He may have nearly been fired from his own startup, worked as a bicycle messenger, and been told to “get a job” while writing a novel, but Glenn Kelman’s experimentation eventually led to his appointment as a technology company’s CEO, he told a crowd of more than 50 at a Morse College Master’s Tea on Thursday.

In a talk titled “From English Major to Tech CEO,” Kelman discussed topics ranging from his upbringing to tips for anyone looking to start a company. Kelman, who earned his degree in English from the University of California, Berkeley, used anecdotes from his time as a CEO of the technology startup Redfin, an online real estate firm, to emphasize the importance of being genuine with other people, taking risks and being “tough.”

“I’m not a genius, so all I can be is tough,” Kelman said.

Moving around the room energetically, Kelman recounted the unconventional path of his career. After college, he spent a year attempting to write a novel before taking a job as a bike messenger. A bad crash, however, caused him to hang up the bike and interview with investment banks, consulting firms and a small tech start-up called Stanford Technology Group. Although larger firms offered him higher pay, Kelman decided to join the startup, quipping that “on the brink of selling out [he] had one more chance to twist the knife.”

Kelman encouraged the seniors in the room to pursue “creative” professions where they can build something new, rather than analytical ones, adding that they should find a job in which they will “lose all sense of time.”

After a few years at Stanford Technology Group, Kelman created his own Internet startup, Plumtree Software, which was “one of the first innovators in the portal market,” according to Morse College Master Amy Hungerford. After leaving Plumtree to take care of his sick older brother, Kelman nearly chose to go to medical school, citing how inspired he was by doctors who refused to give up on his brother. After deliberating for months, however, he elected to take his current job at Redfin.

Kelman said his experiences have shown him the necessity of pursuing only good ideas and recognizing weaknesses in oneself.

“I never fake knowing something,” he said. “Figure out what your bad thing is and go after it.”

Kelman’s “harrowing” upbringing gave him confidence and resilience on which he would later draw, he added, citing time spent as the only Jew at an Evangelical Christian summer camp and the conviction of his older brother for a violent felony. He stated that he hoped his talk would give students “the confidence to do [their] own thing.”

Two students in attendance interviewed said they found Kelman’s advice helpful.

“I came here because I wanted to find out the kind of characters behind really amazing people,” Alex Meeks ’14 said. “And I got that.”

Redfin officially launched in 2006, one year after Kelman joined the firm.