Wealth & Wilderness: Field Notes from Our First Los Angeles Field Trip
Last October twelve incredible women met at Gentry Market tucked inside the Calamigos Ranch grounds in Malibu. Most didn’t know each other. A few, by coincidence, came from my world in the music industry, which instantly made things feel familiar. The rest were total strangers.
It was the inaugural Los Angeles-based Field Trip for Wild Duchess. A one-day, localised experiment I wasn’t entirely sure would work. I’d planned it as a gentle test: could we bring high-achieving, busy women together to talk about something as charged as money, but do it outdoors and around an activity?
The Hike
We started with coffee and introductions before hiking through the ranch and up into the Santa Monica hills, surrounded by the end-of-summer wild sage and the caw of remarkably large birds (for being just outside of Los Angeles).
Along the way our event sponsor, Hayley Dickson, a CFP and founder of RIPPL Wealth Management, shared a few thought starters that opened something in the group:
Where do you feel scarcity right now? Is it time, energy, or money?
And the kicker question: Who shaped your first ideas about wealth?
Did you grow up with an overspending parent, entrepreneurial parents in feast-or-famine cycles, or was money always scarce?
Was money weaponized by one of your parents against the other? (This one hit deep for some people.)
Duchesses hiking back down to Calamigos Ranch, Malibu.
As a Brit (we tend to not really talk about these things), I was nervous about how heavy these questions were, and if they’d put the attendees off, but how wrong I was.
Instead, I saw pairs of strangers diving into their lives and history with each other as they hiked back down that small mountainside. We talked about what money attitudes and traits we’d inherited from our families, what we’re trying to unlearn, and how we define our own habits around money.
The conversations were open and honest, and I think perhaps walking down a mountain and not having to maintain eye contact while talking about such personal things probably helped.
The Orchard
Attendees enjoying charcuterie in The Orchard at Calamigos Ranch, Malibu.
We ended the hike with a light lunch in the beautiful Calamigos Ranch orchard, where they often hold wedding receptions. Everyone enjoyed a picnic-style charcuterie spread laid out on blankets overlooking the hills around us. It felt like one of those last beautiful-weather Sunday’s of the summer - even though it was October.
We shared a soulful guided breath-work session with Madison Vickery - check out her Substack, Becoming Resonant, about her practice, and holistic approach to A&R.
This was followed by the Wealth & Mindset discussion led by Hayley, who got us thinking deeper about our attitudes toward wealth building and financial health as a form of self-care, and over-arching themes we should be considering.
She shared her own personal journey that led her to do what she does today - empowering many women with their financial wellness. You can read more about her approach and services here.
CFP Hayley Dickson of RIPPL Wealth Management, in her natural habitat - when not managing assets.
The Rippl Effect
Since then, I’ve had messages from attendees saying they’ve met for lunch, started collaborating, or even begun working with Hayley.
And I guess that’s what’s at the core of Wild Duchess (and my background in the music industry): bringing like-minded folk together that I think would love to collaborate, be friends, or work together.
The ripple effect (no pun intended) that starts when you gather the right people and give them space to be themselves, and continues long after the event, is the ultimate win.
What Wild Duchess Does Next
This first LA Field Trip was a market test, but it’s clear there’s a desire and need for being outdoors together, meeting new people, paired with an intentional and educational topic of conversation for driven, executive women.
We’ve started with Wealth & Wilderness, but there will definitely be more. I’m so tempted to curate ‘Crypto & Canoeing’ around the Marina, but I still can’t tell if I’m joking with myself or not.
Wild Duchess started as a daydream from my corner office as I was climbing the walls going back to four-day in-office weeks.
A few months later, we’ve hosted a very intimate retreat in Montana and now this sold-out gathering in Malibu. We’ve just opened the waitlist for Montana 2026, and Somerset (UK) 2026, with another closer to home in Los Angeles coming soon. It’s starting to feel like the beginning of something much larger.
If you’re reading this thinking that this is your vibe, take this post as your nudge. Join the mailing list, come along next time, or just keep following as this thing quietly takes shape.
Here’s to more wealth, more wilderness, and designing a life that holds room for both. 🌿
