“That is the stupidest thing I’ve ever heard. You have no idea how hard it is.”

Nirav Tolia
Co-Founder and Former CEO, Nextdoor
Executive Chairman, Hedosophia
… recalling Yahoo! Co-Founder Jerry Yang’s response when Tolia—employee No. 84—left to pursue his own entrepreneurial path.

In the early days of the Internet boom in the mid-1990s, Nirav Tolia was among the first employees hired at Yahoo!, an early Internet portal that came to dominate the web in its heyday. During Tolia’s three years at Yahoo!, the startup’s valuation rocketed from $100 million to $100 billion.

But in 1999, amidst Yahoo!‘s meteoric rise, Tolia decided to strike out to start his own venture, he recalled in a recent talk at Dallas Startup Week.

During a talk at Dallas Startup Week, Tolia shared: “I remember at my going-away party, one of the Yahoo! co-founders, Jerry [Yang], came to me and said, ‘Now, tell me again why you’re leaving?’”

In response, Tolia explained to Yang that reflecting on his time at Yahoo! over the past three years was “incredible”—and witnessing the astronomical growth of the company firsthand made him feel like he won the lottery.

But, he told Yang, “Now I want to try to do it myself. I want to be a person who can create a Yahoo!.’

“And he looked at me and said, ‘That is the stupidest thing I’ve ever heard. You have no idea how hard it is. When you fail, you can come back here and work.’”

It was said “in a kind of avuncular, supportive way,” Tolia said, and he thought Yang might be “absolutely right.” But after seeing the company’s success, “it gave me the courage to want to do it myself.”

It was just the beginning for Tolia.

Over the next two decades, he founded and scaled multiple consumer companies, including co-founding the review site Epinions in 1999. Epinions merged with Dealtime to form Shopping.com, which had a successful IPO in 2004 and was acquired in 2005 by eBay for $620 million. Venturebeat described it as a “post-bubble success story.” In 2008, Tolia co-founded Nextdoor, the neighborhood-focused social network that went public in 2021, which he led as CEO for years.

Today, Tolia lives in Dallas’ Park Cities neighborhood and serves as executive chairman of Hedosophia, a leading technology investment firm. Moving from the West Coast to the Dallas region in 2021, the entrepreneur and investor is eager to foster the next generation of founders by sharing lessons from his pioneering days.

Earlier this month, Tolia and his wife Megha Tolia, President and COO of television production company Shondaland, were named co-founding directors of SMU’s William S. Spears Institute for Entrepreneurial Leadership.

At Dallas Startup Week 2023, Tolia recounted his journey from Yahoo! pioneer to tech entrepreneur during a talk with Capital One’s Kamlesh Talreja.

Read more about the tech entrepreneur’s advice for entrepreneurs in Glenn Hunter’s Dallas Innovates story.

For more of who said what about all things North Texas, check out Every Last Word.

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