At 27, he sold his company MVMT Watches for $100 million

When Jake Kassan sold his company for $100 million at the age of 27, he thought the money would make him happy. Though it did temporarily, it eventually took away his sense of purpose and threw him into cycles of anxiety and depression, he said.

In 2018, Kassan sold his Los Angeles-based accessory brand MVMT Watches — pronounced “movement” — to the Movado Group in a deal that left him walking away a multi-millionaire. The company, which he had started as a 21-year-old college dropout, granted him the financial freedom he sought.

“The North Star when I was younger, was always financial freedom,” Kassan told CNBC Make It. “So my purpose, I always felt was: I wanted to make money.”

“Then you sell [your company] and then … 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.”

Today, the 33-year-old is working on regaining his sense of purpose and redefining what happiness means to him.

As a kid, Kassan said, he was never particularly good at school. Instead, he saw more value in making money.

“Academically, I’ve just never done [well]. I’ve always been probably just a little below average,” Kassan said. “Call it ADD (Attention Deficit Disorder) or whatever they want to label it as these days … I’m very good at being hyper focused, and it’s a strength and a weakness of mine, to be honest.”

“I found that if there’s something I’m interested in, I’m extremely focused and almost obsessive over that thing to the point that you kind of will it into being successful, but also sometimes you sacrifice other areas of life,” he said.

Kassan’s first “business” involved selling lollipops when he was in the seventh grade. By college, he had already gained years of business experience. Before starting MVMT, he launched an interactive glow-in-the-dark T-shirt business in 2008.

At the time, he was studying at the Santa Barbara City College, before dropping out after his first year.

“I just didn’t know why I was doing it. I was doing the routine, going in circles … after a year of [going to classes] and having a business at the same time, I dropped out to pursue that business,” he said.

Unfortunately, he said, that company, which relied mostly on a brick-and-mortar storefront, failed after competitors taking a digital-first approach entered the space. But that taught him a big lesson that would feed into the success of his next venture: focus on e-commerce instead.

By June 2013, Kassan founded MVMT Watches — which took an online approach — with his college roommate Kramer LaPlante, and over about five years, the two dropouts amassed a million followers on the brand’s Instagram, built a team of 45 employees and ultimately sold the company for $100 million.

“Fast forward to the day where it happened … you wake up and you look at the Chase app that you’ve always opened, and now you see your bank account looks like a phone number,” he said. “In some ways, a lot changes. In some ways, nothing changes.”

Although he was able to afford a nicer lifestyle and help his friends and family out financially, that high quickly wore off, he said. Kassan, who had struggled with anxiety and panic attacks before, said his mental health worsened in the years after selling his company.

“It was great at first, because I was just enjoying being in the moment. But at some point … it just felt like Groundhog Day. It’s like, there’s got to be something more,” he said.

“As time passed, I couldn’t help but start to feel this void growing inside me,” Kassan said in his recent YouTube video. “I finally climbed to the top of my mountain, but I didn’t find what I was looking for.”

Not only did he lose the sense of challenge that he craved in life, but he also lost his drive and identity, he said. On top of that, Kassan said, he struggled to find the right person to talk to about how he felt.

“I turned 30, I [had] just gone through a breakup … I had friends and stuff, but still, just finding people who understood [how] lonely it felt at times … it just felt emotionally depleting,” Kassan told CNBC Make It.

“How do you empathize with someone who is rich and depressed?” he said in the video.

One night in 2024, Kassan was on a trip in Australia with friends when he had a panic attack in his hotel room.

“I’ve had panic attacks before, but this was … completely out of left field,” he said. “It was the first one that I had in years. This flood of thoughts just [came] in. It was a really dark moment that just crippled me,” said Kassan.

However, after weeks of reflection, he realized that he needed to work on something again that challenged him, gave him purpose and a sense of genuine enjoyment.

“At one point, I think it might have been after the panic attack, where [I said]: ‘Okay, I need to change my focus and really start to [work] more or less on showing up,” he said. Rather than being so concerned over the destination, he decided he would simply start working again like he did when building MVMT.

“I think the gym is the best analogy for it. If you don’t see results after week one or week two … when you’re months down the road, you start to actually see all the benefits from your work,” he said.

He also learned that what made him so fulfilled while building MVMT and his other entrepreneurial endeavors was the fact that he could be creative. That discovery led him to zero in on videography and storytelling.

Today, Kassan is working on building his YouTube channel. He is also an angel investor for companies on the side. Businesses he’s invested in include prebiotic soda company Olipop and sauce company Truff.

“I can’t buy more peace of mind,” he said. “That’s my relationship with money. I’m grateful for it. I appreciate it. I’d rather have it than not have it … but there’s nothing that it can do that is going to make me a happier person.”

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