The Easiest $10K You Can Add to Your Next Fundraising Event

A New Revenue Enhancer, Tried for the First Time

Brittany Pilcher runs Wine Quest, the signature fundraising event for Questing, an Orlando-based nonprofit serving people with developmental disabilities across Central Florida and Tampa. Wine Quest is a two-night event that puts roughly 750 guests in a ballroom for fine wine and spirits, and it already had a mature revenue mix — a wine toss, a wine pull, silent auctions both nights, and a live auction. What it didn't have, until this year, was a way for guests to participate meaningfully at a lower dollar amount without diluting the night's bigger asks. That's where the golden ticket came in — a raffle-style drawing for a trip package, sold in a limited quantity at a fixed price, run entirely before the event's main program.

Pilcher admits she was hesitant to try it. "As a fundraiser, you're always looking at your bottom line. You're wanting to net as much as you can," she said. "There's a slight expense to it, and you're like, we've got to make sure we cover this expense." Questing didn't secure a sponsor to underwrite the ticket's cost, which added to her caution going in. But once she committed to testing it, the results reframed the entire calculation.

Sold Out in 72 Hours

Questing put its golden ticket on sale exactly three days before Wine Quest's opening night, listed directly on their existing auction platform. The offer let buyers purchase a ticket without needing to attend the event at all — the winner would be drawn during the gala, but presence wasn't required to win. That single detail mattered more than Pilcher initially expected. "We had a lot of pre-sales. So going into it, I knew we were covered," she said. All 100 tickets, priced at $100 each, sold out within 72 hours — before the first night of the event had even started. "I'm like, we need more tickets. But of course, that's the draw of it."

Asked whether she'd extend the sale window if she ran it again, Pilcher's answer wasn't simply "sell longer." She'd consider running two golden tickets simultaneously at different price points — say $100 and $250 — rather than just expanding the pool of a single offer. Her reasoning centers on the psychology of scarcity: "I think there's such an appeal to be like, my chance is one in 100. If you had maybe two of them going at two different price points, but the smaller amount of tickets, you're just like — more skin in the game." For an organization trying this for the first time, though, her practical advice is simpler: open the sale two weeks out rather than three days. "That's not going to hurt," she said.

Mini takeaway: Letting guests buy without needing to attend meant pre-sales rolled in immediately — Questing knew the golden ticket was covered before the event even opened its doors.

Why a $100 Raffle Reaches Donors a Bid Paddle Never Will

Wine Quest raises close to half a million dollars a year and leans heavily on corporate sponsorships, which means a large share of the room arrives on a sponsor's ticket rather than through a direct relationship with Questing's mission. Pilcher sees the golden ticket as a way to reach exactly those guests. "You have a lot of individuals that are coming on that sponsor ticket, and they don't necessarily have that connection to your mission," she said. "It's that psychology of, okay, if I am going to make a donation, because maybe my heartstrings aren't being pulled with the bid-from-the-heart yet, but I will give $100 for the chance to win a fabulous trip."

The prize itself mattered too, and Questing leaned into variety rather than a single destination. Winners could choose between an all-inclusive trip to Cabo, a Kentucky Bourbon Trail experience, a Tuscany package with wine delivered to their door, or three nights in Sedona. "That was such a fun variety that it really spoke to a lot of people," Pilcher said. "It was a wide enough range to appeal to a big demographic." A guest who has zero interest in a beach vacation might still jump at bourbon country or an Italian wine trip — offering choice widened the pool of people willing to buy in.

Timing the Announcement for Maximum Emotional Payoff

Questing's team spent real deliberation on exactly when to announce the winner during the program. The core concern was straightforward: don't let anticipation for the golden ticket drawing compete with, or dampen, the live auction and the bid-from-the-heart appeal that followed it. Their solution was to announce the golden ticket winner immediately before the live auction began. "We don't want anybody that might want to bid on a live auction item, or just write that extra donation to Quest, to hold back because they're waiting to see if they won the golden ticket," Pilcher explained. By resolving the raffle first, guests could fully engage with the rest of the night's asks without a lingering distraction. As it happened, the winner was a longtime event attendee and supporter who was seated in the room — a genuinely well-received moment that Pilcher described as "a great moment."

