We were lucky to catch up with Christopher Dennis recently and have shared our conversation below.
Hi Christopher, so happy to have you with us today and there is so much we want to ask you about. So many of us go through similar pain points throughout our journeys and so hearing about how others developed certain skills or qualities that we are struggling with can be helpful. Along those lines, we’d love to hear from you about how you developed your ability to take risk?
I grew up in a family of non-risk takers, so risk was something I was always apprehensive about. However, everything changed when my fiancé, Nicole, became pregnant with our daughter, Delilah. I realized I was stepping into a new chapter of my life and had a pivotal choice to make: continue the legacy of avoiding risks or break that cycle for the sake of the next generation. My family became the driving force behind my willingness to embrace risk.
Coming from a modest background, I didn’t have the advantages of wealth or financial security, but I wanted to create something more for my family—freedom, generational wealth, and the ability to achieve our dreams. I knew that to reach those goals, taking risks was essential, even if it meant facing the possibility of failure. Overcoming fear is the first step toward developing the ability to take risks. The second is identifying who you’re taking those risks for—whether it’s for yourself, your family, or a greater cause.
The first major risk I took was starting a digital marketing company with my fiancé, Nicole, and two close friends and former colleagues, Sam Maugans and Chris Shirlow. The second was leaving my secure full-time position as a web developer to dedicate myself entirely to our business. This journey has been both challenging and rewarding. I’ve learned a great deal and have continued to strengthen my risk-taking abilities. While risk can bring success and substantial rewards, it also brings fear and the possibility of failure. I’ve learned to embrace that fear, accept failure as part of the process, and am proud of the personal growth I’ve experienced along the way.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?
At the age of 12, I discovered my passion for web development. I began by teaching myself how to code HTML and CSS, experimenting on platforms like MySpace (an early social media platform) and Neopets (a popular browser-based game from the early 2000s). However, it wasn’t until I was 28 that I secured my first professional web developer position. Between 19 and 28, I worked in various corporate roles—ranging from data management to customer service and technology support. These positions provided me with invaluable experience, particularly in understanding the social and political dynamics of corporate life.
By 2021, I had landed a web developer role at the same marketing agency where I met my business partners and life partner, Nicole. My leadership and communication skills, honed over years in prior roles, quickly propelled me to the position of Director of Web Development. While we gained valuable experience, agency life didn’t align with our vision. We eventually all left to pursue freelance careers in our respective fields. I transitioned to a new agency as a Senior Web Developer.
Our paths crossed again when we ended up freelancing for the same client. What started as one freelance gig evolved into what is now FourHorse Digital LLC. We realized that each of us excelled in our areas of expertise, and forming a business together was a natural next step. Today, FourHorse Digital serves nine incredible clients and continues to grow at a steady pace. Although we’ve only been in business for about a year, our results for clients have been exceptional.
While I oversee web development and web design, FourHorse Digital offers a wide range of services, including content writing, SEO and technical SEO, PPC/LSA campaigns, and social media management. We don’t consider ourselves a traditional “agency”—that’s a term we avoid. Instead, we position ourselves as an in-house marketing team for our clients, providing them with the high-level attention and communication they deserve.
Current Promotions from FourHorse Digital:
We are offering free audits of business websites, SEO health, and PPC campaigns—whether or not you decide to work with us.
We are also offering free website builds to businesses who sign up for our Tier 2 or Tier 3 packages. More on our packages can be found here: https://fourhorsedigital.com/marketing-packages
Additionally, we offer referral payouts to anyone who refers a business to us that signs up!
At FourHorse Digital, we operate with no contract commitments; all of our clients are on a month-to-month basis.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
This is a fantastic question that every new or aspiring business owner grapples with.
Interestingly, just a few years ago, I would have told you I wasn’t in a position to answer it – which leads me to the first critical quality for any business owner: confidence. You must have confidence in your abilities, confidence in selling yourself and your business, and confidence not just in your successes but in your failures as well. It’s my confidence in myself and my craft that has brought me to where I am today. Confidence helps you overcome fear and imposter syndrome, ignore doubters, and fight for what you want in life.
The second key to my journey has been the (often overlooked) skill of communication. Knowing what to say, when to say it, and how to say it is an art form. Equally important is the ability to adapt and tailor your communication to different personalities you encounter. This adaptability is crucial in business, as it helps you build relationships, sell yourself, and sell your business. Effective communication is non-negotiable if you want to succeed in your business endeavors. My advice? Practice daily. Read books, watch YouTube videos, take speech classes, and apply what you learn to everyday situations. The ability to communicate effectively will be one of your most valuable assets.
Lastly, the third lesson I’ve learned is that nobody really knows what they’re doing—and that’s okay. You’re not alone in feeling uncertain. I often compare it to childhood: as a kid, you assume adults have everything figured out, only to become an adult and realize everyone is still learning. When we started our business, we had no prior knowledge of how to run one. We learned through research, trial and error, and we continue learning every day. Business is an ongoing journey of growth, especially as the economy and other external factors evolve. Don’t let the fear of not knowing stop you from starting a business. You’ll figure it out along the way. And this brings us full circle to the first essential quality: confidence. Believe in yourself, and you will succeed, have confidence that you CAN do it and you WILL do it.

Who is your ideal client or what sort of characteristics would make someone an ideal client for you?
Our ideal clients at FourHorse Digital are small business owners looking to grow their business and generate more revenue. Maybe this is a client that has never done marketing before, or someone who is sick of the bare bones marketing they are getting from their current marketing company.
Our clients can be as hands-on or hands-off with the marketing as they want to be, as long as they are communicative and responsive – yes, we work FOR our clients, but also work WITH out clients to achieve their goals.
We have all worked in almost every vertical you can think of, so no type of business is off limits to us! Currently we hold a client base of verticals such as HVAC, Roofing, Home/Business Cleaning, Landscaping, Finance, eCommerce, among others!
Contact Info:
- Website: https://fourhorsedigital.com
- Instagram: https://instagram.com/fourhorsedigital

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