It’s a bit ironic, really, that in the ultimate individual game and a profession that demands selfish commitment, Woodland has succeeded with and because of others, trusting them to help guide his life on and off the golf course. That’s why he signed with Mark Steinberg of Excel Sports Management to manage his career, and it’s what led him to David Miller of Auctus Advisors. This team, along with Dan Warren of Elliott Davis, has assisted Woodland in navigating the transition from working as a professional golfer to being the leader of his expanding personal enterprise.

The business of golf doesn’t end after the completion of play each week; it’s at the center of an umbrella that covers Woodland and his growing family, turning his success on the PGA Tour into a portfolio of investments that can ultimately touch and help others. “Trust and experience, that’s a huge deal to me,” Woodland says.

If winning the U.S. Open at Pebble Beach was the consummate achievement for Woodland, it was one part of a process that began long ago and will continue into the future. The moment captured by cameras and beamed around the world showing Woodland punching the cool air on the final hole at Pebble Beach changed so much. It added “major champion” beside his name, golf’s version of being knighted, and its effect endures for years. It didn’t, however, change Woodland.

“You treat people the right way,” Woodland says. “You treat people the way you want to be treated. It’s amazing what a smile or a ‘hi’ does for somebody sometimes. It’s pretty simple stuff, but it goes a long way.”

This straightforward, no-frills approach is the foundation of how Woodland and his advisors operate. This philosophy is encapsulated in five core values that Warren and employees at every level of his firm subscribe to:

  • Do the right thing.
  • Service to others.
  • Mutual respect.
  • Always getting better.
  • Quality.

In some ways, it’s as simple as Woodland’s reaction to winning the U.S. Open. “The reason we love to work with him is he has the mentality that it was the first of many,” Miller says. “Like, ‘I’m really happy I won. It’s an amazing milestone, but it’s one milestone.’ That’s the mentality we expect from him—like he scored a touchdown and handed the ball to the official.”

Similar to most world-class athletes, Woodland set out with his focus solely on what he could achieve. Creating a personal business and learning how to manage that aspect of his life came later. His mother, Linda, worked at a Kansas bank for more than 40 years. His father, Dan, is an electrical contractor. Woodland fits the classic image of a Midwesterner, born and raised in Topeka, Kansas. He’s quiet, solid, and self-sufficient.

“I would agree with that [description],” Woodland notes. “I don’t eat seafood—I’m from a place that’s far from the water, so a lot of steak and potatoes growing up.”

Since he was raised in a state where basketball is revered, it should come as little surprise that Woodland imagined himself one day playing professionally. He was a good player, good enough to attend Washburn University in Kansas on a basketball scholarship. But when Woodland found himself playing against the University of Kansas Jayhawks in historic Allen Fieldhouse, he realized he was in over his head. “I knew this wasn’t going to work,” he recounts.

Woodland left basketball and Washburn, transferring to Kansas, where he played golf, realizing that his opportunity lay in that sport. With a streak of toughness that runs through him, Woodland patiently finished his college eligibility, then turned professional and set out to build a career that has evolved like a sunrise, reaching full glow at Pebble Beach.

Along the way, Woodland established relationships that have helped his résumé and his portfolio flourish. He doesn’t reach for every shiny opportunity, preferring to take his time with decisions big and small, relying on the people he trusts to help him.

On the golf side, Woodland turned to Steinberg, who has been Tiger Woods’s agent since 1998. Steinberg gave Woodland simple advice when they connected: Play well and let him handle the rest.

What Steinberg doesn’t take care of, Miller and his group do. “Steiny brings in the money, and they handle the money,” Woodland says. “David has been a huge part. I’ve been with him since 2011. He’s been huge for me. He does all my real estate, he does everything. It’s nice to have him and Steiny work together.”

While Woods is the ultimate example of becoming a brand beyond the game he has dominated, he’s also broadened the opportunity for others. Woods took what Arnold Palmer and Jack Nicklaus did before him and expanded it, opening avenues that didn’t previously exist and pulling along his fellow professionals in the process.

Woodland is one of the beneficiaries. And as his career has blossomed, the four-time PGA Tour winner has had to view himself as a business, not just a golfer. “I had to learn it, to be honest,” he says.

To ensure that their business relationship remains strong, Woodland and Miller talk weekly, if not more often. Sometimes it’s about investments; other times it’s about family and what’s happening in their respective lives.

“We work hand in hand with Gary,” Miller says. “We’re his confidants and his advisors. We’ve been involved since before he won his first PGA Tour event [the Transitions Championship in 2011], and it’s been a wonderful relationship.

“He’s a wonderful client because he listens and he learns,” Miller adds. “He knows what he knows, and he knows what he doesn’t know. That’s important.”

Similarly, Warren has found that when advisors work with a client—whether it’s a large corporation or a small business enterprise, as in the case of Woodland—their ability to connect with that client on a personal level is extremely important. After all, if they don’t have an intimate understanding of what it is that keeps their customer up at night and a sincere desire to help the client’s business improve in every facet, they’re far less likely to deliver outcomes that enhance value and meet (much less exceed) expectations.

