Before Josh Wingerd was helping clients understand insurance coverage, he was chasing a very different goal. Growing up, baseball was everything to him. It was more than a sport. It was how he saw himself, and by high school, he knew he wanted to play professionally. He first proved himself at Pima Community College in Tucson, Arizona, then continued at the University of Kansas before signing with the St. Louis Cardinals organization. Playing professional baseball was, as Wingerd describes, surreal. “I was living out the dreams I had as a kid and getting to compete against the most talented baseball players in the world,” he said.
His time in the game also taught him lessons he still applies every day as the owner of Farmers Insurance, Wingerd Agency L.L.C. Work ethic, adaptability and mental toughness all carried over from the baseball field into business. “If you are not 15 minutes early, you are late,” Wingerd said. “Do the hard things that no one else will do. What you do when no one is watching is what separates people.” Baseball also taught him how to handle situations that do not go as planned. As a pitcher, Wingerd learned to focus on what was directly in front of him rather than dwelling on the last play. “You have to live life one pitch at a time,” he said. “I use the motto W.I.N., What’s Important Now? Just handle the situation in front of me.”
That mindset influences the way he runs his agency. While Wingerd has to plan for the future, he encourages his staff to focus on what needs to be accomplished today. “I want us to be the best, and we talk about how to win the day every day,” he said. “The best ability is availability. You have to show up and be on time every day.”
Wingerd did not move directly from professional baseball into insurance. After retiring from the game in 2000, he sold cars before moving into real estate and mortgages. He opened his insurance agency in 2024. “I never really saw myself selling insurance,” he said. “I do have a passion for helping people, so that is probably why I went from auto sales to homes, mortgages and insurance.” Owning a business was also important to him. Wingerd enjoys building something of his own, but he also sees the opportunity to create jobs and help others reach their goals as one of the most rewarding parts of agency ownership.
At the center of his approach is education. Insurance can be complicated, and Wingerd believes an agent's job goes beyond simply finding a policy at a certain price. “My role as an agent is to explain coverages, what they do and why you need them,” he said. “Nobody likes to pay for insurance, but when they need it, they are glad they have it.” That is particularly important when it comes to comparing policies. Wingerd said the cheapest option is not necessarily the best one if it leaves gaps in coverage. “We have turned down business if someone wants a cheap policy with limited coverage,” he said. “We take the time to understand their situation and counsel them on the coverage needed and why.”
He encourages customers to ask more than just how much a policy costs. Instead, he believes they should start by asking what coverage is appropriate for their specific situation. “No two situations are the same, and the coverage should be different between them,” he said. Wingerd also wants clients to understand their policies before they have a claim. He recommends calling an agent before making decisions following an accident or damage to a home. “We have had clients start working on things prior to filing the claim, and now we can't prove what damage occurred that would have been covered versus man-made damage,” he said.
Customer service is another major focus at Wingerd Agency. The office has staff members whose responsibility includes reaching out to clients when policies renew. Auto policies, for example, renew every six months, giving the agency an opportunity to regularly check in with customers. “We want them to feel like they are talking to people that truly care about them and their families,” Wingerd said. “Nobody is just a number to us.” That personal attention can also make a difference when something on a client's record does not look right. Wingerd said the agency has helped clients track down police reports when accidents were incorrectly listed as at-fault incidents.
Outside of work, Wingerd's focus shifts to his family. “My family is everything,” he said. “I want to enjoy time with them doing what they love to do. That is rewarding.” He is also proud of the team he has built at Wingerd Agency. “I can't do this on my own, and we have a tremendous team,” he said. “Our office culture is great.”
There may not be a championship season in business, Wingerd said, but he still approaches each day with the same competitive mindset he brought to baseball. “It’s life, so you have to win every day,” he said. “It doesn't always happen, but that is the goal. There is no offseason.” For Wingerd, the lessons from baseball still apply. Be prepared. Adapt when things change. Focus on what is in front of you. And keep showing up.
In baseball and in business, he said, the goal is the same: be ready for whatever comes next.