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The Humbling of Andy Dunn: How the Bonobos Co-Founder’s Struggles With Mental Health Almost Upended Him–and His Company

The Humbling of Andy Dunn: How the Bonobos Co-Founder’s Struggles With Mental Health Almost Upended Him–and His Company

ANDY DUNN WAS RIDING HIGH. It was 2012, and he was running a hot e-commerce fashion company he’d co-founded. He’d cashed out seven figures’ worth of shares on the secondary market and was living like he thought a CEO in his early 30s in New York City should be living: large. He bought a black Porsche. He jetted off for weekends in Istanbul and Moscow, and ran up a $10,000 Four Seasons bill in Bali. He went out to clubs and restaurants almost every night: drinks with a potential hire at 6; a dinner date at 8; meeting a friend for more drinks at 10.

His company, Bonobos, had launched in 2007 and pioneered an online-first, brand-building model that just a few years later was being copied by entrepreneurs in every consumer-product category imaginable: direct-to- consumer eyeglasses, shoes, razors, dog food, luggage, undies, and more. Dunn started to see himself as a kind of godfather of a new consumer movement. He hired bright college grads to run customer service in-house in one of the world’s most expensive cities. He opened brick-and-mortar showrooms, dubbed Guideshops, at a time when legacy stores were flailing. Bonobos was early to social media marketing and omnichannel retail, and it helped usher in a whole new startup econ­omy in New York.

Dunn convinced himself that Bonobos, which began as a brand of better-fitting men’s pants, could become the technology backbone of modern commerce–Shopify before Shopify filled the space. Dunn himself began to spread his influence on a web of companies he invested in (Warby Parker, Harry’s, Oscar, Coinbase) through a venture capital firm, Red Swan, that he’d co-founded in 2011. And he figured Bonobos should start creating its own sub-brands; the first two, Maide and AYR (for golfers and women, respectively), launched in 2013 and 2014.

There were a few problems with this plan: For one, the company was bleeding money. By 2013, Bonobos had raised $75 million in venture investment and was burning as much as $5 million per month. That summer, it needed to find another $50 million to keep operating–let alone to turn into a software giant or a retail holding company.

And Bonobos was bleeding talent, especially top executives. Dunn was a mercurial boss. He had undermined and pushed out his co-founder, Stanford business school classmate Brian Spaly, who had dreamed up the idea for Bonobos and designed the pants that started the whole party–and whom Dunn now blamed when things didn’t go as he hoped. He’d hired another old Stanford pal, Bryan Wolff, to be his CFO, but then fired him over an opulent steak dinner after disagreeing with his efforts to establish some fiscal discipline. The head of engineering, the head of marketing, the head creative: revolving doors all.

But Dunn was the CEO of a high-profile, press-darling company. He wrote thought-leader articles for Medium on the future of e-commerce. He spoke at an event in Las Vegas with Zappos founder Tony Hsieh, one of his heroes. There were battles, and sometimes collateral damage–but, hey, that’s startup life. Andy Dunn had arrived.

DUNN DIDN’T KNOW WHERE he was. He awoke in a hospital bed in the psychiatric ER at Manhattan’s Belle­vue Hospital, in a room with three other patients experiencing acute mental health crises. His hands were tied. He managed to struggle free, climb out of bed, strip naked, and lie down on the floor, where he screamed for help.

He’d learn, over a week in the psych ward and then en route to a police station and eventually jail, that he’d spun out of control over the course of a weeklong manic episode, and that he was being charged with two counts of assault–one a misdemeanor against his girlfriend, Manuela Zoninsein, and the other a felony against her mother, a senior citizen.

It was early 2016. As he pieced events together and people filled him in, a blur of images began to emerge from the preceding week–work dinners and birthday parties, a gospel choir and a Broadway show, getting lost in Brooklyn and imagining he was Batman or maybe the Messiah–culminating in a sleepless night spent howling like a wolf and then reeling out of bed, slamming his head into a door frame and punching a window, and finding blood streaming down his face and hand. And then … what? Zoninsein had been trying to calm him and had called her mother that night to come over and help, but Dunn’s mental images were still dark, he says, about what happened next. Zoninsein told him he’d struck her in the face and pushed her mother to the ground and kicked her while she was down.

