We recently connected with Deryck Richardson and have shared our conversation below.

Alright, Deryck thanks for taking the time to share your stories and insights with us today. If you could go back in time do you wish you had started your business sooner or later

I’ve been a full-time entrepreneur for more than a decade now, but in reality, I’ve had some form of a “side hustle” for over 25 years—whether that was a part-time business or an MLM-style venture. I think I always knew I was meant to be a businessman. Still, as a father of four with a wife who stayed home to raise them, the stability of a corporate paycheck felt like the safer choice.

I genuinely enjoyed leading sales teams and did very well as a Director of Sales. I’m grateful that I’ve never had a job I dreaded—not since I was a teenager. But when I finally made the leap into entrepreneurship full time, I quickly realized I should have done it much sooner.

For a long time, I called myself an entrepreneur, but I don’t think I truly became one until I experienced what it’s like to live without guaranteed income. That level of risk changes you. Now that I’m seasoned and understand how to manage entrepreneurship, there’s no going back.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

As a Serial Entrepreneur I own several businesses, but the “granddaddy of them all” is Richardson Marketing Group. RMG started as a lead-generation company serving insurance agencies, and over time we’ve expanded into additional verticals—including roofing, window and siding contractors, solar installation companies, and others. That said, insurance leads remain our core product and foundation.

I’ve been in insurance lead generation for 17 years, and I’m fortunate to have learned the industry from multiple angles. I began as a sales representative in 2009 and quickly worked my way up to Team Leader and then Sales Manager. When that company exited in 2012, I gained firsthand exposure to how small-business exits work. I later joined a competitor as a Sales Manager and eventually Director, which allowed me to see how a different leadership team operated within the same industry. Those experiences gave me the perspective and confidence to go out on my own.

A close friend approached me about starting an insurance agency—he understood insurance, and I understood leads. It was, and still is, a perfect partnership. My partner, Joshua Harris, runs Freedom Direct Life Insurance Services, which operates out of the same building as RMG. Learning the insurance business itself has been invaluable in shaping how we guide and grow our marketing company.

Along the way, I’ve picked up practical insights that help entrepreneurs succeed. That led me to write Go Play: The Ultimate Road Map to Winning the Game of Life, which opened doors for speaking engagements and coaching opportunities. I’ve fully embraced my coaching business and truly enjoy mentoring and guiding young, business-minded individuals. While I had some mentorship early on, it wasn’t nearly as hands-on as what I now provide to my clients.

I’m also always open to investing in or acquiring small businesses when the opportunity makes sense. My first product-based venture launched in 2020 with Blackwoods by Deryck Richardson, a sunglasses brand sold primarily online and through local retailers in Columbus, Ohio. Not every venture works out, of course—I briefly owned a coffee business as well, but it wasn’t the right fit. Each experience, successful or not, has added to the lessons I carry forward.

How do you keep your team’s morale high?

RMG has received several awards over the years, ranging from ethics to financial growth, and we’re proud of all of them. The one that means the most to me, however, is being named a three-time Best Places to Work winner in Columbus, Ohio. That recognition speaks directly to how we treat our team and how seriously we take culture and morale.

Let’s be honest—9-to-5 jobs can be tough, especially in a sales environment where growth can feel limited and every day is a grind. To break up that monotony, I’m a big believer in creating moments that make work enjoyable. Random spiffs, prizes, team lunches, off-site outings, or team-building trips go a long way in helping people reset and stay motivated, especially in a role that involves a lot of phone time.

At the same time, culture has to be protected. One of the early mistakes I made was believing that if a sales rep was profitable, they automatically deserved a seat at the table. I’ve learned that unchecked negativity can spread quickly and undermine an entire team. Sales isn’t for everyone—but for those who thrive in it, they deserve to work in an environment that’s supportive, positive, and built for long-term success.

Can you open up about a time when you had a really close call with the business?

Entrepreneurship is hard—and you have to be good at handling hard. You have to expect it, prepare for it, and anticipate it. It would be ridiculous for a boxer to train for a fight and believe they won’t get punched in the mouth. It would be just as unrealistic for a football player to step on the field expecting not to get hit. There are hits in this game, and if you can’t take them, entrepreneurship probably isn’t for you.

I’ve had several near-death moments in business, but each one has made us more seasoned at handling adversity. Once you’ve lived through those moments, you recognize the signs faster and you’re better prepared for the next challenge when it comes.

In 11 years of business, I’ve never missed a payroll—but I vividly remember the first time we almost did. We were waiting on a wire transfer from a client, and it was late. Early on, we needed every dollar exactly when it came in. We were truly living week to week. Payroll that week was about $9,000, and we had roughly $2,500 in the bank. Panic set in. We scrambled to make payroll, and our team never knew how close we came or how hard we worked to cover every penny.

Later, I used that experience as a teaching moment when performance started to slip. After several tough months, I told the team I would never again pull from my personal savings to cover payroll—everyone needed to pay for themselves. Unfortunately, in 2022, I had to break that promise. That day, I let go of five hardworking people—individuals who helped build RMG into what it is today. It was one of the hardest decisions I’ve ever made.

But while they were good people, the business wasn’t sustainable with the structure we had. In entrepreneurship, you have to make the right decision for the business, even when it hurts. Feelings can’t be the driving factor. I remember crying when I let them go—and I’m not a crier—but it was still the right decision.

Since then, we’ve continued to grow with fewer people and less payroll overhead. That lesson was painful, but it taught us how to do more with less—and it ultimately made the company stronger.

Contact Info:

• Website: https://www.richardsonmarketinggroup.net
• Linkedin: https://www.linkedin.com/in/deryckrichardson