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Bill Ackman has grown Pershing Square Capital Management to more than $16 billion from $54 million since he founded the fund nearly two decades ago. The 57-year-old activist investor speaks with On The Money about his return to office policy, his possible presidential picks and why hes still bullish on New York City.

Lydia: You are among the big names on Wall Street who didn’t move to Florida. Why?

Bill: The short answer is that I love New York City. My desire to be successful is founded on a desire to be independent. It always seemed crazy to me to sacrifice that independence to save money on taxes. If you make $100 million some people in finance make even more than that you can save $25 million of that by living somewhere cheaper.

Some people choose to manage their lives that way. I do think it’s incumbent upon New York City to make this a desirable place to live and we have to make it an attractive place to do business. If one super wealthy person leaves the city thats really bad for the revenue. I dont think it’s smart to push taxes higher I think that would actually generate less revenue.

Lydia: There have been some top players in finance like Ken Griffin who have made a show of moving to Miami and talking about how smart it is for their business. But do you think that trend will be reversed? Will we see a lot of headlines in the next year about people moving back?

Bill: I think it’s a great thing that [Citadel founder] Ken Griffin is building a major campus, if you will, in New York City on Park Avenue. I think thats an amazing thing for NYC whether it’s his primary office or not, and it speaks to the fact that a lot of the youngest, most talented people want to be here. My nephew graduated from Harvard and many of his classmates moved here even before they had a job. The city is still a big draw for young people and if this is where the talented, young people want to be, then the companies will have to have a major presence here.

Lydia: Given the younger generation wants flexibility, is it realistic to expect people to return to the office five days a week? On the flip side, can New York City flourish if you dont have people back in Midtown and back in office buildings?

Bill: Everyone wants more flexible work whether its a school play, a sports game you dont want to miss and we have technology that lets you do that. What weve done at Pershing Square is bring people back five days a week 10 months a year. Of course if theres something you need to do like a doctors appointment or working from home one day, use your best judgment. And then we give people July and August to work from anywhere with the caveat that if there’s something where we need to bring everyone together, you show up. Weve experimented with that for two years and thats worked well, people like the balance, and it works for our business.

Lydia: And you believe New York will still be a place where businesses want to operate? 

Bill: I think if NYC became an unsafe place the images you see of San Francisco where you have open air drug users lying on the street that would be very damaging and could be a tipping point for people leaving the city.

You have to manage the city and its population effectively. In San Francisco you have homeless people acting in a threatening and hostile way thats led to the emptying out and death spiral of San Francisco. Again you want to manage a city so that it is pro-business and pro-resident and you want to show care for people who are less fortunate, but that doesnt mean they can defecate on the street and threaten parents or kids.

Lydia: Is NYC poised to go into that kind of death spiral?

Bill: No, I dont think so. We have a mayor who has for obvious reasons respect for the police force and I think they respect him. I think thats really important. The whole defunding the police movement was not a good one. Bail reform went too far. If you believe the statistic, it’s several hundred people committing the vast majority of street crime and those people should be locked up.

Lydia: The new movie Dumb Money and the meme stock craze clearly a cautionary tale of a short bet gone wrong. What do you make of that film?

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Bill: We are among the most famous short sellers but thats because we shorted two stocks in the last twenty years. One short theres a movie about Herbalife [Betting on Zero] and the other short theres a book about MBIA [Confidence Game]. But we dont short stocks for precisely the reason you say. We gave up that business a long time ago because its too risky. Even when youre right you can lose a lot of money. Of course, short sellers can do amazing research.

Lydia: Youve publicly applauded the work Hindenburg has done on Carl Icahns firm. How are you thinking about Icahn now? Do you think the report captured whats going on at his firm?

Bill: What Hindenburg said has been proven out.

Lydia: Youve expressed support for a lot of different 2024 presidential candidates. Anyone else you plan to support? 

Bill: Id love Jamie Dimon to be president but hes made it clear hes not going to run. Id love for a candidate of his quality to run. I think Biden-Trump part II is not the best option for America. It would be great for us to be brought together by a more centrist candidate that members of both parties can vote for. 

Lydia: What about Vivek or RFK Jr. youve tweeted support for?

Bill: Id like to see multiple alternatives. Ive been supportive of Vivek because I know him and hes super smart and capable. I wish he was a more centrist candidate. Ive not yet met RFK but hopefully will have an opportunity to do so. But I still havent found my ideal candidate. Biden should step aside and that would create a flurry of alternative candidates. People are afraid to run against the president and I think theres some possibility of that happening.

