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The $31 trillion Great Wealth Transfer’s sticking point: art collections that are either ‘connective tissue’ or ‘dinosaur skeletons’ nearly impossible to monetize

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The impending $31 “Great Wealth Transfer” over the coming decade—a once-in-a-generation passing of assets from baby boomers to younger heirs—may turn on a surprising fulcrum: the fate of private art collections. For some families, said Wolfe Tone, vice chair and leader of Deloitte Private in the U.S., art is the “connective tissue,” strengthening intergenerational bonds.

Speaking at the 17th Deloitte Private Art & Finance Conference, held at the Citigroup headquarters in downtown Manhattan on Nov. 4, Tone said the Deloitte Private practice serves nearly 9,000 clients comprising people-owned businesses, family offices and related high-net-worth individuals as well as mid-market private equity and startup technology companies.

Deloitte’s annual Art & Finance report lays out the stakes: nearly $31 trillion will shift from roughly 1.2 million wealthy individuals with net worths above $5 million by 2035, with ultra-high net worth individuals (defined as those with $30 million-plus in assets) accounting for a dominant $19.84 trillion of that sum. Art and collectibles represent 5% of this conservatively. This means that nearly $1 trillion in art could change hands, or about $100 billion annually.​ And if it’s all disorganized, or some of it has been invested in a niche market, this could be a real challenge for wealth managers.

“I know people who collect dinosaur skeletons,” said Hannes Hofmann, Citi’s head of the Family Office Group, during a separate panel at the conference.

He said that being able to monetize an asset is very important and explained that such unusual collections pose a particular challenge to a wealth manager.

From a global bank’s perspective, Hofmann added, it’s harder to value objects in the more niche art collectibles market for credit or insurance purposes, because there isn’t much or any transactional history that can help produce a valuation. In a credit event, he added, it’s harder to monetize collateral when only a small group of collectors are providing liquidity.

This fits into a wider picture, Hofmann explained. Citi has seen collectors’ interests diversify from the core art forms of paintings, paper and sculpture, he said, especially when it comes to the next generation, with interests as diverse as NFTs or prehistoric fossils, and the bank is constantly evolving with clients’ needs. Still, Hofmann said about niche investments, “there’s no question that it’s an area that will continue to grow.”

Wedge or glue?

In addition to difficulties in assigning value to certain assets, issues around ownership and provenance complicate the picture too.

As Adriano Picinati di Torcello, a 30-year veteran of the industry and the coordinator of Deloitte’s Global Art & Finance efforts since 2008, explained in an interview with Fortune: “Collections can bring families closer together, but also drive them apart.” This is especially the case when key questions—like which works should be kept, sold, or donated—go unresolved.​

“It’s a critical issue,” di Torcello continued, “and if you are not well prepared, you will end up into a disaster.” Speaking generally about his dealing with clients, he said it’s not uncommon at all to find clients have missing documentation, even missing artworks.

“They don’t know even maybe where the works maybe are, or maybe if they’ve been loaned or whatever,” he added. Art collections among the wealthy aren’t just valuable assets, they’re emotional anchors, cultural signifiers, and increasingly, flashpoints of family discord.

Both Citi and Deloitte’s findings in this area resonate with each other. For its part, Citi’s Global Family Office Report 2025 reveals that art represents 1% of the average family office’s assets. But there is more to art than its portfolio allocation implies: “Creating a shared vision and values for their future together” is among the top three concerns of the families in the survey.

Deloitte’s Art & Finance report, commissioned by di Torcello’s team and now in its ninth edition, states bluntly that the “next generation of art heirs is largely uninformed and unprepared.” The report, which draws on insights from 57 experts and nearly 500 survey responses, finds that roughly six in 10 collectors (61%) haven’t discussed their art collection with their heirs at all, while another 21% had only mentioned it without any in-depth discussion about what inheriting entails.

As di Torcello explained to Fortune, this can backfire if the generations aren’t in sync with each other. It puts a lot of pressure on wealth managers like himself, who “need to be there to help to create this dialogue between the different generations.”

For example, they often need to prepare the older generation to accept that “maybe your kids, they don’t like whatever you have collected because they prefer more the, I don’t know, urban art or digital art or whatsoever.”

He also described scenes that would come straight out of the TV series Succession. “Of course, if it’s not well organized, you can create also conflict between the kids, because they would say, ‘Why do you get this one instead of this one?’” You can end up with one heir getting a collection with a higher value than other assets and that “can be a source of tensions,” he said.

As for what millennials actually like, di Torcello said he has observed a generational shift in priorities. He told Fortune that his practice is seeing “a kind of a return to emotion” in younger heirs. The older generation discusses financial attributes, whereas the younger heirs are “kind of going back to emotion, culture, purpose.” He said the financial dimension remains, but is losing its importance somewhat.

