Side Hustle School Ep. 3300 - Q&A: “How many ‘wine-of-the-month’ clubs are there??”
Jan 13, 2026
In this engaging discussion, Yvette, a caller from Long Beach, explores the crowded world of 'of-the-month' clubs. She questions the profitability of these clubs versus subscription boxes. Chris Guillebeau provides insights into market viability, emphasizing the need for specificity in offerings. They dive into the challenges of scaling subscription businesses while managing customer retention. Chris also shares valuable resources, including Cratejoy, to help aspiring entrepreneurs navigate this thriving market.
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Episode notes
Clubs Preceded Modern Subscription Boxes
- Many "of-the-month" clubs are predecessors of today's subscription boxes and share the same dynamics.
- Their persistence implies ongoing demand but also increasing crowding in the market.
Listener Found Every Type Of Club
- Yvette from Long Beach described discovering many clubs including wine, cigars, and pickles.
- She asked whether all these clubs make money and how monthly clubs differ from subscription boxes.
Research Existing Models First
- Do research existing subscription examples in the archives before starting your own club.
- Use best practices from past Side Hustle School episodes to shape your approach.