How These Founders Learned to Manage Their Depression and Emerge Stronger Because of It

BY 2016, Melissa Bernstein had built a multi­million-dollar company catering to the nostalgia of a gen­­e­r­ation of upscale parents who coveted and ponied up good money for designer old-school toys for their progeny. Over the course of three decades, she and her husband, Doug, had turned their Wilton, Connecticut-based business, Melissa & Doug, into a $550 million empire, the Tiffany of toys. A sunny, ebullient mother of six, she embodied the mythology of the woman who had it all.

Not the commercial success–that was most definitely not a lie. But the façade, her image as the Martha Stewart of playthings, was a meticulously constructed gingham suit of armor, meant to deflect any gaze into how Melissa Bernstein really felt inside: scared, paranoid, and unable to forge meaningful human connections, damaged, depressed, isolated, and alone. “It’s exhausting,” Bernstein says today, recalling sleepwalking through much of her life and career. “I understand now the reason most folks don’t crash until midlife. Because in our teens and 20s, we shoulder it, right? We can bear the façade. We can pretend we’re someone we’re not, and we get through it. But as I started to get older, I started to hear–it was literally like a drumbeat: ‘You aren’t being true to yourself.’ “

Bernstein had spent her life honing the art of being perfect, and perfect is a full-time job. She was proud to tell people she’d never missed a day of work, even while birthing six kids. Every day, it was up at 6, four different trips getting the kids to various schools, off to the office, a full day of work and calls and emails, home to make dinner, more kid duty, more work, and then a collapse into bed at midnight. She wore her stoicism as a badge of honor, would breezily tell a team member who was getting upset, “It’s just toys,” even as inside she questioned herself constantly, scolding herself that “you cannot afford to be less than perfect.” She led by faux example.

“She’s got a twinkle in her eye, and she makes magic happen,” says Christine Osborne, a recently retired operator of upscale toy stores in South Carolina and a longtime Melissa & Doug customer. “You would never know she suffered from depression. She hid it very, very well. I have a psych background and didn’t pick up on it.”

As Bernstein says: “I believed in being this robotic superwoman who could do it all.” Deep down, she was terrified. Of showing weakness. Of being found out. Of succumbing to the sadness that coated her insides like varnish. She felt the lie beginning to crack.

“It’s the voice of our soul that really is telling us who we are,” she says, “and crying to be seen authentically. I had denied that voice my entire life, because anytime I tried to show who I truly was–which was an introverted, heady, repressed, very deep, intense creative–people looked at me like I was weird, and I didn’t want to be weird. I wanted to be popular and affable and have throngs of people attracted to me. So I knew that I would never be accepted as I truly was. My whole life was this gap between who I was and who I was trying to be.”

But it wasn’t the voice of her soul that she was listening to. Another, far darker voice had her ear. The one that spoke to her when she was alone, looking up at the ceiling in bed late at night, or standing in the shower, or lingering in the foyer of her house after her kids had left for school. End your life now, it said. It’s all futile.

THEY ARE THE rock stars of the busi­ness world–the moguls, entrepreneurs, startup whiz kids, celebrities with social media platforms bursting with eager followers who swashbuckle into the marketplace and declare, “I am going to bring the Next Big Thing.” The image of the brash founder and CEO “thinking out­side of the box” and “taking no prisoners” harks back to a certain Silicon Valley archetype. In public, in interviews on CNBC, and in profiles in glossy magazines, they telegraph a breezy but steely confidence that says to the general public–and, more important, to potential investors–“I’ve got it all figured out.” Think back to when Mark Zuckerberg first arrived on the scene. Or Jack Dorsey. Or Elizabeth Holmes or Elon Musk. As time has often proved, rarely is what we think we see what really exists.

To the world, he was CEO of a sexy tech company; in reality, he had devolved into a feckless people-pleaser, directionless, lost, and horribly depressed about it all.

Never is this truer than in the inter­section of mental health and corporate founders–entrepreneurs conditioned to forge ahead with a belief, virtue-signaled by a uniquely American ethos, that showing weakness or vulnerability is death to the dream. Customers and shareholders want powerful, decisive, confident leaders, full stop. So it is that generations of business leaders have hidden within themselves, projecting an image of John D. Rockefeller grit while simultaneously pushing down waves of doubt, depres­sion, and anxiety roiling within.

“Faking is very, very tough on people. I mean, it’s physically tough,” says Acacia Parks, chief science officer at Happify, the popular personal growth app–and herself someone who lives with bipolar disorder. “The whole time you’re faking it, it requires extra physical strain on the body. And it’s distracting. If you are working and being creative, you’re so busy being fake it’s extremely draining, and both physically and mentally deleterious.”

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HE KNEW SOMETHING was off. Way off.

