110 | How Intimidating Menus Keep Cocktail Culture Niche (Insights from Hunter Gregory from Maybe Sammy, Sidney)

Merry Christmas & Happy 2026. This Episode is hosted by Chris Maffeo and brought to you by MAFFEO DRINKS. 

In this episode of MAFFEO DRINKS, host Chris Maffeo speaks with Hunter Gregory, Bar Manager at Maybe Sammy in Sydney, Australia, about scaling cocktail culture beyond the usual suspects and making premium cocktails accessible to everyday drinkers.

The conversation explores Sydney's cocktail scene positioned "10 years behind London" despite having quality bars that rival global standards, but revealing how average consumers struggle with understanding enhanced cocktail experiences just like other cities.

Hunter shares the origin story of Maybe Sammy's transformation from a serious hotel-style bar to an energetic showmanship destination when founder Stefano Catino bought a bubble gun from Kmart and decided "f**k it, let's have some fun."

We examine the strategic use of mini martinis during happy hour as a trust-building gateway that gradually brings guests on a cocktail journey from classics to experimental drinks like milk-washed Negroni, Americano with Vegemite macadamia milk.

The discussion covers how Asian cocktail trends increasingly influence Australian bars as European bartenders migrate eastward, the philosophy of "your guests are not always right, but they're always your guests," and why the shift from serving gin and tonics at 10pm to serving complex cocktails throughout the night represents six years of earned trust.

Hunter provides insights on breaking down intimidating cocktail menus, managing consumer expectations around "serious" bar environments, and understanding that people seek experiences that make them feel better rather than just drinks.

Timestamps:

• 00:00 Introduction: Scaling Cocktail Culture to Wider Audiences
• 02:15 Sydney Cocktail Scene: 10 Years Behind London
• 06:30 Australian Drinking Culture: Amazing Bars vs Everyday Pubs
• 09:45 The Demographic Challenge: Experience vs Getting Drunk
• 13:20 Asian Influence on Australian Cocktail Trends
• 17:40 Maybe Sammy Origin Story: From Stuffy to Fun
• 21:25 The Bubble Gun Moment: Breaking Hotel Bar Barriers
• 24:50 Show Business Philosophy: Serious About Craft, Not Ourselves
• 28:10 Mini Martini Strategy: Building Trust Through Happy Hour
• 32:15 Guest Journey: From Classics to Experimental Over Six Years
• 35:40 Wrap up: Making Cocktail Culture Accessible and Fun

This episode is brought to you by MAFFEO DRINKS, an Advisory helping drinks leaders execute bottom-up growth while managing stakeholder expectations. You can get in touch at bottomup@maffeodrinks.com

A Deep-Dive Analysis of This Episode is Available at maffeodrinks.com