Drew Watson’s journey to becoming Kentucky’s top financial advisor didn’t start with spreadsheets and stock portfolios — it started with a lawnmower and a doctor’s advice. As a young man pursuing medical school, Watson mowed lawns and built relationships with clients who valued trust and dependability. One of them, a doctor whose mother’s yard Watson mowed, suggested he pursue financial advising instead of medicine. That advice, combined with Watson’s natural ability to connect with people, set him on a path that has led to national recognition.
Today, Watson is the CEO of Align Wealth Management with Ameriprise Financial in Owensboro. And for the second consecutive year, he has been named the top financial advisor in Kentucky by Barron’s, a publication covering business and finance. The annual “Barron’s Top 1,200 Financial Advisors” list recognizes outstanding professionals based on assets under management, revenue produced for the firm, regulatory record, and overall quality of practice.
For Watson, the honor is more than just a ranking — it’s a validation of the dedication he and his team bring to their clients every day.
“Personally, we strive to give our clients the best experience they can get, treat our team members like they’re solid gold, and then let the results speak for themselves,” Watson said. “It’s always great to be vindicated by the metrics, but our focus has always been on the client experience and providing true financial planning.”
Watson said financial advising is more than a job — it’s a calling.
“This is a vocation for me,” he said. “Just like a physician is on call for emergencies, I treat my role the same way. Clients trust us with their financial futures, and that responsibility is something we take very seriously.”
His firm takes a comprehensive, holistic approach to financial planning.
“A lot of people may say they do financial planning, but as I always tell clients, if you’re not paying for it, you’re really not getting it,” he said. “We focus on everything — retirement projections, estate planning, setting up retirement income strategies. Investments are just one piece of the puzzle.”
Watson’s career path wasn’t always clear. Initially, he planned to go into medicine, taking rigorous coursework at the University of Notre Dame. But one of the doctors saw a different path for him.
“He told me, ‘Medicine is going to be too much corporate. If you really want to help people, you should look into investments.’ That stuck with me,” Watson said. “I changed course midway through school, and I’ve never looked back.”
Starting out in the industry wasn’t easy. Watson co-founded his firm in a single office with just one telephone in the Cigar Factory Mall.
“Not being from Owensboro, I had to basically start from scratch,” he said. “It’s the classic success story — if it’s tough in the beginning, it gets easier down the road.”
Today, Align Wealth Management has locations in three states, multiple advisors, and a growing team of financial professionals. Despite its growth, Watson emphasizes that the firm remains rooted in strong personal relationships.
“We have a very loyal and long-standing client base,” he said. “We’re now working with multi-generational families — helping not just the parents, but their kids and grandkids. Seeing those relationships come full circle is incredibly rewarding.”
Though Barron’s recognizes Watson individually, he credits his team for the firm’s success.
“This is a team effort,” he said. “Earlier this year, our team was recognized as one of the top teams in Kentucky, and just recently, we received a top Ameriprise award. That’s a big deal for everyone involved.”
Watson said his firm takes pride in its collaborative approach, ensuring that clients benefit from a variety of expertise.
“Our clients know that in most meetings, they’re going to be working with more than just me,” he said. “We bring in specialists who can offer different perspectives, and that’s a huge advantage.”
Looking ahead, Watson sees continued growth on the horizon.
“We’re expanding our team with younger advisors who are incredibly smart and hardworking,” he said. “We have recruits from the Vanderbilt MBA program, public accounting, and private equity. We want our advisors to develop their own styles because the more comfortable they are, the better the experience for clients.”
Despite his decades in the industry, Watson has no plans to slow down.
“I love what I do,” he said. “As long as my health holds up, I plan to keep doing this for a long time.”
For more information, contact Align Wealth Management at 270-684-8424 or explore their services online.
