Confetti rained down at the Nasdaq as Etsy Inc. ’s stock popped 94% in early trading. But all its CEO Chad Dickerson felt was dread.
His toddler had vomited and was throwing a tantrum. Mr. Dickerson, too, felt sick to his stomach as he worried about how the online crafts marketplace would live up to the hype. Back in the office, employees celebrated by dousing him with a bucket of ice water. He recalls the chill he felt the rest of the day in a cold, wet suit.
It was “this moment of success and this feverish insanity,” says the now-47-year-old Mr. Dickerson, who left as Etsy’s chief executive in 2017, two years after the initial public offering. Amid the confetti, he thought: “If we don’t maintain this price…it’s just going to be brutal.”
This year is set to be a huge one for startup IPOs. Going public is a cinematic moment for founders, CEOs and early employees, one that can turn years of hard work into immense wealth. But off-camera, the startup world has a dark side. Under the veneer of fancy parties and multibillion-dollar valuations, many founders and early-startup executives are striving to build pioneering businesses while wrestling with issues like anxiety, drug addiction, insomnia, depression and binge eating.
Stress, of course, is a part of any leadership role, and startup leaders often have more resources than most to cope with mental-health woes. But it is also becoming clear that the swashbuckling creativity that pushes many startup founders to take bold leaps often comes with inner demons.
Entrepreneurs were 50% more likely to report having a lifetime mental-health condition and reported significantly higher rates of depression, attention-deficit disorder, substance abuse and bipolar disorder than a control group, according to a 2016 paper by researchers at the University of California San Francisco, UC Berkeley, and Stanford University, who surveyed more than 200 founders.
Some entrepreneurs have “a high degree of energy, a low need for sleep, a drive that seems far beyond ordinary driven people and a vivid imagination,” says Kerry Sulkowicz, a New York psychoanalyst who advises CEOs. These traits allow them to “keep going when everybody tells you what you’re doing is crazy” but also makes them vulnerable to mental-health issues, he says.
A massive workload doesn’t help—nor that young entrepreneurs are bombarded by what some call “hustle porn,” the notion that working nonstop is a badge of honor.
Serial entrepreneur Kwiri Yang, 31, says she found herself in a “stress cage” as head of strategy at Fuhu, a children’s tablet maker. After Fuhu was sold to Mattel Inc. in a bankruptcy auction in 2016, she says she fell physically ill and grew severely depressed, cycling through seven therapists and three executive coaches before finding support from other founders.
Even established internet entrepreneurs say they aren’t immune to the crushing pressures.
“All the way through every fundraise, until you find your lead investor, you feel like crap because every other investor you talk to is telling you how much your business sucks,” said Kimbal Musk, 46, who says he fell into a depression after selling his and his brother Elon’s startup Zip2 for $307 million, making more money than he’d ever dreamed of at age 27.
Feeling lost, he enrolled in cooking school and went on to found food startups Kitchen Restaurant Group, Big Green and Square Roots.
Rebecca Jean Alonzi, 34, says she developed a dependence on sugary foods to fuel long nights building her farm-to-office food-service company Nourish Inc. As orders rolled in from Silicon Valley startups to cater their office spreads, she gained 30 pounds. She joined Overeaters Anonymous and got on a track to lose weight. Then she found herself having trouble focusing. A psychiatrist diagnosed her with attention-deficit hyperactivity disorder in 2012 and prescribed Adderall, a stimulant, which she says made her “skinny, bitchy and very productive.”
Within a year, she began having headaches and quit Adderall, concluding that amid building a health-food company she was hurting her own body. “I cared so deeply about making a difference that I was willing to push myself past my limit,” she says. “What I later learned is there are ways to achieve superhumanity that didn’t involve self-sacrifice.” Ms. Alonzi groomed a new CEO who took over this year, but she remains involved at Nourish as a chef-entrepreneur focused on new projects. She now incorporates into her routine “regenerative” activities like deep breathing, walks without a cellphone and barefoot hikes.
While many entrepreneurs find ways to deal with the pressure, some become increasingly destructive.
Brandon Truaxe’s hyperenergetic tendencies helped him build a cult beauty brand with hundreds of employees. Mr. Truaxe ran much of Toronto-based Deciem Inc. himself, sleeping little and using ephedrine and caffeine, said Riyadh Swedaan, his boyfriend of 11 years.
