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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Bill Gates didn’t stay at Harvard University for long — dropping out after three semesters to found Microsoft in 1975 — but he was there long enough to make an impression.

Gates’ former applied mathematics professor Harry Lewis, for example, remembers the future billionaire as being inquisitive and “mature” beyond his years, with a tendency for questioning adults and tackling difficult problems.

“He always wanted a challenge,” Lewis, who has taught at Harvard since the 1970s, told The Times of London in an interview that published last week. “I wasn’t surprised when he dropped out — I just wish I’d invested in him.”

Gates left Harvard early to launch Microsoft, which was then a startup in the nascent software industry. Microsoft ultimately turned Gates into a billionaire by age 31. It now has a market value of nearly $3.2 trillion, and Gates’ estimated net worth is $108.7 billion, according to Forbes.

If Lewis had invested $100 in Microsoft when the company went public in 1986, his shares would be worth roughly $650,000 today, after accounting for price appreciation and dividend payouts, according to a CNBC analysis.

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As a college student, Gates was surrounded by students whose math skills surpassed his own, giving him something of a wake-up call, he told The Times. He “nearly killed” himself by loading up on extra classes while spending hundreds of hours per month writing software code in the university’s computer lab, he said.

“It was, ‘Oh s—, there may be people better than me at math,’” said Gates, whose upcoming memoir “Source Code,” largely about his life pre-Microsoft, is set to publish next month.

Gates may have questioned his own math skills while at Harvard, but the tech pioneer also could have been a professional mathematician “if he wanted to,” Lewis told NPR in 2008.

In one specific moment, Gates’ precocious curiosity and eagerness to take on a challenge made him stand out, even among his gifted peers, Lewis told The Times: “The first day [of class] I showed them the pancake problem [a mathematical sorting question involving different-sized pancakes] and two days later he came back to show me he could do it better.”

Gates’ solution was published in an academic paper in 1979. “The problem remained pretty much in that state for 30 years,” Lewis told NPR, until some researchers finally improved upon Gates’ method in a 2008 research paper.

Ironically, those researchers were enabled by the development of the computer industry, which Microsoft was partially responsible for. “They never could have actually done the case analysis were it not for the computer industry that Bill Gates built in the intervening 30 years,” said Lewis.

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For more than 15 years, Jennifer Hyman has been the CEO and co-founder of Rent the Runway. For the last eight years, she’s also been a parent.

Doing both requires effort, says Hyman, but not the kind that involves waking up at 4 a.m., working late every night, missing kids’ sporting events or other commitments that some CEOs make. She wakes up at 7:15 a.m., eats breakfast with her three kids — and then works “like a maniac” at Rent the Runway’s office in Brooklyn, New York, so she can get home for family dinner, she says.

If Hyman has to miss family dinner — recently, she had to meet with an investor after work, for example — she reminds her kids that they’ll have to make those choices someday, too, she says.

“I’m certainly a working mom, and I think that’s incredible for my kids to see,” she says. “I’m constantly emphasizing to them … ‘I love my job. This is a big part of who I am, and I want you to love your job [one day], too.’”

Hyman co-founded Rent the Runway in 2009 with Jennifer Fleiss, her classmate at Harvard Business School. She’s been CEO since Day 1, navigating the company through both highs — a diluted $1.7 billion valuation on its stock market debut in 2021 — and lows, including layoffs and store closures in recent years.

Having time for both work and family — plus time for friends — isn’t a casual accident, Hyman notes: She doesn’t really have any hobbies, and she takes early-morning or late-night flights to avoid spending more nights than necessary away from her kids. But people in “any given job” can struggle with the same tensions, she says.

“There’s this assumption that women feel like they can’t have it all, and like you have to make sacrifices,” says Hyman. “I’ve done the things that are fulfilling for me. I don’t feel like I’ve had to cut anything out of my life that’s cut out happiness.”

How you spend your time can impact your career, relationships and emotional well-being, according to experts. Plus, dwelling on perfect work-life balance can be counterproductive and cause undue anxiety, Harvard Medical School and MIT professor Jeff Karp told CNBC Make It last year.

“We hear these things from others: ’trust in the process [and] ‘we need more balance’ … It ends up being very frustrating and can lead to anxiety, because we’re constantly feeling like we’re not in balance.” said Karp, whose 2024 book “LIT: Life Ignition Tools” focuses on how to tap into a “high-energy brain state.”

No one-size-fits-all strategy exists for parenting and having a busy job at the same time, Hyman says: Everyone has a different approach. Billionaire Raising Canes co-founder and CEO Todd Graves used to host dinner and playtime with his kids and wife at his office so he could go back to work afterward, he told CNBC Make It last year.

Similarly, Graves has been willing to wake up at 4:30 a.m. on vacations to get some work done, before joining the rest of his family at the beach by 11 a.m., he said. That kind of commitment isn’t quite as necessary if you’re happy with your level of success, he added.

“I’m as busy as anybody I know, I travel as much as anybody I know, but I can work my schedule where I can make most of the things I need to be at with kids, family or important friends,” said Graves.

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Elizabeth Gore has hired and interviewed “hundreds of people,” she says.

