How Skylar used social media to get the first 100 users for his relationship app

Meet Skylar Gregory.

Skylar is based in Tempe, Arizona (USA). He is the co-founder of Evertwine, a mobile app with a simple but powerful mission: to bring people together in person through shared interests.

His journey to this point has been shaped by a lifelong entrepreneurial drive and a passion for building connections, both in business and in his personal life as an avid gym-goer and sports enthusiast.

The story told by Skylar Gregory

My entrepreneurial journey

I recently graduated from Arizona State University with a degree in Business Entrepreneurship, but my entrepreneurial journey began long before that.

After my freshman year, I launched a successful pressure washing company, learning firsthand the challenges and rewards of building something from the ground up. While that venture was profitable, I felt a pull toward solving a more profound problem, one I saw affecting my peers and my generation directly.

This led me to dedicate myself fully to Evertwine.

What is Evertwine?

The idea for Evertwine was born from a paradox: despite being the most digitally connected generation in history, Gen Z is also one of the loneliest. This isn't just a statistic to me; it's a reality I've seen play out.

The concept was truly solidified when a classmate shared a story about her friend who, after moving to Miami a socially connected city, still struggled to make friends. It was a clear sign that the old ways of meeting people were no longer enough. We needed a new solution, not just another app for endless online chatting, but a tool focused on creating fulfilling, real-world relationships.

My co-founder and I designed Evertwine to be that solution.

Eventwine is a mobile app that helps people combat loneliness by facilitating in-person meetups based on shared activities, whether it's grabbing coffee, going for a hike, or finding a new gym partner.

The platform is built on a pillar of simplicity. Users can browse a map or an explore feed to find activities happening nearby, create their own one-on-one or group meetups, and easily connect with others who share their interests.

Starting out

Our journey began in July 2023, initially with the idea of building a better dating app. However, we eventually recognized that the market was incredibly saturated and that our true passion lay in fostering platonic connections.

In October 2024, we pivoted to our current activity-based model, officially launching on January 1st 2025. The first few months were a quiet beta period focused on development.

Marketing wins

Building a community from scratch is a formidable challenge.

We acquired our first 100 users in about a month, primarily through bootstrapped, organic promotion on platforms like Reddit, X, LinkedIn, as well as word-of-mouth. This was our main marketing push beginning May 2025.

Below a few examples of the posts on X:

And an examples of what we posted on Reddit:

Built a new app to help people make real-world connections through activity-based meetups

Marketing challenges

While we're proud of our current 134 downloads, our biggest hurdle is achieving the critical mass needed for a network-based app to thrive. As a lean team of just two co-founders with limited capital, every decision must be strategic and resourceful.

Our early marketing efforts have taught us valuable lessons; for instance, while Reddit has been effective, our content on Instagram (example) hasn't yet found its footing, a challenge we are actively working to solve as we prepare to launch our first paid ad campaigns.

The business model

Our business model is B2C, with a traditional freemium subscription model coming soon.

We also have a B2B model where we have a business portal for businesses to partner with us and offer events and promotions through the app. This will have a subscription fee attached to it, but we are currently offering it for free and have our first business partnership started.

What’s next?

Looking ahead, our vision for Evertwine is clear.

We are focused on building a safe, engaging, and valuable platform. Our roadmap includes several key features designed to enhance the user experience, such as an optional ID verification system to ensure a trusted community, a gamification layer with points and badges to reward active users.

Furthermore we are actively working with apps and other businesses that offer happy hours, promotions, and deals at local spots. The goal is to show all of those promotions inside of our app, on both our map and explore view.

We are also developing a merchant dashboard for our partners and planning exclusive events to further enrich our community.

We are pre-revenue and focused on growing our user base for now.

We are just at the beginning of our journey.

Where to find Skylar Gregory and Evertwine:

• evertwine.social

• App store

• LinkedIn

• X

• Instagram