Yep, that’s our name and logo on the Citi Field Jumbotron!

Every December, a small group of 7- and 8-figure founders in DC BLACK come together in New York City to step out of execution mode and into something rarer: clarity.

This is an intentionally small, invite-only gathering for operators who already have momentum, and want to design businesses and lives that still work 5, 10, 15 years from now.

This year, ~25 founders spent three days together doing exactly that.

Why New York City?

NYC has density, energy, and creative pressure. It’s a city where ideas collide, and where ambition is normal.

For DC BLACK, it’s also the ideal backdrop for annual planning: reflecting on what worked, pressure-testing what didn’t, and setting a clear direction for the year ahead.

Around the holidays, it adds just enough magic to remind everyone why we started building in the first place.

What We Actually Did (Beyond the Highlights Reel)

Across three days, DC BLACK members moved between structured work and unstructured connection (because both matter.)

We spent time:

Connecting deeply over shared breakfasts, curated lunches, and long dinners across NYC
Exploring the city together through private, behind-the-scenes experiences, including a party-bus ride and on-field batting practice at Citi Field
Going deep in facilitated masterminds, tackling real constraints around growth, leadership, acquisitions, and personal tradeoffs
Sharing wins, failures, and future plans through Show & Tells, peer feedback, and live Q&As
Letting the pressure off with cooking competitions, friendly rivalry, and late-night karaoke
Pressure-testing 2026 plans with peers who have the context and numbers to give meaningful feedback

The format is deliberate: enough structure to arrive prepared, enough freedom for the best conversations to happen organically.

Learning From People Who’ve Built at Scale

Two special guests joined the group, simply because they heard what we’re about and wanted to participate.

Scott Heiferman, founder of Meetup.com, joined for a candid conversation on community, leadership, and the difference between a career and a calling
Keith Murray, frontman of We Are Scientists, shared lessons from nearly three decades of building a creative business that still works

Both guests came because they wanted to be in the room. Because the businesses, lives, and questions being discussed were genuinely interesting. That’s a recurring pattern at DC BLACK events.

The Real Takeaways That Kept Coming Up

While every founder arrived with a different business, a few themes surfaced repeatedly:

Business design matters more than growth rate
Many founders in the room had peers with larger companies, but less freedom. Design intent beats brute force.
Leadership is clarity, not charisma
Clear purpose, clear end states, and clear decision rights outperform heroics every time.
AI is changing workflows, not vision
The best operators are aggressively automating execution while doubling down on human judgment and architecture.
Friendly acquisitions are accelerating
More founders are buying and selling businesses through trust-based, relationship-driven deals, not traditional PE processes.
Plans beat goals
Every serious 2026 conversation backed into numbers, constraints, and execution paths.

Why the Group Size Matters

Several attendees said the same thing in different words:

“The group size was perfect. I was able to spend time with each person, and that’s rare.”

DC BLACK intentionally caps attendance. Not for exclusivity theater, but because trust, nuance, and real feedback don’t scale infinitely.

When founders can show real numbers, talk openly about personal tradeoffs, and ask for help without posturing, the quality of insight changes completely.