Rob Woodburn: Five Life and Leadership Lessons I Learned In The Military

Leadership also requires paying attention to the personal side of things. It’s not just about the professional — getting to know my actors as people, understanding their goals and aspirations, and building relationships that go beyond business matters helps create trust. A leader who shows genuine interest in their team’s well-being creates loyalty and long-term success. In the entertainment industry, where the highs and lows can be extreme, feeling supported and understood is critical for maintaining morale.

As a part of our series about “Life and Leadership Lessons Learned In The Military”, we had the pleasure of interviewing Rob Woodburn.

Rob Woodburn is a U.S. Navy veteran and former baseball player who has built a dynamic career in the international entertainment industry. Drawing on his military service and leadership experience, he now works as an agent and manager, helping actors achieve their full potential while fostering strong relationships across the industry. When he’s not working, Rob stays active through paddleboarding, weightlifting, and enjoying the coastal lifestyle in Manly Beach, Australia.

Thank you so much for doing this with us! Can you tell us a bit about your childhood “backstory”?

Thank you for having me!

I was born in Queens, New York, to Robert and Kathleen Woodburn. When I was about a year old, my family moved to the San Francisco Bay Area, where I was raised. I’m the oldest of four siblings — Michael, Shelly, and Julie — who all still live in Northern California.

Despite being a blue-collar, middle-class family, our parents made incredible sacrifices to send all of us to private Catholic schools from kindergarten through high school. Thanks to their hard work and dedication, all four of us went on to earn college degrees.

Growing up, I was passionate about baseball, the military, and movies and television. Baseball played a significant role in my life — I was fortunate enough to play in college, for the Navy, and even had a stint with a few independent league teams before finally hanging up my spikes.

And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?

I’m a talent agent and manager representing actors for screen and stage at the Rob Woodburn Agency (RWA) in Sydney, Australia. My journey in the entertainment industry began 25 years ago in the mailroom of the legendary William Morris Agency (WMA) in Los Angeles. Over the years, I worked my way up, and today, I’m proud to lead my own talent management agency.

At RWA, we take a hybrid approach that combines the expertise of both talent management and agency services to provide holistic, results-driven representation. My mission is simple yet ambitious: to guide my clients’ careers on an upward trajectory, offering unwavering support and strategic guidance while creating meaningful growth opportunities.

I currently represent around 50 actors and am highly selective about who I sign to the agency. I look for a combination of talent, a distinctive look, commercial viability, and, above all, professionalism. Once signed, I have each artist complete a detailed questionnaire covering topics such as their reasons for becoming an actor, strengths and weaknesses, favorite films and television shows, admired actors, and their short- and long-term goals. This helps me understand where they are in their career and where we want to go together.

My role goes beyond the typical duties of a talent agent — I act as a mentor and guide, providing a solid foundation for my artists’ representation. I conduct annual performance evaluations and offer resources to help them grow while generating a high volume of opportunities on their behalf. To keep everyone aligned, I produce a confidential RWA Monthly Recap, which includes key metrics like the number of auditions, callbacks, and bookings, along with comparisons to previous months and years. For example, between July and December 2024, RWA generated 1,500 opportunities — up 14% from the same period the previous year. This tells me we’re on the right track and continuing to build momentum.

At RWA, I consider the actors I represent part of my team, and my job is to lead them toward success. We operate under The Code, a set of high standards around professionalism, loyalty, and reliability. If an artist cannot meet those standards, it’s clear that RWA isn’t the right fit for them.

This comprehensive and disciplined approach ensures that my clients not only receive unparalleled representation but also have the tools and opportunities they need to thrive in a competitive industry. It’s a privilege to play a role in helping talented individuals achieve their dreams and build sustainable, fulfilling careers.

Can you tell us a bit about your military background?