“How much do we excuse because of bipolar disorder versus how much does one simply need to be held accountable for?”–Brian Spaly, Bonobos co-founder

Nothing would ever be the same. He had known, since a manic episode and diagnosis in college some 16 years earlier, that he had bipolar disorder type I, which the National Institute of Mental Health describes as “defined by manic episodes that last at least seven days, or by manic symptoms that are so severe that the person needs immediate hospital care. Usually, depressive episodes occur as well, typically lasting at least two weeks.” Dunn had long resisted the label, even though a few lesser manic episodes had been enough to put some of the people who knew him best, such as his sister, on high alert. Now, after an episode that had turned violent, the reality of his mental health was unavoidable.

In some ways, Dunn was lucky. Lucky he didn’t hurt anyone worse than he did. Both women were physically bruised, and emotionally much more so. He was lucky that he got out of jail after just 12 hours because he’d agreed to show up for a hearing a week later. Less privileged people might stay locked up. He was lucky that the judge eventually dismissed the charges after six months of observation. And he was lucky that he had compassionate, understanding people in his life who would work with him to build a path forward–including Manuela and her mom. Less fortunate people might not have a supportive family or a company counting on its boss.

By now we are all too familiar with some of the grim statistics regarding the links between mental health struggles and entrepreneurship. A study by psychiatrist Michael Freeman of the University of California San Francisco found that almost half of entrepreneurs deal with mental health issues, compared with 32 percent of non-entrepreneurs. The same study found that bipolar disorder affects 11 percent of entrepreneurs compared with just 1 percent of non-entrepreneurs, and depression, 30 percent versus 15 percent.

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According to Freeman, the link between entrepreneurship and mental health goes both ways: Bipolar people are drawn to entrepreneurship, but entrepreneurship is itself a kind of bipolar pursuit, where high highs can be followed by equally low lows–making money, running out of money; hitting on a great idea, watching it fail; pulling all-nighters, not being able to get out of bed. “It takes a certain type to be drawn to that,” Freeman says.

What’s more, venture capital-backed, fast-growth entrepreneurship is a particularly fertile breeding ground for unhealthy work practices. Young bosses like Dunn, people who have scarcely held a real job before, find themselves armed with sometimes hundreds of millions of dollars and teams of mostly unencumbered young people who can erase the work-life boundary in pursuit of grandiose goals to change the world or flame out trying–even if what they’re really doing is, for instance, selling pants.

It’s a system that encourages exorbitant spending and tolerates reckless behavior or callous treatment of others in pursuit of growth at all costs–and can leave considerable wreckage in its path. For Dunn, that reality combined with his mental health volatility meant he was speeding through an obstacle course with faulty steering and no brakes–and he started colliding with things, until his manic episode in New York led to the crash that stopped him cold.

Today Dunn sits in a darkened bedroom in Chicago, his hometown and where he lives once again, and reflects on his journey since the assault and how it’s changed him. His memoir, Burn Rate, publishing in May, explores the events that led to that terrible night–the roller-coaster ride of Bonobos, the ruined relationships, the soaring highs and crushing lows–and unflinchingly describes the terror he inflicted on the people closest to him. But the five years since then are largely absent from the book, and they include perhaps the most important set of lessons for entrepreneurs working through their own demons. Dunn has a lot to say–not just about how he fell apart, but about how he has worked to put himself back together.

Through it all, he’s attempted to repair himself and his relationships while still moving forward with his career. “My spike was so high and then it came right back down. But it was so through-the-moon, savior-of-the-world high that the amount of low time that I had to pay back almost like credit card debt was just months and months of catatonic depression,” he recalls. “I was taking a lot of medication. And as that was happening, I was trying to figure out how to make sure Bonobos stayed afloat and how”–or rather if–“things could persevere with Manuela.”

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AN ENTREPRENEUR HERSELF, WHO IN 2020 FOUNDED a reusable-water-bottle vending system called Kadeya after stints at two agtech companies, in Beijing and São Paulo, Manuela Zoninsein had met Dunn in New York in his jet-setting phase. She knew he was consumed with work and partying back then, and it took four years between their first and second dates, but something about their both being ­ambitious and independent–even if they had very different styles–had drawn them to each other.

