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The Origin Story: Why We Built Ollyeo

By Robert

Hello world.

We're stuck in a daily social media trap. We need to have more time in person with one another.

A year ago I left a secure UN career leading global digital solutions to bootstrap an AI startup that helps people actually connect in real life; tackling loneliness, building local community, and supporting local businesses along the way.

I decided to let go of my pride, get uncomfortable for a minute and share my story.

Here’s the long story of how I got here:

The landing

I'm an immigrant. In 2006, I came by myself from Romania when I'd just turned 19, as an international student. I had my first semester's tuition and rent paid and $300 in my pocket. So there I was in Los Angeles, nineteen, broke, barely any functional English, thinking this is the land of opportunity. The feeling of sinking settled in pretty quickly after. It was clearly a sink-or-swim moment, but the way I was parented in the Eastern Bloc, failing or going back wasn't an option .

What went through my head

There really wasn't much thinking or planning on my end going into this. My life experience until then had shown me that I could confidently deal with things as they came and they'd turn out well. I felt indestructible and fully capable of succeeding at anything I put my mind to. No fear, no doubt. I was either clueless or I'd intentionally shut my mind off from any doubtful thought, out of fear of facing a potentially disastrous outcome.

The culture shock

Growing up in Romania, I was that popular, confident, outgoing kid. Tight groups of friends everywhere and zero fear of the unknown. Ask a stranger for a favor? Call the mayor? Done, no hesitation. I figured my charm and optimism would work everywhere.

Everything I knew, places, foods, friends, family, was ten thousand miles away. My friends were all but lost, superficially exchanging an email every few months. But more critically, the soft skills required to function were no longer the same. Language, communication style, social norms - none of it was familiar.

I remember walking into a Subway, hungry. I found myself overwhelmed by choice patterns I didn't recognize, walked right out, and creepily waited until someone else walked in so I could follow them and listen to how they ordered. It didn't help that the options had no labels and I didn't even know the word for "lettuce", for some reason that word wasn't in my limited vocabulary. (In Romanian, the word for lettuce is salata, same as "salad"; so I asked for "salad" on my tuna sandwich and watched the poor server try to figure out what kind of salad this fresh-off-the-boat foreigner wanted on his tuna sandwich.)

I was going to a local community college. The buildings and classrooms impressed me from the get-go, and our teachers were phenomenal compared to what I was used to.Smiling, helpful, welcoming, accommodating. A sharp contrast to my teachers growing up, who were grumpy, threatening, abusive. I couldn't imagine these teachers whacking anyone with a pointer stick for not paying attention.

The students in my class were my first exposure to people my age. I figured this was how I'd crack the culture and build a new social circle. After all, I had so much to offer. I was nice, charming, smart. I could talk about any subject, be it philosophy, world politics, you name it. I had outside experience and a fresh perspective. Back where I came from, people would flock around someone with outside experience like bees to honey. Here, the "flocking" was more like vampires to a garlic-eating contest.

With the guys, I was clueless about their favorite baseball players - deep conversations weren't in your typical college kid's wheelhouse. And with the girls, the walls went up instantly . I remember asking a classmate to grab a coffee after class just to chat, and she immediately blurted out, "I just split up with my boyfriend, I'm not ready for a relationship." I was utterly dumbfounded. The typical student journey was car-class-car, no time spared in between.

Eroded confidence

My confidence eroded. I couldn't make American friends, I couldn't get a job, I couldn't even find opportunities to connect with people. The most confusing part was that everyone was so nice. Everyone would say "let's get coffee sometime," and then nobody would respond when I followed up. I know now that in Los Angeles, this is just a verbal tic and there's no real expectation behind it.

I remember seeing a group of people playing basketball at the park, and unlike the old me, I was full of doubt. I wanted to walk over and ask "can I play?" but then I started talking myself out of it:

What if they say no and I look like an idiot?

What if they say yes and I'm not good enough and I ruin their game - then I'm really an idiot.

It would be so weird to just randomly go ask.

They already have enough players anyway.

I walked away.

This kind of unfamiliar, horrible thought process started appearing everywhere. At school, I was no longer asking people to hang out. I wasn't even daring to ask someone for a pencil sharpener. Rejection was too painful and occurred too often. That last bit of confidence I was desperately clinging to was only allowed to surface when, by my skewed calculations, the odds of success were very high.

In the years that followed, the friend thing didn't really get better. I met people, there were international student groups, I made acquaintances, I had roommates. I wasn't really alone, but it was still somehow lonely. That confidence erosion lingered and transformed into a deep, masked, repressed depression.

How my brain rewired

Now the stakes were high, survival required no mistakes. That had kind of an accidental upside. The non-stop worry rewired my brain into constant problem-solving mode - always scanning, always predicting, always trying to find the root cause of whatever was in front of me. Driving past a pothole became a mental chain: why is it there? Was it the materials? Was it not reported? Is there a better way to report these? Someone cut me off in traffic and it was now my existential problem, it was my failure to predict the unpredictable, which I should have done better.