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Trump’s pride vs Putin’s legacy: What to expect from pivotal Ukraine summit

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Trump's pride vs Putin's legacy: What to expect from pivotal Ukraine summit

Donald Trump and Vladimir Putin will meet for the first time in six years on Friday, with a possible deal to end the Ukraine war on the agenda.

Mr Trump has threatened “very severe consequences” if his Russian counterpart doesn’t agree to a ceasefire at the summit, being hosted at a remote US army base in snowy Anchorage, Alaska.

Follow latest updates from Ukraine war

But there are fears they will discuss a deal robbing Ukraine of the land currently occupied by Russia – something Volodymyr Zelenskyy has said he won’t accept.

Here’s what three of our correspondents think ahead of the much-anticipated face-to-face.

Putin’s legacy is at stake – he’ll want territory and more
By Ivor Bennett, Moscow correspondent

Putin doesn’t just want victory. He needs it.

Three and a half years after he ordered the invasion of Ukraine, this war has to end in a visible win for the Russian president. It can’t have been for nothing. His legacy is at stake.

So the only deal I think he’ll be willing to accept at Friday’s summit is one that secures Moscow’s goals.

These include territory (full control of the four Ukrainian regions which Russia has already claimed), permanent neutrality for Kyiv and limits on its armed forces.

I expect he’ll be trying to convince Trump that such a deal is the quickest path to peace. The only alternative, in Russia’s eyes, is an outright triumph on the battlefield.

Vladimir Putin and Donald Trump meeting in Osaka in 2019
Image:
Vladimir Putin and Donald Trump meeting in Osaka in 2019

I think Putin‘s hope is that the American president agrees with this view and then gives Ukraine a choice: accept our terms or go it alone without US support.

A deal like that might not be possible this week, but it may be in the future if Putin can give Trump something in return.

That’s why there’s been lots of talk from Moscow this week about all the lucrative business deals that can come from better US-Russia relations.

The Kremlin will want to use this opportunity to remind the White House of what else it can offer, apart from an end to the fighting.

Read more:
What could Ukraine be asked to give up?
Trump-Putin summit starting to feel quite ‘Midnight Sun’

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What will Kyiv be asked to give up?

Ukraine would rather this summit not be happening
By Dominic Waghorn
, international affairs editor

Ukraine would far rather this meeting wasn’t happening.

Trump seemed to have lost patience with Putin and was about to hit Russia with more severe sanctions until he was distracted by the Russian leader’s suggestion that they meet.

Ukrainians say the Alaska summit rewards Putin by putting him back on the world stage.

But the meeting is happening, and they have to be realistic.

Most of all, they want a ceasefire before any negotiations can happen. Then they want the promise of security guarantees.

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Does Europe have any power over Ukraine’s future?

That is because they know that Putin may well come back for more even if peace does break out. They need to be able to defend themselves should that happen.

And they want the promise of reparations to rebuild their country, devastated by Putin’s wanton, unprovoked act of aggression.

There are billions of Russian roubles and assets frozen across the West. They want them released and sent their way.

What they fear is Trump being hoodwinked by Putin with the lure of profit from US-Russian relations being restored, regardless of Ukraine’s fate.

US Army paratroopers train at the military base where discussions will take place. File pic: Reuters
Image:
US Army paratroopers train at the military base where discussions will take place. File pic: Reuters

That would allow Russia to regain its strength, rearm and prepare for another round of fighting in a few years’ time.

Trump and his golf buddy-turned-negotiator Steve Witkoff appear to believe Putin might be satisfied with keeping some of the land he has taken by force.

Putin says he wants much more than that. He wants Ukraine to cease to exist as a country separate from Russia.

Any agreement short of that is only likely to be temporary.

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Zelenskyy: I told Trump ‘Putin is bluffing’

Trump’s pride on the line – he has a reputation to restore
By
Martha Kelner, US correspondent

As with anything Donald Trump does, he already has a picture in his mind.

The image of Trump shaking hands with the ultimate strongman leader, Vladimir Putin, on US soil calls to his vanity and love of an attention-grabbing moment.

There is also pride at stake.

Joint Base Elmendorf-Richardson in Alaska, where Trump will meet his Russian counterpart. File pic: Reuters
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Joint Base Elmendorf-Richardson in Alaska, where Trump will meet his Russian counterpart. File pic: Reuters

Trump campaigned saying he would end the Russia-Ukraine war on his first day in office, so there is an element of him wanting to follow through on that promise to voters, even though it’s taken him 200-plus days in office and all he’s got so far is this meeting, without apparently any concessions on Putin’s end.

