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That company was Zscaler, which aimed to help companies transition away from outdated firewalls and into the cloud era.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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If you’re having trouble trusting your boss right now, you’re not alone.

A lot of managers have returned to their pre-Covid state: less visible and interactive than they were in 2020 and 2021, says Ben Granger, chief workplace psychologist and head of employee experience advisory services at Qualtrics.

Gone are the days of seeing managers in their homes on virtual meetings, bonding over shared pandemic experiences and chatting about families and lifestyles, he says.

“People got that champagne taste of communication. They had all that exposure to senior leadership and then that got scaled back,” Granger tells CNBC Make It. “So that decrease of communication could lead to different perceptions of, ‘Maybe I don’t feel as intimate of a relationship with that [manager] or that leadership group that I used to.’”

Sixty-seven percent of employees trusted and had confidence in their boss to make sound business decisions in May 2020, according to Qualtrics’ Global Resilience Survey. That number has since dwindled, Granger says.

Add on the waves of layoffs that occurred after the pandemic — some of which took place abruptly over email or Slack — and employees feel more stressed and less trusting than ever, says Granger.

The result: Bosses may find it difficult to effectively lead their organizations, and workers could quiet quit — or actually go.

To change this dynamic, bosses need to prioritize three “ingredients,” says Granger: competence, integrity and benevolence.

“When people detect those three things, they are far more likely to trust [their boss],” he says, adding: “Sometimes, you mess up a little bit and slip up, but if you’ve demonstrated that you care about the other person … people will give you grace.”

Employees want to work for someone with “good values, [who is] consistent to those values, and is looking out for the [best] interest of other people,” Granger notes.

Communication, listening and collaboration skills matter, too — for both bosses and employees. People with those skills can strengthen their workplace relationships, build trust and help foster a culture that people want to be part of, according to workplace culture expert Tom Gimbel.

“The more authentic you are, the more people are going to connect with you and enjoy your company,” Gimbel, the CEO of Chicago-based employment agency LaSalle Network, told Make It in April.

Try having informal meetings with your boss or manager every once in a while, recommend Andy Cohen and Diane Hoskins, co-CEOs of architecture firm Gensler.

“Many of Gensler’s younger employees will find 15 minutes on my calendar just to grab coffee and talk, whether it’s about work or life outside of work, our hobbies and interests,” Hoskins told Make It in February. “I can’t tell you how much I appreciate and enjoy those conversations.”

“In these kinds of conversations, most bosses are thinking, ‘What I can offer or say to help this person unlock some of their thinking about their careers, or try something new?’” she added. “These conversations can end up being really meaningful and productive.”

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This story is part of CNBC Make It’s Millennial Money series, which details how people around the world earn, spend and save their money.

After graduating from Syracuse University in 2017 and spending three years working corporate jobs in both advertising and marketing in New York City, Vienna Hintze wanted a change.

In 2020, the then 24-year-old struck out on her own and created her own digital marketing agency. In September 2022, she moved to Los Angeles while running her agency from her apartment, but still found herself longing for something more.

“I was kind of losing the why behind what I was doing,” she tells CNBC Make It. “I had moved out to L.A. and something just wasn’t working anymore. I had changed everything about my life except my agency.”

That restless feeling led to a talk with her therapist, who advised her to create a list of what she wanted from her ideal job. Hintze listed out that she wanted to work with her hands, be outside interacting with people and that she’d love to own an old pickup truck.

About a week later, she came up with the idea to start her own flower truck business, Main Street Flower Truck.

Since launching in August 2023, the business has brought in around $44,000 in revenue, plus an additional $4,500 in cash, Hintze estimates.

In May 2024, the now 29-year-old’s business brought in around $16,000 that month alone.

“If you’re living with your happiness, the money will follow,” she says.

Hintze grew up in Long Island, New York, and her father used to commute to his job as a firefighter in a pickup truck. Her mom held many different jobs but her love of gardening was a mainstay, Hintze says. So both the vehicle and the bouquets were familiar to her.

