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.

By providing your email, you agree to The Information’s Privacy Policy

Recent Editions

The Takeaway

Tech’s Privilege Barrier

By Jessica E. Lessin · Jul 10, 2015 6:58am PDT · 2 comments
Behind the articles we write about hot startups and funding rounds is a truth that needs a headline of its own: The technology industry is not as meritocratic as it may seem. For this column, I am focusing specifically on entrepreneurs, the people who found companies and beat the odds to turn them into something big. By many measures, the... Behind the articles we write about hot startups and funding rounds is a truth that needs a...
The Takeaway

The Who and Why of the YC Venture Fund

By Jessica E. Lessin · Jul 2, 2015 7:13am PDT · 1 comment
I recently heard that Twitter’s former chief operating officer Ali Rowghani is going to play a big role in the new Y Combinator venture fund. I suspect he’s running it, based on the fact that multiple LPs who have been doing diligence about the fund have been asking about him, but that still may be up in the air.  Regardless, we can expect... I recently heard that Twitter’s former chief operating officer Ali Rowghani is going to play a...
The Takeaway

Silicon Valley’s Easiest Money

By Jessica E. Lessin · Jun 26, 2015 7:19am PDT
As Uber looks for investors to buy more preferred stock valued at $50 billion, it has been turning to the usual late-stage funds. But it also enlisted one of its earliest investors, Shervin Pishevar, to shop a side fund, or special purpose vehicle, to bring individual investors into the round, three people have told me. SPVs have become... As Uber looks for investors to buy more preferred stock valued at $50 billion, it has been...
The Myth of the Consumer-Enterprise Hybrid
By Jessica E. Lessin · Jun 19, 2015 7:30am PDT
The Takeaway

The Myth of the Consumer-Enterprise Hybrid

By Jessica E. Lessin · Jun 19, 2015 7:30am PDT
Evernote, Square, Dropbox: all billion-dollar companies whose days as fast-growing tech darlings are over. While they’re taking in tens of millions or more in revenues, none has yet proven it can be profitable over the long-term.  And they’re wobbling. Phil Libin of Evernote told Amir this week that he’s searching for his replacement,... Evernote, Square, Dropbox: all billion-dollar companies whose days as fast-growing tech darlings...
The Takeaway

Why Didn’t the Twitter Board Have a Better Plan?

By Jessica E. Lessin · Jun 12, 2015 7:31am PDT
The piece of news that surprised me most yesterday wasn’t that embattled Twitter CEO Dick Costolo was stepping down. It was that Twitter’s first CEO and long-time groupie Jack Dorsey was stepping in. Costolo and Dorsey would have you think the transition to Dorsey as interim CEO is perfectly natural and part of the plan, a notion that ran... The piece of news that surprised me most yesterday wasn’t that embattled Twitter CEO Dick Costolo...
The Takeaway

Ben Silbermann and the New Math on E-Commerce

By Jessica E. Lessin · Jun 5, 2015 7:01am PDT · 1 comment
Sometimes the best way to determine how a CEO will act is to consider his or her background. A CEO plucked from the media business is likely to talk a lot about content. One raised outside the U.S. is more likely to focus on international users.  It’s a maxim I often turn to when thinking about Pinterest and its noticeably... Sometimes the best way to determine how a CEO will act is to consider his or her background. A...
The Takeaway

Apps Won’t Make the Apple Watch

By Jessica E. Lessin · May 29, 2015 8:04am PDT · 1 comment
This week Apple executive Jeff Williams made an announcement that had Apple fans cheering: technology for better Apple Watch apps is on the way. For those of you who haven’t played with an Apple Watch or read one of the myriad reviews, the third-party apps from thousands of developers like Evernote, Twitter and MLB are crummy. They aren’t very... This week Apple executive Jeff Williams made an announcement that had Apple fans cheering:...
Private Tech Myths Cheat Sheet
By Jessica E. Lessin · May 22, 2015 8:25am PDT · 1 comment
The Takeaway

Private Tech Myths Cheat Sheet

By Jessica E. Lessin · May 22, 2015 8:25am PDT · 1 comment
It’s a supremely interesting—and confusing—time in private tech investing. Companies like Uber are poised to set record-breaking valuations of $50 billion-plus, and there are lots of high-performing private companies right behind them. But caution abounds. Companies are trying to justify valuations based on very fuzzy metrics. I recently heard... It’s a supremely interesting—and confusing—time in private tech investing. Companies like Uber...
The Takeaway

What Tech Investors (Don’t) Know

By Jessica E. Lessin · May 15, 2015 7:13am PDT
Another week, another round of “bubble” prognostications. This wave was triggered by a little deja vu—AOL being absorbed into a big company, again. The over-covered, overplayed deal caused some to call another top. “I’m calling it now: every time aol gets bought it’s the peak of the bubble,” Kara Swisher Tweeted. I’m in a different camp. Despite... Another week, another round of “bubble” prognostications. This wave was triggered by a little...
The Takeaway

How Snapchat is Killing Social Media

By Jessica E. Lessin · May 8, 2015 11:21am PDT · 2 comments
Is it me, or is “social media” starting to feel different? While browsing Twitter, Facebook, Instagram and Snapchat these days, I still surf through plenty of content from my friends and famous people I choose to follow. But I’m also getting hit more and more with posts from people I have no connection with, curated by the services themselves.... Is it me, or is “social media” starting to feel different? While browsing Twitter, Facebook,...
Dave Goldberg. Photo by Bloomberg.
The Takeaway