Stress became a crutch I relied on for energy and mental alertness. The system rewarded me with a tiny psychological pat on the back every time I accurately predicted an outcome or identified a root cause, and mercilessly beat me up for any wrong prediction or mistake. I was trying to solve all the world's problems, in and out of my control, no matter how small - because that way I'd never be unprepared and never miss an opportunity.

It was exhausting to live like this, but it also turned out to be excellent training - that same reflex: identify what can go wrong, break the problem down, find the cause, propose the fix - is what I've been excelling at during my entire career.

Identifying the problem

None of my knowledge was of any use for connecting with people and making friends. I tried to eliminate all the potential problems I could think of. Is it me? Am I being too pushy? Am I saying the wrong things? Is it my accent? My clothes? Should I try to blend in or stand out? Is it everyone else? Do people just not want new friends?

There wasn't one answer or one pattern to cover all possibilities. I cycled through the same questions for years. But through that process, I made some observations:

  • It's not just me - a lot of people are in the same boat, and most are masking it.
  • Connecting requires being vulnerable, and most people are uncomfortable with that.
  • There's a lack of entry points, a lack of opportunity to connect.
  • People are uncomfortable talking with complete strangers.
  • Regardless of differences, there has to be a common interest involved.

My perspective eventually shifted from whose fault is it to how do I overcome the psychological friction of making friends, and how do I create convenient opportunities?

First attempt

In 2014, I started building an app. (By this point I was running a small web development company - more on that in a minute.)

Platforms like Meetup existed and did largely the same things they do today: list events organized by the community. That solved some of the event discovery problem, but it still failed to overcome a few large obstacles:

  • The time it took to figure out what you could and would actually attend.
  • Going by yourself and introducing yourself to strangers in groups that were mostly already formed (what if they're weird?).
  • The psychological friction of will I be accepted?

Organizing events for small casual things, or searching for them, wasn't as simple as it could be either.

Thinking back to the basketball scenario as a guide, where I was too worried to ask to join that random pickup game, I had a mental dialogue:

What would make it frictionless for me to end up playing a pickup game in that scenario?

Well, the best way would be if I had a wingman, someone who knew those people and introduced me and said "let's play."

Okay, true, but that's just not going to happen. So what would make it easier for me to approach this group?

If I had an excuse. If, let's say, there was an event on Meetup saying "pick-up basketball on Saturday afternoon at this park," then walking up to those people would be completely acceptable.

But when I searched Meetup for an event like that, it simply didn't exist. I figured it just wasn't built for small casual things.

My solution had to be easier and reduce some of the friction. While working on the side, back then, I built an app that attempted to simplify connecting with people with a maps centric casual event planning / rsvp - It was never officially released. As soon as it was developed, I had to put it on hold due to some life events and financial constraints. Today there are a dozen variations of that idea, none of which really accomplish much more than helping you organize your kid's birthday party.

Career history

A quick detour for context.

After landing in the US, I needed a job. Like many, I applied everywhere but was turned down for more jobs than I knew how to count.

Eventually I got a first job, really low pay, installing security and automation systems in hotels and famous people's houses. From there I took every job I could get my hands on to survive. You name it, I did it.

By 2010 I realized there was no way I could get ahead through those kinds of jobs. I was out of money, and after finishing my Associate's degree I could no longer afford college. Luckily, I was proficient with computers - I'd spent my childhood as my neighborhood's IT guy and majored in computer science in high school. I decided to run my luck at starting a one-person web development shop. I started small, but I was already making more than in any other job I'd held, building simple websites for small companies at huge discounts. It was a lot more rewarding, too.

I refined my skills as I went, becoming an expert Googler and taking free online courses. My confidence grew. (One of the life-turning courses was coincidentally taught by Steve Huffman, one of Reddit's co-founders, on Udacity.) I could now build scalable apps.

In 2015, after some life events, my wife took a job across the country in Stamford, CT, and we decided to leave everything behind and start over in the NY area.

I managed to get a contract at the United Nations to help build a mobile app for UNICEF. It was a moment of luck where I happened to be the right person, in the right place, at the right time. A few months after I came on, the organization decided to take on a full digital transformation of all their partnership processes - which is the vast majority of UNICEF's business. I was identified as the person to lead that technical effort and was made responsible for solutioning, architecting, overseeing the design, and managing the technical development. A monumental endeavor where I spent the next decade innovating, developing, refining, and herding cats(serving 150 countries). The platform now enjoys tremendous success. It's the largest developed, well loved, used by thousands daily around the world, impacting millions of lives. I'm proud of it.

A year ago, emboldened by all of this experience, I decided to quit my cushy UN career and re-focus my efforts on the problem I'd planned to solve for so long. It's gotten bigger and uglier - my "making friends" problem now runs under the name "loneliness epidemic." It's a consequence of a broken social system, exacerbated by social media, and it's a $460 billion-per-year economic drag on the US alone, with a health toll equivalent to smoking 15 cigarettes a day. But I digress.