“Growing up, she had the entire backyard blossoming and blooming constantly,” Hintze says. “And some of my favorite memories with my dad was driving around in his little pickup truck.”

She decided to name her company after the street where she grew up, Main Street. But before she could move forward, she needed to obtain a key element: the vehicle.

Since she was still running her digital marketing agency full-time, she had only looked at, and taken test drives in, a few potential trucks. Eventually, by accident, she stumbled upon the perfect one.

When her parents came to visit her and her sister in Los Angeles last May, they decided to drive to Ojai, a small town in Ventura County about two hours outside of the city. While cruising along a back road, she spotted a bright green pickup truck with a for-sale sign in the window that looked similar to the one she drove while in high school.

“This felt very meant to be,” she says.

After the family pulled over to inspect the truck, Hintze wrote down the number on the for-sale sign. She called the owner that same day to ask if she could take it for a test drive. The seller agreed and told her that she had just replaced the engine and the transmission.

“I put my hands on the hood of the truck and just had this thought to the universe saying, ‘Please, if this is meant to be, please give me a sign.’”

The universe delivered: The owner told Hintze that the truck’s name is “Fiona.”

“My name is Vienna and every time I have introduced myself to someone in L.A., only in L.A., they’ve all asked me if I just said ‘Fiona’,” she says. “So that was my sign that, absolutely, I need to buy this truck.”

Two weeks later, she purchased Fiona for around $10,000 using money from her personal savings. Although she felt nervous about whether the flower truck would be successful, she was confident in her ability to run her own business.

“As scary as it was to pull the trigger on the flower truck, I already knew that I was the type of person to be all or nothing on whatever I do,” she says. “I was going to be 100% dedicated to it, and anything it takes to make it work I was going to definitely do.”

In August, Hintze began selling flowers from her pickup truck on the side while running her digital marketing agency. But as business began to pick up for her flower truck, clocking in for her marketing job got harder.

“It was like pulling teeth to get me to log in every day,” she says.

She knew she had a decision to make: Should she focus on running the flower truck full time, or her marketing agency? By February, she made the choice to pour all of her time and energy into growing her flower truck business.

Hintze decided to put her advertising and social media marketing skills to work for her own brand, and saw the results of her efforts pay off a few months later in April.

“I had some content start to go viral which felt incredible because, for the first time, I was marketing my own brand and it was the most authentic thing I had ever done,” she says.

That’s not to say Hintze hasn’t faced unexpected challenges. Since she spends thousands purchasing flowers, she used trial and error to figure out how much she should charge in order for her business to be profitable, for example.

″[At] the very first pop-up, I was selling huge bouquets for $7 and lot of that was just to prove to myself people will buy these bouquets, keep going,” she says. “I definitely lost money that day, but that’s OK.”

Her flower truck business brings in money in three ways, Hintze says: through pop-up events, corporate bookings and video shoots.

At pop-up events, she drives her truck full of freshly picked flowers that she’s arranged into bouquets to various locations around Los Angeles. She sells them for anywhere between $10 for a mini bouquet to up to $75 for larger custom arrangements made right on the spot.

“It’s always really fun to hear about whoever’s receiving the bouquet because then I customize it based on what they might like and their personality,” she says.

In between pop-ups, she books corporate events, parties and weddings. So far, she’s worked with a number of companies, including Lululemon, Free People and Universal Music Group.

For these events, the company or person can choose to rent the truck without flowers; rent the truck with flowers that can be sold to attendees; or rent the truck and pay for the flowers up-front to be given out to attendees for free. For these events, she charges based on how long they’re booking the truck and how many flowers they’d like to purchase.

Since flowers are seasonal, she earns more money in some months than others. Sales tend to fluctuate around holidays like Valentine’s Day and Mother’s Day, she says.

In general, Hintze aims to book at least three events each month, which she says generates enough money to cover her living expenses. However, she tries to keep her personal expenses low so that she doesn’t outspend her earnings.

In May, however, Hintze had the most bookings since she began her flower truck business. She booked 10 events and brought in a little over $16,000 in revenue.

“I’m hoping to keep that momentum up for the rest of the year,” she says.

