This story is part of CNBC Make It’s The Moment series, where highly successful people reveal the critical moment that changed the trajectory of their lives and careers, discussing what drove them to make the leap into the unknown.

Jay Chaudhry never thought he’d run a business, amass a fortune or help popularize an entire industry. Not growing up in rural India, not upon moving to the U.S. in 1980 to study engineering and marketing, not even after landing jobs at tech giants IBM and Unisys.

“I have no background of entrepreneurship in my family of small-scale farmers. So if you asked me, ‘Did I ever think about becoming an entrepreneur in my childhood [or] early years of my career?’ Not really,” Chaudhry, the billionaire founder and CEO of cloud security company Zscaler, tells CNBC Make It.

It took Silicon Valley’s dot-com boom — the wild success stories of tech startups like Netscape — to get Chaudhry thinking in 1996, “Why shouldn’t I start a company?” He made the rash decision to quit his job as an executive at Atlanta-based tech company IQ Software, and his wife Jyoti quit her job as a systems analyst at telecommunications giant BellSouth.

Together, they plunged their life savings — roughly $500,000 — into SecureIT, a cybersecurity software startup they co-founded in 1997. At the time, “maybe less than 5% of Fortune 500 companies had firewalls,” Chaudhry says. “Within 18 months, we had deployed firewalls in about 50% of [the] Fortune 500.”

His timing was perfect: In 1998, Chaudhry sold SecureIT to VeriSign in an all-stock deal worth nearly $70 million. Over the ensuing decade, the husband-and-wife duo founded two more cybersecurity companies and an e-commerce business, each of which got acquired.

By 2007, they were already wealthy entrepreneurs, and Chaudhry — who gets “bored” without something to work on — decided it was time to launch “one big company and put 200% focus on that,” he says.

That company was Zscaler, which aimed to help companies transition away from outdated firewalls and into the cloud era. The couple invested $50 million of their own money, says Chaudhry. Today, it brings in $1.6 billion in annual revenue and has a market value of roughly $30 billion.

Chaudhry’s own net worth is estimated at $11.5 billion by Forbes.

Here, Chaudhry talks about putting his family’s savings on the line to follow his gut, how his upbringing influenced his relationship with money and the advice he’d give someone who wants to quit their job to start a business.

CNBC Make It: What prompted you to stake your entire life’s savings on a startup idea — in an industry that didn’t really exist yet?

Chaudhry: This thing happened because I love to read and I love technology.

In 1996, Netscape had just launched and gone public, and I was fascinated by it. I said, “If [Netscape co-founder] Marc Andreessen could start a company — he was a young guy [right] out of college — why shouldn’t I start a company?”

My wife and I talked a few times, and the more we thought about it, the more conviction we got around it: [Netscape’s web browser] is the way to access information, and it should become popular. But if every company is connected to the internet, that means there will be security risks.

That was my simple thinking. There was no IDC or Gartner study about the market size. It was largely based on what the gut told us.

A gut feeling is one thing. Betting every dollar to your name is another.

It started out with us saying, “Let’s go get venture capital funding.” I had no experience raising funds, and I realized soon that it wasn’t that easy. This was [1996], Atlanta was not a VC mecca and we kept hearing, “Hey, you don’t have any experience.”

We were disappointed, but our conviction was building, which led to me saying, “Why don’t we put our life-savings on the line?”

I didn’t know anything. So, I really didn’t know how big the risk was. I couldn’t quantify it.

How did you make peace with that risk?

After talking back and forth, we asked each other, “What’s the worst thing that can happen?” The company could shut down, we’d lose all of our savings.

The next question was, “Can we find jobs?” There was lots of confidence that we could.

I never had money in my early childhood, so there was never a notion that I must buy A and B and C. Our lifestyle was pretty simple. Our house in Alpharetta, Georgia, was $200,000 — a nice, typical middle-class house at that time — and we didn’t have any fancy cars or fancy payments.

Our only child at that time was going to a public school. There wasn’t a lot of overhead. We said, “Let’s take a chance.”

