2025 Men of the Year: Andy Drennen

Andy Drennen, vice president and senior portfolio manager at Simmons Bank, is invested in his clients and community. His team manages $1.7 billion in assets across two portfolios: the Core Equity Portfolio, Simmon’s flagship individual stock portfolio; and the Sustainable Impact Portfolio, which includes stocks involving environmental, social and governance risks. The two portfolios are available for Simmons managers to utilize with clients across six states.

His life has been a long journey, Drennen says, and is one he hopes will inspire others: “Eleven years ago, after failed business ventures, I found myself divorced, on unemployment and standing in the food stamp line questioning my abilities. My determination, refusal to accept a mediocre life and support from some very special people got me where I am.”

Drennen graduated from Drury University with an associate degree in business management and a bachelor’s in business administration. In 2018, he earned a master’s in financial planning from the College for Financial Planning. He is a certified financial planner and has completed master planner advanced studies. He has been published in the Kansas City Star, Yahoo News, AOL.com and is a regular Springfield Business Journal financial columnist.

Last year, Drennen and a friend co-founded State For Springfield, a volunteer task force and donor-advised fund hosted by the Community Foundation of the Ozarks, where he serves on the investment advisory board. The goal of the organization is to address needs that may not be addressed by larger financial funding avenues.

“The concept started with the two of us doing random acts of kindness on our own,” he says. “We soon recognized that we shared a passion for empowering others.”

Their projects have included providing hygiene items and monetary donations to Foster Adopt Connect Inc’s YouthConnect Center; collecting 10,000 back-to-school items and additional monetary donations to four Title-I elementary schools; and gathering more than 200 toys and $7,000 in donations for Isabel’s House Foundation and Harmony House during a December toy drive.

Drennen is proud to have served on the board of the Springfield Sister Cities Association from 2016 to 2022, including as president for two years. He developed the Kay Finnie Scholarship Fund and organized the first visit to Tlaquepaque, Mexico, for Day of the Dead, bringing American and Mexican young professionals together. Drennan grew up in Paraguay and said he is passionate about using his experience and knowledge to create international connections.

“I felt that my linguistic skills and similar cultural background could add value to the organization and people they serve,” he says. “I made some great friends, helped beautify our city and positively impacted the lives of thousands along the way. … There is a great need and opportunity for Springfield to promote tolerance and cultural diversity and I believe that Sister Cities has the connections to make it happen.”

Family: My wife, Lori, and I have two fur kids, Milo the Magnificent Show Dog and Sky Cat.

Words to live by: The cost of inaction could be greater than taking the risk.

Strange-but-true fact: I drink a lot of tea. So much so that I started my own tea company six years ago called Blend For That.

Advice to other men: To get something you’ve never had you must do something you’ve never done.