The crisp morning air of San Francisco Bay carried more than just the usual maritime energy on this particular day. Fresh off the adrenaline-pumping SailGP event that had just wrapped up, two of Hawaii’s most celebrated watermen found themselves in unfamiliar Northern California waters, about to embark on an adventure that would forge an unlikely but powerful friendship.
Kai Lenny, the multi-disciplinary water sports phenomenon, and Jamie O’Brien, the fearless big wave surfer and YouTube sensation, had traveled to San Francisco for Red Bull’s SailGP festivities. The high-speed sailing spectacle had been everything they’d expected—cutting-edge technology, intense competition, and the kind of maritime innovation that spoke to their souls as professional watermen. But what they hadn’t expected was meeting Captain Joshua Waldman, a Bay Area sailing legend whose passion for foiling would introduce them to an entirely new perspective on their home element.
The Unexpected Introduction
Captain Waldman had attended the SailGP event not just as a spectator, but as a student. With decades of sailing experience under his belt and a growing fascination with hydrofoil technology, he was eager to see how the world’s fastest sailors were pushing the boundaries of what was possible on the water. The F50 catamarans, flying above the choppy waters of San Francisco Bay at speeds exceeding 50 knots, represented the cutting edge of sailing technology.
It was during the post-event festivities that fate intervened. Waldman, recognizing Lenny and O’Brien from their legendary water sports careers, approached the Hawaiian duo with the enthusiasm of a fellow waterman rather than a starstruck fan. The conversation that ensued revealed a shared obsession with the intersection of technology and water sports that transcended their different disciplines.
“When I heard they were in town and passionate about foiling,” Waldman later recalled, “I knew I had to get them out on the Bay. San Francisco has this unique energy for testing equipment and pushing limits—the wind, the waves, the current all conspire to separate the pretenders from the real deal.”
An Invitation Extended
What started as casual conversation quickly evolved into something more significant. Waldman, known throughout the Bay Area sailing community for his innovative approach to foiling and his willingness to share knowledge with fellow enthusiasts, extended an invitation that would prove transformative for all three men.
“You want to see what foiling is really about?” Waldman asked, his eyes gleaming with the kind of enthusiasm that only comes from someone truly passionate about their craft. “Come out on my boat tomorrow. I’ll show you how we do it up here.”
For Lenny, whose reputation as a master of multiple water sports disciplines was built on his willingness to embrace new challenges, the invitation was irresistible. Here was an opportunity to experience foiling from an entirely different perspective—not as a SUP foiler or windsurfer, but as part of a sailing crew pushing the boundaries of speed and efficiency.
O’Brien, whose career had been defined by his fearless approach to massive waves and innovative surfing techniques, was equally intrigued. The prospect of experiencing the water from a new angle, literally flying above the surface at high speed, appealed to his constant quest for new thrills and perspectives.
Setting Sail: The Bay Experience
The next morning dawned with the kind of conditions that make San Francisco Bay legendary among sailors—consistent wind, challenging chop, and the kind of dynamic environment that tests both equipment and skill. Waldman’s boat, a state-of-the-art foiling vessel that represented years of refinement and optimization, sat ready at the marina like a thoroughbred waiting for the race.
As they prepared to depart, Waldman took time to explain the intricacies of his setup. Unlike the Hawaiian waters that Lenny and O’Brien knew intimately, the Bay presented unique challenges—strong currents, rapid weather changes, and water conditions that could shift dramatically in minutes. The foiling system had been optimized for these specific conditions, with careful attention to stability, control, and safety.
“This isn’t just about going fast,” Waldman explained as they rigged the boat. “It’s about understanding how the foil interacts with water in constantly changing conditions. Every gust, every wave, every current shift affects how we fly.”
The Magic of Flight
As they cleared the marina and entered the main channel, the transformation was immediate. The boat that had felt solid and conventional at the dock suddenly became something altogether different as the foils engaged and lifted the hull clear of the water. The sensation was unlike anything Lenny and O’Brien had experienced, even with their extensive foiling backgrounds.
