We had the good fortune of connecting with Ray Chao and we’ve shared our conversation below.
Hi Ray, how do you think about risk?
Risk is always going to be a part of life: personal and professional. I try not to think of myself as being either a “risk taker” or “risk averse,” but try to assess the pros and cons of every decision. As a result, I don’t think of taking risks, but rather maximizing potential. Every decision has pros and cons, and I try to weigh the costs versus the benefits before making a decision. Also, I find it important to consider all aspects, and not focus entirely on financial gain or loss. There is value in experience, even if the outcome is not what you expected.
Perhaps the biggest “risk” that I took in my life involved a career change. I was fairly successful in law (a respected prosecutor in Chicago, law professor and published author/expert in juvenile law) when I decided to pursue acting. To say that was a surprise to my peers, students, family and friends is an understatement. Often, I was told how “brave” I was, and people would say they were envious of me for following my “dream,” but honestly, I loved being a lawyer. But, the fact that I loved being a lawyer allowed me to take the “risk” of leaving a financially secure career for a less secure career in entertainment. Often people make career changes (or other changes in life) because they are are unhappy. In my case, I was extremely happy as a lawyer, but I wanted to see how happy I could be as an actor and producer.
Interestingly, no one ever told me that I was crazy. Sometimes I even think I was crazy. But in hindsight (10+years after I quit practicing law), there really was not that much risk. If I was not happy or successful in my new career, I could always return to law. The only risk would have been not taking a chance.
Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
Perhaps the work that I am most proud of in entertainment is creating two film festivals. After attending a few dozen film festivals around the country as an actor, director or producer; I soon found a vibrant sub-culture that revolved around film festivals. More specifically, I was really impressed by the passion, creativity and commitment of indie filmmakers. These filmmakers often work full-time in order to fund their projects.
I decided to take elements of different film festivals and create my own. The first, the Twin Falls Sandwiches Film Festival, will have it’s 7th festival in 2022 in Twin Falls, ID; and the second, the Die Laughing Film festival will be the 6th annual festival this May in Hollywood. Both festivals really celebrate independent filmmaking and screenwriting, and bring like-minded creatives together to celebrate films and filmmaking. I’m really proud of these festivals and the network of talent that has helped create a dynamic, friendly, collaborative spirit.
Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I am a creature of habit which means I only go to a few favorite restaurants (and always order the same thing). When I entertain visitors, I always bring them to El Coyote, Aroma Coffee & Tea (Studio City), Porto’s and Daikokuya (Little Tokyo). In many ways, my favorite restaurants really highlight the diversity that makes Los Angeles so vibrant.
My favorite shop to bring visitors is the Last Bookstore in DTLA. It’s such an amazing, creative space, and unlike any bookstore.
One of my all-time favorite things to do is to drive on Sunset Blvd. I remember when I would visit LA, I would spend hours just driving on Sunset and absorbing the sights, sounds and people of LA. It’s always a fun ride, and never the same ride twice.
Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I know exactly who “changed” my life and led me to the path from law to acting. Her name is Linnie Wheeless. Linnie was a law student at the law school that I taught. Although she was not a student of mine, I taught many of her friends, so we knew each other. At the time, Linnie was taking improv classes at Second City and invited me to attend her student show. Even though I was born and raised in Chicago, I had never gone to any shows at Second City until Linnie’s show. In fact, I did not even know what improvisation was. The show was amazing, and after the show, I decided I wanted to take classes at Second City. And that is how I started my acting career.
Photos by Riley Rydin. Photo #3 and #8 Kevin Bradshaw.