From MLB pitcher to Wall Street: Ross Stripling's unconventional second act
Ross Stripling’s path from college baseball to Wall Street is anything but typical. After a nine-year career in Major League Baseball, he now runs a financial firm helping young athletes secure their futures. His journey began with a tough choice between education and professional sports—and an injury that changed everything. Stripling first made his mark at Texas A&M, where he walked onto the baseball team. While studying, he planned to earn a master’s in business finance. His talent on the field soon drew attention, and the Colorado Rockies offered him a six-figure bonus after his junior year. He turned it down.
After his senior year, he accepted a similar deal from the Los Angeles Dodgers. His professional career started in the minor leagues, but at 24, a severe elbow injury sidelined him after just one season. Despite the setback, he fought back and spent five seasons with the Dodgers, later pitching in the All-Star Game and the World Series. Even during his playing days, Stripling stayed close to finance. An internship introduced him to Matthew Houston, a mentor who admired his stock analysis reports. The two built a strong professional bond, exchanging messages about markets and clients up to 50 times a day over the past decade. Five years ago, Stripling founded Skyward Financial, a firm focused on financial planning for athletes. Now retired from baseball, he dedicates his time to teaching young players how to manage wealth and create lasting financial stability.
From a college walk-on to a World Series pitcher, Stripling’s career took unexpected turns. Today, he uses his experience in both sports and finance to guide others. His firm, Skyward Financial, continues to grow, offering athletes the tools to build generational wealth.