“It’s like surfing, but the wave never ends,” O’Brien observed, his usual high-energy demeanor subdued by the almost meditative quality of efficient foil flight. The absence of hull slap and spray, the smooth acceleration, and the sense of flying above rather than through the water created an experience that transcended their previous understanding of water sports.
For Lenny, whose mastery of various foiling disciplines had made him one of the sport’s most recognizable faces, the sailing foil experience provided new insights into efficiency and control. “The way the boat responds to trim adjustments, how you can maintain flight through lulls—it’s like a masterclass in foil dynamics,” he noted, his analytical mind already processing lessons that could be applied to his other disciplines.
Technical Deep Dive
As they sailed across the Bay, Waldman shared the technical insights he’d gained through years of development and testing. The foiling system wasn’t just about the underwater components—it was an integrated approach that included sail design, crew positioning, and real-time adjustment techniques that maximized efficiency and control.
The conversation naturally turned to the parallels between sailing foils and the equipment Lenny and O’Brien used in their respective sports. The fundamental principles of lift generation, angle of attack optimization, and stability management applied across all foiling disciplines, but the specific implementations varied dramatically based on the sport’s requirements.
“What you guys do with SUP foils and surf foils,” Waldman explained, “requires instant response and individual control. What we’re doing here is about team coordination and systematic optimization. Different applications, same physics.”
Shared Discoveries
As the morning progressed, the three watermen found themselves engaged in the kind of technical discussion that only comes from deep mutual respect and shared passion. Each brought unique perspectives to the conversation—Lenny’s multi-sport approach, O’Brien’s fearless innovation, and Waldman’s systematic sailing methodology.
They experimented with different sail trim settings, foil angles, and crew positioning techniques, with Lenny and O’Brien taking turns at various crew positions to understand how sailing foils responded to different inputs. The collaborative approach revealed insights that none of them had considered before.
“Jamie’s background in reading wave energy brought a completely different perspective to how we approached swells,” Waldman recalls. “And Kai’s understanding of foil behavior in different conditions helped us optimize our setup in ways I hadn’t considered.”
The Friendship Factor
What had started as a technical demonstration gradually evolved into something deeper—a genuine friendship based on shared values and mutual respect. Despite their different backgrounds and sporting disciplines, the three men discovered a common language rooted in their relationship with water and their commitment to pushing boundaries.
O’Brien, known for his infectious enthusiasm and social media savvy, began documenting the experience with his characteristic energy, but the content that emerged was notably different from his usual high-adrenaline productions. The sailing foil experience had a contemplative quality that brought out a different side of his personality.
“There’s something about efficient foil flight that makes you think differently about the water,” he observed during a break between runs. “It’s not about conquering or dominating—it’s about harmony and optimization.”
Lessons Learned
As they concluded their session and headed back to the marina, all three men recognized that they’d experienced something special. The technical knowledge exchange had been valuable, but the personal connections and new perspectives were equally important.
For Waldman, hosting Lenny and O’Brien had provided fresh insights into foiling applications he’d never considered. “Their approach to individual foiling sports gave me ideas about sail trimming and boat handling that I never would have discovered on my own,” he explains.
Lenny found that the sailing foil experience enhanced his understanding of efficiency and team dynamics that he could apply to his other sports. “The way they work together to optimize the boat’s performance—that teamwork approach has applications in everything I do.”
O’Brien, characteristically direct in his assessment, summarized the experience simply: “That was mind-blowing. The speed, the efficiency, the way you work as a team—it’s opened up a whole new world for me.”
Beyond the Bay
The friendship forged on San Francisco Bay that day extended far beyond a single sailing session. The three men stayed in contact, sharing insights, techniques, and opportunities as their respective careers continued to evolve.
