Navigating uncertain economic conditions is part and parcel of running a business. Yet, throughout challenging times, it’s critical that startups stay committed to continually pushing the possibilities of what technology can deliver, says Stripe CEO Patrick Collison. That means leading with the guiding principle “micro pessimism and macro optimism.” Often, Collison says, this means having a relentless ability to be critical about the state of technology (including one’s own products) while still believing in its possibilities.That viewpoint acknowledges the structural tension companies face when trying to innovate in the context of economic reality, and can be the difference between persisting through challenging times or becoming a casualty of yet another tech boom and bust cycle. Collison joined Greylock general partner Reid Hoffman on our Iconversations speaker series to discuss Stripe’s early days and its evolution into the payment and financial services platform giant it is today, and his advice to startups for navigating the predictable unpredictability of business. You can read the transcript for this interview here: https://greylock.com/greymatter/micro-pessimism-macro-optimism/ Chapters 0:00 Introduction 0:17 Hamster of Scale 1:47 Being an Entrepreneur 5:42 Navigating Difficult Times 7:14 Founding Stripe 10:40 Micro Pessimism, Macro Optimism 12:41 Evolution of the Internet 15:49 Market Cycles 17:56 Progress Studies 21:27 Underrated Technologies 24:13 Co-Founders’ Relationship 26:42 Journey of Founding Stripe 28:54 Leadership Style