Thompson, chairman of the Chief Executive Alliance and previously ranked as the world’s top CEO coach, and Loflin, Nasdaq’s Global Head of Board Advisory, joined forces to provide a 360-view of this loaded moment for leadership, from the C-suite and board perspectives, respectively. In a wide-ranging conversation with Fortune, they talked about the Shakespearean themes of leadership and turmoil and the feeling that “heavy is the head that wears the crown.”

For those aspiring to reach the top, Thompson shared the conventional wisdom he’d learned from his mentor, Marshall Goldsmith: “What got you here got you halfway there.” (Goldsmith had a New York Times bestseller in 2007 with What Got You Here Won’t Get You There.)

The transition from being a high-performing executive in a “swim lane” to having the “aperture of having a full enterprise” requires substantial new learning and skill development, Thompson argued, because no matter how great an executive you are or how prepared you think you might be, the stakes are existentially high. The risk that a CEO might “lose his or her head within the next year or so” is “easily like 20% or at the big brands It feels like it’s twice that,” said Thompson, who recently penned an essay on the subject of CEO “decapitation” for Fortune.

Adding to this pressure, Thompson and Loflin added, is the radical shift in board member expectations. Board members, who once might have been “golf buddies,” are now “really under the gun to perform.” They are “less patient” and expected to “actually deliver,” based on their subject matter expertise.

This environment demands nearly every candidate be ready to serve as a “peacetime in a wartime CEO,” Thompson said, capable of harvesting the best aspects of the company culture while also being “disrupting and breaking new ground.” An executive promoted from a functional role, such as a CFO, may possess the “gravitas of understanding the street and the shareholders,” but often lacks the breadth to “light hearts and minds” across the workforce, or do “ride-alongs with customers.”

The loneliness of the tower, and ‘relationology’

Fortune has been tracking this tenuous moment for leaders throughout 2025. Top recruitment firm Challenger, Gray & Christmas found 1,235 CEOs had left (or lost) their jobs through the first half of 2025, a stunning 12% increase from 2024 and the highest year-to-date total since Challenger began tracking CEO turnover in 2002.

Jim Rossman, Barclays’ global head of shareholder advisory, who’s been closely tracking shareholder activism for decades, similarly found record activist-linked turnover at the top for 2025. “It feels like what activists have done is basically [to hold] public companies to the standards of private equity,” Rossman told Fortune in a previous interview, as they have come to view the CEO “more as an operator, not somebody who’s risen through the ranks.” In other words: Results matter.

The intense environment contributes to feelings of isolation. As CEOs often note, being the boss is a lonely job where leaders are caught in the middle, with information they cannot share with reports but must share with the board, creating a huge information asymmetry, as Microsoft CEO Satya Nadella previously told McKinsey.

Carolyn Dewar, the co-leader and founder of McKinsey’s CEO Practice, previously told Fortune that “No one else in your organization or above you, like your board or your investors, see all the pieces you see.” She advocated for leaders to surround themselves with trusted advisors—“a kitchen cabinet” of sorts.

Similarly, Loflin told Fortune he’s fond of the concept of “relationology,” which he describes as “sort of a study of relationships.” He suggested leaders must develop a “portfolio of relationships of intimacy” that are “very context-relevant.” A leader’s effectiveness hinges on having fluency, for instance, when speaking to a CFO about analyst days, or working with a compliance team to keep the business safe or connecting authentically with union executives. Loflin said he’s often seen it being a “big surprise” to accomplished leaders that they have, say, seven different groups they need to engage and maybe as many as six new skills to really flesh out before they’re ready to take the enterprise to the next level.

This need for deep, context-aware connection also applies to personal life, Loflin added. The idea that a personal life and professional life can be entirely separate “undermines leadership and undermines the fabric of a company.” Critically, Loflin said, the chair must really know his CEO “at a deep level, like a Shakespearean level,” requiring a transparency that ensures appropriate accountability. After all, Loflin noted as one example, boards have to be mindful that a personal relationship that violates company policy can jeopardize corporate governance at the drop of a hat. The board really needs to know who their CEO is, maybe better than the CEO knows themselves.

The power and the privilege, the hubris and the humility

Loflin, who admitted to Fortune that he’s a bit of a Shakespeare nerd, noted the difference between a tragedy and a comedy is determined by “the vulnerability and the self-awareness of the protagonist,” and a tragic outcome results from a feeling he likened to “never recognizing whether I needed to grow or change.”

Thompson added that surviving as a CEO requires an “odd combination” of traits you might read in a Greek tragedy: hubris and humility.

The CEO must possess the hubris, or excessive pride, to believe they can be the best in their field, but also the profound humility that acknowledges they can’t do it alone.

