The Secret Retreats That Have CEOs, VIPs and Billionaires Jockeying for Invites
Ultra exclusive conferences are booming. In Sicily, Aspen and Stockholm, Elon Musk and Margot Robbie mingle with bank leaders and media moguls. ‘There’s always another VIP level.’
7 min
The crowd at the St. Regis hotel in Aspen, Colo., on one weekend last fall was handpicked, and if you had to ask to be invited, you wouldn’t be on the list. Guests, including Ron Howard, Karlie Kloss and Goldman Sachs Chief Executive David Solomon , were given Barbour vests, offered a walk-and-talk with Olympic running champion Allyson Felix, take a golf clinic with professional golfer Michael Block or bike with Gen. David Petraeus. The bike route climbs more than 2,000 feet starting from an 8,500-foot elevation.
One morning, a man in his 50s in a dark sweater was speaking to a group, while his security staff stood off to one side, an attendee recalled. He was Elon Musk , talking with the author of his newly released biography, Walter Isaacson , in an off-the-record conversation moderated by CBS anchor Gayle King. It was one of the hottest tickets on a packed agenda at the ultra exclusive and secretive conference known as the Weekend, co-hosted by Endeavor CEO Ari Emanuel and other business, tech and finance leaders.
Musk and others attending the Weekend, and gatherings like it, get to exist for a brief time in a buffered safe space where CEOs, celebrities, athletes and political leaders know that no one will tweet a photo of them working out or waiting in line for Champagne. They are invitation-only, and attendees often arrive via private jet and tinted-out SUVs. The talks are off the record. No one who goes cares what it costs.
“There aren’t that many places for these people to have these conversations,” said Salesforce CEO Marc Benioff , who hosts his own intimately curated gatherings of business leaders and has attended other people’s as well. (In the parlor game of invitations, his dinners can feel like a rung up from anything called a conference.)
It has been 40-plus years since Allen & Co. put on its first so-called summer camp for the billionaire set in Sun Valley, Idaho, now an executive’s rite of passage, and more and smaller and intimate ultra-VIP conferences are exploding on the scene—from media mogul and venture investor Jeffrey Katzenberg ’s in Montecito, Calif., to restaurateur Danny Meyer’s in Tuscany. There are new ones popping up nearly every month.
Helping fuel the desire for invitations is the lore of what Sun Valley has spawned: Sam Altman connected with his most important investor, Microsoft CEO Satya Nadella , at Allen & Co.’s annual July conference; Disney finance chief Christine McCarthy and CEO Bob Iger got some facetime over lunch at the same event a different year, a few months before Disney’s board ousted CEO Bob Chapek and reinstated Iger; Jeff Bezos ’ purchase of the Washington Post stems back to Sun Valley moments.
The newer events make the World Economic Forum’s Davos—with its pop-up media spaces and Getty photographers scattered about—look like a Vegas trade expo. There is a summer excursion to Stockholm for the humbly named Brilliant Minds gathering hosted by Spotify CEO Daniel Ek ’s foundation, which some attendees consider the most fun in the elite event lineup.
The Weekend in Aspen is in September, pre-ski season, but invitees to boutique bank LionTree’s conference called MediaSlopes head to Deer Valley, in Park City, Utah, in March and skiing is abundant in Davos in January. Google’s annual VIP camp has been held in Sicily at a resort with four outdoor thalassotherapy pools. The Brilliant Minds gathering included a cruise around Stockholm’s archipelago, and MediaSlopes offered high-intensity exercise classes taught by the CEO of video game company Take-Two, Strauss Zelnick , who prides himself on his physique. There is usually a concert—the Killers and John Mayer have played MediaSlopes (anyone who goes just calls it Slopes).
This account is based on interviews with people who attended the gatherings, event materials and social-media posts.
Benioff, who also owns Time, has attended the Weekend and Allen & Co.’s Sun Valley event, but says he “can’t do them all” and loves to host his own, even more exclusive events.
At Benioff’s gatherings, there is usually “a small group of somewhere between 25 and 35 people around a table,” he said, adding that he’s hired people he has met at such events. At a recent one, restaurateur Eric Ripert of Le Bernardin prepared the food and briefly spoke with attendees. Comedian Jerry Seinfeld performed and so has Japanese rock star and fashion designer Yoshiki. The gatherings have taken place in New York, Japan, Australia, France and the U.K .