Waldman found himself invited to Hawaii, where Lenny and O’Brien introduced him to their home waters and different foiling applications. The knowledge exchange went both ways, with the Hawaiian watermen gaining insights into systematic approach and technical optimization that enhanced their own disciplines.
The collaboration also influenced their respective projects and content creation. O’Brien’s subsequent videos showed increased technical depth and analysis, while Lenny’s multi-sport approach began incorporating elements of the systematic methodology he’d learned from Waldman.
Industry Impact
While the friendship between three passionate watermen might seem like a personal story, its impact extended throughout the water sports industry. The cross-pollination of ideas between sailing, surfing, and multi-sport foiling helped accelerate development across all disciplines.
Equipment manufacturers took notice of the collaboration, recognizing that insights from one sport could drive innovation in others. The technical discussions and shared testing between the three athletes provided valuable feedback that influenced product development cycles and design priorities.
The Bigger Picture
The San Francisco Bay meeting represents something larger than a chance encounter between three water sports athletes. It exemplifies the interconnected nature of modern water sports and the value of cross-disciplinary collaboration.
In an era where sports are increasingly specialized, the friendship between Waldman, Lenny, and O’Brien demonstrates the benefits of maintaining broad perspectives and open minds. Each athlete brought unique strengths to the collaboration, but all benefited from exposure to different approaches and techniques.
“The best innovations often come from outside your immediate discipline,” Waldman reflects. “Having Kai and Jamie bring their perspectives to sailing foils made me a better sailor and a better innovator.”
Continuing Evolution
The relationship established that day in San Francisco continues to evolve and influence all three men’s careers. Regular communication keeps them connected across their different sports and locations, creating an ongoing exchange of ideas and opportunities.
Recent collaborations have included joint equipment testing sessions, cross-training experiences, and shared content creation that showcases the interconnected nature of water sports. The friendship has become a model for how athletes from different disciplines can support and learn from each other.
Legacy of Connection
Looking back on that day in San Francisco Bay, all three men recognize it as a turning point—not just in their personal relationships, but in their understanding of water sports as interconnected disciplines rather than separate pursuits.
The technical knowledge gained was valuable, but the deeper lesson was about the importance of remaining open to new experiences and perspectives. Each athlete was already successful in his respective field, but the willingness to step outside their comfort zones and learn from each other led to growth that transcended individual sports.
For young water sports athletes watching from afar, the friendship between Waldman, Lenny, and O’Brien provides a powerful example of how collaboration and mutual respect can enhance performance and expand horizons. It demonstrates that true mastery comes not from isolation and specialization, but from continuous learning and adaptation.
Conclusion: The Power of Connection
The story of Captain Joshua Waldman, Kai Lenny, and Jamie O’Brien’s meeting in San Francisco is ultimately about the power of human connection in the pursuit of shared passions. What began as a chance encounter at a sailing event evolved into a lasting friendship that has enriched all three men’s careers and contributed to the broader evolution of water sports.
Their collaboration reminds us that the barriers between different sports and disciplines are often artificial constructs. The fundamental relationship between humans and water transcends specific activities, and the most significant innovations often come from the intersection of different approaches and perspectives.
As water sports continue to evolve and new technologies emerge, the example set by these three watermen provides a template for future collaboration and innovation. Their friendship proves that when passionate individuals come together with open minds and shared respect, the results can exceed anything they might achieve individually.
The San Francisco Bay served as the perfect backdrop for this meeting of minds—challenging conditions, innovative technology, and the kind of dynamic environment that brings out the best in serious watermen. But the lasting impact extends far beyond that single day, continuing to influence how these athletes approach their sports and how they share their knowledge with the broader water sports community.
In the end, the greatest victories aren’t always measured in competitions won or records broken, but in the connections made and the knowledge shared. The friendship forged on San Francisco Bay that day represents the best of what water sports can offer—not just individual achievement, but collective growth and mutual inspiration that elevates everyone involved.
