Culture

Company Founder Q&A: 20 Questions on 20 Years

As Cross & Crown marks its 20th anniversary, we had the privilege of sitting down with founders Trevor and Tyler Roberts to reflect on two decades of growth, creativity, and innovation. From their early days as a design-first agency to becoming a full-service creative partner, their journey is a testament to passion, purpose, and lasting client relationships. In this Q&A, they share key insights into their leadership, challenges, and vision for the future.

1. Trevor, in the early days of Cross & Crown, you started as a design-first agency. What motivated you to pursue this approach, and how has it shaped the company’s identity over the years?

A: Purposeful design has always been a driving force for me. I love taking something valuable and enhancing it through pixel-perfect design. If you look at major brands, what truly sets them apart is their attention to detail and intentionality. It’s not about overdesigning, but about being purposeful. This approach started gaining us recognition, and 20 years later, I believe that this commitment to quality and precision still resonates with our partners.

2. Tyler, in 2004, what was your original vision for the company, and how has that vision evolved over the years?

A: Trevor and I grew up in and around Christian ministry, as our father was a Christian camp director. It was frustrating to see a gap in quality design between Christian organizations and other organizations. We wanted to close this gap. Something we found in our journey was that there is power in partnering with organizations to help them market their mission. It is amazing for us to build relationships and partnerships with organizations around the country and world where we can help amplify their missions to reach and impact more people.

3. Trevor, what was one of the biggest challenges you faced in the early years of building Cross & Crown, and how did you overcome it?

A: Time management was one of my earliest challenges. Tyler and I founded Cross & Crown while I was still in high school and continued growing it throughout my college years. This often meant squeezing in work between classes or staying up late to meet deadlines. The work was always rewarding and fueled my motivation, but balancing competing priorities was definitely a challenge.

4. Tyler, what has been the most rewarding aspect of your role as a silent partner, working primarily behind the scenes to ensure the business’s long-term success?

A: From early on, I was more on the “business side” of the company. I was getting my business degree when Trevor was starting to design for clients. This has continued as the company has grown. I have helped work on the business structure as well as explore new business opportunities. One of the more significant examples is when we were exploring a marketing strategy division; I managed all of this initially. Eventually, the needs outgrew my time and skillset, and we started building a team. Our marketing team now has four full-time team members.

5. Trevor, how would you describe Cross & Crown’s company culture, and what steps have you taken to cultivate it over the years?

A: I’d describe the culture at Cross & Crown as a high-performing, family-oriented environment. We prioritize work-life balance and maintain a strong family-first philosophy, understanding that people work to live, not live to work. With that in mind, we foster a supportive, fun atmosphere where we collaborate to create impactful, lasting work.

20 Years in 20 Seconds

Check out this 20-second highlight reel showcasing some of our video team's favorite moments from client projects over the past two decades.

6. Tyler, how do you think your role has helped shape the culture and vision of Cross & Crown over the years?

A: Our passion and vision to partner with organizations and amplify their mission have been at the core of what we have done from the beginning. One of the opportunities I enjoy the most is meeting with our leadership team to discuss business and supporting them as they grow as leaders. As a team, we are often discussing how to build into our company culture.

7. Trevor, can you share a milestone or turning point in the company’s history that really stands out to you as pivotal to its success?

A: One of the earliest milestones that stood out was winning the Creation Festival account in 2006. At the time, the Cross & Crown team was just three people, including Tyler and I. We initially worked on a small project for Creation Festival East, worth less than $150, but we approached it with a highly creative angle that stood out. This led to our biggest account at the time, managing the design for both Creation Festival East and West, Creation Cruises, Monsterpod, and other projects. These high exposure and large-scale projects helped us build international credibility with partners and sponsors of the festivals. Reflecting on it now, I can see how that opportunity opened countless doors—from video production at festivals in six different states to filming for Compassion International in Ecuador and printing the Creation Festival Newspaper on the same presses as USA Today.

8. Tyler, from your perspective, what are some of the key moments that helped transition Cross & Crown from a small graphic design business to a full-service creative agency?

A: Early on, Creation Festival brought us on to be their marketing team. This led to multiple Christian music festivals and other organizations trusting us with their marketing. In addition, the internal team has grown, adding more capacity and allowing us to take the next step.

9. Trevor, the 2014 introduction of digital marketing services marked a pivotal shift for the company. How did this addition change the way you approached client projects?

A: Digital marketing is an ongoing engagement, which has helped us strengthen our relationships with our partners by being actively involved in their marketing efforts and helping them adapt. This has reinforced our position as an extension of their team.

Our Digital Time Capsule

Our 20th anniversary page is a testament to the projects, people, and passions that have defined Cross & Crown since 2004.

10. Tyler, over the years, you’ve refined your process and offerings, like introducing web development, video production, and branding services. What’s been your favorite part of watching these services evolve?

