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

The IPO View From Morgan Stanley

By Jessica E. Lessin · Nov 16, 2019 7:45am PST
It is getting to be that time when we look back at 2019, which you may recall was supposed to be a banner year for tech IPOs. It’s fallen short of expectations on multiple fronts from the number of deals (well below last year) to how they are performing. We’ll have more to say on that in the coming weeks. A few weeks ago, I sat... It is getting to be that time when we look back at 2019, which you may recall was supposed to be...
The Takeaway

How Tech Investors Missed by a Mile: TAM vs. SAM

By Jessica E. Lessin · Nov 9, 2019 7:44am PST · 4 comments
SoftBank’s Masayoshi Son and JPMorgan’s Jamie Dimon issued mea culpas about WeWork this week, admitting to mistakes and lessons learned. One of them: when backing a business with billions of dollars, it’s important to pay more attention to how it is going to make money. A shocker right? Yet an appreciation for the... SoftBank’s Masayoshi Son and JPMorgan’s Jamie Dimon issued mea culpas about WeWork...
Apple's Zack Van Amburg, Eddy Cue (in red pants) with Jennifer Aniston, Apple CEO Tim Cook, Reese Witherspoon and Apple's Jamie Erlicht at the "The Morning Show" premiere in New York. Photo by AP
The Takeaway

We’ve Reached Peak Content. Now What?

By Jessica E. Lessin · Nov 2, 2019 7:46am PDT
There were dozens of violinists playing across the balcony at Lincoln Center, free-flowing food and booze and scented candles in the bathroom that cost $45 a piece. This week’s star-studded New York premiere of Apple’s “The Morning Show” was a splashy affair, even by Apple standards. It was also a sign of the kind of... There were dozens of violinists playing across the balcony at Lincoln Center, free-flowing food...
Where Were WeWork’s Bankers?
By Jessica E. Lessin · Oct 26, 2019 8:47am PDT · 1 comment
The Takeaway

Where Were WeWork’s Bankers?

By Jessica E. Lessin · Oct 26, 2019 8:47am PDT · 1 comment
This week’s chapter in the drama of WeWork involved a widely-expected bail out plan from SoftBank that was, as many commentators have pointed out, quite remarkable.It was SoftBank at its most head-scratching. With the company running out of cash, WeWork’s largest investor moved up a $1.5 billion investment, loaned the company another... This week’s chapter in the drama of WeWork involved a widely-expected bail out plan from...
The Takeaway

Regulation Talk Hits Silicon Valley

By Jessica E. Lessin · Oct 19, 2019 7:46am PDT
As Mark Zuckerberg was giving his ‘free speech’ speech in Georgetown, I was interviewing his wife and Chan Zuckerberg Initiative co-founder Priscilla Chan and, later, his colleague Fidji Simo, who runs the Facebook part of Facebook. Nice timing, Mark! The speech was an important backdrop for our Summit where regulation ran... As Mark Zuckerberg was giving his ‘free speech’ speech in Georgetown, I was...
The Takeaway

What VCs Can and Can’t Learn From 2016

By Jessica E. Lessin · Oct 12, 2019 7:46am PDT
It was the end of 2015, and the U.S. stock market was in a rough place. A big selloff in China dragged down stocks globally. Falling oil prices and concerns about the solvency of Greece added to investors’ fears. The pain was felt all the way over in Silicon Valley, where startups who needed to fundraise quickly found investors... It was the end of 2015, and the U.S. stock market was in a rough place. A big selloff in China...
The Takeaway

Inside the VC-Banker Crossfire Over Direct Listings

By Jessica E. Lessin · Oct 5, 2019 7:47am PDT · 2 comments
If you bumped into a venture capitalist this week, he or she probably brought up the super-secret confab Benchmark partner Bill Gurley held this week to proselytize the benefits of direct listings. Investors, directors and lawyers gathered at San Francisco’s Palace Hotel, and, despite the presentation screens going out on... If you bumped into a venture capitalist this week, he or she probably brought up the super-secret...
Three Lessons From WeWork
By Jessica E. Lessin · Sep 28, 2019 7:47am PDT · 2 comments
The Takeaway

Three Lessons From WeWork

By Jessica E. Lessin · Sep 28, 2019 7:47am PDT · 2 comments
The very rapid fall of WeWork founder Adam Neumann who, just a week ago, was on top of a company that investors once valued as high as $47 billion has been notable but not surprising to anyone who has been following the story. That’s because WeWork’s rise represented all that is right (and, more importantly) wrong with the... The very rapid fall of WeWork founder Adam Neumann who, just a week ago, was on top of a company...
The Takeaway

Inside SoftBank’s Big CEO-Fest

By Jessica E. Lessin · Sep 21, 2019 9:12am PDT · 1 comment
These days, SoftBank founder Masayoshi Son can’t escape WeWork. He can’t escape the headlines revealing his desire for the company to put the brakes on its troubled IPO. He can’t even escape his own friends doubting the value of his nearly $9 billion investment in the company.So it isn’t a surprise that the topic hung... These days, SoftBank founder Masayoshi Son can’t escape WeWork. He can’t escape the...
The Takeaway

The Lesson From AB5

By Jessica E. Lessin · Sep 14, 2019 7:47am PDT · 1 comment
The big news of the week was the near passage of the California law that would require Uber, Lyft and other companies that rely on contractors to treat them more like full-time employees. Amir’s sources told him the move could add an estimated 20% to Uber’s costs. Some observers hailed the move as the beginning of the end of... The big news of the week was the near passage of the California law that would require Uber, Lyft...
The Takeaway

