Mike Meldman started out a long way from the luxurious resort communities he's built since the early 1990s.

The Milwaukee native and Stanford graduate started out with plans for a career in law — but he told Insider that idea was scrapped when he "bombed the LSATs" and had to refocus his postgrad path.

A few months later he found himself dealing blackjack in Lake Tahoe, where he met a man who asked him if he'd like to make as much money as he wanted while working as little as he could. He said yes.

From there it was off to the races in real estate, where Meldman started working as a commercial broker until he started building his own property empire.

Today he's the chairman and CEO of Discovery Land Company, which he's led since founding the firm in 1994. The multimillion-dollar developer is behind some of the world's most exclusive neighborhoods. Meldman is also the cofounder of the trendy tequila brand Casamigos alongside two longtime pals: the Oscar-winning actor George Clooney and the nightlife mogul Rande Gerber, who is also the longtime husband of the model and actress Cindy Crawford.

Meldman, 62, has propelled Discovery from a single golf club to more than two dozen private enclaves from Idaho to the Caribbean that are now sought after by the world's wealthiest.

Even before the pandemic, his properties had already lured A-list residents and guests from Michael Jordan and Tom Brady to Reese Witherspoon and Bill Gates. But the 1% have moved in even greater numbers since last spring. Sales at Discovery — where home prices range from $2 million to $50 million — were more than $2 billion last year, according to the company. That's up from $1 billion in 2015.

"Everywhere we had available inventory, they sold it," Meldman said via phone from Discovery's Maui property. "People wanted the safety, the security, and the bubble we create."

Last month, Ben Affleck, a member of Meldman's Yellowstone Club in Montana along with the businessman Eric Schmidt and Justin Timberlake, reportedly rendezvoused with Jennifer Lopez in a mansion with a private chef in a much-watched rekindling of their early-2000s romance.

It's just the latest sign that Meldman has convinced the richest, most famous people in the world that they don't want to live (and vacation) on Park Avenue or in the Hollywood Hills but rather in remote, lush landscapes with spacious lots, outdoor activities, and amenities that outshine the Ritz-Carlton.

Take it from Craig Susser, the founder of the iconic Los Angeles eatery Craig's, who's been friends with Meldman for more than 20 years. The pair connected when Susser was waiting tables and bartending, long before launching Craig's.

Susser told Insider that Meldman is acutely attentive to detail and has sat him down for honest conversations about what was and wasn't working at Craig's, which is now beloved by celebrities. Over the years, Susser said those feedback-filled chats — informed by Meldman's own experiences gauging what the wealthy really want — were pivotal to his restaurant's growth.

"He's blazing a trail that doesn't really exist. Why not take advice from him?" Susser said. "He's the right mix of entrepreneur and heart."

With activities including archery ranges and wellness spas at Discovery properties, Meldman said he has a lot of fun at his projects, but they're designed with families in mind. But whether partying or not, he's just not the black-tie gala type.

"I pay not to go to those," he said. The real Meldman wears jeans and flip-flops to serve guests burgers from the backyard.

It helped business that the casually fancy atmosphere Meldman cultivates became coveted year-round during the pandemic.

The move toward social distancing and remote work turned several of Discovery's vacation communities into primary residences, Meldman said. Existing inventory sold out at virtually all properties in the months after the coronavirus hit the US, and demand drove Discovery home prices up 25%.

People who flocked to Yellowstone, for example, came from Boston, New York, Philadelphia, Los Angeles, and San Francisco, Meldman said, emphasizing that many relocated to far-flung locales, like Montana, because they felt safe. At his upstate New York property, Silo Ridge, the same phenomenon unfolded.

The company's vigilance in on-site COVID-19 testing and amenities like homeschooling and medical facilities, Meldman said, made living at Discovery all the more attractive to homebuyers looking to escape the crowds while still having every convenience close at hand. When residents, called members, arrive at a Discovery property, the staff handles everything, he said, so the experience can be stress free.

On-site dining facilities use organic farm-to-table produce, Meldman said, mimicking the Michelin-starred beach clubs of Italy's Amalfi coast. Jim Tripi, the director of culinary operations at Discovery's Austin and British Columbia locations, said he "fell in love" with the company for the freedom it gives its chefs to create dishes with producers and harvesters. But a clean diet wasn't always Meldman's style, Tripi recalled.

"He was eating classic American food like meatloaf when I first met him," Tripi said, but over the past decade or so he has become more health conscious. Now he's a fan of Tripi's plates of fish and turkey.

