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Chip and Skip’s Excellent Adventure: Alaska’s Crow Pass


By Scott MacKillop | August 20, 2018

Articles By Us| Excellent Adventure

This year the Excellent Adventure crew assembled in Girdwood, Alaska for a trek up the Crow Pass Trail, which meanders through a rain forest inhabited by black bears, grizzly, and moose.

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Chip’s and Skip’s ‘Excellent Adventure’ breaks RIA stereotypes, sheds risk aversion for ‘gut-busting’ Alaska hike; black bears, grizzlies and moose, oh my!


The financial services industry is not viewed by most people as a haven for wild and crazy adventure-seekers.  Yet for the past seven years, Chip Roame of Tiburon Strategic Advisors, and Skip Schweiss of TD Ameritrade, have shown that stereotypes often don’t tell the full story.

Every summer since 2012 Chip and Skip have organized an Excellent Adventure and invited a diverse group of financial services executives, friends, and family to accompany them.  The common theme of these excursions is to find a hike that most people do in two or three days and do it in a single, gut-busting day.  Oh yes, and there must be “some risk of death.”

The first Excellent Adventure was a guy’s trip.  Thirteen alleged gentlemen met in Lone Pine, Calif., climbed Mt. Whitney, drank too much wine, ended the night in a hot tub, and had so much fun they decided to do it again.  The Excellent Adventure tradition was born.

Now the event is more of a family affair.  Twenty-two of the thirty participants in this year’s EA were accompanied by a partner or family member.  Only eight flew solo in the original EA tradition.  Once we hit the trail, we are all family.  (See list of participants at end of article.)

This year the Excellent Adventure crew assembled in Girdwood, Alaska for a trek up the Crow Pass Trail, which meanders through a rain forest inhabited by black bears, grizzly, and moose.  The trail was formerly part of the famed Iditarod Sled Dog Race course.

Piece of cake?

On paper, the hike looked like a piece of cake compared to past Excellent Adventures.  There would be none of the high elevation we dealt with in scaling Mt. Whitney or traveling along Colorado’s Four Pass Loop.

There would be none of the debilitating heat we encountered going rim-to-river-to rim in the Grand Canyon or navigating the jungles and lava ledges of the Kalalau Trail in Kauai.

There would be none of the ice and snow we braved as we roped-up to climb Mt. Shasta.  And no dangling from cables as we did to reach the summit of Half Dome in Yosemite.

As a warm-up, the group boarded the Coastal Classic train for a trip through the Kenai mountains to Seward where we paddled sea kayaks up Resurrection Bay.

The train whisked us by shimmering blue-green glaciers, through alpine meadows filled with wild flowers, and past streams teaming with salmon and lined by salmon carcasses the bears had discarded.  Moose, Dall sheep and bald eagles ignored us as we took in the wildness.

The hallmark of every Excellent Adventure is the bonding that goes on among its participants.  The train ride and the voyage up Resurrection Bay gave us the opportunity to form or renew the relationships that are essential to the success of any limit-stretching endeavor.

Common experience and a common purpose knit us together.  We learn to trust and rely on each other.

Pulling an Excellent Adventure together is a lot of work.  Fortunately, for the rest of us, Chip and Skip get stuck with all the work.  Organizing the group’s logistics is part of their job.

Twenty-one of us were attempting the long march from the Eagle River Nature Center, over Crow Pass, and down to the Crow Creek Trailhead (somewhere between 23 and 26 miles, depending on which source you consult).

Seven others were doing a shorter hike that started at the Crow Creek trail head where the longer hike was going to end, ascended to the top of Crow Pass, and descended back to Crow Creek trailhead (8 miles).  Of the two sane members of our group, one was going salmon fishing and the other was planning a spa day at our hotel.

Getting the 21 long-hikers to the Eagle River Nature Center required a shuttle bus.  The bus was scheduled to meet us at our Girdwood hotel at 3 am sharp for the hour and a half trip to the trailhead.

The bus didn’t show.  When Skip contacted the bus driver at 3: 02 am, he insisted he had no record of our reservation.  Using the utmost tact and diplomacy, Skip coaxed the bus driver to high-tail it from Anchorage to Girdwood (about 40 miles) to collect us.

At 4:30 am our ride arrived, which meant we were going to start our hike about an hour and a half later than planned.  This is not a good outcome when the hike is expected to take between 12 to 15 hours.

The bus driver attempted to make up time by barreling down Alaska’s only real highway while talking non-stop, presumably to distract us from focusing on his tardiness.  The road was wet, and the bus frequently engaged the rumble strips as our driver gesticulated wildly to emphasize the important points in his manic monologue.

Facing the bears

Finally, we reached our destination.  It was now time to face the bears.

We had encountered bears on past Excellent Adventures.  One greeted us upon our midnight arrival in the parking lot at the Mt. Whitney trailhead.

Black bears and grizzlies can be a threat to humans hiking in Alaska.

