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Westlake Legal Group > Posts tagged "Silicon Valley (Calif)"

A Hard Lesson in Silicon Valley: Profits Matter

Westlake Legal Group 08valley-facebookJumbo A Hard Lesson in Silicon Valley: Profits Matter Wilson, Fred (1961- ) WeWork Companies Inc Venture Capital Union Square Ventures Start-ups Silicon Valley (Calif) Initial Public Offerings Entrepreneurship Computers and the Internet Bird Rides Inc Benchmark Capital

SAN FRANCISCO — Fred Wilson, a venture capitalist at Union Square Ventures, recently published a blog post titled “The Great Public Market Reckoning.” In it, he argued that the narrative that had driven start-up hype and valuations for the last decade was now falling apart.

His post quickly ricocheted across Silicon Valley. Other venture capitalists, including Bill Gurley of Benchmark and Brad Feld of Foundry Group, soon weighed in with their own warnings about fiscal responsibility.

At some start-ups, entrepreneurs began behaving more cautiously. Travis VanderZanden, chief executive of the scooter start-up Bird, declared at a tech conference in San Francisco last week that his company was now focused on profit and not growth. “The challenge is to try to stay disciplined,” he said.

The moves all point to a new gospel that is starting to spread in start-up land. For the last decade, young tech companies were fueled by a wave of venture capital-funded excess, which encouraged fast growth above all else. But now some investors and start-ups are beginning to rethink that mantra and instead invoke turning a profit and generating “positive unit economics” as their new priorities.

The nascent change is being driven by the stumbles of some high-profile “unicorns” — the start-ups that were valued at $1 billion and above in the private markets — just as they reached the stock market.

The most visible of those was the office rental start-up WeWork, which dramatically ousted its chief executive and withdrew its initial public offering last month. At the same time, shares of Peloton, a fitness start-up, and SmileDirectClub, an online orthodontics company, immediately cratered after the companies went public. And Uber, Lyft and Slack — which also listed their stocks this year — have similarly dealt with falling stock prices for months.

The lackluster performances have raised questions about Silicon Valley’s start-up formula of spending lots of money to grow at the expense of profits. (All of those companies lose money.) Public market investors, it seemed, just weren’t having it.

“A lot of these highly valued companies have run into the buzz saw of Wall Street, where they’re questioning or reminding us that profitability matters,” said Patricia Nakache, a partner at Trinity Ventures, a Silicon Valley venture capital firm.

She added that she anticipated a “ripple effect” on private start-up valuations that would start with the largest, most valuable companies and trickle down to the smaller, younger ones.

For start-ups and investors that were used to heady times and big spending, that means it may be time for a reset.

Aileen Lee, an investor at Cowboy Ventures, a venture capital firm in Palo Alto, Calif., said she considered dusting off a four-year-old “winter is coming” email she had sent to start-ups in 2015, telling them to prepare for a downturn. She hasn’t revived the warning yet, she said, because “I worry about becoming the boy who cried wolf.”

Other venture capitalists are being more forward. At Eniac Ventures, a venture firm in New York and San Francisco, the partners recently combed through their companies and identified the “gross margins” — a measure of profitability — for each one, said Nihal Mehta, general partner of the firm. This was not something the firm regularly looked at, he said, but they were inspired by Mr. Wilson’s cautionary blog post.

They ultimately decided that in future meetings with entrepreneurs, they would push for more detailed financial models, even though the companies are very young, Mr. Mehta said. While Eniac had looked at this when making investments before, “now it’s more important,” he said.

Tech start-ups have long gone through different cycles of fear and loathing. When the 2008 recession began, Sequoia Capital, one of the highest-profile venture firms, called a mass meeting with its start-ups and presented a slide deck, titled “R.I.P. Good Times,” that featured a graphic of a “death spiral” and a skull.

The event was intended as a way to shock the start-ups into reining in costs to survive the downturn. Sequoia’s presentation quickly became the talk of Silicon Valley, which did not fall into as deep an economic funk as other parts of the United States.

Yet other alarms about the state of the start-up economy fell on deaf ears.

In 2015, as unicorn start-ups sucked in billions of dollars in funding and soared to stratospheric valuations, Mr. Gurley of Benchmark bemoaned “the complete absence of fear” in Silicon Valley and said “dead unicorns” would soon appear. In 2016, Jim Breyer, a venture capitalist who was an early Facebook investor, also predicted “blood in the water” for the unicorns.

But the money continued to flood into tech start-ups from overseas investors, private equity firms, corporations and SoftBank’s behemoth Vision Fund. That allowed founders to command higher valuations and delay going public. By the end of 2018, start-ups in the United States had raised a record $131 billion in venture funding, surpassing the amount collected during the late 1990s dot-com boom, according to Pitchbook and the National Venture Capital Association.

Mr. Gurley gave up on his warnings of excess. “You have to adjust to reality and play the game on the field,” he said in an interview last year.

(Complaining about high valuations is a longstanding pastime among venture capitalists, of course, since most prefer to invest their money in cheaply priced start-ups rather than expensive ones.)

This year, the warnings are being revived. In his recent blog post, Mr. Wilson wrote that many of today’s start-ups were focused on traditional physical industries like real estate, exercise or transportation. They should not command the high valuations that pure software companies — which tend to have less overhead — have, he wrote.

In several message exchanges, Mr. Wilson said he had already seen that as criticism of WeWork mounted over the last month, some start-up fundings were taking place at lower valuations and with stricter terms than the companies had hoped for.

“What I would like to see is a bit more rationality, and I’m hopeful we are going to get it,” he said.

By last week, his words appeared to be sinking in elsewhere.

At a start-up conference held by the tech publication TechCrunch at a San Francisco convention center, around 10,000 founders, investors and “innovators” watched interviews with slightly more famous founders, investors and “innovators” from a dark, cavernous room. Onstage, entrepreneurs lamented the unforgiving stock market and challenging investment environment.

Postmates, a food delivery start-up that confidentially filed to go public in February, attended the confab. The company has not yet gone public because the markets have been “choppy when it comes to growth companies,” said Bastian Lehmann, Postmates’ chief executive, at the event.

Bird, the scooter start-up, announced $275 million in fresh funding at the conference. But its chief executive, Mr. VanderZanden, said he had been able to raise that money only because his unprofitable company had taken steps this year to shore up its losses. Many scooter companies have lost their shine this year because of regulatory pushback and safety issues.

The shift toward making a profit wasn’t easy, Mr. VanderZanden said. “I’m an ex-growth guy, and sometimes it’s painful for me,” he said.

But spending fast to grow fast was just no longer feasible, he added. It is now difficult for “a growth-at-all-costs company burning hundreds of millions of dollars with negative unit economics” to get funding, he said. “This is going to be a healthy reset for the tech industry.”

Real Estate, and Personal Injury Lawyers. Contact us at: https://westlakelegal.com 

Silicon Valley’s Mantra of Spend Big, Grow Fast? It’s Changing

Westlake Legal Group 08valley-facebookJumbo Silicon Valley’s Mantra of Spend Big, Grow Fast? It’s Changing Wilson, Fred (1961- ) WeWork Companies Inc Venture Capital Union Square Ventures Start-ups Silicon Valley (Calif) Initial Public Offerings Entrepreneurship Computers and the Internet Bird Rides Inc Benchmark Capital

SAN FRANCISCO — Fred Wilson, a venture capitalist at Union Square Ventures, recently published a blog post titled “The Great Public Market Reckoning.” In it, he argued that the narrative that had driven start-up hype and valuations for the last decade was now falling apart.

His post quickly ricocheted across Silicon Valley. Other venture capitalists, including Bill Gurley of Benchmark and Brad Feld of Foundry Group, soon weighed in with their own warnings about fiscal responsibility.

At some start-ups, entrepreneurs began behaving more cautiously. Travis VanderZanden, chief executive of the scooter start-up Bird, declared at a tech conference in San Francisco last week that his company was now focused on profit and not growth. “The challenge is to try to stay disciplined,” he said.

The moves all point to a new gospel that is starting to spread in start-up land. For the last decade, young tech companies were fueled by a wave of venture capital-funded excess, which encouraged fast growth above all else. But now some investors and start-ups are beginning to rethink that mantra and instead invoke turning a profit and generating “positive unit economics” as their new priorities.

The nascent change is being driven by the stumbles of some high-profile “unicorns” — the start-ups that were valued at $1 billion and above in the private markets — just as they reached the stock market.

The most visible of those was the office rental start-up WeWork, which dramatically ousted its chief executive and withdrew its initial public offering last month. At the same time, shares of Peloton, a fitness start-up, and SmileDirectClub, an online orthodontics company, immediately cratered after the companies went public. And Uber, Lyft and Slack — which also listed their stocks this year — have similarly dealt with falling stock prices for months.

The lackluster performances have raised questions about Silicon Valley’s start-up formula of spending lots of money to grow at the expense of profits. (All of those companies lose money.) Public market investors, it seemed, just weren’t having it.

“A lot of these highly valued companies have run into the buzz saw of Wall Street, where they’re questioning or reminding us that profitability matters,” said Patricia Nakache, a partner at Trinity Ventures, a Silicon Valley venture capital firm.

She added that she anticipated a “ripple effect” on private start-up valuations that would start with the largest, most valuable companies and trickle down to the smaller, younger ones.

For start-ups and investors that were used to heady times and big spending, that means it may be time for a reset.

Aileen Lee, an investor at Cowboy Ventures, a venture capital firm in Palo Alto, Calif., said she considered dusting off a four-year-old “winter is coming” email she had sent to start-ups in 2015, telling them to prepare for a downturn. She hasn’t revived the warning yet, she said, because “I worry about becoming the boy who cried wolf.”

Other venture capitalists are being more forward. At Eniac Ventures, a venture firm in New York and San Francisco, the partners recently combed through their companies and identified the “gross margins” — a measure of profitability — for each one, said Nihal Mehta, general partner of the firm. This was not something the firm regularly looked at, he said, but they were inspired by Mr. Wilson’s cautionary blog post.

