Santiago Ramos was just being a good wingman.
While the serial entrepreneur was living in Winston-Salem, his future business partner, Alexandra Kraft, was living across the ocean in Dubai and was facing a common problem: finding romantic connection was hard and the dating apps out there were just getting old.
“There’s a lot of swiping before you finally meet, and only then can you gauge whether there’s chemistry or connection,” Ramos says.
Ramos first met Kraft as his Airbnb host, and the two became good friends. On one trip to Dubai, Ramos and Kraft were hanging out at a beach club and, as these things do, the topic of dating came up
At one point, Kraft said, “It would be nice to see who’s here right now and be able to invite them to a beer. Why isn’t there an app for that?”
“Let’s build it,” Ramos said.
That idea was the origin of the networking app Wing Me, helmed by Ramos and Kraft. Within a couple months, the duo had their first minimum viable product, which they introduced to the market through in-person businesses in Dubai.
As Ramos and Kraft continued refining their product, they interviewed the owners of restaurants, bars, clubs, hotels, and more. Based on the feedback they received, they discovered there was a larger market for in-person connections of all kinds, not just romantic ones. They shifted, focusing now on shared experiences of all kinds.
After all, romantic connections aren’t the only ones that are difficult to make.
Today, the Wing Me app is helping people connect face-to-face, breaking down barriers that can keep connection from happening. Santiago’s own journey as an entrepreneur has been fueled by connections; it’s something he’s passionate about.
Early on, Santiago plugged into the entrepreneurial community of Winston-Salem, benefiting from the organizations and programming happening in this city. This year, he was able to give back to that community by using the Wing Me app to support the Techstars Startup Weekend held by Vision to Venture at Sparq, the iQ’s coworking space, helping to connect aspiring entrepreneurs just like himself.
When All You Need Is a Virtual Wingman
The Wing Me app helps people cultivate real relationships in real settings, taking away the lag time that exists in most networking apps, where you first chat online and then potentially meet up in person. It also gets rid of some of the unknowns that can come from introducing yourself to a stranger out in public.
After all, walking into a room full of people you don’t know well is daunting for most people, whether it’s in a professional or personal context. Even the most confident person can struggle with where to start in those situations. Do you approach someone first to talk, or should you wait for someone to initiate a conversation with you? If you do get to chatting with someone, what topic should you start with?
As a self-described introvert who worked for years to become more confident socially, Ramos built Wing Me for people like him who struggled with feeling on the outskirts of social situations.
“I think that life can be more interesting if people are able to come out of their shell and just be genuinely curious and present with other people,” Ramos says. “I want people to be able to do that. I know it’s not in everyone’s nature and so I’m hoping this tool can help people with that.”
What if, instead of walking up to people blind, you had an app on your phone that gave you some details about people in your space (like a brewery or a conference, for example) who were also using the app? You could learn their name, read a bit about them, and–perhaps the biggest hurdle–know that they’re open to connecting by virtue of using the app.
With a virtual wingman to ease the introduction, walking up to a person to initiate a conversation doesn’t feel nearly as daunting.
Connection is at the heart of any relationship, and Wing Me helps to move that connection piece along a bit, making it easier to get into an actual, in-person conversation more quickly than most networking apps.
“A good portion of my research in developing Wing Me has been analyzing existing tools for connectivity and seeing where we can fill the gap,” Ramos says. “And I think that our focus on that immediate in-person connectivity and hyper-local component sets us apart.”
Becoming Part of Winston’s Entrepreneurial Community
The idea of connection is woven through Ramos’ own story; it’s at the heart of his entrepreneurial origin story. Though Ramos was born in Colombia, he moved to the U.S. when he was four and came to Winston-Salem at the age of five.
As an immigrant with a different cultural background than many in Winston-Salem, Ramos discovered that finding his identity in this city was difficult.
“I remember starting to find myself over the years, once I started volunteering and tapping into my calling, which is helping people prosper,” Ramos says. “I learned that I need to have some equity around my cultural background and be able to present that to my community as a unique thing versus something I need to hide.”
