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AppNexus Engineering@Scale: 3 Failures and 1 (BIG) Success

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AppNexus Co-Founder and CEO Brian O’Kelley has built one of New York’s greatest startup successes. While AppNexus exploded on the scene and never looked back, the making of Brian O’Kelley involved more than a few setbacks. In this recent Engineering@Scale talk, Brian lifts the hood on how his many failures led to one big success.

Getting hooked
Brian got his first taste of being an entrepreneur as a high school senior in Eugene, Oregon. Unsurprisingly, it involved computers.

His school district had about five hundred Apple 2 computers that they were upgrading to Macs. (Keep in mind that this was the ‘90s.) When Brian asked what was going to happen to the old Apples, the school district offered to sell him the lot for $5 a pop. It was a no-brainer: Brian and a few buddies resold them for $100 each.

This first brush with entrepreneurial success got him hooked and Brian still calls it the best deal he ever made.

If at first you don’t succeed, fail, fail again
Upon graduating from Princeton as a Computer Science major, Brian moved out to LA to launch LA2Nite, a hip new e-ticketing service.

LA2Nite had a few million in angel investor money. It also had an unreliable revenue model, a terrible marketing strategy, and a major competitor in TicketMaster. Needless to say, this was Brian’s first failure. Five months after graduation, Brian was fired as CEO and found himself living in his parents’ basement.

That’s when he discovered that failing is an opportunity for learning. Getting fired helped Brian build a roadmap for how to get better at what he was bad at, without ever having to go to business school or climb a corporate hierarchy.

Brian went on to have two more important failures. First he joined an experienced mentor at a startup consultancy where he wound up personalizing web interfaces for AmEx. The software Brian built is still running today but the firm tanked and Brian got fired – again.

Next he joined an internal startup but when the CFO of the parent company decided not to back the startup, Brian “quit in a huff.” He wasn’t about to be fired for a third time.

A big success
After three failures, Brian was finally able to funnel all of his hard-earned lessons into one big success at Right Media. He joined Right Media as a coder and began writing real-time personalization advertising. The ad world wasn’t using personalization at the time, so Brian translated his experience consulting for AmEx into online advertising.

Brian quickly became the head of business development, drawing on the lessons he learned from LA2Nite’sfailed business model to successfully guide Right Media. He then became the CTO and pushed the company to pivot into the tech space, selling the predictive ad system he had helped to create. This turned out to be the future of Right Media, which Yahoo! purchased for $850 million. Finally, Brian O’Kelley had his big success.

Brian ends his talk by saying that “if you can’t fail, you can’t learn”. His not-so-immaculate conception as an entrepreneur takes that idea one step further: if you can’t fail, you can’t succeed.

Brian’s recommended reading: The Four Steps to the Epiphany by Steve Blank.