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“Bond King” Bill Gross reflects on life, love & retirement


Photos by Mary Hurlbut and Katie Beverley

Two and a half years ago, at the suggestion of a mutual friend, Bill Gross paid Amy Schwartz a call. Bill was newly divorced and living in Laguna Beach. Amy, a former tennis pro, lived in Santa Monica. The two exchanged emails and Bill suggested that if Amy were ever in Newport, they should have a drink. A few days passed before Amy wrote Bill a “nice little note” saying, “Thanks for the invitation. But if you’re ever in Santa Monica, let’s have that drink.” 

Bill had met his match. He drove to Santa Monica the next day. And the day after that. He was hooked.

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Photo by Katie Beverley 

Bill Gross and Amy Schwartz at Amy’s 50th birthday soiree last month

Bill Gross is not a new name in town, but his life looks remarkably different than it did a few years ago. At one point, the co-founder, former chief investment officer, and managing director of Pacific Investment Management Company (PIMCO) controlled nearly $2 trillion primarily in debt dollars – more fixed income securities than anyone else in the world. Morningstar reported in 2010, “No other fund manager made more money for people than Bill Gross.” 

Well known in the financial world as the “Bond King,” Bill is also one of Orange County’s most notable philanthropists, having donated more than $800 million to various charities over the years. And as a renowned philatelist, he’s slowly been parting with the largest privately held collection of U.S. stamps in the world. Proceeds from auctions of his collection exceed $40 million from 2007 to date and go straight to charity or his charitable foundation.

For a man who never stopped working, Bill is embracing retirement remarkably well. He retired from Janus Henderson Investors in March of this year. Today, the Bond King is responsible solely for his own assets, which Forbes pegs at $1.5 billion. 

But alongside all these mind-bending numbers and impressive statistics is perhaps the less recognized – though no less significant – nuanced private life he leads, and the woman with whom he shares it. 

Finding common ground in their quest for fame

Despite different childhood experiences, Bill and Amy share a few fundamentals – a passion for music (they’ve constructed a three-and-a-half-hour favorite playlist, consisting mostly of 80s music); an addiction to golf (they spend at least three hours, and upwards of six, on the greens each day); and an unquenchable thirst for fame. 

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Photo by Mary Hurlbut

Amy and Bill pose before a painting of their vacation in Bora Bora

For Amy, the desire for notoriety began at age eight, when she set her sights on professional tennis. One of the first resident players in Nick Bollettieri’s legendary clinic (alongside Andre Agassi), Nick promised her stardom and he delivered. Amy played professional tennis for nearly 10 years, dominating over Arantxa Sanchez Vicario in the 1986 Brazilian Open. She also made it to the second round in women’s singles in the 1988 Australian Open. Later she served as tennis consultant for the movie Bridesmaids and taught the game for many years. 

Bill didn’t articulate his desire for fame until his 20s. After receiving his MBA from UCLA’s Anderson School of Management and beginning his career at Pacific Mutual, he announced his intentions. “I’m going to be the best bond manager in the world,” he told his parents. If only his parents had understood what being a bond manager meant.

“Not to get all Freudian on you, but the need to be famous is the need to be loved,” Bill says. “Amy and I are both fame-driven. And it’s really about a desire to be loved.”

Inside the King’s mind

For four decades, Bill Gross penned some of the wittiest, wisest, and most insightful monthly forecasts to investors. Known as his “Investment Outlooks,” they were stunningly accurate predictors of global markets. But they also offered insights into life itself. Bill often reflected on human nature, our rapid submission to technology, our innate pull towards tribalism and warfare, and the universal fear of death. He wrote about foxes and hedgehogs and Easter egg hunts. The commentaries were resonant, reflective, and philosophical. Warren Buffet said of them, “The prose is lively, the logic flawless, and his insights valuable.” Not what one might expect from a man so seemingly single-minded and focused on economic success. 

“My best ones, in my opinion, were mentally framed during quiet moments in a shower or after a hard workout at the gym when endorphins open the brain to subconscious thoughts and feelings,” he says. “They are as much of an autobiography as I could have written, but framed in a monthly series of essays, compiled over four decades that show a maturation or perhaps a molting of my life’s philosophy. They represent who I was, who I am, and who I expect to become.” 

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Photo by Mary Hurlbut

Bill Gross at home in Rockledge by the Sea

There is something humane about his writing that belies the purely methodical and disciplined image of him often portrayed in the press. Now, seven months into retirement and once again smitten by love, it might appear that a more gentle Bill Gross has emerged. He’s shed his signature Hermes ties in favor of snazzy socks. He spends his afternoons at the driving range instead of behind his Bloomberg terminal, which he donated to the Smithsonian in 2015. He prefers the comforts of home to the rigors of an office.

Maybe Amy softened his heart. Maybe retirement has afforded a degree of time and freedom for some lighthearted fun. But a look back across those decades of perceptive missives suggests that introspection was there all along, standing backstage in the shadows of the bright lights that often accompany wealth, fame, and success.

How to become a billionaire

Born in Ohio’s poverty-stricken rust belt, Bill describes his hometown of Middletown (memorialized in J.D. Vance’s 2016 Hillbilly Elegy as “Middletucky”) as backwater and hick. “I grew up going to a four-room brick elementary school. By the look of the class pictures, we dressed like Middletucky, not Newport Beach.” He credits his subsequent success to his parents’ decision to move the family to California when he was 10.

