A breakthrough in machine learning would be worth ten Microsofts.
—Bill Gates1
While Katrina Lake liked to shop online, she knew the experience could be much better. The main problem: It was tough to find fashions that were personalized.
So began the inspiration for Stitch Fix, which Katrina launched in her Cambridge apartment while attending Harvard Business School in 2011 (by the way, the original name for the company was the less catchy “Rack Habit”). The site had a Q&A for its users—asking about size and fashion styles, just to name a few factors—and expert stylists ...