In Trump’s mind – and in the minds of many of his supporters – he is the master negotiator, the chief dealmaker, and he wants to bolster that reputation.

He is keen to further the notion that he negotiates in a different, more straightforward way than his predecessors and that it is paying dividends.

So far, despite sanctions on Russia, despite warnings and deadlines, the situation in Ukraine is only getting worse.

He’s hoping that this meeting, simply the act of sitting down with Putin, can change the tide.

The Russian president may have different ideas.

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Trump’s targets for Putin summit appear fluid – can he even get a ceasefire?

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Trump's targets for Putin summit appear fluid - can he even get a ceasefire?

The “if” was doing some heavy lifting.

Mr Trump floated the idea of a second meeting, this one between Putin, Zelenskyy and possibly himself, “if” the Alaska summit goes well.

Speaking to European leaders earlier, in a virtual call he rated at “10” and “very friendly”, he’d shared his intention to try to broker a ceasefire on Friday.

So, the strategy is crystallising – he will press for a trilateral meeting to discuss territory “if” he manages to secure a truce during the bilateral meeting.

But that begs the obvious question: what if he can’t?

The US president is keeping his options open – rating the chance of a second meeting as “very good” but preparing the ground for failure too.

“There may be no second meeting because if I feel that it is not appropriate to have it because I didn’t get the answers that we have to have, then we’re not going to have a second meeting,” he said.

More on Russia

Unusually, given how often he talks about his abilities, he conceded that he may not persuade Vladimir Putin to stop targeting civilians.

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Sky’s defence analyst, Prof Michael Clarke, looks at what land Ukraine might be asked to give up when Donald Trump meets Vladimir Putin on Friday in Alaska.

Read More
Trump’s threat to Putin – Ukraine latest
What could Ukraine be asked to give up?
Sky News’ Ukraine Q&A

But without elaborating on what any sanctions might be, he warned that Russia would face “very severe consequences” if it doesn’t end the war.

Even if he achieves the seemingly impossible – a halt to the fighting – there seems little chance of agreement on any swapping of territory.

A BTR-4 armoured personnel carrier during military exercises in Kharkiv region.
Image:
A BTR-4 armoured personnel carrier during military exercises in Kharkiv region.

Mr Zelenskyy has told Mr Trump that Putin “is bluffing” and wants to “push forward along the whole front” not return land.

In the space of a week, Donald Trump has gone from talking about a land-swapping deal, to a “listening exercise”, to the potential for a ceasefire.

His expectations appear changeable, an indication of how fluid back-room negotiations are in the run-up to his first face-to-face with Vladimir Putin in six years.

He described Friday’s summit as “setting the table for a second meeting”, but that’s presumptuous when the meal – or deal – isn’t cooked yet.

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Technology

Google faces loss of Chrome as Perplexity bid adds drama to looming breakup decision

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Google faces loss of Chrome as Perplexity bid adds drama to looming breakup decision

Sundar Pichai, chief executive officer of Alphabet Inc., during a visit to the Google for Startups campus in Warsaw, Poland, on Thursday, Feb. 13, 2025. The EU has established a reputation globally for its aggressive regulation of major technology companies, including the likes of Apple and Google over antitrust concerns. Photographer: Damian Lemanski/Bloomberg via Getty Images

Damian Lemanski | Bloomberg | Getty Images

Perplexity AI’s bid on Tuesday to buy Google’s Chrome browser for $34.5 billion represents a dramatic moment for the internet search giant, a week before it celebrates the 20th anniversary of its IPO.

Even if analysts aren’t taking the offer very seriously, Perplexity’s move marks a turning point. It’s the first time an outside party has made such a public and specific effort to strip out a key piece of Google, which is currently awaiting a judge’s decision on whether it must take significant divestiture steps following a ruling last year that the company has held a monopoly in its core search market.

The ruling was widely viewed as the most important antitrust decision in the tech industry since the case against Microsoft more than two decades ago. The U.S. Department of Justice, which filed the landmark case against Google in 2020, indicated after its victory in court that it was considering a possible breakup of Google as an antitrust remedy.