As the company grew, the pressure mounted. Mr. Swedaan said Mr. Truaxe started using crystal methamphetamine around early 2018, leading to increasingly erratic behavior. In October, Deciem investor Estée Lauder Co. took legal action, alleging that Mr. Truaxe had made hundreds of “disturbing posts” on Deciem’s social-media accounts, including threats, and leased a private plane and a new headquarters without consulting Deciem’s board. A spokeswoman for Deciem declined to comment.
The lawsuit led to Mr. Truaxe being removed from the company. He was hospitalized three times last year as a result of hallucinations from heavy drug use, twice in London and once in Canada, said Mr. Swedaan, who blamed the drugs for Mr. Truaxe’s downward spiral.
In January, Mr. Truaxe died after falling from his 32nd-floor condo.
An oft-cited issue in tech circles is that many startups fail because of people problems, not business issues. In a 2016 study, 92% of more than 13,000 venture capitalists surveyed by the National Bureau of Economic Research identified the management team as the most important factor in startup failures. “It is shocking how often startups fail because of the personality flaws and deep-seated traumas of their founders and execs,” said Garry Tan, managing partner at startup investor Initialized Capital, in a tweet.
The investments, sometimes billions of dollars, riding on founders’ ability to function keep many from talking about their struggles, says Ben Tauber, a Silicon Valley executive coach at Velocity Group. “If you talk with anyone, they say they are killing it,” Mr. Tauber says. Meanwhile, “inside they are dying.”
One common reason for distress, he says, is that founders and startup executives tend to derive much of their sense of self-worth from their company’s success.
“I think people are unprepared for how hard and awful it is going to be to start a company. I certainly was,” said Parker Conrad, the ousted former CEO of Zenefits, which achieved a $4.5 billion valuation in 2015 before running into numerous problems. Mr. Conrad, who now runs a human-resources software startup called Rippling, said stress-eating would cause his weight to soar during a big fundraising.
“I remember crying alone in my bed,” says Alan Gertner, 35, a former Google executive who left in 2015 to go into the cannabis business. When he sold his startup Hiku Brands, a Canadian marijuana retailer, last year for hundreds of millions of dollars, he said he felt little joy, only flickers of relief.
Founders often have more influence over their companies’ creative and strategic trajectories than leaders of established firms. As a result, their struggles can have outsize business consequences.
In 2017, major backers of Uber Technologies Inc. demanded the ouster of founder Travis Kalanick following a spate of scandals; Mr. Kalanick acknowledged that he needed to grow up. He declined to comment through a spokesman.
Discord between the two co-founders of HQ Trivia and the subsequent death of one of them, Colin Kroll, from a drug overdose threw the once-hot game-show app into disarray. “The company went through a difficult time following this horrible loss, but the core team has banded together,” said Rus Yusupov, HQ Trivia’s other co-founder, in an emailed statement.
Startup executives use a variety of “hacks” to stay mentally fit. Kimbal Musk recommends everyone “leave the planet” in some way; he slow-scrambles eggs as a form of morning meditation and goes to Burning Man every year. Several CEOs, including Zillow CEO Richard Barton, write in gratitude journals every morning.
Ms. Yang, formerly of Fuhu, has created LifeGyde and Second Time Founders, two startups focused on fostering healthy growth at young companies. “The health and well-being of the founder amplifies to their employees,” she says.
Through the grind of building Twitter from a scrappy startup to a public company, its former CEO Dick Costolo says he amped up his workouts: running, CrossFit, handstands, anything that could take his mind off work. Managing the stress was a persistent mental-health challenge, the 55-year-old said. “I had to do things to create a space in myself. I was constantly obsessing. You wake up at 3 a.m. in the morning and say, ‘What am I going to do about this?”
Mr. Costolo stepped down in 2015, two years after taking Twitter public, and is now an adviser to high-growth startups, counseling founders to try to maintain an evenness during the highs and lows.
Mark Pincus says his time at social game-maker Zynga has been an emotional roller coaster of sometimes extreme stress. He likened a founder to a war general tasked with telling his troops that they have to abandon safety, face the gunfire and run to the next foxhole. The 53-year-old says triathlons, surfing and weekly coaching on personal and professional matters has helped him navigate challenges. After jump-starting a turnaround, Mr. Pincus stepped down as CEO and later relinquished voting control to become nonexecutive chairman.
