Cole Milam, CFP®, MBA
Cole Milam, CFP®, MBA
Wealth Planner Manager

Education

Southern Illinois University – Master of Business Administration – Business Analytics
Southern Illinois University – Bachelor of Science in Business Administration and Finance
Jefferson College – Associate of Science in Mathematics



Professional

Cole’s professional journey began with an internship at a notable financial services firm in St. Louis. However, his career took an exciting turn when he was drafted by the prestigious Boston Red Sox, where he spent two years refining his skills as a pitcher. Following his time in professional baseball, Cole transitioned back to the financial services industry, bringing with him the discipline, perseverance, and teamwork that defined his athletic career.

Cole joined Gatewood Wealth Solutions as a Wealth Coordinator, playing a key role in supporting the firm’s advisory teams and contributing to clients’ financial plans. His dedication and expertise led to a promotion in July 2022 to Wealth Planner, marking a milestone for both his career and the firm, as he became the first team member to successfully transition from Wealth Coordinator to Wealth Planner—a testament to the firm’s commitment to career growth and development.

Now, as Wealth Planner Manager, Cole leads the firm’s financial planning team, striving to ensure that every client’s wealth strategy is meticulously crafted to align with their life goals. He plays a pivotal role in mentoring and training other Wealth Planners, refining processes to enhance efficiency, and maintaining the firm’s high standards of service. Cole collaborates closely with advisors to guide families through life’s key financial moments, helping them make informed decisions with confidence.

Beyond technical financial planning, Cole is dedicated to fostering a culture of excellence and innovation, helping ensure that Gatewood Wealth Solutions continues to provide tailored, forward-thinking strategies that empower clients to build wealth with purpose.
Cole is a Certified Financial Planner® (CFP®) professional, a designation that demonstrates his proficiency in financial planning, risk management, investment, tax efficiency, retirement, and estate planning advising.

Cole holds his Series 6, 63, 65 and 7 securities registrations with LPL Financial, as well as his Life and Health license.

 



Personal

Cole lives in O’Fallon, Illinois, with his fiancé, Kaycie Dresch. In his leisure time, Cole’s passion for baseball remains undimmed. For the past several years, he has channeled this drive into coaching, imparting his expertise and love for the game to aspiring players. His ambition motivated him to establish a dedicated pitching lab, mentoring athletes across a wide spectrum, from major league hopefuls to budding talents at the youth level. Beyond the diamond, Cole is an enthusiastic participant in various other sports and outdoor pursuits, maintaining an active and engaged lifestyle.

Testimonials

"Our relationship with Gatewood Wealth Solutions has evolved over the years right along with our family.  From building and protecting our wealth to retirement and estate planning, Gatewood has guided us and enabled our objectives. It’s assuring to know skilled professionals we trust are working with us to optimize what we have worked for all our lives. "

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Dr. Boyd C.
Retired Corporate Executive 11.13.23

"My wife and I have had the benefit of working with John Gatewood for over thirty-five years. Initially, John worked with us planning our personal and business life insurance needs. As his service offerings expanded, we took advantage of his expertise to help us with our family's financial planning. We could not be more pleased than what we are with the plan the Gatewood Wealth Solutions team developed for us. The team members are well-trained, intelligent, friendly, enthusiastic, and very good listeners. We have two scheduled reviews of the plan every year with one of the principals and at least…"

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Steve W.
Retired Business Owner 10.16.23

"My wife and I have known and worked with John Gatewood and his team for nearly a decade.  The values-driven team of Gatewood Wealth Solutions is motivated, caring, highly competent and personally fueled by character and integrity.  I recommended GWS to friends and family - including my children - because their deep desire to help clients "give purpose to their wealth" gives us all the opportunity to better serve our families and communities."

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Dave M.
Corporate Executive 09.19.23

"Navigating the complexities of my corporate life was already a challenge, but when my husband passed away, it felt like an insurmountable mountain of emotions and paperwork. The team at Gatewood Wealth Solutions stepped in with compassion, efficiency, and expertise, guiding me through the entire estate settlement process. Their unwavering support made a world of difference during such a challenging time. I am profoundly grateful for all they've done and continue to do for me. Their services are truly unparalleled, and I wholeheartedly trust and recommend them."

