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

Gabriel, thanks for taking the time to share your stories with us today What do you think Corporate America gets wrong in your industry? Any stories or anecdotes that illustrate why this matters?

Corporate America often gets it wrong when it comes to understanding the importance of authentic connections and personalized experiences in the social media and tech industries. The current giants in the space are driven by algorithms designed to keep users scrolling, liking, and engaging on their platforms—but these interactions often feel hollow and transactional. It’s as if the human element, the very reason why we connect in the first place, has been stripped away in favor of vanity metrics and ad revenue.

Take the current state of platforms designed to “connect” us, for example. I’ve spoken to countless small business owners—local restaurant owners, boutique shopkeepers, and even hair salon entrepreneurs—who’ve shared the same frustrations. They tell me that platforms like Instagram or Google might give them visibility, but they lack the tools to foster real, actionable engagement. Customers “like” their posts but don’t show up at their doors, and ads cost a fortune with limited results.

That’s where Plinkd comes in. We’re intentionally building a platform that solves this disconnect. It’s not just about scrolling endlessly; it’s about creating real-life experiences through instant, authentic connections. For example, our public invitation feature allows users to invite friends, dates, or even strangers to local businesses, giving businesses immediate, measurable engagement. Corporate America has largely overlooked the value of genuine social and business connection, and that’s why I believe Plinkd is going to disrupt the industry in a major way.

Plinkd’s mission is personal to me. I’ve seen how small businesses struggle to compete in a digital world dominated by big corporations. I’ve also seen people lose the ability to truly connect with others beyond the screen. If we can bridge that gap and give people the tools to not only connect but experience their communities in new, exciting ways, we’ll have succeeded where Corporate America has fallen short.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

My name is Gabriel Middlebrook, and I’m the founder and CEO of Plinkd – People Linkd, a platform that is reimagining how people connect with one another and with local businesses in their communities. My journey into this industry was not a straight line—it’s been a path of challenges, grit, and a deep sense of purpose. I was a walk-on Division 1 athlete and a cancer survivor, and both of those experiences shaped me in ways I never expected. They taught me discipline, resilience, and how to stay laser-focused on a vision, even when the odds seemed stacked against me.

Plinkd was born out of my own experiences while traveling. I would find myself in unfamiliar cities wondering where the energy was—where people were hanging out, the best places to eat, or how to meet others with similar interests. Google and Instagram could show me places, but they felt disconnected and impersonal. There wasn’t an app that answered the question of “where’s everyone?” while also fostering authentic connections with the people and businesses around me. That’s when I realized: I didn’t need just another social media app or a search engine—I needed something that merged them into one seamless experience. And that’s how Plinkd began.

What sets Plinkd apart is its focus on being a total experience platform. It’s not just about looking up businesses or scrolling through endless feeds of curated images. It’s about creating real, actionable connections. With Plinkd, users can send public invitations to friends, dates, or even strangers, inviting them to specific local businesses. Businesses, in turn, can engage with their community in ways that are immediate and measurable. It’s a platform that not only connects people but also drives real-world interactions, supporting small businesses and local economies in the process.

One of the things I’m most proud of is how Plinkd is solving real challenges for businesses. For local restaurants, cafes, boutiques, and more, Plinkd serves as a powerful tool to instantly connect and engage with new customers who are already in their city. Imagine someone getting off the plane at the airport, checking into their hotel or Airbnb, and wondering where to go or what to do. Through Plinkd, businesses can reach these potential customers at just the right moment, providing them with an opportunity to showcase their offerings and build long-lasting relationships. We’re creating a seamless bridge between businesses and their communities, one connection at a time.

What I’m also incredibly proud of is the invitation feature. It redefines direct messaging, allowing users to break the ice in an organic way while also putting local businesses front and center. Whether it’s inviting someone to grab coffee, check out a new restaurant, or join a workout class, the possibilities are endless. Plinkd is designed to be intuitive and fun while solving real problems for its users—whether that’s figuring out where to eat or helping businesses capture new and engaged customers.

I want potential clients, followers, and fans to know that Plinkd is more than just an app—it’s a movement. Our motto, “Unlock Your Lifestyle”, captures everything we’re trying to achieve. We’re here to empower people to explore their cities, build meaningful relationships, and support local businesses. And we’re just getting started.

From entering the Harbor Entrepreneur Center’s Accelerator Program to partnering with the College of Charleston’s computer science department, every step we take brings us closer to realizing the full potential of this platform. For businesses, Plinkd is not just a marketing tool—it’s a way to connect authentically with travelers and locals alike, creating real value and driving growth.

