What is it like to buy a private jet and then lose so much money that you have to sell it? Or take a $1 million European vacation to celebrate a deal closing? I asked the people who have lived it.
I crisscrossed the country to sit down with millionaires and billionaires for The WSJ Money Interview, hearing about how the ultrasuccessful make, spend and grow their money. Through eight flights, 14 days on the road and countless hours in interviews and in the editing room, I got a peek at the moments -- both stomach-churning and euphoric -- that shaped them.
I witnessed off-camera interactions with assistants, friends and family. We also had some fun. I quizzed them on whether their fortunes, which ranged from tens of millions of dollars to billions, were driven by luck or skill.
Here's what I learned.
Got fired? No problem.
If you've been fired from a job, you're in good company.
Bill Perkins, the founder of Skylar Capital Management, was fired by his friend, the former energy trader John Arnold, for his wild trading style.
"John was like, 'This is just not going to work. You're just too volatile. You're too crazy,' " Perkins told me.
He ended up trading with his own money and was later rehired by Arnold, earning more than $1 billion for the firm. Perkins was candid about tough moments, including what it was like to be hit with giant margin calls on positions, something traders avoid discussing.
The billionaire entrepreneur Fernando De Leon says he was shown the door as an analyst at Goldman Sachs, and took it as a sign that he wasn't meant to answer to anyone. He moved back home to Texas and started investing in real estate, laying the groundwork for the holding company Leon Capital Group.
Private-jet mogul Kenn Ricci was pushed out of the company that he founded, Flight Options, in his 40s. The behemoth Raytheon had invested in it and bought him out. "It was the worst day of my life," Ricci told me.
He didn't sulk for long. He took proceeds of the deal, around $20 million, and started the investment firm Directional Aviation, which made him a billionaire years later. The groundwork he laid back then helped him pounce on a surge in private travel during the pandemic.
Bold bets
Several of our guests had an eye for what Vinod Khosla, the founder of Khosla Ventures, calls "option-value investing," and the stomach to withstand the turbulence associated with it.
The options market can be a venue for boom or bust bets, and traders lay down tiny sums that can pay out enormously if their bets prove correct. Khosla's investment in the technology company Juniper Networks earned him a return of more than 2,000 times his initial investment.
Allison Ellsworth and her husband, founders of soda brand Poppi, maxed out their credit cards to build the company, wagering a sale could reap a bigger payday. They became centimillionaires after Poppi was sold to PepsiCo for nearly $2 billion.
Several said it was important to have equity in your projects.
David Grutman, the Miami-based hospitality maven, emphasizes having a sizable stake in businesses he is involved with.
It doesn't have to be a sexy business. Sometimes boring businesses are the most lucrative, something I learned from De Leon's bets on med spas and real estate.
Family chats
"So we're rich?" one of Ellsworth's kids asked her after the sale. She didn't shy away from talking money with her young kids after the payday, and had them dabble with stock investing. She and her husband hold money meetings, and she shared how they think about structuring a family office.
These talks can be thorny.
Ricci went viral for taking viewers behind the closed doors of his family's quarterly money meetings, all the way down to agendas. I stole some tidbits for my quarterly money meeting with my husband (read about that here).
And both Ricci and Perkins say they are passing down money younger than most people, while their kids can enjoy it.
Design thinking
There's a stereotype that some people are good with numbers, while others are creative. Some of the most successful entrepreneurs I sat down with were both.
Baiju Bhatt, the co-founder of Robinhood who recently launched space company Cowboy Space, built a car in his garage during the Covid-19 pandemic and was behind Robinhood's app design. He said designing beautiful cars has a lot in common with creating intuitive mobile apps. Plus, having a hobby helps.
"Having a creative outlet outside of work generally supercharges creativity at work," Bhatt said.
Khosla attributed his success to "design thinking." When I visited his Menlo Park, Calif., office, I learned he designed it, all the way down to restroom paper towel dispensers, which he stayed up until 2 a.m. some nights perfecting.
The $1 million vacation
Turns out, " private-jet money" really is the new marker of wealth for many Americans.
Ellsworth's first splurge was a roughly $1 million family vacation to Europe. Ricci's annual vacation budget is around $800,000. And Perkins said his summer trips can cost around $1 million, though one of his favorite activities, a bike tour, costs almost nothing.
Watch our full series here. Write to the host at gunjan.banerji@wsj.com and follow her here.