I was attending college at Cal Poly, San Luis Obispo, where I played baseball and was a member of the Sigma Alpha Epsilon fraternity. During summers, I worked as a lifeguard. On the surface, it might sound like an ideal existence, but something always felt missing. I had a deep passion for the military and a strong desire to serve my country. Eventually, I reached a turning point where I thought, It’s now or never. So, I made the difficult decision to leave college and enlist in the United States Navy.

In February 1994, I began boot camp at Great Lakes, Illinois, which lasted eight weeks, followed by three weeks of Seaman General Skills Training. After completing training, I was assigned to the USS Enterprise (CVN-65), a nuclear-powered aircraft carrier undergoing a major overhaul at the Newport News Shipyard in Virginia, where the ship’s nuclear reactors were being refueled. The ship had a crew of over 5,000 sailors with the air wing when at sea.

When I first reported to the ship, I could have been assigned to any number of duties, and I braced myself for the toughest. However, the Personnel Department reviewed my record and noticed that I had several years of college experience and a background in baseball. They informed me that the ship had a baseball team — and I was now on it. Around the same time, I was invited to interview for the position of Captain’s (Commanding Officer) Orderly, as the current Orderly was being replaced following a promotion. This was a very high-profile role for a young sailor.

The interview process involved a thorough evaluation by the Captain’s senior staff, who grilled me with questions and assessed me closely. After passing their scrutiny, I was introduced to the Captain. He liked me and offered me the position. I served as the Captain’s Orderly for nearly two years, during which I trained two U.S. Marines to take over the role before I moved on.

As the Captain’s Orderly, I had the privilege of standing watch for him both in port and at sea. I observed countless hours of flight operations from the bridge, drove the Captain and visiting VIPs to meetings and ceremonies, and served as the first point of contact between the Captain and the ship’s department heads. The position offered me a front-row seat to some truly extraordinary experiences.

During my active-duty service, I consistently earned perfect scores on my performance evaluations, played for the ship’s baseball team, and was granted Secret Clearance. After completing my active duty service, I transitioned to the Inactive Reserves until November 2001, when I was honorably discharged.

Can you share the most interesting story that you experienced during your military career? What “takeaway” did you learn from that story?

There were countless stories during my military career, as every day with the Captain was a lesson in leadership. He was tasked with getting the USS Enterprise out of the shipyard and sea-ready — a mission that was behind schedule and over budget when he took command. Through his leadership, the ship was delivered ahead of schedule and under budget. He held the crew to a high standard, emphasizing accountability and eliminating finger-pointing. I saw him reduce grown men to tears when they fell short, but his fairness and clarity always earned their respect.

One of the most memorable experiences happened during workups, a critical training period, when we encountered a massive storm. Despite its size, the aircraft carrier was tossed around like a toy, and the sheer power of the sea was humbling. As we faced a towering wave, the Captain turned to me and said, “Hold on, Woody!” I braced myself and was nearly knocked off my feet by the impact.

After the storm passed, the Captain asked me to check on his at-sea cabin. When I opened the door, it was in complete disarray — papers, furniture, and personal belongings scattered everywhere. With the help of one of the Captain’s cooks, we worked together to get everything squared away. Once we were clear of the storm, the Captain slowed the ship and insisted on inspecting the damage personally. He turned to me and said, “Let’s go, Woody.”

We were harnessed for safety as we walked the flight deck, assessing the destruction firsthand. The winds were still strong, and seas rough, but the Captain wanted to see the impact with his own eyes. Just days earlier, we had conducted a weapons demonstration for NATO Defense Ministers, showcasing the ship’s readiness. And not long after the storm, we rescued a skipper and crew stranded far offshore, bringing them aboard for treatment — and even dinner with the Captain — before flying them to safety.

These experiences taught me two invaluable lessons: know your mission and lead by example. The Captain demonstrated both, time and time again. Leadership isn’t just about giving orders — it’s about facing challenges alongside your team, even when it’s uncomfortable or dangerous. His actions earned the unwavering respect of the crew and left a lasting impression on me. It’s a principle I’ve carried with me in every role since.