Major Dan Rooney knows Woodland better than most. Rooney, an F-16 pilot who served three tours of duty in Iraq, founded the Folds of Honor in 2007, intent on raising money to provide educational scholarships for spouses and children of fallen or disabled service members. Woodland met Rooney at the University of Kansas in 2009, and they instantly connected. Though both were just getting started down their respective paths, Woodland volunteered to wear the Folds of Honor logo for no charge. “He’s playing for something more than himself,” Rooney says of Woodland.

All these years later, Woodland continues to wear the Folds of Honor logo at no cost to the organization. “My wife’s grandpa, who pretty much raised her as a father figure, was in the military,” says Woodland, whose bond with Rooney has become so strong that Rooney officiated the ceremony when Gary married his wife, Gabby, in 2016. “My grandfather was [also] in the military, so we’ve kind of grown up around it.

“I’m fortunate enough to come out here and live the lifestyle I do and play a game for a living,” he continues. “These guys are going away for years at a time and sacrificing everything. You spend time with these people who have sacrificed and lost everything, it moves you. It forces you to want to do something to give back.”

Sometimes, the biggest impact can come from the seemingly smallest moments. As defending champion of the Waste Management Phoenix Open in 2019, Woodland was asked by the local group that runs the event if he’d be willing to visit with a local Special Olympian during the Wednesday pro-am. Ideally, Woodland would play the famous 16th hole at TPC Scottsdale with the young golfer.

Woodland agreed, and what was expected to be a brief interaction with Amy Bockerstette, who was age 20 at the time, instead became a heartwarming story that circled the globe on social media. He asked her to play the par-three hole, and Bockerstette made a par, hitting her tee shot in a greenside bunker, blasting out, and holing a long putt for par, famously telling Woodland and others not to worry about her. “I’ve got this,” she said.

And she did.

“I keep telling people the world needs more people like Amy in it,” Woodland says. “People are drawn to that. They want that positive energy, the attitude that Amy has and the love she has for everything. She’s dealt with struggles her whole life having Down syndrome. You can’t tell it, the way she is and her attitude. Everybody needs a little more of that. I need more of that.”

Their relationship didn’t begin and end in Phoenix. After Woodland captured the U.S. Open, he and Amy were reunited on NBC’s TODAY, where Woodland proclaimed they won the trophy together.

“He certainly didn’t have to embrace Amy the way he did—he could have just been nice and said thanks,” says Joe Bockerstette, Amy’s father. “But he’s genuinely expressed to her how much playing that hole with her affected him. I don’t know if words can express how grateful we are to him for what he’s done. He’s as real as they come, a true American hero.”

Less than two months after his U.S. Open victory, Woodland and his wife welcomed twin girls to their world. Two years earlier, the Woodlands were expecting twins, but complications led to the death of one child. Their son, Jaxson, now has two younger sisters, and Woodland is restructuring his life around his family.

Today the Woodlands call Florida home, though they keep a house in Lawrence, Kansas, where they return for periodic visits. Maintaining ties to his native state is important for Woodland, who has relied on his financial planners to help him navigate the changes in his life.

Along the way, Woodland inked a lucrative sponsorship deal with Under Armour before moving to Puma. He also signed an equipment deal last year with Wilson after playing without a club agreement until he found something that felt right to him.

“From a contract standpoint, the [Wilson] deal was phenomenal, but it was one where we had to make sure I was comfortable with it,” Woodland says. “I don’t want to just go play equipment to play it. I want to make sure it’s right [for me].”

The U.S. Open victory reinforced Woodland’s faith in his decision. As more opportunities have presented themselves, Woodland has relied on his team to help him evaluate and choose the best options.

“Preparation for the rest of my life, that’s the big deal,” Woodland says. “I want to take care of myself, but I want to take care of my kids. I want them to be safe and financially stable as well.”

That’s where Miller comes in. “You ground him in the principles that you have to fill different buckets,” he says. “You have to save.

“For Gary, it was a question of when [he would win a major event],” Miller adds. “Now it’s here. He has a system that’s been in place as if this had already happened. Now that it has happened, we just mobilize.”

Since Woodland won the U.S. Open title, his life has been transformed; however, he’s remained true to the priorities that have guided him through the years. The main thing that’s changed is that the game isn’t just about Woodland anymore.

“My whole life I’ve wanted to be the best athlete in the world,” he says. “I didn’t know what sport that was going to be. When I focused on golf in college and transferred to Kansas, I wanted to be the best player in the world. I lived and breathed it.

“Now, with kids, it puts some perspective there,” Woodlands continues. “I still want it bad and will work for it, but when I come home, I’m able to disconnect. If I play bad, I’m able to see my son and it puts me in a better spot. A couple of years ago, I would have dwelled on it and [felt like] life was over. I have a bigger purpose now.”

No doubt, this approach has served Woodland well in business and in life.