They ultimately decided that in future meetings with entrepreneurs, they would push for more detailed financial models, even though the companies are very young, Mr. Mehta said. While Eniac had looked at this when making investments before, “now it’s more important,” he said.

Tech start-ups have long gone through different cycles of fear and loathing. When the 2008 recession began, Sequoia Capital, one of the highest-profile venture firms, called a mass meeting with its start-ups and presented a slide deck titled “R.I.P. Good Times” that featured a graphic of a “death spiral” and a skull.

The event was intended as a way to shock the start-ups into reining in costs to survive the downturn. Sequoia’s presentation quickly became the talk of Silicon Valley, which did not fall into as deep an economic funk as other parts of the United States.

Yet other alarms about the state of the start-up economy fell on deaf ears.

In 2015, as unicorn start-ups sucked in billions of dollars in funding and soared to stratospheric valuations, Mr. Gurley of Benchmark bemoaned “the complete absence of fear” in Silicon Valley and said “dead unicorns” would soon appear. In 2016, Jim Breyer, a venture capitalist who was an early Facebook investor, also predicted “blood in the water” for the unicorns.

But the money continued to flood into tech start-ups from overseas investors, private equity firms, corporations, and SoftBank’s behemoth Vision Fund. That allowed founders to command higher valuations and delay going public. By the end of 2018, start-ups in the United States had raised a record $131 billion in venture funding, surpassing the amount collected during the late 1990s dot-com boom, according to Pitchbook and the National Venture Capital Association.

Mr. Gurley gave up on his warnings of excess. “You have to adjust to reality and play the game on the field,” he said in an interview last year.

(Complaining about high valuations is a longstanding pastime among venture capitalists, of course, since most prefer to invest their money in cheaply priced start-ups rather than expensive ones.)

This year, the warnings are being revived. In his recent blog post, Mr. Wilson wrote that many of today’s start-ups are focused on traditional physical industries like real estate, exercise or transportation. They should not command the high valuations that pure software companies — which tend to have less overhead — have, he wrote.

In several message exchanges, Mr. Wilson said he has already seen that as criticism of WeWork mounted over the last month, some start-up fundings were taking place at lower valuations and with stricter terms than the companies had hoped for.

“What I would like to see is a bit more rationality and I’m hopeful we are going to get it,” he said.

By last week, his words appeared to be sinking in elsewhere.

At a start-up conference held by the tech publication TechCrunch at a San Francisco convention center, around 10,000 founders, investors and “innovators” watched interviews with slightly more famous founders, investors and “innovators” from a dark, cavernous room. Onstage, entrepreneurs lamented the unforgiving stock market and challenging investment environment.

Postmates, a food delivery start-up that confidentially filed to go public in February, attended the confab. The company has not yet gone public because the markets have been “choppy when it comes to growth companies,” said Bastian Lehmann, Postmates’ chief executive, at the event.

Bird, the scooter start-up, announced $275 million in fresh funding at the conference. But its chief executive, Mr. VanderZanden, said he was only able to raise that money because his unprofitable company had taken steps this year to shore up its losses. Many scooter companies have lost their shine this year because of regulatory pushback and safety issues.

The shift toward making a profit wasn’t easy, Mr. VanderZanden said. “I’m an ex-growth guy and sometimes it’s painful for me,” he said.

But spending fast to grow fast was just no longer feasible, he added. It is now difficult for “a growth at-all-costs company burning hundreds of millions of dollars with negative unit economics” to get funding, he said. “This is going to be a healthy reset for the tech industry.”

Real Estate, and Personal Injury Lawyers. Contact us at: https://westlakelegal.com 

Silicon Valley’s Mantra of Spend Big, Grow Fast? It’s Changing

Westlake Legal Group 08valley-facebookJumbo Silicon Valley’s Mantra of Spend Big, Grow Fast? It’s Changing Wilson, Fred (1961- ) WeWork Companies Inc Venture Capital Union Square Ventures Start-ups Silicon Valley (Calif) Initial Public Offerings Entrepreneurship Computers and the Internet Bird Rides Inc Benchmark Capital

SAN FRANCISCO — Fred Wilson, a venture capitalist at Union Square Ventures, recently published a blog post titled “The Great Public Market Reckoning.” In it, he argued that the narrative that had driven start-up hype and valuations for the last decade was now falling apart.

His post quickly ricocheted across Silicon Valley. Other venture capitalists, including Bill Gurley of Benchmark and Brad Feld of Foundry Group, soon weighed in with their own warnings about fiscal responsibility.

At some start-ups, entrepreneurs began behaving more cautiously. Travis VanderZanden, chief executive of the scooter start-up Bird, declared at a tech conference in San Francisco last week that his company was now focused on profit and not growth. “The challenge is to try to stay disciplined,” he said.

The moves all point to a new gospel that is starting to spread in start-up land. For the last decade, young tech companies were fueled by a wave of venture capital-funded excess, which encouraged fast growth above all else. But now some investors and start-ups are beginning to rethink that mantra and instead invoke turning a profit and generating “positive unit economics” as their new priorities.

The nascent change is being driven by the stumbles of some high-profile “unicorns” — the start-ups that were valued at $1 billion and above in the private markets — just as they reached the stock market.

The most visible of those was the office rental start-up WeWork, which dramatically ousted its chief executive and withdrew its initial public offering last month. At the same time, shares of Peloton, a fitness start-up, and SmileDirectClub, an online orthodontics company, immediately cratered after the companies went public. And Uber, Lyft and Slack — which also listed their stocks this year — have similarly dealt with falling stock prices for months.

The lackluster performances have raised questions about Silicon Valley’s start-up formula of spending lots of money to grow at the expense of profits. (All of those companies lose money.) Public market investors, it seemed, just weren’t having it.

“A lot of these highly valued companies have run into the buzz saw of Wall Street, where they’re questioning or reminding us that profitability matters,” said Patricia Nakache, a partner at Trinity Ventures, a Silicon Valley venture capital firm.

She added that she anticipated a “ripple effect” on private start-up valuations that would start with the largest, most valuable companies and trickle down to the smaller, younger ones.

For start-ups and investors that were used to heady times and big spending, that means it may be time for a reset.

Aileen Lee, an investor at Cowboy Ventures, a venture capital firm in Palo Alto, Calif., said she considered dusting off a four-year-old “winter is coming” email she had sent to start-ups in 2015, telling them to prepare for a downturn. She hasn’t revived the warning yet, she said, because “I worry about becoming the boy who cried wolf.”

Other venture capitalists are being more forward. At Eniac Ventures, a venture firm in New York and San Francisco, the partners recently combed through their companies and identified the “gross margins” — a measure of profitability — for each one, said Nihal Mehta, general partner of the firm. This was not something the firm regularly looked at, he said, but they were inspired by Mr. Wilson’s cautionary blog post.

They ultimately decided that in future meetings with entrepreneurs, they would push for more detailed financial models, even though the companies are very young, Mr. Mehta said. While Eniac had looked at this when making investments before, “now it’s more important,” he said.

Tech start-ups have long gone through different cycles of fear and loathing. When the 2008 recession began, Sequoia Capital, one of the highest-profile venture firms, called a mass meeting with its start-ups and presented a slide deck titled “R.I.P. Good Times” that featured a graphic of a “death spiral” and a skull.

The event was intended as a way to shock the start-ups into reining in costs to survive the downturn. Sequoia’s presentation quickly became the talk of Silicon Valley, which did not fall into as deep an economic funk as other parts of the United States.

Yet other alarms about the state of the start-up economy fell on deaf ears.

In 2015, as unicorn start-ups sucked in billions of dollars in funding and soared to stratospheric valuations, Mr. Gurley of Benchmark bemoaned “the complete absence of fear” in Silicon Valley and said “dead unicorns” would soon appear. In 2016, Jim Breyer, a venture capitalist who was an early Facebook investor, also predicted “blood in the water” for the unicorns.

But the money continued to flood into tech start-ups from overseas investors, private equity firms, corporations, and SoftBank’s behemoth Vision Fund. That allowed founders to command higher valuations and delay going public. By the end of 2018, start-ups in the United States had raised a record $131 billion in venture funding, surpassing the amount collected during the late 1990s dot-com boom, according to Pitchbook and the National Venture Capital Association.

Mr. Gurley gave up on his warnings of excess. “You have to adjust to reality and play the game on the field,” he said in an interview last year.

(Complaining about high valuations is a longstanding pastime among venture capitalists, of course, since most prefer to invest their money in cheaply priced start-ups rather than expensive ones.)

This year, the warnings are being revived. In his recent blog post, Mr. Wilson wrote that many of today’s start-ups are focused on traditional physical industries like real estate, exercise or transportation. They should not command the high valuations that pure software companies — which tend to have less overhead — have, he wrote.

In several message exchanges, Mr. Wilson said he has already seen that as criticism of WeWork mounted over the last month, some start-up fundings were taking place at lower valuations and with stricter terms than the companies had hoped for.

“What I would like to see is a bit more rationality and I’m hopeful we are going to get it,” he said.

By last week, his words appeared to be sinking in elsewhere.

At a start-up conference held by the tech publication TechCrunch at a San Francisco convention center, around 10,000 founders, investors and “innovators” watched interviews with slightly more famous founders, investors and “innovators” from a dark, cavernous room. Onstage, entrepreneurs lamented the unforgiving stock market and challenging investment environment.

Postmates, a food delivery start-up that confidentially filed to go public in February, attended the confab. The company has not yet gone public because the markets have been “choppy when it comes to growth companies,” said Bastian Lehmann, Postmates’ chief executive, at the event.

Bird, the scooter start-up, announced $275 million in fresh funding at the conference. But its chief executive, Mr. VanderZanden, said he was only able to raise that money because his unprofitable company had taken steps this year to shore up its losses. Many scooter companies have lost their shine this year because of regulatory pushback and safety issues.