Gore worked at the United Nations Foundation then Dell helping entrepreneurs around the world build their businesses. In 2017, she co-founded Hello Alice, a platform helping entrepreneurs gain “access to capital like grants, loans, credit,” she says, and connecting them with a network of like entrepreneurs.

When it comes to finding the right candidates during job interviews, she loves asking questions like, “what do you think we’re doing wrong at our company?” as a way to gauge what they can bring to the table, she says. She also pays attention to what turns her off.

Here are two of her biggest red flags.

Gore’s No. 1 red flag is seeing that a candidate is focused solely on what’s in the job description. It’s fine to think about that list of tasks, “but how are they going to go beyond it?” she says.

The job description outlines the basics of what a job entails, but it can’t cover everything, especially original initiatives. “How are they going to stretch?” Gore says about what she considers. “How are they going to push our company goals? What innovation are they bringing to the table?” All of these could mean success for her company down the line.

To see if a candidate has thought beyond the listing, she’ll ask questions about their ideas for the company and try to get feedback about what the company could be doing better. If they come with critical thoughts and relevant pitches, that’s a good sign.

This kind of expansive thinking is especially important at startups. Employees have to innovate, but they often also have to wear many hats. “Our motto is ‘everyone takes out the trash,’” says Gore. She wants something who’s going to do whatever is necessary to move the team forward.

Sussing out what candidates are focused on helps Gore uncover her second red flag: people coming into the interview unprepared.

If she asks a question like, “what other ideas do you have?” and the answer is “well, you know, I would have to do more research,” she says, “or I didn’t have time to look into the company,” it’s clear they didn’t bother to do the bare minimum of learning about the opportunity, let alone think big about how to solve problems.

This behavior is unfortunately common. “I’m actually shocked at how many times people don’t do their homework,” Adriane Schwager, CEO and co-founder of hiring platform GrowthAssistant, previously told Make It. Her biggest piece of advice to people at any experience level is to show up prepared.

Gore is most interested in candidates who have “done significant research on the company” with “ideas to bring,” she says. Those are the people who could help her company reach its goals.

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Have you ever been to a party and heard “So what do you do?” about 30 seconds into every conversation? If you’re like most people, you probably responded with your role and company’s name. But if you want to sound really interesting, you have to use a different formula. 

As a global communication expert, I’ve worked with a lot of smart and talented people to help them elevate their presence and boost their confidence at work. Over time, I’ve discovered that the key — and often missing — ingredient for better small talk is relatability. 

In my book, “Smart, Not Loud: How to Get Noticed at Work for All the Right Reasons,” I lay out how you can build relatability, which increases engagement and connection, by answering the ubiquitous “What do you do?” question with this formula:

“You know how [talk about issues you solve]? So what I do is [share the solutions you offer]. In fact, [drop some proof].”

Let’s break down the three steps:

There’s nothing wrong with answering “What do you do?” with your company and job title. But it doesn’t tell people much and, frankly, it’s just not that interesting. 

Instead, start with a rhetorical question. For example:

• “You know how cyberattacks are getting more frequent and sophisticated?” 
• “You know how you see ads when you scroll through a news story?”

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What you’re doing with this rhetorical question is referencing an everyday problem your conversation partner may have heard about or even encountered firsthand. It paints an interesting visual people can relate to and understand, whether or not they’re familiar with your job function or industry. 

Now it’s time to dive deeper into what your work involves, by following up with the solutions you offer. If you’re not sure how to articulate this, think about the real-life implications of what you do every day. 

Building on the examples above, you might add: 

• “What I do is create software systems that alert companies when a suspicious user tries to access their platform.” 
• “What I do is research the best places to put ads so that they have maximum visibility.” 

Conclude your response with some evidence or context. This is where you can use company names, numbers, or a story to tie it all together. 

For example, finishing out the examples above, you might say: 

• “In fact, our organization is one of the largest cybersecurity companies in the world with clients like [well-known company].” 
• “In fact, the click-through rate of our ads is around 3%, which is much higher than the industry average.” 

This kind of closing gives weight to your claims, makes your work tangible, and solidifies your credibility. 

I used this trick myself on a recent flight. I said:

“You know how communicating clearly and confidently is one of the most important workplace skills, but so many people and teams struggle with it? What I do is speak at conferences and facilitate workshops to help teams collaborate better at work. In fact, I have a communications book out and I’m headed to an event now.”

Suddenly, the person I was chatting with had so many questions because he could relate. 

Since the “What do you do?” question is bound to come up, you can rely on this small talk strategy to craft a compelling introduction, talk about your work, and connect with new people in a more meaningful way.

Jessica Chen is a global communications expert, keynote speaker, and a former Emmy-Award Winning TV journalist. Her new book “Smart, Not Loud: How to Get Noticed at Work for All the Right Reasons” teaches smart professionals how to develop workplace confidence and build a career they love using strategic communications skills to stand out. Connect with Jessica on LinkedIn and Instagram. 

Want to up your AI skills and be more productive? Take CNBC’s new online course How to Use AI to Be More Successful at Work. Expert instructors will teach you how to get started, practical uses, tips for effective prompt-writing, and mistakes to avoid. Sign up now and use coupon code EARLYBIRD for an introductory discount of 30% off $67 (+ taxes and fees) through February 11, 2025.