We are interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.

I witnessed acts of heroism every day during my time in the Navy. In my opinion, anyone who volunteers to serve their country and does so honorably is a hero. These individuals show up every day — not for money or recognition, but out of a deep love for their country. That kind of selflessness is truly admirable.

If I were to name specific heroes from the USS Enterprise, two people stand out: the Captain (Richard J. Naughton) and Petty Officer Matt Thompson, who served as the Commanding Officer’s Orderly before me. Matt was incredibly squared away, and stepping into his shoes was no small task. He set a high standard, and I’m proud to say we’re still friends to this day.

Outside my Navy experience, my grandfathers were two of my earliest heroes and the ones who inspired my respect for the military. Both were WWII veterans. Captain Bill Cusack, lead navigator of the 834th Squadron (Zodiacs), 486th Bomb Group, Eighth Air Force, flew over 30 missions in the European Theater of Operations. Sergeant Bill Woodburn served in the Marines in the South Pacific, enduring hardships that shaped his life. Both men returned home to start families, and their sacrifices continue to inspire me.

Based on that story, how would you define what a “hero” is? Can you explain?

To me, a hero isn’t a single person or a mold anyone can simply fit into. A hero is a symbol — an ideal to strive for. Being a hero calls for deep introspection, honesty, and righteousness. It’s about embodying the qualities of a role model who inspires others through their actions and character.

There’s a creed that I feel perfectly captures the essence of a hero. If you replace the word “gentleman” with “hero,” it resonates even more deeply:

“The True Gentleman is the man whose conduct proceeds from goodwill and an acute sense of propriety, and whose self-control is equal to all emergencies; who does not make the poor man conscious of his poverty, the obscure man of his obscurity, or any man of his inferiority or deformity; who is himself humbled if necessity compels him to humble another; who does not flatter wealth, cringe before power, or boast of his own possessions or achievements; who speaks with frankness but always with sincerity and sympathy; whose deed follows his word; who thinks of the rights and feelings of others, rather than his own; and who appears well in any company, a man with whom honor is sacred and virtue safe.” — John Walter Wayland

This creed encapsulates what it means to be a hero. It’s about leading with integrity, humility, and selflessness — qualities that inspire and elevate those around you.

Does a person need to be facing a life and death situation to do something heroic or to be called a hero?

No, I don’t believe so. A hero is someone who shows up every day, sees the big picture, and puts others before themselves. Heroism doesn’t have to come from a single moment of bravery — it can be found in the everyday actions of people who consistently demonstrate pride, courage, and commitment. I saw these qualities time and again during my military career.

In my personal life, my parents are my heroes. They sacrificed everything to raise four children and send us to some of the best Catholic schools in the Bay Area. On top of that, they helped each of us through college. How they managed it all on an automotive mechanic’s salary is still beyond me.

Their heroism wasn’t about grand gestures — it was about showing up every single day with unwavering dedication to give their children the best opportunities possible. Their example taught me that heroism is rooted in selfless acts and a deep commitment to others. It’s a lesson that’s shaped how I strive to live my life.

Based on your military experience, can you share with our readers 5 Leadership or Life Lessons that you learned from your experience”?

Based on my time in the military, I learned some incredible leadership and life lessons that have stuck with me through every chapter of my life. Here are five that stand out:

1. Know Your Mission and Communicate It Clearly. One thing I admired about my Captain on the USS Enterprise was his ability to articulate our mission. The ship was behind schedule and over budget when he took command, but he turned it around by setting clear priorities and holding everyone accountable. Watching him lead reinforced that people perform best when they know exactly what’s expected of them. Whether it’s delivering a project or preparing for battle, clarity is key.
2. Lead by Example. The Captain didn’t just give orders from his chair; he was out there with the crew, even in dangerous situations. I remember when we were caught in a brutal storm during workups. Once we made it through the worst of it, he insisted on walking the flight deck to inspect the damage himself. He told me, “Let’s go, Woody,” and we suited up and stepped out into the chaos. That moment earned him the respect of the entire crew because he showed he wasn’t afraid to get his hands dirty.
3. Accountability Builds Trust. One of the biggest lessons I learned was the importance of accountability. The Captain would hold people to a high standard, and if something went wrong, there was no finger-pointing — everyone owned their part. This taught me that leadership isn’t about avoiding blame; it’s about being responsible, even when it’s uncomfortable. People will respect you more if you admit mistakes and work to fix them.
4. Adaptability is Critical. In the Navy, plans can change in an instant, and you have to be ready to pivot. I learned this lesson early when I was unexpectedly assigned as the Captain’s Orderly. It wasn’t a role I expected, but I threw myself into it and made the most of the opportunity. This flexibility allowed me to be a valuable part of the team, and it has served me well in every unexpected challenge since — especially in my career in entertainment, where no two days are ever the same.
5. Small Acts of Leadership Matter. Leadership isn’t always about big speeches or grand gestures — it’s often found in the small things. Onboard the Enterprise, I learned the importance of showing respect to everyone, no matter their rank or role. Something as simple as taking the time to check in on someone or saying thank you can make a huge difference in morale. Those moments remind people they’re valued, which inspires loyalty and teamwork.

Do you think your experience in the military helped prepare you for business? Can you explain?

Absolutely, my military experience was instrumental in preparing me for the business world. The Navy taught me invaluable lessons in leadership, accountability, and perseverance that have carried over seamlessly into my career.

For example, serving as the Captain’s Orderly on the USS Enterprise gave me a front-row seat to leadership in action. The Captain was focused on delivering the ship ahead of schedule and under budget, and he made sure the entire crew understood the mission. Watching him lead through clear communication, accountability, and leading by example shaped my own approach to leadership in business.

The military also taught me to adapt to challenges and stay composed under pressure — qualities essential in any career. I recall a particularly challenging negotiation where things weren’t going as planned. I leaned on the adaptability and calm I developed in the Navy, staying focused on the goal and finding a solution under pressure. These skills have been crucial in my work in the entertainment industry, whether I’m managing talent or navigating complex deals.

In short, the Navy instilled in me a sense of pride, purpose, and work ethic that I rely on every day in business. The discipline I learned continues to guide my decisions, and I bring that same commitment to every project I undertake.

As you know, some people are scarred for life by their experience in the military. Did you struggle after your deployment was over? What have you done to adjust and thrive in civilian life that others may want to emulate?

I wasn’t scarred by my military experience, as I didn’t face combat directly during my time in the Navy. In fact, my experience had the opposite effect — it gave me confidence, accountability, pride, and a strong drive to succeed. The Navy taught me the value of discipline and leadership, and those lessons have shaped every part of my life since.

If anything, my time in the service made me realize how fortunate we are as civilians. Returning to college after my enlistment, I had a newfound appreciation for the opportunity to finish my degree. I attacked my studies with a determination I didn’t have before, and that drive has stuck with me ever since.

The Navy also helped me build resilience in the face of challenges, teaching me how to remain focused and calm under pressure. These lessons have guided me not only through my professional career but also in navigating personal and family challenges.

Joining the military was the best decision I ever made. It gave me the tools to grow as a person, a professional, and a leader. For anyone trying to find themselves or figure out their path, I’d wholeheartedly recommend considering military service. The Navy brought out the best in me, and I’m proud every day to be a veteran — because the man I am today is, in many ways, shaped by my service.

Are you working on any exciting new projects now? How do you think that will help people?

I currently represent a talented roster of actors across Australia and internationally, working diligently to secure exciting opportunities for them across all mediums of the entertainment industry. It’s a highly competitive market, and we average around 250 auditions per month, but what truly matters is the talent, drive, and marketability of the artists I work with. I’ve carefully assembled a team of performers who consistently prove they have the skill and dedication to succeed in top-tier productions.

