Ashlee Berghoff of A Squared Online

    We Spoke to Ashlee Berghoff of A Squared Online About How to Build a Successful Service Business

    As part of my series about the “5 Things You Need To Know To Create a Successful Service Business,” I had the pleasure of interviewing Ashlee Berghoff.

    Ashlee Berghoff, MBA, is the founder of A Squared Online. Her team helps lifestyle-driven entrepreneurs take back their freedom through powerful systems and effective delegation. As her clients conquer the freelancer-to-CEO transition, they can experience real momentum and confidently channel their energy into the things that matter most to them.

    Ashlee is the author of Eureka Results: How Entrepreneurs Can Turn Their Best Ideas Into Reality, which was published in April of 2021 by New Degree Press. Find her online at

    Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

    Unlike a lot of entrepreneurs, I didn’t grow up with an “entrepreneurial streak.” Most of my family owned their own businesses, but I expected to follow a more traditional career path. But in 2017, as I prepared to graduate with an MBA, I grew frustrated with the binary choice given to me: either I could pursue a management career, or I could leave it all behind to stay home with our children. I knew there had to be another choice. I wanted to pursue meaningful work while also having autonomy around the amount of time I was available at home.

    At the time, I was a project manager within a large consulting firm, and I began to wonder if small business owners needed someone like me. I left my job for a three-month experiment to see if I could make it work on my own, and I’ve never looked back.

    Not only is every family unique, but every life season is unique too. I’m grateful that entrepreneurship has given me the chance to make decisions about what is best for me and my family without external expectations. I’ve been able to design my work around what my children need, our goals as a family, and my own passions. I wouldn’t trade that freedom for anything.

    What was the “Aha Moment” that led you to think of the idea for your current company? Can you share that story with us?

    Eureka moments are great, but we often rely too heavily on them and discount the power of iterating towards a goal. My experience has been less about a specific ‘aha moment’ and more about trying something, learning from the experience, and making things better.

    I started my business as an independent business manager, which meant that I helped my clients — mainly online service providers like coaches and copywriters — get out of the weeds and make things happen in their businesses. They would come to me with problems, and I would magically make solutions happen.

    But my model had flaws. The endless scope made it difficult for me to build a team and get out of the weeds myself, and the lack of leverage placed a lid on my capacity to grow. Over time, I began to specialize in process improvement and systems design so I could leave administrative support behind and walk clients through a streamlined experience.

    My new focus solved a lot of problems, but it had problems of its own. Removing all the easier work left my team and I with a long list of challenging strategic problems to solve. Even with extra time to take on more clients, we didn’t have the mental bandwidth to expand endlessly in that direction. Our deepening specialization was also nudging our prices upwards, making us less affordable to the small service businesses we most wanted to serve.

    Now, we lead a group program that helps freelancers and small agencies leverage the power of systems and team building to achieve entrepreneurial freedom. The program has enabled us to keep a high-touch service but at a lower price, and our capacity to grow has multiplied. I’m thrilled about where we are today, but I know there will always be new horizons to pursue.

    Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

    I started my business right around the time that Europe passed its GDPR regulations. This new regulation was designed to limit spam emails and required businesses to implement a variety of changes, including clear opt-ins for people joining email lists. The rules were complicated, and articles were swarming everywhere about how to comply with these regulations.

    For some reason, I believed that I needed to spend time understanding these regulations. The fact that I didn’t live in Europe or have an email list didn’t register in my conscious mind. I don’t know how much time I threw down that rabbit hole, but it was way too much. Months later, I was surprised to find that many large companies had yet to bother with these changes. It was an important lesson for me: I needed to actively ignore anything that wasn’t my core vital need at that point. I would have been much better off networking with potential clients.

    Thank you for that. Let’s now pivot to the main focus of our interview. Extensive research suggests that “purpose driven business” are more successful in many areas. When you started your company what was your vision, your purpose?

    I wish I could say I started my business with a strong sense of larger purpose, but that would be a lie. I always wanted my work to contribute to the common good, but I initially saw my business mainly as a way to find freedom for myself.

    Like my strategy, my sense of purpose has developed over time with each season of the business. When I hired my first team member, I began to dream about what it might look like to not just create jobs, but to create great jobs. I wanted to provide the same opportunities for others that I sought for myself. As of writing this article, we are a team of five, which is thrilling to me.

    Later, as I developed a passion for the power of systems to transform lives and businesses, a broader vision began to take shape. Too many entrepreneurs are suffering under the weight of overwhelm and unfulfilled dreams. Most of us have never been taught how to use systems to make our best ideas happen, forcing us to rely on pure willpower. It’s like we’re all biking up a mountain when a car is available. I am on a mission to redefine what systems are, why they matter, and how we can use them. I want entrepreneurs to experience true freedom and bring their own visions to life. That mission inspired my first book, Eureka Results: How Entrepreneurs Can Turn Their Best Ideas into Reality.

