Joseph Anthony Liemandt

In the 1990s Liemandt was the golden boy of enterprise software, a 30 Under 30 wunderkind before there was a Forbes 30 Under 30 list. Like Bill Gates before him, he dropped out of college, in his case Stanford, to start a company, Trilogy, and build his fortune. In 1996, at the age of 27, he made the cover of Forbes, and a few months later he appeared as the youngest self-made member of The Forbes 400, with a $500 million net worth. Trilogy Development Group sold product configuration and sales software to the likes of Hewlett-Packard and Boeing. Trilogy became the hot place for young coders to land in the late 1990s. Known for its testosterone-fueled work environment and an alcohol-infused mix of long hours, fast cars, gambling and sex, Trilogy served as the model for Silicon Valley’s boys club. Its programmers were paid like rock stars and partied like them, too. The new version of Trilogy is now part of ESW Capital, Liemandt’s Austin private equity firm. After the dot-com crash, Trilogy faded from view, but from its ranks numerous successful tech companies, including Nutanix and SendGrid, were spawned. It also played a big part in Austin’s emergence as a technology hub. Like others with dot-com fortunes, Liemandt dropped off The Forbes 400 in 2001. In 2006 he quietly began building an enterprise software empire where innovation and growth take a back seat to sheer profitability. Using his closely held ESW Capital, Liemandt began buying dozens of business-software firms with values ranging from $10 million to $250 million. Liemandt’s team was on a quest for the regular income streams associated with sticky software maintenance contracts. To cut costs, R&D and employee benefits were to be gutted. And as a sweetener, he began assembling a patent-litigation war chest. For the founders and shareholders of the middle-aged firms that are ESW’s targets, Liemandt offers quick cash: There are no earn-outs or contingencies, and the deals typically close within 45 days. For the rank and file it’s a different story. Most are replaced by cheaper overseas talent. At age 50 he’s back on The Forbes 400, with a net worth of $3 billion. The young Liemandt seemed destined for business success. His father, Gregory, worked directly under legendary GE executive Jack Welch, and the Liemandts vacationed with the Welches. After his father left GE to be CEO of a mainframe software company in Dallas in 1983, Liemandt began programming but also took a strong interest in entrepreneurship, frequently reading the business plans his father brought home. As a Stanford economics major, he was determined to create the kind of business that either Jack Welch or his father would want to buy. His obsession with sales efficiency spawned Trilogy, and in 1990, at age 21, he defied his parents’ wishes and dropped out of Stanford to build his software company.