About the club · Kip

A Guide Who Remembers Your Trail

Kip is the club's guide. He helps you choose where you're headed, plan a way there you'll actually walk, and pick up where you left off, every time you come back.

He's an AI. What he's like to talk to is further down, in the words of the people who talk to him.

Talk with him
Any time, day or night
Writes to you
Every morning of an Expedition
Remembers
What you've planned and written
Steers
Never. You do.

A letter of introduction

Welcome. I'm Kip.

Before an Expedition, we sit down together at the drafting table. You tell me where you're headed and why it matters to you, and I help you turn that into a plan you'd actually want to walk: one thing you're after, and a handful of small steps you could take on any given day. I pencil lines onto the plan as we talk, and you keep the ones you like.

Every morning on the trail, I write to you: your step for the day, a tale from someone in your party, something to wonder about.

When you write a Field Note, I read it, and I remember. A week later I'll still know about the wall you hit on day nine, so you never have to start over with me.

When something you're going through sounds like a tale another explorer told the club, I'll tell you, and you can read it for yourself.

And between Expeditions, or on any day something is stuck, come and find me. That's most of what I'm for.

Kip, your guide

In their own words

What He's Like to Talk To

My interactions with ChatGPT were generally bad to neutral at best. This is my first genuinely great experience interacting with an LLM. Kip is the right mix of gentle without pandering, equally supportive and pushing back when necessary. It was like talking to a good friend, and I have to acknowledge how impressive that is.
— John A.
John A.

I started discussing possible expedition ideas with Kip the day before the expedition started. I didn't expect much in the way of guidance without extensive input and prompting. I was so pleasantly surprised by the insight and pattern recognition of the Kip AI "out of the box," so to speak. I was so surprised I spent the next week or so deeply pondering some of the questions he asked doing some real soul searching. Thus, I missed the expedition boat and Matt had to "fly me out" to join the expedition. 😅

Amber H.
Amber H.

I'm not sure why chatting with him feels deeper than when I chat elsewhere with AI, but I'm guessing it's how Matt has trained him to respond. For me, the conversations feel supportive, understanding, and almost holistic. The chat features - and personalized morning emails - are great motivators!

T. Benson
T. Benson
Kip is GREAT with empathy and validation! Better than my friends. But also keeps you on track for the chat purpose, to make the goals. Kip even had a few good things for me to ponder before making my goals. I mean, like it made me think, ‘Oh, I didn’t think of that - good idea, Kip’.
— Anita

Kip is a great collaborator for me. He gets me to see things in my life in ways I wouldn’t have thought about them on my own, and he points out ways that I am doing good that I would’ve never seen.

Dianne M.
Dianne M.

This AI guy is Kip and I surprisingly don't hate him haha he's an entire thing!!

Sam S.
Sam S.

Plainly

What Kip Is, and Isn't

He's an AI. Kip runs on language models from Anthropic and OpenAI, guided by instructions written to match how the club thinks. What you tell him is used to help you on your way, and none of it is used to train AI models.

He's a guide, not a therapist. He's warm, and he's good company on a hard day, but he doesn't diagnose anything or try to fix you. If you're carrying more than a guide can help with, he'll say so, and encourage you toward people who can.

He doesn't decide for you. He asks good questions, offers another way to look at something, and leaves the choosing where it belongs.

Everyone else is a person. Your party, the Lodge, the people who read your tales and write back.

Inner Isles Explorers Club

Questions About Kip

Do I have to be into AI for this to work?
Not at all. Your party and the Lodge are people. Kip is there to help you plan and to keep you company along the way, and you can lean on him as much or as little as you like.
Will he remember me?
Yes. He keeps what you've planned, the Field Notes you've written and what you've told him, so a conversation picks up where the last one left off, weeks later if need be.
Who reads what I tell him?
We keep what you write for you, for Kip, and for anyone you choose to share it with, and use it for nothing else. It is never used to train AI models. The privacy policy spells it out.
What does it cost to talk to him?
The first conversation, the one where he tells you whether this is the right ship, is free and needs no account. After that he comes with membership.

Something else? Email [email protected]. Matt reads every note.

The next Expedition

The December Expedition sets out Tuesday, December 1.

Start With a Conversation

Tell Kip what you're hoping for, and he'll tell you straight whether the club is right for you, including when the answer is no, or not yet. No account, no payment needed.

Already sure? Join the club.

Membership is $50 a month or $500 a year, with a 75-day refund. Nobody loses their place here because of money: makes it half, or free.