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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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Why the worst leaders sometimes rise the fastest

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History is crowded with CEOs who have flamed out in very public ways. Yet when the reckoning arrives, the same question often lingers: How did this person keep getting promoted? In corporate America, the phenomenon is known as “failing up,” the steady rise of executives whose performance rarely matches their trajectory. Organizational psychologists say it’s not an anomaly. It’s a feature of how many companies evaluate leadership.

At the core is a well-documented bias toward confidence over competence. Studies consistently show that people who speak decisively, project certainty, and take credit for wins—whether earned or not—are more likely to be perceived as leadership material. In ambiguous environments, boards and senior managers often mistake boldness for ability. As long as a leader can narrate failure convincingly—blaming market headwinds, legacy systems, or uncooperative teams—their upward momentum may continue.

Another driver is asymmetric accountability. Senior executives typically oversee vast, complex systems where outcomes are hard to tie directly to individual decisions. When results are good, credit flows upward. When results are bad, blame diffuses downward, and middle managers, project leads, and market conditions become convenient shock absorbers. This allows underperforming leaders to survive long enough to secure their next promotion.

Then there’s the mobility illusion. In many industries, frequent job changes are read as ambition and momentum rather than warning signs. An executive who leaves after short, uneven tenures can reframe each exit as a “growth opportunity” or a strategic pivot. Recruiters and boards, under pressure to fill top roles quickly, often rely on résumé signals, like brand-name firms, inflated titles, and elite networks, rather than deep performance audits.

Ironically, early visibility can also accelerate failure upward. High-profile roles magnify both success and failure, but they also increase name recognition. An executive who runs a troubled division at a global firm may preside over mediocre results, yet emerge with a reputation as a “big-company leader,” making them attractive for a CEO role elsewhere.

The reckoning usually comes only at the top. As CEO, the buffers disappear. There is no one left to blame, and performance is judged in the blunt language of earnings, stock price, profitability, or layoffs. The traits that once fueled ascent, such as overconfidence, risk-shifting, and narrative control, become liabilities under full scrutiny.

The central lesson for aspiring CEOs is that the very system that rewards confidence, visibility, and narrative control on the way up often masks weak execution until the top job strips those protections away. Future leaders who want to avoid “failing upward” must deliberately build careers grounded in verifiable results and direct ownership of outcomes because at the CEO level, there is no narrative strong enough to substitute for performance.

Ruth Umoh
ruth.umoh@fortune.com

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Investors are questioning OpenAI’s profitability amid its massive spending while increasingly viewing Alphabet as the deeper-pocketed winner in the AI race. Fortune

Trump warned that Netflix’s $72 billion bid for Warner Bros. Discovery could face antitrust scrutiny, suggesting it would create an overly dominant force in streaming. Fortune

An etiquette camp is trying to help Silicon Valley shed its sloppy image by teaching tech elites how to dress and behave as their influence grows. WaPo

IBM is reportedly in advanced talks to buy data-infrastructure firm Confluent for about $11 billion, bolstering its AI data capabilities. WSJ

Even as women reach top roles in politics and business at record levels, public confidence in their leadership is stagnating or declining. Bloomberg

Terence “Bud” Crawford, the undefeated 38-year-old boxing champion, has earned more than $100 million and even turned Warren Buffett into a fan. Forbes

Big Tech leaders now warn that artificial intelligence is advancing to the point where it could begin replacing even CEOs, reshaping the very top of corporate leadership. WSJ

This is the web version of the Fortune Next to Lead newsletter, which offers strategies on how to make it to the corner office. Sign up for free.



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The workforce is becoming AI-native. Leadership has to evolve

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One of the most insightful conversations I have had recently about artificial intelligence was not with policymakers or peers. It was with a group of Nokia early-careers talents in their early 20s. What stood out was their impatience. They wanted to move faster in using AI to strengthen their innovation capabilities. 

That makes perfect sense. This generation began university when ChatGPT launched in 2022. They now account for roughly half of all ChatGPT usage, applying it to everything from research to better decision-making in knowledge-intensive work. 

Some people worry that AI-driven hiring slowdowns are disproportionately impacting younger workers. Yet the greater opportunity lies in a new generation of AI-native professionals entering the workforce equipped for how technology is transforming roles, teams, and leadership.

Better human connectivity 

One of the first tangible benefits of generative AI is that it allows individual contributors to take on tasks once handled by managers. Research by Harvard Business School found that access to Copilot increased employee productivity by 5% in core tasks. As productivity rises and hierarchies flatten, early-career employees using AI are empowered to focus on outcomes, learn faster, and contribute at a higher level.

Yet personal productivity is not the real measure of progress. What matters most is how well teams perform together. Individual AI gains only create business impact when they align with team goals and that requires greater transparency, alignment, and accountability.

At Nokia, we ensure that everyone has clear, measurable goals that support their teams’ objectives. Leaders need to be open about their goals to their managers and to their reports. And everyone means everyone. Me included. That way goals are not only about recognition and reward. They become an ongoing dialogue between leaders and their teams. It’s how we’re building a continuous learning culture that thrives on feedback and agility, both essential in the AI era. 

Humans empowered with AI, not humans versus AI

AI’s true power lies in augmenting human skills. Every role has a core purpose – whether in strategy, creativity, or technical problem-solving – and AI helps people focus on that. 

