From the first moments of his lecture in Gonda Theater, Chris Sacca (SFS ’97, LAW ’00) made it clear to his audience of more than 100 students that he was not the stereotypical, hyper-successful Georgetown graduate.

The influential venture capitalist and Internet entrepreneur, dressed in jeans and a cowboy shirt and looking, as he joked, like an “unemployed rodeo clown,” began by poking fun at his own credentials.

After explaining how he had led the third floor of New South in noise violations during his freshman year and a march to protest the closure of a student pub located in Healy Hall, he admitted with a laugh: “You’re probably wondering, `Who the hell is this guy to be giving us advice on how to spend our four years at Georgetown?'”

His path after graduating from the university was also quite unconventional. He went to law school, he said, in order to use his student loans to fund an Internet startup, and he even managed a short run as a multimillionaire day trader. But by graduation, he said, he had lost everything.

“That left me 25 years old and $4 million in debt …” he said in an interview. “So I had to get a job and actually be one of those sellout corporate lawyers in Silicon Valley.”

Yet Sacca rose quickly through the Silicon Valley entrepreneurial community, and ended up as a top executive at Google. After stepping down in 2007, he became a venture capitalist and made an early investment in Twitter

With his credibility unscathed by his initial round of self-deprecating humor, his lecture soon turned earnest. With a smile, he laid out a challenge to his audience. “By placing your butt in [your] chair … you’ve agreed to be totally awesome,” he said. “You’ve committed to continue that awesome throughout all of your years here. You’ve committed to race in this perpetual race to always be tied for first place as the most legitimate Hoya here.”

And for the rest of his hour on stage, he blended advice and anecdotes in a breakneck attempt to explain how to do just that.

He addressed everything from the dangers of being a slave to email to the importance of the liberal arts.

“Learn with a capital L,” he advised. “This is your chance to study the humanities, to dive into theology, to grapple with the deep issues, the basement fundamental issues of philosophy and questions of suffering and healing – to know the human condition.”

The lecture earned positive reviews from students. Mishay Kalan (MSB ’14) said she was impressed by “his vision of life – not just to make money, but to be interesting and to really be with the people around you.”

Shavonnia Corbin-Johnson (SFS ’14) was ready to take his advice on the importance of fresh starts. “Being a freshman here, it’s hard to adjust,” she said. “It made me think maybe I can restart my freshman year and make it really good.”

Sacca ended with another exhortation. “The more you learn now and train later, the more you’ll discover everything that people around you have to offer and,” he said, “the more eager I’ll be to actually hire you.”