With Australia emerging as a growing hub for entertainment, there are countless exciting projects on the horizon. One of my core beliefs is that there are no small roles, only small actors — and I’m proud that the talent I represent consistently steps up to every opportunity with passion and professionalism.

The work I do helps connect incredible performers with projects that do more than just entertain — they inspire and challenge audiences. Whether it’s through powerful storytelling or unique characters, I’m thrilled to help make those connections and play a role in bringing stories to life.

What advice would you give to other leaders to help their team to thrive?

To help your team thrive, whether in the entertainment industry or any other field, you need to create an environment where they feel valued, empowered, and motivated to perform at their best. As a leader, it’s not just about offering guidance but also challenging your team to push their limits and grow. In my case, my actors are my team. I strive to provide them with opportunities while giving them the freedom to bring their unique creativity to every role and project.

In the entertainment industry, creativity is at the heart of everything we do, and that requires an environment where open communication and collaboration are key. I always encourage my actors to share their ideas and perspectives, which helps them feel supported and inspires the best performances. It’s important to me that they understand that every opportunity, no matter how small, is a chance for them to grow, and I’m there to help them get to that next level.

A great team is built on trust, and that starts with leading by example. I show up with integrity, consistency, and accountability — qualities that I expect from my actors as well. I recognize their hard work, celebrate their successes, and provide constructive feedback when needed. In an industry as dynamic and unpredictable as show business, it’s essential that everyone knows they can count on you to lead with honesty and respect, especially when the pressure is on.

When actors know they are supported, challenged, and celebrated, they’re more likely to thrive — both as individuals and as part of a team. By creating an environment where their creativity is nurtured and their potential is pushed, you not only help them succeed in their craft but also build a lasting, collaborative relationship that benefits everyone in the long run.

What advice would you give to other leaders about the best way to manage a large team?

Managing a large team, especially in the entertainment industry, can certainly be challenging, but the key is to break it down into manageable parts and ensure that each individual feels seen and valued. As an agent representing my actors, who are my team, it’s crucial to stay organized, set clear expectations, and delegate effectively. You can’t do everything yourself, and in the entertainment world, there are often many moving parts — auditions, negotiations, meetings, etc. So, it’s important to trust your team to guide their specific areas, while you provide the overall vision and strategy.

Communication is absolutely critical when managing a larger team. In my role, I ensure that every one of my actors understands not only what’s expected of them but also how their individual contributions fit into the bigger picture. Whether it’s preparing for an audition or staying engaged with ongoing projects, clear communication keeps everyone on the same page. Regular check-ins, both individually with my actors and as a group with the entire team, are essential to maintaining alignment and motivation.

Leadership also requires paying attention to the personal side of things. It’s not just about the professional — getting to know my actors as people, understanding their goals and aspirations, and building relationships that go beyond business matters helps create trust. A leader who shows genuine interest in their team’s well-being creates loyalty and long-term success. In the entertainment industry, where the highs and lows can be extreme, feeling supported and understood is critical for maintaining morale.

A large team can absolutely thrive when they feel like a close-knit unit, even if they’re working on different projects or across various media. Keeping them connected, valued, and focused on a shared vision will help them not only succeed but also remain passionate about their craft.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story about that?

I’ve been incredibly fortunate to have had some exceptional mentors throughout my life — in the military, sports, and business. However, the mentors I’m most grateful for are, without a doubt, my parents.

Growing up, they made countless sacrifices to ensure that my siblings and I had opportunities to succeed. They gave up things like new cars, a bigger home, and vacations to invest in our education and futures. They sent us to the best schools they could, not just for academic opportunities, but to help us grow as individuals. Their teachings weren’t just about getting good grades — they instilled in us a sense of responsibility, a strong work ethic, and the importance of being good, decent people. They taught us to care for others, give back, and always do the right thing, even when it’s not the easy thing.