During the COVID-19 pandemic, more than 60 chatbots were deployed in 30 countries to handle routine public health queries, freeing up healthcare workers to focus on critical patient care. Most health services never looked back. 

The same pattern applies inside companies. Some of the routine tasks given to new hires are drudge work and not a learning experience. AI gives us a chance to rethink the onboarding, training, and career development process.

Take an early-career engineer. Onboarding can be a slow process of documentation and waiting for reviews. AI can act as an always-on coach that gives quick guidance and helps people ramp up. Mentors then spend less time on the basics and more time helping engineers solve real problems. Engineers can also have smart agents testing their designs, ideas, and simulating potential outcomes. In this way, AI strengthens, rather than substitutes, the human connection between junior engineers and their mentors and helps unlock potential faster.

Encourage experimentation and entrepreneurship 

During two decades of the Internet Supercycle (1998-2018), start-ups created trillions of dollars in economic value and roughly half of all new jobs in OECD countries

As AI lowers the barriers to launching and scaling ventures, established companies must find new ways to encourage experimentation, nurture innovation through rapid iterations, and give employees the chance to commercialize and scale their ideas.

There is a generational shift that increases the urgency: more than 60% of Gen Z Europeans hope to start their own businesses within five years, according to one survey. To secure this talent, large organizations must provide the attributes that make entrepreneurship attractive. Empowering people with agility, autonomy, and faster decision-making creates an edge in attracting and keeping top talent.

At Nokia, our Technology and AI Organization is designed to strengthen innovation capabilities, encourage entrepreneurial thinking, and give teams the support to turn ideas into real outcomes.

More coaching, less managing 

Sporting analogies are often overused in business as the two worlds don’t perfectly align, yet the evolution of leadership in elite football offers useful lessons. Traditionally, managers oversaw everything on and off the pitch. Today, head coaches focus on building the right team and culture to win. 

Luis Enrique, the manager of Paris-St. Germain football club, last season’s UEFA Champion’s League winner, exemplifies this shift. He transformed a team of stars into a star team, while also evolving his coaching style, elevating both individual and collective potential.

Of course, CEOs must switch between both roles (as I said, the worlds don’t perfectly align) – setting vision and strategy while also cultivating the right team and culture to succeed. AI can help leaders do both with more focus. It gives us quicker insight into what is working, what is not, and where teams need support.

I have been testing these tools with my own leadership team. We are using generative AI to help us evaluate our decisions and to understand how we work together. It has revealed patterns we might have missed, and it has helped us get to the real issues faster. It does not replace judgment or experience. It supports them.

Yet the core of leadership does not change. AI cannot build trust. It cannot set expectations. It cannot create a culture that learns, improves, and takes responsibility. That still comes from people. And in a world shaped by AI, the leaders who succeed will be the ones who coach, who listen, and who help teams move faster with confidence.

Nokia’s technology connects intelligence around the world. Inside the company, connecting intelligence is about how people work together. It means giving teams the tools, support and culture they need to grow and perform with confidence. Connecting intelligence is how teams win.

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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Procurement execs often don’t understand the value of good design, experts say

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Behind every intricately designed hotel or restaurant is a symbiotic collaboration between designer and maker.

But in reality, firms want to build more with less—and even though visions are created by designers, they don’t always get to see them to fruition. Instead, intermediaries may be placed in charge of procurements and overseeing the financial costs of executing designs.

“The process is not often as linear as we [designers] would like it to be, and at times we even get slightly cut out, and something comes out on the other side that wasn’t really what we were expecting,” said Tina Norden, a partner and principal at design firm Conran and Partners, at the Fortune Brainstorm Design forum in Macau on Dec. 2.

“To have a better quality product, communication is very much needed,” added Daisuke Hironaka, the CEO of Stellar Works, a furniture company based in Shanghai. 

Yet those tasked with procurement are often “money people” who may not value good design—instead forsaking it to cut costs. More education on the business value of quality design is needed, Norden argued.

When one builds something, she said, there are both capital investment and a lifecycle cost. “If you’re spending a bit more money on good quality furniture, flooring, whatever it might be, arguably, it should last a lot longer, and so it’s much better value.”

Investing in well-designed products is also better for the environment, Norden added, as they don’t have to be replaced as quickly.

Attempts to cut costs may also backfire in the long run, said Hironaka, as business owners may have to foot higher maintenance bills if products are of poor design and make.

AI in interior and furniture design

Though designers have largely been slow adopters of AI, some luminaries like Daisuke are attempting to integrate it into their team’s workflow.

AI can help accelerate the process of designing bespoke furniture, Daisuke explained, especially for large-scale projects like hotels. 

A team may take a month to 45 days to create drawings for 200 pieces of custom-made furniture, the designer said, but AI can speed up this process. “We designed a lot in the past, and if AI can use these archives, study [them] and help to do the engineering, that makes it more helpful for designers.” 

Yet designers can rest easy as AI won’t ever be able to replace the human touch they bring, Norden said. 

“There is something about the human touch, and about understanding how we like to use our spaces, how we enjoy space, how we perceive spaces, that will always be there—but AI should be something that can assist us [in] getting to that point quicker.”

She added that creatives can instead view AI as a tool for tasks that are time-consuming but “don’t need ultimate creativity,” like researching and three-dimensionalizing designs.

“As designers, we like to procrastinate and think about things for a very long time to get them just right, [but] we can get some help in doing things faster.”



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