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April 17, 2025 20 mins

Paul Chambers is the Co-Founder of SubSummit, the world’s largest conference dedicated to subscription, membership, and recurring revenue models in the direct-to-consumer space. With over 20 years of experience in subscription commerce, including launching Gentleman's Box in the early 2000s, Paul brings a rare blend of operator insight and community-building expertise to the challenges of scaling retention-first brands.

Driven by the belief that subscriptions are more than a billing model, Paul helped transform SubSummit from a small founder meetup into a global ecosystem, connecting thousands of brands each year. The event fuses tactical content with curated networking and is designed to help ecommerce teams grow beyond one-off purchases and into long-lasting customer relationships.

Each year, Paul and his lean team develop a thematic roadmap for the event, guiding DTC operators through the shifting landscape of loyalty, retention, and membership. From Walmart+ to Amazon Prime to True Classic’s hybrid models, Paul studies the movements of top brands and distills them into actionable lessons for growing recurring revenue.

In This Conversation We Discuss: 

  • [00:42] Intro
  • [00:54] Navigating business partner dynamics
  • [02:31] Connecting DTC brands through events
  • [03:08] Starting with a founder-first vision
  • [04:30] Learning big lessons from small niches
  • [06:05] Rebranding to reflect the vision
  • [06:59] Investing upfront in long-term value
  • [10:15] Improving how people connect
  • [12:42] Balancing virtual and in-person events
  • [14:17] Designing curated table conversations
  • [15:48] Making events affordable for founders

Resources:

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