If you’re looking for a platform that’s not just about likes and shares but about meaningful, real-world engagement, Plinkd is here to redefine what’s possible.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

One resource that has profoundly impacted my management and entrepreneurial philosophy is The Third Door by Alex Banayan. The book dives into the idea that life, much like a nightclub, has three doors: the main entrance where most people wait in line, the VIP entrance for the elite few, and the “third door”—the one where you have to hustle, think creatively, and sometimes break through barriers to make your way in.

This concept resonated deeply with me because it perfectly encapsulates my journey with Plinkd. As a Division 1 athlete and a cancer survivor, I’ve faced challenges that required me to find my own “third door” in life. Plinkd itself is a product of this mindset. I didn’t have a roadmap or a VIP pass to the tech world. What I had was sheer determination, the willingness to work 150-160 hours a week across two jobs to fund my dream, and a vision to create something that didn’t exist yet—a platform that connects people and businesses in an authentic, groundbreaking way.

The book also emphasizes the importance of resilience, creativity, and forging your own path when traditional methods fail. This lesson has shaped how I lead my team. I encourage innovation, push for creative problem-solving, and remind everyone that there’s always a way forward, even when the odds seem insurmountable. I’ve learned that success doesn’t come from waiting your turn—it comes from figuring out how to create your own opportunities and taking bold risks.

The Third Door has also influenced how I approach relationships and partnerships. The book stresses the value of persistence and the human connection, which I’ve found invaluable as I’ve built Plinkd from the ground up. Whether it’s cold emailing potential mentors or presenting Plinkd at accelerator programs, I’ve always leaned on the principles of persistence, curiosity, and hustle to break through.

What I find most empowering about The Third Door is that it reminds us that success is accessible to anyone who is willing to work hard and think outside the box. It reinforces the idea that the obstacles we face are not walls but doors waiting to be opened—if we’re brave enough to knock and persistent enough to push. This philosophy not only fuels my entrepreneurial journey but also forms the foundation of Plinkd’s mission: creating a platform that opens doors for people and businesses to connect, grow, and thrive.

We’d love to hear a story of resilience from your journey.

Resilience is the foundation of my journey, and my story with Plinkd has been a testament to perseverance, faith, and unwavering belief in a vision. Over the years, I’ve faced numerous setbacks that would have made many give up, but each obstacle became a stepping stone that pushed me closer to creating something truly special. Through it all, I’ve learned that even when things seem to not be going your way, God has a funny way of working things out in your favor. Every challenge I faced and every unsuccessful partnership became a vital part of Plinkd’s evolution.

When I first started Plinkd, I used my own hard-earned money to hire my first developer, investing $15,000 of my savings. Little did I know, that developer was double-brokering the app—pretending to work while subcontracting the work elsewhere and making no real progress. Losing that money was devastating, but it was also the moment the first iteration of Plinkd’s now-iconic orange gradient logo was born—a symbol of hope, even in disappointment.

From there, I sought help from two incredible friends, Ben and Reggie, who believed in me and invested in the dream. With their support, I hired a second developer to start over completely, rebuilding the app from the ground up with a focus on better UX/UI designs. This developer gave Plinkd its initial design language, but unfortunately, the code was cookie-cutter and unsustainable for long-term growth. Yet again, we had to pivot.

With my third developer, we finally managed to launch a beta version of Plinkd. This phase allowed us to A/B test, gather user feedback, and refine the platform. However, just as things were beginning to take shape, my developer had to leave for better job opportunities. During this time, Dylan stepped in to help with funding, ensuring the project could keep moving forward.

Now, I’m working with my fourth developer, who is refactoring the entire app from scratch. This is the hardest yet most rewarding phase—building a robust platform with a solid foundation to scale and thrive in the years to come. JP, another believer in Plinkd, stepped in to provide the investment needed to make this critical leap. Looking back, I see that every single developer who worked on Plinkd, regardless of how their time with us ended, contributed something valuable that helped shape the app into what it is today.

What makes this journey even more extraordinary is that it all happened while I was battling cancer. Between surgeries, chemotherapy, and radiation treatments, I worked two back-to-back jobs each week just to fund Plinkd’s development. On the days I physically couldn’t work, my mother, sister, and family stepped in to help me get through. Their unwavering love and support gave me the strength to keep going, even when everything felt impossible.

Plinkd isn’t just an app to me—it’s a testament to resilience, faith, and the power of community. It’s proof that even when the odds are stacked against you, perseverance and belief can turn dreams into reality. And just as God worked through all the challenges to turn them into blessings, Plinkd stands today as a platform ready to connect people and businesses in a way that’s never been done before.

Contact Info:

• Website: https://www.plinkd.com
• Instagram: https://www.instagram.com/plinkd?igsh=YTVodTkyZWFqdTV1