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Paul Newman and Yvon Chouinard’s footsteps: More ways for CEOs to give it away in ‘Great Boomer Fire Sale’

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The most radical act in capitalism today isn’t launching a unicorn startup or orchestrating a multi-billion-dollar IPO – it’s giving your company away in service of good.

While some business leaders are focused on how to make their fortunes in AI or crypto, others are choosing to walk away with nothing except what matters most: a philanthropic annuity to cement their legacy. As the President and CEO of one of the most famous brands that gives 100% of its profits away, I am hearing from more and more CEOs and business owners who want to follow in Paul Newman or Yvon Chouinard’s footsteps. These leaders spent decades building profitable enterprises and are now working to transfer ownership of their companies, not to the highest bidder, but to foundations, nonprofits, purpose-driven trusts, or to their employees.

An estimated 2.9 million private U.S. businesses are owned by those over 55. Over the next 20 years, the Great Wealth Transfer and “The Great Boomer Fire Sale” is a unique opportunity to reimagine business exits as an act of generosity. 

Why give away your business? A generosity exit allows you to maximize your giving through an engine that will keep generating profits every year, creating a philanthropic annuity, while preserving the company, its employees, and the culture built over decades. Besides, conventional exit options may not be a great fit for your values if you’ve spent decades investing in your employees and your community. Selling to private equity or another business could mean layoffs and a decimated culture. Not all owners have family heirs who want or can take over. Going public is only available to the biggest businesses and subjects your life’s work to quarterly earnings pressures and the short-term thinking that comes along with it. Purpose and legacy can be more important than a big check at the end of your life, especially if you already made good money throughout your life’s work. 

As the baby boomer generation looks to the legacy they want to leave behind, Millennials and Gen Z look ahead to the legacies they want to build, with some founding successful companies where giving 100% of their profits away is baked in from the beginning. Entrepreneurs like John and Hank Green of The Good Store, and Adam McCurdie and Joshua Ross of Humanitix, are challenging the critics of the ‘business for good’ model by showing that you can grow a successful business while simultaneously giving away all profits.

The good news for those interested in giving away their business? There are now more governance models available than ever before. 

Choosing the Right Structure for Your Exit

Through the passage of the Philanthropic Enterprise Act in 2018, foundations can now own 100% for-profit companies in the US. Newman’s Own Foundation is an example of this. As a result, one hundred percent of profits and royalties from sales of Newman’s Own products go to the Foundation in service of its mission: to nourish and transform the lives of children who face adversity. 

Patagonia uses a perpetual purpose trust, a type of steward-owned ownership which is more common in Europe. Since 2022, the trust holds 100% of the company’s voting stock to ensure its environmental mission and values are preserved indefinitely, while profits are funnelled to a 501c(4), Holdfast Collective to give away to climate causes. These models create what economists call “lock-in effects” allowing owners to keep mission front and center, even when they’re gone.

Over 6,500 U.S. companies are now fully or part-owned by their workers, using Employee Stock Ownership Plans (ESOPs), including Bob’s Red Mill and King Arthur Baking Company. These models support business continuity and create thousands of employee-owners who are invested in the company’s long-term success. While in many cases, these exits are financed through loans, there’s nothing stopping an owner from giving the business to their workers.

You can also look at hybrid models. For example, Organic Grown Company uses a perpetual purpose trust to ensure profits are split between equity investors, employees, growers, and nonprofits.

And while a business owner may decide to establish their own foundation, why reinvent the wheel? There are plenty of existing foundations and non-profits who could be worthy recipients if you want to give your company away. Back in 2011, Amar Bose gave the majority of the stock of the sound system company Bose corporation to his alma mater, the Massachusetts Institute of Technology in the form of non-voting shares.

What’s Next? 

This holiday season is upon us, and whether you own a business or not, it’s a good time to reflect on what matters most: What are your values? How much money is enough for yourself and your family? What does legacy mean to you?

For CEOs and owners considering a generosity exit, the first step is to assemble the right team: attorneys experienced in foundation-ownership, purpose trusts, or ESOPs, financial advisors who understand tax implications of these unique paths, independent directors or trustees who share your vision. Organizations like 100% for Purpose, Purpose Trust Ownership Network, and Purpose Foundation can provide resources and case studies.