He channeled that identity into creating connections through community organizing by working with Neighbors for Better Neighborhoods (NBN). NBN is a local non-profit committed to bringing low-resource residents into conversations with the potential to impact them directly. He later linked arms with Love Out Loud–a network of nonprofits, faith groups, and individuals–to help pioneer a food awards program for struggling families.
It was during this period that Ramos made his first foray into entrepreneurship by starting a landscaping business right out of high school. An attempt to scale that business led him to an especially fortuitous event–a lunch and learn event at Flywheel Coworking, which was located within the iQ at the time, in 2014.
“They had someone come in and just share the whole process of [entrepreneurship], from ideation to launch–things you need to think about and have established,” he says. “I remember thinking, ‘Wow, I’ve never been exposed to something like this!’
From there, Ramos found himself hungry for more entrepreneurial knowledge and networking, and he discovered that Winston-Salem was ripe with resources and opportunities in that space.
Before long, Ramos was attending entrepreneurial meetups regularly and soon he was asked to join the board of HUSTLE Winston-Salem, a nonprofit dedicated to advancing the local economy specifically by supporting underrepresented entrepreneurs. HUSTLE is a programmatic partner of Sparq, the iQ’s coworking space, which means Ramos can often be found networking around the startup community found there.
Ramos’ entrepreneurial endeavors began to expand as his connections and know-how did. His lengthy resume now includes experience in building customer pipelines for large manufacturers and a loyalty rewards app for the food and beverage industry. Eventually, he realized he was gaining lots of expertise he could pay forward to friends with businesses of their own, so he began spending time advising others’ ventures.
“There have been statistics that have come out saying that small business entrepreneurs and founders need at least one opportunity to plug into each week to stay motivated, to stay educated, and to stay abreast of innovation,” Ramos says. “The number one indicator for a sustainably successful entrepreneur is developing peer-to-peer founder relationships.”
By developing Wing Me, Ramos has found another way to help entrepreneurs connect.
Bringing Entrepreneurs Together
As Ramos spent time in Sparq, he started collaborating with Mike Buckovich and Kami Leslie, two Sparq members who run Vision to Venture. The Vision to Venture organization exists to help entrepreneurs like Ramos succeed in their business ventures, and the trio struck on the idea of using Wing Me to support another program aimed at helping burgeoning entrepreneurs–the Techstars Startup Weekend.
At a Startup Weekend, participants arrive on Friday with a new idea. Over the next 48 hours ideas are pitched, the audience votes on which ones the participants will pursue, and then everyone gets to working on their concept. Ultimately, the participants present their idea to the group as a pitch–complete with prototyping, market research, and more. Mentors and advisors are there to provide expertise and perspective throughout the whole event.
“It’s almost like space camp or band camp, where you’re with like-minded people and constantly working on something,” Ramos says.
This year marked the sixth Startup Weekend Ramos has been a part of. He started as a volunteer photographer for his first event and evolved into participant and mentorship roles. It’s an event he believes can give entrepreneurs a valuable boost.
“You learn how to work with people, you learn how to pivot very quickly from one idea to another,” Ramos says. “And it really shows you where your strengths are, plus you get a lot of mechanics around business and startups and how all that works. A lot of people come in not knowing much about that.”
In 2024, Wing Me was incorporated as an element of the Techstars after party. This year, Wing Me was one of the sponsors of this year’s Startup Weekend, hosted in the iQ, but the app was also actively used during the event. Attendees had the chance to use the networking app to make meaningful connections throughout the weekend
At the event, new app features were introduced, allowing organizers to relay messages, create group chats, and add name and title to special guests’ information. Instead of seeing a standard guest list, participants had access to a dynamic guest list through the networking app. It included organizer content like agenda, sponsors, and mentors, all with helpful links.
There’s something quite poetic about the way Ramos, someone who benefitted from the welcoming, collaborative, and connected entrepreneurial community in Winston-Salem, ultimately built a tool to help fuel those exact things even further–right where it all began for him.
Ready to start using Wing Me, “your copilot for a successful social life in real life,” yourself? Download the app here. Or maybe you’re more interested in learning about the ecosystem that supported Ramos. In that case, dive in by checking out Vision to Venture.