When a bet pays off, does that success make you more confident to take on bigger risks? Were any of your other ventures as risky as that first one?

The [financial] risk of SecureIT was, like, 1,000 times more than the risk of Zscaler. The amount I invested in Zscaler was a small fraction of my net worth.

But Zscaler was much harder. I put more money in it than all the others combined. I took bigger bets. I hired people more quickly to solve some very hard problems. I wanted to do something big, something lasting.

We were trying to solve a problem that was futuristic. Will it be successful or not? Will the market take off or not? That was all unknown.

So if you asked me the chances of success of Zscaler, there was a much higher risk. Because, with SecureIT, it was fairly obvious that as you connect to the internet, you need firewalls.

What’s your best advice for someone who’s thinking about quitting their job to start their own business?

First, build conviction by learning more about what you want to do. Don’t just do some of the cursory work.

Second, start by putting in your own money. That actually is part of testing your conviction. If you really have conviction, you’ll take a chance on yourself. That also means you’ve done some serious homework, you’re ready, you’re committed.

You can also make decisions the way you want to make decisions. If Zscaler was largely owned by VCs, they probably could have shut it down. It took us a few years to really start getting traction in the market, and VCs can write you off and move on. They say, “It’s one of my 20 investments.”

When you put in your own money, this is the only business you have.

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Sarah and Jamie McCauley are landlords, YouTubers, Walmart pallet flippers, eBay resellers and Amazon product reviewers — and those are just their active streams of income.

The McCauleys make their money by researching what makes side hustles profitable, testing them and teaching others how to do the same on YouTube. The Grand Rapids, Michigan-based couple earned nearly $140,000 from eight streams of income last year, according to documents reviewed by CNBC Make It.

They’re particularly good at two types of gigs, they say: anything involving real estate and their YouTube channel itself, where they share their side hustle exploits with at least 146,000 subscribers.

“If you’re looking to just make some extra money on the side, maybe pay off a credit card debt or pay for a vacation, I think that is doable for nearly everybody,” says Jamie.

DON’T MISS: The ultimate guide to earning passive income online

The McCauleys are part of a side hustle revolution, a growing number of Americans who supplement income with multiple jobs. More U.S adults — about 39%, according to Bankrate — have side hustles today than ever before, whether out of necessity, precaution or a desire to increase their earning power.

Ease of starting is at an all-time high: Platforms like Amazon, Airbnb and Fiverr offer instant access to paying customers. But with competition also rising, it’s hard to build a side hustle that regularly brings in revenue.

Make It spoke with a selection of Americans with successful side hustles to learn how they built their businesses, and used them to fund a wide variety of financial goals. Every respondent highlighted four common traits that helped drive their success:

No matter what you sell, you need people willing to buy it. Jenny Woo says her side hustle is successful for a simple reason: She researches her audiences intensely, and tailors her products specifically to them.

Woo is an adjunct lecturer at the University of California, Irvine, a freelance business consultant and the teacher of an online course about emotional intelligence. Her one-woman side hustle, called Mind Brain Emotion, sells 12 different emotional intelligence-themed card games.

It brought in $1.71 million on Amazon last year, according to documents reviewed by Make It.

Woo’s first deck of cards, “52 Essential Conversations,” was tailored toward parents who — like her — wanted to connect with their kids and build their emotional intelligence skills. She joined parenting Facebook groups and observed users’ posting, commenting and liking habits, she says.

After selling $10,000 worth of the game in a 2018 Kickstarter campaign, Woo kept researching. She conducted a survey of her consumers, and learned that “overwhelmed” teachers looking to support children’s social and emotional development made up a significant portion of her audience, she says.

Her second deck, “52 Essential Relationship Skills,” was built for those teachers. It didn’t sell as well as her first deck, but it taught Woo that she could broaden, and combine, her audiences.

Woo applied that lesson to her third game, “52 Coping Skills.” She started with her own experiences working with college students during the Covid-19 pandemic and combined it with her continued research on teachers and parents, she says.

It’s now Mind Brain Emotion’s top-selling game, says Woo.