Art is still resisting the tech age in the era of AI

Di Torcello explained that over several decades in the industry, he has witnessed waves of digital transformation ripple through other industries, but art has remained stubbornly resistant to modern tools and efficiencies. He referenced a keynote from the Nov. 4 conference from Carina Popovici, co-founder and CEO of a tech company called Art Recognition that does exactly what its name implies: uses artificial intelligence to deduce whether a painting is a secret Raphael or a knock-off. A member of the crowd raised their hand to strenuously disagree with the notion of such technology entering the art world.

“I think we have to be open,” di Torcello said, arguing, “it’s not that technology is replacing the human being, it’s just an additional tool to support.” He told Fortune that he thinks the biggest challenge for his sector is efficiency, a theme in the Art & Finance report for eight years running. In his opinion, the sector simply needs modernization. “This is affecting all stakeholders in this art and finance ecosystem,” di Torcello said, “from the artist, from the galleries, the dealers, the auction houses, to the museums, to the collector.” He added that this is something “very precious, it’s something very, very important for our society, for our humanity in general. And I don’t understand why we don’t try to make things more efficient in that sector.”

Citi’s Hofmann argued that art can become a vital bridge across generations. “Art is more than an investment,” he said in a statement to Fortune—although it is hopefully also that. It’s about passion, supporting artists, and it’s about “beautiful things that hopefully enhance the quality of life of the family in the future. Art can be something that keeps the family together and shapes the family, especially if the next generation grows up with it.”



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The ‘Mister Rogers’ of Corporate America shows Gen Z how to handle toxic bosses

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After two decades of climbing the corporate ladder at companies ranging from ABC, ESPN, and Charter Communications (commonly known as Spectrum), Timm Chiusano quit it all to become a content creator. 

He wasn’t just walking away from high titles, but a high salary, too. In his peak years, Chiusano made $600,000 to $800,000 annually. But in June of 2024, after giving a 12-week notice, he “responsibility fired himself” from his corporate job as VP of production and creative services at Charter.

He did it all to help others navigate the challenges of a workplace, and appreciate the most mundane parts of life on TikTok.

@timmchiusano

most people are posting their 2024 recaps; these are a few of my favorite moments from the year that was, but i need to start reintroducing myself too i dont have a college degree, no one in my life knew that until i was 35 when i eventually got my foot in the door in my early 20’s after a few years of substitute teaching and part time jobs, i thought for sure i had found the career path of my dreams in live sports production i didn’t think i had a chance of surviving that first college football season but i busted my ass, stuck around and got promoted 5 times in 5 years then i met a girl in Las Vegas, got married in 7 months, and freaked out about my career that had me travelling 36 weeks a year i had to find a more stable “desk job”, i was scared shitless that i was pigeonholed and the travel would eventually destroy my marriage i crafted a narative for espn arguing they needed me on their marketing team because of my unique perspective coming from the production side i got rejected, but kept trying and a year i got that job the 7 years with espn were incredible, but also exhausting and raised all kinds of questions about corporate america, toxic situations, and capitalism in general why was i borderline heart attack stressed so often when i could see that my ideas were literally generating 2,000 times the money that i was getting paid? in 2012 i had a kid and in 2013 i got the biggest job of my career to reinvent how to produce 20,000 commercials a year for small business it took 12 rounds of interviews, a drug test i somehow passed, and a background check that finally made me tell my wife of 8 years that i didnt have a college degree they brought me in the thursday before my first day and told me what i told grace in that clip the next decade was an insane blur; i saw everything one would ever see in their career from the perspective of an executive at a fortune 100 i started making tiktoks, kinda blacked out at some point in 2019 and responsibly fired myself in 2024 to see what i might be capable of on my own with all the skills i picked up along my career journey now the mission is pay what i know forward, and see if i can become the mr rogers of corporate america cc: @grace beverley @Ryan Holiday @Subway Oracle

♬ original sound – timm chiusano

What started as short-video vlogs on just about anything in 2020 (reviews on protein bars, sushi, and sneakers) later transitioned to videos on growing up, and dealing with life’s challenges, like coming to terms when you have a toxic boss. Today, his platform on TikTok has over 1 million followers

With the help of going viral from his “loop” format where videos end and seamlessly circle back to the beginning, he began making more videos as a side-hustle on top of his day-to-day tasks in the office.

“How can I get people to be smarter and more comfortable about their careers in ways that are gonna help on a day-to-day basis?” Chiusano told Fortune.

