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✍🏽 Landon’s Loop #149

What’s in the Loop:

🎙️ Chicago Futurist Vol. 10 with Draymond Washington, Founder of Three Cities Social Club

🧠 Google DeepMind’s Upcoming Chicago Hackathon

📅 8 Events in Chicago This Week

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🎙️ Chicago Futurist: Draymond Washington, Founder of Three Cities Social Club

Draymond Washington moved to Chicago without knowing anyone. Instead of waiting for the city to open up, he built a system to make it happen for others.

Three Cities Social is a modern membership club designed around one idea: adult friendship doesn't form by accident. It needs structure, repetition, and intentional design. With events across 40+ neighborhoods and 300+ members, Draymond is quietly building one of Chicago's most interesting community experiments.

Here’s our conversation:

You moved to Chicago without knowing anyone. What did you realize was broken about how adults try to make friends?

DW: Most adult socializing is passive. You go to a bar, a networking event, a workout class and hope something happens. But there’s no structure and follow up becomes hard. Friendships don’t form easily in environments that aren’t designed for them.

What’s broken isn’t people. It’s how we meet. Three Cities is built around connection by design. Hosted introductions. Small group formats. Recurring touch points. We reduce friction and increase repetition.

Friendship needs infrastructure.

Private clubs usually monetize status and exclusivity. You talk about connection and community. How do you balance aspiration with accessibility?

DW: Aspiration doesn’t have to mean exclusion. Our aspiration is about quality and depth, not status. We invest in thoughtful programming, strong design, and consistent culture. That creates a premium feel. But accessibility is built into our values. You don’t join to be seen. You join to belong.

Soho House has defined the modern private club for a generation. Are you building an alternative to that model, or a direct competitor? Where do you win?

DW: We’re not trying to replicate Soho House, but you are always competing with anything that is membership based.

They optimize for design, dining, and are tailored toward creatives. We optimize for day-one belonging. Where we win is intentional facilitation. Hosted introductions. Structured dinners. Cross-neighborhood representation.

Three Cities - River North

We’re building a relationship engine for the city, not just a hospitality brand.

Your core demographic is 25 to 45, with a focus on 30 plus. What happens psychologically at that age that makes this product resonate?

DW: Around 30, a few things shift. College friends scatter. Work becomes more transactional. Life gets busier. People get more selective about their time. You realize you have a lot of acquaintances but fewer real friendships. Psychologically, people move from exploration to intention. They want depth over volume.

Three Cities resonates because it removes the awkwardness and inefficiency from building adult friendships at a stage where time is limited and standards are higher.

Chicago is a city of neighborhoods that rarely overlap. Do you have any unique stats or metrics on how Three Cities has helped bridge the gap?

DW: We’ve hosted events in over 40 Chicago neighborhoods.

Every month, we run a three-hour curated neighborhood tour where I personally share fun facts about the area, highlight local businesses to support, and guide a walking experience that gets members out of their usual bubble.

We organize museum tours to expose members to different cultures and perspectives. We host dinners and outings in neighborhoods people might not normally visit. And we partner with local businesses to activate their spaces and bring our community into theirs.

It’s intentional. We don’t just say we’re citywide. We show up citywide. When someone from Lakeview is exploring Hyde Park, or someone from Bronzeville is having dinner in Bucktown with people they just met, that’s the bridge.

What are examples of technology you’ve used to manage your operations or club’s experience? How are you thinking about AI?

DW: We’re building our own app.

As we’ve grown, I’ve learned that intimacy does not scale automatically. When we had 100 members, I could personally connect people. At 300 plus, that breaks.

The app is focused on three things:

Structured day-one introductions
Smarter pairing of new members
Easier formation of cohorts around shared interests, life stage, and goals

The bigger you grow, the easier it is for someone to feel like they don’t quite fit. We want the opposite. When someone joins, they should immediately know where to start. AI will help us maximize pairing. We can use it to surface shared interests, similar backgrounds, engagement patterns, and even complementary personalities. It allows us to be more intentional at scale.

But the goal isn’t digital community. The goal is better in-person connection. Technology supports the experience. It doesn’t replace it.

What does retention look like in a business built on relationships? How do you measure whether members are actually forming meaningful connections?

DW: Retention is behavioral. We look at visit frequency, event participation, referrals, and cross-format engagement. But the deeper signal is what happens outside formal programming. Are members hosting their own dinners? Traveling together? Coming in without needing an event as an excuse?

Events are the entry point. The product is what happens after the event. If someone can walk in alone and walk out feeling like they have a place in the city, we’ve done our job.

Landon’s Loop

Learn more about Three Cities Social Chicago

members.threecitiessocial.com/plans/1970331?bundle_token=b8a359a22cc3583495ddd8e2d83cb184