He wasn’t sleeping. He had constant back pain. His marriage was fraying–his wife had recently declared, “I can’t hear about your work. When you come home, we don’t talk about it. We’re done.” He found that he was increasingly negative, short-tempered, indecisive. He took the blame for anything and everything, mistakenly believing this would show him to be a humane, empathetic leader, when all it did was convince his team that he was in way over his head. He was hiring and firing the wrong people; as his leadership waffled, morale plummeted. To the world, he was the founder and CEO of a sexy tech company; in reality, he had devolved into a feckless people-pleaser, directionless and lost, and, secretly, horribly depressed about it all. At night, he began zoning out to children’s cartoons.

He was, Rand Fishkin says today, “running up the down escalator.”

It certainly hadn’t started that way. Fishkin had been your standard-issue tech wunderkind, laying the groundwork for his web marketing company, Moz, as a young man in his family house outside of Seattle. Your typical ’90s American middle-class geek, he dropped out of the University of Washington two classes shy of a degree and was working at a men’s clothier when he began designing websites for clients of his mom’s boutique marketing consultancy. Eventually, he was building sites full time, and blogging about it. He recruited a friend; they began developing software. VC interest followed. In 2004, Moz was born.

But, unlike the more high-profile poster boys of the aughts’ pullulating tech orbit, swaggering their way through conferences and cable television appearances in their T-shirts and hoodies, as the years passed Fishkin found himself struggling with the burden of leading a company, and internalized it. “I didn’t have the strength of will and competence and confidence in myself, or my leadership abilities, to make the difficult calls that one should make to recognize when things weren’t going well,” he says today. “How they should be changed, and managed.”

Depression quickly set in for Fishkin, which only made things worse. How can you be the CEO and allow that kind of weakness to show? “Rand is a luminous person,” says his wife, the noted travel writer Geraldine DeRuiter. “He has this vibrancy about him, this kind of sparkling joy. It dims when he is depressed. He becomes withdrawn, and blames himself for everything that goes wrong.”

After a while, it was clear something had to happen. And so, in 2014, Fishkin stepped down as CEO, advocating for his COO to take over, which she did. (He cheekily took the emeritus-like title Wizard of Moz.) He felt that removing himself from the day-to-day strife of responsibility and decision-making would cure his illness. Instead, he watched helplessly as the company he’d built foundered, as the darkness inside engulfed him. “I struggled even more,” he says, “with that same anxiety and depression and frustration.”

As the next few years passed, Fishkin watched, in his new emeritus role, depressed and powerless, as the decision-making was, in his view, “taking us further off the rails.” Moz’s growth rate, which had been 50 percent annually when he stepped down, plunged to 20 percent, then to 10, and then to below 5. There were layoffs, and little innovation in product or engineering. Sitting and stewing at yet another endless meeting at which he had no decision-making power, Fishkin says he pulled out his phone and texted the CTO, Anthony Skinner, now sitting directly across the board table from him.

WHAT DID I DO? Fishkin texted Skinner, now ruing his decision to step down at all.

YEAH, MAN, came Skinner’s reply. YOU FUCKED UP BIG TIME.

Rand Fishkin excused himself, walked into the men’s room, and threw up.

THE STAKES ARE HIGH and the impacts broad. Consider the following list: Ilya Zhitomirskiy, co-founder of Facebook competitor Diaspora; Don Cornelius, founder and creator of Soul Train; Aaron Swartz, co-founder of Reddit; Jody Sherman, co-founder of Ecomom; Matt Berman, founder of Bolt Barbers; Austen Heinz, founder and CEO of Cambrian Genomics; Faigy Mayer, CEO of Appton; fashion designer Kate Spade. All were fabulously successful entrepreneurs. All battled mental illness and depression. All of them took their own lives within the past decade.

Recent studies put the number of entrepreneurs with some form of mental health issue at 49 percent. Almost a third report experiencing depression.

“Founders have a higher disposition to depressive episodes,” says Lisa Andresen, a San Francisco-based therapist who has studied entrepreneurial depression extensively. Part of this, she says, is the mere fact of who they are–the ones dealing with a company’s highest pain points, the revenue shortfalls, the pressure from investors for more aggressive returns–which in turn boomerangs into their personal lives and results in higher rates of divorce and social isolation. Andresen says narcissistic parents who have fostered perfectionism are also common among founders: “You grow up being the family trophy. You earn love by achieving. And you have a balance sheet of millions of dollars, and your parents are still giving you shit. So you’re never happy.”

A midlevel executive dealing with depression may be able to cover their illness. But the titular head of a company has nowhere to hide. Eventually, the depression wins as its standard effects–low energy, difficulty focusing, unproductivity, indecisiveness, and unresponsiveness–begin to leak out. “Of course it’s noticed,” Andresen says. “Employees personalize it. They think their boss hates them, or they’re about to be fired. So it can create paranoia.” The boss has become a time bomb sitting in plain sight, ticking away in the corner office.