A: The movement to holistic and full-service offerings is exciting. When we partner with an organization, we can pull from a wide variety of tools and resources to craft the best strategy and best meet the needs of our partners. Strategies can include a video campaign with retargeting that sends people to a custom landing page. Everything can be crafted in collaboration with our teams and designed to work together effectively. Seeing organizations benefit from these holistic strategies is exciting.

11. Trevor, what role do you see Cross & Crown playing in the creative marketing space over the next five years? What trends or innovations are you excited about?

A: As we approach 20 years of experience, it’s becoming clear just how much Cross & Crown has accomplished and how many solutions we’ve developed. Over the past two decades, we’ve had the privilege of working with countless organizations. However, the digital landscape is constantly evolving, and we remain committed to learning, adapting, and applying that knowledge to help our partners make a bigger impact. This can take many forms—whether it’s helping a 40-year-old business refine its brand to better connect with customers, optimizing a large nonprofit’s website for greater efficiency, or managing marketing efforts for a company without a dedicated team.

12. Tyler, Cross & Crown emphasizes building strong relationships with clients. How have you maintained that client-centric approach, especially as the company has grown and expanded its services?

A: Hearing the stories of the different organizations we partner with is always inspiring. We often hear that an organization couldn’t accomplish its goal without our partnership. Sitting down with a founder or principal and hearing their excitement about a product or service is always exciting. We then try to translate this passion into messaging that connects with the ideal person.

13. Trevor, Cross & Crown emphasizes empowering clients through creative solutions. What does “empowerment” mean to you in the context of the work Cross & Crown does for its clients?

A: At Cross & Crown, “empowerment” means equipping our clients with the tools, strategies, and creative solutions they need to take control of their brand, drive their vision forward, and make a lasting impact. It’s about more than just delivering a service—we aim to provide them with the knowledge, confidence, and resources to succeed long after our work is done.

14. Tyler, what role has technology played in the evolution of Cross & Crown, and how do you see emerging technologies shaping the company’s direction in the next decade?

A: Cross & Crown has always focused on leveraging technology to meet the needs of our organization partners. While we are not typically early adopters, we are keeping an eye on technology trends and testing possible solutions. AI is a hot topic now, and it will have a growing impact on our company offerings.

15. Trevor, what advice would you give to aspiring entrepreneurs looking to build a creative agency in today’s competitive market?

A: Prioritize team culture. A strong team culture is the backbone of a successful agency. Invest in your people, celebrate their strengths, and foster a collaborative, supportive environment that encourages innovation.

16. Tyler, as Cross & Crown has expanded its offerings, what considerations went into managing the company’s growth to avoid overstretching its resources?

A: From early on, we have been conservative in our growth. This has enabled us to retain employees through hard seasons (recession, COVID, etc.). Each new hire is an in-depth consideration and a long process to find the best fit to take us to the next level. A long-term perspective has always been something we tried to maintain. Sometimes we would bypass a short-term opportunity for something with more long-term potential.

17. Trevor, what’s one thing you’ve learned about leadership that you didn’t know when you first started Cross & Crown?

A: One leadership lesson I’ve truly embraced is the importance of appreciating people for who they are, how they think, and what they contribute toward the bigger goal. I wouldn’t want everyone at Cross & Crown to think like me—we need visionaries, doers, critics, and cheerleaders. The best projects come together when everyone plays their role to the fullest.

18. Tyler, what are the top financial or operational lessons you’ve learned from running a growing creative agency for 20 years?

A: For a small business to operate for 20 years, it has been important to stay conservative but think big. We have tried to avoid debt and add resources once we prove the model and know it is viable. I also explore market opportunities and test business models. If we find something viable, we will add more resources to grow it. Relationships are key in business. Our relationships with vendors, clients, and anyone we interact with have developed into trusting relationships over the years. There have been times when someone from 10 years ago remembered us and reached out to explore an opportunity. We strive to maintain positive relationships while recognizing that not everyone aligns perfectly with our values and vision.

19. Trevor, what excites you most about the future of Cross & Crown as it enters its next 20 years?

A: What excites me about the next 20 years is looking back at how far we’ve come in the last two decades and realizing that the impact we’ve made is just the tip of the iceberg. We’re only getting started, and there’s so much more opportunity ahead. I can’t wait to keep evolving and making an even greater impact.

20. Tyler, looking ahead, what aspect of Cross & Crown’s future are you most passionate about, whether it’s team growth, new services, or something entirely else?

A: Looking forward, I am excited about the team we have in place and the opportunities and markets we are exploring. Cross & Crown is poised in a solid position to take on larger and more complex projects. Additionally, we are continuing to deepen our offerings to better meet the needs of our partners. When we have the opportunity to build a consistent, ongoing relationship and really develop a solution that best fits the need, it is amazing to see the results. It is important to have more trusting partners to develop these relationships and explore building their organizations together.