In part to help founders manage tough transitions, Mr. Pincus is on the cusp of unveiling a new venture fund called Reinvent Capital to fund companies through second acts and encourage founders to stay involved as entrepreneurs-in-chief.
A few venture-capital firms are now focusing more on developing founders as human beings rather than just CEOs.
“The prevalent view of startup founders in Silicon Valley is a delusion that in order to succeed, in order to build a high-growth company, you need to burn out,” says media mogul Arianna Huffington, a startup investor, Uber board member and CEO of her own wellness-focused company, Thrive Global.
Alpha Bridge Ventures has created a program to help support founders’ well-being. Kari Sulenes, its executive director, says digestive and autoimmune disorders can be exacerbated by stress. Founders’ “expectations for health are so low that even when they have something like Lyme disease, they think that’s just something to push through,” Dr. Sulenes said.
For Etsy’s Mr. Dickerson, the pressures eventually did mount. Two years after the IPO, the stock had dropped more than 30% from the listing price and the board fired him. After a low period, he gradually came to appreciate life as it was, thankful for his old experiences and ready to share his knowledge with others. Now he’s an executive coach.
“A whole new world kind of opened to me. I wasn’t rushing to the subway, wasn’t thinking about some deal,” he says. “I was able to bring my mind into the place that I was.”
The effectiveness of action depends on the source from which it springs. If it is coming out of the false self with its shadow side, it is severely limited. If it is coming out of a person who is immersed in God, it is extremely effective. The contemplative state, like the vocation of Our Lady, brings Christ into the world. —Thomas Keating 
.. I founded the Center for Action and Contemplation in 1987 because I saw a deep need for the integration of both action and contemplation. Over the years, I met many social activists who were doing excellent social analysis and advocating for crucial justice issues, but they were not working from an energy of love. They were still living out of their false self with the need to win, the need to look good—attached to a superior, politically correct self-image.
They might have the answer, but they are not themselves the answer. In fact, they are often part of the problem. That’s one reason that most revolutions fail and too many reformers self-destruct from within. For that very reason, I believe, Jesus and great spiritual teachers first emphasize transformation of consciousness and soul. Without inner transformation, there is no grounded or lasting reform or revolution. When subjugated people rise to power, they often become as dominating as their oppressors because the same demon of power hasn’t been exorcised in them.
We are easily allured by the next new thing, a new agenda that looks like enlightenment. And then we discover it’s run by unenlightened people who, in fact, love themselves first of all but do not love God or others. They do not really love the Big Truth, but they often love control. Too often, they do not love freedom for everybody but just freedom for their own ideas.
Untransformed liberals often lack the ability to sacrifice the self or create foundations that last. They can’t let go of their own need for change and cannot stand still in a patient, compassionate, and humble way. It is no surprise that Jesus prayed not just for fruit, but “fruit that will last” (John 15:16). Untransformed conservatives, on the other hand, tend to idolize anything that lasts, but then avoid the question, “Is it actually bearing any fruit?” This is the perennial battle between idealism and pragmatism, or romanticism and rationalism.
If we are going to have truly prophetic people who go beyond the categories of liberal and conservative, we have to teach them some way to integrate their needed activism with a truly contemplative mind and heart. I’m convinced that once you learn how to look out at life from the contemplative eyes of the True Self, your politics and economics are going to change on their own. I don’t need to teach you what your politics should or shouldn’t be. Once you see things contemplatively, you’ll begin to seek the bias from the bottom instead of the top, you’ll be free to embrace your shadow, and you can live at peace with those who are different. From a contemplative stance, you’ll know what action is yours to do—and what is not yours to do—almost naturally.
Arguably, that moment proved a precursor to this one as conservatives angry at his apostasy, led by a onetime backbench congressman from Georgia named Newt Gingrich, rose to power within the Republican Party and toppled the old establishment. The harder-edged Gingrich revolution in some ways foreshadowed Mr. Trump’s extraordinary takeover of the party.
Mr. Meacham said the current world of cable talk and relentless partisanship took shape during Mr. Bush’s era. “He saw it all coming, and he didn’t like it,” he said.
Mark K. Updegrove, the author of “The Last Republicans,” about the two Bush presidencies, said, “In so many ways, Bush was the antithesis of the Republican leadership we see today.” He embodied, Mr. Updegrove added, “the
- civility and
of the best of the World War II generation. He played tough but fair, making friends on both sides of the aisle and rejecting the notion of politics as a zero-sum game.”
