There’s traditional fundraising, and then there’s the kind of fundraising GLIDE does that makes headlines each May.

Since the inception of the Power of One lunch series, Warren Buffett’s iconic charity auctions have raised more than $53 million to support GLIDE’s mission. Conceived by Susie Buffett, the annual lunch has become synonymous with Buffett’s pragmatic and no-frills approach to impact and philanthropy.

The initiative quickly drew attention and bidders, establishing a precedent for creative fundraising that bends the rules on how to engage with billionaires who aren’t always thought of as much more than the checkbooks they carry.

The approach Buffett pioneered has proven incredibly effective, raising millions over the years, with his final round alone bringing in $19 million.

Dr. Gina Fromer, GLIDE’s CEO, highlights the critical impact of these efforts: “This auction has transformed lives, no question. Every dollar raised directly translates into hope and opportunity for those who need it most. We’re eternally grateful to Warren for what he started as we are to Marc for having taken up the role.”

After Warren Buffett stepped back, Salesforce CEO Marc Benioff took the baton, another billionaire renowned for his philanthropic efforts. Benioff is best known for Salesforce’s innovative 1-1-1 philanthropy model, the company’s investments in education and healthcare, and his own outspoken advocacy for social justice. Which brings us to the less-known part of this equation; the winning bidders themselves.

Past winners have included notable figures such as hedge fund manager Ted Weschler, who secured a job at Berkshire Hathaway after his lunch with Buffett, and cryptocurrency pioneer Justin Sun, who famously paid $4.6 million for the privilege, setting a record at the time.

The winning bids are usually kept quiet, but this year we had the opportunity to connect with the latest winner, Yi Shi, a Chinese-German tech entrepreneur known for his work in AI and his advocacy for responsible technological progress. In an interview after his winning bid, he shared what he hopes to achieve through his bid and the opportunity to sit down with Benioff.

Going for seconds

If Yi Shi continues at this pace, GLIDE might need to rename the event “Power of Two.”

Shi previously attended a Power of One lunch with Warren Buffett as a guest in 2015, at just 25 years old, invited by the then-winner Zhu Ye, chairman of Da Lian Zeus Entertainment.

Reflecting on the experience, Shi described the meeting with Buffett as a remarkably down-to-earth event. “We never felt like we were eating with a billionaire,” Shi shared, noting how naturally Buffett took on the role of a mentor in the meeting. “He emphasized compassion and empathy, teaching us that wealth comes in many forms, financial, health and wellbeing as well as the ways you can contribute back to society.”

The sit-down with Buffett piqued Shi’s curiosity about blending philanthropy, innovation, and responsible governance. It also laid the groundwork for his bid to lunch with Marc Benioff ten years later, and after placing $200,100 on the table he rightfully has great expectations for the event.

Shi, a Chinese-German tech entrepreneur, has spent his career building and running companies that exist to scale technology. From founding Avazu Inc., a programmatic advertising pioneer, to co-founding oBike, a bike-sharing innovator, Shi now heads FlashIntel, a Silicon Valley startup creating AI agents for enterprise sales and support, a field closely aligned with Salesforce’s own trajectory.

“Meeting Marc is part of my ongoing journey as a founder,” Shi explained. “I’m eager to learn how he scaled Salesforce from startup to a $300 billion company, maintaining his passion and vision throughout.”

Benioff himself is well-known for blending corporate leadership with social impact, pioneering Salesforce’s acclaimed 1-1-1 philanthropy model. Shi shares this ethos, supporting liberal values, individual liberties, and innovative policies to responsibly advance technology, especially artificial general intelligence (AGI). His own philanthropy includes grants to his alma mater, the Goethe Institute, reflecting what he describes as a deep commitment to education, responsible innovation, and the promotion of free-market principles.

“I’m interested in how we build responsible governance around emerging technologies without stifling innovation by top-down control,” Shi noted, echoing Benioff’s emphasis on social responsibility and ethical innovation.

Shi’s winning bid is philanthropy in motion itself, and it directly supports GLIDE’s crucial work, addressing poverty, homelessness, and social injustice in San Francisco. Dr. Gina Fromer, GLIDE’s CEO, underscored the event’s importance: “This auction is a lifeline for thousands of vulnerable people we serve. Each bid directly translates into dignity, hope, and meaningful change.”

Looking back, the tradition started with Warren Buffett and Reverend Cecil Williams, whose collaboration defined GLIDE’s compassionate approach to community service. “We stand on the shoulders of giants,” Dr. Fromer reflected, “and we look forward with gratitude and optimism.”

Shi, for his part, sees philanthropy as both duty and privilege. “I hope my efforts encourage others to participate. We have the resources and technology to create unprecedented abundance, if we choose to act responsibly and generously. Joining Marc in his endeavor to support GLIDE is a worthy cause in and of itself, and sitting down with him is simply the cream on top.”

A deep discussion in the making

Yi Shi has specific ideas he looks forward to exploring with Marc Benioff and the guests he brings.

It might not surprise you that at the forefront of these topics is artificial intelligence. Salesforce itself has placed big bets in this arena, recently launching innovations such as Agentforce, further embedding AI into their core CRM offerings.

Shi believes AI-native companies, like his own FlashIntel, have the potential to disrupt traditional industry leaders, including the likes of Salesforce. While he is exactly as ambitious as a serial entrepreneur should be, he cautions others to temper their expectations on how far startups can push the AI-disruption.

“Trying to directly replace Salesforce with conventional CRM solutions is likely to fail,” Shi remarked. “The real disruption that we’ll see will come from someone creating a completely new category, something innovative that addresses customer needs from an entirely different angle, much like what Marc did with Salesforce back in the day.”

There’s no discussing disruptive innovation without leaning on the concept of creative destruction, a topic Shi has plenty of first-hand experience on. “To build something new you often have to dismantle what came before, and I have several convictions about how we’ll see AI do that,” Shi shared.

“One of the larger transformations I see is that the future’s currency will likely be tokens generated by AI models,” Shi explained, outlining his vision for how AI will build entirely new venues for transacting and value transfer.

“I also expect significant changes to how we scale companies themselves, shifting from operational expenses to capital investments in technology,” he continues.

We’re seeing much of this in action already, notably in how Salesforce continues to evolve through AI-driven innovations like Agentforce, enabling its clients to scale faster and more effectively than ever before.

Shi is particularly keen to dive deeply into conversation with Benioff on precisely these points. “Marc’s journey with Salesforce, marked by numerous pivots and significant growth milestones, is something I deeply admire,” Shi shared. “I’m eager to understand his vision for the future, how he’s navigated challenges, and what it truly means to build a legacy company through constant innovation.”

Yet, their upcoming conversation will undoubtedly venture beyond AI innovation, touching on themes central to Buffett’s legacy, long-term thinking, patient investment, and sustainable impact. Both Benioff and Buffett exemplify this commitment, demonstrating how steadfast strategic decisions compound over time into transformative results.

Shi also holds Buffett’s long-term investment philosophy in high regard, emphasizing the necessity of forward-looking discussions. “Conversations that focus on the long term are increasingly essential,” Shi said. “Both Buffett and Benioff remind us of the profound impact thoughtful, deliberate action can have, and I’m keen to play my part in the small ways I can.”

Dr. Fromer reinforces this sentiment by emphasizing the collective effort required for lasting change: “There’s no work we could do without the support of people like Marc Benioff, Warren Buffett, and every single bidder who has stepped up. It truly takes a community to make a community work, and the impact we strive for is measured not in months or years, but across generations.”

And in fueling that work, there’s power in lunches shared in extraordinary company.