Always a celebrity chef, he said. “We actually end up with a regular set of celebrities and entertainment who are our favourites, and there’s just people we feel very connected to,” Benioff said. “There’s the right level of quality.”
Who’s invited, and where?
At last year’s Slopes, which attendees call the cool Sun Valley, Margot Robbie swapped her Barbie pink for black to be jointly interviewed with Mattel CEO Ynon Kreiz by LionTree Chairman and CEO Aryeh Bourkoff. Bourkoff has been one of the most prolific dealmakers in media, including as a lead banker in AT&T ’s 2022 $43 billion spinoff of Warner Media to Discovery. This year, Lionel Richie performed.
The competitive juices flow, too. Univision CEO Wade Davis has won annual slalom races. And there is a game-show style quiz focused on trends in tech, telecom and media. This year included the question: Who is the biggest streamer? (Answer: YouTube)
The Verdura resort, with “230 hectares of sun-kissed Mediterranean coastline” in southern Sicily, has been home base for what’s known as Google camp in recent years—the tech giant’s annual, invite-only retreat.
Google camp’s theme for 2024, according to a bare-bones website, is artificial intelligence’s role in scientific breakthroughs and addressing global challenges. The site doesn’t say if this summer’s camp will also be in Sicily.
Alicia Keys performed one year on a stage set against ancient ruins. YouTube star Lilly Singh snapped a photo amid the ruins with actress Charlize Theron. “We’re going to change the world. @charlizeafrica #GenEndIt #GirlLove ,” @Lilly posted on Instagram. Google owns YouTube.
Google said the majority of guests are customers and partners of Google and discussion sessions make up most of camp. It wouldn’t confirm names.
Jolie Hunt , who advises CEOs among others as founder of marketing and communications firm Hunt & Gather, said she increasingly fields calls from executives and powerful people about which VIP conferences are worth their time, alongside how to get a Birkin bag and book the best driver for Davos.
Part of building the allure of the events is the selective invite lists, with nobody there to pitch their agenda out of turn, some attendees said. Organizers manage the guest list, looking for buzz and mix, and asking for an invite isn’t a good look.
Midnight sun in Sweden
If Sicily didn’t make the calendar, summer’s lineup also includes Stockholm’s Brilliant Minds gathering—the brainchild of Spotify CEO Ek and Swedish entrepreneur Ash Pournouri, who hosted the first one in 2015 before establishing a foundation by the same name three years later.
Actor Jared Leto, Reddit co-founder and startup investor Alexis Ohanian and VaynerMedia CEO Gary Vaynerchuk were among 2022 attendees who boarded a boat for a tour around Stockholm’s archipelago that included a stop on one of the islands for dinner. Their cocktails were garnished with slices of fresh watermelon, and they took in a private concert by Florence & the Machine.
The intention is to bring together creative and influential figures with a goal of creating an impact, a representative for the organisation said. Brilliant Minds’ theme this year is “Discovery,” and so far, Harvard Business School’s Debora Spar , self-help personality Jay Shetty and Stockholm School of Economics Wellbeing, Welfare and Happiness professor Micael Dahlen are expected to present. Past attendees include former President Obama, filmmaker Darren Aronofsky, Snap’s Evan Spiegel , NBA All-Star Draymond Green and Malala Yousafzai.
Anu Duggal, founding partner of the Female Founders Fund who has attended Brilliant Minds and interviewed Trevor Noah and Yousafzai there, said the formal programming runs from 1 p.m. to 5 p.m., adding that the gathering emphasises bringing people together through fun experiences. “They take advantage of the natural beauty of Sweden,” noting the late sunsets at that time of year. Her firm invested in a startup that took part in a pitch competition where she served as a judge.
Stagecraft opportunities
Sometimes attending Allen & Co.’s Sun Valley conference is about making a very public statement from a very secluded place. Bill Gates used the gathering in 2021 as a soft launch for his return to public after the announcement of his divorce from longtime wife Melinda French Gates . Gates was spotted walking and chatting with Evan Greenberg , CEO of insurance giant Chubb . Gates wore khakis and a navy sweater, and both business leaders had white name tags.