.. For all of the condolences and tributes pouring in to the Bush home in Houston from every corner of the world on Saturday, Mr. Trump’s very presidency stands as a rebuke to Mr. Bush. Never a proponent of “kinder and gentler” politics, Mr. Trump prefers a brawl, even with his own party. The “new world order” of free-trade, alliance-building internationalism that Mr. Bush championed has been replaced by Mr. Trump’s “America First” defiance of globalism.
.. Mr. Trump has demonstrated that he sees the go-along-to-get-along style that defined Mr. Bush’s presidency as inadequate to advance the nation in a hostile world. Gentility and dignity, hallmarks of Mr. Bush, are signs of weakness to Mr. Trump. In his view, Mr. Bush’s version of leadership left the United States exploited by allies and adversaries, whether on economics or security.
.. Mr. Bush was, in effect, president of the presidents’ club, the father of one other commander in chief and the father figure to another, Bill Clinton. Jimmy Carter always appreciated that Mr. Bush’s administration treated him better than Ronald Reagan’s or Mr. Clinton’s, while Barack Obama expressed admiration for the elder Mr. Bush when he ran for the White House.
.. Mr. Obama was among the last people to see Mr. Bush alive.
.. “What the hell was that, by the way, thousand points of light?” Mr. Trump asked scornfully at a campaign rally in Great Falls, Mont., in July. “What did that mean? Does anyone know? I know one thing: Make America great again, we understand. Putting America first, we understand. Thousand points of light, I never quite got that one.”
.. “It’s so easy to be presidential,” Mr. Trump said at a campaign rally in Wheeling, W.Va. “But instead of having 10,000 people outside trying to get into this packed arena, we’d have about 200 people standing right there. O.K.? It’s so easy to be presidential. All I have to do is ‘Thank you very much for being here, ladies and gentlemen. It’s great to see you off — you’re great Americans. Thousand points of light.’ Which nobody has really figured out.”
.. In 1988, when Mr. Bush was seeking the presidency, Mr. Trump offered himself as a running mate. Mr. Bush never took the idea seriously, deeming it “strange and unbelievable,”
.. “I don’t know much about him, but I know he’s a blowhard. And I’m not too excited about him being a leader.” Rather than being motivated by public service, Mr. Bush said, Mr. Trump seemed to be driven by “a certain ego.”
My friend Tyler Cowen argues that Jordan Peterson is the most influential public intellectual in the Western world right now, and he has a point. Peterson, a University of Toronto psychologist, has found his real home on YouTube, where his videos have attracted something like 40 million views.
In his videos, he analyzes classic and biblical texts, he eviscerates identity politics and political correctness and, most important, he delivers stern fatherly lectures to young men on how to be honorable, upright and self-disciplined — how to grow up and take responsibility for their own lives.
.. His worldview begins with the belief that life is essentially a series of ruthless dominance competitions. The strong get the spoils and the weak become meek, defeated, unknown and unloved.
For much of Western history, he argues, Christianity restrained the human tendency toward barbarism. But God died in the 19th century, and Christian dogma and discipline died with him. That gave us the age of ideology, the age of fascism and communism — and with it, Auschwitz, Dachau and the gulag.
.. Since most conflict is over values, we’ve decided to not have any values. We’ll celebrate relativism and tolerance.
.. Chaos, the eternal feminine, is also the crushing force of sexual selection. Women are choosy maters. … Most men do not meet female human standards.”
.. Life is suffering, Peterson reiterates. Don’t be fooled by the naïve optimism of progressive ideology. Life is about remorseless struggle and pain. Your instinct is to whine, to play the victim, to seek vengeance.
.. “The individual must conduct his or her life in a manner that requires the rejection of immediate gratification, of natural and perverse desires alike.”
.. Instead, choose discipline, courage and self-sacrifice.
.. Much of Peterson’s advice sounds to me like vague exhortatory banality. Like Hobbes and Nietzsche before him, he seems to imagine an overly brutalistic universe, nearly without benevolence, beauty, attachment and love. His recipe for self-improvement is solitary, nonrelational, unemotional. I’d say the lives of young men can be improved more through loving attachment than through Peterson’s joyless and graceless calls to self-sacrifice.