The shift toward making a profit wasn’t easy, Mr. VanderZanden said. “I’m an ex-growth guy and sometimes it’s painful for me,” he said.

But spending fast to grow fast was just no longer feasible, he added. It is now difficult for “a growth at-all-costs company burning hundreds of millions of dollars with negative unit economics” to get funding, he said. “This is going to be a healthy reset for the tech industry.”

Real Estate, and Personal Injury Lawyers. Contact us at: https://westlakelegal.com 

Silicon Valley Goes to Therapy

Westlake Legal Group 20Therapy-illo-facebookJumbo Silicon Valley Goes to Therapy Venture Capital Therapy and Rehabilitation Start-ups Silicon Valley (Calif) Mental Health and Disorders Anxiety and Stress

SAN FRANCISCO — Silicon Valley told itself a good story, the best one, really: It was saving the world. For nearly a decade, this gave the modern tech worker purpose, optimism and self-confidence.

Then came the bad headlines, followed by worse headlines — about the industry, about the country, about the world. In search of reassurance, tech workers commandeered the old hippie retreat Esalen, co-opted Burning Man, got interested in psychedelics and meditation. It wasn’t enough.

Now, across Silicon Valley, anxious tech workers are finally admitting they have a problem. And they are going to therapy.

“The questions that are percolating in the national consciousness are making tech work not as glamorous or as noble as it was,” said Meredith Whittaker, a Google researcher who resigned in June, in part to protest the company’s military contracts and its ethics around artificial intelligence. “There’s a lot of anxiety. How could you not have that? Tech companies are fueling some of the most egregious human-rights abuses.”

Silicon Valley is approaching its anxiety the way it knows best. So now there is on-demand therapy. Therapy metrics. Therapy R.O.I. Matching therapists with clients using the tools of online dating.

Even therapy start-ups offering the familiar elements of care — talking with a licensed person in an office, surrounded by succulents — emphasize streamlined paperwork, a data-driven approach and happiness analysis. The cure for tech’s ills, they hope, is more tech.

“The best therapists get you better 10x faster than average ones,” promises one such start-up, Kip. “We took world-class providers, supercharged them (and you) with our smart software tools, and designed a seamless experience for both clients and providers.” Another recent venture, Reflect, calls therapy “the gym for your soul.”

The language the companies use is aggressive for something quiet and personal like therapy. But in the Bay Area, founders see little virtue in applying a measured response to a market opportunity.

“What we’re out to build is a new mental health system,” said Alex Katz, the founder of Two Chairs, a therapy start-up that has six clinics in the Bay Area. The company raised $21 million in August.

Traditional therapists scribble notes and review them later, possibly with a mug of chamomile. In the Kip system, notes quickly turn into data. Weeks of therapy are broken down with quizzes to determine exactly how happiness and anxiety levels are progressing, and how quickly.

Kip offers an app that encourages clients to record their moods in real time, prompted by questions that a therapist can choose to have pop up throughout the day. “That way they’re not subject to recency bias,” said Ti Zhao, the company’s founder.

The new data could provide insights that typical therapists would not come up with on their own. But there are risks. Elizabeth Kaziunas, a postdoctoral researcher at New York University, studies mental health tech and privacy. She noted that these apps gathered and organized data that you might not want gathered.

“There’s no guarantee or legal protections built in,” Ms. Kaziunas told me. “This mental health data could be bought or sold.”

For example, an anxiety diagnosis could raise my life insurance rates, she said, adding something new for me to be anxious about. “It’s kind of scary, isn’t it?” she said. “Like when you think about it?”

Recently, I downloaded Stoic, a new mental health tracker app. It promised that after a few days of logging my moods, I would get “charts and insights.” I did a fear-setting exercise, based on a TED Talk by the life-hacking guru Tim Ferriss. The app asked me to pick a fear (the oceans rise and create an uninhabitable world for my unborn children), then imagine the worst that can happen (we all die) and decide what I can do to prevent it (nothing) and repair it (again, guys, I’m dead). I closed the app.

Those funding the therapy start-ups see an entire cohort of tech employees who long ago fused their sense of self-worth to their work, and who are emotionally adrift now that the industry is under assault.

“It’s one thing to be grinding for a big tech company that you believe in, but once you start questioning that company’s motivations, that can make the eight hours a day that you work not feel as fulfilling,” said Michael Seibel, the chief executive of Y Combinator, the start-up investment fund and adviser.

Others feel anxiety or even despair about the environment, democracy, or just the everyday crucibles of work and status-mongering.

“In Silicon Valley,” Mr. Seibel added, “we did not talk this much about mental health even three years ago.” He estimates that more than 50 related start-ups are coming onto the scene. His firm just funded three: Stoic; Quirk, an app that uses cognitive behavioral therapy to treat people with anxiety and depression; and Mindset Health, which creates hypnotherapy apps that it says can treat anxiety, depression and irritable bowel syndrome.

Mindset Health was founded by two brothers, Alex and Chris Naoumidis, who previously created a peer-to-peer dress-sharing app for women. When that app failed, the brothers felt overcome with anxiety.

“We fell into this period of mental health problems,” said Alex Naoumidis, 24.

The brothers tried some of the existing wellness apps — meditation products, mindfulness tools — but remained unmoored. Their father suggested in-person hypnotherapy. It gave them the idea for Mindset.

I downloaded their app ($64 for an annual membership), clicked into the Calm Down section and started a session called Change as a Process. As a first step, the app suggested that I text a friend or tweet to the public the quote “He who conquers himself is the mightiest warrior.” For the next 19 minutes, a soft male voice told me that my mind can slow down. It can convert concerns to decisions. The process can even become second nature. And if it does, I can be a person of action. A person of action.

I did another module, Increase Productivity, which is voiced by a peppy younger man — a start-up bro right in my ear asking me to repeat after him: “I give myself permission to know what I want to be and what I want to do and do it efficiently.”

Somewhat more motivated, I contacted a bunch of the San Francisco area’s traditional therapists and life coaches to ask if anything was changing among their clients. Several told me that a couple of years ago, clients were coming in mostly because of personal issues, but that now they were reporting anxiety about global trends, like climate change and the rise of dictatorships.

In response, some old-line therapists are shifting toward the new market.

“I have seen an increase of people in tech feeling more hopeless. They often say, ‘I don’t know if my job is helping anybody,’” said Krista Regedanz, a psychologist in Palo Alto. “People who want to change the world and have good energy around it — I’m seeing a lot of them come in saying: ‘I don’t know. Does it matter?’”

Last year, May Bartlett, a life coach, started Global Impact Coaching to answer questions about how one’s work might be helping or hurting the world.

“They come in and say, ‘I feel like I’m floating in this vast universe, alone, with no purpose,’” Ms. Bartlett said. “And there’s a lot of this existential dread.”

She designed the program for clients who feel overwhelmed by the news. They wake up to push alerts about obscene actions at the border followed by alerts about species that are dying off, then alerts about people being denied the vote. They are unsure whether they need to quit their jobs.

“One of the most detrimental things is knowing all this information and not knowing what to do about it and feeling helpless,” Ms. Bartlett said. “It’s hard to feel good every day when things seem to be getting worse.”

The fire hose of information about the world is constantly demanding empathy. Ms. Bartlett said she often had her clients think about themselves and their work or mistakes in “the vastness of history.”

“Yes, stuff is hitting the fan right now, and the world is terrible, but if you look at it through 13 billion years, you see: O.K., this is a tiny blip,” she said. “There have been other times of chaos and destruction.”

The tipping point for my own bleak terror began when — I know it’s dumb but — Bitcoin fell. That was the last great fun we all had, and it turned out to be a bust almost beyond measure. The days of goofiness were done, I felt. The news alerts were getting to be a lot. I had, as they say, feelings of powerlessness.

And I had no idea, really, how to find a therapist. The last one I saw I had discovered by searching on Yelp: “best therapist + gay + five stars.” So who am I to judge efforts at smarter matching than that? When I started to notice the raft of therapy start-ups, it struck me as a reasonably healthy trend.

As Allie Stark, a wellness coach in the region, said: “There’s a beauty in existentialism. It’s also very paralyzing.”

Tech workers are starting to be more open about mental health in their own industry. Justin Kan, the chief executive of Atrium, a law-tech company, has been vocal over the last year about his personal struggles and the pleasures of therapy. He found he felt better when he stopped getting so much new information.

“Something that helped me was I deleted all the news off my phone,” Mr. Kan said. “I don’t have the stock market app or Twitter anymore. And that did improve my mood.”

This being San Francisco, there is a longstanding local group for existentialism. The Existential-Humanistic Institute, founded in 1997, is a collective of therapists and philosophers who have been puttering along in mostly quiet private practice for years, working with clients who are struggling not only with relatively ordinary issues but with their very purpose on earth. Interest in their approach appeared to spike along with the rise of Donald J. Trump.

In June, their movement published a textbook: “The Wiley World Handbook of Existential Therapy,” with esoteric chapters on theory but also more practical sections on how to find meaning. “It’s a big revival,” said the organization’s leader, Kirk Schneider.

Dr. Schneider, 63, cited technology itself as one reason for ambient emotional chaos. But he said clients were also suffering from broader social forces — a fear that inequality will lead to violent uprisings, a panic over global authoritarianism, a sense that they are not contributing to the common good.

“The goal is to move from a sense of abject terror and paralysis,” Dr. Schneider said, “to a gradual sense of intrigue and eventual wonder.”

New clients want help unplugging. Amy Eliza Wong, an executive and life coach in San Francisco who sees a steady stream of tech workers, said most of them came to her wanting to tune out despair-inducing headlines and to get back to the business of crushing it.

“There’s a feeling of ‘Let me just turn it off,’” Ms. Wong said. “‘I don’t need this white noise. It’s not helping.’”

This is not to say, of course, that the entire region is mentally imploding. San Franciscans still go to work and read the news. The big tech companies are still attracting eager job applicants. Google is not disbanding because everyone has gone to learn the cello.

