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‘I thought money would solve all my problems’: 31-year-old sells his startup for $100 million. Then spirals into depression

‘Call me naive, but I thought money would solve all my problems.’

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Rebecca Leib

A screengrab of a tweet with gold swirls and a depressed in shadow.

Many say “money can’t buy happiness,” and one millionaire whose message is making the rounds on the internet agrees. Despite selling his startup for millions, Jake Kassan admitted on Reddit that he was lost and unhappy and gave advice to those on how to fare better.

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Now, his post is being circulated on X, YouTube, and Reddit, with users sharing their own recommendations for a life full of success, happiness, and fulfillment.

‘I always thought this was the dream’

In 2023, Kassan shared a post in the subreddit r/findapath entitled “Sold my company for millions and more lost than ever (31 years old).” In his post, he talks about how, after selling his company for a “lot of money,” he began feeling unfulfilled. “I always thought this was the dream and that id be happy forever…until i wasn’t,” Kassan said. “I realize I’m in an incredibly unique situation and wanted to share some things I’ve learned and am still working through.”

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Kassan went on to say that initially, he didn’t have any passions, so his career became one of money and ease. Bound to “an unhealthy relationship” with himself, Kassan’s drive came from his own ego.

He built bigger and better professional successes without thinking if they made him authentically happy or fulfilled. Eventually, he sold his company for a very large amount. “I’m 31, single and never have to work again.” Kassan says in the post. “I’ve also been lonelier than ever and deeply depressed.”

The post ends with Kassan admitting he’d been doing some internal work to understand his own authentic motivations and passions. He encouraged readers to do the same, even if it doesn’t end in their desired outcome. “Even if its the wrong direction and we fail or realize we don’t like what were doing,” said Kassan, “you can not live without struggle and pain. We either choose our struggle and pain or it will find us through depression and loneliness.”

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The message garnered over 600 upvotes and 345 comments, with users initially wishing they were in the financial position that Kassan was. “For real lmao, money would literally solve all my problems and extreme anxiety right now,” said user @KeepItTrillBill. “If your money’s not helping, feel free to send some my way,” suggested user @parchmentheart.

Reactions to Reddit post about a rich man who is unhappy
u/JakeKassan via Reddit

‘One of the most meaningful things we can do’

Kassan’s sentiments stayed primarily on Reddit until Jan. 21, 2025, when Kassan shared a video on his YouTube channel called “At 30, I Sold My Company for $100 Million, Now I’m Lost,” reiterating the journey that led to his unhappiness he originally shared on Reddit. “Call me naive, but I thought money would solve all my problems,” the video stated. “But instead, it just created new ones.”

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A youtube screenshot of Kassan's youtube video
JakeKassan/Youtube

The video amassed over 25,000 views, with commenters welcoming him to YouTube and calling his journey inspiring. “Awesome video man, sharing stories like this to the world is one of the most meaningful things we can do.” said one viewer. “One of the most genuine videos I’ve come across in a while. The quality makes me feel like I just discovered a hidden gem,” said another.

A youtube screenshot of Kassan's youtube video
JakeKassan/Youtube

‘The soul craves authenticity’

After the video release, CNBC profiled Kassan on Jan. 29, 2025, which led to more media attention around Kassan and his story. A day later, X user @gregisenberg shared a screengrab of Kassan’s original Reddit post, captioning the entry “31 year old guy who sells his startup for $100 million shares why he is depressed and how to think about your career/life.”

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The post received over 220,000 views, 4,200 likes, and over 100 comments, praising Kassan’s honesty and reiterating that human beings need purpose—not just financial success. “Tell this guy to dm me, ima lead him to Christ and we gon serve God together,” said one commenter. “Chasing shadows of success, yet the soul craves authenticity. Embrace struggle; it’s the path to true meaning,” said another commenter.

‘I lost purpose’

According to the CNBC profile on Kassan, in 2018 he sold his Los Angeles-based accessory brand MVMT Watches for 100 million dollars. Kassan had started the company as a 21-year-old college dropout, seeing success and financial freedom. “The North Star when I was younger, was always financial freedom,” Kassan told CNBC. “So my purpose, I always felt was: I wanted to make money.”

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Two years after he sold his company, Kassan realized his previous beliefs felt inauthentic. “For the first time in years, I don’t want to talk about MVMT anymore, but I also didn’t know what to talk about, and I couldn’t find anything that felt as important as that entrepreneurial journey,” he said. “I think I lost purpose.”

According to a comment Kassan made on his original Reddit post, the 33-year-old is working on exploring his interests through video. Though he didn’t feel comfortable on camera, getting out of his comfort zone was part of the journey.

“You wont love 100% of what you do for your career,” he said. “Oftentimes, facing your fears is some of the most rewarding and fulfilling ways to live your life. “

Reddit comment ffrom original poster about what his passions are.
u/JakeKassan via Reddit
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The Daily Dot has reached out to @JakeKassan via direct message on Reddit and X. The creator did not immediately respond to the request for comment.

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