Woo sells on Amazon, which has a broad reach, to collectively rope in Mind Brain Emotion’s hyper-specific audiences. Tim Riegel’s products have a more singular customer base, so he sells on Etsy, a marketplace known largely for homemade and handmade goods.

Riegel, a full-time general manager at a sheltered workshop, makes firepits from recycled tank ends in Lamar, Missouri, and sells them under the name Mozark Fire Pits. His average product weighs 225 pounds, and sells for $950.

Mozark Fire Pits brought in approximately $202,000 on Etsy last year, according to documents reviewed by Make It. Riegel maintains a 40% profit margin, he says.

Riegel chose Etsy over platforms like Amazon, Wayfair and Overstock because it felt more user-friendly, and a better fit for his personalized products, he says. He also sells on Facebook Marketplace, which costs him more in advertising — but less in shipping costs for customers within a 200-mile radius, he adds.

That kind of platform analysis is valuable, no matter what kind of side hustle you run.

If you sell a service, instead of a good, you might consider platforms like Fiverr and Upwork — popular among photo editors, marketing writers and voiceover artists — or Taskrabbit, known for labor-intensive side hustles like cleaning or repair work.

Or, opt out of those platforms entirely. If your gig is something that many other people also do, try finding marketplaces with more narrow niches like Contently, Skyword or ServiceScape, recommends side hustle expert Kathy Kristof.

“One of the problems I see with a lot of freelancers is that they go to the best-known online platforms … and those platforms are so saturated with people who have been there for, often, decades,” says Kristof, whose blog SideHusl has reviewed more than 500 different side gigs.

No matter your platform, you’ll need to stand out. A good listing can help: clear and concise, written for your intended audience, free of typos, with high-quality graphics and some search engine optimization (SEO).

Becky Powell, a kindergarten teacher based in Beaverton, Oregon, has a side hustle selling worksheets for other educators on an online platform called Teachers Pay Teachers. Many of her worksheets focus on her personal specialty, teaching children sight-reading skills.

Her side hustle didn’t take off until she embraced SEO. When she uploaded her first worksheets, she titled them, “Creating sight words with pattern blocks.” Sales slowly trickled in.

Her husband Jerome, who has a business background, suggested a simpler title, like “Hands-on sight words.” The sight-reading worksheets quickly became her bestselling products, Powell says.

Powell’s store brought in $125,500 in 2022 revenue, according to documents reviewed by Make It. Her husband also sells worksheets on the platform, and they’ve used their combined earnings to fund vacations and pay down their mortgage and student loans, Powell says.

“You have to have passion and knowledge,” she says. “You also have to have a business sense [and understand] SEO.”

Once you gain enough customers, work to turn your sales into positive reviews, so you appear higher in platforms’ search results, Kristof advises. Customer service, prompt shipping and quality control can usually earn you a good online reputation.

The McCauleys have a rule for their ever-changing collection of side hustles: “You either have to be one of the first to get there, or your approach has to be very unique and different to be successful,” Sarah says.

But being first or unique doesn’t guarantee long-term success. In 2020, the couple was early to a side hustle trend: pallet flipping. At local warehouses, they’d buy pallets of returned goods from Amazon, Walmart or Target. They’d unbox the pallets, discover their contents and resell the items for a hopeful profit.

From December 2020 to December 2022, the McCauleys made about $19,500 in pallet-flipping profits, they estimate. Their most popular unboxing YouTube video got 5.4 million viewers, translating to an additional $30,000 in advertising revenue, says Jamie.

Last year, more Americans hopped on the pallet-flipping trend. Pallet prices rose, resale values dropped and a slew of unboxing videos diluted the McCauleys’ viewership. “The pallets became not really worth our time … from the standpoint of time over money,” says Sarah.

Four years ago, the McCauleys would’ve simply moved onto their next side hustle. Now, they’re feeling the strain of constantly building new gigs from scratch, and starting to reorganize their income streams into a smaller number of longer-term projects.

Instead of flipping their current home renovation project in Northern Michigan for a profit, for example — something they’ve done multiple times — they’ll keep it as their own vacation house and part-time Airbnb rental, they say.