Start mapping out your plan, and be patient as a transition could take years, not months. Yvon Chouinard spent two years structuring Patagonia’s transition. While Paul Newman decided from the beginning to give all of the food company’s profits away back when it began in 1982, the first few years were just him writing checks at the end of the year. A foundation was initially established in 1998, and became Newman’s Own Foundation before Paul’s death, at which point the food company was gifted to the Foundation. The complexity isn’t just legal—it’s emotional, relational, and cultural, but ideally, the transition can happen while you’re still actively involved, can steward the shift, and can see the rewards of your hard labor pay dividends for good. 

In this day and age of robots and artificial intelligence, it’s good to remember Paul Newman’s wise words: “Corporations are not inhuman money machines. They must accept that they exist inside a community. They have a moral responsibility to be involved. They can’t just sit there without acknowledging that there’s stuff going on around them.”

Building a profitable company is hard but what’s truly meaningful is to let them go in service of good. In doing so, we allow our work to live on in ways that matter far beyond the balance sheet.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.



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HP’s chief commercial officer predicts the future will include AI PCs that don’t use the cloud

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Increased focus on “privacy and security” may open the door for AI-enabled devices rather than rely entirely on cloud computing and remote data centers. 

“In a world where sovereign data retention matters, people want to know that if they input data to a model, the model won’t train on their data,” David McQuarrie, HP’s chief commercial officer, told Fortune in October. Using an AI locally provides that reassurance.

HP, like many of its devicemaking peers, is exploring the use of AI PCs, or devices that can use AI locally as opposed to in the cloud. “Longer term, it will be impossible not to buy an AI PC, simply because there’s so much power in them,” he said. 

More broadly, smaller companies might be served just as well by a smaller model running locally than a larger model running in the cloud. “A company, a small business, or an individual has significant amounts of data that need not be put in the cloud,” he said. 

Asian governments have often had stricter rules on data sovereignty. China, in particular, has significantly tightened its regulations on where Chinese user data can be stored. South Korea is another example of an Asian country that treats some locally sourced data as too sensitive to be housed overseas. 

Governments the world over, and particularly in Asia, are also investing in local sovereign AI capabilities, trying to avoid relying entirely on systems and platforms housed wholly overseas. South Korea, for example, is partnering with local tech companies like search giant Naver to build its own AI systems. Singapore is investing in projects like the Southeast Asian Languages in One Network (SEA-LION), which are better tailored to Southeast Asian countries. 

Asian AI adoption

Asia is HP’s smallest region, but also its fastest-growing. Revenue from Asia-Pacific and Japan grew by 7% over the company’s 2025 fiscal year, which ended in October, to hit $13.3 billion. That’s around a quarter of HP’s total revenue of $55.3 billion. (HP’s other two regions are the Americas; and Europe, the Middle East, and Africa.)

McQuarrie also suggested that there was an opportunity to be “disruptive” in Asia. While many business leaders have been eager to embrace AI, at least rhetorically, actual adoption is proving more difficult. A recent survey from McKinsey reports that two-thirds of companies are still in the experimentation phase of AI. 

But McQuarrie believed that AI adoption in Asia could be “just as quick, if not quicker,” than other regions. 

Asia seems to be more comfortable with the use of AI, at least when it comes to users. An October survey from Pew found that fewer people in countries like India, South Korea and Japan reported feeling “more concerned than excited” about AI compared to the U.S. 

When it comes to convincing more companies to adopt AI, let alone AI PCs, McQuarrie said the answer was to make AI functions as seamless as possible, so “that it doesn’t really matter whether you understand that you’re embracing AI or not.”

“What we’re doubling down on is the future of work,” McQuarrie said. “The future of work is a device that makes your experience better and your productivity greater.”

“The fact that we’re using AI in the background? They don’t need to know that.”



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Trump administration waives part of a Biden-era fine against Southwest Air for canceled flights

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The U.S. Department of Transportation is waiving part of a fine assessed against Southwest Airlines after the company canceled thousands of flights during a winter storm in 2022.

Under a 2023 settlement reached by the Biden administration, Southwest agreed to a $140 million civil penalty. The government said at the time that the penalty was the largest it had ever imposed on an airline for violating consumer protection laws.

