We were lucky to catch up with Wilbert Cheng recently and have shared our conversation below.

Wilbert, thanks for joining us, excited to have you contributing your stories and insights. One of the things we most admire about small businesses is their ability to diverge from the corporate/industry standard. Is there something that you or your brand do that differs from the industry standard? We’d love to hear about it as well as any stories you might have that illustrate how or why this difference matters.

I have so much passion for the filmmaking and the creative industry. I started working as a solo filmmaker, which meant I really had to understand how to operate a camera, light a scene, create usable audio, all on my own. In a weird way, my lack of access made me self-reliant and gave me a really good understanding of different aspects of filmmaking. I learn as much as I can from everyone I work with and every production is different than the last.

My entrepreneurial spirit and small business mentality really came in handy with a project I did for Google. They were looking for individual creators who could create quality ads that would appeal to Gen-Z. When I won that pitch, I was given the budget and left to my own devices to bring this concept I promised I could create for them to life. I ended up serving as the producer, casting agency, director, cinematographer, editor, etc. While I wouldn’t recommend that experience for everyone, it was a great indicator of where the industry is headed and how I could be there to meet it. And it’s probably the work I’m most proud of for so many reasons.

When it comes to the industry as a whole, I find a lot of companies these days are taking their big production budgets and not necessarily minimizing it, but splitting it up into smaller productions due to the sheer demand for quantity. It feels like the days of hundreds of thousands of dollar shoots are getting more and more rare and businesses instead want to do ten, ten-thousand dollar shoots instead. As an industry, that’s a really difficult change for a lot of folks and understandably so.

I really pride myself in creating productions that can fulfill that need without sacrificing production quality. One way I’m able to do that is with some of the talent that I hire. We’re able to work in smaller production crews of 3-4 people at times and a lot of that has to do with building creative partnerships with incredibly talented multi-disciplinary filmmakers.

Wilbert, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

My name is Wilbert Cheng (I often go by Wilbs, Wilby), and I am a Chicago-based director/filmmaker who specializes in documentaries, social-media-focused, and tourism video production.

I consider myself a multidisciplinary filmmaker. You’ll often find me playing multiple roles on set, occasionally even being the only individual on a production acting as director, cinematographer, and editor. I’ve been incredibly fortunate to work with and develop partnerships with some incredible brands, such as Google, Jeep, Walgreens, The NHL, and Bosch.

I’ve worked at multiple ad agencies (FCB, OKRP, and Hogarth Worldwide) throughout my career all in various positions, from project manager to content creator and throughout my time there, I’ve always been interested in challenging the status quo of production. Finding ways to make the process more efficient for certain types of budgets and searching for talented individuals to work with. Those are traits that I took with me when I decided to officially start my own business two years ago. I’m still always in the search of innovative ways to bring my clients’ production goals to life.

Lastly, travel is a real passion of mine. While I regularly work in Chicago, I’ve been lucky enough in my career to travel the world for all sorts of projects. In the last few years of running my own business, I’ve been to numerous countries and dozens of cities around the globe shooting for tourism boards, fashion, and lifestyle brands. Coming up next, I’ll be headed to Australia for a very special project with RPM Steak with a team that I absolutely adore and I’m really looking forward to it.

Over the next few years, I plan to expand the business so I can scale up to larger productions when needed, as well as to create and cultivate a collective of talented filmmakers to help service these productions.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

This is the most unusual story and I love telling it since I think it’s a great story of how to pivot in your career.

I always grew up with a camera in my hand – I can blame my father and grandfather for that. I couldn’t tell you a family vacation where a camera wasn’t in my hand growing up. So the passion was always there, but as reality set in, I felt like it could never be a career.

As a result, I ended up going to school for economics and quickly realized that I wanted to work in advertising more than I wanted to work on Wall Street. Despite having a degree in Economics, I managed to work at a small boutique agency in Laguna Beach as an Account Executive which really showed me the foundations of agency life. Once I moved to Chicago to work at FCB, I realized that the business side of the industry just wasn’t for me. I started exploring videography and photography as a side hustle to build up experience. Shooting and editing projects for social media influencers was really where I had my start. As I started developing my skill set, my clientele eventually became small businesses. Eventually, it hit a point where I felt like I was a project manager by day and content creator at night. I had a really great boss at FCB (shoutout to Andy Ekland) who recognized where my passion really was and encouraged me to make a career pivot within the agency. Using my experience as a project manager, I helped develop the official Content Creator role and eventually filled one of those positions.

After working at a few agencies following my time at FCB, I really honed in on filmmaking as my true passion and where I wanted to take my career. In just a few short years I learned skills that I didn’t have access to before, and it was at that moment when I finally decided to go on my own and I’ve been directing projects for my own clients ever since.

So yeah, quite a big pivot from a degree in Economics. It’s an unusual journey, but one that I’m proud of.

Can you tell us about what’s worked well for you in terms of growing your clientele?

At the end of the day, leaving the client feeling great about the production is always one of the biggest priorities on set. I think that’s the key to not only externally growing your business, but also growing the business within your existing clients and network.

I regularly tell people that production is a bit of a performance. I couldn’t tell you the number of times I’ve been immensely stressed on set – lighting isn’t looking right, product doesn’t show, permits don’t come in on time, etc – but it’s always so so important to keep calm and come solution-oriented. On the flip-side of that, when things are really working, encourage everyone! A little positivity goes a long way on set.

Additionally, attention to the little things makes a significant difference. As a filmmaker who often works solo or with smaller crews, details like client monitors, craft services, Zoom feeds, and accommodating small requests can greatly exceed clients’ expectations. These thoughtful touches demonstrate that even smaller budget productions can deliver a high-quality experience, ensuring you remain top of mind for future projects.

Contact Info:

• Website: https://WilbertCheng.com
• Instagram: @Wilbyyyy
• Linkedin: https://www.linkedin.com/in/wilbertcheng
• Youtube: https://YouTube.com/@WilbertC

Image Credits

Photography by Hannah Schweiss, Brandon Bott, and Elise Pfister.