The Martha’s Vineyard Book Festival kicked off Friday evening at the Chilmark Community Center with a conversation between comedian and late night host Seth Meyers and top tech journalist Kara Swisher before a sold-out crowd of community members, sponsors and the festival’s featured authors.

Interviewing Ms. Swisher, Mr. Meyers focused his questions on evolving developments in tech ­— principally artificial intelligence — and the art of interviewing. In addition to her position as editor-at-large of New York Magazine, Ms. Swisher co-hosts the podcast Pivot, which divulges urgent and developing stories in tech, business and politics, and hosts On with Kara Swisher, in which she interviews some of the world’s most powerful people, asking questions Mr. Meyers called “tough but fair.”

The opening event signaled the start of the book festival, which features 27 authors across genres, and is free to the public on Saturday and Sunday.

On Saturday, authors take part in six panels to discuss topical issues from violence and justice to dynasty and wealth to reckoning with identity through memoir. Sunday gives each author the chance to speak about their own book in one-on-one interviews.

Opening event sold out quickly. — Ray Ewing

All books are available for purchase over both days of the festival, and the authors will host signings after their discussions.

The event strives to bring writers from a wide range of expertise and experience into discussion with each other to parse through the relevant themes across their books. Friday evening's conversation about artificial intelligence continued on Saturday morning during a panel called AI and the Future of Writing which featured authors Geraldine Brooks and Rebecca Makkai, journalist and producer Jacob Weisberg and journalist Ben Smith. Extending her conversation with Mr. Meyers from the previous evening, Ms. Swisher moderated the discussion, asking each of the panelists for their views on changes in their respective fields as AI becomes more prevalent, accessible and sophisticated.

On Friday, Ms. Swisher and Mr. Meyers touched on similar ideas while covering a wide range of subjects in a fast-paced rapport of wit and wisdom. Ms. Swisher encouraged embracing technological advancements, but she issued a stern warning about a world without online regulation.

“I’m not a big regulatory person, but Wall Street has legislation, and maybe it’s broken in some ways but health care, pharmaceuticals, planes — everybody has legislation in some fashion,” she said. “Tech has none. Zero around algorithms, around privacy, around antitrust, around anything.”

Ms. Swisher said that the federal government should pass a national privacy bill to protect its citizens as social media, technology and artificial intelligence continue permeating every layer of society. She also called for updated antitrust laws and an increase in small companies developing tools such as AI to increase innovation and compete with tech giants.

Book festival founder and director Suellen Lazarus. — Ray Ewing

“[Your phone] is a surveillance device,” she said. “In the wrong hands of the wrong people, it’s terrifying. Dictators love the internet. Dictators love iPhones. They love all this stuff because they can track people, and that’s what I worry about.”

During the conversation, Mr. Meyers and Ms. Swisher swapped stories, delighting in their shared experience coaxing truths from tight-lipped powerhouses.

“I think smart people like to be challenged,” Ms. Swisher said, referring to Mr. Meyer's question about why people agree to her famously frank interviews. “I think they get bored with these kinds of talking interviews and suck-up interviews… I think it gives them a challenge. And so if they’re people of maturity, they like it. If they’re not, they think they can best me… In some ways, I think they have things that they want to say, and they want to think them through, and I think that I help them do that.”

Wrapping up their conversation, Ms. Swisher turned the microphone onto Mr. Meyers, asking him about the Screen Writers Guild (SAG) strike, and who he would like to have on his show when it does return.

Like many of the politicians the two discussed interviewing, Mr. Meyers answered the question with another question: “Would you come on my show?”

The two vowed to have each other as guests on their respective shows. But for now Ms. Swisher’s appearance on Late Night with Seth Meyers will have to wait until a resolution is made in the ongoing strike, the end of which is yet to be determined.

Ms. Swisher said that the standstill is due, in part, to SAG misidentifying its enemy.

“You’re all fighting with the studios,” she said. “Your real enemy is tech, by the way. Because they can sit here and wait you out with all their money, and they’re selling toilet paper and iPhones and whatever the heck they’re selling, and they’re going to then AI you and use TikTok and whatever else. It’s really interesting to watch you in old fight when actually they’re the ones sucking everything down via AI.”

Quick in his rebuttal, Mr. Meyers revealed his plan to salvage his career: “I’ve got a plan B,” he said. “You know what it is? Book Festival.”