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Inspiring Conversations with Andrew (Drew) Stipp of First Command

Today we’d like to introduce you to Andrew (Drew) Stipp.

Hi Andrew (Drew), thanks for joining us today. We’d love for you to start by introducing yourself.
I joined First Command Financial Services as a Financial Advisor in June 2024, following a 21-year career in the United States Army, where I attained and retired at the rank of Lieutenant Colonel.

My path into the Army was, like many, the direct byproduct of the terrorist attacks on September 11, 2001. I was pursuing my undergraduate degree at Purdue University when 9-11 happened; I distinctly remember where I was on campus on that awful day. My best friend joined the Indiana National Guard in October 2000, my brother joined the Army right out of high school in 2002, and I felt compelled to do my part in support of the Global War on Terror following my graduation in May 2003. We aren’t the greatest generation, but I like to think we represented the greatest of OUR generation.

I deployed a total of five times during my career: twice to Afghanistan (2005, 20019), Iraq (2008, 2010), and Jordan (2015). My wife, Jenn Stipp, was married to me for four out of five of those deployments – her love, courage, and support were paramount to my ability to conduct my assigned missions.

Alas, all good (and not-so-good) things come to an end! I was recruited by First Command prior to my military retirement; the company sought me out for planning and leadership skills on behalf of future clients and their financial security. Through the licensing and onboarding phases of my new career, it became clear that being a Financial Advisor/Coach for both military and civilian clients was the absolute right calling for me!

I also leverage my experience and focus on improving people’s lives and capabilities by coaching at Down Home CrossFit in Pooler. Jenn (a coach and personal trainer) and I have been members for almost four years now, and we welcome the opportunity to help others improve their physical capabilities in whatever way we can!

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
“The obstacle becomes the way” in the words of Marcus Aurelius – how true that is! My path to becoming a Financial Advisor started with earning the Series 7 and Series 66 licenses as well as Georgia-based insurance licenses for life, health, variable, and long-term care products. I poured myself into the study and pre-testing to feel confident taking on those rigorous exams.

During official onboarding, I became quickly accustomed to the fact that this is – first and foremost – a PEOPLE business that involves financial planning. Money is a sensitive and often taboo subject; many clients who could benefit from our services do not want to take that difficult “first step” in seeking outside analysis and support in looking at their financial situation.

That stated, I have had long days, nights, working weekends, “no shows” and “ghosting” for appointments and client contacts, and just about anything else you can think of. I have had meetings go perfectly smooth between couples, and I have seen couples almost deteriorate before I provided much needed outside perspective and guidance. The feeling of knowing I have leveraged my perspective and planning skills to set more favorable conditions for a client’s financial future is immeasurable – I wholeheartedly welcome all those aforementioned obstacles in my road because they become the way!

As you know, we’re big fans of First Command. For our readers who might not be as familiar what can you tell them about the brand?
The company now known as First Command was established in 1958 by Lieutenant Colonel (Ret) Carroll Payne (USAF). He served in conflicts abroad, such as Guam in World War II, and he saw first-hand the impacts of losing loved ones on families during that time. He committed his life after his service to our nation to creating a company that could advise and coach others in their financial journey with hopes of mitigating risks associated with (a) the untimely passing of a loved one and/or (b) outliving one’s retirement savings and income streams.

First Command offers a comprehensive set of financial planning products and services, including banking, investments, insurance, and retirement planning. More than 600 First Command Financial Advisors in more than 170 offices across the country and abroad are committed to the company’s Mission of “Coaching those who serve in their pursuit of financial security.”

I understand the challenges and opportunities associated with life in the military and civilian sector, and I am committed to helping service members, veterans, civilians, and their families get their financial lives squared away! I am currently licensed in the states of Alabama, Georgia, Florida, South Carolina, North Carolina, Virginia, Louisiana, and Illinois; I specialize in the following key areas:
 Comprehensive financial planning

 Retirement income planning

 Investment strategies

 Risk management (survivability, long-term care)

I empathize with the concerns that many may have about working with a financial advisor for the first time – my primary role is to create a comfortable environment for clients to establish their goals, understand their current financial behaviors, and to improve/optimize those behaviors with the intent on achieving their goals! I am a fiduciary and only create financial plans that are within the clients’ best interest. I serve my clients – much like I served the United States while wearing the uniform – as their trusted advisor and accountability partner, one that understands the importance of adjusting the plan as life events may necessitate.

Where do you see things going in the next 5-10 years?
I believe that finance industry will certainly continue to change in how we leverage technology to connect with clients. Notwithstanding, I predict that the human element in the client relationship will ALWAYS be relevant.

Experience has taught me that the #1 most potent and lasting form of leadership is BY EXAMPLE. Artificial Intelligence (AI) platforms may provide relevant and accurate financial data and/or information, but no AI platform will ever have the human domain of experience, and the empathetic connection that comes with living through the highs and lows of life (much like market cycles).

My hope and intent are to continue to connect with clients and be that trusted advisor who has lived through – and stayed invested through – so many highs and lows. My testimony is that successful people are defined by their resilience and ability to adapt as time and circumstances continue to change. I am proud and humbled by the number of clients I have helped thus far, and look forward to helping many more people, military and civilian alike, in the future!

Pricing:

  • Consultation Fee = $0
  • Planning Fee = $0
  • Investment Fees = Vary By Product/Plan

Contact Info:

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