#82: Six-Figure Freelancing: Embracing an Entrepreneurial Mindset, with Gresham Harkless

Today’s guest is Gresham Harkless, of Alexandria, Virginia. Gresham is the founder of CBNation and Blue 16 Media. CBNation is a business-to-business (B2B) brand. It helps people like you—CEOs, entrepreneurs and business owners—with resources and increasing your visibility. It includes blogs under CEO Blog Nation, as well as podcasts and videos.

Blue 16 Media is Gresham’s digital marketing agency. He provides digital marketing services, including web design and SEO, to small- and medium-sized businesses and organizations. Central to his marketing philosophy is: You are a media company. And that means you should be developing a marketing strategy to connect with your target and reach your goals.

Gresham has spent the past eight years or so as an entrepreneur. One of the lessons he learned along the way—as he headed toward his six-figure goal—was that he could not do everything at the same time. Brimming with ideas, he realized he needed to focus on what could make the most impact on his business.

He also learned that it’s important to be able to quickly pivot and adjust to situations, like the pandemic, to be a successful business owner. It’s helpful as a business owner to be comfortable trying new things, changing up your business, taking risks. Being resilient and having an entrepreneurial mindset is important during times of change and challenges.

Gresham struggles with one of the things he loves the most: being able to focus, when he has a lot of ideas and things he wants to develop. He handles that by taking a new big idea and breaking it down into a smaller idea that is more doable with the time and energy he has.

Gresham talks about not having a support system around him as he began to think about starting an entrepreneurial business. Sometimes loved ones won’t support your decision, and that can affect your confidence and self-worth. Connecting with an entrepreneurial community helped him realize his ideas and goals were possible.

Gresham has become more of a morning person as he gets older. He starts with some kind of movement in the morning, before taking his dog for a walk. Then, he has breakfast and does some sort kind of journaling or other writing. Next, he spends about two hours on lead generation for his business. After that, he blocks off about 10:30 a.m. to 4 p.m. for client work and client meetings. He ends his work day at about 5 or 6 p.m.; pre-pandemic that meant heading to the gym after work.

In the past, he would often work through lunch and not eat and also keep working late into the evening. He realized this was causing low energy and headaches, so he created the habit of going to the gym at the end of each work day.

Lack of support played into Gresham’s self-worth, which led him to undercut his pricing. He recommends trying to find out what the average rates are in your industry, but he also encourages people to realize the value they bring to clients.

Based on past salesperson experience, Gresham learned to provide three tiered project options to clients. He calls them Dominant (the above-and-beyond option), Competitive and Representative (the base option). That allowed him to take his biases out of what a potential client might choose and not undercut himself. He would sometimes be surprised at which clients picked the more expensive option, showing him that he might have been basing previous options and pricing on incorrect assumptions about a client.

This process also allows clients to choose Competitive or Representative but to move up to the next option at a later point, which provides a way to bring in more income. In addition, Gresham points out that if every client chooses the Dominant option, you know you are pricing yourself too low.

Gresham subcontracts with other independent contractors on a regular basis, not just project based. He tries to bring on experts in certain areas before he actually needs them. He will often start them on an internal project to test them out before they start on a client project. That allows him to learn about their work style and communication skills.

Gresham requires a deposit upfront, after being burned a few times and not getting paid. Plus, a deposit shows that a client is serious about moving forward. “Let me think about it” without a deposit often strings you along.

It’s also important to lay out the process for clients so they know what to expect from you and what the steps are throughout the project.

Gresham’s ideal clients are those who aren’t taking advantage of digital products, so he often focuses on meeting people in-person (or via Zoom, during the pandemic). That has also meant joining networking groups.

Gresham encourages entrepreneurs to follow their passions and keep moving forward and taking action.

Biz Bite: Use project management software (Basecamp, Asana)


Gresham’s primary website (where you can find links to all of his services and resources).

Blue 16 Media

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