Brilliance meets boldness in today's Wantrepreneur to Entrepreneur Spotlight as we feature Rachael Chestnut, founder of The Play Nice Agency. From her fascinating transition out of civil service and corporate communications to launching a creative powerhouse that's revolutionizing brand storytelling, Rachael's journey exemplifies the impact of putting people first in business. Her agency's groundbreaking work showcases how she's redefining the intersection of creativity, community, and commerce.
Hi, Rachael! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?
The Play Nice Agency is more than just a marketing and branding agency—we’re a team of fearless creatives committed to building iconic, human-centric brands that resonate deeply, ignite meaningful conversations, and spark cultural movements. From breathing fresh life into legacy brands to crafting new ones from scratch, we specialize in connecting businesses with the human experience in ways that differentiate and inspire.
We proudly serve a highly diverse portfolio of clients from Startups to Fortune 500 companies, to lifestyle brands, and Tech companies – we deliver results anchored in collaboration, creativity, and sustainable growth.
We partner with clients at every stage of their business growth. Acting as an extension of their teams, we collaborate to craft bespoke strategies tailored to address unique business models and challenges. These efforts amplify industry influence, elevate brand recognition, and foster customer loyalty—all while driving real, measurable growth. We combine strategic storytelling with authentic branding to transform businesses from the inside out, turning their brands into unforgettable experiences.
Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.
One of the defining moments in my career was when my agency secured a contract with The Washington Commanders to create the country’s first rotating art exhibit in an NFL stadium lounge. It was a project that pushed us into uncharted territory, both creatively and professionally. Working with local DC artists, we reimagined the stadium’s largest lounge under the theme “The Vibrancy of Change.” This included crafting immersive art experiences, launching a dedicated eCommerce art website, and designing branded lounge collateral for both The Washington Commanders and Sire Spirit.
The impact of this achievement was profound. This was not only a high-profile client, but also an opportunity in an industry we’d never entered before. The project had tight deadlines, complex logistics, and a host of key stakeholders, making it a monumental challenge. Yet, we delivered a one-of-a-kind experience that celebrated art, football, and community. It put our agency on the map, earning us recognition as a household name in our field. It also fundamentally reshaped the way we approached new clients—with boldness, confidence, and the belief that no challenge is too great.
Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.
For over a decade, my career took me through some incredible experiences—first as a civil servant working on "super-secret squirrel stuff" in government and then as a corporate communications leader for one of the world’s most prestigious consulting firms. By all accounts, I was thriving professionally, yet something essential was missing. I began asking myself a critical question: “Am I truly making a difference?”
I couldn’t confidently answer “yes.” Despite the valuable work I did, I found it hard to see how I was improving people’s lives or transforming the way business is conducted. Business often felt transactional, impersonal, detached from the very people it aimed to serve—and that didn’t sit well with me.
I wanted more. I wanted to create tangible change and foster a better way of doing business—one where people, relationships, and honesty are at the core. I wanted to show that organizations can build trust, communicate transparently, and deeply value the individuals they serve.
This realization motivated me to take the leap and start my own agency. I wanted to fill the gap I saw in the marketplace—bridging "business as usual" with impactful, people-centered work. Building something that not only makes businesses better but also restores faith in their potential to make a positive difference is what drives me every day.
Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?
Two indispensable tools that have transformed the way we operate are Notion and the Adobe Suite. Here’s why these tools have such a huge impact on our business:
Notion has become our central hub for all things project management. It’s more than just a workspace—it’s an all-in-one tool that keeps our team organized and our clients in the loop. We use Notion to organize project deliverables and deadlines. Its flexible structure allows us to break down tasks into manageable steps while keeping everyone on the same page. Our clients love the transparency Notion provides. They can log in and view all the project details in one convenient spot, making communication seamless, and real-time collaboration easy.
