Approximately 1000 hours: I arrive at the San Francisco headquarters of one Maureen Taylor. 1002 hours: I’m offered a glass of water. 1003 hours: I decline the greeter’s offer of a glass of water. 1004 hours: Taylor sweeps in. She is intimidatingly elegant, with Susan Sarandon looks. 1005 hours: We enter what Taylor calls the Situation Room.
The Situation Room: At 1006 hours, Taylor gives me the rundown on her squadrons, parked outside, clacking away serenely on MacBooks. By approximately 1020 hours, she has begun to diagnose a casual problem I have mentioned at work. Easy, she says. She could coach me through it in a snap, making it a “win-win.” You believe her: She speaks rapidly, exudes confidence. If you are lucky enough to work with her, you will leave her presence with some of that confidence. Maureen Taylor is, in trade parlance, an executive coach, but her work so eludes titles that when you look up her company, SNP Communications, you find only this tagline on the homepage: “Search the world for the good people and help them make their truth persuasive.” To know just how good Maureen Taylor is, you have to already know who Maureen Taylor is. And if you know who Maureen Taylor is, you might just be on your way to Being Somebody.
The Somebodies who enter the Situation Room or seek guidance from Taylor (who charges around $750 an hour but slacks up on that for promising young founders) — some startuppers, others seasoned executives — bring a bevy of troubles that probably seem distant for most workers of the world. Perhaps their knees quiver during presentations, or they’ve got a version of The King’s Speech. Novice founders holding huge sums of cash may not know what to do with it all. A disagreement with a co-founder, an inability to command a room at an all-hands team meeting.
These company leaders must seem chill, must be “crushin’ it” to colleagues and investors (who could replace them), must seem accessible to their employees, must sustain a level of true, pure belief in their cause at all times. So long to the man in the gray flannel suit; we have arrived at the CEO in the gray American Apparel hoodie, who is supposed to look like our cool, successful older sibling. Founders walk a “very lonely road” at the top, says Rob Bailey, partner at the investment firm Akkadian Ventures and a big proponent of coaches.
And so the unlikely winner in this game is the HR world. Once, getting packaged off to a coach was a remedial measure, a sign you needed serious “help” managing anger or the like. Today, lacking a coach is like playing president without a security adviser. In the Valley, in particular, the practice is so popular that investors keep a Rolodex of about eight to 10 rubber-stamped coaches to recommend to promising founders in their portfolios. They want to provide “every possible advantage,” says Katie Hughes, talent partner at DFJ Venture, which has invested in billion-dollar companies such as Skype, SpaceX, Tesla and Box. The gospel of this new generation of HR is Harvard Business School professor Noam Wasserman’s 2012 book, The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup. Those pitfalls, Wasserman concluded, after studying 10,000 founders of 4,000 startups, can be described in two deceptively simple words: people problems.
People problems are not only the troubles of the ruling class. Just consider the ongoing debate about the plight of the American white-collar worker. From The New York Times’ explosive story critiquing Amazon’s tough work environment to perks wars at Silicon Valley startups, management has never been such a hot topic. Throw in the Lean In–ers, the question of whether women should want it all and catchphrases like “toxic work culture,” and you might understand a CEO’s need for a guru.
Coaches can help ambitious but stretched founders stay sane and be their best selves. They can help them set priorities. They can speak the lingo. They can and do become close advisers and friends. But they have their limits. Taylor is adamant about her get-it-done style — she’s no shrink. But what of other limitations? An old narrative about coaches, soft-skilled types, is that they should be treated with skepticism, a few steps above Internet self-help charlatans. The more updated question, though, is this: How much can anyone, even the world’s smartest coach, do for the nonstop work cultures that create so much agita? Coaches are, after all, soothsayers residing within the system. They must become insiders to court the insiders. They are themselves entrepreneurs. And they are not merely doing good deeds: They take their recompense not just in cash and credit, but also equity.
Indeed, hearing how coaches make it is much like hearing how startuppers themselves make it. The industry is largely informal and unaccredited. The coaches I met for this piece all emphasized that they didn’t need press. They are the ones who come preapproved by the YCombinators and the Andreessen Horowitzes, the tastemakers of the Valley. Such industry legitimacy is as crucial to getting customers as it is to founders raising money: “The wrong kind of coach, without the relevant experience — someone who hasn’t successfully scaled a technology company — can make things much worse,” warns Akkadian’s Bailey.
