Three Takeaways from Our Skip Schweiss Interview
I’ve known Skip Schweiss for nearly ten years. The first time we spent meaningful time together was on the Kalalau Trail along Kauai’s Na Pali Coast. It’s one of the most beautiful hikes in the United States—but also one of the most dangerous. Crawlers Ledge, in particular, narrows to a cliffside path with steep drop-offs to the ocean below.
That day, we were fortunate it wasn’t rainy or windy, but it was hot and humid. Near the end of the long trek, one hiker bonked—completely out of energy. I had stayed back with him, trying to help him recover enough to make the last mile. But he wasn’t moving.
Skip, who had co-led the hike with Chip Roame as part of their annual “Chip and Skip Excellent Adventures,” realized something was wrong. Along with Chris Riggio, he came back for us. Together, we got the hiker safely off the trail and back to camp.
I share this story not just to mark the length of my friendship with Skip, but because it perfectly illustrates the kind of leader he is. That same quality came through clearly in our recent Invest Well, Be Well interview.
Here are my three main takeaways:
1. Skip embodies servant leadership.
Skip cares deeply about the mission—but just as much about the people. He’s humble but strong, never seeking the spotlight, yet always ensuring progress is made. Whether on a trail or in business, he makes sure the team gets where it needs to go.
2. He practices resilience before preaching it.
Skip believes you can’t lead others unless you take care of yourself first. On the hikes, that means being personally prepared—hydrated, fueled, equipped. In life and work, it means practicing physical and mental routines that keep him present and grounded. He models the resilience he encourages in others.
3. He leaves you with memorable wisdom.
A couple of his phrases stuck with me. He spoke about the need to “keep the soul” of financial advice, especially in an age of AI and automation. Advisors, he said, must balance technology and fiduciary duty without losing the human heart of the profession.
He also reminded us of the power of presence: “being where your feet are.” Simple, but profound advice for both leadership and life.
And finally, he shared a lesson from his father:
“Anything worth having is worth working for. I can look up at that mountain top and say I’d really like to get there. But I don’t have access to a helicopter, and there’s no escalator. There’s only one way up—and that’s to work for it.”
Skip is a leader who lives what he teaches. I hope you enjoy this conversation as much as I did.
Invest Well, Be Well.
Listen here: Skip Schweiss – Being Where Your Feet Are