Periodically

The Takeaway

By Jessica 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

To Return or Not to Return? That Is the Question

By Jessica Lessin · May 2, 2020 7:46am PDT · 3 comments
This week, it was finally time to confront the question I have been avoiding for weeks: how and when our team at The Information should go back to our offices. I think that day is still likely far away in San Francisco and New York. (Our Hong Kong team just moved into their new digs!) But in the interest of being prepared, I felt that I had... This week, it was finally time to confront the question I have been avoiding for weeks: how and...
The Takeaway

Why the Glass Might Be Half Full for Local News

By Jessica Lessin · Apr 25, 2020 7:47am PDT · 3 comments
Earlier this week, I got a push notification from the San Francisco Chronicle with a map of Covid-19 infections by ZIP code. It was exactly the kind of local news I felt I needed to read—immediately. I looked away from the Zoom meeting I was on, tapped and instantly shared the link with friends.  Covid-19 has devastated local... Earlier this week, I got a push notification from the San Francisco Chronicle with a map of...
TaskRabbit founder Leah Solivan.
The Takeaway

Fundraising in a Crisis: Lessons From TaskRabbit

By Jessica Lessin · Apr 18, 2020 7:45am PDT
It was December 2008, and Leah Busque was broke. It had been six months since she had left her cushy job as an engineer for IBM to build a service helping people outsource their errands to folks looking for extra income. And despite months of conversations with investors—occurring against headwinds of the financial crisis—her credit... It was December 2008, and Leah Busque was broke. It had been six months since she had left her...
Public Companies, Private Companies and Why the Grass Is Always Greener
By Jessica Lessin · Apr 11, 2020 7:46am PDT · 1 comment
The Takeaway

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

By Jessica 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 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 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...
The Takeaway

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

By Jessica 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 (Pink) Elephant in the Tech Press
By Jessica Lessin · Mar 14, 2020 7:47am PDT · 5 comments
Ty Haney. Photo by Getty Images
The Takeaway

The (Pink) Elephant in the Tech Press

By Jessica 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 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 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 Takeaway

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

By Jessica 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...
‘Best of Times’ or ‘Worst of Times’ in Silicon Valley
By Jessica Lessin · Feb 15, 2020 7:46am PST · 4 comments
The Takeaway

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

By Jessica 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 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 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
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
Tech’s Tall Order at Davos
By Jessica Lessin · Jan 18, 2020 7:46am PST
Microsoft CEO Satya Nadella. Photo by Bloomberg
The Takeaway

Tech’s Tall Order at Davos

By Jessica 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 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 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...
The Takeaway

Books to Read in 2020

By Jessica 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
Dystopian Silicon Valley and the Wisdom of Richard Hendricks
By Jessica Lessin · Dec 21, 2019 7:47am PST
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 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...