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Ray Sheehan : Must-Have Skills for Entrepreneurs in 2024


Ray Sheehan, Founder of Old City Media. Sit back as we explore the world of experiential marketing from an industry leader.


Can you tell us a bit about yourself and what got you into entrepreneurship?

Ray Sheehan is the Founder of Old City Media, a North American event production and experiential marketing agency. He has a background in strategic planning, marketing, event management, and advertising and has helped the company expand from one city in the United States to an international agency.


Before this role, Ray partnered with UpcomingEvents.com, a production company in Philadelphia, and worked for 20th Century FOX. He oversaw all aspects of the business and produced a nationally syndicated television show for FOX.


In 2020, he launched the G.I.F.T Program as part of Old City Media. Ray is recognized as a leader in the special events space, a marketing guru, and an innovative thinker in the Philadelphia community and beyond. Sheehan has been featured in Yahoo, Market Watch, Business Insider, The Super U Podcast, Medium, Street Fight, and more.


The reason I got into entrepreneurship was purely on accident. I just loved bringing people together at a very young age. I was able to turn that knack into a very suuccesful career in event production and experiential marketing.



What are the top three skills you think are crucial for entrepreneurs today?

1. Problem Solving

2. Communication

3. Passion


How do you think the role of technology has impacted these skills in recent years?

Technology gives us the tools to make better and smarter business decisions. It also helps entrepreneurs manage their time more effectively while also helping them streamline and scale their business.


Could you share a story with us about how you used some of these skills to overcome a challenge in your journey?

In life and business, the only constant is change. In 2020, the pandemic changed our world, and we were faced with the prospect of events not returning anytime soon. We created the GIFT Program to bridge the gap between our brand partners and their target demographic through high-traffic retailers. With over 40,000 events, we have a simple, flexible solution to successfully match brands and retailers.

The GIFT Program is a modern take on the pop-up sales activation where the customer always wins. We developed this solution for Fortune 500 companies, and it has been embraced by grocery chains, hardware stores, and other high-traffic retail locations.

The GIFT Program provides your brand with a platform for face-to-face engagement, lead generation, and brand awareness with your target demographic. The GIFT Program allows your retail store the opportunity to enhance the customer experience and add additional revenue by monetizing available floor space. The respected brands set up eye-catching displays at retail locations to engage with consumers and “GIFT” them with the host partner’s store gift cards. When the customer wins, everyone wins.



In your opinion, how important is it for entrepreneurs to adapt to changing trends and what do you see as the biggest trend in 2024?

We must always be able to adapt and pivot. Some trends you are going to see in 2024:

1. AI will become more mainstream and help solve more business problems.

2. Authenticity will become more important to consumers.

3. Brands will spend more money on non-traditional advertising due to an election year.

4. CSR (Corporate Social Responsibly) will continue to gain traction.

5. Big data technology will continue to push forward



What's one common mistake you often see new entrepreneurs make, and how can they avoid it?

Letting go...let your team become empowered.  They will surprise you!


How do you keep learning and growing as an entrepreneur?

Reading, Research, Podcasts, Networking and Listening...


Finally, what advice would you give to someone just starting their entrepreneurial journey in 2024?

Do not be afraid to take calculated risks. Always bet on yourself.






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