There is even a countermovement pushing back on too much self-reflection and news-driven self-flagellation. Its leaders argue that the old optimism worked just fine and that Silicon Valley must march forward.

Followers can be found rallying tightly behind the militant sunniness of venture capitalist Twitter. There, the old fathers of the industry send out a constant stream of start-up bromides. This is the tech positivity movement.

“Optimism, ambition, and recruiting. Will this recipe work for your start-up too?” Paul Graham, a co-founder of Y Combinator, wrote on Twitter last month, in a typical missive. “Yes.”

“Founder-mentality means not caring who gets the credit,” Naval Ravikant, a co-founder of AngelList, tweeted this month. The koan has basically nothing to do with my life, but I found myself nodding.

Still, I was curious what start-up therapy really looked like, and I signed up for a session with Kip. The app prompted me to take something called a DASS-21 before my session. The first question: How often have I found it hard to wind down this week? (“A considerable degree.”)

When I got to the office of Anja Schmitz, one of the Kip therapists, it was completely normal. There was a sofa, a chair and a sandy Zen garden with rakes.

We talked.

Afterward, before I was even out of the building, I got an in-app assignment — a self-assessment to do during a period of anxiety.

I headed to catch the train home. The station had been taken over by a promotional campaign for Twitter. Giant ads with blown-up tweets wrapped around every column, covered the walls, blanketed the floors. “Twitter is a mosaic of madness,” read one of the messages under my feet. Another: “Twitter is garbage and I am a raccoon.”

The crowd was the usual — extremely technical-looking laptop backpacks, a lost young man with a plastic bag leaking beer that a tunnel gust sprayed into my mouth, which had been agape. Almost everyone was staring at the walls. I tapped into the Kip app.

“Was the trigger internal (like a thought) or external (something happening around you) or both?”

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The World’s First Ambassador to the Tech Industry

COPENHAGEN — Casper Klynge, a career diplomat from Denmark, has worked in some of the world’s most turbulent places. He once spent 18 months embroiled in reconstruction efforts in Afghanistan. For two years, he led a crisis management mission in Kosovo.

Yet Mr. Klynge, 46, says his toughest foreign posting may be the one he has now: as the world’s first foreign ambassador to the technology industry.

In 2017, Denmark became the first nation to formally create a diplomatic post to represent its interests before companies such as Facebook and Google. After Denmark determined that tech behemoths now have as much power as many governments — if not more — Mr. Klynge was sent to Silicon Valley.

“What has the biggest impact on daily society? A country in southern Europe, or in Southeast Asia, or Latin America, or would it be the big technology platforms?” Mr. Klynge said in an interview last month at a cafe in central Copenhagen during an annual meeting of Denmark’s diplomatic corps. “Our values, our institutions, democracy, human rights, in my view, are being challenged right now because of the emergence of new technologies.”

He added, “These companies have moved from being companies with commercial interests to actually becoming de facto foreign policy actors.”

But after two years in the job, Mr. Klynge is under no illusions of where Denmark’s concerns figure in the minds of Silicon Valley executives. Denmark’s population of 5.8 million is smaller than that of the San Francisco Bay Area. Fewer than 0.3 percent of Facebook’s 2.4 billion global users live in the Scandinavian country.

Silicon Valley companies and their leaders have given Mr. Klynge a mixed reception. He has never met with Mark Zuckerberg of Facebook or Sundar Pichai of Google or Timothy D. Cook of Apple. Danish officials said it was like dealing with an opaque new world superpower.

“We’ve been too naïve for too long about the tech revolution,” said Jeppe Kofod, Denmark’s minister for foreign affairs.

So Mr. Klynge’s position is part of an effort “to make sure that democratic governments set the boundaries for the tech industry and not the other way around,” Mr. Kofod said.

Denmark is emblematic of the many small countries that are grappling with technology’s effects on their societies and are frustrated by an inability to meet with, let alone influence, the companies causing that disruption.

Danish officials have been particularly concerned by how technological change is causing challenges that have afflicted other Western democracies: the spread of false and politically divisive content on social media, questions about privacy and data-hungry services, cybersecurity and the low taxes the companies pay outside the United States.

Andrew Cooper, a political-science professor at the University of Waterloo who studies diplomacy, said smaller countries had long needed novel ways to get attention from nations with more power.

ImageWestlake Legal Group merlin_30940718_80798471-96da-41ac-8eb8-3892a9d6cf53-articleLarge The World’s First Ambassador to the Tech Industry Social Media Silicon Valley (Calif) Rumors and Misinformation Politics and Government Facebook Inc Cyberwarfare and Defense Corporations Corporate Taxes COPENHAGEN, Denmark Computers and the Internet Casper Klynge

Ibrahim Didi, the Maldives minister of fisheries and agriculture, right, at an underwater cabinet meeting to highlight the threat of global warming. CreditMohammed Seeneen/Associated Press

The Maldives, for instance, has hosted underwater cabinet meetings to raise awareness about climate change, while Sweden created an embassy in the virtual-world video game Second Life. What’s surprising, Mr. Cooper said, is the extent to which Denmark is applying the strategy to private companies.

“Denmark has to play a different game,” he said.

But the obstacles Mr. Klynge has faced in Silicon Valley have been humbling. He said it had taken nine months to sit down with a senior executive at one of the biggest tech companies, which he declined to name. He arrived expecting a frank conversation on issues agreed on beforehand, including taxes, cybersecurity and internet misinformation — only to be offered a headquarters tour, he said.

When the executive arrived later, he began a brief rant against European regulations of the tech industry, before saying he did not have time for the meeting, Mr. Klynge said. Then the executive left.

As Mr. Klynge was exiting the building, the executive called his mobile phone to ask him to wait. Mr. Klynge thought there had been a change of heart.

Not so.

“When I got back to the conference room he gave me a goody bag with a T-shirt and cap of the particular company,” he said. He said Danish officials “laughed about this incident a lot afterward, but it says a lot about the mind-set of some of the companies in Silicon Valley.”

Some tech companies said they were beginning to better understand Mr. Klynge’s job.

Brad Smith, president of Microsoft, said he spoke regularly with Mr. Klynge, whose appointment he said gave Denmark “outsized influence.”

“If I want to compare notes on technology issues, he’s one of the best-informed people possible,” Mr. Smith said.

Peter Münster, a spokesman for Facebook, said, “It did take a few meetings before we understood the scope and intentions embedded in Klynge’s role.” Now, he added, “we have a good and constructive dialogue with the Danish tech ambassador, who speaks frankly, expressing both criticism and positive feedback.”

Google and Apple declined to comment, while Amazon did not respond to requests for comment.

Mr. Klynge said Denmark should not be overlooked. As a European Union member, it can influence regulations on privacy, competition, content moderation, taxes and misinformation. (He said he often had to clarify to tech executives that he worked separately from one of Denmark’s better-known officials, Margrethe Vestager, the European Union’s top antitrust enforcer, who has levied billions of dollars in fines against the tech industry.)

Mr. Klynge said Denmark should not be overlooked. As a member of the European Union, the country can influence regulations. CreditLaerke Posselt for The New York Times

Denmark has faced some criticism for putting corporations on the same level as sovereign governments, but other countries are also dedicating diplomatic resources to the tech industry. France created an ambassador for digital affairs, and Australia, Britain and Germany, among others, have added tech-centric postings, often to help facilitate trade and investment. But Denmark said it was still the only country with a dedicated tech ambassador posted overseas.

Priya Guha, Britain’s former consul general in San Francisco, said that even as societal challenges grew as a result of giant tech platforms, economic ties were a top priority for diplomats sent to be liaisons with the industry.

“Diplomacy has shifted. We aren’t in the 1900s anymore; we’re not in a world where it’s all about bilateral relationship with other countries,” said Ms. Guha, now a partner at Merian Ventures, a venture capital firm. “Countries need to adapt their view of diplomacy to counter that. The companies will have significant influence on the world, and you can either step back and watch that happen or you can work with that.”

About 55 people in Denmark applied for Mr. Klynge’s job when it was created. He now has a team of about 11, with seven in California, three in Denmark and one in China. His office is in Palo Alto, Calif., not far from the headquarters of many tech companies.

Mr. Klynge maintains some Danish traditions, like cycling to work every morning. But other aspects of living in California remain a shock.

“Despite probably being one of the places with the highest density of millionaires, every single day I meet homeless people on the streets,” he said. He added that there was no way he could afford to live in Silicon Valley, where fixer-uppers regularly cost more than $1 million, if housing was not provided by the Danish government.

Mr. Klynge said he had approached the tech companies as if they were countries, building relationships and networks. In lieu of often frustrating attempts to meet with senior officials, he spends time with lower-ranking workers, former employees, people from smaller competing companies, civil society groups and government officials.

His team sends intelligence cables to government leaders on what is going on within the companies, as well as reports on issues like cybersecurity, the growing use of health data and autonomous vehicles. Danish officials can then use those to inform policymaking.

Mr. Klynge said he traveled to other tech hubs about half the year, visiting China, India and countries in Europe. He said he was surprised that Chinese companies were more open to discussing political issues than those in the United States.

He counts some successes. Last year, when a Danish citizen was killed by an Islamic terrorist while traveling in Morocco, Mr. Klynge quickly spoke with representatives from Facebook and Google to get them to remove the video of the grisly attack.

“Diplomacy is by nature a long-term business where you don’t necessarily see goals being fulfilled from one day to the next,” he said.

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Former Star Google and Uber Engineer Charged With Theft of Trade Secrets

SAN JOSE, Calif. — Anthony Levandowski, one of Silicon Valley’s foremost technologists on self-driving cars, was charged by federal prosecutors on Tuesday with 33 counts of theft and attempted theft of trade secrets from Google.

