A shopper with a question on a website in 2000 had to call a phone number or send an email, then wait. LivePerson put a chat button on the page so a real person could answer right away. Robert LoCascio founded the New York company in 1995. Companies paid a monthly fee for each agent. It went public in April 2000, just weeks after the Nasdaq peak, with a product that few companies yet knew they needed.

Several Chats at Once

LivePerson bet that live conversation would let websites sell more and serve customers better. Its chat software was hosted, so companies could add it without new servers. Online retailers, banks and telecom companies became major customers. Each agent could handle several chats at once, which saved money for its clients. Later the company moved from website chat to messaging across apps and channels, and added automated assistants.

Below a Dollar, Then Back

LivePerson priced its IPO at $8 a share in April 2000 and listed on Nasdaq. In the crash that followed, its shares fell below $1. The company cut costs and held on. It grew steadily through the 2000s and 2010s, as the chat window became a normal part of shopping and banking online. LivePerson is still public and trades as LPSN.

Cover: The Conversation, Marcellin Gilbert Desboutin. Art Institute of Chicago, public domain. Chosen for a conversation between two people.