This week, the founder of activist short-seller Hindenburg Research, Nate Anderson, published a personal note to his network discussing why he was disbanding the firm. He started the company in 2017, and began publishing damaging reports on large businesses like Carvana, Nikola, and Adani Group alleging shifty practices. Over the years, Hindenburg has tanked the stock of many large companies, obliterating billions from their market values. It was satisfying for Anderson—until it wasn’t. 

“Fraud, corruption, and negativity often seem overwhelming. Early on, a sense of justice was usually elusive. When it happened, it was tremendously fulfilling. It kept us going when we needed it,” Anderson wrote. But as the firm began to grow and become more impactful, the work became “rather intense, and at times, all-encompassing.” His job would even infiltrate his dreams, seeping into the deepest parts of his consciousness. 

Anderson spiraled into isolation as Hindenburg’s success heightened. And he’s not the only founder who came to this realization after the fact. Other prosperous leaders have voiced how damaging the grindset has been to their personal lives and social health.

It’s lonely at the top—but it may be isolation of their own making

Reflecting on their come-ups, some successful founders can pinpoint when the loneliness started to creep in. But they also tend to scrutinize themselves, and conclude their isolation is a byproduct of their own choices. 

“Someone once told me that at a certain point a successful career becomes a selfish act. Early on, I felt I needed to prove some things to myself,” Anderson wrote in his personal note. Closing out his stint as the leader of Hindenburg, he said he has now found comfort for “the first time in his life.” 

“I probably could have had it all along had I let myself, but I needed to put myself through a bit of hell first. The intensity and focus has come at the cost of missing a lot of the rest of the world and the people I care about,” Anderson wrote. “I now view Hindenburg as a chapter in my life, not a central thing that defines me.”

Brian Chesky, the co-founder and CEO of Airbnb, also experienced a similar epiphany during the height of his career. In 2020, the short-term rental company went public, and shares opened at $144.71 on the Nasdaq. It was labeled as one of the most successful IPOs in history, and the company’s valuation shot up to around $103 billion. But Chesky wasn’t as jubilant as one would expect—in fact, he described it as one of the “saddest periods” of his life.

“I had this image that if I got successful I’d have all these people around me, all these friends, I’d have all this love, all this everything, and my life would be fixed,” Chesky told Dax Shepard on the Armchair Expert podcast. But as the leader of a now wildly successful company, there was a power imbalance in socializing with his employees, and they all had their own personal lives and families to get home to anyways. 

“Suddenly, I remember waking up feeling totally isolated,” Chesky said, noting that this experience isn’t unique to people in his position. “No one told me when I started on this journey how lonely and isolating it would be. And that’s okay—it was for me to learn.”

But Chesky concedes that he put himself in that situation by primarily seeking connection through his business, and not through the people who are important in his life. 

“I had done that. I had isolated myself totally focused on working, continually feeling like I’m not enough, we’re not enough, we need to be better,” he said on the podcast. “Whenever I would make time with friends and family, the guilt was I wasn’t working on the company.”

The same thing happened to Vinay Hiremath, the co-founder of Loom, a video-messaging platform that was sold to Atlassian in 2023 for $975 million. Earlier this month, the newly rich entrepreneur opened up about his success in a blog post titled “I am rich and have no idea what to do with my life.” He detailed his come-up, and the emotional pitfalls that came with it. 

“Life has been a haze this last year. After selling my company, I find myself in the totally un-relatable position of never having to work again. Everything feels like a side quest, but not in an inspiring way,” he wrote. “I have infinite freedom, yet I don’t know what to do with it, and, honestly, I’m not the most optimistic about life.”

Hiremath explained that in Loom’s early aughts, he felt more secure about his life trajectory. He was happy, and felt he could get through issues if the company went belly-up. But that all changed when the business surged in success. He lost sight of himself as an individual; he got into frequent arguments with his long-term girlfriend, and they broke up; he had to come to terms with being insecure. 

“As the company continued to skyrocket to new heights, I started to have growing expectations for myself, and others started to have growing expectations of me,” Hiremath wrote. “When we went through our first round of layoffs, this company my ego was hitched to had suffered a massive blow, so I lost myself. This whole chapter of Loom has created a complex web of internalized insecurities I must now work hard to disentangle and free myself from.”

Moving forward from the isolationist ‘grindset’

As emotionally debilitating as success can be, these founders managed to confront their loneliness and isolating grindset.

At the end of his personal note, the Hindenburg Research founder mentioned looking forward to rebuilding the relationships damaged in his rise to the top. 

“To my family and friends, I’m sorry for the times I have ignored you while I let my attention be drawn away. I can’t wait to have more time to share with you together,” Anderson wrote. 

Chesky has also come to terms with his situation—with help from one of America’s most beloved presidents. In his Armchair Expert podcast episode, the Airbnb co-founder said back in 2020 and 2021, he and former President Barack Obama were having weekly conversations. Chesky described Obama as being a mentor during this time, and after writing a letter to the retired head of state in early 2021 describing his emotional pitfalls, received an invaluable piece of advice.

“I asked him, ‘How did you not lose your shit as president? How did you stay grounded?’ And he said, ‘You’re connected to your roots. And the roots are your relationships and your past,’” Chesky recounted. He was tasked to think of a large group of friends he could casually call up out of the blue, without it seeming random or unconventional. But Chesky drew a blank—he couldn’t think of any.

“So then I decided to reconnect with my college friends, with my high school friends. And I started spending time with them, taking trips. And it totally changed everything about my life,” Chesky said.  

Other leaders like Loom co-founder Hiremath have taken a less conventional path in broaching loneliness and insecurity. After breaking up with his girlfriend, he decided to climb a 6,800 meter peak in the Hilmalayas to “externalize” his emotions. Later, Hiremath chose to move to Hawaii and learn physics, so he could launch a company that “manufactures real world things.” He said his goal is to accept that he’s happy simply learning physics—even if it doesn’t pan out to be as successful as his previous ventures. 

“If this means I’ll never do something as spectacular as Loom, so be it,” Hiremath wrote. “It’s been too long since I’ve been completely raw and real with myself, so I’m applying a healthy dose of humility to everything I say and do. It’s the only thing that feels authentic.”