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Reinsurance Group of America’s Tony Cheng on staying humble in leadership

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It’s rare to be offered a big promotion and turn it down, but it’s even rarer to warn superiors you don’t feel prepared for the role and be appointed anyway.

Yet that’s precisely what happened to Reinsurance Group of America boss, Tony Cheng, in his early years with the business. Cheng has worked his way up the ranks of RGA over the past three decades, helping grow the company to its current position of $3.9 trillion of reinsurance covering active policyholders.

In 2025, RGA announced a landmark $1.5 billion deal with Equitable to reinsure $32 billion worth of life insurance policies, securing its place as an industry leader and expected to boost earnings for quarters come.

Sitting down for an exclusive interview with Fortune this summer, Cheng reflected on that all-important promotion to CEO, and the value of staying humble even in the C-suite.

The following has been condensed and edited for clarity.

Tony, in an era where job-hopping is often seen as the fast track to career growth, you’ve chosen a different tactic—working up through RGA since 1997. Where did your work ethic come from, and what’s inspired your long-standing commitment to the company?

I was born in Hong Kong, and my parents—both teachers—felt for the future of their four kids (of which I was the youngest) Australia would provide the Western education they wanted. So I grew up in Australia from nine months to the age of 20 and didn’t travel overseas much.

My parents worked incredibly hard. Mom looked after the four kids and Dad unfortunately had to give up his love for teaching because it just wouldn’t pay the bills. Eventually they opened up small businesses and then we, the four kids, on the weekend would go work there—12 hour days—and didn’t think otherwise. That really bred in the sacrifice of the parents, the hard work, all things I’d wish to pass onto my kids.

Growing up as many of us in a Western country but very Asian family do, I think I went to Asia once in my life, so [I took] an opportunity to join RGA in 1997 in Malaysia. 

Between 1999 and 2002 you returned to the States to earn an MBA while working for RGA, before leaving to head up the Hong Kong office. When you arrived, you had a team of 10. The Asia Pacific region now has more than 1,000 employees and revenues of $4 billion. Are there untapped career opportunities in emerging markets as opposed to progressing in established regions?

We had a very small operation, but we were actually covering about 500 million people. It was Hong Kong and Southeast Asia so Malaysia, Thailand, all those countries. I went there as the actuary, and a year and a half later they promoted me to be the CEO of that business. It was daunting, right? 

The first time I was asked to take it by my boss, I sort of said, ‘No, I’m too young.’ At the time I was 29. He ignored that. 

The equation in my mind was I’ve probably got a 10% chance of success—and that would be great—or a 90% chance of failure, but hey, I’m gonna learn a hell of a lot. I had no mortgage, no kids, so just wanted to learn. Maybe that instinct, that desire and drive to keep learning was from my parents being teachers.

In its latest financial results RGA reported revenues of $22.1 billion. How has the start-up mentality you learned in Asia helped grow the business globally?

We built that business up with incredible hard work. I’d joke internally that once every month or so pest control would come in, and that meant we could go home at 5 o’clock because what else were we going to do with ourselves? That was the spirit. In the early days, you solve problems. I’d say to the team: ‘Let’s just try. We know it’s really hard, but let’s just try.’

In the U.S., people usually don’t create new products or create new things because the market’s so big, a lot of it’s already played out and it’s been created. Any good idea has been thought of, and that’s truly okay.

It’s actually more connecting the dots in the U.S., but with a drive to not just settle on: ‘Hey, here’s the market, we want a share of it’ it’s a drive to create new things or a new combination of things so that we [can] increase the pie and share in that greater value creation. That’s always been in the company spirit, it was just really about bringing that out again to the forefront.

Like a lot of other Fortune 500 CEOs we speak to, you clearly have a love for learning. In a world where AI is expected to disrupt the labor market, what are the skills you’re looking for in new talent?

I can only think of what I advise my son, who’s in his second year of college. As the younger generation already knows, AI is gonna accelerate, and therefore number one they’ve absolutely got to be able to use it and partner with it.

Ultimately AI, one would think, is gonna replace whatever is mathematically easier to replace. Had a conversation at one of the town halls with some risk professionals in the U.S. last week and I said all those soft skills really matter, you’ve still got to learn the hard skills, you’ve got to understand your subject matter expertise regardless of technology, but increasingly all those abilities to interact, to communicate, to join the dots, to be able to understand information, communicate it, and just put those dots together is the stuff that’s gonna be obviously harder for AI to replicate. 