The professional mandate is relentless, Thompson added, citing a key interview for the book from Qualcomm CEO Cristiano Amon: if you were the “same guy you were a year ago, you don’t deserve to be promoted.” Thompson said he thinks of hubris of being at “the edge of your competence, so rather than retreating, you actually should lean into that” to acquire the skills and help you need to keep growing as a professional.

For top leaders, Thompson said, the top job is not a prize to be won, but a “privilege to do this role.” Just as Olympic athletes must constantly improve, he added, leaders must recognize that breaking a record only attracts more competition.

Loflin urged boards and executives alike to move beyond a Wolf of Wall Street mindset and into “what it means to authentically care for and build the confidence and foster appropriate accountability.” He said that for many executives, admitting you have areas to improve on and get better at is a “special vulnerability.” He argued boards need more genuine, interpersonal affection—sometimes of the tough love variety—is needed to prevent a truly Shakespearean tragedy on their watch.

Loflin said he’d just had breakfast with a board director for a $30 billion company and the subject of love arose: “Do you love your management team?” The director said yes, definitely, almost like relatives. After all, they had been with the company over a decade and come to have deep relationships with other directors and their C-suite. Loflin argued that over decades of advising boards on corporate governance, he wishes more would adopt this sort of attitude.

“I don’t think it’s going to hurt anything in business because a good father has to talk to a troubled son, hopefully he’s mentoring when [the son is] getting himself in trouble.” After all, Loflin continued, “bad stuff happens, and I think some of these metaphors are important.” In other words, it shouldn’t be the Wolf of Wall Street, but the wolf—or the activist—is always at the door.

It’s a fair question. Crypto has become a strange reflection of our economy and society more broadly: part financial spectacle, part social experiment, part collective delusion. For every breakthrough in cryptography or blockchain infrastructure, there are ten new ways to speculate. The mood across the ecosystem has shifted. It’s not outrage or denial anymore…it’s fatigue.

Over the past few years, crypto has rotated through one speculative narrative after another: Layer 1 blockchains that quickly traded to huge valuations; NFTs that promised culture and delivered cash grabs; Metaverse real estate in the clouds; “Play-to-earn” games that collapsed before they even shipped. The most recent cycle brought us a flood of memecoins, which grew the universe of tokens from 20,000 in 2022 to over 27 million today, and now represent as much as 60%+ of daily application revenue on Solana. Then there are perpetual futures platforms that offer 100X leverage to largely retail traders.

Each cycle creates a new form of entertainment and a new way for speculative capital to churn. To date, the current era’s three most successful crypto retail applications – Pump.fun, Hyperliquid and Polymarket – have all fed this speculative bubble. One reality has become perfectly clear. The casino always finds a new table.

And yet, buried under all the speculative noise, something real is taking shape.

The most obvious sign is stablecoins bursting into the mainstream with a host of real-world use cases. Already, stablecoin circulation has reached more than $280 billion, and led financial incumbents to scramble for a response. The stablecoin boom reflects how institutional investors and asset managers are becoming less focused on the speculative nature of crypto and toward what can actually be built now that the pipes actually work and the advantages of faster, cheaper, and more secure rails are becoming clear.

AI, meanwhile, is accelerating the cognitive part of the equation. Where blockchain builds verifiable systems of record, AI introduces adaptability, reasoning, and speed. These two technologies complement each other in powerful ways: verifiable and immutable data for intelligent models, intelligent models for decentralized networks. Together, they create the architecture for products that address real-world use cases that couldn’t exist before – autonomous systems that transact, coordinate, and learn in real time.

This convergence is where the next chapter begins. Founders with deep domain expertise are building in financial infrastructure, global payments, AI compute networks, media, telecom, and beyond – massive sectors where the combination of trustless systems and intelligent automation can unlock entirely new markets. These aren’t speculative casino plays; they are fundamental rewrites of how value and data move through the economy.

The question has never been about available capital or interest. It has been about why investors should feel enough conviction to allocate to an industry with a history of prioritizing the casino. The consensus has been that despite blockchain’s potential, too many projects are chasing the same users, while too many teams are designing for each other instead of the broader market. The result has been a landscape full of potential energy waiting for its moment of release – a release that institutional investors finally realize is coming soon.

So, is any of this real?

The truth is that most of it still isn’t, but it is becoming more real everyday. For the first time in our 10+ years in the digital asset space, institutional investors are now acknowledging that this technology has the potential to touch industries far beyond crypto in ways that can reshape finance, trade, media, data, and beyond. And much of this potential is not far off.

That’s why we believe 2026 will mark the most meaningful shift we’ve seen in this space. The casino might still churn, but the builders who survive it will drive lasting innovation.

We’re betting on them and we’re more bullish on the future of this technology than ever.

Pete Najarian is Managing Partner of Raptor Digital who operates in both the digital asset space and traditional finance. Joe Bruzzesi is a General Partner at Raptor Digital and serves on the boards of Titan Content and Nirvana Labs.Their views do not necessarily reflect those of Fortune.

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.