Today, he could go by many titles: former vice president at a Fortune 100 company, motivational speaker, dad, content creator, or as he labels himself, the Mister Rogers of Corporate America. 

Just as the late public television icon helped kids navigate the complexities of childhood, Chiusano wants to help young adults think about how to approach their careers and their potential to make an impact. 

“Mister Rogers is the greatest of all time in his space. I will never get to that level of impact. But it’s an easy way to describe what I’m trying to do, and it consistently gives me a goal to strive for,” he said. “There are some parallels here with the quirkiness.”

Firing himself after 25 years in the corporate world

Even with years in corporate, Chiusano doesn’t resemble the look of a typical buttoned-up executive. Today, he has more of a relaxed Brooklyn dad attire, with a sleeve of tattoos and a confidence to blend in with any trendy middle aged man in Soho. During our interview, he showed off one of the first tattoos he got: two businessmen shaking hands, a reference to Radiohead’s OK Computer album.

“This is a dope ass Monday in your 40s,” began one of his videos.

It consisted of Chiusano doing everyday things such as eating leftovers, going to the gym, training for the NYC marathon, taking out the trash, dropping his daughter off at school, a rehearsal for a Ted Talk, eating lunch with his wife, and brand deal meetings. Though the content sounds pretty normal, that’s the point. 

“The reason why I fired myself in the first place was to be here,” he says in the video while picking his daughter up from school.

Today, Chiusano spends his days making content on navigating workplace culture, public speaking, brand deals, brand partnerships, executive coaching, writing a book, and the most important job: being a dad to his 13-year-old daughter Evelyn.

“I’m basically flat [in salary] to where I was, and this is everything I could ever want in the world,” he said. “The ability to send my kid to the school she’s been going to, eat sushi takeout almost as much as I’d like, and do nice things for my wife.”

In fact, when sitting inside one of his favorite New York City spots, Lure Fishbar, he keeps getting stopped by regulars who know him by name. He points out that one of his favorite interviews he filmed here was with legendary filmmaker Ken Burns.

Advice to Gen Z

In a time where Gen Z has been steering to more unconventional paths, like content creation or skill trades rather than just a 9-to-5 office job, Chiusano opens up a lens to what life looks like when deciding to be present rather than always looking for what’s next—a mistake he said he made in his 20s. 

Instead, he wants to teach the younger generation to build skills for as long as you can, but “if you are unhappy, that’s a very different conversation.”

“I think some people will make themselves more unhappy because they feel like that’s what’s expected of a situation,” he said.

“I would love to be able to empower your generation more, to be like somebody’s gonna have to be the head of HR at that super random company to put cool standards and practices in place for better work-life balance for the employees.” 





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Mark Zuckerberg says the ‘most important thing’ he built at Harvard was a prank website

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For Mark Zuckerberg, the most significant creation from his two years at Harvard University wasn’t the precursor to a global social network, but a prank website that nearly got him expelled.

The Meta CEO said in a 2017 commencement address at his alma mater that the controversial site, Facemash, was “the most important thing I built in my time here” for one simple reason: it led him to his wife, Priscilla Chan.

“Without Facemash I wouldn’t have met Priscilla, and she’s the most important person in my life,” Zuckerberg said during the speech.

In 2003, Zuckerberg, then a sophomore, created Facemash by hacking into Harvard’s online student directories and using the photos to create a site where users could rank students’ attractiveness. The site went viral, but it was quickly shut down by the university. Zuckerberg was called before Harvard’s Administrative Board, facing accusations of breaching security, violating copyrights, and infringing on individual privacy.

“Everyone thought I was going to get kicked out,” Zuckerberg recalled in his speech. “My parents came to help me pack. My friends threw me a going-away party.”

It was at this party, thrown by friends who believed his expulsion was imminent, where he met Chan, another Harvard undergraduate. “We met in line for the bathroom in the Pfoho Belltower, and in what must be one of the all time romantic lines, I said: ‘I’m going to get kicked out in three days, so we need to go on a date quickly,’” Zuckerberg said.

Chan, who described her now-husband to The New Yorker as “this nerdy guy who was just a little bit out there,” went on the date with him. Zuckerberg did not get expelled from Harvard after all, but he did famously drop out the following year to focus on building Facebook.

While the 2010 film The Social Network portrayed Facemash as a critical stepping stone to the creation of Facebook, Zuckerberg himself has downplayed its technical or conceptual importance.

“And, you know, that movie made it seem like Facemash was so important to creating Facebook. It wasn’t,” he said during his commencement speech. But he did confirm that the series of events it set in motion—the administrative hearing, the “going-away” party, the line for the bathroom—ultimately connected him with the mother of his three children.

