My 50th blog post about why being spontaneous matters more than planning, featuring stories of biking to Facebook as a ninth grader, flying to San Diego in under an hour, and crawling through unmapped caves.
A dialogue between two builders exploring the overlooked frontiers of artificial intelligence: emotionally intelligent productivity software, personalized music creation tools, and memory-aware games.
A strange dream with two parts that somehow connected: starting in the world of Hollow Knight and ending in Japan, exploring themes of transition and borders.
Exploring how deep reinforcement learning and memory systems can make browser automation agents faster and more accurate, with insights on Composite and other web agent frameworks.
A comprehensive exploration of how to build powerful AI assistants through memory partitioning, goal-driven state transitions, graph-based retrieval, and multi-step prompting strategies.
A dream about adopting a cat from Instagram, the practical challenges of responsibility, and the weight of decisions made without thinking them through.
I met him on ome.tv: a fourteen-year-old kid from Phoenix who wanted to sell drugs. Then he asked me if I was content with who I am. This is that conversation.
Universities behave like nations, with endowments as dragon hoards and prestige as currency; smaller institutions can still outperform by focusing on what they do best.
A series of vivid dreams becomes a personal operating manual: step in earlier, choose nourishment over sparks and model the pause you want others to take.
How to future‑proof a company: hire for compounders, aim for orders of magnitude improvements and let product brilliance be the marketing.
Four traits for day‑one hires, and a twenty‑year lens on where leverage concentrates in AI and beyond.
A pragmatic synthesis: why Laplace's demon doesn't matter, how unpredictability arises from limited information and how meaningful choice emerges from framing and endorsement.
Future Jack writes to present Jack about seven lifetimes of projects, emotion‑capable robots, quantum moral algorithms and the importance of purpose.
Exploring nine archetypal lives — creator, voyager, AI architect, world‑builder, servant and more — and challenging myself to inhabit them instead of dreaming about them.
A look at why unconventional communities like hacker houses and East Campus feel like home, the psychology behind self‑selection and the risks of staying too long.
Twenty concise lessons drawn from YC's startup wisdom: team over idea, embrace pivots, recruit well, and focus on shipping, customers and culture.
A candid reflection on transferring from a complacent university to MIT: the grind, the shock of success, the hidden hardships and the path to acceptance.
Gratitude-filled reflections on humanity's slow arc of progress and what modern abundance unlocks.
An unfinished prologue introducing Jack and teeing up a deeper dive on learning outside college.
Mindset shifts and tactical habits for building an MIT-caliber education without the admissions letter.
A sweeping thought experiment on space, dimensions, time, existence, and the questions they raise.
Eighteen bite-sized lessons on relationships, focus, urgency, and owning your growth.