Southwest Airlines had a disastrous holiday season, thanks in part to a software bug that left crews out of place and grounded thousands of flights. But Southwest isn't alone in having software in the headlines lately. The New York Stock Exchange recently had a software error that caused weird pricing on stocks and the FAA had its own computer issue that grounded planes earlier this month. So what's the deal with corporate software? Why do these crashes happen? And why does the user experience typically leave something to be desired? On this episode of the podcast we speak with Patrick McKenzie, an expert on engineering and infrastructure, who writes the Bits About Money newsletter and recently left payments company Stripe after six years. We talked about the challenges of keeping any software system alive after years of upgrades and updates, the distribution of tech talent across industries, and whether non-tech companies can close the gap with Silicon Valley.