Ryan Reynolds has captivated audiences for years with his quick-witted humor and memorable acting performances.

But in recent years, he has also emerged as an impressively savvy entrepreneur through his ownership of Aviation American Gin.

Reynolds purchased Aviation Gin in 2018 alongside his business partner, Neal Brothers Foods CEO Andrew Chris. Despite Aviation being a relatively small, lesser-known spirit at the time, Reynolds saw massive untapped potential. And his vision proved fruitful – just two years later, he sold Aviation to global beverage giant Diageo for an estimated $610 million.

Beyond the remarkable deal, Reynolds has since continued on in an active leadership role as owner and chairman for Aviation Gin. He has guided the brand to new heights through his creative marketing tactics and personable, lighthearted approach.

Reynolds’ journey with Aviation Gin provides many valuable lessons that leaders across all industries can look to for inspiration:

Use Humor Strategically

Humor has always been a central part of Reynolds’ personal brand and appeal. He effortlessly uses comedic banter and self-deprecation in interviews and social media to come across as authentic, magnetic, and instantly likable.

The same rings true for Aviation Gin’s branding and marketing where clever puns, funny product reviews, laugh-out-loud billboards, and amusing social media posts are par for the course. Reynolds and his team ingeniously incorporate comedy into their messaging to grab customer attention and get people engaged with and talking about the brand.

While not every company can pull off Reynolds’ signature humor and snark, there are merits in using humor strategically. The right dose of lightheartedness makes brands seem more human and can foster emotional connections with customers. It also helps messaging feel fresh and differentiated from overly corporate, dry communications. Leaders should identify opportunities to interject humor into their marketing, communications or workplace culture in an authentic way.

Pursue Innovation and Take Risks

When Reynolds initially invested in Aviation Gin, it was a huge risk. The brand had low awareness and a short track record relative to category titans like Tanqueray or Bombay Sapphire. But Reynolds was willing to trust his instincts and put in the work to realize Aviation’s full potential.

First, this involved rethinking Aviation’s positioning and branding. Reynolds tapped into his Hollywood network to create an elegant, sophisticated packaging redesign that better conveyed the spirit’s premium quality.

Next was overhauling the marketing strategy with an edgy, playful campaign that aligned with Reynolds’ sensibilities. Irreverent billboards and unusual digital shorts captured attention in crowded gin category. And Reynolds even leveraged his own fame by starring in Aviation’s first TV commercials.

The combined effect was transformative. Just three years after Reynolds’ initial investment, Aviation’s volume had grown over 400%. And Reynolds’ risk paid off further when Diageo purchased the brand for that industry-shocking $610 million price tag.

The Aviation success story demonstrates the importance of pursuing strategic innovation and not being afraid to take risks. Had Reynolds just maintained the status quo after investing, Aviation likely wouldn’t be where it is today. Business leaders should continually evaluate opportunities to refresh strategies, push boundaries and even constructively disrupt their own space.

Stay Grounded with Humility

Despite his soaring success as an entrepreneur and investor, Reynolds maintains endearing humility and doesn’t take himself too seriously. He celebrates achievements without letting ego or entitlement seep in. And he seems comfortable graciously acknowledging past failures in business and his personal life.

Reynolds brings this same lighthearted humility to the way he talks about Aviation Gin too. In interviews about the Diageo acquisition, he is quick to credit his business partners and team for their essential contributions. And on social media, he regularly pokes fun at himself as Aviation’s “owner, mouthpiece and, most of time, janitor.”

This genuine humility likely stems from Reynolds’ early career days filled with rejection and struggling to catch a break. While his fame and fortunes grew later on, he retains the grounded perspective that success doesn’t solely stem from one’s own doing.

For leaders aiming to build trust and connection within their organizations, taking a page from Reynolds’ humility playbook is essential. Leave ego and self-importance at the door. Share credit, especially publicly. And stay in touch with the mindset of when you were just starting out. These practices make leaders seem more relatable and human.

Empower Your Team

Behind Reynolds’ starring role as Aviation Gin’s mouthpiece, there has undoubtedly been a driven, creative team working tirelessly to transform the once-obscure brand into an industry trailblazer.

Details around Reynolds’ leadership style with his Aviation team are sparse. However, some clues indicate he advocates empowering employees with ownership and decision-making influence.

For example, Reynolds has spoken about Aviation employees having the freedom to chime in with wild branding ideas that he then tries to bring to life. And in discussing Aviation’s future upon the Diageo sale, he said the brand would benefit greatly from “the power of their distribution and infrastructure…We don’t have any of those things.”

This insinuates Reynolds sees collaboration and utilizing partners’ expertise—whether through strategic alliances or his own internal teams—as key for taking brands to the next level.

Effective leaders realize they do not have all the answers alone. Seeking diverse perspectives across different disciplines and experience levels helps fuel innovation. Granting team members agency in their roles also builds trust and boosts engagement. Leaders should continually assess opportunities to foster autonomy and ownership among their reports.

Learn from Both Successes and Mistakes

While Reynolds has seen enormous success recently in his entrepreneurial pursuits, his journey also includes pivotal failures.

In 2004, Reynolds co-founded a creative agency called Meld Media. Despite some initial momentum, the shop ultimately went under one year later. In interviews, Reynolds has spoken openly about this experience and the emotional toll of needing to lay off staff he had hired.

But despite the sting of this early business failure, Reynolds seemed to apply the lessons to his future ventures. When discussing his investment strategy, Reynolds said: “I fail all the time but I don’t make the same mistakes twice. I make new ones, but don’t repeat my old ones.”

This underscores why leaders must adopt a growth mindset around wins and losses. Both provide springboards for critical learning if the right culture of curiosity and introspection exists. After mistakes or failures, leaders should carve out time for earnest self-reflection on what went wrong and assumptions that need challenging. Share these review processes with teams too so collective knowledge grows. Setbacks often fuel the greatest progress, granting future wins are bigger or happen faster.

So in looking at the meteoric rise of Aviation Gin, Ryan Reynolds’ leadership style indeed offers many helpful lessons for leaders everywhere – have a sense of humor, empower your staff, embrace humility. While few may ever match his comedic wit, striving to apply these principles can undoubtedly help strengthen leadership abilities and drive success.