How to Create an “Oprah Moment” at Your Fundraising Auction

What if one travel package could produce multiple winners, multiply your auction revenue, and help identify your organization’s next major donors?

In this episode, Bobby D. explains how to create an “Oprah Moment” at your fundraising auction by selling the same exciting travel experience multiple times. This strategy engages midlevel donors, reveals willingness and financial capacity, and creates opportunities for deeper relationships after the event.

You’ll also learn about an exclusive five-day, four-night, all-inclusive Puerto Vallarta experience for two at Costa Sur Resort, featuring oceanfront accommodations, dining and beverages, airport transfers, a couples massage, and more.

Plus, every new Call To Auction client who signs before the end of 2026 will receive a free live-auction item for their event.

Ready to create your own “Oprah Moment”? Connect with Call To Auction to learn more.

Auction is action—with “U” in it.  

calltoauction.com

Recommended For

Nonprofit leaders
Development directors
Board members
Event planners
Fundraising committees
School, hospital, and foundation galas

Transcript

SPEAKER_00 0:00

Alright here, 250 minutes. You are listening to the Auction Is Action with You and a podcast presented by Call to Auction, where our favorite four-little word is S-O-L-D. So, so so You're going to Mexico, you're going to Mexico, you're going to Mexico. Today we're talking about the Oprah moment on this episode of Auction is Action with You and a podcast. My name is Bobby D, your host and world champion auctioneer, a world traveling fundraising auctioneer, billion-dollar fundraiser, CEO of Call to Auction, uh, co-founder of Inspire Hearts Fundraising, and the Gallup Toolbox and Chronic Fundraiser for over 25 years. And I am here today to chat with you about the Oprah moment, how one trip can reveal your next major donors. Now, what if one of the most valuable moments at your fundraising event wasn't selling one auction item to the highest bidder? What if I it was identifying an entire group of guests that are willing, excited, and financially able to invest in your mission? This is what I call the Oprah moment. Now, you remember those old, those famous uh Oprah Winfrey episodes where it's you get a car, you get a car, everybody gets a car. Now, 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's 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 bidding. So instead of choosing only one winner, the auctioneer pauses and announces, what if I told you that everyone who's willing to invest at this level can win this trip? Now, suddenly it's no longer a bidding contest, it becomes an Oprah moment. You get the trip, you get a trip, you get a trip. Now, 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. Now, this is the middle of the missing middle of the donor pyramid that most uh nonprofits who know they don't know who their major donors are. You also know the guests who make smaller gifts, purchase raffle tickets, or participating casually during the event. But what about those people in the middle? These are the guests that may have the interest and financial capacity to become meaningful donors, but you've yet to give in at the right opportunity. Now, the multi-sale travel experience helps us to identify them. Now, when someone raises their paddle to purchase a vacation for several thousands of dollars, they're telling you something important. They are showing willingness, they're demonstrating capacity, and they're revealing the that they are comfortable making a significant financial decision in support of your event and your mission. Now, that does not automatic automatically make them entire the entire purchase charitable donation, of course, but they are receiving a valuable experience in return. But it does identify someone your organization should get to know better. Now, that batter, that bidder, that better bidder, 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. Now, this vacation gets their paddle in the air, but the relationship you build afterward can deepen their connection to your mission. Now, 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, and the time away with someone that they love. You're not just simply selling accommodations, you're selling anticipation, you were selling memories, you were giving guests permission to enjoy something fabulous while supporting an organization that they care about. And when the experience can be sold multiple times, you are no longer limited to the revenue of a single bid. Now imagine that one trip sells for $5,000. That is a successful auction item. But what if four guests get to purchase that same trip for $5,000 each? You've created $20,000 in gross auction revenue and identified four new households with the willingness and capacity to participate at that level. And that's why the auction should never be viewed as entertainment alone. It's a form of donor discovery. Now, this is creating the moment in the room. This strategy needs to be intentional. 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 that there are several qualified bidders, we can slow the moment down and bring them back into the conversation. Now I might say, ladies and gentlemen, we have some exciting news tonight. Tonight, we do not have the 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 individual. Paddle 214 is going, paddle 118 is going, paddle two uh two three seven is going. Now the recognition is so important. Each buyer should feel celebrated, not processed. This is the moment that they get to feel great about the experience that they purchased and the organization that they supported. But there's 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. Now you have to confirm the inventory, the process, the cost, and any limitations before the event. We work with many different vendors that have access to these different trips, and many of these trips have unlimited capacity and they don't have any blackout dates. It's amazing the way that this works. Now, the magic may feel spontaneous to the audience, but it becomes 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, that's right, I said all-inclusive, escape for two at Costa Sur Resort in Porta Varta, Mexico. Now, guests are going to be staying in a deluxe ocean front studio with a private balcony, a spectacular view of the Pacific Ocean. Now, this package includes dining and beverages throughout the stay, with access to the resort's uh restaurants and ocean view bars. It also includes round trip transfers between the airport and a hotel, a 60-minute couples massage, and an in-room welcome amenity and the Coast de Sur beach bag filled with getaway goodies. Now, this is the kind of experience that guests can instantly picture themselves enjoying. Ocean views, warm sunshine, and all-inclusive dining, a couples massage, four nights relaxation just minutes from downtown Puerto Vallarta. Now, most importantly, this package gives us an opportunity to create that multi-buyer Oprah moment at your event. So instead of only sending only one couple to Paradise, we may be able to engage several, 10, 12, 15. We've even sold up to 57 of these trips at an event. This is an opportunity to generate multiple sales and help your organization discover new med-level donors. Now 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 them what attracted them 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 Porto Virta 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 that relationship. They first raised their paddle because they wanted a vacation. Your stewardship can help them to become even more invested in the mission. And that's how a live auction buyer becomes a long-term supporter. Now I've got a special offer. If you're planning a fundraising event and want to explore how the Oprah moment could work in your ballroom, we would love to help. Now, for every new client who signs up with call to auction before the end of 2026, we're offering a free live auction item for your event. That's right, this trip to Port of ARC can be yours for free. And that means that you can bring in an experienced fundraising auctioneer, strengthen your overall fundraising strategy, and add an exciting auction opportunity without having to source every item yourself. This, the right auction item, does not uh does way more than fill a spot in your program. It creates energy, inspires participation, it generates revenue, and it helps to reveal the donors that might be ready for a deeper relationship with your organization. So the next time you're planning your live auction, do not ask only 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 simply the money it raises, it is the people who raise their paddles. So, friends, if you're interested in this opportunity, please reach out Bobby at calltoauction.com, go to calltoauction.com, fill out the uh the form there, uh, or reach out on Instagram at Bobby DAUctioneer or at call to auction. And I'd love to chat with you of how we could use this particular item as the Oprah moment at your event. So I want to thank you all so much for being interested in this and being open to the opportunity to engage more mid-level donors at your fundraising event. Thank you for all the work that you do, the impact that you create in the world, and the missions that you are fulfilling by wanting to create better and more lucrative fundraising events. Again, my name is Bobby D with Call to Auction. And remember, auction is action with you in it. And $25,000, $d, $30,000, $dow, $30, now $35,000. Who gets $40,000? What'd you go? And a bit to give $40,000, $40,000 now, $45,050. I'm gonna bid $50, $50, $55, $55, and a bit $60 now, $55, and a bit 70, $70, $75, and a bit, and it's SOLD. Sold, sold, sold. You got it right there.