Skip and Bill Van Law crossed paths with a mama and her cubs on the descent from Half Dome.  Ron Carson and Steve Sanduski both had bears invade their living quarters on the Four Pass Loop excursion.  But we had never willingly walked right into their neighborhood.

The Eagle River Valley is home to black bears and grizzlies.  A grizzly killed a solo hiker earlier this year, and a black bear killed a 17-year old trail runner the year before. There was a sign at the Crow Creek trailhead warning of a black bear that had recently been stalking hikers.

We knew this and came prepared.  A few of us attached bear-bells to our packs.  Most carried bear spray, and a few were packing something stronger.

We had watched the videos telling us how to tell a black bear from a grizzly, a curious bear from an aggressive bear, and what to do in each case.

We learned about making noise to let the bears know we were coming.  We agreed to hike in groups of at least four so we could bunch together and make ourselves “look big.”

Our anti-bear tactics seemed flawless until we set foot on their turf.

The Eagle River Valley is essentially the far-north version of a jungle.  In the summer, the vegetation is lush and thick, nurtured by rivers, rain, and cool temperatures.

The brush and grasses are more than head-high and often cover the trail.  In places you can’t see your feet as you push through.  A bear could be standing a foot away and you would not know it.

We don’t know how far from us they were, but they were there.  The steaming piles of bear scat told us so.  The grizzly paw prints in mud did too. In many places along the trail the grasses were flattened where bears had plopped down for a nap.  Maybe our bear bells were working?

Alaskans are apparently confident in their navigational abilities because they don’t place directional signs along their trails.  In Colorado we love trail markers and signs of all varieties.  We expect to see a sign at every fork in the trail.  Alaskans are minimalists in this department.

Our group of 21 hikers quickly broke up into 4 sub-groups moving along the trail at different speeds.  My group got lost a lot.  This is hard for a seasoned Colorado hiker to admit.

Maybe it was the lack of signs or maybe we were just too preoccupied with avoiding a bear hug.  I don’t know, but being lost in bear country is an uncomfortable feeling.

The first time we got lost was about 6 miles into the hike.  We were traversing a swampy bog and the trail just seemed to disappear in the tall grasses.  We did what any financial services executives would do.  We consulted an app.

The data lies

In our industry we are conditioned to genuflect at the altar of technology and not question the data.  When it speaks, we listen.  But sometimes the data lies.

After almost an hour of searching, it dawned on us that the app might be wrong.  We went back to the last place we were confident we were on the trail and started forward again, ignoring the app.

Soon we saw a break in the grasses.  We’d found the trail.  Sometimes experience and judgement beat technology.

Our confidence renewed, we attacked the trail, trying to make up time.  Our pace was brisk, but we were occasionally slowed by the climbing ropes and ladders that were built into the trail to aid in passing through its most difficult sections.

We could feel time slipping away and cursed the manic bus driver who was responsible for our late start.

The next time we got lost was at the 10-mile mark.  We were about 1 mile shy of the point at which our maps said the trail crossed the mighty Eagle River.  But the trail simply disappeared in the dense woods.

Our initial efforts to relocate it were unsuccessful and we terminated them entirely when we spotted a large grizzly paw print in the mud at the edge of the woods.

Having no alternative, we decided to cross the river at that point.  We confirmed via walkie-talkie that earlier groups had done the same.  Alaskans apparently don’t like building bridges any more than they like putting up trail signs.

We pulled off our hiking boots, donned our water shoes, and slipped one-by-one into the grip of the frigid waters.  For some, the pain caused by the icy waters did not wear off until we were well down the trail on the other side.

That was the first of four river crossings we made that day.  The breadth of the river varied at each one—the longest being 150 feet from bank to bank.  The depth of the water varied too, depending upon the height of the hiker.

It was knee deep on taller hikers and top-of-leg deep on the shortest.  But for everyone the swiftly moving, glacier-fed water created a powerful force against which we had to battle both mentally and physically.

The first 12 miles of the hike had a slight uphill profile as the trail lazily followed the river up-valley.  The next 8 miles were another matter.  It was now time to climb out of the valley toward Crow Pass—elevation about 3,500 feet.

The 3,000-foot climb increased in steepness as the trail approached the pass.  This is where time spent on the Stair Master really paid off.

After climbing out of the valley the trail flattened out and traversed the scree-covered Chugach mountains heading toward Crow Pass.  But the fog descended and made it impossible to tell the difference between peaks and passes.

We could not see our target.  The trail branched off in many directions.  Without being able to see Crow Pass we didn’t know which branch to take.

We were lost again.  It was about 7 pm.  Tick, tock. Thankfully, in summer it stays light in Alaska until 11 pm.  But the group was weary, and energy reserves were low.  We would still have 4 miles to go after we found Crow Pass and with the dense fog that had settled in, we had no way to logic our way to our destination.  We were momentarily frozen in our uncertainty.