Why now

A lot has changed since I built that first version twelve years ago. Socially, it's much more accepted to admit that wanting to make friends isn't a weakness - it's a fundamental human need we've all neglected. Loneliness isn't a stigma anymore; it's a clearly evidenced part of life. Reputable studies show that 1 in 3 American adults feel lonely every week. The US Surgeon General has declared it a public health crisis; the WHO calls it a global epidemic. Entire platforms and business models have emerged to capitalize on this, from mental health apps to "best friends forever" apps; all aiming at the same issue from different angles, which itself shows how big the problem has become.

In 2024, on an absolutely gorgeous spring Saturday, I was taking a stroll through Geneva after an exhausting UN workshop. I'd been feeling less and less fulfillment from my work. I decided to take a day to be alone and reflect, meditate, pray, whatever you want to call it. I remembered my app, thought about the recent advances in generative AI, and had the brightest lightbulb moment I'd had in forever. A warmth and happiness I hadn't felt in a long time came over me as I realized: my wingman. It was staring me in the face. Gen AI was now capable enough to be my wingman in that pickup basketball moment.

The solution

For this to actually work, it had to solve four things:

  • Make it zero friction in finding an activity
  • Find people who are actually a good match
  • Not walking in as a stranger
  • While there, try and keep the conversation from lulling and getting awkward.

I imagined if I could...

  • I could simply chat with my AI wingman for a bit. I could tell it what I like - basketball, board games, hiking… it would gauge my communication style, some of my personality. One morning it pings me: Hey, how do you feel about coffee and board games this Saturday afternoon at ... Want in?
  • I tap yes. A few hours later, enough of the others that were matched to that group/activity have said yes that it creates the event, invites us and spins up a group chat. Nobody's talking yet; the wingman kicks things off with a light question, a joke, something low-stakes. By Saturday, I would’ve exchanged a couple of messages with three of the four. Nobody's a stranger.
  • I would show up...
  • Minutes in, my phone buzzes privately: How's it going?
  • I can tell it honestly "great, but Joe's taking over the conversation"; it can assess how others are feeling and quietly drop a message into the group chat proposing a quick icebreaker or a themed joke to rebalance things. Afterwards, I rate the experience, which sharpens the match for next time.

So I went to work and built this. Now, those concerns are addressed:

  • It removes the idea problem. I'm not sitting around trying to think of what to do this weekend.
  • It removes the planning problem. No calendar wrangling, no venue hunting, no chasing people in group texts.
  • It removes the stranger problem. The group chat warms everyone up before you're standing face-to-face.
  • It removes the awkwardness-during problem. A light-touch facilitator keeps things moving when they'd otherwise stall.

While I was getting excited about all the kinds of activities this opens up, I started thinking more about where they'd happen. I also wanted the app to be free to use, so people with limited disposable cash (thinking of myself at 20) could participate.

I went around and talked to local venue owners: restaurants, makerspaces, gyms. Every one of them was thrilled by the idea of paying a small commission per customer sent their way. A makerspace runs a paint-and-sip, and the wingman happens to know six local people looking to do an art project together - win, win, win.

But the most fascinating part of those conversations was that the owners cared much more about community than they did about spending a commission. Business is business, but the idea of their venue becoming a third place again, somewhere their neighbors actually connect, is the real why behind a lot of these foot-traffic businesses in the first place.

Currently

Now the app is built, the website is live, social-media accounts are active, and I'm launching it locally because this is where I live and where I've watched the problem up close. Every week on local community boards and social groups, someone posts asking how to make friends here. It's a young town full of people who moved in for work and are looking for connection. The venues are here and eager to be part of it. It all makes sense.

To ensure there is real value and active groups from day one, we are rolling out deliberately, starting with a localized waitlist to build critical mass.

I'm hoping that soon, I could have the minimal critical mass to launch. Fingers crossed.

Join Us

If you made it all the way here, thank you.

I’m doing this for the 20-year-old me who could have used a wingman, and for anyone today experiencing the kind of isolation I described. We have finally built a tool that uses technology to get people off their screens and into the real world.

We are building this alongside our community. Here is how you can get involved:

  • Join the Community: If you are excited by the idea of frictionless, real-world connection, join our waitlist. Every sign-up improves our ecosystem, creates better matches, and helps tailor local activities. Please share it with anyone who might need it.
  • Local Venues: If you run a local business with space for people to gather—like a coffee shop, makerspace, studio, or restaurant—and you want your space to become a true third place for the community, I'd love to meet you. We are actively partnering with venues to bring groups of locals to your doors.
  • Community Organizations: If you run a parent group, newcomer club, hobbyist meetup, or nonprofit, our platform can seamlessly power your gatherings. Let's talk about how Ollyeo can support your mission.
  • Experienced Builders: As a first-time consumer startup founder, I am always eager to connect with those who have successfully built consumer products or launched community platforms with network effects. I believe in learning from real-world experience. If you are open to a conversation, my inbox is open.
  • Partnerships: I'm actively exploring partnerships to help build this movement. If this is your space and our mission speaks to you, please reach out.

Thanks so much for reading.

Robert Founder & CEO, Ollyeo