A few days after the assault in 2016, Zoninsein visited Dunn briefly at Bellevue, which he took as a sign of hope that he could cling to in his recovery–and a source of shame, since she had a black eye she’d tried to hide with makeup. She talked to her mom, who advised her that, although Dunn’s bipolar disorder was incurable, if he were taking meds and seeing his therapist regularly, he could manage his mental health and Manuela would be safe. “But if he’s not seeing a doctor and not taking his meds, I would never let you marry him,” she said.

Zoninsein decided to try to forgive Dunn. “Obviously, I loved him, and I still love him,” she says now, claiming that Dunn had never before hurt her or had a violent outburst. “I wanted to see the good.”

So began a slow process of healing and rebuilding trust. Dunn and Zoninsein began to see each other, but only with a chaperone present. The first night they slept in the same room together again, his mother was there as well. But gradually, as Dunn demonstrated that he would not divert from his new care regimen, they added more independence. The first night they were home together alone, multiple family members were on standby in case of emergency.

Dunn had a new psychiatrist, who put him on a daily mood stabilizer, began talking with him three times per week (a cadence that continues today), and stood ready to intervene with other drugs if Dunn ever appeared to be spiraling in one direction or the other. Dunn’s mom put him on a rigorous sleep schedule, because his tendency to put in long days, or even all-nighters, had dovetailed with his worst habits. ­Research has shown a clear link between sleep disturbance and the severity of bipolar episodes. Dunn started wearing a Fitbit and sharing a daily sleep report with his family. (Today, if he has multiple nights with fewer than six hours of sleep, someone conducts an intervention and makes sure he gets a good night’s rest, while his psychiatrist adds a new pill.)

Dunn also cut back on alcohol–though he decided not to quit drinking outright, thinking that extremes of any kind could be triggering for him. “Because,” he says, “what happens if I come back and really miss it? It might be healthier for me to drink once in a while than to abstain and then go nuts.” It’s a convenient conclusion for an enthusiastic drinker, to be sure, but it comes with a commitment not to drink on some of the most celebratory occasions–what he considers “peak experiences,” such as the night of his eventual wedding to Zoninsein in 2017–because all that mental stimulus could lead to mania, so why complicate matters with booze?

“I never want Manuela to go through what she went through,” Dunn says now. “I never want to hit her again. I will go through anything to not have that possibility happen.”

In some ways, one of the most difficult steps for Dunn was learning to tell others about his disorder. Today he informs friends and associates almost immediately, but he first had to cross that Rubicon at work. During his hospitalization, he’d simply vanished from the office. People were used to his impulsiveness and frequent absences, but something was clearly different this time. He decided to tell his board of directors before letting the whole company know, so after he’d filled in a few key execs the day he returned, he steeled himself for a call with the board the next day–and then blurted everything out as soon as everyone was on the line.

“I just spent the last week in the hospital,” he began. “I had an episode, what they called a manic episode, during which I lost my mind. Before getting to the hospital, I struck both Manuela and her mom. When I got out of the hospital, I walked straight into handcuffs.”

The directors had questions, but to Dunn’s surprise, his news was met with concern and support, not anger or dis­appointment. Dunn turned the conversation to sharing his crisis-management strategy: his new regimen with his psychiatrist; his lawyer, who believed that the case would be dismissed as a mental health issue rather than seen as a criminal one; and the heavy-hitter PR firm he’d enlisted, in case the gossip pages somehow got hold of his story.

By the end of the call, the consensus was that they stood a good chance of preventing the CEO’s personal issues from damaging the company. And Dunn still had a job. But Bonobos had other problems.

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IN THE MONTHS BEFORE HIS MANIC EPISODE, DUNN HAD come to the tough conclusion that he needed to sell the company–and his old partner, Brian Spaly, had indirectly helped him reach that epiphany. Spaly had launched a new startup, a subscription fashion service called Trunk Club, after he’d gotten pushed out of Bonobos. Five years later, he sold Trunk Club to department store chain Nordstrom for $350 million, having raised about $12 million in venture capital. Bonobos had now been in business twice as long, wasn’t much bigger than Trunk Club, and had needed 10 times as much investment ($127 million, to be exact) to get there. “By capitalism’s scoreboard, [Spaly] had put up a big win,” Dunn writes in Burn Rate. “Bonobos’s fate, on the other hand, was uncertain.” The company’s investors saw all of this, and the early ones especially were starting to get impatient. They wanted a return sooner rather than later.

