Periodically

The Takeaway

By Jessica E. Lessin

An inside perspective on tech, media and startups from a reporter and founder who tells the truth about Silicon Valley.

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Recent Editions

The Takeaway

Public Companies, Private Companies and Why the Grass Is Always Greener

By Jessica E. Lessin · Apr 11, 2020 7:46am PDT · 1 comment
Covid-19 has resulted in a dramatic loss of life, plunged the U.S. into recession and created who knows what other disasters that we will be dealing with for years to come. It also interrupted a very prolonged private technology boom and IPO streak that, while wobbling before the pandemic, has now come to a crashing halt. Covid-19 has resulted in a dramatic loss of life, plunged the U.S. into recession and created who...
Atlassian co-CEO Scott Farquhar. Photo by Flickr/Betsy Weber
The Takeaway

A Covid-19 CEO Checklist and Other Lessons From Morgan Stanley’s Virtual Software CEO Summit

By Jessica E. Lessin · Apr 4, 2020 7:47am PDT · 4 comments
For the last several summers, the who’s who of software executives have gathered in Deer Valley for two days of talks about the financial markets and how software is eating the world.Morgan Stanley’s NextGen Software CEO Summit is the kind of exclusive confab where attendees discuss the pros and cons of direct listings by fire pits... For the last several summers, the who’s who of software executives have gathered in Deer...
Instacart CEO Apoorva Mehta with The Information's Jessica Lessin last year. Photo by Angie Silvy
The Takeaway

A ‘Crucible’ Moment: Inside Instacart CEO’s COVID-19 Playbook

By Jessica E. Lessin · Mar 28, 2020 7:45am PDT · 1 comment
As Instacart founder and CEO Apoorva Mehta sat down to write an email to his management team on February 24, it wasn’t about his previous rallying cry for the year: getting closer to profitability ahead of an eventual IPO. Something bigger was looming. The grocery delivery company’s investors and board members, including Jeff... As Instacart founder and CEO Apoorva Mehta sat down to write an email to his management team on...
A Tough Week, What’s Next and a Global COVID-19 Hackathon
By Jessica E. Lessin · Mar 21, 2020 7:45am PDT · 2 comments
The Takeaway

A Tough Week, What’s Next and a Global COVID-19 Hackathon

By Jessica E. Lessin · Mar 21, 2020 7:45am PDT · 2 comments
My what a difference a week makes. Last week, I was writing this column curled up at a desk from home, wondering when things would go back to normal. This week was anything but normal, and we won’t see normal for a long time. Our hearts go out to everyone affected by COVID-19 and the amazing health workers on the front lines. The week... My what a difference a week makes. Last week, I was writing this column curled up at a desk from...
Ty Haney. Photo by Getty Images
The Takeaway

The (Pink) Elephant in the Tech Press

By Jessica E. Lessin · Mar 14, 2020 7:47am PDT · 5 comments
“I bet that she is next.”So read the text message from a friend as she sent me the essay The Wing CEO Audrey Gelman published about the mistakes she’s made as a founder and what she’s learned from them. It offered the kind of admirable candor that CEOs don’t often show. But in today’s climate my friend... “I bet that she is next.”So read the text message from a friend as she sent me the...
The Takeaway

Dorsey, Iger and the Dangerous ‘One Guy’ Myth

By Jessica E. Lessin · Mar 7, 2020 7:46am PST · 2 comments
A few weeks ago, Bob Iger stepped aside as the CEO of Disney and gave the job to one of his long-time deputies Bob Chapek. It was a routine, safe and, in hindsight, obvious move. And yet, I was supremely bummed. For years now, many people in media, myself included, have speculated who Iger would hand the reins of the world’s most... A few weeks ago, Bob Iger stepped aside as the CEO of Disney and gave the job to one of his...
The Takeaway

What Coronavirus Taught Me About the News

By Jessica E. Lessin · Feb 29, 2020 7:45am PST · 6 comments
I spent some time this week preparing for the coronavirus, following the CDC’s recommendations. I stocked up on non-perishable food, washed my hands so much they hurt and canceled an upcoming day trip to LA. (Hello, Zoom!)But there was one thing I wasn’t prepared for: making sense of all the “news. I spent some time this week preparing for the coronavirus, following the CDC’s...
Art by Mike Sullivan
The Information is Launching a Book Club. Here’s Why
By Jessica E. Lessin · Feb 22, 2020 7:45am PST · 1 comment
Art by Mike Sullivan
The Takeaway

The Information is Launching a Book Club. Here’s Why

By Jessica E. Lessin · Feb 22, 2020 7:45am PST · 1 comment
Since I started The Information, I’ve wanted to launch a book club for our subscribers. But we’ve been busy. It had to wait. This week, however, as four fascinating books about tech and the Bay Area piled up on my desk, I knew it was time. Starting this month, The Information will choose a book a month as our official Book Club... Since I started The Information, I’ve wanted to launch a book club for our subscribers. But...
The Takeaway

‘Best of Times’ or ‘Worst of Times’ in Silicon Valley

By Jessica E. Lessin · Feb 15, 2020 7:46am PST · 4 comments
Some of the most interesting times to be a journalist are when there are two opposing views about the same circumstances, and it’s hard to tell who is right. That, to a tee, describes the mood around the business opportunities in Silicon Valley right now. Some of the most interesting times to be a journalist are when there are two opposing views about...
The Takeaway

The New York Times and A Taste of My Own Medicine

By Jessica E. Lessin · Feb 8, 2020 7:45am PST · 1 comment
As a founder, I sometimes sit on the other side of the table and experience what it is like to have an article written about The Information. It's always a little strange. I’m used to being the one asking the questions. But it is also very illuminating and has changed, in small ways, my tactics as a journalist. So when the New... As a founder, I sometimes sit on the other side of the table and experience what it is like to...
Entrepreneurs from The 19th, TrueHoop and the New Consumer
The Takeaway