The criminal charges from the United States Attorney’s Office of the Northern District of California open a new chapter in a legal battle that has embroiled Google, its self-driving car spinoff Waymo and rival Uber in the high-stakes contest over autonomous vehicles. The case also highlights Silicon Valley’s no-holds-barred culture, where gaining an edge in new technologies versus competitors can be paramount.

It is not uncommon for tech companies, which fiercely guard their intellectual property, to sue former employees or the firms they join after they leave. But criminal charges against a senior executive for theft is unusual.

According to the complaint, Mr. Levandowski, who worked on self-driving cars at Google, downloaded more than 14,000 files containing critical information about Google’s autonomous-vehicle research before leaving the company in 2016. He then made an unauthorized transfer of the files to his personal laptop, the complaint said. Mr. Levandowski joined Uber later that year when the ride-hailing firm bought his new self-driving trucking start-up, which was called Otto.

Some of the files that Mr. Levandowski took from Google included private schematics for proprietary circuit boards and designs for light sensor technology, known as Lidar, which are used in self-driving cars, according to the complaint.

“The Bay Area has the best and brightest engineers, and they take big risks,” said John Bennett, the F.B.I. special agent in charge of the San Francisco Division, at a news conference on Tuesday. “But Silicon Valley is not the wild West. The fast-paced and competitive environment does not mean federal laws do not apply.”

The U.S. attorney’s office said Mr. Levandowski, 39, turned himself in at the federal courthouse in San Jose this morning. If convicted, Mr. Levandowski could face a maximum of 10 years in prison, a $250,000 fine for every count and additional restitution.

“All of us are free to move from job to job,” said David L. Anderson, United States attorney in the Northern District of California. “What we cannot do is stuff our pockets on the way out the door.”

Mr. Levandowski’s lawyers, Miles Erlich and Ismail Ramsey, said in a statement that he didn’t steal anything from anyone.

“This case rehashes claims already discredited in a civil case that settled more than a year and a half ago,” they said. “The downloads at issue occurred while Anthony was still working at Google — when he and his team were authorized to use the information. None of these supposedly secret files ever went to Uber or to any other company.”

ImageWestlake Legal Group merlin_133533068_13c3d0f3-142e-47d1-a50b-d5a9c7fa63e9-articleLarge Former Star Google and Uber Engineer Charged With Theft of Trade Secrets Waymo Uber Technologies Inc Suits and Litigation (Civil) Start-ups Silicon Valley (Calif) Page, Larry Levandowski, Anthony Kalanick, Travis Google Inc Driverless and Semiautonomous Vehicles Computers and the Internet Car Services and Livery Cabs Automobiles Alphabet Inc

Former Uber chief executive Travis Kalanick leaving federal court in San Francisco last year during the trial over trade secrets with Waymo.CreditJeff Chiu/Associated Press

Uber said in a statement that the company “has cooperated with the government throughout their investigation and will continue to do so.”

Suzanne Philion, a spokeswoman for Waymo, said the company has “always believed competition should be fueled by innovation, and we appreciate the work of the U.S. Attorney’s Office and the F.B.I. on this case.”

The charges follow a settlement between Waymo and Uber in a trade secrets case. In February 2017, Waymo had accused the ride-hailing firm, Mr. Levandowski and others of stealing self-driving car technology. That case went to trial in San Francisco in February 2018, riveting the tech industry with testimony about the inner workings of technology companies, rivalries among billionaire tech entrepreneurs and the cutthroat competition for engineering talent.

Four days into the trial, Uber and Waymo settled, with Uber agreeing to provide 0.34 percent of its stock to Alphabet, the parent company of Waymo and Google. But Mr. Levandowski’s situation was not resolved by the settlement. The federal judge in the case referred it to the United States Attorney’s Office for a possible criminal inquiry into Mr. Levandowski’s behavior.

Mr. Levandowski was a pioneer in autonomous-vehicle research. He became known for the technology as a graduate student at the University of California, Berkeley, in 2004, when he designed a self-driving motorcycle that was entered in the Pentagon’s first contest for autonomous vehicles.

At Google, which Mr. Levandowski joined last decade, he was a confidant of Larry Page, one of the company’s co-founders. Mr. Levandowski ended up leading many aspects of the self-driving program inside the company’s clandestine “Google X” division. Google’s self-driving car unit was later spun off into Waymo.

In 2016, Mr. Levandowski left Google to form Otto, a self-driving trucking start-up. He took a small army of Google engineers along with him. Otto was quickly acquired by Uber for nearly $700 million. The deal was driven by Travis Kalanick, Uber’s chief executive at the time, who had a vision of building a fleet of self-driving robotaxis that would replace Uber’s hundreds of thousands of human drivers.

In 2017, Waymo sued Uber, Mr. Levandowski and Otto for theft of trade secrets.

“Otto and Uber have taken Waymo’s intellectual property so that they could avoid incurring the risk, time and expense of independently developing their own technology,” Waymo said in its suit.

The relationship between Uber and Mr. Levandowski quickly went south. After invoking his Fifth Amendment right to avoid self-incrimination in the Waymo case, Mr. Levandowski was terminated by Uber in May 2017.

“Uber regrets ever bringing Anthony Levandowski on board,” one of Uber’s lawyers said during the trial last year. “All Uber has to show for Anthony Levandowski is this lawsuit.”

Mr. Levandowski, who made millions of dollars from his work and through sales of his start-ups, has not stepped back. In December, he gave an interview to The Guardian about his new self-driving start-up, Pronto.AI, in which he claimed that he built a car that had driven from San Francisco to New York without human intervention.

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Netflix Falls Short in Big Screen Debut of ‘The Irishman’

Westlake Legal Group merlin_158614983_9e149c3b-1095-4cf8-bdee-844c0bf4af7e-facebookJumbo Netflix Falls Short in Big Screen Debut of ‘The Irishman’ The Irishman (Movie) Stuber, Scott Silicon Valley (Calif) Scorsese, Martin Sarandos, Ted Pacino, Al Netflix Inc Movies De Niro, Robert Cineplex Inc AMC Theatres

LOS ANGELES — After months of negotiations, Netflix couldn’t clinch the big-screen deal it wanted.

The streaming giant, which has roots in Silicon Valley, has tried to appease its top-shelf directors as it expands further into the movie business. But when it came a wide theatrical release for “The Irishman,” the $159 million gangster epic from director Martin Scorsese, Netflix fell short.

Netflix announced its fall releases on Tuesday with “The Irishman” set to debut in select theaters in New York and Los Angeles on Nov. 1 and then opening in theaters in cities across the country and internationally later that month. It will be available on Netflix on Nov. 27, the announcement said.

The main issue between the two is theatrical exclusivity and when the film would be available on Netflix. The major chains wanted “The Irishman” to be seen only in theaters for a longer period than Netflix was willing to accept.

With three and a half weeks of theatrical exclusivity, the rollout of the Scorsese film is similar to the modest theatrical run for “Roma,” its 2018 film from the director Alfonso Cuaron that won three Oscars.

Netflix executives, led by its film division chief Scott Stuber, negotiated for months with at least two major theatrical chains including AMC Theatres and Cineplex to allow its gangster epic to screen nationwide. AMC, for one, operates 11,000 theaters worldwide and is the largest U.S. exhibitor. But the chains insisted that Netflix play by the same rules as other studios like Warner Bros. and Disney and honor an exclusivity window, in which films screen in theaters for nearly three months before appearing anywhere else, including the streaming platforms.

“The Irishman” is a crime drama long planned by Mr. Scorsese that reunites the director with his cadre of frequent acting collaborators including Robert DeNiro, Harvey Keitel and Joe Pesci. For the first time, Mr. Scorsese directed Al Pacino, who plays Teamster leader Jimmy Hoffa in the film.

The film turned into a Netflix project in 2017 when Mr. Scorsese’s original studio, Paramount, balked at its production budget, which includes expensive de-aging technology that allows the actors to look the appropriate ages in this decade-spanning epic. The drama is expected to be one of Netflix’s top contenders in the Oscar race.

“The Irishman” is set to open the New York Film Festival on Sept. 27. Mr. Scorsese had been angling for an expansive release, according to two sources with knowledge of his thinking. The film’s debut reaffirms Netflix’s focus on growing its subscriber base, which stands at 151 million worldwide.

The company is still negotiating with smaller theater chains such as Landmark Theatres, according to two sources with knowledge of the talks. Most of those agreements will not feature the shared revenue deals traditionally agreed upon between distribution and exhibition companies. Instead, Netflix will rent out the entire theaters and no box office results will be reported.

With challenges from the Walt Disney Company, which plans to unveil its streaming service Nov. 12, and Apple debuting its own on an unspecified date this fall, as well as competition ahead from WarnerMedia and Comcast next spring, Netflix is spending billions of dollars to ensure subscribers don’t flee to other services.

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A Unicorn Lost in the Valley, Evernote Blows Up the ‘Fail Fast’ Gospel

Smiling cryptically, Ian Small, the chief executive of Evernote, handed me some socks. Nice ones: black in the calf, striped in the foot, with matching pops of sky blue at the toe, heel and welt. The knit was Japanese, dense and springy, and contained 1 percent polyurethane. Marketing language described them, insanely, as “smart covers for your feet” that shared design principles with productivity software.

Mr. Small had retrieved the socks from a small cabinet at Evernote’s headquarters in Redwood City, Calif., where coders work on its popular note-taking app. At the peak of Evernote’s success, as part of an ambitious plan to expand from software factory to lifestyle brand, the company sold the socks and other “exceptional products that satisfy our desires for greater ease and efficiency,” like high-end scanners and backpacks made by Côte&Ciel, a French boutique. The company even opened a physical storefront in its lobby called “Noteworthy by Evernote.” It gave the Evernote groupies — groupies! — who kept showing up at the office something to peruse.

But that was a century ago, in start-up years. When I visited Mr. Small in May, the shelves laden with branded goods were gone. There was a wall full of aging trophies, and in the back, an old mural describing the shop’s lofty vision was still faintly visible beneath a layer of Evernote-green paint.

