Tumbleweed bet that the internet could replace the overnight courier for contracts, statements and records. Plain email was far from safe for that work. Tumbleweed made software to deliver messages and files securely, with proof of receipt. When it filed to go public in the summer of 1999, banks and other regulated companies were looking for a way to trust the web with sensitive documents.

Proof It Arrived Intact

Jeffrey Smith and Jean-Christophe Bandini started Tumbleweed in the early 1990s. Their bet depended on one thing: making delivery secure and traceable. Tumbleweed's software encrypted messages, tracked delivery and gave both sides a record. That mattered in finance, health care and government. Those customers needed to prove that a message arrived intact, and to whom, which plain email could not do.

Bought by Axway

Tumbleweed priced at $12 a share in August 1999. It soared during the boom and fell hard in the crash. It shifted toward email security and secure file transfer, sold widely to banks and government agencies, and bought several rivals. In 2008 the French software company Axway, part of Sopra Group, bought Tumbleweed. Its products became part of Axway's secure file transfer and email security lines.

Cover: Wind-Swept Sands, William Merritt Chase. Art Institute of Chicago, public domain. Chosen for wind-swept sands (a tumbleweed carried by the wind).