Challenge:
Boost brand awareness of City Winery Chicago through live music. Easy enough, until the artist is Prince, it's a Saturday afternoon, and you're driving on the Eisenhower.
What I Did:
Prince had just performed at George Lucas and Mellody Hobson's wedding at Promontory Point. For his aftershow, he chose City Winery Chicago.
The call came in on a Saturday afternoon while I was driving to the suburbs to meet friends. I exited, got to my friend's house, and borrowed her computer, because this was before working from home was a thing and I had no other option.
From her living room, I coordinated a three-way operation. Our designer was at a wedding in Ohio, and she walked me through uploading the photos remotely. Our tech guy was in New York, and I got him on the phone to make sure our server could handle the surge. Before we could announce publicly, we had to email investors and members first.
Then we launched.
My phone exploded. Friends texting, calling, asking: is this real?
I only had time to reply: YES!!!
All 400 tickets sold in 33 minutes.
CBS reported on the concert the following morning, quoting content I had written on City Winery Chicago's social channels that same afternoon.
The Result:
A sold-out Prince aftershow, earned media coverage, and a story I will never stop telling. Sometimes the best marketing isn't planned. It's how fast and how well you execute when the moment arrives.
What This Means For My Clients:
Strategy matters enormously. So does the ability to move fast, stay calm under pressure, and execute when the window is impossibly small. From my friend's living room in the suburbs, coordinating across two time zones with borrowed equipment, that's the kind of grace under chaos no job description prepares you for. It's a skill I bring to every client engagement, whether we're planning six months out or pivoting on the fly.