Mr. Small was good-natured about it. “We treasure our history,” he said.

For a start-up, Evernote has a lot of it. Founded in 2004, it was among the first companies to ride the wave of smartphone adoption, and many expected it would achieve a triumphant initial public offering. Instead, the company cycled through four chief executives, several rounds of layoffs, three office closings and the shuttering of numerous side projects, including Japanese-made smart covers for your feet. Last September, when four top executives left at once, tech blogs declared that the company was in a “death spiral.”

In a season of multibillion-dollar I.P.O.s for Slack, Pinterest, Zoom, Uber, Lyft and others, Evernote is nowhere close. While younger start-ups are minting hundreds of millionaires and creating a new generation of semiretired tech millennials, Evernote is in the midst of a difficult turnaround led by Mr. Small, an unassuming, under-the-radar entrepreneur who took over in October.

In Silicon Valley, the idea that most start-ups won’t make it to a splashy public offering or acquisition is not just understood, but embraced. “Fail fast, fail often” is one of the region’s earliest and best-recognized catchphrases. The implication is that people and companies that don’t find success can transition, efficiently and without stigma, to more promising ventures. But Evernote’s struggles illustrate a harsher truth: For many start-ups of a certain size, failure rarely happens abruptly.

ImageWestlake Legal Group merlin_139921890_593269eb-b13e-42c3-a0c6-bb1f8f849eac-articleLarge A Unicorn Lost in the Valley, Evernote Blows Up the ‘Fail Fast’ Gospel Venture Capital Start-ups Small, Ian Silicon Valley (Calif) O'Neill, Christopher R (1972- ) Mobile Applications Initial Public Offerings Evernote Corp Computers and the Internet

As chief executive, Chris O’Neill laid off employees, scaled back side projects, canceled lavish perks (like a weekly sushi lunch and free house cleaners), shuttered three international offices, and hiked the price of an Evernote subscription. He left the company last year.CreditJason LeCras for The New York Times ORG XMIT: NPX

More often, after early momentum wanes, the missteps and bad press accumulate until a company enters a slow, difficult rehabilitation that stretches on for years. But in and around San Francisco, no one likes to talk about getting stuck in start-up purgatory. Once venture capital investors have sunk in considerable sums, they’re willing to let struggling companies flounder for years on the off chance they hit on something big. “They’re not in it for a break-even or a slight loss or a slight gain,” said Jeffrey Cohen, a bankruptcy lawyer at Lowenstein Sandler. “They’re willing to let it ride a little longer to see whether it explodes.”

It’s a common trap for the most recent generation of start-ups, which has been marked by the proliferation of “unicorns” worth $1 billion or more. For fledgling companies, taking enough investor money to become one of these magical ungulates was supposed to show customers, employees and the world that they were sure bets — that they were too special and big and valuable to fail. But many companies that chased three-comma valuations are now stuck trying to live up to almost impossible expectations.

Since 2015, according to CB Insights, a research firm, more than 40 unicorn companies have had “down rounds” or “down exits” — that is, investments or sales at reduced valuations. The list includes well-known brands like Shazam, the name-that-song app, and Jessica Alba’s consumer products start-up, the Honest Company.

Several unicorns have laid off staff in recent months, including Clover Health (which does health insurance), Udacity (online education) and Instacart (grocery delivery). Stumbles and shifts like that won’t kill a company, but they harm the perception that they are growing rapidly — and that, in turn, harms their ability to recruit, raise capital and, well, grow rapidly.

Evernote’s headquarters, bearing its green elephant logo, loom over Highway 101, where billboards advertise financial services to the latest class of I.P.O. millionaires. From the building’s fifth floor, Mr. Small looked out over the suburban sprawl of Silicon Valley. He pointed out the offices of companies that are younger than Evernote, including Box, a cloud storage company that went public in 2015. Its revenue is sixfold that of Evernote and its staff is nine times its size.

“There are companies in Silicon Valley that are rocket ships,” Mr. Small said, making a whistling noise and upward motion with his hand. He paused to contemplate how I’d render that sound in print and continued in the easy tone of light, well-practiced dad joke. “We’re a little more like the Beatles song. It is ‘A Long and Winding Road.’”

Hype — the jet fuel that propels hot start-ups — has a short memory. Remember FarmVille? The agrarian simulation was a phenomenon, topping 80 million users and leading its parent company, Zynga, to a valuation of $7 billion at the time of its 2011 I.P.O. But the buzz wore off as losses continued and the company cycled through chief executives. At various points, the value of Zynga’s cash stockpile plus its headquarters topped its entire market capitalization. This year the company sold its real estate for $600 million, netting a greater profit than it ever earned on its games.

Phil Libin in 2015. A showman-style chief executive, he once declared that Evernote aspired to be “the Nike for your mind.”CreditClodagh Kilcoyne/Getty Images

Lots of once-hyped companies live on the “Remember this?” spectrum. On one end, there is a cluster of fast flameouts — the YoElloPeachMeerkatStolenClinkleSecretColor coterie. On the other end is a group of hit start-ups that showed enough promise and raised enough money to stay alive even after they fell out of the zeitgeist. Remember Foursquare, the check-in app? It transformed into a location-tracking technology provider and raised $150 million in fresh funding in May. Remember Quora, the question-and-answer site? It “still exists,” Recode wrote in a burn of a headline recently, and plans to raise funding at a valuation of $2 billion.

“Remember Everything” is one of Evernote’s slogans. It’s been a remarkable journey. From its origins as a simple note-taking app, Evernote hit euphoric highs. Job-seekers submitted elaborate, unsolicited application videos, like Karen X. Cheng, a designer, who filmed herself performing a song she wrote about her dream gig at the company. (“I wanna help the world remember / I wanna go extend their brains,” she sang.) Some who did get hired describe feeling as if they’d won “American Idol.” The company reached unicorn status in 2012. The next year, Phil Libin, a showman-style chief executive, declared that Evernote aspired to be “the Nike for your mind.”

It seemed natural for Evernote the Lifestyle Brand to use its hundreds of millions in venture capital to expand in every direction. In addition to its flagship app, Evernote built a chat app, a recipe app, a contacts management app and a flashcard app. It hosted elaborate conferences for its partners and users. It sold business gear — including $32.95 Evernote-branded Moleskine notebooks — in an ambitious e-commerce effort. It struck a partnership to digitize Post-it notes. It had more than 150 million registered users, and Mr. Libin talked up his vision of a “100-year start-up.”

When Evernote’s growth began to slow in 2015, though, the company replaced Mr. Libin with Chris O’Neill, a former Google executive. He laid off employees, scaled back side projects, canceled lavish perks like a weekly sushi lunch and free house cleaners, shuttered three international offices, and hiked the price of an Evernote subscription. His strategy was to focus Evernote on business software, and compete with more robust enterprise offerings. But Evernote’s product lacked essential features, and the distinct versions of its apps on Windows, iOS and Android systems made collaboration across devices and teams difficult, former employees say. Sales of Evernote’s business product never exceeded 15 percent of revenue, according to two people familiar with the company.

Employees wishfully passed along rumors about a buyout from Microsoft or Google. A sense of malaise crept into team meetings, where employees gathered on a wide staircase with seat cushions in the center of the building under a large cardboard elephant head mount. “You got this collective sense of, ‘It’s fine, but it’s probably not going to be successful,’” a former employee said.

Start-ups rarely drop the veneer of perpetually “crushing it,” no matter how ugly things get. But in the summer and fall of 2018, four top executives quit. An August article in the New York Times Styles section about Mr. O’Neill’s workout routine came off as oblivious, and he soon left the company too. Within a few months of replacing him, Mr. Small calculated that he could not ignore the swell of angry message board posts and “death spiral” headlines.

He published an unusually frank blog post aimed at Evernote’s users in January. The company’s foundation was not strong, he wrote, and its products had developed a “unique collection of bugs and undesirable behaviors.” It would take most of the year to get all that fixed, he wrote, adding that “undoubtedly we will still disappoint some of you.”

Founded in 2004, Evernote was among the first start-ups to ride the smartphone wave, and a triumphant I.P.O. seemed possible. Instead, the company is in the midst of a difficult turnaround.CreditJim Wilson/The New York Times

Customers responded to his candor with a mix of optimism and skepticism, Mr. Small said. “The fact that we were able to tell the truth — that they already knew to be true — was a change of pace, not just for Evernote but for every tech-company relationship they probably have,” he said.

Now Mr. Small faces the challenge of recruiting engineers to fix Evernote’s “unique collection of bugs,” when they could be riding a bullet train to riches at a newer company. Hot start-ups can spend lavishly on engineering talent; they can always raise more if they’re growing quickly. Evernote has a different, more mature goal. It expects to reach positive cash flow this year, with annual revenue of nearly $100 million. “We used to be a movement,” Mr. Small said. “When we were a movement, we weren’t a business.”

Distaste for the venture-fueled model of hypergrowth is becoming more common among founders and executives, even ones whose reputations and bank accounts benefited from the narrative on the way up. Techies tend to blame amorphous entities — the press, investors or “Silicon Valley” in general — for the perils of hype.

It’s true that in many other contexts, a company like Evernote might be considered a success, and not some cautionary zombiecorn. “The core business of Evernote is what most companies outside of Silicon Valley would look on with envy,” said Vincent Toolan, Evernote’s former chief financial officer. “The problem is it’s in Silicon Valley.”

Roelof Botha, a partner at Sequoia Capital and a member of Evernote’s board, dismissed the idea of the company adrift as noise, expressing enthusiasm for its prospects. With Evernote, “the narrative around the company was more positive than reality,” he said. “Right now, the narrative is more negative than reality.”

Mr. Small also resisted the industry’s age-old boom and bust narrative. “Silicon Valley likes it when people stumble,” he said. “It makes good news.” But he pointed out that Evernote’s apps were still downloaded 50,000 times a day — user complaints and internal tumult notwithstanding.