After exploring multiple exit options, Dunn lined up a private equity deal that seemed like it would protect the company more than most such deals–but then he reconnected with an old acquaintance, Marc Lore, an entrepreneur who months earlier had sold his most recent startup,, to Walmart. Lore, who’d sold a previous startup, Quidsi, to Amazon, explained to Dunn that Walmart planned to take on Amazon in an aggressive battle for ­e-commerce supremacy, and that he was leading the charge as Walmart’s head of e-commerce. As part of his war strategy, he envisioned building a portfolio of digitally native brands that could ­offer consumers some exclusive products that Amazon wouldn’t have. Would Andy join forces with him and run that group–and bring Bonobos along as a key piece of the puzzle?

Dunn agreed to sell the company for $310 million and found himself genuinely excited to get to work on something as big as attacking Amazon. It also got him out of a tight spot at Bonobos, where the rising cost of digital marketing was revealing that the business model had challenges–like not turning a profit. Operating Bonobos under the Walmart umbrella could theo­retically give it some protection from those market forces, and certainly unlock efficiencies.

He showed up at Walmart headquarters in Bentonville, Arkansas, fired up to make change. Bonobos would stay in New York, and he would remain its CEO, but he rented a cottage behind a Bentonville B&B and started spending most of his time there, or in Hoboken, New Jersey, where Lore was overseeing digital.

“He came in with bright eyes, like, ‘I’ve got this, we’re gonna build this big digitally native portfolio, go, go, go, do it,”” Lore recalls. Then he ran into reality. “He learned eventually, no, no, you have to bring everybody along. You can’t just go–this is a big company. You need to build out a strategy or plan, present it, get buy-in.” Whereas Dunn thought, naively, that he’d be operating in a kind of entrepreneurial silo, where Bonobos and his other projects could benefit from Walmart while keeping it at arm’s length, the reality was quite different. Most notably, his projects weren’t getting greenlighted. To everyone else, Bonobos was a business division that was underperforming. It was actually losing money, in a company that is notorious for inventing aggressive new means of penny pinching.

Dunn’s team started becoming frustrated, and leaving, because even though their boss had promised them freedom, core functions such as HR and finance needed to mesh with Walmart’s way of doing things–which created a confusing chain of command and actually made his co-workers feel more undermined than empowered. Dunn himself was suddenly one of 200 or so people at his level in the company. “It was like having influence without authority,” he says now. “I found it so maddening not to have the final say”–especially since handing over leadership of Bonobos to one of its executives, Micky Onvural, a year after the acquisition, so he could focus on spinning up new brands.

Lore remembers, too, seeing various Walmart corporate employees scratching their heads at Dunn’s behavior. During one big meeting, Dunn, who’d converted to Judaism in 2017, was asked onstage, ” If you had a chance to go back in history and ask one question of one individual, what would it be?” Dunn’s response in front of a thousand Walmart associates: “I would ask Jesus, are you God?””He got killed for that,” recalls Lore. “That’s kind of Andy in a nutshell. It’s a great response! But maybe not the right audience or timing.”

One night over drinks in Bentonville, a co-worker pulled Dunn aside to give him a tip. “You know, Andy, everyone is not your friend,” she said. “And they weren’t always your friend before, either. It’s just that you were the CEO.”

It was a light-bulb moment for Dunn, who’d never really had to play politics. Back in New York, his friend Alexa von Tobel, who’d sold her startup, LearnVest, to Northwestern Mutual, told him how he could start winning people over. “You’ve got to get really small,” she said. “Being an entrepreneur is all about being big. You’re out there trying to get attention. You’re big with your team, you’re big with investors, you’re big with media. But inside a big company, it’s about putting your head down and doing your job. And in particular, because you’re coming in with this public persona, where people have seen the sticker price of the acquisition, they’re looking at you assuming that’s where a lot of their hard-earned profits have gone.”

“I want to do a big one,” Dunn says with a bit of his old swagger. “I want to run a big company at scale. I want to work on something for 15 years that is globally important.”

