Any lessons learned that you would like to share?

In every industry, including financial services, the landscape is constantly evolving with changing rules, regulations, acquisitions, and sales. Being client-centric and staying informed and adaptable are key factors in successfully navigating these changes. For instance, during the financial crisis, I worked for a company that was acquired, and being nimble and client-focused allowed us to handle that transition effectively, demonstrating that these qualities are essential in managing any shifts or challenges that arise in business.

Our media company’s motto is, “Where aha meets oh shit.” Tell us about your biggest aha moments.

One of my most memorable "aha" moments occurred during my first founder transition project, where we engaged a local charity, other employees, and the entire team to create a solution benefiting both the community and the employees. This experience deeply resonated with me and piqued my interest in succession planning. As an engineer, I appreciate challenging problem-solving opportunities, and succession planning, with its complexity, presented an engaging and enjoyable challenge. I realized that it's a fulfilling way to assist all stakeholders involved.

Tell us about your biggest oh shit moments.

I have two.

The first is from my time as a flight instructor in Indianapolis. I engaged in a venture to purchase an airport with a buying group, developing a business plan and securing financing. However, upon closer examination of the numbers, I couldn't see a profitable path, especially considering the debt involved. It just wasn’t a good business opportunity in the long run. So, despite the allure of owning an airport at the age of 22, I decided to pass on the opportunity.

This turned out to be a wise choice because shortly afterward, the person providing the financing, who happened to be a former student of mine, embezzled $2 million from his company and fled the country. This experience taught me two valuable lessons: to 

thoroughly research those I do business with and to never let emotions cloud sound decision-making.

The second happened after I got into finance. I initially started a business in Charleston called Atlantic Strategic Business Planning, franchising from a group in Greenwich, Connecticut consisting of a CPA, a tax attorney, and an insurance expert. Our business model involved providing technical and marketing support for a local accounting firm. We were highly successful until changes in CPA regulations allowed them to start accepting commissions. Our client patted us on the head and said, “We really appreciate all your help, but we got it from here.” That’s when I learned how to pivot whenever rules start changing.

Do you have a personal mantra or motto?

I adhere strongly to the Golden Rule. That is, treating everyone, regardless of their position, the way I'd like to be treated. It's a universal concept, and I believe strongly in its value. Additionally, a phrase I've passed on to my 18-year-old son, inspired by Tony Horton, is "try your best and forget the rest," which underscores the importance of giving your all in everything you do.

If you could hit rewind, is there anything you would do differently?

Looking back, I realize that, despite being well-trained in the field, I lacked confidence in my ability to communicate effectively with people. I had plenty of confidence as a pilot and an engineer, but I was missing it in the financial world.

This lack of confidence, possibly compounded by imposter syndrome and the age gap with clients, made me doubt my expertise. I often felt like I was missing something crucial, which led me to undervalue my own capabilities. Looking back, I see that the financial plans I created in my mid-twenties were remarkably sophisticated, but my confidence struggles prevented me from fully embracing entrepreneurship at that time. Instead, I ended up working for a consulting firm, which, while a valuable experience, delayed my journey as an independent business owner, where I could have built my client base and taken more entrepreneurial initiatives.

Did you have any “game-changing” resources or tools that helped you start or grow? Why was that resource a game-changer for you?

A game-changing factor in my career was the presence of exceptional mentors. When I began my journey in the business world, I rapidly developed my skills because I aligned myself with incredibly intelligent and successful individuals in Greenwich who were at the forefront of tax strategies and innovations. Being exposed to their expertise and insights was like drinking from a firehose of knowledge and significantly shaped my professional growth.

As far as current resources go, large language models and AI are undeniably game-changing technologies, and we fully integrate them into our practice. In today's business landscape, especially in service-based industries like ours, incorporating AI is not just a communication tool but a valuable resource for leveraging time and efficiency. While it can handle many tasks, it's important to recognize that AI, much like a knowledgeable but inexperienced college graduate, lacks the wisdom for nuanced decision-making. However, by using it to perform routine tasks and make minor corrections, businesses can save significant time and effort.

Thinking about the local entrepreneurial community or ecosystem, what do you believe is working well? What do you think is missing or a gap that needs to be filled?

The entrepreneurial ecosystem in Charleston has witnessed remarkable growth and development over the years, with various organizations and initiatives contributing to its success. Entities like the Harbor Entrepreneur Center and the city's business incubator have played pivotal roles.

Additionally, private equity firms and angel investment groups such as Charleston Angel Partners, Venture

South, and the South Carolina Research Authority have become valuable resources, providing both talent and capital to entrepreneurs in the region. This transformation from a Navy-centric town to a thriving hub for startups and businesses highlights the remarkable progress made over the past decade, making Charleston an attractive place for aspiring entrepreneurs to establish their ventures.

While Charleston's entrepreneurial ecosystem has made significant progress, one missing element is time for further development. Although Charleston may not be as large as Austin or the research triangle in North Carolina, it's rapidly growing and catching up, notably in terms of business expansion. What the region requires to continue its growth are more substantial, successful exits. Companies like Blackbaud® and Benefitfocus® have had significant exits, leading to the emergence of spin-off ventures and the development of tech innovation in the area, ultimately contributing to Charleston's tech ecosystem.

What do you want your company to look like a year from now – from the market, your product or service, your team or people, the culture, or revenue – describe how you would like things to look a year or two from now. What have you put in place – or are going to put in place – to make that a reality?

Our goal is to maintain steady and meaningful growth while focusing on acquiring the right kind of clients – those who are big-hearted and align with our values. Instead of simply pursuing the most successful clients, we prioritize quality and character. To support this growth, we recognize the need for additional service resources, and we're actively in the process of hiring. The talent we've interviewed has been exceptional, and we're excited to bring in someone who can contribute as a rock star and introduce us to fresh perspectives, technology, and strategies.