Maybe it will one day, but then you’ve just got to keep elevating yourself. So, what is that a lesson of? It is a lesson of continually adapting, continually learning, a bit like a sports person. When they’ve lost their passion to play and fight, it’s time to retire. 

For me, when I’ve lost that passion to learn and grow, you’re probably not gonna give it your full go, hence maybe the learning really just keeps me going. It’s not like I ever said, ‘Hey, I want to be the CEO of the company.’ I was so far away, I just wanted to be treated right and enjoy the journey and the growth,

So the lesson to individuals is you’ve just got to keep learning, you’ve got to be humble. If you’re not humble, you’re not gonna listen to yourself or your failings, you’re gonna blame them on something else as opposed to, ‘Well, what was my role in that?’ so I can learn. 



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Congressman leading GOP’s mid-term House campaign says Trump is intimately involved in recruitment

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Even though Republican Brian Jack is only a first-term congressman, he has become a regular in the Oval Office these days. As the top recruiter for his party’s House campaign team, the Georgia native is often reviewing polling and biographies of potential candidates with President Donald Trump.

Lauren Underwood, an Illinois congresswoman who does similar work for Democrats, has no such West Wing invitation. She is at the other end of Pennsylvania Avenue working the phones to identify and counsel candidates she hopes can erase Republicans’ slim House majority in November’s midterm elections.

Although they have little in common, both lawmakers were forged by the lessons of 2018, when Democrats flipped dozens of Republican-held seats to turn the rest of Trump’s first term into a political crucible. Underwood won her race that year, and Jack became responsible for dealing with the fallout when he became White House political director a few months later.

Underwood wants a repeat in 2026, and Jack is trying to stand in her way.

For Republicans, that means going all-in on Trump and his “Make American Great Again” agenda, gambling that durable enthusiasm from his base will overcome broader dissatisfaction with his leadership.

“You’re seeing a lot of people very inspired by President Trump,” Jack said about his party’s House candidates. “They’re excited to serve in this body alongside him and the White House. That’s been a tool and a motivating factor for so many people who want to run.”

Underwood said she is looking for candidates with community involvement and public service beyond Washington politics. A registered nurse, she was a health care advocate before she ran in 2018, joining a cadre of Democratic newcomers that included military veterans, educators, activists and business owners.

“It’s about having ordinary Americans step up” in a way that “draws a sharp contrast with the actions of these MAGA extremists,” she said.

Trump’s involvement is more direct than in 2018

It’s routine for a president’s party to lose ground in Congress during the first midterms after winning the White House. Trump, however, is in the rare position to test that historical trend with a second, nonconsecutive presidency.

Neither party has released its list of favored candidates in targeted seats. But Jack said Oval Office discussions with Trump focus on who can align with the White House in a way that can win.

Jack highlighted former Maine Gov. Paul LePage as an example. LePage is running in a GOP-leaning district where Democrats face the challenge of replacing Rep. Jared Golden, another member of the party’s 2018 class who recently announced he would not seek reelection.

Trump’s involvement contrasts with 2017, when he was not as tied to House leadership, including then-Speaker Paul Ryan, R-Wis., on details of the midterm campaign as he is now. Jack, who got his start with Trump by managing delegate outreach before the 2016 convention, was White House deputy political director during that span. He was promoted to political director after the 2018 losses.

Jack continued advising the president, especially on his endorsements, between Trump’s 2021 departure for the White House and Jack’s own congressional campaign in 2024. He described Trump as intimately involved in recruitment decisions and open to advice on his endorsements since those 2018 defeats.

Trump loyalty will not always be easy to measure, especially in first-time candidates.

But Jack said Republicans have quality options. He pointed to Albuquerque, New Mexico, where Republicans could have a competitive primary that includes Jose Orozco, a former Drug Enforcement Administration contractor, and Greg Cunningham, a former Marine and police officer.

“They both have very inspirational stories,” Jack said.

Orozco has asked voters to “give President Trump an ally in Congress.” Cunningham did not focus on Trump in his campaign launch.

Democrats describe a district-by-district approach

Underwood said Democrats are replicating a district-by-district approach of 2018. Recruiting in the Trump era, she said, is more often about talking with prospective candidates who raised their hands to run than about coaxing them into politics.

The notable numbers of women and combat veterans in her first-term class, Underwood said, was not a top-down strategy but the result of candidates who saw Trump and Republicans as threats to functional government and democracy.

Underwood, who at age 32 became the youngest Black woman ever to serve in Congress after her 2018 election, recalled that Republicans’ efforts to repeal the Affordable Care Act spurred her to run because of her training as a nurse. She shares those experiences with recruits, sharpening how they can connect their ideas and background to the job of a congressperson.