Here’s a look at the Main Street Flower Truck’s expenses for May 2024:

Hintze’s largest expense is flowers, which totaled about $2,304 in May.

Before a pop-up or other type of event, she swings by her local flower district to choose which flowers looks the freshest and brightest, she says.

“I always gravitate toward wild flowers and things that look very whimsical and fairy-like,” she says. “I think it makes it the most fun-looking setup for the truck.”

She then brings those home and begins prepping them for sale by removing leaves, thorns and cutting stems. Finally, she arranges the flowers into bouquets and places them into various vessels, such as antique milk jugs and vintage buckets.

Her other expenses come from gas and maintaining her pickup truck. While the truck hasn’t needed any expensive repairs since she bought it, occasionally, she’s had to learn how to fix mechanical issues on the fly.

“One of the biggest issues having an older truck is the amount that it breaks down and having to randomly jump start it the morning of a pop-up when you’re set to be there at a certain time,” she says.

Moving forward, Hintze plans on continuing to grow Main Street Flower Truck and help companies and individuals bring their floral dreams to life. But she isn’t thinking about expanding her one-woman business yet.

“People ask me a lot if I’m going to franchise the truck and have a fleet of flower trucks, and I don’t see that being the plan for maybe ever, but definitely for a while,” she says. “My goal is to have the flower truck be as successful as it can as its own standalone, and see how far that can go.”

She hopes that the truck can be featured in TV shows or movies one day. “In the future, I’m hoping that Fiona will have her red carpet moment,” she says.

Hintze plans to continue to enjoying the freedom and work-life balance she’s gained by starting Main Street Flower Truck.

“I’m excited to keep exploring the creativity that I have that was pushed away for so long and really develop a routine out here that keeps my peace of mind at the forefront,” she says.

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When Kema Ward-Hopper uprooted her family — and career — to relocate from the U.S. to Costa Rica six years ago, she wasn’t sure what to expect.

She and her husband Nicholas quit their corporate jobs as a research analyst and mortgage broker, respectively, in Houston, Texas, to pursue new careers as entrepreneurs abroad. 

The couple signed a one-year lease on a house in the middle of the jungle on Costa Rica’s Nicoya Peninsula with their daughter Aaralyn not knowing “a single person who lived there” and “how long we’d be able to find work for,” Ward-Hopper, 42, recalls. 

But, she adds, the risk has paid off: Even though she had to leave a career she loved in the U.S., and is earning less than she did while working there, Ward-Hopper says she is “a lot happier” living and working in Costa Rica than she was in the U.S. 

Ward-Hopper now balances four part-time jobs: She’s a health and fitness coach, a Spanish teacher, a host for wellness retreats and, most recently, an author. She self-published her first book, “For my Beloveds: An End-of-life Journal for Guidance & Wisdom,” in September 2023.

“I work 25 hours a week now,” she says. “A heavy week is about 30 hours a week, but that is rare and happens about once a month.”

Last year, Ward-Hopper’s different income streams earned her about $10,500, according to financial documents reviewed by CNBC Make It. 

Meanwhile, her husband Nicholas, 43, runs his own remote logistics business, earning him about $19,500 in 2023.

“Living here has allowed me to explore my passions so that my methods of earning income don’t feel like a job, it just feels like I’m getting to do the things that I love to do, which is to be of service to others,” Ward-Hopper says. “We make less money, but we’re still living pretty comfortably … our money definitely goes further here than in the U.S.” 

Last year, the Ward-Hoppers moved to a three-bedroom, two-and-a-half-bath house in Nicoya. Their biggest expense is rent and utilities, which totals about $628 per month.

In addition to the lower cost of living, Ward-Hopper says she’s found a “more fulfilling, less stressful” career in Costa Rica than in the U.S. because of the country’s relaxed, “family-first” work culture. 

“It’s common to see children in businesses where their parents work, if they’re off from school and don’t have another child care provider, and bosses aren’t so rigid that if you need to take time off from work or step away for a minute if your child is sick or needs something, you’re going to get in trouble,” she says. “As a working parent with young children, that cuts out a lot of stress.”

