The real cost of small Ruby conference organizing: Success stories and financial risks

Friendly Show

In this special crossover episode, hosts from The Friendly Show, Indie Rails, and Code with Jason come together to share the unvarnished truth about organizing Ruby conferences.

Adrian (Friendly RB), Jeremy (Blue Ridge Ruby), and Jason (Sin City Ruby) open up about their journeys from conference attendees to organizers, revealing the financial realities, emotional highs and lows, and unexpected challenges of creating memorable experiences for the Ruby community.

What You'll Learn:

• How much it really costs to start a conference (spoiler: more than you think)
• Why hotel blocks can financially destroy small conference organizers
• The 250+ hours of work that goes into organizing a single event
• How COVID changed the conference landscape and created opportunities
• Why some conferences intentionally don't record videos
• The difference between building sustainable events vs. one-time experiences
• Real stories of both financial losses and life-changing community connections

Key Topics Covered:

• Conference economics and budgeting strategies
• Venue selection and negotiation pitfalls
• Marketing and ticket sales challenges
• The psychology of conference organizing addiction
• Alternative event formats (like Jeremy's "Ruby on Trails" backpacking trip)
• Sponsorship vs. ticket revenue strategies
• When to stop and why trilogy endings matter

Whether you're considering organizing your first conference, curious about the business side of community events, or just want to understand what goes into creating those magical conference experiences, this conversation pulls back the curtain on the real work behind Ruby's regional conference scene.

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