Soon after that, the DOJ explicitly called for Google to divest Chrome to create a more equal playing field for search competitors. As is, Google bundles search and other services into Chrome and preinstalls the browser on Chromebooks. Google Legal Chief Kent Walker said in response to the DOJ that its “approach would result in unprecedented government overreach” and would harm the country’s effort to maintain economic and tech leadership.

With the remedies decision expected this month, investors have a lot to consider regarding the future value of Google and parent Alphabet. The company is shelling out tens of billions of dollars a year on artificial intelligence infrastructure and AI services while facing the risk that consumers will be spending a lot less time on traditional search as ChatGPT and other AI-powered alternatives provide new ways to access information.

But while Alphabet still counts on search-related ads for the majority of its revenue, the company has been diversifying over the past decade. October will mark 10 years since the creation of Alphabet as a holding company, with Google as its prime subsidiary.

“This new structure will allow us to keep tremendous focus on the extraordinary opportunities we have inside of Google,” co-founder Larry Page said in a blog post at the time.

Page moved from CEO of Google to become chief executive of Alphabet, promoting Sundar Pichai, who had been a senior vice president in charge of internet businesses, to run Google. Four years later, Pichai replaced Page as Alphabet CEO.

On Pichai’s watch, Alphabet’s market cap has jumped more than 150% to $2.5 trillion. With an increasingly dominant position on the internet, Pichai and team have had to continue looking for growth areas, particularly in AI, while simultaneously fending off an aggressive set of regulators in the U.S. and Europe.

Analysts have taken the opportunity to place estimated values on Alphabet’s various businesses, partly in the event that the company is ever forced into drastic measures. Some have even suggested it could be a good thing for shareholders.

“We believe the only way forward for Alphabet is a complete breakup that would allow investors to own the business they actually want,” analysts at D.A. Davidson have written in a series of notes this year.

Alphabet didn’t respond to a request for comment.

Here’s a breakdown of how some analysts value Alphabet’s top non-search assets:

Chrome

Perplexity offers $34.5 billion for Google Chrome

The browser is key to Alphabet’s ad business, which uses data from Chrome to help with targeted advertisements. Google originally launched Chrome in 2008 as an effort to “add value for users and, at the same time, help drive innovation on the web.”

Perplexity’s offer doesn’t stack up to analyst estimates, but it’s still much higher than Perplexity’s own valuation, which reached $18 billion in July. Perplexity, which is best known for its AI-powered search engine that gives users simple answers to inquiries, said investors are on board to foot the bill. However, the company didn’t name the prospective backers.

Barclays analysts called the possibility of a Chrome divestiture a “black swan” risk, warning of a potential 15% to 25% drop in Alphabet’s stock should it occur. They estimate that Chrome drives around 35% of Google’s search revenue.

If a deal for Chrome is on the table, analysts at Raymond James value the browser at $50 billion, based on 2.25 billion users and Google’s revenue share agreements with phone manufacturers that preinstall Chrome on devices.

That’s inline with where Gabriel Weinberg, CEO of rival search company DuckDuckGo, values Chrome. Weinberg, who testified in the antitrust trial, said in April that Chrome could be sold for up to $50 billion if a spinout was required. Weinberg said his estimate was based on “back-of-the-envelope” math, looking at Chrome’s user base.

Bob O’Donnell of market research firm TECHnalysis Research, cautioned that Chrome is “not directly monetizable,” because it serves as a gateway and that it’s “not clear how you measure that from a pure revenue-generating perspective.”

Google Cloud

A person takes a photo of the Google Cloud logo, during the 2025 Mobile World Congress (MWC) in Barcelona, Spain, March 4, 2025. 

Albert Gea | Reuters

Google’s cloud unit, which is third in the cloud infrastructure market behind Amazon Web Services and Microsoft Azure, is one of Alphabet’s key growth engines and its biggest business outside of digital advertising.

Google began its big push into the market about a decade ago, even though it officially launched what was called the Google Cloud Platform (GCP) in 2011. The unit was rebranded as just Google Cloud in 2016.

Like AWS and Azure, Google Cloud generates revenue from businesses ranging from startups to large enterprises that run workloads on the company’s servers. Additionally, customers pay for products like Google Workspace, the company’s suite of productivity apps and collaboration tools.

In 2020, Google began breaking out its cloud business in financial statements, starting with revenue. In the fourth quarter of 2020, the first time Google included profit metrics for the unit, it recorded an operating loss of $1.24 billion.