Over time, Dunn picked up on some of the humbler traits he saw in other Walmart executives. CEO Doug McMillon became a kind of role model. Dunn noticed, for instance, that McMillon tended to stay silent for the first 45 minutes of meetings. Dunn had always assumed that leaders lead by talking, by selling their vision. But McMillon led by listening and asking questions so he could make better decisions. Convincing people had nothing to do with it.

Dunn began to take that approach at home. Zoninsein, who considers herself an introvert, recalls how their conversation pattern began to shift, especially if something was in dispute. “I generally choose my words pretty carefully, and for a long time, Andy and I had a dynamic where he would talk over me and kind of CEO the situation. I would say to him, ‘Hey, it takes me a little while to articulate what I’m thinking or feeling. Can you give me the space to figure it out?’ So he’d been hearing that already from me for a couple of years, and by the time he started seeing it from the CEO of the world’s largest company, it stuck.”

As Dunn absorbed the culture of Walmart, he started to feel at home there and, before it became clear the company was going to edge away from the strategy that had brought him in, he wondered if he’d find a long-term future there–maybe as the head of marketing, he imagined. He even asked Zoninsein, by then his wife, if they should move to Bentonville. She was clear and direct with her answer: “No.”

She had her own company and career to build, and it was not in Arkansas.

IF THERE’S A HIDDEN UPSIDE TO HAVING A MAJOR psychiatric issue, Dunn has found, it’s that it creates an occasion to reexamine your whole life, to make amends for all manner of missteps and ruined relationships that may or may not be directly related to your mental health. Dunn has spent a lot of time in the years since that night in 2016 working to mend his family and business relationships. But there’s one relationship that may never fully heal: the one with Brian Spaly, the old B-school buddy who dreamed up Bonobos, hired Dunn as his CEO, and then found himself ousted.

Spaly had sold most of his Bonobos shares years before the Walmart acquisition, and Dunn had hoped the cash would do a little to salve the wounded friendship–but, realistically, it probably did more to assuage a little of Dunn’s guilt. The two remained on cordial enough terms that Dunn visited the Trunk Club headquarters in Chicago once before Spaly sold to Nordstrom, and the experience haunted Dunn. As he writes in Burn Rate, “The energy there [was] kinetic. It was one of the most humbling moments of my life–seeing the culture there.”

Today both men say they’re friends and get together once or twice a year for a meal. But both also carry the weight of their tumultuous past. Dunn thinks back often to how things soured between them and has concluded that he was projecting his own deficiencies as a manager on his partner. And he credits Spaly not only for birthing Bonobos, but also for creating the opportunity for him to be its CEO. “If Spaly doesn’t invent the pants, there’s no Bonobos,” he says. “So he was the conduit for me to do that job. And then I kicked him out. I kicked him out of his own thing. I would say that Brian still holds power over me, like I’m indebted in some way.”

In the fall of 2016, the Chicago Cubs were finally, after 108 years of waiting, on their way to winning the World Series, and Dunn saw an opportunity. It was a few months into Dunn’s rebound from the manic episode, and he felt a need for resolution. He sent Spaly tickets to a game. In some ways, he admits, Burn Rate is something of a public apology to Spaly–and to Zoninsein and others he harmed.

Spaly, for his part, says he wants to forgive–and appreciates gestures such as the Series tickets. But the reverberations of Dunn’s behavior more than a decade ago still affect him, and he says he doesn’t plan to read Burn Rate. He meets me for coffee one morning in Austin, where he lives and works as a venture capital investor with a portfolio of DTC brands that are, in essence, direct descendants of Bonobos.

After being pushed out of his own startup, Spaly says, he retreated to the Midwest with his tail between his legs. He managed to turn his bitterness into motivation to start Trunk Club as a different kind of company, with a healthier, happier culture. Still, he wonders what might have happened had he and Dunn hashed out their differences, or acknowledged Dunn’s mental health issue and dealt with it. “In hindsight, realizing that he has a bipolar disorder, I wasn’t well positioned to manage that,” he says. “And, well, gosh, I sure wish I’d known, and he’d realized, and he’d gotten out of the way and let me build this business.”

