Thomas Caska: Inside the Transition from Broadway Stages to Hospitality Leadership at Hilton

Many successful people reinvented themselves in a later period in their lives. Jeff Bezos worked on Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Kroc was a milkshake-device salesman before starting the McDonalds franchise in his 50s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Thomas Caska.

Thomas (Thom) Caska is the General Manager of Hilton New York Times Square, where he proudly brings over a decade of experience from both the hospitality and performing arts industries. After 10 years of working with top production companies across Broadway, film and television, Thom challenged himself to a new role by joining the Hilton family where he’s held various leadership roles from food and beverage to General Manager at some of Hilton’s top New York City properties. Today, his unique background in theater and hospitality gives him an effective approach to leadership, blending performance with guest experience to deliver exceptional service at one of New York’s most iconic hotels.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I was born in Brooklyn and grew up in and around NYC. My mom was from a close-knit Italian family in the Bronx. My dad, originally from Brooklyn, worked as a printer just down the block from what’s now Hilton New York Times Square on 38th Street. Later, we moved upstate and I attended high school in a small town about 30 miles south of Albany, known as the Apple Picking Capital of the World. It was a great blend of city life and rural living — a true “tale of two cities” experience.

Creativity was in my bones from an early age. I found every opportunity to dance, sing, play an instrument, write, and paint. It was something that fueled me throughout my childhood. I also had a deep love for the outdoors and Boy Scouts became a big part of my life, ultimately leading me to achieve my Eagle Scout as a teenager.

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

“Tomorrow is no place to place your better days.” It’s a lyric from a Dave Mathews song, but it has always motivated me. The idea to seize the day and not wait for tomorrow. As an artist it’s always served as my north star to remind me that we need to take advantage of every door that opens and take nothing for granted.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

First, a strong moral compass. My mom raised my sister and me with the belief that “doing the right thing is never the wrong thing,” a lesson that’s guided me throughout my career. It’s helped me remain someone who never cuts corners and approaches challenges with compassion.

Making lemonade from lemons. This is also an idea that my mom really instilled in us. We didn’t grow up with a lot of extras, but we never knew it. We always found ways to look at situations through what their potential was, not what the obstacle was. This outlook has been invaluable when building and motivating teams, I always look for creative angles to inspire people by focusing on opportunities instead of limitations.

And finally, laugh as much as you can. Time with my dad, a true prankster, was spent finding joy in the simple things. As an actor, this sense of humor helped me handle failed auditions and awkward moments with ease. Today, it helps me shape a positive work environment where people feel free to be their authentic selves and find joy in what they do.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I’ve been a musician and actor for as long as I can remember, participating in extracurriculars throughout my youth. After high school, I interned for a year at the former New York State Theatre Institute in Troy, where my passion turned into a career possibility. I trained in everything including music composition, stage combat, carpentry, business, acting, dialects, performance, dance, and history. I was also granted the opportunity to begin performing professionally and was cast in several different productions with world-renowned Tony, Emmy, and Academy Award-winning artists.

Following my internship, I moved back to Manhattan to pursue acting full-time, further hone my craft, and begin building relationships in the industry. I also enrolled at Pace University, where I now serve on the President’s advisory council, to pursue a degree in musical theatre and education. My career took off, leading me to roles in the national tour of Fiddler on The Roof and off-Broadway productions as well as TV, film, plus-sized modeling, summer stock theater, and even collaborating on a Broadway musical with the band STYX.

And how did you “reinvent yourself” in your Second Chapter?

After years of touring, acting, and moving from city to city, I began craving more stability, something that an actor’s life didn’t offer. During my acting career, I’d taken side jobs as a bartender, carpenter, and eventually began working part-time at Theatre Row Studios. When a full-time position opened, I stepped into a management role. I was still involved in the arts, but was more focused on the management side and eventually worked my way up to their Studio General Manager, where I oversaw their rehearsal spaces and food and beverage. I was still bartending on the side when an opportunity to work in the beverage department with the Madison Square Garden Company became available, leading me to head their F&B team at the Beacon Theatre.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

My boss at the Madison Square Garden Company, a fantastic mentor named Jamal Massengale, took a position at New York Hilton Midtown. He reached out to me and said, “You have incredible potential in hospitality, and there’s an opportunity here that could launch the rest of your career.” Encouraged by his support, I took the leap and joined New York Hilton Midtown as Director of Restaurants & Lounges. The rest is history.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing?

I discovered that I could still channel my creativity outside of the arts. I grew my skills as a mixologist and found immense fulfillment in creating cocktails, as well as designing menus for the restaurants and events I managed. This has allowed me to bring a creative touch to my role.

How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

I was fortunate to have incredible mentors and supportive parents who encouraged every step of my journey. A year after my career transition, I met my now-wife, Lauryl, who completely transformed my outlook on life. She gave me the confidence and love to conquer whatever I wanted, and she still does.