The business turned profitable in 2023, and is now generating healthy margins. In the second quarter of 2025, Google reported an operating profit for the cloud business of $2.8 billion on revenue of $13.6 billion. Demand is so high that the company’s cloud services now have a backlog, a measure of future committed revenue, of $106 billion, CFO Anat Ashkenazi said on the earnings call.

In March, Google agreed to acquire cloud security vendor Wiz for $32 billion, the company’s largest deal ever.

Analysts at Wedbush Securities value Google’s cloud at $602 billion, while TD Cowen in May put the number at about $549 billion. For Raymond James, the valuation is $579 billion.

D.A. Davidson analysts, who have the highest ascribed valuation at $682 billion, and TD Cowen analysts note that while Google still trails AWS and Azure, it’s growing faster than Amazon’s cloud business and has the potential for a premium valuation. That’s based on its AI infrastructure, strong data analytics stack, and ability to capture more enterprise business.

It would be “one of the best standalone software stocks,” D.A. Davidson analysts wrote in July.

YouTube

A Youtube podcast microphone is seen at the Variety Podcasting Brunch Presented By YouTube at Austin Proper Hotel in Austin, Texas, on March 8, 2025.

Mat Hayward | Variety | Getty Images

Google’s $1.65 billion purchase of YouTube in 2006 is generally viewed as one of the best acquisitions ever by an internet company, alongside Facebook’s $1 billion deal for Instagram in 2012.

YouTube is the largest video site on the web and a big part of Google’s ad business. In the second quarter, YouTube ad revenue increased 13% to $9.8 billion, accounting for 14% of Google’s total ad sales.

Valuation estimates vary tremendously.

Dubbing it the “new king of all media,” MoffettNathanson values YouTube at between $475 billion and $550 billion, arguing that it’s larger and more powerful than any other player in Hollywood. At the top end of that range, YouTube would be worth about 22% of all of Alphabet.

YouTube recently overtook Netflix, which has a market cap of $515 billion, as the top streaming platform in terms of audience engagement.

TD Cowen analysts ascribe a much lower valuation at $271 billion. The firm notes that it’s one of six Google products with more than 2 billion monthly users, along with search, Google Maps, Gmail, Android and Chrome. Raymond James says YouTube is worth $306 billion.

For 2024, YouTube was the second-largest media company by revenue at $54.2 billion, trailing only Disney. The platform earns revenue from advertising and subscriptions.

The TD Cowen analysts said in May that they expect ad revenue to climb about 14% this year, and they expect the unit to maintain a double-digit growth rate. There’s also a fast-growing subscription side that includes YouTube TV, music and NFL Sunday ticket.

Waymo

Waymo begins testing self-driving cars with human drivers in New York and Philadelphia

Alphabet’s self-driving car company, Waymo, is by far its most high-profile success so far outside of Google.

Waymo currently operates the largest commercial autonomous ride-hailing fleet in the U.S., with more than 1,500 cars and over 100 million fully driverless miles logged. Rivals like Tesla and Amazon’s Zoox are still mostly at the testing phase in limited markets.

When Alphabet was formed as Google’s parent company, it created an “Other Bets” category to include businesses that it liked to call “moonshots,” a term that had already made its way into Google lexicon.

“We won’t become complacent, relying solely on small tweaks as the years wear on,” the company wrote in its 2014 annual report, describing its moonshot projects.

Waymo was spun out of Google in 2016 to join Other Bets, which on the whole is still losing billions of dollars a year. In the second quarter, Alphabet recorded a loss for the category of $1.2 billion on $373 million in revenue.

In its most recent funding round in November, Waymo was valued at $45 billion. The transaction included outside investors Andreessen Horowitz, Tiger Global, Silver Lake, Fidelity and T. Rowe Price. 

Some analysts see the unit worth many multiples of that now. D.A. Davidson analysts estimated the valuation at $200 billion or more earlier this month. Oppenheimer assigned a base case valuation of $300 billion, on the assumption that it generates $102 billion in adjusted earnings by 2040.

Raymond James values Waymo at $150 billion, with a prediction that rides per week will reach 1.4 million in 2027 and climb to 5.8 million by 2030. TD Cowen estimated Waymo’s enterprise mid-point value at $60 billion.

Waymo says it now conducts more than 250,000 paid weekly trips in the markets where it operates commercially, including Atlanta, Austin, Los Angeles, Phoenix and San Francisco. The company said it would be expanding to Philadelphia, Dallas and elsewhere.

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Alphabet’s 10-year anniversary comes as DOJ decision looms, breakup chatter builds

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