Podcast – Episode 42: How to Create an "Oprah Moment" at Your Fundraising Auction
In this episode of Auction Is Action with U in It!, Bobby D. Ehlert introduces one of the most powerful and underused strategies in live auction fundraising: the Oprah Moment.
You get a trip. You get a trip. Everybody gets a trip.
Most live auctions end with one winner and a room full of guests who wanted that item but never got the chance. The Oprah Moment changes that entirely, turning a single auction item into multiple sales, multiple winners, and a room full of newly identified mid-level donors worth knowing for years to come.
Key Takeaways
The Oprah Moment Turns One Auction Item Into Multiple Sales
Instead of choosing one winner at the close of bidding, the auctioneer pauses and announces that everyone willing to invest at the final price can win the experience. One trip becomes four trips. One sale becomes $20,000. The room goes from competitive to celebratory in an instant.This Strategy Reveals the Missing Middle of Your Donor Pyramid
Most nonprofits know their major donors and they know their casual event attendees. But the mid-level donors, the guests with real interest and real capacity who have never found the right entry point, are harder to identify. When someone raises their paddle to purchase a vacation for several thousand dollars, they are showing willingness, demonstrating capacity, and revealing that they are comfortable making a significant financial decision in support of your mission. That information is worth far more than the ticket price.The Live Auction Is a Form of Donor Discovery, Not Just Entertainment
The auctioneer must be watching the bidders, not just listening for the final number. Who entered the bidding early? Who stayed engaged as the price climbed? Who hesitated before lowering their paddle? Who looked disappointed when they thought the opportunity was gone? Those signals matter. A skilled fundraising auctioneer reads all of them and uses them to bring multiple buyers into the moment.Travel Experiences Work Because They Sell Anticipation
People can immediately picture themselves on the beach, watching the ocean, sharing a dinner, taking time away with someone they love. You are not selling accommodations. You are selling memories. And when the experience can be sold multiple times without scarcity, you are no longer limited to the revenue of a single bid.The Follow-Up Is Where the Real Fundraising Begins
After the event, do not simply send buyers their travel information and move on. Thank them personally. Ask what attracted them to the experience. Learn more about their connection to the organization. Stay in touch before and after the trip. Ask them to share a photo. The goal is not to immediately ask for more money. The goal is to build the relationship. They raised their paddle because they wanted a vacation. Your stewardship can help them become invested in the mission itself.The Magic Feels Spontaneous But Must Be Carefully Planned
You must confirm in advance that the package can be fulfilled multiple times. Never surprise your vendor or assume additional trips are available. Confirm the inventory, the process, the cost, and any limitations before the event. Many consignment travel vendors offer packages with unlimited capacity and no blackout dates, making the Oprah Moment both feasible and scalable.A Special Offer for New Clients
For every new client who signs up with Call to Auction before the end of 2026, Bobby D. is offering a free live auction item for your event. Reach out at bobby@calltoauction.com or calltoauction.com to learn more.
FULL TRANSCRIPT
Bobby D.:
Today we are talking about the Oprah Moment on this episode of Auction Is Action with You in It podcast. My name is Bobby D, your host, world champion auctioneer, world-traveling fundraising auctioneer, billion-dollar fundraiser, CEO of Call to Auction, co-founder of Inspire Hearts Fundraising and the Gala Toolbox, and chronic fundraiser for over 25 years.
I am here today to chat with you about the Oprah Moment: how one trip can reveal your next major donors.
What if one of the most valuable moments at your fundraising event was not selling one auction item to the highest bidder? What if it was identifying an entire group of guests who are willing, excited, and financially able to invest in your mission? This is what I call the Oprah Moment.
You remember those famous Oprah Winfrey episodes: you get a car, you get a car, everybody gets a car. We might not be able to give everybody in the ballroom a new car, but we can create that same excitement, energy, and sense of shared opportunity during a fundraising auction.
Here is how it works. You feature an incredible travel experience in your live auction. The bidding begins. Hands go up. The room comes alive. Eventually you reach a price where several people are still bidding. So instead of choosing only one winner, the auctioneer pauses and announces: what if I told you that everyone who is willing to invest at this level can win this trip?
Suddenly it is no longer a bidding contest. It becomes an Oprah Moment. You get the trip. You get a trip. You get a trip. One experience is sold multiple times, creating multiple winners and significantly more revenue for the organization. But the real value goes far beyond what is raised that night.
This is the missing middle of the donor pyramid that most nonprofits do not know how to find. You know who your major donors are. You also know the guests who make smaller gifts, purchase raffle tickets, or participate casually during the event. But what about the people in the middle? These are the guests who may have the interest and the financial capacity to become meaningful donors but have never been given quite the right opportunity.
The multi-buyer travel experience helps you identify them.
When someone raises their paddle to purchase a vacation for several thousand dollars, they are telling you something important. They are showing willingness. They are demonstrating capacity. They are revealing that they are comfortable making a significant financial decision in support of your event and your mission. The purchase itself is not entirely a charitable donation since they are receiving a valuable experience in return. But it absolutely identifies someone your organization should get to know better.