How are things going with this new initiative? We would love to hear some specific examples or stories.

It’s going very well! While my hotel career is still relatively young, I’ve been in hospitality for over 20 years, with the last 10 focused on hotels. In that time, I’ve advanced quickly and am now on my third General Manager assignment.

2020 presented an unexpected accelerator that took a lot of my training and development through an express train. During that time, I was working at Millennium Hilton New York One UN Plaza, one of the few hotels that remained open. We had to adapt rapidly, which kicked my training and growth into high gear.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Meeting my wife, Lauryl, completely changed my life. When I was acting and bartending, my focus was mostly on the present, and my impact felt limited. With Lauryl, my focus shifted from the “now” to the “future.” My favorite quote, “tomorrow is no place to place your better days,” took on new meaning. Before, it was about seizing the day, but with Lauryl, it became about making the most of today for a better tomorrow.

Can you share the most interesting story that happened to you since you started in this new direction?

Reopening Hilton New York Times Square felt like a full-circle moment, merging my past and present. This hotel is in the same neighborhood I used to walk through with my dad, a block away from the theaters I once performed in and only two blocks from Theatre Row Studios, where I spent many years. I started to partner my theatre contacts with my hotel contacts and, as a result, we launched some great themed suites and initiatives including an extended partnership with Disney Theatrical Group. Today’s guests can book Aladdin’s Times Square Palace Suite and THE LION KING’s Royal Suite.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

Absolutely, especially as an actor. Statistics show you will book one out of every 50 auditions. That comes with 49 rejections. That experience taught me to build a thick skin and persevere, no matter the odds.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I’ve kept my core support group of theater friends close throughout this journey. Artists are incredibly supportive as they understand firsthand the challenges of trying new things and the inevitable bumps and bruises that come with the process.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

For the longest time, I shied away from sharing my background as an artist with my hospitality colleagues — almost feeling embarrassed by it. Embracing and talking about it now is definitely pushing me outside of my comfort zone.

What are your “5 things I wish someone told me before I started” and why?

1 . If it isn’t hard, it isn’t worth it. I truly believe that it’s the challenging days that teach us the most. While I don’t like to dwell on what March 2020 meant for the hospitality industry, there’s no denying how much it shaped me as a leader. At that time, I was at Millennium Hilton New York One UN Plaza, one of the few hotels that remained opened. Finding ways to motivate the team through that time was a challenge, but it was an experience that forever influenced how I approach leadership.

2 . Don’t give up. Sometimes, when one door closes, you have to kick another one down. When I was acting, rejection was a constant part of my daily life. Staying committed to what you believe in and finding the will to push forward is what truly matters.

3 . What you do isn’t all of who you are. As an actor, you’re trained to react and perform in a specific way to portray a character, which sometimes means hiding your authentic self. One of the most valuable lessons I’ve learned at Hilton is that what makes you you is also what makes you great. By infusing my passions — whether about life or family — into my work, I’ve found not only more joy in what I do but also greater creativity, enabling me to think beyond the norms of the status quo.

4 . Lower the stakes — you’re only human. High performers in any industry often tend to be overly critical of themselves. Early in my hotel career, I would take my day-to-day very personally, and missteps or mistakes would sometimes throw me off track. Over time, I realized that while self-criticism has value in small doses, being too hard on myself only led to more mistakes. It’s important to take things in stride — like a boat floating down a river, you have to let the current carry you forward. Holding on to mistakes like an anchor only clouds your ability to move on to the next opportunity.

5 . Sleep when you’re tired. Hard work is often seen through the lens of “hours punched” or the old adage, “first to arrive, last to leave.” While dedication is important, there’s even greater value in recognizing when you’re not at your best. Our bodies tell us when they need to recharge, and it’s essential to listen. A task that might take two hours late at night could often be done in just 20 minutes after a good night’s sleep and a fresh cup of coffee. With only so many hours in a day, prioritizing rest ensures you can be present for yourself, your family, and ultimately, more effective at work too.

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?

Embrace the idea that what you do today may not be what you do tomorrow and that is the beauty of life. Changing paths isn’t a detour, it’s part of the journey. Learn, grow, and develop, but always stay fulfilled.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

Without a doubt, Dave Matthews. I believe each person has the power to make the world a little better today than yesterday, and a bit more peaceful tomorrow. I believe a lot of that comes from growing up with his music. His humanitarian efforts are unmatched, and the love and unity he writes with he also practices. He also is an absolute legend.

How can our readers further follow your work online?

Readers can stay up to date with Hilton New York Times Square by visiting our website and following us on Instagram @hiltonnytimessquare.

Thank you so much for sharing these important insights. We wish you continued success and good health!