In the summer of 2021, as reports emerged of a deteriorating partnership between Facebook ’s CEO Mark Zuckerberg and then-Chief Operating Officer Sheryl Sandberg , the two appeared in photos strolling together along the lush grounds. Sandberg, in a T-shirt with the words “just love” scrawled in cursive, smiled as Zuckerberg, in a navy hoodie, looked at her, also smiling.
Marc Ganis, founder and president of the sports-industry consulting firm Sportscorp, said he has been attending more invite-only retreats or gatherings than ever before, estimating he attends three or four a year in addition to industry-specific events.
“This is where the ideas for business can be developed,” said Ganis. “What makes one better than the other is who actually attends.”
A relative newcomer is an invite-only conference for sports executives put on by Bruin Capital and Penske Media’s Sportico held on Kiawah Island in South Carolina. Bruin CEO George Pyne and Penske Media CEO Jay Penske bring together about 150 attendees including billionaires, commissioners, team owners and investors to play golf and talk about more than sports. Former New Jersey Gov. Chris Christie and the former prime ministers of New Zealand and Finland, Jacinda Ardern and Sanna Marin , spoke this year—the event’s third year—as did former Pimco CEO Mohamed El-Erian .
The world’s biggest advertising agency, WPP, calls Stream, its invite-only event for about 300 invitees, an “unconference.” Attendees, this year in Santa Barbara, Calif., determine discussion topics, which have included “Should we teach robots how to lie?” Its website describes “two days of off-record debate alongside dancing robots; slam poetry; drone races; a space launch” and more.
WPP CEO Mark Read says the event is unique for its lack of PowerPoint slides and that the idea is to foster chance meetings among people in the business. In 2023, Linda Yaccarino spoke after Musk at Stream—a few days before she resigned from NBCUniversal and Musk announced her as X’s new CEO. Also last year, Paris Hilton ran a breakout group, said Read. “We had one famous music executive who turned up and couldn’t deal with the lack of structure and left,” he said.
The surge in exclusive events comes as the World Economic Forum’s conference, held in January in Davos, Switzerland, has ballooned over the past several years. In 2024, more than 800 CEOs and chairs attended Davos, in addition to government leaders and others, according to a WEF spokesperson.
Musk has knocked Davos, tweeting in December 2022 : “My reason for declining the Davos invitation was not because I thought they were engaged in diabolical scheming, but because it sounded boring af lol.” Organizers for the World Economic Forum later said Musk was not among the invited.
But at the Weekend in 2022 Musk got personal. During a conversation with Carlyle Co-Chairman David Rubenstein as Musk’s acquisition of Twitter was pending, Musk said he lost 25 pounds, attendees recounted. He said—in a self-deprecating way—that topless photos of him on a yacht from the summer that circulated around the internet motivated him to lose weight, which he said he did through intermittent fasting.
“It’s craziest when you’re around people like this—there’s always another Champagne room, always another VIP level,” one attendee said, and quipped: “Even the CEO of Goldman Sachs isn’t treated like a VIP. That’s a third-tier guest.”
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From early financial mistakes to hard-earned habits, five high-performing leaders share how they spend, invest and think about wealth.
9 min
Five minutes doesn’t sound like much. But it’s enough time to tell whether someone really understands money or just talks about it. Because once the gloss is stripped away, what’s left is instinct. The early mistakes. The bad calls. The quiet pivots that no one brags about but shape everything that follows. Making money is one thing. Living with it, and not mishandling it, is another. Here, five executives talk about what they got wrong, what they’ve learned, and how they now actually spend, invest and think about wealth.
Andrew Raso: Founder, Online Marketing Gurus
Self-made millionaire Andrew Raso grew up in an ethnic household with a father in construction. Investing was not a priority, he recalls.
The co-founder and CEO of Online Marketing Gurus, a digital marketing platform that generated more than $30 million in revenue in the 204/25 financial year, admits he’s had to learn about handling money as his wealth has grown.
“If I had my time again, I would change my spending habits and would probably be a lot more wealthy as a result,” the Sydneysider tells Kanebridge Quarterly.
Raso, in his mid-30s, says that his biggest lessons have come from his losses.
Buying the wrong property and copping the losses upon sale. Feeling FOMO when buying crypto and making a purchase that lost money.
“I’ve learned a lot from the errors that I’ve made,” he says.
Raso admits that he gets more of a thrill out of working than watching money hit his bank account.
“I’ve had the cars, I’ve had the property, I’ve had the watches. Once you’ve had them, they’re not that exciting, but the process of earning money is pretty cool.”
