Olin podcast features alumnus David Karandish on his fight for success

David Karandish’s Answers.com was a whopping success, but he was on the ropes 90 days after he began running it. How did his earlier startups teach him to take a punch?

Karandish is, by any standard, a massively successful entrepreneur. His most noteworthy transaction is the sale of Answers.com for $960 million—a “rounded unicorn,” he says, using startup shorthand for a billion-dollar deal.

But that success was hard-fought and made possible by a litany of failures and one unexpected disaster. Meanwhile, those failures—and that one big success—paved the way for what already promises to be another massive hit for Karandish, BSCS ’05. Capacity, his AI-driven customer support platform has been on a tear.

Our story hinges on a two-hour period in 2011, 90 days after David—at age 26—and his partners had engineered the merger of their company with Answers.com, taking the once-public Answers private. That day, David’s team watched the traffic drain from their site in the wake of a change in Google’s search algorithms. “Our $127 million acquisition went unprofitable in about two hours,” he said.

This is the story of what led to that moment, how David and his team responded, what in his history informed that response and how he’s carried those lessons into his next chapter with Capacity.

Along the way, we learn something about the difficulty of thinking in terms of failure—though failure was the fate of his first six startups. We learn about the danger of taking customer acquisition for granted. We learn how a successful entrepreneur can roll up the lessons into one more big win.

And we begin to understand why it’s so important to learn how to take a punch.

Listen to this episode of On Principle.