“We always knew [side hustling] was going to have an expiration date,” says Jamie. “It’s a young person’s game, to always be looking for what’s next.”

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In April 2021, Paul Lee took a vacation to Thailand. Five months later, he decided to leave the United States behind and make a permanent move to the Asian country.

Lee, originally from Georgia, had been living in New York City and grossing around $1 million a year thanks to his e-commerce business. Despite doing well enough to pay for his parent’s retirement, the 28-year-old tells CNBC Make It he found himself without purpose, feeling depressed, and needing to make a change.

“When I first arrived to Thailand, I just felt rejuvenated. Everything was completely new to me, and I felt like it was a fresh new start,” Lee says. “The more and more I live here, the more and more I fall in love with the city.”

Since moving to Bangkok, Lee has been making around US $150,000 a year as a content creator and real estate agent, according to documents reviewed.

Working in real estate helped Lee find several living arrangements in Bangkok, including luxury condos. The apartment he’s in now is a one-bedroom in the Thonglor neighborhood which Lee says is “the Soho of Bangkok.”

It’s a 650-square-feet unit that costs 20,000 baht — around USD $544 — in monthly rent. Lee also pays $20 for Wi-Fi, $80 for electricity, and $3 for water each month. The apartment came furnished, and Lee has access to amenities, including a pool and a gym.

To move in, Lee had to pay a security deposit of two months’ rent or about $1,088.

Despite lower grocery costs in Bangkok, Lee eats out for every meal and spends $500 a month on food. “I’m not gonna lie, the food in New York City was very good as well, but I think in Thailand, it’s just a lot more homey, a lot more local, and a lot spicier,” Lee says.

His other expenses include a $93 monthly gym membership which is a bit of a splurge considering Lee has free access to a gym in his building. But the cost is worth it for Lee, because he can take advantage of the co-working space, coffee, and numerous networking opportunities in the space.

Also his current gym’s price is nothing compared to luxury gyms in New York, like Equinox, where memberships can start at $240 a month.

Lee has only returned to the U.S. one time since his big move to Thailand — for his sister’s wedding. He tells CNBC Make It he chose to leave New York City because he found himself being too materialistic and living in an “environment that was just very individualistic, very doggish, and very hyper-aggressive.”

“Bangkok stood out to me because it seemed very metropolis. It seemed very fun. It seemed very affordable and it just had a very good culture and didn’t really have any major compromises to me,” Lee says.

Lee has made a new life for himself in Thailand, he says, and returning to the U.S. doesn’t feel likely.

“I had to go through this journey of being poor and becoming quite wealthy to realize all this wealth that I had accumulated didn’t really give me what I wanted and didn’t give me the satisfaction I was looking for,” Lee says.

His parents were initially shocked he’d moved so far but ended up following in his footsteps when they moved to South Korea. They visit him in Bangkok from time to time, and Lee travels to see them, too. He says it’s one of the best perks of his new life in Thailand.

“At the end of the day, even though I don’t make nearly as much money as I made in New York City, I am far… wealthier in terms of my happiness, in terms of my well-being, my peace,” he added. “These are things I never was able to achieve back home in the States.”

Conversions from Thai baht to USD were done using the OANDA conversion rate of 1 baht to 0.02 USD on July 1, 2024. All amounts are rounded to the nearest dollar.

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The key to success is to never stop trying to learn new things, according to Amazon CEO Andy Jassy.

“You have to be ravenous and hungry to find ways to learn,” Jassy said last week in a video posted by Amazon about the company’s famous list of 16 leadership principles, originally penned by founder Jeff Bezos.

One of those principles, “Learn and Be Curious,” says the best leaders “are never done learning and always seek to improve themselves.” Jassy said he’s seen that ability make the biggest difference between people who successfully grow their careers and those who remain “stagnant.”

“For some people, at a certain point, they find it too threatening or too difficult to keep learning,” he said. “The second you think there’s little left for you to learn is the second that you are unwinding as an individual and as a learning professional.”