What he won’t forget is being $45 million in property debt a few years ago.
“I’d never want to be in that position again,” he says.
“My investing strategy is a lot safer these days. I’m very cautious. I’d prefer to invest in things that don’t take as long to be realised so my family can be financially secure.
“Once you have a house paid off and a few investments, it then becomes about enjoying your money, rather than hoarding it. Giving back gives me a much bigger kick than spending these days.”
Daniel Wessels: CEO, Jacaranda Finance
Fintech founder Daniel Wessels knows only too well that money remains a taboo topic in Australia with many people.
He points to consumer surveys that reveal people are more likely to talk about their sex life with friends than their finances.
It’s a major concern for the man who founded Jacaranda Finance in 2013, which has helped countless people lift their credit scores and get their finances back on track.
“If people aren’t learning money habits at school and they aren’t discussing it with their friends, learning new strategies and better habits is difficult,” says Wessels, who is based in Brisbane.
He wants to see more people take the time to proactively understand where and why they are spending money.
“Everyone needs to have a financial strategy and a plan to measure if it’s working,” he says.
The father of two young children admits his week can be pretty fast-paced. Pomodoro clocks, sleep optimisation techniques and saying ‘no’ keep him on task during the week.
“I used to think I was fairly decent at managing time, but the whole game changed when we had kids,” he says.
“Now, I’ve got to get out of the house at a certain time and leave the office at a certain time for daycare pickup. I’ve got to be really specific about my tasks to maximise my week.”
Before he had a family, he loved heading out to one of the trendy new restaurants popping up in Brisbane.
But that happens less these days. He’s saving to build his forever home but admits that price rises have resulted in rising costs.
“It’s such a big project with so many variables that change quickly,” he says.
These days, Wessels likes to optimise his professional and personal life. “With only a finite amount of money, time and energy, you’ve got to be really good at deciding what you want to be good at,” he says.
He calls this ruthless prioritisation. He has a very specific focus on activities that prioritise health and wealth, adding experiences into the mix more recently. This has meant the addition of micro-holidays to his annual calendar.
Wessels works with a couple of financial advisers. That said, he also does his own due diligence before agreeing to investments.
“One likes private equity investments that pay cash every month and another prefers to focus on the NASDAQ Stock Exchange for buying shares because he’s bullish about that.” he says. “They’re each experts and really good at what they do.”
Jim Penman: CEO, Jim’s Group
He may have invested a lifetime building a franchise juggernaut that is reportedly a $1 billion a year empire, but Jim Penman insists he’s a frugal guy who prefers to spend time planting a tree in his garden than contemplating his wealth.
What started out as Jim’s Mowing back in 1989 became Jim’s Group. Today, there are 5,700 franchisees across Australia and New Zealand in the business that has become ubiquitous for being the local handyman company that households could rely on.
He may have built a successful business empire, but the Melburnian insists he’s stingy when it comes to money.
“I wear my clothes even today until they wear out. I’ve always had a very lean and mean attitude. I live a simple life. My personal needs are very modest and my finances are simple,” he says. Jim reveals he’s usually in his garden these days and rarely eats out or takes holidays.
He is also running for state politics in the November Victorian election.
“I’m not particularly money focused. I could tweak the franchise contract to put more fees in and double my profitability, but that’s not my goal or my aim. To be honest, I often make decisions that go against my financial self-interest,” he says.
Jim purchased his first brand new car three years ago, opting for an electric Volvo.
“Being rich is not my aim and it never has been. People think I’m a lot richer than I am. They think I’m a billionaire, which is kind of ridiculous,” he says.
In fact, he insists he carries debt, which is common for anyone in business. “If I wanted, I could pay it off in 18 months.”
While his competitors were spending on fancy office space, Penman was running his franchise from his basement, keeping business costs low. “When I started out, I didn’t have any concept of how big this business could be. But there has never been a plan to grow franchisee numbers.
“Our attrition rate is far more important, and how to reduce complaint rates and drive more enquiries through new software.”
He believes people these days worry too much about impressing others, which leads to spending on superficial things.
“I would rather than offer people advice on how to be happy, rather than how to become rich. It’s important to have a good income so you can support yourself. But life is more about purpose.”
