My Adventures With Tech Titans & Misfits

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In 2008, 23-year-old Laurie Segall was a newly minted assistant at CNN and was living in an East Village walk-up apartment. As Wall Street was crashing down, Segall began discovering a group of scrappy misfits who were rising from the ashes of the recession to change the world: the tech entrepreneurs. A misfit herself, Segall gained entrance to New York’s burgeoning tech scene, with its limitless cash flow and parties populated by geeks-turned-billionaires. Back at the news desk, she rose through the ranks at CNN, while these entrepreneurs went from minnows to sharks, building companies that would become our democracy and our social fabric: Facebook, Twitter, Instagram, Uber, Tinder.

Over the course of a decade, Laurie Segall became one of the first reporters to give airtime to many of these founders—from Mark Zuckerberg (Facebook) to Jack Dorsey (Twitter) to Kevin Systrom (Instagram) to Travis Kalanick (Uber)—while tracking their evolution and society’s cultural shift in the CNN startup beat she created. By the end of her tenure at CNN, she had become its on-air senior technology correspondent and had witnessed the rise of second-wave tech, from the boom to the “complicated years” to the backlash, as her misfits emerged as some of the world’s most influential leaders.

Join Ladies Get Paid author and founder Claire Wasserman for an interview with Laurie about her recent book, Special Characters: My Adventures with Tech’s Titans and Misfits.

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Claire Wasserman with Laurie Segall

Key Takeaways:

  • An inside look at CNN, the culture, and the major players as the network transitioned over the course of a decade
  • Specifics around death by a thousand cuts sexism, both in media and tech
  • A look behind the curtain at Mark Zuckerberg during Facebook’s first scandal: Cambridge Analytica (and everything before and since then)
  • An inside look at the other side of Silicon Valley: high tech sex parties and a secret dominatrix dungeon where they lock up Apple engineers for “creative inspiration”
  • The importance of mentorship in her life
  • Behind the scenes with some of the most well-known tech titans: i.e. Mark Zuckerberg and Jack Dorsey
  • Impostor syndrome, and how she often had to figure out ways to work around the system
  • The links behind entrepreneurs and depression – we often hear about the big wins, but not the heavy losses
  • The Future of AI and the ethical implications
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About Laurie Segall

Laurie Segall is the Founder and CEO of Dot Dot Dot, a news and entertainment company that explores the intersection of tech and humanity. Recently, the company launched D3—a network aimed at onboarding the mainstream into a new era of the internet, Web3. Segall is also the host of First Contact, an original podcast series that explores the people and technology changing what it means to be human. The series is produced by Dot Dot Dot Media and distributed by iHeartMedia.

An award-winning journalist, Segall’s work explores technology through the most important lens: the human one. As CNN’s former senior technology correspondent and the editor-at-large for CNN Tech, she covered the intersection of technology and culture for more than a decade. Segall was also a correspondent at 60 Minutes, focusing her on extremism in the United States.

Segall first gained notoriety by identifying and interviewing founders of disruptive tech companies and bringing their stories to light. Her unique reporting style led to interviews with the world’s most influential leaders and entrepreneurs, including Mark Zuckerberg, Tim Cook, Jack Dorsey, and Bill Gates. Her access to the titans of tech has allowed her to give audiences a behind-the-scenes look at companies like Facebook, Instagram, Twitter and Uber during their meteoritic rise.

Segall served as executive producer and host of CNN Go’s first original series, Mostly Human with Laurie Segall, a six-part investigative docu-series that explored sex, love, death, and humanity – through the lens of tech. Her last documentary for CNN, Facebook at 15: It’s Complicated provided unprecedented access to Facebook and its top executives, including CEO Mark Zuckerberg and COO Sheryl Sandberg.

Segall has won numerous awards for her work championing women, including a Gracie Award for her docuseries Revenge Porn: The War on Women, which shed light on an alarming type of cyber harassment aimed at women. She’s also received multiple EPPY Awards, including one for Money, Power, and Sexual Harassment, a series that gave victims of sexual harassment a platform to speak out.

She interviews the tech billionaires, but has committed her career to covering those impacted by their code.

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