The prospect of spending the night on the mountain proved highly motivating.  Although we were drained from hiking 22 miles, we sent scouts to look for any indication of the trail to Crow Pass (of course, there were no signs).

Conquering Crow Pass

Almost immediately Skip and his son Michael found a promising up-slope trail and called to the group to follow.  We had hope.  Our energy surged.

Another 200 yards of hiking and we were standing at the top of Crow Pass.  For the first time all day, there was a sign telling us where we were. We had not been far off course but couldn’t tell that through the fog.  The problem had mostly been in our minds.

On our 4-mile trip down the mountain anticipation replaced anxiety.  The trail was wide and well-traveled, with good visibility on both sides.

No danger of bears lurking in the trail-side underbrush or surprising one as we picked up our pace to the trail-head.  The trail was well-marked and easy to follow.  We were horses heading back to the barn.

The cars we had left at the trailhead the day before were waiting for us along with a cooler full of beer and a couple of boxes of cold pizza, courtesy of Chip and Craig Gordon.  This family cares for its own.  Pizza never tasted so good.

All 21 of the long-hikers and the 7 short-hikers successfully completed their journeys without injury.  We donated our unused cans of bear spray to the locals.  Vicki Hutton caught lots of salmon and Carol Trotter had a magnificent day at the spa.

The fastest group (Chip and Craig Gordon) completed the hike in about 12 hours and were applauded for their swiftness even though they violated the 4-in-a-group rule.  My directionally challenged group completed the 26.2-mile hike (marathon distance) in 15 hours.

The victory party started after 10 pm.  We celebrated into the night with more beer and warm pizza.  Everyone was smiling.  You could feel the bond.  We had accomplished something life-shaping together.  It’s something we will always share.

Core Values

Years ago, the EA group developed three core values. They are, in order of importance:

  • Return home alive
  • Have fun
  • Attain your personal objectives

We’d all lived up to the EA code and learned a lot:

  • On a long adventure, you will have problems.  The question is how you deal with them.
  • The best reaction to adversity is calmness.
  • You’ll be surprised at what you can accomplish when you have no alternative.
  • Determination trumps fear.
  • Camaraderie lessens pain and keeps hope alive.
  • You’ll work harder to avoid letting your team down than you will work for yourself.
  • Be prepared.  Plans change.  Sometimes there are no signs.  Trails disappear.  Adjust.

List of Excellent Adventure 7.0 Participants
This year’s group was geographically diverse, but California-centric.

From the Golden State:

  • Chip Roame (Tiburon Strategic Advisors) and son Blake
  • Alan Clopine (Pure Financial Advisors) and his two sons, Ryan and Rob
  • Craig Gordon (RBC Correspondent & Advisor Services)
  • Sarka Holeckova (Sarka Photography) the official EA photographer
  • Tif Joyce (Sonoma County Wealth Advisors)
  • Kevin Zachary (Cloudera) and son Ian
  • Evelyn Zohlen (FPA president-elect) and husband Mark Prendergast (both of Inspired Financial)
  • Jessica Trotter (TIAA Bank) daughter of Frank and Carol Trotter (see below)


  • Skip Schweiss (TD Ameritrade)
  • Scott and Teresa MacKillop (both of First Ascent Asset Management)
  • James Passarelli (Economic Group Pension Services)


  • Ron Carson (Carson Wealth)
  • Rusty Vanneman (CLS Investments) and partner Vicki Hutton

Arizona, Florida, Texas, and Missouri:

  • Billy Oliverio (United Planners) and Fordham-bound son Diego (Scottsdale)
  • Bill Van Law (formerly of Raymond James) and partner Cynthia Hardwick (St. Petersburg)
  • Craig Wietz (First Rate) (Dallas)
  • Michael Schweiss (University of Dallas) (Dallas)
  • Frank Trotter (formerly of EverBank) and wife Carol (St. Louis and sometimes Colorado)

Maryland and North Carolina:

  • Anders Jones (Facet Wealth) (Baltimore)
  • Dan Tobias (Passport Wealth Management) (Charlotte)

And the Winner Is
Every year Chip and Skip present EA group awards for exceptional performances. This year’s winners were:

  • Rookie(s) of the Year:  Michael Schweiss, James Passarelli, and Anders Jones
  • Senior Stud:  Frank Trotter
  • Spirit Award:  Vicki Hutton and Kevin Zachary


Excellent Adventure 8.0 will head east for the first time.  The group will hike the Presidential Traverse in New Hampshire July 13-15 (the hike itself will be completed in one day).  The trail is 22 miles long and touches the tops of eleven peaks in the White Mountains range.  Total vertical gain for the day is 8,800 feet.  A very stout hike.  At least there won’t be any bears.

Scott MacKillop is CEO of First Ascent Asset Management, a Denver-based firm that provides investment management services to financial advisors and their clients.  He has participated in all seven Excellent Adventures and plans on completing the Presidential Traverse.  He can be reached at