We’re excited to introduce you to the always interesting and insightful Caren Leonard. We hope you’ll enjoy our conversation with Caren below.

Caren, thanks for joining us, excited to have you contributing your stories and insights. What do you think it takes to be successful?

Success as an entrepreneur is about three things: resilience, authenticity, and a willingness to learn and adapt. It’s not just about having a vision—it’s about staying true to that vision when challenges arise while also being flexible enough to pivot when necessary.

When I started Midnight Run Consulting, I knew I wanted to serve emerging brands and disruptors—businesses that were on the verge of something extraordinary, but needed the right strategy to get there. In the early days, I had to practice exactly what I preach to my clients: focus on telling real, authentic stories and staying creative in the face of changing circumstances.

For instance, an opportunity came from an iconic neighborhood establishment. They were loved locally, but needed help amplifying their story to attract a broader audience. I knew we couldn’t rely on standard marketing tactics to stand out, so we focused on what made them special: high-quality street food, community, and support of local artists.

That campaign reminded me that success doesn’t come from trying to outspend competitors—it comes from finding the heart of what makes a business unique and building genuine connections around it.

I’ve also learned that success is about surrounding yourself with the right people. I’ve built a network of incredible women in creative services who inspire and challenge me to push boundaries. One of my favorite sayings is, “The best stories aren’t written alone.” That’s true for my business and for life.

Finally, resilience is everything. As a mom of four with a growing business, there have been times when it felt like there just weren’t enough hours in the day. However, I remind myself that every challenge is an opportunity to grow. For me, success isn’t just about what I’ve built—it’s about staying grounded in my values while helping others do the same.

Caren, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

There’s a unique thrill in discovering the next new spot, the next big thing or a fresh idea—but there’s an even greater satisfaction in helping the world see it.

For nearly 15 years, that excitement has fueled my journey in the vibrant world of lifestyle and hospitality public relations. I’ve had the privilege of working alongside some of the most renowned people, brands and concepts in the industry. Through these experiences, I’ve gained a deep understanding of what truly drives growth—and what falls short.

From the beginning, I built my business on a simple yet powerful idea: PR needs to be reinvented.

Traditional methods that focus solely on pitches and placements don’t always lead to meaningful, sustainable growth. For a modern hospitality brand to thrive, it’s essential to create deep connections with your customers, your community and the culture around you. It’s about more than just building awareness—it’s about making an impact and earning genuine recognition. Not in the ‘scrolled by it in my feed way’ but in a ‘stopped and smiled’ kind of way.

This belief is what Midnight Run Consulting was founded on a decade ago, and it still drives us today. We’re ready to help the world see you.

Can you tell us about a time you’ve had to pivot?

In my PR career, one of the biggest lessons I’ve learned is the importance of pivoting when the industry—and your own instincts—tell you it’s time for a change. Early on, my PR work was very focused on traditional media relations. I was great at securing placements and helping clients get their stories out there, but I started to notice a gap. Media hits alone weren’t moving the needle for their businesses the way they used to. Clients were looking for something deeper—strategies that connected their stories to tangible growth and long-term impact.

That realization led me to a pivotal moment in my career: rebranding to Midnight Run Consulting. It wasn’t just a name change; it was a complete evolution of my approach. I shifted from focusing solely on media relations to offering a more holistic strategy that included branding, messaging, and even events. I wanted to be more than a PR agency—I wanted to be a partner in growth for emerging brands.

The transition wasn’t without its challenges. I had to educate my existing clients about this new approach and refine my messaging to attract the right kind of business. One of the most rewarding moments came when a long-time client came back to me after the rebrand and said, “This is exactly what we need.” They were launching a new concept, and we worked together from day one to shape their story—not just for the press, but for their customers, employees, and community. That project became one of my proudest achievements because it embodied the full spectrum of what Midnight Run Consulting is about: authenticity, creativity, and growth.

Pivoting was risky, but it taught me that staying true to your values while adapting to what your clients need is the key to long-term success. Looking back, that decision transformed my business and how I view my role as a strategic communicator.

Any advice for growing your clientele? What’s been most effective for you?

The most effective strategy for growing my clientele has always been about building organic, authentic connections rather than relying on hard sales. For me, it’s not just about pitching services—it’s about listening, understanding, and showing up as a genuine partner who’s invested in someone else’s success.

These authentic connections happen when you’re truly interested in people and their stories. I never go into a conversation thinking, how can I sell my services? Instead, I think, how can I help this person? By showing up with value first—whether that’s offering advice, sharing insights, or connecting them with someone in my network—trust is built naturally.

Referrals have also played a huge role. When you do great work and maintain genuine relationships, people talk. Some of my best clients have come from introductions made by happy clients or even past colleagues who saw the impact I made. It’s a slower, more organic way to grow, but it creates a foundation of trust and loyalty that hard sales could never achieve.

Contact Info:

• Website: https://www.midnightrunconsulting.com/
• Instagram: https://www.instagram.com/midnightrunconsulting/
• Facebook: https://www.facebook.com/midnightrunconsulting
• Linkedin: https://www.linkedin.com/in/carenleonard/