When it comes to powering our creative work, the Adobe Suite is non-negotiable. It’s the backbone of many of our client projects, especially when we’re creating graphics and designing engaging visuals. Adobe Illustrator is our go-to for graphic design. The tool’s precise editing features allow us to create stunning visuals and easily export or transfer artwork to other Adobe tools when needed. The interoperability of the Adobe Suite is unmatched. We love how easily we can move designs between applications like Photoshop, After Effects, and more to utilize the full spectrum of design capabilities.
We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.
For me, that moment came when our agency lost a major contract with Northwestern Mutual.
We poured months of effort into securing this partnership. Endless proposals, strategic pitches, and numerous meetings with the firm’s leadership. It wasn’t just another opportunity—it was THE contract, the one that could have catapulted our business to a whole new level.
And then, we lost it, without explanation.
Losing contracts is part of the job as an agency leader. It happens. You win some, you lose some—it's the nature of the game. But this one hit differently. It didn’t just disappoint us; it drained us. The entire team felt defeated, spent from all the work, only to walk away empty-handed.
At first, the loss felt crushing. But it didn’t take long for us to realize that being pushed to our lowest moment also gave us a powerful opportunity to shift our mindset. That loss wasn’t the end of the road—it was the turning point we didn’t know we needed.
Until that moment, we believed hard work and sheer determination were the core ingredients to success. If you just pushed hard enough, success would follow. But this experience taught us that’s not always the case. The truth? Failure often opens the door to something greater.
The Northwestern Mutual loss pushed us to reassess how we approach opportunities. We stopped chasing every prospect with blind ambition and learned to focus on finding the right opportunities for us. Instead of tying our success to winning contracts alone, we began valuing the type of work we pursued and how aligned it was with our team’s mission, culture, and talent.
This mentality has since become a core philosophy for our agency. Work hard, but don’t tie your worth to every outcome. Trust that the right opportunities will come to you—and when they do, you’ll be ready.
Looking back, losing that contract wasn’t the setback it felt like at the time. It was the pivot point that changed everything. It made our team stronger, more resilient, and more intentional in everything we do. And for that, I couldn’t be more grateful.
What unconventional strategy did you employ that significantly impacted your business?
One of the most unconventional, yet impactful strategies I employ as an agency leader is my hands-on involvement in every client engagement we secure. Unlike the traditional leader’s approach of delegation and overseeing from a distance, I immerse myself in the day-to-day details of project work and, yes, even partake in the grunt work. While this may raise eyebrows among other agency leaders who believe such tasks detract from one’s strategic responsibilities, for me, it's a deliberate and rewarding choice.
By engaging directly with projects, I gain nuanced insights into our clients' operations, challenges, and ambitions. This level of familiarity creates a foundation of trust and collaboration built on mutual understanding. I want our clients to feel that their success genuinely matters to us—not because they’re a revenue stream or a portfolio highlight, but because we see ourselves as true growth partners. By personally investing my time and effort into their projects, I reinforce this commitment.
My hands-on approach sends a strong message to both our clients and team members. To clients, it demonstrates a deep respect for the trust they’ve placed in us. To my team, it reinforces a collaborative culture where no task is beneath anyone and every role contributes to the bigger picture.
What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?
Perfection is the enemy of progress.
Running an agency means working in a fast-paced industry where creativity and strategy collide. However, one of the greatest challenges you’ll face is battling the illusion of perfection.
Remember this: neither you, your team, nor your clients are perfect. And that’s okay. Striving for perfection often leads to unnecessary stress and delays, diverting energy from meaningful progress. Instead, focus on doing your best every single day and trust in the value of consistent growth. Shift your mindset to focus on tangible growth goals that keep you motivated and moving forward. Take strategic risks. Be bold, but calculated. Learn from imperfection. Mistakes are inevitable. Use them as an opportunity to evolve, improve, and gain insights about your business.
At the end of the day, perfection is unattainable, but progress is infinite. Show up, do the work, and celebrate wins—no matter how small.
Want to dive deeper into Rachael's work? Check out the links below!
- Visit The Play Nice Agency's website theplayniceagency.com
- Follow The Play Nice Agency on Instagram @theplayniceagency
- Find the Play Nice Agency on LinkedIn
