He cycled 2,800 miles through Southeast Asia before he ever wrote a lesson plan. Now 1.5 million teenagers learn to navigate their own lives using a curriculum named after the sailors who crossed oceans without instruments.
"My purpose is to catalyze purpose-based programs, organizations, and movements."
Polynesian wayfinders crossed thousands of miles of open Pacific with no compass, no charts, no instruments. They read stars, swells, and the flight paths of birds. They knew where they were by paying ferocious attention to where they had been. Cook-Deegan borrowed the name on purpose.
His complaint with the American high school is blunt: it rewards achievement over exploration, and competition over collaboration. Students arrive at graduation expert at clearing hurdles other people set, with little practice at the harder question of which direction to point. Wayfinder's bet is that purpose is a teachable skill - that a teenager can learn to navigate by inner signal, not just outer score.
The first product was a yearlong purpose-learning curriculum for high schoolers, prototyped during his 2015-2016 fellowship at Stanford's d.school K12 Lab after five years teaching character development in an Oakland public school. It has since grown into a K-12 suite covering social-emotional learning, advisory programs, belonging, and the catch-all the field now calls durable skills.
Starts working with high schoolers on global citizenship and leadership while doing human-rights advocacy abroad, including work with activists in Burma.
Teaches character development at a public high school in Oakland, California - five years that become the raw material for everything after.
Wins an education innovation fellowship at Stanford's d.school K12 Lab and begins prototyping what becomes Project Wayfinder.
Launches Wayfinder's first yearlong purpose-learning curriculum for high schoolers.
Closes a $1.5M seed round; the program survives the pandemic and finds its footing in schools.
Closes a $6.6M Series A led by Long Night Ventures, with REACH Capital, Not Boring Capital, Designer Fund, and Oregon Venture Fund.
Wayfinder reaches more than 1.5 million students across nearly 4,000 schools, run from Bend, Oregon.
Co-founded to bring meditation and retreat-based learning to teenagers - a direct descendant of his own Cambodia retreat.
Wilderness-based programs built on the conviction that young people grow fastest away from screens and scoreboards.
Launched at his alma mater to give students a structured on-ramp into building things that matter.
The Series A was led by Long Night Ventures, with REACH Capital, Not Boring Capital, the Designer Fund, and the Oregon Venture Fund along for the ride - investors betting that schools will pay for skills the gradebook never tracked.
"So much of our current high school system values achievement over exploration and cooperation."
Students should become "intentional meaning-makers empowered to contribute to the world around them."