Why I built Ollyeo

I still think about a basketball game 20 years ago in Los Angeles, that I never played in.

A group of people were playing in a park, and I wanted to join. I knew what to say: "Can I play?" But before I could ask, I'd started working through all the ways this could go wrong.

What if they say no? What if they say yes, but I'm not good enough and ruin their game?

I'd managed to make both answers sound bad. I walked away.

What bothered me was how unfamiliar that felt. Back home in Romania, I'd been outgoing and surrounded by friends. Starting a conversation, asking a stranger for a favor, even calling the mayor: none of it worried me. Now I was struggling to approach a few people doing something I wanted to do.

When I came to the US in 2006, I'd just turned nineteen. I arrived alone, as an international student, with my first semester's tuition and rent paid and $300 in my pocket. Beyond that, my plan was mostly to be optimistic.

I assumed I'd figure things out as I went. My English was limited, but I was confident. I hadn't given much thought to how much of that confidence depended on knowing how everyday life worked.

I remember walking into a Subway, hungry, and getting so overwhelmed by the ordering routine that I walked straight back out. I waited for someone else to go in, then followed them so I could listen to how they ordered.

I was missing some useful vocabulary, too. In Romanian, the word for lettuce is salata, which also means salad. So I asked for salad on my tuna sandwich. The server tried to work out which salad I wanted. I tried to work out why this was a difficult request.

I thought college would be where I found my footing. The teachers were helpful and welcoming, and I was surrounded by people my own age. Surely I'd make some friends there.

But the conversations and social habits I knew didn't carry over as easily as I'd expected. People often went from their car to class and back to their car. I couldn't work out where the part about getting to know each other was supposed to happen.

The confusing thing was that people were friendly. Someone would suggest coffee sometime, and I'd think, great, let's do that. Then I'd follow up and nothing would happen. I kept wondering whether I'd misunderstood something.

Was it my accent? Was I too pushy? Was I saying the wrong things? I went over these questions far more often than I found answers.

After a while, I asked less. I waited until I felt fairly sure I wouldn't be turned down. Even borrowing something in class could become a small negotiation with myself. The person who had moved across the world without much hesitation was now overthinking a pencil sharpener.

In the years that followed, I had roommates, met other international students, and made acquaintances. I wasn't alone, but I was lonely. Over time, that became a depression I mostly kept to myself.

That afternoon in the park was one of many small moments when I wanted to take part and talked myself out of it. It stayed with me because the thing I wanted was right there. I could see the people. I liked the game. And I still couldn't bring myself to ask.

For a long time, I kept picking apart what I might be doing wrong. Gradually, I started paying more attention to what made it easier to approach someone in the first place.

A shared interest helped. So did knowing that other people wanted to meet someone new. And having a reason to be there mattered enormously.

If that basketball game had been an open invitation to play on Saturday afternoon, I could have arrived knowing I was expected. If someone had introduced me, I could have spent those first few minutes learning names instead of wondering whether I was intruding.

I began thinking about how to create more of those openings.

By 2014, I was running a small web development company, and I started building an app on the side. It used a map to help people find and organize casual activities nearby.

Meetup already helped people discover events. But when I looked for the small, everyday things I wanted to do, I often couldn't find them. And even when I found an event, I still had to decide whether I'd fit in and work up the courage to go by myself.

I wanted to make that whole process easier. The first app was an attempt. I built it, but life events and financial constraints meant putting it on hold before it was ever officially released.

In 2015, my wife took a job in Stamford, Connecticut, and we moved across the country. I found a contract building a mobile app for UNICEF. A few months later, that grew into leading the technical work on a much larger effort to digitize the organization's partnership processes.

I spent the next decade helping design, build, and improve a platform used across 150 countries. There was plenty of problem-solving and a fair amount of herding cats. I'm proud of that work. It gave me experience taking a complicated idea and turning it into something people could use every day.

The app I'd put aside stayed in the back of my mind.

In the spring of 2024, I was in Geneva after an exhausting UN workshop. It was a beautiful Saturday, and I went for a walk on my own. I'd been feeling less fulfilled by my work and wanted some time to think, reflect, pray, whatever you want to call it.

I remembered the app. I thought about what generative AI was becoming capable of. And the basketball question came back to me.

My wingman.

I could see a way to build something that learned what a person enjoyed, suggested a plan, helped bring a group together, and made the introductions. Some of the work I'd imagined a helpful person doing now seemed possible with software.

I felt a warmth and excitement I hadn't felt in a long time. I wanted to work on this again.

Eventually, I left my UN career to build Ollyeo full time.

Ollyeo's AI social wingman is called Olly. Olly gets to know you through conversation: what you enjoy, what interests you, and what you'd like to do with other people. It brings you specific ideas for small, local gatherings and helps coordinate the people and details.

Here's the kind of experience I had in mind. You tell Olly you enjoy board games and would like to meet more people nearby. A proposal comes your way for coffee and board games in Stamford on Saturday afternoon, with a specific place and time. You can say whether you're interested.

Once enough people are interested and any needed venue arrangements are confirmed, the event is created and a group chat opens. Olly helps with introductions and gets the conversation started. Before Saturday arrives, you have a chance to exchange a few messages with the people you'll be meeting.

Then you show up.

You also have a private line to Olly around the event if you need a hand. It can offer support or help the group with an icebreaker. Afterward, you can review the experience and reflect privately on the people you met.

That's the experience I've been building: a plan that comes to you, help getting it organized, and a chance to get acquainted before you arrive. I want people to spend more of their time enjoying each other's company, with less of the effort and uncertainty that can stop a plan from happening.

As I worked on Ollyeo, I started talking to local venue owners about where these gatherings could happen. Restaurants, makerspaces, gyms. I wanted to understand whether bringing small groups to their spaces would be useful to them, too.

They were enthusiastic about the business opportunity. What stayed with me was how much they also cared about community. They wanted their spaces to be places where neighbors met and spent time together.

That made the idea feel more tangible. A makerspace could offer a paint-and-sip, and Olly could help bring together a handful of local people who wanted to try an art project. The activity, the people, and the place could all support one another.

I also kept thinking about myself at twenty, when money was tight. I want the core Ollyeo experience to remain free, so the cost of using the app doesn't become another obstacle to taking part. Building something useful for local businesses is part of how I want to make that sustainable.

Today, the member and partner apps are built. We're opening access by invitation in Stamford, Norwalk, and nearby Connecticut communities, using a local waitlist to bring people and places together as we roll out.

I'm starting here because it's where I live. On local community boards, I regularly see people asking how to make friends in the area. Some have moved here for work. Others want to meet more people or find something different to do. There are places to gather and people who would like to go. I want to help those plans happen.

The next step is learning from people taking part: which plans they enjoy, what helps them feel comfortable arriving, and what makes them want to come back.

I'm building this with the twenty-year-old me in mind. I also hope it's useful to anyone who wants more people to do things with, whether they've just arrived in Connecticut or have lived here for years.

If that sounds like something you'd enjoy, join the Ollyeo waitlist. It helps us see where people are interested, and we'll let you know when access opens for you. If someone comes to mind as you read this, please share it with them.

If you run a local venue, organize a community group, or have experience you'd like to contribute, I'd love to hear from you.

Thank you for reading. I still think about that basketball game. I'd like more afternoons to end with someone getting to play.

Robert Avram Founder, Ollyeo