Uncharted Insider

Uncharted Insiders are letters I send every month from my inbox that highlight updates on Uncharted's progress as well as reflections on ideas and reflections on conscious leadership, impact, and personal life.

Uncharted Insider

The Insider - November 2024

On simplicity, doing singular work, and writing with uncommon honesty.

Uncharted Insider

The Insider - October 2024

The evocative soul of our work exists, it’s just hiding beneath our reasonable, incremental efforts.

Uncharted Insider

The Insider - August 2024

The new media landscape, Founder mode, failures of imagination, and the work of growing up.

Uncharted Insider

The Insider - July 2024

On playing it safe, the directionality of ambition, tolerance for managers, and aspen groves.

Uncharted Insider

The Insider - June 2024

On the delegation trap, the best newsletters in your inbox, and the West Coast Trail.

Uncharted Insider

The Insider - April / May 2024

On entitled fundamentalism, the void of strategy, the errors of climate tech, and morning routines.

Uncharted Insider

The Insider - March 2024

On wasting time, removing obstructions, and The Parenthetical.

Uncharted Insider

The Insider - January 2024

On conversational frames, the aristocracy of ideas, leadership by alignment, and all that remains unchanged.

Uncharted Insider

The Insider - December 2023

On the intelligence of care, the pursuit of the tangible, the future of American cities, carbon credits, and cathedral building.

Uncharted Insider

The Insider - November 2023

On the bias for inaction, the need for context, the attack on our attention spans, and the power of Think Weeks

Uncharted Insider

The Insider - October 2023

On my next professional chapter, the game of leadership, and the courageous middle ground

Uncharted Insider

The Insider - September 2023

On the flight to quality, satellite internet geopolitics, and people-pleasing leadership

Uncharted Insider

The Insider - August 2023

On insurance, original thinking, main street businesses, and electrification

Uncharted Insider

The Insider - July 2023

On leadership, concept creep, and optimizations vs. goals, and family business

Uncharted Insider

The Insider - June 2023

On what needs to change, AI & the job market, climate fintech research, and Fes, Morocco.

Uncharted Insider

The Insider - May 2023

On defining reality, the pendulum swings of nuance, rising insurance premiums due to climate change, and a marriage ceremony

Uncharted Insider

The Insider - April 2023

The undertow of technology, over engineering process, asymmetrical risk, boring businesses, and rehearsal dinners.

Uncharted Insider

The Insider - February 2023

On artificial intelligence, remote work, the resilience of cities, and the limitations of climate tech

Uncharted Insider

The Insider - January 2023

On fast-food work cultures, the art of quitting, interest rates, and invisible supply chains

2022

The Insider - 9 Reflections on 2022

Looking back on 2022 with nine reflections

2022

The Insider - November 2022

On my next professional step, generative AI, our inability to build, and the power of honesty in art.

2022

The Insider - October 2022

The radical choice to take a sabbath every week

Uncharted Insider

The Insider - September 2022

On Patagonia, our relationship to time, sincerity, the 4-day workweek, and brothers

2022

The Insider - August 2022 (Future of Work edition)

On our obsession with productivity, the medium & the message, and trust in virtual spaces.

Uncharted Insider

The Insider - July 2022

On the burden of awareness, deconstructionist cultures inside organizations, and the 4-Day Workweek