Overview

City Companion is a creator‑led series designed to show how Copilot can deepen your connection to the place you live, whether you’re a lifelong local or a first‑time visitor. We partnered with well‑known creators in Chicago, New Orleans, and Boston to take viewers on walking tours that blend personal stories, local knowledge, and spontaneous discovery. With the Microsoft Copilot app, each city becomes a scavenger hunt waiting to be uncovered.

The Story

Every city holds layers of history, culture, and personal meaning that most people walk past without noticing. City Companion invites viewers to slow down and look closer.

In Chicago, Liv Pearsall uncovers the mysteries behind the historic Water Tower, traces the filming locations of beloved TV shows, and wades into the deep‑dish vs. tavern‑style pizza debate. In New Orleans, Ma’ya Jackson explores haunted architecture, tastes local staples, and follows the pulse of live jazz through the French Quarter. In Boston, Ted Nivison revisits childhood memories with his father, dives into local food culture, and reconnects with the city’s history, from Fenway Park to the Freedom Trail.

Across all three cities, the through‑line is curiosity and ease of use: see something interesting, snap a picture, and Copilot reveals the story behind it.

Approach

We captured each creator’s journey with an edutainment-meets-documentary lens. The creators lead with their own voice and personality, while Copilot acts as a real‑time companion that unlocks context, history, and hidden details. The tone is casual, human, and exploratory, just creators moving through their cities, following their instincts, and letting Copilot deepen the experience.

Output

Three creator‑led city films for Microsoft Youtube — Chicago, New Orleans, and Boston — supported by social cutdowns that appeared on creator’s channels.

Role

Director

Team + Agency

Josh Charow - DP
Henry Kornaros - Editor
Caroline Goguen - Producer
John Tringl - Account
Superdigital