Mini takeaway: Announce the golden ticket winner before your live auction or fund-a-need — not during or after — so anticipation doesn't compete with your night's biggest asks.

The Lightest Lift With the Biggest Upside

Asked whether she'd found any other revenue enhancer with a comparably favorable ratio of effort to return, Pilcher didn't hesitate. "That's why I like the golden ticket — because of the limited amount of resources it took from the team, it was very easy." She credited HGA's Zach Nelson specifically for making the execution nearly turnkey: ready-made photos and descriptions, proactive but not pushy strategy suggestions, and hands-on review of Questing's signage and social posts before they went live. "It was so plug and play," she said. "You just kind of sit back and keep looking at the ticker on how many tickets have sold."

The internal rollout mattered just as much as the external marketing. Because this was a new offering, Pilcher brought it to her event committee roughly three weeks before Wine Quest — not to ask permission, since she'd already decided to move forward, but to get genuine buy-in and make sure committee members understood the mechanics well enough to speak about it confidently. That paid off directly: committee members shared the ticket sale on their own social channels and mentioned it to their table guests, and some sent links to contacts outside Orlando entirely. "They were sending links to people that weren't even in Orlando, Florida, where we are, like, hey, support Quest — I'm involved in this," Pilcher said.

The Real Return Isn't Just the $10,000

Questing's golden ticket brought in $10,000 in gross ticket sales — money Pilcher hadn't originally budgeted for — but she's careful to point out that the number understates the real value. "It's not just, okay, we netted [what] we weren't expecting, like that was great, but the return on the investment for me is we've had guests have a great guest experience at our event." More importantly, the raffle produced a fresh list of roughly 100 individuals who'd made a direct financial connection to the mission — some already known to Questing's database, but a meaningful chunk who were new. That list becomes fertile ground for stewardship: a tour invitation, a targeted follow-up based on what kind of trip they were drawn to, or a next step toward deeper involvement. "It gives us a little bit of information on what they're interested in, and then we can follow up on the next steps to see if they want to get further involved with Quest," Pilcher said.

For an organization considering a golden ticket for the first time, Pilcher's experience offers a clear, low-risk template: list it on whatever auction platform you already use, open sales two to three weeks before the event, let buyers participate without needing to attend in person, offer a range of prize options rather than a single destination, and announce the winner strategically — before your biggest ask of the night, not after. The mechanics are simple enough to run with minimal staff time, and the payoff extends well past the raffle itself, into a fresh pipeline of donors an organization can now actually follow up with.

What Wine Quest Is Actually Funding

The golden ticket's success matters because of what it's funding. Questing's mission is to help people with developmental disabilities experience a full life, and the organization runs more than 23 programs and locations across Central Florida and Tampa, serving individuals from as young as 18 months old to as old as 88. Services range from a special-needs summer camp in Apopka to residential housing for individuals whose caregivers or aging parents can no longer provide full-time care. "We really want to provide those lifelong services," Pilcher said.

Wine Quest itself reflects that mission in a way that goes beyond fundraising mechanics. Questing brings some of the individuals it serves to the event itself, giving them the chance to participate directly in the evening rather than remaining behind the scenes. "We're big on community inclusion," Pilcher said. "We want the individuals that we serve to be out, experience these events, have a good time, be able to socialize." Guests, in turn, get to see firsthand who their giving supports — watching program participants dressed up, engaged, and on stage rather than reading about impact secondhand in a brochure. That visible connection between the party and the purpose is likely part of why a low-friction ask like the golden ticket performed as well as it did: guests weren't just buying a chance to win a trip, they were buying into a room where the mission was standing right in front of them.

Insights in this article are drawn from the Hey Nonprofits! podcast episode “Easiest $10K You Can Add to Your Next Event”, featuring Brittany Pilcher of Questing.