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JELANI MEMORY WAS the kid in high school so many of us wished we were. Smart. Good-looking. Insanely popular. When he walked down the corridor it was as if the sea was parting. Being one of the few minority students in a predominantly white high school might have made him feel like an outsider. Instead, his magnetism made him the friend everyone wanted to have. He lettered in multiple sports, was the special guest star at every party.

All of us can look back at high school and instantly name the kid we wished we’d been, the one who seemed to glide through the whole thing effortlessly, without awkwardness, self-doubt, acne, or empty weekends. For those who went to school at Woodrow Wilson High in Portland, Oregon, with Jelani Memory, he was that kid.

And yet it was then, during that very period–years before he founded A Kids Company About, a nimble publishing startup dedicated to gently but frankly telling children the exact sorts of things he desperately wished someone had told him–that Jelani Memory realized he wasn’t actually that kid at all.

He wanted to sleep all the time. He spent the nights tossing and turning, the days sluggish and foggy. He adopted a wan veneer of winsome conviviality that allowed anyone to see what they wanted, the Big Man on Campus, while behind it he was running on empty. “To say it was impeding my life is an understatement,” Memory says. “Feeling sad all the time, feeling unfulfilled, unsatisfied, when I knew that things in the external parts of my life should be things that are fulfilling, that are wonderful, that should make me happy, that should offer me validation. And yet still feeling incredibly lost and alone.”

And hiding it from everybody. “Most of it he paved over, for sure,” says Sean Tittle, an architectural designer and one of Jelani’s closest friends since the age of 6. “You love this person next to you, but you can help only if they reach out. It’s hard when you’re holding those secrets inside and projecting that happy face.”

Some epiphanies come as thunderbolts, jolting us out of our stupor and opening a path in a new direction. For young Jelani, it was more a case of clouds slowly parting. All of these things, I should be happy, I should like life, I should be enjoying this, he thought. But I’m not. And so, at the age of 17, he looked at himself in the mirror and made a decision that would change his life. “This isn’t working,” he told himself. “I’ve got to find another answer.”

AS TOLSTOY MIGHT have written, all unhappy founders are unhappy in their own way. But if Bernstein, Fishkin, and Memory share one thing in common, it’s the path each took out of their respective journeys, all built on three simple actions: admitting they needed help, getting it, and refusing to lie about any of it anymore.

Soon after throwing up in the men’s room, Fishkin left Moz. “That was a fucking lonely, bad day,” he says. “It was this company where I built all of my everything. It was me and my mom, and we started this thing and now … to feel like your company is, not being taken from me, but that I messed up and handed it off foolishly, and then lost the power to con­trol its destiny. I felt like I let a lot of people down.”

To pick them back up, he had no choice–he first had to lift up himself. In 2018, Fishkin started SparkToro, which he calls “an influencer and audience intelligence” marketing company. He penned a memoir, Lost and Founder: A Painfully Honest Field Guide to the Startup World, and after sharing his struggles with depression and anxiety, hundreds of people wrote him, thanking him for his honesty, for advice he’d given, for past kindnesses he couldn’t even recall extending. For being human. “I would be at my desk just crying in the middle of the day,” he says, “because these stories were incredible.”

Bernstein’s savior came via a tome written more than 70 years earlier. A Holocaust survivor, Viktor E. Frankl, had published Man’s Search for Meaning in 1946; the book is now considered part of the 20th-century canon about the meaning of life. Frankl’s painful exploration of the unique existential despair experienced by highly creative people pulled Bernstein back from the brink by giving her a name for what she was experiencing.

“I started to say, ‘Wait a second, all these qualities that I have been trying to expunge and kill my whole life,’ ” she says, ” ‘are actually my meaning. They’re the reason I’m here.’ “

For years, the voice in her head had told her, “Nothing you do will ever matter. You will always be alone. No one will ever understand you or truly accept you.” Now, walking with her husband, Doug, on the beach near their vacation home in the Bahamas, she turned to him and said, “I’m not alone.”

His reaction helped jump-start her recovery. “OK, I don’t hear the bad part about this,” he said. “This is not something you have to hide, or have shame about.”

The head of a company has nowhere to hide. Eventually the depression wins. The boss has become a time bomb, ticking away in the corner office.

