They built YouTube: Former execs recall the pirate early days, pivotal wins, and big headaches over its 20 years

Shishir Mehrotra, formerly YouTube's chief product officer — and now CEO of Grammarly — said the company faced adversity early on, initially perceived as "Google's first failed acquisition" following the companies that would become Google Maps and Android.

"Grainy videos didn't really make sense in the Google ecosystem," Mehrotra said. He likened early employees to "pirates" who believed deeply in their mission.

One idea that helped Mehrotra land the job was a pitch for "skippable ads" — a pricier format where advertisers would only pay when an ad wasn't skipped. But the sales team hated the idea because of the name, and it didn't ship for years — until a product manager suggested the name TrueView.

"It went from zero to a billion dollars in about 18 months," Mehrotra said — "one of the fastest-growing products in Google history."

Another one of his proudest leadership moments came at a company offsite in 2012, when he said YouTube was struggling for relevance and purpose. To combat the stagnation, he set a lofty goal of 1 billion hours of daily watch-time, which "reverberated through Google" until it was surpassed in 2017.

Susanne Daniels, YouTube's former global head of original content, looks back proudly at the content output during her tenure — from Doug Liman's "Impulse" and "Cobra Kai" to collaborating with YouTubers Liza Koshy and Joey Graceffa on original series.

YouTube Originals went through several strategies — including subscription and ad-based models, and a pivot from scripted to unscripted programming in 2019, Variety reported — before dissolving in 2022.

Daniels said she found the number of pivots frustrating, and said the biggest challenge was that YouTube operates as a technology company rather than a media business. Its success as a distribution platform for user-generated content meant it didn't necessarily need to play the long game of original content.

"YouTube Originals was a square peg in a round hole — constantly having to pave roads where there already should have been — from production issues to business deal issues and everything in between," she said. "We never had the support system internally nor the resources we needed to succeed — not to mention a crushingly limited budget for production and marketing."

But Daniels said she was inspired by her team and felt she could have made YouTube Originals a valuable asset with more support.

"It was definitely a unique and rewarding experience in many ways," she said.

A YouTube spokesperson said that while Originals served to turbocharge its content ecosystem, the creator community has now evolved to produce increasingly sophisticated content.

The company is still in the business of original content, the spokesperson argued, by investing directly in its community of creators and artists.

Malik Ducard — currently the chief content officer at Pinterest — last served as YouTube's global head of learning, social impact, health, family, and film & TV.

During his time, he also spearheaded initiatives for underrepresented communities, like the $100 million #YouTubeBlack Voices Fund, which gave seed funding and other resources to Black creators.

Ducard said that during his time at YouTube, he felt lucky to be in the orbit of late CEO Susan Wojcicki.

She was "the definition of calm in the storm," Ducard said, given that there were many "heightened moments at YouTube and there was never a heightened Susan."

"She was always steady on the wheel and someone that people sought out for guidance," he added.

And YouTube's investment in educational and family content — including YouTube Kids, which Ducard's then-five-year-old son was one of the first users to test — was part of Wojcicki's "push to really see that YouTube has a responsible place in the world."

Entrepreneur and investor Hunter Walk served as director of product management at parent company Google.

At YouTube, his proudest achievement was "nailing the shift to mobile," he told BI, which required overstaffing the mobile division ahead of its maturity and contending with the fact that "some notable executives at Google tried to kill our deal to be a default app on the iPhone."

One of the biggest challenges was building YouTube's copyright tools. Rather than removing copyrighted content, Content ID lets rights holders choose to keep it up and monetize. It was a counterintuitive strategy at the time that took some convincing.

"If they understood this was basically fans doing their distribution work for them, we could leave it up, monetize it, and everyone would profit," Walk said. "Fortunately, over time, it came to be viewed this way by the majority of media companies."

Matt Koval was an early YouTuber hired by Google in 2012 to compile best practices for creators that the company could use as scalable resources.

"Back then, it sounded crazy that YouTube creators would become Google employees," he said.

Eventually, Koval was named YouTube's first creator liaison, serving as a conduit between those inside and outside the company. The idea came from Alphabet CEO Sundar Pichai, inspired by the success of search liaison Danny Sullivan, Koval said.

In navigating various controversies, Koval felt he was able to "land" his explanations. But it could be a tricky line. The biggest backlash came when he sought to explain YouTube's decision to eliminate the dislike button, which trolls were using to target marginalized groups.

"Google security got involved" in the face of personal threats, Koval said. And while the fervor eventually subsided, he said the role could occasionally feel like flying too close to the sun.

As the mother of a 10-year-old who dreams of becoming a content creator, Rachel Melby said she's been reflecting on her time at YouTube amid a slew of documentaries about the perils of family vlogging.

"It's kind of radical to think that there was a time when people were not incentivized by money to create content and put it out into the world," she said.

Melby, the former global lead for influencer and celebrity partnerships, said struggles around kids' content moderation led to her departure. At the time, YouTube was contending with controversial family vloggers accused of exploiting their children for profit, she said.

"It just became too hard for me to sit and have these conversations about kids," she said.

Melby recently helped her son post his first YouTube video, but she's ensuring he proceeds with caution.

"It's just one part of our life," she said. "I don't want it to be all-consuming."

A YouTube spokesperson said the company has always tried to ensure the safety of children and families and has adjusted its products and policies accordingly.

Kathleen Grace arrived at YouTube through its acquisition of Next New Networks, along with Relles and former TikTok COO Vee Pappas. She said the company felt like a startup at the time, like "Google's punk rock little brother."

During her tenure, Grace helped open YouTube's first Spaces: free production facilities and networking hubs across the globe. The aim was to "humanize the scale of the company," and seed a community in Los Angeles, New York, London, and Tokyo.

YouTube shuttered the Spaces during the pandemic, and Grace said she's not sure they make sense in today's world, where social video has become increasingly lightweight, and the need for community has shifted as more people want to be creators.

"It's just a different era," she said. "You don't feel as lonely."