A few weeks ago, the Cedar team and guests packed into our NYC office for Cedar Talks, featuring Brian O’Kelley, founder and former CEO of AppNexus. Cedar Talks is a thought leadership series focused on connecting the Cedar team and broader community with tech entrepreneurs who are dedicated to solving hard problems with great design, thoughtful engineering and industry expertise.

O’Kelley is well known for his role in building AppNexus into one of the most successful startups in New York history and has been labeled the “new king of ad-tech” by Forbes. His talk was full of useful career insights, but the following three (in particular) bear repeating:

#1: Ask the dumb questions

After being laid-off from a small startup early in his career, O’Kelley found himself living in his dad’s basement and collecting unemployment benefits. He stumbled into the ad-tech world when he took a job writing code for a small company called Right Media. Knowing nothing about the advertising industry, he just kept asking “a series of dumb questions” and proposing new ways to do things. O’Kelley recalled that this was how he “stumbled on the idea of an ad exchange, where in real-time, in the blink of an eye…we could auction off thousands of advertisements and produce better results than you could the old-fashioned way. It just grew like a weed because the outcomes were better for everybody.” At Right Media, O’Kelley helped invent a platform that changed the fundamentals of the advertising industry and made a huge impact to the established players – just four years later, the company was acquired by Yahoo! for $680 million.

Just a few months later, O’Kelley founded AppNexus which disrupted the advertising industry once again and was acquired by AT&T for $1.6 billion in 2018. When asked how he was able to disrupt the same industry twice, O’Kelley pointed to his own motivations: “I just wanted to build stuff. I think that attitude has been really good for me in my career where my motivation has never been about money or equity; it’s always been about asking how to solve really hard problems. And how can you ask the questions that get to the right answers.”

#2: Build an inclusive culture

In reflecting on the 11 years he spent scaling AppNexus from a small startup to a large company, O’Kelley spoke of the importance of reshaping core values as the company changed and matured – in particular, putting a sustained focus on diversity and inclusion. He noticed a pattern where women and underrepresented minorities were being passed over for promotions and he took responsibility for fixing it. He decided to only mentor women and diverse employees at the company, since those were the groups for whom executive mentorship was often hard to obtain. Many of his former mentees grew to become the next generation of leadership at AppNexus and are still leading the company today. O’Kelley made inclusion a key tenant of the company culture and personally wanted to ensure that people of all backgrounds felt represented and included. Today, O’Kelley continues this commitment by mentoring underrepresented founders in the NYC startup space.

#3: Focus on making things better (not perfect)

Throughout his career, O’Kelley has been at the forefront of modernizing the way that consumers receive digital advertisements. Critics would contend that the ad-tech revolution has brought mixed results for consumers; while people now tend to receive ads more relevant to their interests, their privacy has been compromised. O’Kelley acknowledged that “privacy implications of the current advertising ecosystem are pretty scary.” However, as he reflected on the overall legacy of his work, O’Kelley rejected framing it as simply good or bad and instead pointed to incremental progress as the positive outcome. “If you get rid of advertising, you destroy the internet…[So we should not just say] ‘make advertising illegal’ because in doing so we would lose a lot of other pieces.” In a similar vein, he frames his approach to building startups in terms of progress, not perfection: “We need to be in the mindset of better, not perfect…What things can we do to preserve our business but make it incrementally better over time?”

The pursuit of making things better has led O’Kelley to create two transformational businesses over his career and he’s leaving the door open for additional ventures in the future—but first a well-deserved break to focus on a personal life challenge: mastering Italian in Italy. Ciao!

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