Ward-Hopper’s son, Nico, was born in Costa Rica in 2020. 

Costa Ricans also value a healthy work-life balance, she adds. The country has a shorter workweek than many other nations, allowing ample time for hobbies, rest and spending quality time with loved ones. 

Many businesses in her neighborhood don’t open until 9 a.m. or later. “You can’t visit a coffee shop and get your morning latte at 7 a.m. like you’re able to do in the U.S.,” she says. “A lot of places are closed on Sundays, too, and holidays, which I’d think helps their employees not burn out.”

Costa Rica is one of the happiest countries in the world, ranking 12th on the World Happiness Report’s 2024 list. 

The Nicoya Peninsula, where the Ward-Hoppers live, is one of the five original Blue Zones. Blue Zones are regions in the world with some of the longest-living people and highest life expectancies, according to longevity researcher Dan Buettner.

Some of the factors that make Nicoya a Blue Zone, Buettner discovered, are the Nicoyans’ diet, which includes fresh fruit, vegetables and whole grains as well as their focus on family and community.

Ward-Hopper would add the Costa Ricans’ attitude toward work to that list. “Work is a lesser part of conversations and how people identify themselves here than in the U.S.,” she says. “That mindset makes it easier to have a fuller, more joyful life outside of what happens at our jobs, which is so often out of our control.”

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At 104 years old, Virginia Oliver plans to set sail and continue doing the job she’s loved for over 90 years: catching lobsters.

Oliver, known in Maine as the “Lobster Lady,” renewed her commercial lobster license just in time for lobster-catching season, according to TODAY.com.

“I’ve been lobstering on and off for 91 years,” Oliver said in the mini documentary “Conversations with The Lobster Lady.” The short film was shot in 2019 by Wayne Gray and Dale Schierholt.

Since then, Oliver’s continued lobstering. “I like to do it,” she said.

During good weather days in peak season, which spans from June to October, Oliver goes out on her boat “Virginia,” named after herself, to catch lobsters with her 81-year-old son, Maxwell. The pair make the trip three times a week.

“I don’t want to go five [days],” Oliver said. “That’s a regular job and I don’t need that.”

But Oliver does stick to a daily routine of waking up earlier than most people. “That’s my daily thing, a quarter to 5 [a.m.] in the morning I get up,” she said in the film. “But if we’re going out to haul, I usually get up at a quarter to 3 [a.m.]”

Oliver preps the bait bags for the lobster traps, and after her son hauls the lobsters, she measures them to make sure they’re large enough. If they don’t meet the size requirements, she tosses them back into the water.

She even gets dolled up before her trips to the boat. “I always wear earrings to haul,” Oliver said while laughing in the film. “I always wear my lipstick and things, just like I was going to go up the street somewhere.”

When Oliver was just eight years old, she went lobstering for the first time with her father who owned a store and was a lobster dealer. Her job was to weigh the lobsters and pump the gas for the boat at the time.

She continued lobstering with her late husband, even though most women didn’t do the job.

“When I started out with lobstering, no women ever went. Now there’s quite a few women,” Oliver said. “That was just the way I lived. I don’t worry about somebody else and what they’re going to do. I do what I want to do, but I’m really independent.”

When asked what her secret is for living to 100, Oliver said, “You’ve gotta keep living, you gotta keep working. It’s not easy.”

A lot of Oliver’s lifestyle choices also set her up for greatness; she stays active, sticks to a schedule, has never smoked and doesn’t enjoy alcohol, according to TODAY.com.

Oliver also spends a lot of time near water and grew up living on several islands off the coast of Maine, including Andrews Island, the Neck of Andrews Island, Dix Island Harbor and more.

Nearly all of the world’s blue zones, areas with the longest-living communities, are near water. Living near water “seems to make us happier,” longevity expert Dan Buettner told CNBC Make It in June.

And when it comes to doing what she loves, Oliver never plans to stop lobstering.

“I’m not going to retire,” she told TODAY.com. “I’m going to do this till I die.”

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