In the next breath, though, Spaly gives Dunn credit for his whole career. “I was much more risk-averse in business school, and he was the one who said, ‘Let’s go, let’s do this thing.’ I owe much of my life fulfillment to Andy Dunn. Andy encouraged me to be an entrepreneur and take risks and be OK with the possibility of failing. And, frankly, he thought my idea was amazing.” He pauses a moment. “I probably benefited from his bipolarism, because when he was up, he was infectious.”

The more Spaly talks, the more his feelings twist around on themselves. “I give Andy a lot of credit for helping me be the better parts of myself, and I want to honor that by not turning away during his healing process,” he says. But, then again, “How much do we excuse because of something like bipolar disorder, versus how much does one simply need to be held accountable for? Because we all have our tendencies that can get us into trouble.”

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INDEED, THE LINE BETWEEN MENTAL HEALTH AND behavioral variations is hard to define. We all have highs and lows, spells of intense positivity and negativity, moments of kindness and cruelty, beneficence and selfishness. And studies have shown that some of those extremes are closely associated with entrepreneurial success.

To be sure, mental health professionals hold that the ­extremes of bipolar disorder are so much more pronounced and prolonged that it’s inappropriate to consider the condition on the same spectrum as regular highs and lows. But that doesn’t mean everything a person who suffers from bipolar disorder does is attributable to it. A judge ultimately dismissed Dunn’s assault case as a mental health issue. But does his pattern of bad boss behavior get the same consideration?

For Dunn, the only viable answer is to be both transparent about his disorder and aware of his behavior. Today, in addition to sticking to his meds, therapy, and sleep schedule, he tells new acquaintances about his diagnosis as early as possible–at the start of a dinner party, say. He has a new startup, an early-stage social media company called Pumpkin Pie, and his small team knows he is bipolar.

At the same time, he tries to examine his own feelings at work, to sit back and listen, to avoid impulsive decisions. “Someone will say something that I totally disagree with, and I’ll feel this rising anger,” he says–“and I’ve learned to pay attention to it and work with my therapist on it. It’s like, ‘Well, why am I upset? It’s just a different idea about the future of our product. Why wouldn’t my first reaction be to pay attention to that?’ And what I’ve come to learn is that it’s usually because I don’t know what the right answer is.”

Whereas earlier in his career he styled himself as a kind of business pioneer and godfather of the digitally native, DTC brand movement, Dunn also now acknowledges that many of those brands, including Bonobos, have struggled to turn a profit. “I pioneered a bad business model,” he says.

And yet he’s no less ambitious than ever. Maybe more so. About that company Pumpkin Pie? It’s best described as Tinder for friendship–but based on personality traits rather than physical ones. Dunn conceived of it as a dating app for seniors, to help his mother-in-law find a companion, only to realize he’d devised a friend-finding tool for all ages. He also realized he’d grown jealous of the founders he was backing, who were busy building while he watched. So he asked for Zoninsein’s blessing and started hiring.

Today, he has 14 employees and $7 million in outside investment (plus his own money)–humble figures in the world of social media startups, but not, he says, because Pumpkin Pie represents a small swing. “I want to do a big one,” he says. “I want to run a big company at scale. I want to work on something for 15 years that is globally important.”

I mention that it’s the first time in all of our conversations about his past few years’ journey that I’ve heard some of that old swagger again. “I think it’s great at the beginning of a company to have an enemy,” he replies. And who is his enemy? “Facebook. I hate that company.” He wants to make some more money, too. “I think our country’s broken, and I think there’s an opportunity to put money into politics, something that I’ve gotten really into,” he says. “I want a bigger balance sheet to be able to do more good.”

Dunn is on a path to see if he can channel his most aggressive aspirations into his new, more considered approach to interacting with the world. Zoninsein is fully supportive. “It doesn’t make me worried,” she says, “because of the guardrails we’ve put up, the open lines of communication, the checks and balances with his doctor.”

Ask Brian Spaly if he would go into business with his old friend again, and the answer is an unequivocal no. “We didn’t really have any success together in business,” he notes. Still, for all his conflicted feelings, for all the personal and professional drama, Spaly believes there’s no reason Dunn’s history should stop him. “I do think Andy has in him the ability to be a world-changing founder,” he says. “I think he could do it. I really do. I believe in his goodness. I’m rooting for him.”

From the May/June 2022 issue of Inc. Magazine

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