away to our readers?

I don’t give away my good business ideas 😉 You can have this one, though: Somebody needs to invent a system or tool that can go across all devices, email accounts, and browser history to find specific data. There’s so much information coming in all the time and I think “Where did I hear that?” whether it was an email, text message, or a video. There needs to be some kind of system of bookmarks or a search bar that goes across all of your accounts.

(Side note: If you’re looking for a really good business idea, become a partner with OptimumHQ.)

What is the best $100 you recently spent? What and why?

Wedding gift for one of the Solutions Architects on our team who recently got married. We got him a nice bottle of wine, a killer bottle of beer, a trophy that says “Congratulations on Adulting” (he and his now-wife have been together for 10 years), and a few other small things.

What is one piece of software or a web service that helps you be productive?

OptimumHQ. Not to toot our own horn too much, but I greatly believe in the concept of eating your own dog food/drinking your own champagne. This can be easy or tough depending on your product/service and industry, but finding a way to be users of your own experience is critical. In my first company, we often found ourselves following the proverbial, “Do as I say, not as I do” and unfortunately didn’t take time to reflect on it. It’s not that we were hypocrites, we just found the same excuses everyone else does when we were not eating the dog food. This doesn’t apply to my second business because we use our own system to run the entire company; it’s another one of our core values. OptimumHQ is a business solutions platform, and come hell or high water, we’re going to use it for ALL of our business solutions. We have learned so much not only about the usage of the product, but ways to improve it. The payback on putting in the extra time has come back to us exponentially.

What is the one book that you recommend our community should read and why?

“The Great Game of Business” by Jack Stack. It covers the concept of bringing your employees and teams in on the key drivers that they can do to directly impact the business. This enables the business and everyone in it to take ownership. In many ways business is a game and at OptimumHQ we like to have fun, but if you don’t know what the score is how do you know if you’re winning or not?

What is your favorite quote?

“That’s what I do. I drink and I know things.” – Tyrion Lannister, Game of Thrones.

Key Learnings:

  • Eating your own dog food/drinking your own champagne/finding a way to be users of your own experience is crucial.
  • The whole custom software development process – while the outcome of what it can do is amazing – is flawed and quite frankly, it sucks and it needs to change.
  • Software should be (and actually is) simple.
  • Always take care of your customers, and they’ll take care of you.