Underwood said she also regularly fields questions about serving in an era of political violence and about the day-to-day balance of being a candidate or congressperson, especially from recruits who have children.

National security is again a draw for Democrat. Former Marine JoAnna Mendoza is running in a largely rural southern Arizona seat and former Rep. Elaine Luria, another Underwood classmate and former naval officer, is running again in Virginia after losing her seat in 2022. Luria was among the lead House investigators of the Jan. 6, 2021, Capitol riot.

Underwood said there are clear parallels to 2018, when successful congressional candidates included Mikie Sherrill, a former Navy helicopter pilot who is now New Jersey governor-elect; Jason Crow, a former Army Ranger who is one of her recruiting co-chairs; and Virginia Gov.-elect Abigail Spanberger, a former CIA case officer.

Democrats also noted the need to find candidates who reflect a district’s cultural sensibilities, meaning a candidate who can withstand Republican accusations that national Democrats are out of touch with many voters.

For instance, in a South Texas district, the top potential Democratic challenger is Tejano music star Bobby Pulido. The five-time Latin Grammy nominee has criticized progressive Rep. Alexandria Ocasio-Cortez of New York for using the term “Latinx” rather than “Latino” or “Latina.”

Trump’s gerrymandering fight causes uncertainty

Mid-decade gerrymandering, mostly in Republican-led states at Trump’s behest, leaves the state of the 435 House districts in flux. Even with the changes, Democrats identify more than three dozen Republican-held seats they believe will be competitive. Republicans counter with about two dozen Democratic-held seats they think can flip.

In the Southwest, Democrats are targeting all three Republican seats in Arizona. The GOP is aiming at three Democratic seats in Nevada. From the Midwest across to the Philadelphia suburbs, Democrats want to flip two Iowa seats, two in Wisconsin three in Michigan, three in Ohio and four in Pennsylvania. Republicans are targeting four Democratic seats in New York.

Nearly all Democratic targets were within a 15-percentage point margin in 2024, many of them much closer than that. Democratic candidates in 2025 special elections typically managed double-digit gains compared with Trump’s margins in 2024, including a recent special House election in Tennessee, when Democrats came within 9 points in a district Trump won by 22 points.

“It’s the same kind of shifts that we saw in 2017 before the 2018 wins,” said Meredith Kelly, a top official at the Democratic Congressional Campaign Committee during Trump’s first presidency. “So, it becomes a mix of that national environment and finding the right candidates who fit a district and can take advantage.”



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Connecticut cashes in on Hallmark Movie status to drive kitschy Christmas tourism boom

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“Christmas at Pemberly Manor” and “Romance at Reindeer Lodge” may never make it to Oscar night, but legions of fans still love these sweet-yet-predictable holiday movies — and this season, many are making pilgrimages to where their favorite scenes were filmed.

That’s because Connecticut — the location for at least 22 holiday films by Hallmark, Lifetime and others — is promoting tours of the quaint Christmas-card cities and towns featured in this booming movie market; places where a busy corporate lawyer can return home for the holidays and cross paths with a plaid shirt-clad former high school flame who now runs a Christmas tree farm. (Spoiler alert: they live happily ever after.)

“It’s exciting — just to know that something was in a movie and we actually get to see it visually,” said Abby Rumfelt of Morganton, North Carolina, after stepping off a coach bus in Wethersfield, Connecticut, at one of the stops on the holiday movie tour.

Rumfelt was among 53 people, mostly women, on a recent weeklong “Hallmark Movie Christmas Tour,” organized by Mayfield Tours from Spartanburg, South Carolina. On the bus, fans watched the matching movies as they rode from stop to stop.

To plan the tour, co-owner Debbie Mayfield used the “ Connecticut Christmas Movie Trail ” map, which was launched by the wintry New England state last year to cash in on the growing Christmas-movie craze.

Mayfield, who co-owns the company with her husband, Ken, said this was their first Christmas tour to holiday movie locations in Connecticut and other Northeastern states. It included hotel accommodations, some meals, tickets and even a stop to see the Rockettes in New York City. It sold out in two weeks.

With snow flurries in the air and Christmas songs piped from a speaker, the group stopped for lunch at Heirloom Market at Comstock Ferre, where parts of the Hallmark films “Christmas on Honeysuckle Lane” and “Rediscovering Christmas” were filmed.

