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Chip & Skip’s Excellent Adventure Marches on in Jackson Hole

By Scott MacKillop | August 22, 2023

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For some, a good challenge and a good time beat the deathly drone of sponsored sales pitches disguised as educational sessions.

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Welcome to Chip & Skip’s Excellent Adventure (EA), an event where financial service industry players gather each year to sell nothing, do no deals and talk as little as possible about business.

In 2012, EA organizers, Chip Roame (Tiburon Strategic Advisors) and Skip Schweiss (Sierra Investment Management), issued an invitation to some of their industry chums to climb 14,505-foot Mt. Whitney in California. Thirteen brave, mostly male, souls answered the call.

All hikers completed the 25-mile, 6,000-foot vertical ascent in one day, although many were worse for the wear. Little did they know the seeds of an industry tradition had been planted.

Every year since—including the COVID years, a time when most sensible people hunkered down—the EA crew has assembled for an extreme hiking experience and a joyous post-hike celebration.

Chip and Skip select the location and announce the date, but the event belongs to the participants. There are no sponsors or official organizers in the traditional sense. Just a loose confederation of like-minded adventurers bent on testing themselves and enjoying each other.

This year the venue was Jackson Hole, Wyoming, nestled at the base of the jagged Teton Range.

The event has grown and morphed significantly from its hardcore, testosterone-driven, “there-must-be-a-risk-of-death” beginnings.

The “big” hike was a 24-mile, 6,000-foot vertical ascent loop from Teton Village to Marion Lake and back. But there were shorter treks available for those with enough sense to take them.

Industry denizens are now often accompanied by spouses, sons, daughters, friends or all of the above. It’s truly a family affair. A total of 72 people showed up to hike or cheer on the hikers and celebrate afterwards.

The male/female ratio is close to equal now. The fastest finishers were a group of three trail runners: Jodi Vanneman (sister of Orion’s Rusty Vanneman), her son Sam, and his friend Kiana Levin. In fact, Sam and Kiana ran a few extra miles at the end of the hike to make it a marathon-length day.

Kiana’s performance earned her the “Junior Stud” award (yes, there is an awards ceremony at the post-hike celebration). And the “Rookie of the Year” award went to Julie Cane (CEO of Democracy Investments) for coming off the trail at the head of the first group of hikers (not trail runners). Julie was accompanied across the finish line by Orion’s fleet-footed Eric Clarke.

Hikers started the trek in three waves. The first group of 14 left at 2:30 am and were rewarded by a beautiful sunrise as they crested the peak 4,000 feet above the village below. The bulk of the EA crew launched at 4 am. The “mop-up” team left at 6 am and enjoyed a glorious waffle breakfast on the peak, where the early birds had enjoyed the sunrise.

After summiting the mountain above the ski village, the hikers dropped over into the remote Wyoming back country. Although moose and bear are plentiful there, they let us pass peacefully through the woods and endless wildflower meadows they call home.

The weather was not as cooperative. Intermittent rain and hailstorms passed over, leaving the trail a muddy mess in parts. There was some slipping and sliding, but rain gear and a good attitude always beat bad weather. By the time we finished, the sun was shining.

Skip’s wife Lisa and her crew, including daughter Anna and daughter-in-law Amy, handed out cold beverages at trail’s end. This earned the group a well-deserved “Best Supporting Actors” award. Their cooler was only so big, so we settled in at The Handle Bar, located only a few feet from the trailhead. It is Jackson Hole, after all. The party was on.

One of the best parts of each EA excursion is reliving it at journey’s end. The bonds that are forged through common effort and teamwork on the trail are palpable and the bonds that are shared by those who have participated in multiple EA gatherings are even stronger.

This is what I believe sets the EA experience apart from all other industry events. It is real and genuine. No money changes hands and everybody is a winner. The sense of accomplishment that comes with completing the trek, no matter which version you choose, is yours to keep. And the friendships that grow out of it are steadfast and lasting.

The EA ambiance is reflected in the fact that the most coveted award bestowed at the after-party is the “Spirit of the Summit” award. It is granted to the person who exhibited the most selflessness and provided the most help to others on the journey. This year’s winner was Alex Trianine of Flyer Financial Technology, whose participation in the EA was a Father’s Day gift from his daughter, Isabella Ekaterina Trianine. Alex won for assisting Colin Barber, Managing Director of the Sierra Mutual Funds, after Colin sprained his ankle early in the hike. Alex and Isabella hiked with Colin, and Alex carried his backpack for many miles.

This year’s get-together also reflected significant changes in our industry. The following long-time EA participants who started and/or grew their businesses as the EA tradition grew, are moving on, stepping back from leadership roles or starting new firms:

  • Eric Clarke, Co-Founder and CEO of Orion, is exiting his CEO position at year-end;
  • Scott Hanson, Co-Founder and Senior Partner of Allworth Financial, will soon give up his CEO title, while staying fully involved with the business;
  • Alex Potts, long-time CEO of Loring Ward, now President of Buckingham Strategic Partners, is exiting his position at the end of the year;
  • Skip Schweiss, for years President of TD Ameritrade Trust Company and the face of all things fiduciary for TD, is now CEO of Sierra Investment Management;
  • Frank Trotter, retired Co-Founder of online bank EverBank, recently left the sidelines to start Battle Bank;
  • Bill Van Law, left his position as President of the Raymond James Investment Advisors division and formed WVL Group, a wealth management consultancy; and
  • First Ascent, a flat fee turnkey asset management platform (TAMP) that I helped found as the EA tradition was just getting started, was recently sold to GeoWealth. I still play an active role in the business, making GeoWealth the sixth TAMP I’ve been affiliated with over the course of my career.

Time moves on, and our industry, like the EA, evolves and brings in new blood. But it also builds on the traditions of the past. Frank Trotter and I have been competing for EA’s “Senior Stud” award since it was first bestowed, but we are too old to remember who wins it from year to year. It’s time for more new blood. Join us next year in Telluride!