The start of that success lies in a most unlikely place. During Bill’s senior year at Duke University, he was involved in a horrific car accident. His Nash Rambler skidded on an icy road and sent the 22-year-old through the windshield. “I was essentially scalped,” Bill says. He spent months in and out of the hospital, enduring multiple skin grafts and recovering from a collapsed lung. But he also discovered Edward O. Thorp’s Beat the Dealer: A Winning Strategy for the Game of Twenty-One. Bill applied his idle hours and mathematical mind to the art of counting cards. “I had all the time in the world, sitting in bed,” Bill says. “I went through thousands of hands of cards and realized, this thing works!”

Once he recovered, Bill had a seamstress sew a surreptitious pocket into his pants. There he hid the entirety of his life savings – $200. “I jumped trains from Durham to Charlotte to Atlanta to Vegas,” he recalls. “A freight train dumped me at the Golden Nugget downtown and I still had my $200. I’d scrounged for food at various stops.” Scrounge, he added, was a nice word for it. Bill checked into the Apache Motel for $6/day and, four months later, had made $10,000 at the blackjack tables. After serving three years in the Navy in Vietnam – a time he describes only as a “disaster” – Bill used his winnings to finance his MBA at UCLA. He also applied Thorp’s gambling principles to the bond market, determining when to spread risk and how to calculate odds in his investment decisions.

It was Bill’s mother, he says, who was responsible for finding him that first job after graduate school. “I was not a gregarious, handshaking person. I didn’t like parties or networking,” he says. More comfortable spending time with numbers than people, Bill began sending resumes. “There were no Xerox machines or computers. I used carbon copies and a typewriter. I sent to everyone. Nothing, nothing, no job.” Bill’s mother came down to visit him in Mission Viejo, when Bill and his first wife welcomed their daughter Jennifer. “The LA Times was sitting there on the coffee table and the Want Ads were laying out.” Bill’s mother noticed a job listing for a security analyst for Pacific Mutual. “Bill, here’s one,” she said. “Don’t you like bonds?” 

It didn’t take long for Bill to rise to Second Vice President of Pacific Mutual. “I was screaming at the top of my lungs in my car, driving home to Mission Viejo. I was making $15,000 a year. I couldn’t believe it.” 

In 1971, Bill became the co-founder of PIMCO (alongside friends Jim Muzzy and Bill Podlich), launching with $12 million in assets. At its peak, PIMCO controlled nearly $2 trillion – more money than Bank of America, JP Morgan, and Goldman Sachs – and remains close to that figure today. He was on a walk one day when that realization struck him. “I just thought, what?!

It was Bill Gross who U.S. Treasury Secretary Tim Geithner called during the 2008 financial crisis. “We were trying to provide solutions to the great recession,” Bill says. “That’s something I’ll always remember – a lot of sleepless nights, but the exhilaration of being at the front of the decision making for the country.” 

The king of charity

Today Bill stays busy managing The William, Jeff, and Jennifer Gross Family Foundation, which holds almost $400 million in assets and makes annual grants totaling $21.5 million. Bill and his two children fund a broad spectrum of causes, but focus their efforts primarily on humanitarian causes, health care, and education. Bill also anonymously donates to others in need.

So deep is his belief in charitable giving that during his time at PIMCO, Bill insisted that every one of his fund managers give back as a condition of their bonus. This practice is now a tradition at PIMCO.

Bill’s daughter, Jennifer, focuses her giving on humanitarian efforts. She funds the Africa Mercy, one of several hospital ships run by Mercy Ships that sails up and down the African coast, delivering medical care to people in need. Jeff has honed in on education, including honoring Teachers of the Year. 

The results are rewarding. “I can’t tell you how many people come up to thank me for their medical care and the treatment they received at Hoag. I remind them I just wrote a check. I didn’t deliver their babies. But it’s nice to get that feedback.”

Celebrate Me Home

Apart from managing his foundation, retirement is offering Bill far more time and space to lead the quiet life he desires. Amy and Bill recently moved into Amy’s dream home at Rockledge by the Sea (a name given to the property by its prior owners), which Bill purchased for her as a surprise. Their home is an architectural reflection of their relationship. And for two people who prefer quiet evenings at home to Orange County’s glitz and glamor, it’s the prefect refuge.

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Photo by Mary Hurlbut

Rockledge by the Sea, appearing behind Villa Rockledge on the right

“We were looking at it for a year, but Bill wanted a place closer to the golf course,” says Amy. “We were on a plane to Europe when he told me he did something. It sounded like he’d done something bad, so I waited. When he said he’d bought Rockledge, I almost jumped out of the plane.” 

For months, Bill snuck around the property before dawn to peer over the fence. “He was caught on camera,” says Amy. “The homeowners finally asked the broker what they should do. He told them, ‘Just leave Bill alone.’” 

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Photo by Mary Hurlbut

Amy commissioned contemporary artists to decorate Rockledge as a love letter to Bill

If Rockledge was Bill’s love letter to Amy, the contemporary art inside is her reply. And there’s no mistaking the message. From the “Love Shack” entry mat to the gleaming golden heart behind the gate, from a Robert Indiana iconic LOVE statue to the many contemporary artistic hearts inside (including the decorative pillows on their bed), the meaning is clear – love wins. 

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Photo by Mary Hurlbut

Bill and Amy with Robert Indiana’s famous “LOVE” sculpture

Amy turned 50 last month, and Bill threw her the party of her life. They invited one of their favorite singers, Kenny Loggins, to perform. With Kenny’s help, Bill took to the stage to serenade his sweetheart. For a soft-spoken man, the song was perfect. “Celebrate Me Home,” he sang to Amy. “Whenever I find myself too all alone, I can sing me home.” 

Indeed he can.

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Photo by Katie Beverley 

Amy and Bill with Kenny Loggins