Tips to run a Successful Tricky Tray or Penny Social

Running a successful online Basket Raffle (also known as a Penny Social, Tricky Tray, or Chinese Auction) requires a different strategy than a standard raffle. Because donors need the ability to “distribute” their tickets among specific prizes they want to win, the logistics are more complex.

Here is a step-by-step guide to ensuring your event is a success.

Phase 1: Tricky Tray Sourcing & Curation

1. Secure High-Appeal Items Don’t just look for random gift cards. The success of a basket raffle relies on the “wow” factor of the bundles.

• Theme Your Baskets: Instead of a loose collection of items, create themes like “Date Night,” “Beach Day,” “Gamer’s Paradise,” or “Local Foodie.”
• Mix High & Low Values: Have a few “Grand Prize” baskets (e.g., electronics, vacations) to draw people in, and smaller, fun baskets to ensure more people feel they have a chance to win.

2. Take Professional-Quality Photos In an online environment, the photo is the sales pitch.

• Unwrap for the Photo: Don’t photograph a basket wrapped in cellophane—it causes glare and hides the contents. Arrange the items attractively, take the photo, and then wrap it for the winner.
• List Every Item: In the description, bullet point exactly what is included so donors know the value.

Phase 2:Tricky Tray Technology & Setup

3. Choose the Right Raffle Website Platform This is the most critical step. Most standard raffle platforms (like RallyUp or Zeffy) treat every prize as a separate campaign, which is confusing for donors.

• Requirement: You need a platform that mimics the physical experience: a donor buys a “sheet” of 25 tickets and can digitally “drop” 5 in Basket A, 10 in Basket B, and 10 in Basket C.
• Recommendation: As discussed, Chance2Win is the industry standard for this specific format, handling the complex logic of multi-basket ticket distribution seamlessly.

4. Set Your Ticket Pricing Strategy Encourage higher donations by offering volume discounts (tiering). This is only available on Chance2Win!

The Psychology: Most donors will aim for the middle or high tier to get “more chances” to win the specific baskets they eye.

Phase 3:Tricky TrayLogistics & Rules

5. Define Shipping vs. Pickup Rules Shipping heavy baskets can be prohibitively expensive.

• Be Clear Upfront: State clearly in your rules: “Local Pickup Only” or “Shipping available for Gift Card prizes only.”
• Pickup Event: Turn the pickup into a mini-event (drive-through style) to thank donors in person and take photos for social media.

6. Check Local Compliance Raffles are considered gaming in many jurisdictions.

• Check your state/local laws regarding online raffles.
• Ensure your platform allows you to restrict ticket sales to residents of specific states if required by law.

Phase 4:Tricky TrayMarketing & Execution

7. The “Teaser” Campaign Start marketing 2 weeks before ticket sales open.

• “Basket of the Day”: Highlight one basket on social media every day leading up to the launch. Tag the local businesses that donated the items to expand your reach to their followers.

8. The Live Stream Drawing Don’t just post a list of winners—make it an event!

• Go Live: Use Facebook Live or Zoom to broadcast the drawing.
• The “Spin”: Even if the software picks the winner instantly, read out the names and build suspense.
• Engagement: This is the perfect time to make a final “ask” for general donations or announce your next event.

Phase 5: Post-Event

9. The “Unclaimed Prize” Plan Have a protocol for winners who ghost you.

• Rule: “Prizes must be claimed within 14 days or they will be forfeited/redrawn.”
• Backup Winners: Some platforms allow you to draw a “backup” winner privately in case the first winner is ineligible or unresponsive.

10. Thank Your Sponsors Publicly thank the businesses that donated baskets. Tag them in photos of the happy winners holding their prizes. This ensures they will be willing to donate again next year.