Two weeks after meeting Maureen Taylor, I head to the Battery, San Francisco’s tony social club, to meet another gold-starred coach. Talking to Bryan Neuberg is like scrolling through the front page of TechCrunch: He drops company and investor names like spare change (Neil Blumenthal, Warby Parker’s CEO, is among them), speeds through shop talk and, weirdly, makes me somewhat anxious to prove myself. This, of course, must be one of his star traits: No CEO would want an easy lay for a coach. Dark-haired, bright-eyed Neuberg, trained in psychology but far from touchy-feely, is sharp and hungry. He fits in at the Battery.
And yet Neuberg began life far from these wood-paneled walls. He is a former radical activist who was once shot (with a nonlethal rifle) in the face at an anti-WTO protest. Today, his firm works on “hard-core management skills,” he says, with young founders like Ethan Bloch. Bloch, CEO and founder of financial services startup Digit, met Neuberg at the Woodstock of the startup age, Summit Series Basecamp. Bloch wasn’t shopping for a coach, but serendipity and chemistry proved compelling. Converging with Neuberg at an insider event provided, Bloch says, an “initial level of social proof.”
Toward the end of my meeting with Neuberg, he social-media stalks me to see who we have in common. “I’m a total yenta,” he quips. “I love connecting everyone.” We are sure to overlap. After a pregnant beat, the LTE beams down the verdict. I return zero shared LinkedIn connections and just one mutual Facebook friend. “You know what this tells me?” he grins, not unkindly. “That you’re not well-connected.”
The industry takes all kinds: There are mindful yogi types and knuckle-rapping practical folks and ones deep in organizational psychology and strategy. There are those with five certificates on their walls and others who draw mostly on individual experience — after all, they are running their own businesses at the moment. Some who will push you and some who will love you and most will promise to do all those things in just the right dosage. There are even the actual shrinks, like Michael Freeman, a psychiatrist at UCSF who also, inevitably, has founded his own company. (I think of the scene in the pilot of HBO’s Silicon Valley in which a stressed founder has a panic attack; the doctor, after treating him, starts pitching his own app.) Freeman studied the connection between entrepreneurs and mental-health conditions. Nearly three quarters of entrepreneurs in his study self-reported mental-health troubles, particularly with depression, ADHD, bipolar illness and substance abuse.
Which adds yet another layer to a seemingly simple story. A quick Googling of “founders depression” reveals blips on blogs like YCombinator’s Sam Altman’s or a short post in TechCrunch: It’s a thing, people get it, you should deal with it. But ultimately, if you want to win, talking about your feelings isn’t seen as the best way. Besides, you’re supposed to dip into your venture funding to build a billion-dollar company, not go to therapy.
There are some in-betweens. The unique Bay Area palimpsest — technology overlaid atop a legacy of mindfulness — has created a “growing acceptance of therapy and spirituality,” even in the workplace, says Stanford business school organizational psychologist Larissa Tiedens. A case study of this warm style is well-regarded coach Khalid Halim, co-founder of Reboot.io. I meet him in his office just a hair away from San Francisco’s Embarcadero waterfront.
Stepping over the threshold to Halim’s turf is like jumping straight into the savasana finale of a yoga class. There’s a small Buddha statue in the corner, and the furniture is all calm gray. Halim sports an impeccably trimmed beard and positively nirvanic smile. A former founder and CEO of his own company — a private-jet food-catering business — Halim, whose M.O. is like a blend of the experienced and the mindful, gets a bit more personal than Neuberg or Taylor. He tells me of some interventions — like the time he says he called up a CEO’s executive assistant to explain that the boss would not be coming back to work that day. The founder didn’t need a strategy reboot or a deep dive or a 360 eval; he just needed a long walk by the water, Halim decided. After that, the next day, he would go back to face the troubles.
But what sticks with me when I leave Halim’s office, a bit sad to reenter the fray of the outside world, is the reason he said he chose to start a softer kind of business, one powered by Zen. It was fatherhood. He says he wanted to be a great dad, an available, calm dad. And this world of coaching, which requires him to sit on the inside and still lets him weigh in with peaceful wisdom from the outside, this was the real entrepreneurial dream: contented success.