Growing up, Laurie Segall felt like she didn’t fit perfectly anywhere. As her high school newspaper editor, she always found herself writing about the odd and outcasted. But it’s probably her keen sense of what’s weird, interesting, and emerging that has made her an award-winning investigative reporter and the founder of Dot Dot Dot, a media company focused on onboarding the mainstream into a new era of the internet, Web3.

Beginning in 2008 at 23 as a newly minted assistant at CNN and as Wall Street was crashing down, she began discovering a group of scrappy misfits rising from the ashes of the recession to change the world: the tech entrepreneurs. Seeing this space as an area no one at CNN was covering, she wrote a job description and pitched it. Over a decade, Laurie became one of the first reporters to give airtime to many of these founders—from Mark Zuckerberg and Jack Dorsey to Kevin Systrom and Travis Kalanick —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. She 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. Her book, Special Characters: My Adventures with Tech’s Titans and Misfits is a memoir detailing her career journey with early access to some of the most influential people in the world during a time when they still answered their own phones.

In this episode, Laurie shares her rise in investigative journalism, her struggles with the silent death of a thousand cuts of sexism in her industry, and how she learned to fight for what she knew was rightly hers. She shares that to be successful at something, you must immerse yourself in it, have the guts to ask for what you want when an opportunity presents itself, say yes, and learn how to tackle it as you go along.