Cocktails with Courtney: October Through the Years, 1998–2026
From New York to Paris, and back to Tucson: a look through the October archives.
Last night, October 28, Cocktails with Courtney gathered at The Broadway Wine Bar in Tucson, Arizona, for another evening of conversations, connections, and catching up.
I’d been meaning to share a series of throwback posts throughout October, revisiting past Cocktails with Courtney events on their anniversaries. If you’ve seen any of my prior posts online, you’ll understand how the month got away from me.
Looking through my old Cyber Scene articles and CWC photo galleries, I realized just how much ground we covered during Octobers past.
Between 1998 and 2011, I found 15 October gatherings in eight cities: New York, San Francisco, Philadelphia, Chicago, Pittsburgh, Los Angeles, London, and Paris.
And in October 2000 alone, we held six events in six cities in just two weeks. Managing that kind of schedule was easier as a 20-something!
So, instead of individual anniversary posts, here’s one big trip down memory lane.
1998: New York City
October 28 — New York City
Twenty-eight years ago, Cocktails with Courtney was already bringing people together in New York. The photographs from this October gathering offer a glimpse of those early networking days, long before LinkedIn, Facebook, or today’s social media platforms.
View the October 1998 New York photo gallery
1999: New York, San Francisco, and Philadelphia
October 6 — Gaslight Lounge, New York City
The month opened with a gathering at the Gaslight Lounge. My Cyber Scene writeup, published the following day, was titled Guten Tag!
Read Guten Tag! | View the photos
October 12 — Bill Ryan’s Home, San Francisco
A few days later, CWC headed west for an evening at Bill Ryan’s home. The original article was fittingly titled Classic Cocktails.
Read Classic Cocktails | View the photos
October 13 — The Plough and the Stars, Philadelphia
The following evening brought another gathering, this time in Philadelphia. My writeup, From the Hills to the (other) Valley, captured another stop in the growing CWC network.
Read From the Hills to the (other) Valley
October 27 — Obeca Li, New York City
We returned to New York for a Cocktails with Courtney gathering and book signing celebrating NetSlaves. Publishing, technology, and the people building the early Internet made for a natural combination.
Read Cocktails and Book Signing | View the photos
2000: Six Cities in Two Weeks
October 2000 deserves a chapter of its own. Looking at the schedule today, I have to wonder when I found time to unpack my suitcase.
October 12 — Kaberet, London
We began in London, at Kaberet near Beak Street. The resulting Cyber Scene story was titled Lush-Scene In London.
Read Lush-Scene In London | View the photos
October 17 — Harry’s Velvet Room, Chicago
Five days later, we were in Chicago for another evening of introductions and conversation.
Read Martinis in the Windy City | View the photos
October 22 — The Mattress Factory, Pittsburgh
Next came Pittsburgh, where Cocktails with Courtney took place at The Mattress Factory. An art museum made an especially interesting setting for a gathering of people involved in technology and business.
Read Steeltown’s New Calling: Pittsburgh | View the photos
October 23 — Loews Philadelphia Hotel, Philadelphia
The very next evening, we were in Philadelphia, at the historic PSFS building, for a gathering in the hotel’s Commonwealth ballroom.
Read The City That Loves You Back Parties | View the photos
October 24 — Lounge 217, Santa Monica
Then it was off to Southern California. The original article documented a gathering at Lounge 217, bringing another part of the Internet community into the CWC orbit.
Read Style, Attitude and Glamour
October 26 — British Motor Cars, San Francisco
We finished this extraordinary stretch in San Francisco, at the British Motor Cars showroom on Van Ness Avenue.
Read San Franciscans Party Through the Night
Six cities, six events, fifteen days. That was quite an October.
2001: New York City
October 23 — New York City
The October 2001 gathering took place just weeks after September 11, during an extraordinarily difficult period for New York.
The original announcement identified Microsoft as a sponsor, and the photographs remain in the CWC archive. Although I haven’t recovered the original post-event writeup, the photo collection preserves a record of the gathering.
View the October 2001 New York photos
2002: New York City
October 16 — Flute, 20th Street
Cocktails with Courtney returned to New York for an October gathering at Flute. The event was documented in The Cyber Scene, where so many of these gatherings originally appeared.
Read Cocktails with Courtney — October
2006: A Halloween Gathering in New York
October 31 — Pulse Restaurant, New York City
Not all CWC evenings followed the traditional cocktail-party format. In 2006, we celebrated Halloween with a Groucho Marx-themed gathering at Pulse Restaurant.
Read Cocktails with Courtney Halloween | View the Halloween photos
2011: Paris
October 26 — Tuileries Bar, Paris
By 2011, Cocktails with Courtney had made its way to Paris. The October gathering at Tuileries Bar added another international chapter to the story.
Read Cocktails with Courtney — October 26
A lot has changed since those early Internet days. Companies have come and gone, entire industries have evolved, and the ways we communicate have changed beyond anything we could have imagined in 1998.
But one thing hasn’t changed: the pleasure of meeting interesting people, hearing their stories, making introductions, and seeing where those connections lead.
That’s what Cocktails with Courtney was always about.
Looking back through these articles and photographs, I’m reminded not just of the places we visited, but of the extraordinary number of people who crossed paths along the way.
If you attended any of these gatherings, I’d love to hear from you. What do you remember? And if you recognize yourself or someone you know in the photographs, please say hello.
Here’s to old connections, new friendships, and keeping the conversations going.