Interested in starting your own entrepreneurial journey in business development but unsure what to expect? Then read up on our interview with Matt Stephens, Owner of Chatham Oaks, located in Chatham, MA, USA.

What's your business, and who are your customers?

Chatham Oaks is a digital marketing business centered around small businesses with limited time and resources. Chatham Oaks clients are primarily businesses trying to break into developing a brand presence online but may not know the exact path they need to take to succeed.

We focus on using Search Engine Optimization, Email Marketing, and Marketing Automation to create customized, sustainable solutions for each client with the privilege of working.

Tell us about yourself

My background includes a BS in Management from Bentley University, where I focused on entrepreneurship. I have always wanted to build businesses of my own. After many small start-ups and failed businesses, I learned a lot.

For seven years, I devoted my time to learning a skill set that I knew could help me build the business I dreamed of. In this company, I could help small businesses excel and change the lives of the fantastic, passionate people behind them.

I spent these years working with small start-ups, multinational trade associations, and massive marketing corporations and assisting with the conception and planning of hundreds of businesses across different continents. These experiences drove me to an epiphany after seeing the disconnect between modern marketing companies and the small businesses that use them.

I noticed an issue in the education and assistance using the tools these marketing companies provide. Thousands of businesses employ these marketing tools, and a large portion of them give up before they see any benefit from these beneficial tools.

I am motivated every day, knowing what I built with the guidance I experienced over the years. A fantastic support system has dramatically affected the businesses and livelihoods of passionate people doing what they love. Growing this company means that I can go on to do the same for others, and that's extremely exciting for me.

What's your biggest accomplishment as a business owner?

I believe my most significant accomplishment has been joining the SCORE chapter of Cape Cod. SCORE is a section of the SBA that assistances hundreds of thousands of businesses each year with all aspects of their business.

I am a Subject Matter Expert within my chapter, which has allowed me to assist dozens of businesses in my local community and connected me to a fantastic network of people who have followed a similar path.

Being a part of this community that positively impacts hundreds of people's lives has been my greatest accomplishment, and I am honored to be part of that more extensive network.

What's one of the hardest things that come with being a business owner?

The hardest part for solo business owners, especially in the new digital age, is isolation. Running an online business from home is highly isolating and can take a toll on the mental state of anyone.

One of the things I am interested in providing in the future is a community and communication outlet for other solopreneurs and freelancers, which they can join to assist them with their business development in growth, called NightSwim Media.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Pick an idea you are passionate about that transcends the typical reasons to start a business (money, success, etc.). I like to mention one quote to many of my branding clients: "if you're selling something you're passionate about, it doesn't feel like sales." You'll also always maintain the motivation you had when you started.
  2. Invest heavily into only two marketing channels. Find out who your perfect customer is, and focus your time on two marketing channels. Focus on providing your customer value rather than trying to be everywhere at once. Your time is your most valuable resource, so don't waste it promoting your business where your perfect customer doesn't hang out.
  3. Before creating content, ensure you know how to target/position it to your target market. If you are creating content without first verifying people are searching the topic, you may be throwing a dart at a dart board in the dark with a blindfold on. You may hit the bullseye, but odds are you don't hit the board.

Is there anything else you'd like to share?

If you are a small business, please reach out to your local score chapter, especially if you are a one-man show. We are there to assist you, for free, with everything from marketing to financials to taxes. Join a workshop or find a mentor. Hope to see you there!

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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