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Reading List for Leaders in Uncertain Times

Editor’s note: Here are some of our best pieces on leadership, grit, and managing a startup in times of uncertainty, culled from our past (almost) decade of archives.

Leadership is about more than management — there’s also passion, humor, and resilience. Dick Costolo, entrepreneur and former CEO of Twitter, talks with a16z General Partner Peter Levine about the role of improv and imagery in leadership moments big and small.

From becoming the youngest assistant secretary of state to her role as US Ambassador to the United Nations, Ambassador Susan Rice has learned what it means to drive forward in the face of challenges. In this discussion with a16z General Partner Kathryn Haun, Susan reflects on the many lessons she’s learned throughout her career, including how to be a tough yet compassionate leader in times of crisis.

When a16z General Partner David Ulevitch founded OpenDNS, little did he know the rollercoaster he had just boarded. From CEO to CTO back to CEO, from consumer to enterprise, from being acquired (by Cisco in 2015) to being the acquirer, David shares his journey and advice for founders–not least of which relates to how you manage your own psychology, and learn how to trust your leadership, in times of change.

Dapper Dan is known for having pioneered high-end streetwear in the 1980s, but his story as a founder, gambler, and lifelong learner–hustler–who keeps reinventing himself through hard times has lessons for other makers and leaders.

Many smart businesses know that they could get disrupted, and yet it happens anyways–why? Clay Christensen, the author of The Innovator’s Dilemma, Harvard Business School Professor and the pioneer behind disruption theory, and a16z co-founder Marc Andreessen discuss the theories and frameworks that can help companies survive, in this conversation led by longtime tech writer and editor Steven Levy.

The hardest thing about the proverbial “pivot” isn’t just the actual pivot. It’s the courage to make the decision … and being honest with yourself as a CEO. In this conversation with a16z’s editor in chief Sonal Chokshi, Ben and Jason Rosenthal, the former CEO of Lytro (acquired by Google) discuss pivots and their wide-ranging impact on every aspect of a startup.

Every organization (and indeed, every individual) makes decisions every day under conditions of uncertainty. Annie Duke, the author of Thinking in Bets and a world-class professional poker player, talks with Marc and Sonal about thinking systematically about that uncertainty and how to use it to make better decisions.

What do the numbers — both in financial statements and KPIs — tell you? And what do they not? This episode covers the most common mistakes people make when it comes to understanding their numbers; how investors look at a company’s P&L; what metrics investors use to determine if a business is healthy; and how founders can use the numbers to navigate in times of crisis.

Balancing cash reserves vs. growth, advance planning vs. constantly changing strategy, revenue vs. margin, coordination/communication/culture, and so on is a lot harder than it seems on a finance spreadsheet. And this is why a tight, productive partnership between CEO and CFO is so important.

How do you handle a crisis? In this episode with a16z Operating Partner for Marketing, Margit Wennmachers, and marketing partner Kim Milosevich talk with Sonal about the process, mindsets, and tactics for handling a crisis and ultimately, become a better company for it.

In many ways, managing startups is about managing uncertainty. So what happens when changes in the business require changes — and sometimes reductions — in the workforce? a16z Operating Partner Shannon Schiltz and a16z General Partner Alex Rampell share both their professional and personal experiences with layoffs — from why they happen to what to do (and what not to do).