What to Watch at Apple’s iPhone Launch

By Jessica E. Lessin · Sep 7, 2019 7:46am PDT
Apple is unveiling its latest iPhones next Tuesday in an annual event that generates no shortage of interest from the tech heads. There’s speculation and reporting pointing to upgraded cameras, improved facial recognition, a new dongle that would compete with Tile and more. The pressure is on for these phones to sell well. iPhone... Apple is unveiling its latest iPhones next Tuesday in an annual event that generates no shortage...
The News Disruption We Should All Fear
By Jessica E. Lessin · Aug 31, 2019 7:45am PDT · 2 comments
The Takeaway

The News Disruption We Should All Fear

By Jessica E. Lessin · Aug 31, 2019 7:45am PDT · 2 comments
Every fall, as I prepare for our annual Media Bootcamp—where media leaders pick each other’s brains and trade strategies—I sit back and reflect on the big changes I see coming to the news business in the months ahead. For the past three years, the biggest problem and its solution have been painfully obvious. As internet... Every fall, as I prepare for our annual Media Bootcamp—where media leaders pick each...
The Takeaway

The Problem for SoftBank’s New Vision Fund

By Jessica E. Lessin · Aug 23, 2019 4:58pm PDT
Signs that the global economy is in trouble are mounting, yet here in Silicon Valley startups and venture capital funds are still raising record amounts. I feel the disconnect more than ever and especially when thinking about SoftBank and its Vision Fund. The mega fund, whose second vintage is slated to come in at more than $100 billion, is the... Signs that the global economy is in trouble are mounting, yet here in Silicon Valley startups and...
The Takeaway

Employee Unrest and Political Neutrality at Google and the New York Times

By Jessica E. Lessin · Aug 17, 2019 8:01am PDT · 1 comment
Employee unrest inside big tech companies remains an important story. Wired reminded us of it this week, with this excellent piece about Google. The company is facing unprecedented pressure from employees on both the left and right who are unhappy about its business positions and the way various groups are treated inside the company. The result:... Employee unrest inside big tech companies remains an important story. Wired reminded us of it...
The Takeaway

The Fuzzy Science of IPO Measurement

By Jessica E. Lessin · Aug 10, 2019 7:45am PDT · 1 comment
As the tech IPO bandwagon continues, journalists and investors are keeping score. The only problem is no one seems to have the same definition of success. Was Zoom a successful IPO because its share price shot up 72% on its opening day and now trades 161% above its IPO price? What about the fact that the company sold relatively little... As the tech IPO bandwagon continues, journalists and investors are keeping score. The only...
What the Uber IPO Did and Didn’t Teach Us
By Jessica E. Lessin · Aug 3, 2019 7:46am PDT
The Takeaway

What the Uber IPO Did and Didn’t Teach Us

By Jessica E. Lessin · Aug 3, 2019 7:46am PDT
Back in May—when Uber held one of the most disappointing IPOs in history—I wondered whether the days of investors pouring billions into money-losing private tech companies may be drawing to a close. Yet, not three months later, it appears that not only has that not happened, but things are about to get even crazier. Back in May—when Uber held one of the most disappointing IPOs in history—I wondered...
The Takeaway

Regulation Is Not the Bogeyman

By Jessica E. Lessin · Jul 27, 2019 7:45am PDT
Facebook’s long-awaited Federal Trade Commission settlement, including a $5 billion fine, arrived—with somewhat of a whimper. As reporters and lobbyists used Twitter to debate who got the better deal, Facebook investors shrugged it off. Even word of a sweeping Justice Department tech-sector wide antitrust investigation targeting... Facebook’s long-awaited Federal Trade Commission settlement, including a $5 billion fine,...
The Takeaway

What’s At Stake for Silicon Valley in the Trade Battle With China

By Jessica E. Lessin · Jul 13, 2019 7:47am PDT
This week our Asia team stayed up late to lead a subscriber conference call on the future relationship between Chinese and U.S. tech. Foreign correspondents must join new parents as among the most sleep-deprived sets of humans. (Shout out to those on our team who are both!)It was a great call, and I learned a lot from our team, which includes... This week our Asia team stayed up late to lead a subscriber conference call on the future...
The Takeaway

Watching Tim Cook at Sun Valley

By Jessica E. Lessin · Jul 6, 2019 7:46am PDT
The stakes are high for many CEOs at Sun Valley this year, which begins this Tuesday. Silicon Valley needs to make nice with its enemies, with looming antitrust investigations that could break apart several businesses. The large media conglomerates, which have long agitated for such scrutiny of tech, are themselves still trying to rearrange the... The stakes are high for many CEOs at Sun Valley this year, which begins this Tuesday. Silicon...
My Last Interaction With Jony Ive
By Jessica E. Lessin · Jun 29, 2019 7:46am PDT
The Takeaway

My Last Interaction With Jony Ive

By Jessica E. Lessin · Jun 29, 2019 7:46am PDT
It was my first week on the Apple beat at the Wall Street Journal in 2011 and Steve Jobs had recently passed away. Tim Cook was in charge, and I was waiting for him to make a big move to show how he was going to be different from—or similar to—Jobs.Cook announced a few changes here and there—corporate philanthropy stuff and the... It was my first week on the Apple beat at the Wall Street Journal in 2011 and Steve Jobs had...