Meet Gregory Cali | Artist & Gallery Owner

We had the good fortune of connecting with Gregory Cali and we’ve shared our conversation below.

Hi Gregory, what do you attribute your success to?
The most important factor behind my success—and the success of my brand—has been the solid foundation I was fortunate to be born into. I was raised by two loving parents who would do anything for me, and I have two brothers I deeply admire and share an unshakable bond with. Today, I’m blessed with a beautiful wife and two amazing kids. I would go to the moon and back for them, face any challenge, and overcome any obstacle just to see their happiness shine.

Alright, so let’s move onto what keeps you busy professionally?
About TheCaliLife

Over the years, I’ve always seemed to diversify my craft more than others around me. I was told to hone in on one thing and get good at it, but I often did my own thing. That meant exploring a broad spectrum of mediums. As a child, it started with the typical finger painting and drawings. As I got older, my math homework tended to have more drawings on it than math problems answered.

As a young teen, my friends and I were heavy into the skateboarding scene. I began shooting photos and filming skateboarding—the most creative sport ever invented, in my opinion. Being a skater enhanced my artistic train of thought and, I feel, greatly contributed to my art career. We made custom t-shirts with spray paint and stencils and edited skateboarding films with archaic techniques. VHS to VHS 😉

I started getting better at painting and eventually began painting murals in Encinitas and Rancho Santa Fe. Soon, it was time for college, and that’s when I took the next step as an artist. I graduated from Long Beach State University with a degree in drawing and painting. During college, I took a woodshop class where I created some sculptures, furniture, and other pieces that I still have today. I spent nine hours a day drawing and painting the human form in life drawing and life painting classes. I took watercolor so many times I lost count, and it really clicked with me. I sold my first piece of art from a gallery in Seal Beach, CA, during my time at CSULB, it was a watercolor of a fishing boat.

After graduating with my degree in art, I found a job from a Craigslist ad to become a sports photographer. I got hired to take photos and never looked back. I worked as a sports photographer in Long Beach right out of college. A colleague at the sports shooting company also worked as a wedding photographer on the side. He hired me to assist him at a wedding—and that broke the seal on what would unknowingly become a 16-year career as a wedding photographer and videographer.

A few years after graduation, I moved back home to Encinitas and ended up working at multiple photography studios in Del Mar and Carlsbad. I was working at two studios at the same time, and before heading to either one each morning, I worked as a surf reporter. I’d take pictures of the waves at sunrise and report back to the surf community with photos and updates.

I got hired on as a second shooter for a wedding company that was new to San Diego at the time. I stayed with them for over 10 years, eventually becoming their head photographer for all of San Diego County. During that time, I was also building my own network within the industry, knowing that in order to grow and build my own company one day, I’d need a solid team around me. That vision eventually came full circle, and today, I’m the proud owner of TheCaliLife Weddings.

TCLW is an all-inclusive weddings and events company that takes care of a client’s needs from start to finish. It’s a business my wife and I have both worked extremely hard to build, and we’ve established TCLW as a reputable, trusted brand in a competitive industry.

During my time in weddings, I was also doing photo and video work for corporate events, lifestyle shoots, and product shoots for brands both big and small. TheCaliLife Photo & Video also specializes in real estate photography and video, corporate headshots, portraits, music videos, branding and marketing videos for local businesses, and a whole lot more.

What sets me apart from others is my long-term, consistent dedication to the craft, and the unwavering optimism and belief I have in myself. That mindset was instilled in me early on by my parents, both incredibly positive role models and genuinely great human beings.

I also believe there’s something innate about doing what I do, something you’re born with. My grandmother was an extraordinary artist, and I truly feel she passed down a unique way of seeing the world. Her perspective on life and creativity lives on in me, and it’s shaped the way I think and create.

Over time, I fell in love with thinking creatively. It became a natural part of who I am, and eventually, it was bound to come out through art, photography, design, or whatever medium felt right in the moment.

I got to where I am by never giving up, by holding onto the belief that things will work out as long as I stay grounded and don’t fall into the negative distractions of the world. I’ve learned that the challenges we face aren’t meant to break us, but to teach us. The setbacks, the pain, the struggles, they’re all lessons. When we take the time to understand them, we can channel that experience into something meaningful and positive, rather than ignoring it or letting it weigh us down.

It wasn’t easy to get where I am today. Growing up as a skateboarder and an artist, I often felt like I didn’t fit the mold. I was told more times than I care to admit that I wouldn’t amount to anything if I kept heading down the path I was on. But I always had confidence in myself. I brushed off the negativity throughout my life, until I graduated college in 2007, which turned out to be one of the worst years in U.S. history to start a career. The economy had crashed, and suddenly, trying to build a life as an artist, already a difficult path, felt nearly impossible.

But I kept going.

In 2017, I opened an art gallery, only to have it burn down a year later. Just as that dream went up in flames, I tried to rebuild and reopen. Then, moments later, the world shut down as the COVID-19 pandemic hit. I had two young kids, was raising a family, and trying to build a business all at once. It was the hardest thing I’ve ever done, but also the most rewarding.

The road hasn’t been easy, but that’s the way I chose it. I’ve always believed in learning the hard way, because when you have skin in the game, you feel the impact. The challenges sharpen your perspective and deepen your growth. Just because the path has been hard doesn’t mean it’s been the wrong one.

In fact, I’ve come to see that the best road is rarely the smoothest, it’s the one with a few potholes along the way. Perfection isn’t beauty. True beauty needs contrast to be seen. It’s the good, the bad, and the ugly working together to shape something real.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
All of my best friends were born and raised here, just like I was. A typical week for us in Encinitas felt like a week-long vacation for an out-of-towner. Awesome! This place is nothing short of magical. It’s a memorable place, one that allows creativity to thrive and the sun to shine.

Most of my good friends that I’ve stayed in touch with are self-employed and have flexible schedules. We’d start each day with a surf session or a cup of coffee somewhere between Cardiff and Leucadia. We’d often cure our hunger at Le Papagayo in Leucadia or Besta-Wan in Cardiff.

Other restaurants we frequent include VG’s, Pipes Café, East Coast Pizza, El Nopalito, and a few of us have a soft spot for Round Table Pizza in Encinitas, where we’ve had plaques on the sports wall of fame for over 30 years. Go check it out 🙂

A couple of our go-to activities include tennis at a hidden court only locals know about 😉 hiking the lagoon in Cardiff, or climbing the mushroom caves in Annie’s Canyon.

Now that I’ve opened the art gallery here in Cardiff, I plan for the majority of my life to revolve around the energy I’ve created there. People have started to stop by, and the word is getting out. If any of my friends or family are coming to town, I always invite them to come hang out at The Cali Life Gallery.)

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
My wife, Rachel Cali, deserves a tremendous amount of credit for the success of my journey. She’s not only the love of my life but also my business partner. Together, we manage all three facets of TheCaliLife, and she still finds the time and energy to run two businesses of her own, thriving as a real estate agent and showcasing her talent as a skilled macramé artist. Her dedication, creativity, and support inspire me every day.

Website: https://www.TheCaliLife.com

Instagram: @TheCaliLife, @TheCaliLifeGallery, @TheCaliLifeWeddings

Facebook: The Cali Life Photography

Youtube: https://www.youtube.com/@GregCali-TheCaliLife

Image Credits
All images were taken by Greg Cali