When I chose to drop out of college and join the Navy, most parents might have felt disappointed. But my dad was different. He told me he was never more proud of me than when I made that decision. Their unwavering support has been a constant source of strength. And when I transitioned from finance to entertainment, they were right there beside me, cheering me on. Their belief in me, even when the path wasn’t clear, has shaped who I am today.

My parents are not just role models; they are my heroes. The love and sacrifices they made for me and my siblings are immeasurable, and I carry their lessons with me every day. They’ve shaped me into who I am and continue to inspire me to be the best version of myself.

How have you used your success to bring goodness to the world?

I believe I have. Every day, I use my experience, skills, and relationships to create opportunities for my artists, helping them achieve their career aspirations and pursue their dreams. They know that I am fully invested in their success and willing to go the extra mile for them. In return, they give me their loyalty and professionalism, which fuels our shared drive for success.

On a broader level, when an actor performs — whether on screen or stage — they’re sharing a story with the audience. Storytelling is a timeless art form, deeply ingrained in humanity’s history. It’s a powerful way to connect, communicate, and inspire. By helping these artists tell their stories, I feel that I’m contributing to something greater — bringing meaningful narratives to the world that have the potential to impact, entertain, and transform lives.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

If I could inspire a movement, it would be about empowerment through purpose, discipline, and community — a movement that encourages individuals to show up every day with a clear sense of purpose, put in the work, and embrace the journey, even when things get tough.

Having come from a background in the military, business, sports ,and the entertainment industry, I’ve seen firsthand how powerful it can be to commit to something greater than yourself. In entertainment, just as in life, success is not always immediate. A movement like this would help people tap into their own potential by taking responsibility for their actions and relentlessly working toward their goals, whether on set, in auditions, or behind the scenes. It would foster a culture of accountability, creativity, and collaboration, where individuals support each other, hold themselves and others accountable, and take pride in their craft.

It would also focus on the idea that heroism isn’t defined by one single, dramatic moment, but by the everyday actions that add up over time. Whether in a career, in a family, or in a creative endeavor, it’s about showing up consistently, putting others before yourself, and making a difference through small, meaningful actions. In the entertainment world, this is about every team member, from the actors to the crew, understanding that their contributions, no matter how small, are part of something bigger.

I believe this kind of mindset has the potential to ripple out into communities, workplaces, and beyond. When we invest in ourselves and those around us — when we’re dedicated to doing the right thing day in and day out — it has the power to drive positive, long-lasting change. Imagine if each person in the entertainment industry, from the performers to agents and producers, dedicated themselves to working toward their goals, helping others along the way, and striving to build a better, more inclusive industry through consistent effort and mutual support. That’s a movement I’d love to see take shape.

Through my work in the entertainment industry and my military background, I’ve learned that success doesn’t come from one big moment — it’s built on the day-to-day efforts, relationships, and drive to keep pushing forward. This movement would celebrate that idea and inspire a culture of resilience, creativity, collaboration, and purpose.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Currently, my favorite “Life Lesson Quote” is: “Stay hard — don’t sop when you’re tired, stop when you’re done.” — David Goggins.

This quote resonates deeply with me, both personally and professionally. At 54, I’m mentally and physically stronger than I’ve ever been, and I’ve learned to push myself far beyond what I once thought were my limits.

In the entertainment industry, rejection and disappointment are inevitable. Success often feels like a distant dream, but this mindset has been crucial to my persistence. You can’t stop when you’re tired or discouraged; you stop only when the work is done and you’ve given it everything you’ve got. Every audition, every project, every opportunity is a step toward success, and learning to embrace the grind, even when the results aren’t immediate, has been a game-changer. Loving the work and appreciating the small victories makes the bigger successes even more rewarding.

Thank you so much for these amazing insights. This was truly uplifting.