Chan, for her part, went on to graduate from Harvard in 2007, taught science, and then attended medical school at the University of California, San Francisco, becoming a pediatrician.

She and Zuckerberg got married in 2012, and in 2015, they co-founded the Chan Zuckerberg Initiative, a philanthropic organization focused on leveraging technology to address major world challenges in health, education, and science. Chan serves as co-CEO of the initiative, which has pledged to give away 99% of the couple’s shares in Meta Platforms to fund its work.

You can watch the entirety of Zuckerberg’s Harvard commencement speech below:

For this story, Fortune journalists used generative AI as a research tool. An editor verified the accuracy of the information before publishing. 



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Senate Dems’ plan to fix Obamacare premiums adds nearly $300 billion to deficit, CRFB says

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The Committee for a Responsible Federal Budget (CRFB) is a nonpartisan watchdog that regularly estimates how much the U.S. Congress is adding to the $38 trillion national debt.

With enhanced Affordable Care Act (ACA) subsidies due to expire within days, some Senate Democrats are scrambling to protect millions of Americans from getting the unpleasant holiday gift of spiking health insurance premiums. The CRFB says there’s just one problem with the plan: It’s not funded.

“With the national debt as large as the economy and interest payments costing $1 trillion annually, it is absurd to suggest adding hundreds of billions more to the debt,” CRFB President Maya MacGuineas wrote in a statement on Friday afternoon.

The proposal, backed by members of the Senate Democratic caucus, would fully extend the enhanced ACA subsidies for three years, from 2026 through 2028, with no additional income limits on who can qualify. Those subsidies, originally boosted during the pandemic and later renewed, were designed to lower premiums and prevent coverage losses for middle‑ and lower‑income households purchasing insurance on the ACA exchanges.

CRFB estimated that even this three‑year extension alone would add roughly $300 billion to federal deficits over the next decade, largely because the federal government would continue to shoulder a larger share of premium costs while enrollment and subsidy amounts remain elevated. If Congress ultimately moves to make the enhanced subsidies permanent—as many advocates have urged—the total cost could swell to nearly $550 billion in additional borrowing over the next decade.

Reversing recent guardrails

MacGuineas called the Senate bill “far worse than even a debt-financed extension” as it would roll back several “program integrity” measures that were enacted as part of a 2025 reconciliation law and were intended to tighten oversight of ACA subsidies. On top of that, it would be funded by borrowing even more. “This is a bad idea made worse,” MacGuineas added.

The watchdog group’s central critique is that the new Senate plan does not attempt to offset its costs through spending cuts or new revenue and, in their view, goes beyond a simple extension by expanding the underlying subsidy structure.

The legislation would permanently repeal restrictions that eliminated subsidies for certain groups enrolling during special enrollment periods and would scrap rules requiring full repayment of excess advance subsidies and stricter verification of eligibility and tax reconciliation. The bill would also nullify portions of a 2025 federal regulation that loosened limits on the actuarial value of exchange plans and altered how subsidies are calculated, effectively reshaping how generous plans can be and how federal support is determined. CRFB warned these reversals would increase costs further while weakening safeguards designed to reduce misuse and error in the subsidy system.

MacGuineas said that any subsidy extension should be paired with broader reforms to curb health spending and reduce overall borrowing. In her view, lawmakers are missing a chance to redesign ACA support in a way that lowers premiums while also improving the long‑term budget outlook.

The debate over ACA subsidies recently contributed to a government funding standoff, and CRFB argued that the new Senate bill reflects a political compromise that prioritizes short‑term relief over long‑term fiscal responsibility.

“After a pointless government shutdown over this issue, it is beyond disappointing that this is the preferred solution to such an important issue,” MacGuineas wrote.

The off-year elections cast the government shutdown and cost-of-living arguments in a different light. Democrats made stunning gains and almost flipped a deep-red district in Tennessee as politicians from the far left and center coalesced around “affordability.”

Senate Minority Leader Chuck Schumer is reportedly smelling blood in the water and doubling down on the theme heading into the pivotal midterm elections of 2026. President Donald Trump is scheduled to visit Pennsylvania soon to discuss pocketbook anxieties. But he is repeating predecessor Joe Biden’s habit of dismissing inflation, despite widespread evidence to the contrary.

“We fixed inflation, and we fixed almost everything,” Trump said in a Tuesday cabinet meeting, in which he also dismissed affordability as a “hoax” pushed by Democrats.​

Lawmakers on both sides of the aisle now face a politically fraught choice: allow premiums to jump sharply—including in swing states like Pennsylvania where ACA enrollees face double‑digit increases—or pass an expensive subsidy extension that would, as CRFB calculates, explode the deficit without addressing underlying health care costs.



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