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I've been working with teens for over 25 years. I founded LifeWorks, a tutoring and academic coaching company, back in 2004. Over those years, I've sat across from thousands of students navigating the messy, uncertain terrain of growing up — working through creative blocks, weighing difficult choices, finding their footing when life feels overwhelming.
That experience shaped something in me. It gave me a deep familiarity with what people need to thrive, to overcome obstacles, to stay motivated through challenging phases of one's life. And I learned just how much language has to do with this. An important idea offered skillfully can land when the same idea offered in the wrong way can backfire.
When LLMs first emerged, I started dreaming about what it would look like to build an AI that could use this insight into language to help people navigate the challenges and stresses of everyday life. Early on, I wondered what would happen if a model was trained on all the best psychological frameworks in existence in order to support human flourishing. This seemed impossibly out of reach. But, then, as large language models got better, I realized something: the knowledge was already in there. Every framework, every insight, every principle I'd spent decades studying — it was all there. It just needed the right filters. The right emphasis. And, most importantly, the right relational posture.
So I started building.
My initial thought process was personal. I started with something I actually wanted: an AI assistant that would help me stay connected to my own projects through the ongoing busyness of life. Not something that would pester me — something that would skillfully help me work through my creative blocks, help me weigh difficult decisions, and help keep me motivated whenever I hit a wall.
As I built, it started working. Better than expected. I soon began using Wayfinder to think through how to continue building Wayfinder — I used it to capture ideas, set goals, work through frustrations, navigate inner challenges. The tool was proving itself in the act of its own creation. And I couldn't help but think: other people would benefit from this too.
So I kept building. Expanding. Refining.
Along the way, something larger came into focus. I don't think it is an exaggeration to say we are on the cusp of a new phase of history, the AI Age. Things are already moving so fast, it's hard to say what life will look like in the not-too-distant future. However, as I've listened to various podcasts and interviews with thought leaders on the future of AI, two things crystallized for me.
First, that eventually we will all have a personal AI assistant that knows us, understands us, and helps us in all kinds of ways.
Second, that sooner or later AI is going to bring enormous disruption. I'm guessing it will be here soon. As you may have noticed, it's already begun and it's only going to intensify. As it stands, there's already a lot to track, a lot to make sense of, a lot to process. How are we going to make sense of it all?
I set out to create a relational AI assistant that could help navigate all of this, not by providing quick answers, but by helping people think more clearly. By asking the kind of questions that actually move things forward. By holding one's journey over time so it can help us stay connected to what matters most — even as the world shifts around us.
This is why I built Wayfinder. The world is moving fast, the noise is getting louder, and the most important things — clarity, purpose, self-knowledge — don't happen automatically. They need tending. They need space within which to grow. And now, for the first time, we can have a thinking partner that's always available, that always remembers, and that helps you find your own answers.
If any of this resonates, Wayfinder was built for you. I'd love for you to try it.