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Ask anyone who has met Chip Pyfer and they’ll likely describe him as welcoming, gregarious, and dedicated to his work at Private Ocean. As a lead advisor, Chip is “all-in” when it comes to working with his clients and helping them plan for their future. He’s also “all-in” when he’s off the clock too, whether he’s planning his summer adventure vacation with his family or gearing up for one of his incredible annual mountaineering challenges.

Recently Chip and his fellow climbers, Alden Mills and Brett Bush, completed an incredible two-week Denali expedition (Mt. McKinley), to create awareness for The Guardsmen, whose mission is to provide educational opportunities for at-risk Bay Area kids, and raising funds to support The Guardsmen Scholarship Endowment Fund. The trio has completed such a trek nearly every year for the past decade, and this year’s expedition raised over $26K in funds – far surpassing their goal of $20K!

In this interview, Chip shares his experiences and lessons learned from the trip.

Preparation was Key

Not unlike his work in the office, the trip took an enormous amount of forethought and planning. “At 20,310 feet Denali is the highest mountain peak in North America, and we knew this would be an incredibly challenging climb,” Chip says. “This year’s trek took more than a year of preparation, with layers of planning for each step of the journey from scheduling, budgeting, and all of the logistics related to equipment, travel and transport. It was not an inexpensive endeavor, and our plans had to be precise. There were very specific requirements, for example, for transporting and carrying individual and team equipment on the mountain, and everyone on the team led specific planning steps prior to the climb. It was definitely a well-orchestrated event.”

Discipline and Expectation

Even the most experienced climbers face challenges outside of their control, from weather and wind conditions to the health of the team. “The physical exertion you expend at that elevation takes a toll,” Chip explains. “Each day, you’re burning five to ten thousand calories – I lost 15 pounds! You prepare for some things, but sometimes there’s something you don’t anticipate. In this case, it was sleep deprivation. After 10-12 days in a row of 5 hours of sleep, it adds an even higher level of challenge to the climb. All we could do was stay focused and disciplined on the day’s journey.”

Denali’s 14,000 foot base camp with a view of Mt. Foraker in the background.


“This was a trip that was 15 days on a glacier, where every day was a serious physical challenge,” Chip says. “You’re roped up and looking at the heels of the climber in front of you for hours. You’re sleep deprived. You’re pushed to your limit. It took so much physical and mental effort to accomplish what we did each day and none of us could have done it alone.”

“I’ve heard that you’re only as strong as your weakest link, and that is never more apparent than when you are roped up with your climbing teammates.” Chip added. “I’m not a professional mountain climber. We use professional guides to make sure we use good judgment, state of the art technical equipment, and mountain familiarity. But we were fortunate to have an amazing group of people on the team. We had a smaller group this year and found our agility gave us speed and momentum. We were supposed to complete the expedition in 21 days but finished it in 15! The exceptional weather on our summit day was also a bonus.”

The hiking team descending from Denali’s summit

About The Guardsmen

The Guardsmen is an all-volunteer organization founded in 1947 whose members raise money every year to fund nearly 14,000 days of summer camp and over 250 private school vouchers for disadvantaged Bay Area youth.

Chip was introduced to the organization some 20 years ago through a friend and member at the time. He had recently settled in the Bay Area with his family and was looking to get involved in the local community and meet new people. Many years later, as his tenure as an “active” member of The Guardsmen was coming to a close (and he was nearing his milestone 40th birthday), Chip and his friends decided to go big – and climbing Mt. Whitney was a natural challenge.

What started as a celebration turned into a nearly annual event, an escape to the outdoors that was both exhilarating and challenging. As for what’s next for Chip and the team, he’s not ready to unveil the 2019 challenge.

“Denali is one of the Seven Summits – an amazing feat – and I got to climb it with great lifelong friends,” Chip says. “For days at a time, there was zero connectivity and it was therapeutic for us to do something extraordinary, be out in the wilderness, and take a break from day-to-day life. We’re just starting talks about next year’s adventure but I’m certain it will be an incredible ride.”

Learn more about The Guardsmen and their programs for at-risk youth in the Bay Area at

Chip Pyfer (left), Alden Mills (middle), and Brett Bush (right) at the summit of Mt. Rainier August 2018

By the Numbers: A Decade of Mountaineering

2018 – Mount McKinley:  20,310 ft.

2017 – Mount Rainier (Emmons Glacier route):  14,411 ft.

2015 – Mount Rainier (Camp Muir route):  14,411 ft.

2014 – Mount Hood:  11,250 ft.

2013 – Grand Teton:  13,775 ft.

2010 – Mount Shasta:  14,180 ft.

2009 – Mount Whitney:  14,505 ft.