Like most of the enterprises Chuck Shepard has thrown himself into, the ins and outs of owning a ski resort were not something he was particularly familiar with, Shepard told Lebanon Chamber of Commerce members last week.
Shepard, the zestful and sometimes self-deprecating founder of an extensive real estate empire that made him a millionaire by age 30, recounted his journey to ownership of the Hoodoo Ski Resort in 1999 during the chamber’s monthly Forum Lunch Friday, Jan. 30, at Samaritan Lebanon Community Hospital.
Shepard, now 77, grew up in a suburb of Milwaukee, Wisc., where he attended high school and then moved on to the University of Wisconsin, graduating in 1971 with an accounting degree.
“Shortly after that, my wife Tish and I decided that we wanted to live in the country, on land that had a creek, a pond, lots of trees and that was cheap,” he said. “In order to find land like that in Wisconsin, you had to live in northern Wisconsin where there are two seasons, July and the beginning of August, and the cold season.”
That wasn’t for them, he said, so they decided to move.
“We found Nirvana in Oregon,” where they bought 300 acres in 1971 on Mount Tom in the Coburg Hills, south of Brownsville.
about his experience as owner of Hoodoo Ski Resort.
– Photo by Scott Swanson
He spent $2,000 to build a 500-square-foot home out of used lumber, with used windows.
“We had an outhouse out front and dammed up the creek that went by above it for a bath,” he said. “I was a hippie, living there.”
They were happy, he said, but eventually “we were getting a little bored.”
So he went back to school in 1975, a master’s degree in agronomy from Oregon State University.
During that time, he said, “I had an epiphany. I finally started to realize that I’d been wasting my time living on the hill. I was familiar with the Bible enough to have heard it said that we’re all blessed with gifts or talents.”
‘Organized’ Businessman
One of his, he said, was math – which he loved as a youngster.
“My first job was at the age of 12, mathematical accounting.”
He also loved to work, so he started a residential real estate investment business called Umbrella Properties.
He said he laid out principles that he intended to operate by:charity, honesty, integrity and purpose – which, he added, result in “happiness.”
“I like to be organized,” Shepard said. “I made a perfect businessman. I was good at making money. I wasn’t good at other things, like my hippie self. I wasn’t good at art, or anything like that.
“But I did what I enjoyed, and consequently, now that I’m 77 and I’ve worked for 55 years, I’ve really never had a day of work. I’ve always enjoyed what I’ve done and looked forward to it.”
Shepard said a conversation with a real estate agent when he was 27 years old prompted him to launch himself into real estate investment.
“She said that if she had started investing in real estate when she was my age, she would be much better off now. She was right, because I did start buying real estate at that time and by the time I was her age, I was able to afford to be able to buy a ski resort.”
He said he was able to get loans partly due to his knowledge of accounting, but he also did a lot of hands-on management and maintenance of the rental properties he’d purchased, which was an educational experience in itself.
Shepard said he took some classes in an MBA program at the University of Oregon and read the Wall Street Journal and books about real estate.
The price of commercial real estate skyrocketed in the late 1970s, and Shepard had also invested in gold, which increased exponentially in price.
Helped by his accounting knowledge, he was able to expand his business, he said, particularly during the real estate depression that occurred in the mid-1980s. He said he at one time owned 20 duplexes and a 26-unit apartment complex in Lebanon.
Today, Shepard said, his children and grandchildren are involved in his company, which owns 5,000 units in Lane County, Bend and Phoenix, Ariz.
“I’ve turned over 60% of the ownership of the company to my children and grandchildren. I’m really retired from Umbrella Properties, except for being on the board of directors,” he said.
Customer Friendly
Hoodoo is where he likes to spend time, he said, particularly in the parking lot, where visitors are used to seeing him, greeting them.
“I spend a lot of time in the parking lot,” Shepard said, adding that shortly after purchasing the resort – for $1 million, described by one of the attendees at the chamber meeting as “a dump” at the time.
Shepard said he decided to turn things around in multiple ways, including building a new lodge in 2002 and adding other attractions.
“Also, I decided to make myself totally available to my customers,” he said. “That first season I started greeting skiers that came into the parking lot and helping them find a place to park.”
His son-in-law Matthew and oldest daughter Tasha manage the resort – they met at Brighton in Utah, where she had gone to learn the ropes of ski resort operation.
Hoodoo’s focus is intentionally different from other resorts, Shepard said.
“Early on, we made a decision to aim our marketing toward families, rather than teenage boys. Traditionally, the teenage boys, from, like, 12 to early 20s, that’s the group you aim toward. And then they bring their girlfriends and other people. That’s just who the ski community goes after.
“I decided I didn’t want to do that. I came from a church that was very family-oriented and I decided this was going to be about families.”
Also early on, he incorporated a mascot, Harold the Hodag, a dinosaur-like critter that hailed from his Wisconsin childhood, into the resort’s advertising.
Challenging Business
Running a ski resort is an enterprise with significant ups and downs, Shepard said, noting that if there isn’t snow by Jan. 1 – as has been the case this year, the resort stands to lose money – possibly as much as $2 million this year. .
A significant blow has been the loss in 2019 of a five-year contract Hoodoo had held for 15 years to manage 47 local U.S. Forest Service campgrounds during the summer.
Shepard told Woodall’s Campground Magazine that year that the extra revenue not only helped even out fluctuations in the winter ski business but provided summer work for his staff, enabling him to keep key managers on payroll throughout the year, as well as provide summer jobs locally.
USFS managers, he said, abruptly gave the contract to Utah-based Utah-based American Land & Leisure.
“They didn’t give us any explanation at all, except that it was a business decision, which usually means that it’s not a business decision,” Shepard told The Register-Guard.
At the Forum Lunch he said Hoodoo had been rated “outstanding in every category” and that “the Forest Service people, for the most part, liked us.”
“We increased their fees that they got by about three-fold and had done very well for them.”
He told the chamber audience that the longtime Willamette National Forest supervisor with whom Hoodoo staffers had worked for years had been replaced by a “new person” who was “really kind of jealous.”
“When you wanted to talk to somebody about Forest Service campgrounds, you talked to me, not her,” Shepard said of how he now evaluates what played out. “She didn’t like that, and we lost the campground concessions – devastating for us. She didn’t realize that what she was doing was marking the death of Hoodoo ski area.”
He said later that that official had moved on.
A request by the Register-Guard for documentation behind the decision was denied by USFS officials, citing federal contract regulations that prohibited them from disclosing proprietary business information, Woodall’s reported.
Uncertain Future
Shepard told Woodall’s at the time: “We got into the (campground) business because it really helped the ski area, so this will hurt the ski area quite a bit.”
Hoodoo had purchased or established some RV parks to go along with its campground management business – in Camp Sherman, McKenzie Bridge,Willamette Pass and Dexter, and at the ski resort itself and Crescent Lake Resort.
He said other ideas, such as putting a golf course to provide summer income, haven’t panned out.
“I, more or less, can stop on that note, because Hoodoo really does need a summer operation, and the campgrounds were essential,” he said. “We have not found anything major to take their place.”
Hoodoo is all about family, Shepard concluded.
“A lot of happy people,” he said, gesturing at a projected photo that showed people enjoying the snow. “So many people say the best thing about Hoodoo is the atmosphere, the culture of how happy everybody is.
“I have six kids, 19 grandchildren. They’re up there all the time. Future owners. Hopefully, we have a future.”