Some Good News for News

By Jessica E. Lessin · Feb 1, 2020 7:45am PST
This week we hosted our third annual bootcamp for news entrepreneurs in San Francisco, and it has prompted a lot of reflection.Friday morning, we caught up with our full class of founders from previous The Information Accelerator classes. You can read about them all here. This week we hosted our third annual bootcamp for news entrepreneurs in San Francisco, and it has...
Jeff Bezos. Photo by Bloomberg
Jeff Bezos and the Real Cost of the Washington Post
By Nick Wingfield · Jan 25, 2020 7:46am PST
Jeff Bezos. Photo by Bloomberg
The Takeaway

Jeff Bezos and the Real Cost of the Washington Post

By Nick Wingfield · Jan 25, 2020 7:46am PST
This week’s blockbuster revelations about the possible role of Saudi Arabia’s crown prince in the hacking of Jeff Bezos’ phone was a literal eye-popper of a story. It raised so many troubling questions about technology, politics and business. For me though, it was a moment for reflection on a tangential story: how differently... This week’s blockbuster revelations about the possible role of Saudi Arabia’s crown...
Microsoft CEO Satya Nadella. Photo by Bloomberg
The Takeaway

Tech’s Tall Order at Davos

By Jessica E. Lessin · Jan 18, 2020 7:46am PST
Next week, tech CEOs will trade their vests for furry hats and boots and trek to the World Economic Forum in Davos, Switzerland. Years ago, the trek was a sort of celebratory victory lap. With their businesses skyrocketing, executives from Facebook, Google, Microsoft, Uber and Salesforce, to name a few, were rock stars. But amid privacy scandals... Next week, tech CEOs will trade their vests for furry hats and boots and trek to the World...
The Takeaway

‘Masageddon’ and the Limits of the SoftBank Playbook

By Jessica E. Lessin · Jan 11, 2020 7:46am PST · 1 comment
Back in September, when Cory broke the story of the WeWork’s impending layoffs, we wondered: Was this just the beginning? So, this week, when he got a tip that Getaround—the car rental service backed by SoftBank—was planning to cut a quarter of its staff, he whipped up a chart to keep track of the toll. We published that... Back in September, when Cory broke the story of the WeWork’s impending layoffs, we...
Art by Danielle Davis
The Takeaway

What to Watch and Listen to in 2020

By Jessica E. Lessin · Jan 4, 2020 7:45am PST
As any The Information reader knows, it is the golden age of digital television and, increasingly audio. But even when you are cruising through content at 1.5x speed, time is limited and you can’t watch it all. To help, our team compiled a list of shows and podcasts you shouldn’t miss. Some have gotten a lot of publicity. Many... As any The Information reader knows, it is the golden age of digital television and, increasingly...
Books to Read in 2020
By Jessica E. Lessin · Dec 28, 2019 7:46am PST
The Takeaway

Books to Read in 2020

By Jessica E. Lessin · Dec 28, 2019 7:46am PST
At the end of every year, we give our subscribers a peek at the books that most entertained or enlightened our staff over the past 12 months. This year’s list is an eclectic mix of nonfiction titles, including political histories, business books, and memoirs. Two of them—both about the events that helped spark the MeToo... At the end of every year, we give our subscribers a peek at the books that most entertained or...
Thomas Middleditch, who plays the Richard Hendricks character in 'Silicon Valley.' Photo by Bloomberg
The Takeaway

Dystopian Silicon Valley and the Wisdom of Richard Hendricks

By Jessica E. Lessin · Dec 21, 2019 7:47am PST
With less than two weeks left in the decade, publications have started firing off think pieces about the last ten years in technology. And, my, they have been depressing.The New York Times declared the 2010s the decade tech “lost its way.” The Atlantic lamented about all the “promises unfulfilled.” BuzzFeed... With less than two weeks left in the decade, publications have started firing off think pieces...
Away co-founders Steph Korey and Jen Rubio. Photo by Getty
The Takeaway

Is the Media Out to Get Tech Founders?

By Jessica E. Lessin · Dec 14, 2019 7:45am PST · 2 comments
Two weeks ago, at a company all-hands meeting at struggling AR company Magic Leap, head of marketing Daniel Diez had a message for his staff. Don’t pay attention to the critical article due to appear soon in The Information. He called us “clickbait” and said our reporting was “bullshit.” He added that reporter... Two weeks ago, at a company all-hands meeting at struggling AR company Magic Leap, head of...
Photo by Bloomberg.
The Takeaway

Inside Our Apple App Store Ordeal

By Jessica E. Lessin · Dec 7, 2019 7:46am PST
It all started with the price.Peter Schulz, who leads our product and engineering teams, walked into my office and told me that we couldn’t charge what we had planned for our upcoming news app because Apple had “tiers” of pricing app developers must follow. Our planned price of $30 a year didn’t fit into any of those... It all started with the price.Peter Schulz, who leads our product and engineering teams, walked...
Jason Blum. Photo by Erin Beach
Hollywood’s Jason Blum, Unscripted
By Jessica E. Lessin · Nov 23, 2019 7:46am PST
Jason Blum. Photo by Erin Beach
The Takeaway

Hollywood’s Jason Blum, Unscripted

By Jessica E. Lessin · Nov 23, 2019 7:46am PST
In reporting, we all talk about the importance of getting out of our bubbles—which in my case means leaving Silicon Valley to spend time on the ground in New York, Los Angeles, Hong Kong and beyond. The value of doing so was crystal clear this week as I sat across from producer Jason Blum to chitchat about the future of Silicon... In reporting, we all talk about the importance of getting out of our bubbles—which in my...