How We Hosted 5 Events at New York Tech Week

Toronto had been our testing ground for over a year. I'd personally hosted or partnered on 50+ events in the city. The platform worked. People showed up. Connections were made.

But there's a question every early-stage startup has to answer: is this working because the product is good, or because the founder is in the room making it work? Toronto was my home turf. That's not scalable.

New York Tech Week was the perfect stress test. Hundreds of competing events: major companies, well-funded startups, influencers all fighting for attention. If Escape could attract people in that environment, it could work anywhere.

I planned five events across the week, each designed to test a different format. Every single one was community-first. No panels, no sponsors, no pitches. Just people connecting.

We started from Sheep Meadow. The plan was simple: walk together, no name tags, no mics, no structure. 454 people had requested sign-ups. More than 100 actually showed up on the day.

And we all started walking together. That's the part I remember. Not a line of people with a guide in front. A group moving at roughly the same pace through the park, finding themselves in conversations with people they'd never have met at a panel or a mixer. The walk did the work. The format let people be themselves.

Charles Haycox thanked me afterward. He'd been to a different event almost every hour that week: fireside chats, AI panels, networking brunches. Hundreds of other tech leaders, major sponsors, high production value. He said the Central Park walk was his favorite. Just a walk. Just people. That hit harder than anything an investor could have said about product-market fit.

Not everything goes to plan. We planned a Puppy Yoga session. 114 people signed up. It got cancelled at the last minute due to venue issues. Having to message 114 excited people that their puppy yoga isn't happening is one of the worst feelings as an organizer. But hey, that's events. You plan, you adapt, you keep going.

Competing with big budgets. During Tech Week, companies with real marketing budgets host events with open bars, celebrity guests, and fancy gift bags. I had a park and a running route. There were moments where I questioned whether anyone would choose our events over a free cocktail party hosted by a Series C startup.

They did, though. Over a thousand times.

Solo logistics are brutal. Huge thanks to Kiana Hong for her support throughout Tech Week, from planning to on-site execution across all the events. But even with help, running five events in a week in a city where you don't live is exhausting. It reinforced something I already knew: I need a team.

Intentional events are rare enough to be remarkable. In a city where 900+ events are competing for attention, many with open bars, celebrity guests, and corporate budgets, people showed up to a park walk because it didn't feel like performance. The demand for curated, purpose-built gatherings in tech hubs is real and underserved. People are tired of the formula.

Movement changes conversation. Compare the numbers: 177 sign-ups for the morning run, 170 for the picnic, 114 for puppy yoga, 454 for the walk. The walk won decisively. Why? Because walking creates a different kind of attention. You're moving forward together, and there's something about literal momentum that makes people more open to strangers. You can't small-talk a walk the same way you small-talk a conference panel.

The RSVP-to-show-up gap is wider in NYC than Toronto. In Toronto, 60% of RSVPs actually attend. In New York, it was 35%. People are flakey here, or busier, or have more options. The difference forced me to think differently about community: not just about filling seats, but about converting interest into actual presence. That distinction shapes how I think about retention on the platform now.

I came back from New York with a notebook full of observations and a conviction that the v1.0 product wasn't going to cut it.

The app worked. But “worked” and “great” are different things. I saw attendees struggle with discovery. I saw organizers wanting tools we didn't have. I saw people connect at events and then have no way to maintain that connection through the platform.

That's when I made the decision to rebuild everything from scratch. The v2.0 release, with redesigned communities, AI compatibility, Vibe matching, multi-currency payments, and 300+ new features, traces back to that week in New York.

We came to connect. And maybe, just maybe, to get noticed too.

We're coming back. But I'm approaching it differently this time. Instead of flying in and hosting events myself, I want to empower local community leaders to build on Escape. Give them the tools, the platform, and the support, and let them create the experiences their communities want.

Thank you to everyone who showed up, shared stories, and reminded us what this is really about. Thank you to Kiana Hong for her tireless support from planning to on-site execution across all the events. And thank you to TECH WEEK by a16z for creating the space for builders like us to show up and create something real across NYC.

If you're building a community or hosting events, Escape is for you. Let's build something together.

Toronto → NYC → SF → the world.