The company, which has around half the employees it had at its peak, can even hire from a dedicated pool of users who persist in loving the app, he said. “We’re not hip right now, but to those people, we are cool,” he said. He has even rehired several former employees.

Having survived the “snark phase,” Mr. Small said, Evernote is now poised for a comeback narrative. In his view, tech industry insiders are rooting for the company to pull it off: “People kind of want the elephant to ride again.”

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Democratic Candidates Woo Silicon Valley for Donations, Then Bash It.

SAN FRANCISCO — Top Democrats in Washington and on the 2020 campaign trail are taking technology giants to task, calling them too big, too powerful and too careless about privacy. “The era of self-regulation is over,” Speaker Nancy Pelosi declared on Monday.

But just as Ms. Pelosi’s Democrats were preparing sweeping House hearings into the tech companies’ concentration of power, some of her party’s leading presidential candidates spent the weekend canvassing Silicon Valley to raise money from one of the nation’s wealthiest and most liberal bastions.

Mayor Pete Buttigieg filled his Saturday with no less than four fund-raisers in the Bay Area, with co-hosts that included a former top Facebook executive and Google official. It was at least Mr. Buttigieg’s third fund-raising trip to the region in the last three months. Senator Cory Booker was making his fourth trip to Silicon Valley to raise money since declaring for president in February. And Kamala Harris, California’s junior senator, was on her sixth tour of the Bay Area fund-raising circuit this year.

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The Democratic Party’s intensifying alarms about the technology giants’ monopolistic behavior, social media misinformation and lax privacy protections pose an unexpected dilemma for the 2020 field.

In a contest where purity tests on the left have already propelled leading campaigns to disavow super PACs and reject money from federal lobbyists, is tech money still politically acceptable? And can those who take it still be trusted to rein in the industry’s excesses?

The progressive base has already soured on Wall Street, fossil fuel and pharmaceutical cash. Silicon Valley had been, until recently, one of the last relatively untainted wellsprings from which to draw campaign contributions. Now, some, particularly on the left, say tech money is suspect, too.

“Many of the candidates are trying to have it both ways,” said Rebecca Katz, a Democratic strategist from the party’s progressive wing, who recently called on Democratic political consultants to stop representing corporate clients, “but it will be hard to be taken seriously as strong on this issue when you’re taking money hand over fist from Big Tech.”

The fraught Democratic balancing act came into sharp relief last weekend.

[Check out our tracker of the 2020 Democratic candidate field.]

House Democrats and Ms. Pelosi announced plans for an antitrust investigation into the largest tech companies and Senator Elizabeth Warren posed in front of a San Francisco billboard calling for breaking up Big Tech. Meanwhile, more than a dozen presidential candidates arrived in the city for the state Democratic convention. That was the public side of their trips; many maintained a busy private itinerary of fund-raisers powered in part by the immense wealth of the tech sector.

ImageWestlake Legal Group merlin_155789268_8dff66bb-6c13-4c98-acea-cbaa1d28a079-articleLarge Democratic Candidates Woo Silicon Valley for Donations, Then Bash It. Silicon Valley (Calif) Presidential Election of 2020 Harris, Kamala D Google Inc Campaign Finance Buttigieg, Pete (1982- ) Booker, Cory A Amazon.com Inc

Senator Elizabeth Warren has aggressively gone after Big Tech, accusing companies like Amazon of overly controlling the online marketplace and the items sold in it.CreditMason Trinca for The New York Times

Senators Kirsten Gillibrand, Amy Klobuchar and Ms. Harris all had finance events around the Bay Area on Friday (while Mr. Booker zipped to Seattle to raise money at the office of Nick Hanauer, a venture capitalist and early Amazon investor.) Mr. Buttigieg blitzed the region on Saturday, attending an event co-hosted by Chris Cox, Facebook’s former chief product officer and one of its initial engineers, and Scott Kohler, a corporate counsel to Google and former bundler for Hillary Clinton.

On Sunday, Mr. Booker returned for an event at the home of Jeff Jordan, a tech investor who had previously served as president of PayPal and OpenTable.

Former Vice President Joseph R. Biden Jr. was not in California over the weekend. But his finance team is tentatively planning a Silicon Valley swing at the end of June. In May, one of his Southern California event co-hosts was Eric Schmidt, the former Google chief executive.

Democrats mostly appear to be banking that the cash raised at such events outweighs any risk of backlash.

Mark Longabaugh, a Democratic strategist who advised Bernie Sanders in 2016 but is unaligned in 2020, said one reason is that most people still view tech giants “in a favorable light,” even if attitudes are shifting.

“They do not see these companies like Big Oil and the pharmaceutical companies,” he said. “There’s a distinction there.”

But as the Trump administration forges ahead with its own antitrust investigations into Amazon, Apple, Google and Facebook, the Democratic reliance on tech money could provide President Trump a political opening to depict Democrats as beholden to the technology giants.

At a forum in San Francisco, the 2020 candidate Beto O’Rourke linked the industry’s money to a law signed by Mr. Trump allowing internet providers access to sell browsing data without explicit consumer consent. “If you follow the dollars, who paid for that access, that influence, and those outcomes, you begin to understand what’s at play,” he said.

Most of the 2020 Democrats are aligned on stiffening regulations and tech industry scrutiny.

But Ms. Warren, in particular, has gone much further, accusing companies like Amazon of improperly controlling the online marketplace and the items sold in it. She has shunned holding fund-raisers as a presidential candidate, though she has raised money from Silicon Valley in the past.

Ms. Warren has surpassed Senator Bernie Sanders as tech’s most insistent critic (he recently embraced breaking up Facebook, and he has hammered Amazon for its low wages).

Senator Cory Booker attended Stanford and once was an investor in an internet start-up.CreditSarahbeth Maney for The New York Times

Ro Khanna, a California congressman who represents and has raised money heavily from Silicon Valley, serves as national co-chair of Mr. Sanders’s campaign, though he is not fully aligned with Mr. Sanders on tech matters. Mr. Khanna said “calling for a sledgehammer approach” to breaking up Big Tech was “bad policy” when a “scalpel” is needed.

“People should, in my view, be proud of having support from technology leaders,” Mr. Khanna said.

Silicon Valley is not monolithic. Some companies profit from user data. Some make money selling hardware. Others hope to break into markets now dominated by the giants. While Ms. Warren’s unyielding rhetoric has alienated some tech leaders, political donors and executives in Silicon Valley said that there is a surprising sympathy for broader calls to increase oversight of the industry’s biggest players.

“It’s my sense that a lot of people in Silicon Valley think tech has gotten too big, that there’s overreach,” said Chris Hughes, a Facebook co-founder who recently called for the company’s breakup.

“There’s a sense that people know that mistakes were made, and there’s a search for solutions,” Mr. Hughes added.

Mr. Hughes has contributed to four Democratic candidates this year: Mr. Booker, Ms. Warren, Mr. Buttigieg and Ms. Harris.

Three of the most aggressive candidates chasing Silicon Valley money have been Mr. Booker, Mr. Buttigieg and Ms. Harris, according to interviews with donors and event invitations obtained by The New York Times.

All three have ties to the Valley. Mr. Booker attended Stanford and once was an investor in an internet start-up (another investor, the billionaire LinkedIn founder Reid Hoffman, recently hosted a fund-raiser for Mr. Booker).

Mr. Booker also worked closely with Mark Zuckerberg when the Facebook founder donated $100 million to revamp Newark schools, an undertaking that got mixed reviews.

Mr. Buttigieg, who as a Harvard undergraduate was one of Facebook’s first several hundred users, attended the university at the same time as Facebook’s founders and has quickly cultivated relationships across the Valley.

Pete Buttigieg was one of Facebook’s first several hundred users and attended Harvard at the same time as Facebook’s founders.CreditMason Trinca for The New York Times

Yet all have expressed concerns about Big Tech’s dominance.

Mr. Buttigieg recently went on record in support of Mr. Hughes’s call to break up Facebook, saying his old schoolmate had “made a very convincing case” about “these tech companies as monopoly giants.”

“There needs to be tools to deal with that, up to and including preventing or reversing mergers,” Mr. Buttigieg said in a recent podcast.

Going back several years, Mr. Booker has questioned the dominance of companies including Google and Amazon. In a recent interview with The Times, Mr. Booker said he was planning to roll out an internet security platform and has deepening concerns about companies “able to use your data for your profit.” But when asked about Ms. Warren’s demand that big tech firms be broken up, he replied in a recent television appearance, “That sounds more like a Donald Trump thing to say.”

In the Senate, Ms. Harris aggressively questioned Facebook executives last year, and this year she said on CNN that government officials “need to take a serious look at breaking up Facebook.”

Matt Stoller, a fellow at the Open Market Institute, who previously worked for the Senate Budget Committee under Mr. Sanders and is a critic of the consolidation of power in the tech industry, said there were differences in the deference that candidates gave to Silicon Valley leaders.

“Buttigieg and Harris treat them like they’re special,” Mr. Stoller said. “Warren treats them as they’re just citizens. Booker goes back and forth.”

Ali Partovi, a Silicon Valley entrepreneur who hosted a fund-raiser for Mr. Booker, said he sees no evidence that donors are dissuaded by talk about a crackdown on Big Tech.

“I find that people vote and donate in service of their principles and beliefs about what they think is right, not just their self-interest,” Mr. Partovi said.

The tech economy remains a crucial source of funds for congressional Democrats, too.

Later this month, Ms. Pelosi will collect checks at a San Francisco law firm that has represented tech companies, asking for as much as $19,600 to help seven of her vulnerable California colleagues. That same day, her political committee is holding an event at the home of John Thompson, the current chairman of Microsoft and the former chief executive of Symantec.

The price to chair the luncheon: $50,000.

Real Estate, and Personal Injury Lawyers. Contact us at: https://westlakelegal.com 

Democrats Take Aim at Silicon Valley. They Take Its Cash, Too.

