In this episode, Michael Dorf, visionary music venue founder and operator, shares with music lawyers Bill Hochberg and Elliot Resnik some unforgettable tragi-comic stories about scary risks, near-disasters, and soaring successes with his City Winery clubs and the Knitting Factory venues that he founded and has operated for years. From mobbed-up Houston Street in the 1980s to City Winery’s five-star wine-and-dine-and-music experience on Manhattan's Pier 57, this conversation pulls back the curtain on what it actually takes to build and scale a live venue brand without losing its soul. Ultimately, this is a conversation about entrepreneurship, hospitality, and the irreplaceable charge of being in the room when something unforgettable happens, like when Prince, Lou Reed, John Zorn and many others blew the roof off of the place ... fun stuff.
00:00 Introduction
01:28 The City Winery Model: Music, Wine, Food & Community
06:39 Designing a Venue People Can Feel
10:50 How Technology Changed the Music Industry
22:36 Building City Winery Through Recession, COVID & Expansion
27:11 How COVID Changed Live Music Venues
49:48 The Broken System Behind Live-Music Royalties
1:03:11 Can Independent Venues Compete and Survive?
1:07:04 Michael Dorf’s Legacy: Equity in Live Music
You’ll hear:
How a tiny avant‑garde room became ground zero for downtown music
Why sound, sightlines, wine glasses, bathrooms, and old brick walls all matter to the bottom line
Why Michael is more passionate about fixing PRO royalties than selling “a f*ckload of wine and tickets”
Ultimately, this is a conversation about entrepreneurship, hospitality, and the irreplaceable charge of being in the room when something unforgettable happens and why there’s still “no app for that.”
In This Episode:
The Knitting Factory years
How Michael signed a lease on Houston Street in 1986 and turned a scrappy, avant‑garde club into a cultural hub for artists like John Zorn, Sonic Youth, Ornette Coleman, Philip Glass, and Brian Eno.
Inventing City Winery
The moment a barrel of wine in California, a need for better food and seating, and a two‑hour “all-in” night out fused into the concept for City Winery—part concert venue, part working winery, part restaurant, part private‑event space.
Designing for the senses
Why Michael obsessed over real wood, reclaimed beams, barrel staves, acoustics, lighting, and even bathrooms to create a hedonistic, intimate experience where 300 people can all feel connected to the artist.
The Prince & Beyoncé story
Inside the legendary Purple Week at City Winery: Prince circling the venue at 3 a.m., playing until nearly 6 a.m. on some nights—and blowing off a night where Beyoncé was waiting in the back room for a show that never happened.
Why 300 seats is a magic number
The capacity where an artist can see every face in the room, why that intimacy matters, and how it differentiates City Winery from arenas and stadiums.
Surviving crises and shifting habits
How City Winery navigated the 2008 financial crisis, the COVID shutdowns, artist cancellations, changing work patterns, and the competition from “stay on the couch” entertainment.
The brutal economics of small and mid‑size venues
Thin margins, rising real estate, fickle demand, and why independent venues struggle even as stadium tours thrive—and how Michael thinks about value, pricing, and experience in that environment.
Scaling without losing the soul
What it took to expand City Winery to cities like Chicago, Nashville, Atlanta, Boston, and Philadelphia, while preserving intimacy, authenticity, and artist trust.
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Bill Hochberg is a music and media lawyer at Raines Feldman Littrell LLP and he writes regularly in Forbes and other top publications on the business and law of music.
Our musical theme is "8 Church Birds" by billeeto. https://tinyurl.com/billeeto
DISCLAIMER: This program and the associated written materials are provided for informational purposes only and are not intended, and must not be taken, as legal advice on any particular set of facts or circumstances.
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