Conversations with Bobby Toledo

Today we’d like to introduce you to Bobby Toledo.

Hi Bobby, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?

I just turned 40 this year. Like many people, I thought I needed to have my whole life figured out by the time I got here. But I had a huge shift about three years ago—one that completely rewrote the script of my life.
I grew up in Southern California and have been local to the Los Angeles area my entire life. As a kid, I was into punk music and ska, and played the trumpet in the marching band. But growing up trying to figure myself out, I knew something was different about me and pushed away a part of me that was core to who I am today.

Professionally, I went to school for communications public relations at Cal Poly Pomona, then became a trainer at the Apple Store. That pushed my career into corporate training, where I traveled across the country doing workshops. Eventually, I got married, had kids, and bought a house. I was living the “American dream” in suburbia, holding a corporate job where I managed training content production, opened new stores, produced live-streamed talk shows, concerts, and events, and facilitated leadership workshops nationwide.

Stepping Into Truth and Rebuilding

In 2023, I finally came out as gay. It was one of the most difficult periods of my life. I had been hiding the secret for 37 years, and it was finally eating at me to a point where I needed to come out to my friends and family. I lived in fear from a young age because I knew my parents were conservative Christians and wouldn’t accept it.

But I did it anyway. I came out to my wife, my parents, and my family. More people accepted me than I anticipated—with the exception of my immediate family. In a sense, I’d been masquerading as a different person my entire life, and for some people, they just didn’t know how to handle the sudden shift.

Fast forward to a year ago, and I’ve been on a continuous journey to find myself. I moved several times by now since coming out, experiencing things I’d never experienced before as a gay man. I lost my corporate job, and when that happened, I decided to lean heavily into the things I loved: being creative. I was feeling immense corporate burnout, but I loved being behind the camera and having fun with content.

Finding My Crew and Launching Smile Crew Media

I’ve been on a quest to find my people and community. I joined the Gay Freedom Band of Los Angeles (GFBLA) in January of 2024, a community band does marching, jazz and concert music. I hadn’t picked up my trumpet in 20 years and I was terrified, but being involved in GFBLA has given me a sense of purpose and a true outlet of creativity. I’ve marched many Pride parades and contributed to the marching and concert bands now for almost three years.

Disneyland has also been a huge factor in my journey and I bought an annual pass after many years of not having one. I met so many creators and groups at the parks, and some of them have become some of the best friends I’ve ever made. I changed my Instagram handle to ⁠@BobbyWithTheSmile⁠ and joked with my friends that we were the “Smile Crew.” It stuck and they helped me build my confidence, make content more frequently, and build the Smile Crew. People wanted to join our crew when we posted videos. I realized that the whole point of Smile Crew Media—which I officially launched in October of 2025—is bringing joy, fun, and community to the people around you. Because anyone can have a Smile Crew.

What started as making content for fun at Disneyland, turned into making short-form content, taking photos, and doing UGC-style work for other creators, brands, businesses, and nonprofits. Soon, I was invited to media events, red carpet experiences, food reviews, and brand collaborations. I even got my first tattoos, working with an amazing tattoo artist. I made so many amazing friends along the way, just by being open to new experiences.

Looking Ahead

Today, I’m an entirely different person than I was three years ago. I offer social media content creation, wedding content creation, and photography services. My relationship with my parents and family is getting better, I see my kids often, and I try to do fun things with them every time we’re together.
My life looks a lot different than the corporate job and suburban home I thought I always wanted. But the universe had a lot more in store for me: to find my crew, build a community, start my own business, and love what I do. Because everyone deserves their own smile crew.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It’s been far from smooth. Hiding a core part of your identity for 37 years out of fear of rejection from a conservative Christian family, dealing with corporate burnout, losing my job, moving out, and navigating the deep fear of stepping out from behind a mask to live authentically as a gay man was daunting. I’ve had to completely redefine my goals and what makes me happy over the past three years. This last year has especially been the hardest, building my own business from the ground up without really knowing what it should look like at first. On top of that, I’ve faced a lot of pressure from family to just go back to learning and development and find another safe corporate job—knowing deep down that it wouldn’t make me happy. Choosing fulfillment over comfort has been the hardest, yet most rewarding, battle of my life.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
Today, I run Smile Crew Media (@smilecrewmedia) – a content creation and visual strategy business based right here in Southern California. I specialize in short-form social media video content, brand photography, wedding content creation, UGC-style work, and dynamic event coverage for creators, businesses, and nonprofits.

What I’m known for—and what truly sets Smile Crew Media apart—is our focus on joy, community, and authentic connection. Because of my extensive corporate background in live event and content production, training, and leadership, I bring a unique mix of professional project execution and a deeply human touch to everything I film. I don’t just capture pretty images or trendy videos; I capture real experiences and help brands and individuals tell their authentic stories.

What am I most proud of? I am most proud of building something entirely from scratch that reflects my true self. After hiding who I was for 37 years and following a traditional corporate path, stepping out on my own to create a community where everyone feels welcome is a dream come true. I started with a simple handle change (@bobbywithasmile) and joked with friends about being a part of my Smile Crew, but it blossomed into a movement. Knowing that anyone can have a ‘Smile Crew’ – and that my work brings people together and spreads joy, makes every hurdle worth it.

If we knew you growing up, how would we have described you?
Growing up, I was a classic Southern California kid trying to find my place in the world. Personality-wise, I was energetic, deeply creative, and heavily involved in school music programs—I played the trumpet in marching band and lived for punk and ska music. I’ve always been someone who pushes boundaries, sees how far I can bend the rules, and I’m deeply sarcastic and quick-minded. I never liked sports or traditional boy things; I was always at my best when I was creating something beautiful, whether that was making music or taking photos. At the same time, I spent a lot of time trying to figure myself out and hiding a core part of who I was. Looking back, all those years of pushing boundaries, performing, and expressing myself creatively were actually the early building blocks of the storyteller and producer I am today.

Pricing:

• $250 for one short form reel
• $250 for a standard photo shoot
• $1650 for full day wedding coverage and 5 reels
• $800 for a half day event with 3 reels
• $500 for small event coverage with 2 reels

Contact Info:

• Website: https://smilecrewmedia.mypixieset.com/
• Instagram: https://www.instagram.com/bobbywithasmile/
• Facebook: https://www.facebook.com/bobbywithasmile
• LinkedIn: https://www.linkedin.com/in/bobbytoledo/
• Twitter: https://x.com/bobbywithasmile
• Youtube: https://www.youtube.com/@Bobbywithasmile
• Yelp: https://www.yelp.com/biz/smile-crew-media-fullerton

Image Credits
Bobby Toledo – Smile Crew Media