04/09/2026
Introducing the Private Guide Marketplace on Oak 💪
We’re super excited to bring a new way of booking private guides to the market.
Over the past two years, we’ve experimented with different ways of booking private guides, joining courses, and teaming up to share the cost of hiring a professional.
And through that process, we realized the real inflection point:
Unless you’ve booked a guide before, no one really knows how to book their first one.
Who do you contact?
What do you ask?
What’s the general price level?
And how do you know who you’re actually booking?
Today, you often end up searching across different websites, finding a few emails, maybe sliding into a guide’s Instagram DMs, or booking through a local guide office without ever meeting the guide or even knowing their name.
Oak changes that.
For users: instead of sending 10+ enquiries across five different platforms, both digital and physical, you make one request. That’s it.
For guides: instead of juggling WhatsApp messages, emails, low-commitment enquiries, unclear pricing, and back-and-forth with people who may or may not book, you can send one clear offer per request with your dates, price, and what’s included.
Oak captures the transaction immediately and handles payout properly.
As a guide, you’re in full control of which requests you receive. Set your coverage area on a map, choose the sports you offer, and Oak will match you with relevant requests.
It took us a few years to really dial in this system.
But now it’s here.
And we believe it’s the perfect add-on to our free mountain community. 🫶