Members at all outposts enjoy vegetables and herbs grown on-site, along with vineyards and indigenous plant life.

Silo Ridge — located in Dutchess County, New York, about two hours north of Manhattan, where homes start at $2 million — "has an amazing garden," Meldman said.

It's fitting that Mindy Grossman, the CEO of WW International (formerly Weight Watchers), is a resident there. She and her husband have owned a home in nearby Millbrook for the past 23 years, but when they found Discovery, they couldn't help but buy a property.

"Silo is a gift," she said of the sprawling community with a bustling social life and leisure offerings including ice skating and golf — a sport her husband loves but she'd never played before joining. Now she's found herself driving and putting on the regular. She even recounted a time when she finished up on the green and a staffer stood waiting to cool her down with a shot of tequila and a wet towel.

Peter Whalen, the general manager of Discovery's Bahamas property, Baker's Bay Golf and Ocean Club, has been working for Meldman since he was 19. Now 37, he spoke to Insider about his career as passionately as if he'd only just finished his first day.

He remembers arriving at the Arizona club, called Mirabel, as a teenager during a long day of job hunting. He was welcomed in, he said, and spent hours shaking hands and interviewing while his then-girlfriend (now wife) waited in the car. He got the job.

"I love Mike Meldman more than my father, and I really love my father," he said. "He made me feel important, like I mattered — part of his family."

Whalen loves the company so much he named his 2-year-old daughter Baker after his Bahamian paradise.

"I had no training," Meldman said of his start in real estate. It was the early '80s, and he was working as a broker in the San Francisco Bay Area, negotiating leases on anything that came his way, like commercially zoned homes and properties for retirees. "I didn't even know what lease terms meant."

He signed deals for others for a few years before deciding that being a broker meant "you didn't have any real control over your destiny."

So he decided to strike out on his own and buy land.

He set his sights on a 300-acre lot in Portola Valley, California, near Stanford. In the mid-'80s, he lacked the money to buy it outright himself, so he financed the project through three of his friends.

Called Blue Oaks, it was the project that started it all, Meldman said, a well-worth-it handful that taught him everything he needed to know about the real-estate business. "It's basically where I got a Ph.D. in development," he said.

The property's picturesque location came with serious complications, from its proximity to the San Andreas fault to its stretch of nature preserve that couldn't be touched. "The land had every environmental constraint you could think of," Meldman said, reminiscing on the 18 years it took to build there after getting the proper approvals.

The key, he learned, was being mindful of the local landscape instead of working against it.

He honed his technique by working on new properties beyond California that proved beneficial for both the land and his bottom line. It was a win-win. In 1994, Meldman formally founded Discovery Land to keep expanding his network of private residential clubs.

In 1996, he debuted his first official project in Scottsdale, Arizona, a ritzy suburb of Phoenix.

The Estancia Club's golf course was named the best new private course anywhere by Golf Digest. Lots sold for $1 million, significantly higher than neighboring properties. But there were fewer of them — just 223 homesites on 640 acres.

But the smaller a golf club was, the better. It's more exclusive: A scarcity of homes makes each one more attractive — and more valuable.

"Most people think you have to have as much density as you can, but it doesn't work like that," Meldman said. "You're just scarring the land."

Meldman then crossed the Rockies to work on Yellowstone, now one of the most exclusive private ski resorts in the world. From there, he went on to develop a total of 25 Discovery properties worldwide.

Meldman's most publicized venture, though, is a liquid asset: small-batch tequila — thanks in part to Casamigos' famous cofounders Clooney and Gerber.

The trio have been friends for 20 years, Meldman said, and were at Discovery's El Dorado property in Cabo San Lucas, Mexico, where Clooney and Gerber have homes, when the idea was born.

"When you're in Cabo, you drink tequila," Meldman said, adding that the group wanted to create the drink just for themselves with no intent to sell. But their concoction quickly became well liked in their circle. Thirsty friends advised them to sell it publicly.

"Rande has bars, I have clubs, and George likes tequila," Meldman joked of the partnership, and he said they thought the drink would be successful, if only around their own clubs.

But when they created the company in 2013, they named what they thought was a modest sales goal for the year: 10,000 cases. That amount sold in a day, Meldman said.

By 2017, the trio had sold the brand to Diageo for a reported $1 billion — but it's still served at every Discovery property from Tennessee to Texas.

Meldman is always thinking ahead to future projects, but he doesn't rush into anything.

"Finding the right land in the right area can take a long time," he said. "There are a lot of things you need to make the project work, so you need to be more opportunistic than strategic."