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3 Ways I Ran My Company Differently the Second Time Around

Like many other entrepreneurs with young businesses, I tended to do things on the fly when starting my first company. During your first run I think it is common to try to stay afloat long enough to figure things out for yourself before anyone else discovers that you actually don’t know what you’re doing.

In the initial phase of any founder’s career, growth and discovery comes from rolling with the punches for a while. Being willing and able to take chances and risk your decisions is crucial when it comes to finding success. No matter how much you plan, strategize, or consider every scenario, there will always be things that you don’t know. It’s a normal and necessary part of growth to be able to accept that you have much to learn. The key is to be persistent and keep moving.

In my first company, I had a vision for exactly where I wanted things to go. Although it would be great to have a neat line from the start of the company to the goals I had set, it isn’t a very realistic expectation. In fact, my company’s “line” ended up resembling some sort of wild rollercoaster. Although the journey may not have always been clean and straight-forward, I wouldn’t change a thing about it. After all, the rollercoaster ride gave me hard-earned experience, confidence, and, eventually, the funding I needed to begin my next venture.



Today, I am in the process of building my second company that is already on track to vastly overcome the success I had with my first entrepreneurial experience owning The Chatfield Group. With that being said, my current track to success would not be present without my prior experience. Here are some key things I’ve done differently the second time around that account for where OptimumHQ is today:

Being a company that is “good enough” isn’t actually nearly enough.

As a former self-proclaimed realist, I tended to dismiss the idea that everything had to be perfect. Many aspects of my first company were labeled “good enough” when it came to our internal systems, managing invoices, and processes/workflows. Considering the fact that we had so much to do, the “good enough” approach was a way for us to spend our time on seemingly important tasks and shrug off seemingly unimportant ones. That approach worked for the short-term, but eventually our company foundation wasn’t strong enough for us to achieve our long-term goals. The moral of the story is this: make sure that the key systems within your company are being done correctly to ensure a brighter future. Although absolute perfection is unattainable, always make sure that you’re more than just “good enough.”

Eat your own dog food/drink your own champagne.

This point can vary in difficulty depending on your product/service and industry; however, finding a way to be your own user is an important part of running a successful business. In my first company, we tended to find excuses for why we weren’t eating our own dog food. In my second business, we take pride in utilizing our own software to run the entire company. Considering OptimumHQ is a business solutions platform, why wouldn’t we use it for all of our business solutions? In becoming our own user, we have learned more about our own software’s functionality and ways we can improve it.

If cash is king, the culture is queen.

During my first time around, company culture was less of a priority and more of an afterthought. We never truly committed to new ideas meant to improve our in-office quality. This time around, we make it a point at OptimumHQ to not hire anyone who doesn’t fit our company culture. My philosophy is that if I’m not enjoying myself or having fun, then what’s the point? It’s great to work with high-performing problem solvers who can have fun at the same time. Of course, you can pay people well to get the job done and force them to fill out their TPS reports (Office Space, anyone?), but at the end of the day you can’t force culture. Prioritizing a fun and positive culture in your company will keep you and your team eager and willing to solve problems.



Although I have already learned a lot from my first experience as an entrepreneur and business owner, I still have much to learn and more room to grow. Whether you’re just beginning your journey or are already a successful entrepreneur, it is important to remember to always be open to learning more. Your work will never truly be done, and the next big thing is always around the corner. With this being said, always stay hungry for knowledge and continue to strive to be better.