That bidder may become a future sponsor. They may increase their annual giving. They may host a table next year. They may introduce you to new supporters. They may eventually become a major donor, a board member, or a campaign leader. This vacation gets their paddle in the air. But the relationship you build afterward can deepen their connection to your mission in ways that compound over time.
Travel experiences are especially effective because they generate an emotional response. People can immediately imagine themselves on the beach. They can picture the ocean view, the dinner, the sunshine, the time away with someone they love. You are not selling accommodations. You are selling anticipation. You are selling memories. You are giving guests permission to enjoy something fabulous while supporting an organization they care about.
And when the experience can be sold multiple times, you are no longer limited to the revenue of a single bid. Imagine one trip sells for $5,000. That is a successful auction item. But what if four guests purchase that same trip for $5,000 each? You have created $20,000 in gross auction revenue and identified four new households with the willingness and capacity to participate at that level. And that is why the auction should never be viewed as entertainment alone. It is a form of donor discovery.
Now, creating this moment in the room requires intentionality. The auctioneer must be watching the bidders, not merely listening for the final number. Who entered the bidding early? Who stayed engaged as the price increased? Who hesitated before lowering their paddle? Who looked disappointed when they thought the opportunity was gone? Those signals matter.
Once we know there are several qualified bidders, we slow the moment down and bring them back into the conversation. I might say: ladies and gentlemen, we have some exciting news tonight. We do not only have to choose one winner. If you were prepared to invest $5,000 in this experience, keep your paddle in the air. We have the opportunity to send every one of you on this fabulous vacation while generating even more support for this mission.
And then we recognize each buyer individually. Paddle 214 is going. Paddle 118 is going. Paddle 237 is going. The recognition is so important. Each buyer should feel celebrated, not processed. This is the moment they get to feel great about the experience they purchased and the organization they supported.
But there is one important rule: you must know in advance that the package can be fulfilled multiple times. Never surprise your provider or assume additional trips are available. Confirm the inventory, the process, the cost, and any limitations before the event. We work with many vendors that have access to trips with unlimited capacity and no blackout dates. The magic may feel spontaneous to the audience, but it must be carefully planned behind the scenes.
Now, we have an exciting opportunity: a new trip available for nonprofit fundraising events. This is a five-day, four-night all-inclusive escape for two at Costas Resort in Puerto Vallarta, Mexico. Guests stay in a deluxe oceanfront studio with a private balcony and spectacular views of the Pacific Ocean. The package includes dining and beverages throughout the stay with access to the resort's restaurants and ocean view bars, roundtrip transfers between the airport and hotel, a 60-minute couple's massage, an in-room welcome amenity, and the Costas Resort beach bag filled with getaway goodies.
This is the kind of experience guests can instantly picture themselves enjoying: ocean views, warm sunshine, all-inclusive dining, a couple's massage, and relaxation just minutes from downtown Puerto Vallarta. And most importantly, this package gives us the opportunity to create that multi-buyer Oprah Moment at your event. Instead of sending only one couple to paradise, we can engage several: 10, 12, 15. We have even sold up to 57 of these trips at a single event.
The follow-up is where the real fundraising begins.
After the event, do not simply send the buyers their travel information and move on. Thank them personally. Ask what attracted them to the experience. Learn more about their connection to the organization. Stay in touch before and after the trip. You could even ask them to share a photograph from Puerto Vallarta and tell you about their favorite part of the experience.
The goal is not to immediately ask them for more money. The goal is to build the relationship. They first raised their paddle because they wanted a vacation. Your stewardship can help them become even more invested in the mission. And that is how a live auction buyer becomes a long-term supporter.
Now, I have a special offer. If you are planning a fundraising event and want to explore how the Oprah Moment could work in your ballroom, we would love to help. For every new client who signs up with Call to Auction before the end of 2026, we are offering a free live auction item for your event. That is right: this trip to Puerto Vallarta can be yours at no cost. That means you can bring in an experienced fundraising auctioneer, strengthen your overall fundraising strategy, and add an exciting auction opportunity without having to source the item yourself.
The right auction item does far more than fill a spot in your program. It creates energy, inspires participation, generates revenue, and helps reveal the donors who might be ready for a deeper relationship with your organization.
So the next time you are planning your live auction, do not only ask how much can we sell this trip for. Ask how many people can we engage through this experience and what could those relationships become? Because sometimes the greatest value of an auction item is not the money it raises. It is the people who raise their paddles.
Friends, if you are interested in this opportunity, please reach out at bobby@calltoauction.com, visit calltoauction.com, or find me on Instagram at Bobby Auctioneer or Call to Auction. I would love to chat with you about how we can use this as the Oprah Moment at your event.
Thank you all so much for being open to this opportunity to engage more mid-level donors at your fundraising event. Thank you for all the work you do, the impact you create, and the missions you are fulfilling by wanting to create better and more lucrative fundraising events. My name is Bobby D with Call to Auction. And remember: auction is action with you in it.
Ready to Raise More?
At Call to Auction, we specialize in turning galas and fundraising events into mission-driven, revenue-generating experiences. From paddle raises to live auctions, our team knows how to excite donors, engage audiences, and inspire generosity in the moment.