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Outlier’s Path

Stripe Press has earned wide praise for its mission and the quality of its books. They are beautifully designed to speak to the “innately curious, to “the tinkerers and builders” drawn to ideas that challenge and provoke. After browsing their site, I ended up buying almost all of their titles.

Over the weekend, I found myself flipping through Brian Potter’s The Origins of Efficiency. As a former COO/CFO of Zappos, efficiency is a topic close to home. Initially, I decided to write about efficiency as many founders begin their 2026 planning, but somewhere along the way, I took a detour.

When founders and investors talk about focus, they usually mean saying no and narrowing in on what matters most. That discipline is the foundation of efficiency. In a world where technology, capital, and talent move faster than ever, focus alone may not be enough. The most resilient companies do not just narrow. They adapt and build optionality into their culture, enabling them to change direction without losing velocity.

Optionality is not a license to do everything. It is the discipline of keeping the door open to do the right thing later. It is how Amazon evolved from selling books to running cloud infrastructure, and why the startups that survived COVID, the dot-com bust, and the financial crisis were not necessarily those with perfect plans but those with flexible ones that embraced scenario planning. They built for multiple futures instead of betting on a single one.

Outlier founders understand that uncertainty is a permanent condition of the world. They design systems that work across many futures. They build teams that can reconfigure, cultures that embrace experiments, and products that can bend without breaking. Optionality is how they stay on the path, even when the path changes or disappears entirely.

Our obsession with efficiency need not kill optionality, but it does require slack, which is the margin where discovery happens. Time to think. Capital held in reserve. Space for curiosity. They are not a waste of resources. They make resilience possible. Founders who survive crises are not necessarily more intelligent or more efficient. They ensure their companies are not overextended. In a complex world, perfection is brittle. Resilience depends on our ability to stretch, absorb stress, and recover.

As we plan for 2026 and beyond, remember that building an enduring company is not about playing the finite game of quarterly targets or short-term efficiency. It is about playing the infinite game, balancing focus with flexibility and efficiency with adaptability.

In the short run, efficiency builds momentum. In the long run, optionality ensures survival. Together, efficiency and optionality create endurance.