Once home to America’s oldest seed company, the store is located in a historic district known for its stately 1700s and 1800s buildings. It’s an ideal setting for a holiday movie. Even the local country store has sold T-shirts featuring Hallmark’s crown logo and the phrase “I Live in a Christmas Movie. Wethersfield, CT 06109.”

“People just know about us now,” said Julia Koulouris, who co-owns the market with her husband, Spiros, crediting the movie trail in part. “And you see these things on Instagram and stuff where people are tagging it and posting it.”

Christmas movies are big business — and a big deal to fans

The concept of holiday movies dates back to 1940s, when Hollywood produced classics like “It’s A Wonderful Life,” “Miracle on 34th Street” and “Christmas in Connecticut,” which was actually shot at the Warner Bros. studios in Burbank, California.

In 2006, five years after the launch of the Hallmark Channel on TV, Hallmark “struck gold” with the romance movie “The Christmas card,” said Joanna Wilson, author of the book “Tis the Season TV: The Encyclopedia of Christmas-Themed Episodes, Specials and Made-for-TV Movies.”

“Hallmark saw those high ratings and then started creating that format and that formula with the tropes and it now has become their dominant formula that they create for their Christmas TV romances,” she said.

The holiday movie industry, estimated to generate hundreds of millions of dollars a year, has expanded beyond Hallmark and Lifetime. Today, a mix of cable and broadcast networks, streaming platforms, and direct-to-video producers release roughly 100 new films annually, Wilson said. The genre has also diversified, with characters from a wider range of racial and ethnic backgrounds as well as LGBTQ+ storylines.

The formula, however, remains the same. And fans still have an appetite for a G-rated love story.

“They want to see people coming together. They want to see these romances. It’s a part of the hope of the season,” she said. “Who doesn’t love love? And it always has a predictable, happy ending.”

Hazel Duncan, 83, of Forest City, North Carolina, said she and her husband of 65 years, Owen, like to watch the movies together year-round because they’re sweet and family-friendly. They also take her back to their early years as a young couple, when life felt simpler.

“We hold hands sometimes,” she said. “It’s kind of sweet. We’ve got two recliners back in a bedroom that’s real small and we’ve got the TV there. And we close the doors off and it’s just our time together in the evening.”

Falling in love again… with a state

Connecticut’s chief marketing officer, Anthony M. Anthony, said the Christmas Movie Trail is part of a multipronged rebranding effort launched in 2023 that promotes the state not just as a tourist destination, but also as a place to work and live.

“So what better way to highlight our communities as a place to call home than them being sets of movies?” he said.

However, there continues to be debate at the state Capitol over whether to eliminate or cap film industry tax credits — which could threaten how many more of these movies will be made locally.

Christina Nieves and her husband of 30 years, Raul, already live in Connecticut and have been tackling the trail “little by little.”

It’s been a chance, she said, to explore new places in the state, like the Bushnell Park Carousel in Hartford, where a scene from “Ghost of Christmas Always” was filmed.

It also inspired Nieves to convince her husband — not quite the movie fan she is — to join her at a tree-lighting and Christmas parade in their hometown of Windsor Locks.

“I said, listen, let me just milk this Hallmark thing as long as I can, OK?” she said.



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Alphabet poised for another paper gain as SpaceX valuation jumps

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Alphabet Inc. is set to book another sizable paper gain after SpaceX completes a tender offer that effectively values the closely held company at about $800 billion.

SpaceX’s insider share sale was priced at $421 a share, Bloomberg reported Friday, which would mark a sharp jump in valuation from earlier secondary transactions. That is likely to lift the carrying value of Google’s long-standing investment in Elon Musk’s rocket and satellite company. 

Alphabet, Google’s parent, has been an investor in SpaceX since at least 2015, when it joined Fidelity Investments in a $1 billion funding round for a combined stake of about 10% at the time, Bloomberg has reported.

A representative for Google declined to comment, citing their policy of not disclosing or commenting on individual private holdings. 

A similar revaluation boosted Alphabet’s earnings earlier this year. In April, the company disclosed an $8 billion unrealized gain tied to its investment in a private company — widely understood to be SpaceX — after a tender offer late last year valued the company at about $350 billion. That gain helped lift Alphabet’s net income for the March quarter above Wall Street expectations.

While Alphabet does not name individual private holdings in its financial filings, changes in SpaceX’s valuation have previously flowed through earnings as “unrealized gains on non-marketable equity securities.” 

With SpaceX’s latest tender implying a much higher valuation, investors will be watching Alphabet’s next earnings report for signs of another accounting boost.

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