Continuing to learn as you age can improve memory and other cognitive abilities, while also making you happier, research shows. And employers are often keen on hiring and advancing workers with a “growth mindset,” where you continuously try to adopt new skills and improve your abilities, LinkedIn workforce expert Aneesh Raman told CNBC Make It in March.

Jassy and Bezos aren’t the only high-profile professionals who think that way: Julia Stewart, the CEO who merged IHOP and Applebee’s into a roughly $530 million restaurant giant, says that “You should be learning for the rest of her life” is her mantra.

Good leaders have to realize they don’t always have every answer, and be comfortable learning from the people around them, Stewart told Make It in May. “I think as you get older and you become successful, you realize: ‘I don’t have to be the smartest person in the room,’” she said. “I’ve never had somebody say, ‘No, I’m not going to help.’” 

Jassy agrees. “You have to think about the idea that you don’t know everything and that there’s a lot to learn,” he said. “Even if you spent many months or years learning a certain area, it may flip upside down very quickly.”

His advice: Stay humble in those upside-down moments, so you can find the joy in learning new things and continue to grow for the rest of your life and career. 

“Instead of that feeling threatening and scary, you have to think about that as being part of the fun of what you do,” Jassy said.

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When Mark Cuban sells a business, he always sets aside some of the proceeds for one specific purpose: divvying it up among the company’s employees.

“In every business I’ve sold I’ve paid out bonuses to every employee that was there more than a year,” Cuban posted Tuesday on social media platform X. The bigger the acquisition, the larger the payout: 300 of Broadcast.com’s 330 employees became millionaires when the audio streaming service sold to Yahoo for $5.7 billion in stock in 1999, Cuban wrote.

Cuban started the practice after selling his first company, a software firm called MicroSolutions, for $6 million to CompuServe in 1990. He took 20% of the total sale price, he tells CNBC Make It, and paid it out to 80 employees — which would equate to $15,000 per staffer, if distributed equally.

Cuban did something similar upon selling his majority stakes in HDNet, now known as AXS TV, in 2019 and the NBA’s Dallas Mavericks last year, he wrote in his post. “And only HDNet had any layoffs right after the sale,” he added.

Cuban’s co-founding and sale of MicroSolutions marked his first big entrepreneurial success and a triumph over setback: He nearly went broke after his secretary stole roughly $82,000 from the company.

“It was f—ed up,” Cuban told Barstool Sports’ “Pardon My Take” podcast in 2020. It also presented a silver lining, he added: “It made us get our s— together.”

The business bounced back, and Cuban sold MicroSolutions five years later, making him a millionaire. “You have to hustle the most when you think it’s the darkest,” he said.

In 1995, Cuban invested in and took operational control of AudioNet, the streaming platform that eventually became Broadcast.com. The business idea was met with skepticism at a time when the internet was still fledgling, he told CBS’s “Sunday Morning” last year.

“There was nobody doing it. Nobody,” Cuban said. “People thought I was an idiot.”

Upon selling Broadcast.com, Cuban received a large portion of Yahoo stock, which was considered highly valuable at the time. But instead of holding onto it, he quickly cashed out. He was happy with the money he’d earned and suspected the stock market was overpriced, he told GQ in 2022.

Months later, the dot-com bubble burst and Yahoo’s share price sank. “It taught me a hell of a lesson: When you just chase dollars, it never works out well,” Cuban said.

Last year, Cuban sold a majority stake in the Mavericks to the Adelson and Dumont families, who run Las Vegas Sands Corporation, in a deal reportedly valuing the franchise at roughly $3.5 billion. He retained a 27% ownership stake and control of basketball operations, the Associated Press reported at the time.

The deal ended Cuban’s longtime status as an NBA majority owner. In 2000, the newly minted billionaire purchased his initial stake in the team for $285 million — without negotiating or trying to push the price down by even a penny.

“It was all about fun,” Cuban told “The Draymond Green Show” podcast, in an April episode. “That was like a dream … I didn’t even negotiate, I was just like, ‘Yes, whatever.’”

Cuban’s current net worth is $5.4 billion, according to Forbes.

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