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Carol S.
Corporate Executive 09.20.23

"My wife and I became a client of Gatewood Wealth Solutions twelve years ago on the recommendation of a friend who was also a GWS client, and I am very glad that we did. Until that time, I had managed our 401(k) and investments, but with retirement on the horizon, we felt it important to get professional help for retirement planning and investment management. The Gatewood team developed an integrated financial and retirement plan we refined together. It was based on information such as our current financial position, desired retirement date and lifestyle, anticipated job and retirement income, expenses, and…"

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Phil P.
Retired Corporate Executive 09.20.23

"I have worked with Gatewood Wealth Solutions since its inception and could not speak more highly of my experience. Gatewood Wealth Solutions provides comprehensive wealth management services for my family in a very sophisticated way. Their planning services are comprehensive and consider all assets of our family, not just what they manage. This is important for our family since we have a real estate business which must be considered in our planning. They also help us with our estate and tax planning each year. Their service is exceptional and is proactive and not reactive. I have referred members of my…"

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Tim M.
Partner/Attorney 09.22.23

"I’ve been with Gatewood Wealth Solutions and its predecessor for 21 years as our financial advisors. I first met John Gatewood in 2002 when I purchased a life insurance policy from him when he was with Northwestern Mutual. Shortly after having additional discussions with John, we started using them as our only financial advisors. They continued over the years to more than perform above my expectations and also started to bring in additional talent within their organization in order expand and meet client’s expectations. Since they’ve organized as Gatewood Wealth Solution and separated from Northwestern Mutual, they’ve continued to add…"

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Joe H.
Retired Corporate Executive 09.25.23

"I have been with Gatewood Wealth Solution for seven years, and I would highly recommend them for wealth management services.  They are a small but very efficient, effective, knowledgeable team that provides highly personalized, client-centered services.  If I didn't know better, I would think that I am their only client!  They have an excellent working relationship with a highly respected law firm that provides assistance with trusts and estate planning.  They also have an excellent working relationship with a tax accounting firm.  All of this so that all aspects of my financial planning needs are seamlessly coordinated. Their quarterly meetings…"

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Susan H.
Corporate Executive 09.26.23

"Gatewood Wealth Solutions has been one of our best decisions we have made in the last five years. I have met with numerous financial planners who’ve all come to me with similar ideas and recommendations that don’t seem to prove that they are thinking outside the box for me individually. But when Gatewood Wealth Solutions came to me with their plan it was strategically designed with so many aspects taken into consideration that I was surprised at how uniquely competent and professional they were. They brought me many ideas and recommendations that would not bring them profit. They brought me…"

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Scott & Johanna S.
Business Owners 09.28.23

"Gatewood Wealth Solutions gives me confidence that my retirement savings are being monitored and managed with MY best interest in mind. All of the staff is welcoming, friendly and respectful. They have comprehensive knowledge of long-term financial planning, estate planning and tax planning. I have been with Gatewood for many years and hope to be with them for many more years to come."

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Gary B.
Corporate Executive 09.27.23

"I have known John Gatewood, the founder of Gatewood Wealth Solutions, for many years. We became friends well before we talked about business, and it was a natural decision to turn to John for help with our affairs when I needed it because I had grown to know and trust him. It really is true that John and his team at Gatewood Wealth Solutions are completely focused on helping ordinary families like ours to become financially independent. The family part especially means something: One day my 20-something son called to ask if I thought our group would be willing to…"

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Steve K.
Retired Corporate Executive 09.27.23

Testimonials Disclosure

The statements provided are testimonials by clients of the financial professional. The clients listed have not been paid or received any other compensation for making these statements. As a result, the client does not receive any material incentives or benefits for providing the testimonial. These views may not be representative of the views of other clients and are not indicative of future performance or success.