3 Key Takeaways an Entrepreneur Learns After Starting their Second Business


By Simon Chatfield, CEO/Founder, OptimumHQ

When I started my first company, I admit that I was shooting from the hip most of the time. I imagine that most young, scrappy companies do the same – try to stay afloat long enough to figure things out, and before anyone realizes that you don’t know what you’re doing.

During this initial time period in a founder’s career, being scrappy and rolling with the punches is critical to the growth of the entrepreneur. If you’re not willing to risk your decisions against the world and are too afraid to take chances, then you don’t have much hope in being a success. For every plan that is laid out, no matter how long you’ve thought on it or went through all the scenarios, you simply don’t know enough to know what you don’t know. And that’s OK, as long as you’re not afraid to keep moving. In my first company, I knew where I wanted the company to be, and as much as I’d love to have a nice straight line from starting point to my destination, I had about as many turns, stops, zig zags, and upside downs to give a rollercoaster a run for its money. I wouldn’t change anything about that journey as it’s what gave me the scars, confidence, and – after the successful sale – the funds to start my next endeavor.

As I’m writing this today, I’m in the middle of building a new company and it’s on track to blow away the success I had the first time around. There is, however, no doubt that this would not be the case if I hadn’t been through the wringer a few times before. Here are some key items I’ve done differently the second time around which have been instrumental to get where we are:

  1. You can’t take your company to the next level with “Good Enough.” I used to call myself a realist and would shun the idea that everything needed to be perfect. In my first company, we did so many things just “good enough.” From our internal systems, to managing invoices, to processes and workflows. We had a TON of things to do, so the “good-enough-and-get-it-done” approach was a crutch for us to get by while we thought we were working on other, more important items. And that approach worked up to a point, until the infrastructure under the company just wasn’t solid enough to support the next level of growth or scale. For the key systems in your company, make sure it’s being done correctly and can support your company at a larger scale for the future. You’ll never be perfect, but make sure you’re more than just “good enough.”
  2. Eat your own dog food/drink 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 actually 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.
  3. If cash is king, then culture is queen. The first time around, I didn’t pay much attention to
    company culture; it was more of an afterthought, and didn’t go much further than saying “Yeah, we should have that.” It’s not that my personality was different, or even that I presented myself much different than I do today. What IS different is that at OptimumHQ we don’t hire someone who isn’t a fit for our company culture. My philosophy is that if I’m not enjoying myself, or having fun, what’s the point? And I really like working with high-performing people who like having fun as much as they like building cool things or solving cool problems. You can pay people well to get a job done, and you can force them to file their TPS reports (Office Space, anyone?), but you certainly cannot force a culture. Keep a good and positive culture in your business and it will keep you – and the team – eager to come in and tackle big problems.

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. Stay hungry for knowledge, fellow entrepreneurs, and keep striving to be better.


For 15 years, OptimumHQ founder and CEO Simon Chatfield owned a successful custom software development company that built custom software applications for global companies including Apple, ESPN, and American Express, plus hundreds of SMBs. He 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 systems 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, called OptimumHQ.

Learn more at www.optimumhq.com


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About the Author
Positive Phil is a motivational keynote speaker & start-up consultant. Focusing on revenue generation & new business acquisitions. Founder & CEO @Audio inc. Business developer since age 12. Public Company Start up CEO, $investor -Public speaker #podcaster #motivator Enjoying life.

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