    What do you do to articulate or demonstrate your company’s values to your employees and to your customers?

    We have three values within A Squared: one, cultivate shalom (peace, wholeness, and welfare); two, think differently and help our clients do the same; and three, make order out of chaos. These values are central to our core offers, which exist to bring order, peace, and relief to our clients. We want to help them get their lives back. We also want to go deeper than a surface-level process by helping our clients see their worlds, their businesses, and their time differently.

    Do you have a “number one principle” that guides you through the ups and downs of running a business?

    One of my favorite musicians is an artist named Lecrae. In his song ‘Fear,’ he wrote a line that stops me short every time I hear it. “Will I hear, ‘you care too much about all this stuff that really don’t matter / you chased the wind and you won it / climbed to the top of a two-foot ladder?’” As an entrepreneur, I’m tempted to focus on the wrong things or tie my worth to my business’ success. I don’t want to lose myself climbing to the top of a two-foot ladder.

    I’ve heard it said that the most compelling visions are bigger than what we can achieve in a lifetime. I want to contribute to a world where people can start a business for freedom and actually get that freedom. I want to see an economy with a much broader sense of what it means to contribute. We’re so tied into the ‘9–5 until you’re 65’ mindset that we can struggle to see beyond that. Our world will become better when our economy creates space for all of us to have endless opportunities to create, contribute, and build a life. When I think about that vision, my own ups and downs seem a little less scary.

    Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

    I don’t think I could limit the ‘hard times’ to when I first started my journey. It’s not a past tense thing for me. I’m not a daredevil by nature, and I’d much rather experience a steady upward climb than the roller coaster of real entrepreneurship. My highest highs (like receiving a book endorsement from one of my heroes) and lowest lows (like losing a client) have often shared the same 24-hour period of time.

    The other day, one of my favorite entrepreneurs on earth posted a full-time job opportunity. Reading the description, it was my dream job in every way. It also happened to pay four times as much as I take home from my business. I felt the pain of what I gave up by starting this business. Then, I turned my attention to what I had chosen instead. The chance to build something of my own. The jobs that didn’t exist before. How much I’ve learned. The fact that I spend so much time with my daughter that she needs a break from me sometimes. And it’s worth it all.

    So, how are things going today? How did your values lead to your eventual success?

    I don’t believe that arrival exists, so I’m not going to tell you that I have arrived. But when I remember where I was a year ago, I see how far we’ve come as a business. I’ve had to learn how to define my vision, communicate it clearly, and identify the best model for serving our clients, but we’re so much stronger in those areas today.

    I’ve learned to practice what I preach by designing this business around my deepest values. I’m confident that A Squared’s existence benefits our team, customers, industry, and families. We have plenty to figure out, but I am grateful for where we are today.

    Based on your experience and success, what are the five most important things a founder or CEO should know in order to create a very successful service based business? Please share a story or an example for each.

    None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

    I dedicated my book, Eureka Results, to three groups. One was my family, whose entrepreneurial spirit always inspires me. Another was Pizza Hut: I give them credit for turning me into a reader by bribing me with free pizza through their BOOK IT! Program.

    My third dedication was to my mentor, Pat Henriques, who passed away last year. Pat always pushed me to dream bigger. She believed in me so fiercely that I had no choice but to believe in myself when she was around.

    I met Pat Henriques when she was serving as an Entrepreneur in Residence at Georgetown. Pat had built and sold a very successful service business, so I gravitated to her immediately. We met often to chat about my new business. She knew exactly how to call me out when I was thinking small; it was almost like my self doubt made her angry because she saw something in me.

    Before I moved away, Pat and I grabbed lunch at a Greek restaurant, and I remember thinking how grateful I was for her. I was in awe of her as an entrepreneur and a woman, and I was so excited to someday tell her that her faith in me paid off. I almost took for granted that one day I’d fly back to DC, invite her back to that restaurant, and tell her I’d finally made it…I’d become the entrepreneur she insisted I could be. She was a true mentor to me, and a friend.

    You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

    I would love to start a movement of people on a journey towards time leadership together. I stopped using the phrase “time management” because it makes us all think of productivity tricks and planners. Time leadership is so much broader than that. Too many of us are running ragged because we don’t realize we have a choice. We’re missing the things that matter most to us, frantically reacting to an endless deluge of inputs and expectations. We have the chance to step into a leadership role in our own lives, channel our time towards our deepest values, and release toxic pressure, perfectionism, and workaholism. They’re not easy to give up, and we need each other.

    How can our readers follow you on social media?

    You can find me on LinkedInFacebook, and Instagram.