SAN FRANCISCO — Top Democrats in Washington and on the 2020 campaign trail are taking technology giants to task, calling them too big, too powerful and too careless about privacy. “The era of self-regulation is over,” Speaker Nancy Pelosi declared on Monday.

But just as Ms. Pelosi was preparing to start an antitrust investigation, some of her party’s leading presidential candidates spent the weekend canvassing Silicon Valley to raise money from one of the nation’s wealthiest and most liberal bastions.

Mayor Pete Buttigieg filled his Saturday with no less than four fund-raisers in the Bay Area, with co-hosts that included a former top Facebook executive and Google official. It was at least Mr. Buttigieg’s third fund-raising trip to the region in the last three months. Senator Cory Booker was making his fourth trip to Silicon Valley to raise money since declaring for president in February. And Kamala Harris, California’s junior senator, was on her sixth tour of the Bay Area fund-raising circuit this year.

[Sign up for our politics newsletter and join our conversation about the 2020 presidential race.]

The Democratic Party’s intensifying alarms about the technology giants’ monopolistic behavior, social media misinformation and lax privacy protections pose an unexpected dilemma for the 2020 field.

In a contest where purity tests on the left have already propelled leading campaigns to disavow super PACs and reject money from federal lobbyists, is tech money still politically acceptable? And can those who take it still be trusted to rein in the industry’s excesses?

The progressive base has already soured on Wall Street, fossil fuel and pharmaceutical cash. Silicon Valley had been, until recently, one of the last relatively untainted wellsprings from which to draw campaign contributions. Now, some particularly on the left say, tech money is suspect, too.

“Many of the candidates are trying to have it both ways,” said Rebecca Katz, a Democratic strategist from the party’s progressive wing, who recently called for campaign advisers to stop taking on corporate clients, “but it will be hard to be taken seriously as strong on this issue when you’re taking money hand over fist from Big Tech.”

The fraught Democratic balancing act came into sharp relief last weekend.

[Check out our tracker of the 2020 Democratic candidate field.]

House Democrats and Ms. Pelosi announced plans for an antitrust investigation into the largest tech companies and Senator Elizabeth Warren posed in front of a San Francisco billboard calling for breaking up Big Tech. Meanwhile, more than a dozen presidential candidates arrived in the city for the state Democratic convention. That was the public side of their trips; many maintained a busy private itinerary of fund-raisers powered in part by the immense wealth of the tech sector.

ImageWestlake Legal Group merlin_155789268_8dff66bb-6c13-4c98-acea-cbaa1d28a079-articleLarge Democrats Take Aim at Silicon Valley. They Take Its Cash, Too. Silicon Valley (Calif) Presidential Election of 2020 Harris, Kamala D Google Inc Campaign Finance Buttigieg, Pete (1982- ) Booker, Cory A Amazon.com Inc

Senator Elizabeth Warren has aggressively gone after Big Tech, accusing companies like Amazon of overly controlling the online marketplace and the items sold in it.CreditMason Trinca for The New York Times

Senators Kirsten Gillibrand, Amy Klobuchar and Ms. Harris all had finance events around the Bay Area on Friday (while Mr. Booker zipped to Seattle to raise money at the office of Nick Hanauer, a venture capitalist and early Amazon investor.) Mr. Buttigieg blitzed the region on Saturday, attending an event co-hosted by Chris Cox, Facebook’s former chief product officer and one of its initial engineers, and Scott Kohler, a corporate counsel to Google and former bundler for Hillary Clinton.

On Sunday, Gov. John Hickenlooper raised money in the heart of Silicon Valley as Mr. Booker returned for an event at the home of Jeff Jordan, a tech investor who had previously served as president of PayPal and OpenTable.

Joseph R. Biden Jr. was not in California over the weekend. But his finance team is tentatively planning a Silicon Valley swing at the end of June. In May, one of his Southern California event co-hosts was Eric Schmidt, the former Google chief executive.

Democrats mostly appear to be banking that the cash raised at such events outweighs any risk of backlash.

Mark Longabaugh, a Democratic strategist who advised Bernie Sanders in 2016 but is unaligned in 2020, said one reason is that most people still view tech giants “in a favorable light,” even if attitudes are shifting.

“They do not see these companies like Big Oil and the pharmaceutical companies,” he said. “There’s a distinction there.”

But as the Trump administration forges ahead with its own antitrust investigations into Amazon, Apple, Google and Facebook by the Justice Department and the Federal Trade Commission, the Democratic reliance on tech money could provide President Trump a political opening to depict the Democrats as beholden to the technology giants.

At a forum in San Francisco, the 2020 candidate Beto O’Rourke linked the industry’s money to a law signed by Mr. Trump allowing internet providers access to sell browsing data without explicit consumer consent. “If you follow the dollars, who paid for that access, that influence, and those outcomes, you begin to understand what’s at play,” he said.

Most of the 2020 Democrats are aligned on stiffening regulations and tech industry scrutiny.

But Ms. Warren, in particular, has gone much further, accusing companies like Amazon of improperly controlling the online marketplace and the items sold in it. She has shunned holding fund-raisers as a presidential candidate, though she has raised money from Silicon Valley in the past.

Ms. Warren has surpassed Senator Bernie Sanders as tech’s most insistent critic (he recently embraced breaking up Facebook and he has hammered Amazon for its low wages).

Senator Cory Booker attended Stanford and once was an investor in an internet start-up.CreditSarahbeth Maney for The New York Times

Ro Khanna, a California congressman who represents and has raised money heavily from Silicon Valley, serves as national co-chair of Mr. Sanders’s campaign, though he is not fully aligned with Mr. Sanders on tech matters. Mr. Khanna said “calling for a sledgehammer approach” to breaking up Big Tech was “bad policy” when a “scalpel” is needed.

“People should, in my view, be proud of having support from technology leaders,” Mr. Khanna said. “I don’t think there is anything wrong with that.”

Silicon Valley is not monolithic. Some companies profit from user data. Some make money selling hardware. Others hope to break into markets now dominated by the giants. While Ms. Warren’s unyielding rhetoric has alienated some tech leaders, political donors and executives in Silicon Valley said that there is a surprising sympathy for broader calls to increase oversight of the industry’s biggest players.

“It’s my sense that a lot of people in Silicon Valley think tech has gotten too big, that there’s overreach,” said Chris Hughes, a Facebook co-founder who has recently called for the company’s breakup, adding that the conversation on Big Tech has reached “a turning point.”

“There’s a sense that people know that mistakes were made and there’s a search for solutions,” Mr. Hughes added. “And there are some folks that are trying to patch things up, and there are some who are questioning the structural foundations of the way the internet has evolved.”

Mr. Hughes and his husband, Sean Eldridge, have contributed to four Democratic candidates this year: Mr. Booker, Ms. Warren, Mr. Buttigieg and Ms. Harris.

Three of the most aggressive candidates chasing Silicon Valley money have been Mr. Booker, Mr. Buttigieg and Ms. Harris, according to interviews with donors and event invitations obtained by The New York Times.

All three have substantial ties to the Valley. Mr. Booker attended Stanford and once was an investor in an internet start-up (another investor, the billionaire LinkedIn founder Reid Hoffman, recently hosted a fund-raiser for Mr. Booker).

Mr. Booker also worked closely with Mark Zuckerberg when the Facebook founder donated $100 million to revamp Newark schools, an undertaking that got mixed reviews.

Mr. Buttigieg, who as a Harvard undergraduate was one of Facebook’s first several hundred users, attended the university at the same time as Facebook’s founders and has quickly cultivated relationships across the Valley.

Pete Buttigieg was one of Facebook’s first several hundred users and attended Harvard at the same time as Facebook’s founders.CreditMason Trinca for The New York Times

Ms. Harris, a Bay Area native, has raised the most of any 2020 candidate in the first quarter from employees of companies in the Internet Association, a lobbying arm of the tech industry in Washington D.C., according to an analysis of federal records.

Yet all have expressed concerns about Big Tech’s dominance.

Mr. Buttigieg recently went on record in support of Mr. Hughes’s call to break up Facebook, saying his old schoolmate had “made a very convincing case” about “these tech companies as monopoly giants.”

“There needs to be tools to deal with that, up to and including preventing or reversing mergers,” Mr. Buttigieg said in a recent podcast.

Going back several years, Mr. Booker has questioned the dominance of companies including Google and Amazon. In a recent interview with The Times, Mr. Booker said he was planning to roll out an internet security platform and has deepening concerns about companies “able to use your data for your profit.” But when asked about Ms. Warren’s demand that big tech firms be broken up, he replied in a recent television appearance, “That sounds more like a Donald Trump thing to say.”

In the Senate, Ms. Harris aggressively questioned Facebook executives last year, and this year she said on CNN that government officials “need to take a serious look at breaking up Facebook.”

Matt Stoller, a fellow at the Open Market Institute and an outspoken critic of the consolidation of power in the tech industry, said there were clear differences in the deference that candidates gave to Silicon Valley leaders.

“Buttigieg and Harris treat them like they’re special,” Mr. Stoller said. “Warren treats them as they’re just citizens. Booker goes back and forth.”

Ali Partovi, a Silicon Valley entrepreneur who hosted a fund-raiser for Mr. Booker this year, said he hasn’t seen evidence that donors are dissuaded by talk about a crackdown on Big Tech.

“I find that people vote and donate in service of their principles and beliefs about what they think is right, not just their self-interest,” Mr. Partovi said. “What I like about Booker in general is that he doesn’t pander to donors.”

The tech economy remains a crucial source of funds for congressional Democrats, too.

Later this month, Ms. Pelosi will collect checks at a San Francisco law firm that has represented tech companies, asking for as much as $19,600 to help seven of her vulnerable California colleagues. That same day, her political committee is holding an event at the home of John Thompson, the current chairman of Microsoft and the former chief executive of Symantec.

The price to chair the luncheon: $50,000.

Real Estate, and Personal Injury Lawyers. Contact us at: https://westlakelegal.com