She got a therapist and began to self-identify as an existential nihilist, leading her on a path where she read Kierkegaard, Sartre, and “literally every piece of existential philosophy, ever,” she says. And, most important, she got real with everyone–her kids, her business partners, her employees. She persuaded personal development guru Jonathan Fields to have her on as a guest on his popular podcast, Good Life Project. “I knew it was really risky, because I create the lightest and brightest thing, and I’m about to tell people that I suffer from the darkest form of despair. Are people going to be like, ‘I can’t give this to my child–this woman wanted to end her life’? I definitely felt that,” Bernstein says. “But there comes a point when you have a greater purpose.”

That purpose now includes a new venture called LifeLines, a lifestyle website and book that share her journey and lessons for happiness and self-acceptance. The reaction to her disclosure was, in her words, “shockingly, incredibly good.” As Fishkin experienced, letters and emails poured in. She is now surrounded by people with whom she shares deep connections. “The very thing I thought would prevent me from having these close relationships,” she says, “was the thing I needed to develop them.”

As for Memory, he found his recovery young, in college. There he majored in Bible and theology and found a path to wellness through faith and an unflinching look at episodes of his own childhood trauma, which he says included neglect and violence among his siblings. It was time to heal.

“I would later learn how to actually cry,” he says. “That started even a further journey of being able to really feel safe and secure diving into some of this, the scariest part of my internal life, going, ‘Gosh, I’ve actually been sad for a long time.’ “

It also started his career path, which poured gasoline into his recovery by sending him on a mission to help other kids whose depression might be going undiagnosed or ignored. Inspired by the work of Fred Rogers and LeVar Burton, in 2018 Memory founded a company to build storytelling for children, producing books around life’s most difficult topics: A Kids Book About Racism, A Kids Book About Anxiety, A Kids Book About Suicide …. “Jelani’s very candid and honest about how he’s doing and his experiences, which is great because it makes me feel like he’s more human,” says Kenya Feldes, the studio manager at A Kids Company About and someone who has also battled depression. “I’m not the only one who may be going through it.”

“I walked around with this thing I didn’t even know how to describe, and I never, ever talked about,” Memory says. “I think that most grownups believe that children are mostly innocent and mostly happy. With enough video games, school, and sugar, they’ll be OK, right? Just keep them away from ‘the bad stuff.’ I think the reality is a lot more complicated. Many kids are struggling just to navigate everyday life. So for me, it’s that ability to look at every kid and go, ‘There’s something underneath that they wish somebody knew about, that they wish they could talk to somebody about.’ I think my experience dealing with depression at a very young age is the ability to recognize and honor that.”

THERE IS, TO be sure, a generational shift afoot around mental health in the workplace, specifically around transparency of leadership. Millennials and Generation Z now make up roughly half of the U.S. workforce, and by every measure of surveys and research it is clear they expect a different kind of leader, one who leads by example and exhibits strong mental health. A CEO can no longer tell workers the company values “balance” as it pours on work to be completed on nights and weekends, zinging endless Slack messages throughout.

“I think the acceptance now of the vulnerable, the honest, the not-all-knowing CEO, who’s patient, who’s humble … it marks a sea change.”

“They aren’t just interested in some general wellness plan or ‘well-being,’ ” Happify’s Parks says of today’s talent pool. “They’ve been through this pandemic, they’re vulnerable, and over 50 percent suffer from depression. They’re not messing around about their mental health. One of the overwhelming narratives among these folks is that they need to see their leaders actually taking care of themselves, confidently modeling being human. That’s new.”

It also suggests a new path for founders who are coping with depression.

Casey Henry is co-founder and CTO of SparkToro, Fishkin’s new company. He’s worked for several startups, including Moz, and knows well the pressure that can come, as he says, “when you’re a company that wants vigorous growth, and you have VC backing, and investors who want a return. We’ve all worked those 60-hour weeks.”

His boss has an answer for that: Just don’t do it in the first place. To launch SparkToro, Fishkin has eschewed VC funding for angel investors who are more patient, more nurturing, and less focused on short-term returns. Finally feeling mentally healthy and whole, he is leaving the VC world behind. “I don’t want to get on that roller coaster again,” he says. “It’s not for me.”

There is reason to believe that he’s not alone. “Investors are people too,” says Andresen, who suggests that capital is increasingly placing a premium on emotional intelligence when looking for leaders. “They’ve had their own mental health experiences, and see it in their own families. They develop relationships with their founders, and the relationships transcend the business transaction. There’s movement there.”

And, perhaps, a reason for optimism. “I think the acceptance now of the vulnerable, the honest, the not-all-knowing CEO, the CEO who’s patient, who’s humble, who’s thoughtful, who doesn’t have the answer to every question, who isn’t ‘take-no-prisoners’ or the person who will destroy you in the boardroom, I think really marks a sea change,” Memory says. “These kinds of leaders have always existed. But they’ve never truly been as valued as they can be.”

From the Winter 2021/2022 issue of Inc. Magazine

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