Jim doesn’t bother with stocks or bonds. He only invests in his own business. “My rate of return on my business is substantial. I could buy back a regional franchise when they come on the market and get a 20-25 per cent annual rate of return, plus capital gains. There’s nothing like that available in the investment space.”
Nicola Beswick: Founder, White Rabbit Advisory
Rabbit Advisory founder.
A clothing allowance provided by her parents and then a part-time job during high school was the first taste of financial freedom for Nicola Beswick.
She quickly became a spender rather than saver, but she’s changed her tune over the years.
The founder of financial advice firm White Rabbit Advisory left behind a successful career in intellectual property law a year ago to become a financial adviser because she realised the potential that financial education could have on someone’s life.
Her journey began after coming across the book Rich Dad Poor Dad some years ago, which opened her eyes to the power that money could have on her life. This marked a time when she became serious about her finances.
“Financial education and investing over time can have a huge impact on a person, and that book got me thinking about money and financial education in the first place,” she says.
Nicola says years ago, her father was diagnosed with multiple sclerosis. When dealing with the devastating news and an uncertain future, her father discovered he was eligible to receive an income protection payout.
“This was the stone that rippled his pond and mine. A new complex world of finance opened up and I discovered my calling – helping people plan for a financially secure future.”
She hasn’t looked back. “Commercial law was very transactional. I don’t regret quitting at all. I’m much happier now helping people get their finances in order. Financial planning helps people change their lives. That was a really big driver for me.”
The Melburnian admits she’s learned plenty of lessons along the way as she embarks on the process of building wealth. She uses superannuation as an investment vehicle, favouring its tax advantages.
“I also built a nest egg outside of super, because you never know when the rules will change,” she says.
She prefers to set a financial goal and save up for something specific over time than rush out and make a purchase.
“It’s a really powerful thing to wait before making a purchase,” she says.
Her current financial goals involve renovating her heritage-listed home. “We will keep the façade and gut it to rebuild. That’s a major expense for us on the horizon.”
While holidays are rare, she will spend on overseas trips on occasion. “I’m terrible at taking time off. I’m always working.”
Sam Riley: CEO, Drova
Sam Riley was in his 20s when he set out to amass enough money to be able to retire by the age of 40 if he wanted to.
“The goal was always to be doing something by 40 that kept me engaged enough that I didn’t actually want to retire because I was happy,” he says.
An entrepreneur at heart, Sam started a juice and espresso bar when he was 21, which didn’t work out. His next venture was a technology business, Ansarada, an ASX-listed company he ultimately sold nearly two years ago for $250 million.
The sale set him up for life, but he’s not one to rest on his laurels, launching into the complex world of artificial ntelligence with his next technology play, a company called Drova.
The technology startup simplifies risk, compliance and resilience for small businesses. Sam believes it’s got potential to become a tech juggernaut in time.
Having early financial success has meant he has the luxury of slow mornings and working in short bursts throughout the day, problem solving, experimenting with what works and figuring out how to harness AI.
“I favour a more sustainable approach to working these days. More frequent breaks. Making sure not to deteriorate my capacity,” he says.
It was a hard slog. He admits he touched the fringes of serious burnout when he was younger, which he works hard to avoid these days.
“Every business venture has exposed a gap in my skills that I’ve worked to close. Whether that’s marketing or managing people, closing those gaps along the way is how you get more effective at generating wealth,” he says.
The secret to his success has been finding ways to bolster value in the corporate world, finding ways to bring more to the table. Sam admits he spends too much money on travel, food and niche vinyl audio equipment, like turntables. He prefers to invest in experiences rather than things.
But it can get expensive. Like a recent trip to Antarctica to stay in a lodge for a week. “The thing is I didn’t like having these experiences on my own, so I have to bring family or other people and then pay for them.”
Sam describes his investment portfolio as balanced. While he continues to invest in entrepreneurial ventures, he admits he has a safe foundational platform to his investment approach.
“Over the years, I’ve added a lot more dividend stocks and protective assets like gold and silver, and some index funds.
“When I was younger, I didn’t appreciate the value of being safe and boring in the investment world.”
He says a lot of his investments used to be leading edge and visionary. “Some of them work, and some of them don’t. I didn’t really have much balance in my portfolio. I still invest in entrepreneurial things, but am much more conscious of taking a more even-handed approach,” he says.
This article appeared in the Winter 26 issue of Kanebridge Quarterly, which you can buy here.
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