How Silicon Valley Celebrated Dave Goldberg

By Jessica E. Lessin · May 5, 2015 4:20pm PDT · 1 comment
In recent days there have been lots of wonderful things said about Dave Goldberg, the Silicon Valley entrepreneur, SurveyMonkey CEO, investor and philanthropist who touched a great number of people before his tragic death Friday evening. But it wasn’t until sitting in a private memorial for hundreds of Goldberg’s friends and family at Stanford... In recent days there have been lots of wonderful things said about Dave Goldberg, the Silicon...
The Unbundled Economy
By Jessica E. Lessin · May 1, 2015 7:33am PDT · 2 comments
The Takeaway

The Unbundled Economy

By Jessica E. Lessin · May 1, 2015 7:33am PDT · 2 comments
During a breakfast meeting in New York this week, I couldn’t help admire my dining companion’s shoes—so much so that I tried to buy them on Amazon.com while walking to my next meeting. Sold out. It seemed like a good time to try a personal shopping app, PS Dept, that promises to search the Internet for a variety of fashion items and then deliver... During a breakfast meeting in New York this week, I couldn’t help admire my dining companion’s...
The Takeaway

The Truth About Female Networking

By Jessica E. Lessin · Apr 24, 2015 10:15am PDT · 1 comment
As the inbox of any female founder will prove, all-female networking is alive and well in the tech industry. There’s a “women” version of virtually every conference on the books and by my count, I’m a member of about a dozen groups of females in tech or media that convene regularly. But if women want to start closing the leadership gap that... As the inbox of any female founder will prove, all-female networking is alive and well in the...
The Takeaway

What Technologists Get Right in Criticizing Government

By Jessica E. Lessin · Apr 17, 2015 10:04am PDT
It sounds like a plot line out of HBO’s “Silicon Valley”: Techies, miffed by government interference in their business, proposing entities outside of government influence where they can run their businesses without worrying about laws. The tech industry has a long history of such ideas. Larry Page has sometimes mused about creating... It sounds like a plot line out of HBO’s “Silicon Valley”: Techies, miffed by government...
Data via Datafox. Chart by Peter Schulz.
The Takeaway

IPO Mythbusting

By Jessica E. Lessin · Apr 10, 2015 11:58am PDT · 2 comments
Lately, I’ve had the sense that as we all sit back and assume that companies like Uber, Airbnb and Dropbox are going to wait forever to go public, we’re going to be surprised. I think we are going to see some big names go out this year—Square?—and more go out next year—Uber? Dropbox? I don’t have new facts to report about what the companies are... Lately, I’ve had the sense that as we all sit back and assume that companies like Uber, Airbnb...
Relationship Advice for Facebook and the Media Industry
By Jessica E. Lessin · Mar 27, 2015 9:28am PDT · 2 comments
The Takeaway

Relationship Advice for Facebook and the Media Industry

By Jessica E. Lessin · Mar 27, 2015 9:28am PDT · 2 comments
Dear Facebook and Publishers, You’re having relationship issues, some of which are playing out in the press. Tom wrote this morning about media companies’ perception that Facebook wants to own their audiences. And news reports this week, including one from The Information about Facebook’s video “Anthology” plans, have made it... Dear Facebook and Publishers, You’re having relationship issues, some of which are playing out in...
The Takeaway

Has Personal Live Video Arrived? Not So Fast

By Jessica E. Lessin · Mar 20, 2015 10:34am PDT · 6 comments
Anyone who has been in the tech industry long enough gets used to deja vu. The industry is constantly popping out ideas that have been tried, over and over again—payments, virtual assistants, tablets—before they eventually find their moment. That’s the context I have in my head when thinking about the spate of activity around live personal video... Anyone who has been in the tech industry long enough gets used to deja vu. The industry is...
The Takeaway

What We Can Learn from Israel

By Jessica E. Lessin · Mar 13, 2015 10:31am PDT
Hello from Jerusalem. It’s just a few days before the elections here, and I was fortunate to spend the last week in the country with a group of U.S. entrepreneurs meeting Israeli entrepreneurs, political leaders and The Information subscribers from Jerusalem, Tel Aviv and Ramallah. It’s been an amazing trip. We met President Reuven Rivlin, who... Hello from Jerusalem. It’s just a few days before the elections here, and I was fortunate to...
The Takeaway

The Apple Watch Upgrade Issue

By Jessica E. Lessin · Mar 6, 2015 10:54am PST
After Monday’s expected Apple Watch event, plenty of people will be talking about whether to buy the highly anticipated gadget now or wait for future models. One important consideration often overlooked in such discussions: how quickly shoppers will tire of the one they buy. Imagine the iPhone you used four years ago. Then imagine using it... After Monday’s expected Apple Watch event, plenty of people will be talking about whether to buy...
The Fight Tech Companies Must Win
By Jessica E. Lessin · Feb 27, 2015 10:15am PST · 1 comment
The Takeaway

The Fight Tech Companies Must Win

By Jessica E. Lessin · Feb 27, 2015 10:15am PST · 1 comment
Every week I become more convinced that the next generation of big tech winners and losers will be determined by one question: Can they localize? Of course, modifying a product for different markets has always been very important to big tech companies. But I think it is becoming the key competitive variable for a few reasons. Every week I become more convinced that the next generation of big tech winners and losers will...