Most of the money went toward compensation for travelers. But Southwest agreed to pay $35 million to the U.S. Treasury. Southwest made a $12 million payment in 2024 and a second $12 million payment earlier this year. But the Transportation Department issued an order Friday waiving the final $11 million payment, which was due Jan. 31, 2026.

The department said Southwest should get credit for significantly improving its on-time performance and investing in network operations.

“DOT believes that this approach is in the public interest as it incentivizes airlines to invest in improving their operations and resiliency, which benefits consumers directly,” the department said in a statement. “This credit structure allows for the benefits of the airline’s investment to be realized by the public, rather than resulting in a government monetary penalty.”

The fine stemmed from a winter storm in December 2022 that paralyzed Southwest’s operations in Denver and Chicago and then snowballed when a crew-rescheduling system couldn’t keep up with the chaos. Ultimately the airline canceled 17,000 flights and stranded more than 2 million travelers.

The Biden administration determined that Southwest had violated the law by failing to help customers who were stranded in airports and hotels, leaving many of them to scramble for other flights. Many who called the airline’s overwhelmed customer service center got busy signals or were stuck on hold for hours.

Even before the settlement, the nation’s fourth-biggest airline by revenue said the meltdown cost it more than $1.1 billion in refunds and reimbursements, extra costs and lost ticket sales over several months.



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Trump slams Democratic congressman as disloyal for not switching parties after pardon

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Trump blasted Cuellar for “Such a lack of LOYALTY,” suggesting the Republican president might have expected the clemency to bolster the GOP’s narrow House majority heading into the 2026 midterm elections.

Cuellar, in a television interview Sunday after Trump’s social media post, said he was a conservative Democrat willing to work with the administration “to see where we can find common ground.” The congressman said he had prayed for the president and the presidency at church that morning “because if the president succeeds, the country succeeds.”

Citing a fellow Texas politician, the late President Lyndon Johnson, Cuellar said he was an American, Texan and Democrat, in that order. “I think anybody that puts party before their country is doing a disservice to their country,” he told Fox News Channel’s “Sunday Morning Futures.”

Trump noted on his Truth Social platform that the Democratic President Joe Biden’s administration had brought the charges against Cuellar and that the congressman, by running once more as a Democrat, was continuing to work with “the same RADICAL LEFT” that wanted him and his wife in prison — “And probably still do!”

“Such a lack of LOYALTY, something that Texas Voters, and Henry’s daughters, will not like. Oh’ well, next time, no more Mr. Nice guy!” Trump said. Cuellar’s two daughters, Christina and Catherine, had sent Trump a letter in November asking that he pardon their parents.

Trump explained his pardon he announced Wednesday as a matter of stopping a “weaponized” prosecution. Cuellar was an outspoken critic of Biden’s immigration policy, a position that Trump saw as a key alignment with the lawmaker.

Cuellar said he has good relationships within his party. “I think the general Democrat Caucus and I, we get along. But they know that I’m an independent voice,” he said.

A party switch would have been an unexpected bonus for Republicans after the GOP-run Legislature redrew the state’s congressional districts this year at Trump’s behest. The Texas maneuver started a mid-decade gerrymandering scramble playing out across multiple states. Trump is trying to defend Republicans’ House majority and avoid a repeat of his first term, when Democrats dominated the House midterms and used a new majority to stymie the administration, launch investigations and twice impeach Trump.

Yet Cuellar’s South Texas district, which includes parts of metro San Antonio, was not one of the Democratic districts that Republicans changed substantially, and Cuellar believes he remains well-positioned to win reelection.

Federal authorities had charged Cuellar and his wife with accepting thousands of dollars in exchange for the congressman advancing the interests of an Azerbaijan-controlled energy company and a bank in Mexico. Cuellar was accused of agreeing to influence legislation favorable to Azerbaijan and deliver a pro-Azerbaijan speech on the floor of the U.S. House.

Cuellar has said he his wife were innocent. The couple’s trial had been set to begin in April.

In the Fox interview, Cuellar insisted that federal authorities tried to entrap him with “a sting operation to try to bribe me, and that failed.”

Cuellar still faces a House Ethics Committee investigation.



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