Once I was a dream girl. Not the Broadway show kind of Dream Girl, but the Possible Dreams kind. I was auctioned off. Don’t get the wrong idea—it was for a good cause and it was an all around great experience.

But while I was having my five minutes of Island fame, I failed to notice who the real dream girls (and guys) are when it comes to staging an event which is the biggest fundraiser of the year for an Island nonprofit that serves an estimated 6,000 Islanders through multiple programs. That would be the Possible Dreams Auction and Martha’s Vineyard Community Services, and the real dream girls are, of course, the organizers and volunteers who deliver the dreams. (You’ll have to forgive me for my clueless state – really I was just worried about pulling off the dream, which was a cooking class for eight in the historic William Street home of Dawn Braasch, owner of Bunch of Grapes bookstore. I shouldn’t have worried. We had the nicest, friendliest, most easygoing group of dreamers you could ever hope for.)

This year is the 40th anniversary of the Possible Dreams auction, which benefits Martha's Vineyard Community Services. Ray Ewing

But with a few years passed and my own awareness of Community Services heightened, I found myself intrigued with the success of the auction as it approaches its 40th anniversary this summer. That’s how I came to meet Jess Rogers, development coordinator for MVCS, and Liza May, chair of Possible Dreams. And to understand once again (as often happens when you scratch the surface on this Island) how generous Islanders – and Island lovers – are with their time and services when it comes to supporting a good cause. There are an astounding 40 volunteers on the Possible Dreams committee (each has a dedicated responsibility); dozens of Island businesses offer in-kind services and donations to the auction. Then of course there are the sponsors – more than 30 this year – and the dream-fillers themselves. And the hundreds of people who buy tickets to the auction (see below), which this year is on Sunday, July 29, at the Winnetu resort.

It should be noted, especially at this time of year, when fundraisers like Martha's Vineyard Museum's 20th Annual Evening of Discovery (June 30), FARM Institute's Meals in the Meadow (July 14), Vineyard House's Water Tasting by the Sea (July 19), and Featherstone's Annual Gala (July 21) are happening, that this spirit of generosity and service is not limited to the folks who work at or support Community Services or to the dreams committee. But with 40 years behind them, a unique concept, and a total amount of funds raised that is over $11 million, they are one of the best examples of how to keep a good thing going.

Thinking in and out of the box

Jess Rogers in her office at Community Services. Fundraising only begins with the Possible Dreams auction. Jeanna Shepard

When I met Jess and Liza, I discovered that despite being at different points in life – Jess is about to have a baby and Liza has sent her last baby off to the real world­ – the two women share a level of professionalism and a common goal: not just to maximize the funds Possible Dreams can raise, but to maximize the opportunity to bring awareness to all that Community Services does (below).

Jess and Liza began working on the auction together four years ago when Jess moved from Boston, where she worked for JDRF raising money for Type 1 diabetes research. She promised her Island-raised husband that she’d be open to living on the Vineyard if they could find the right jobs. Liza got her start in fundraising with an organization similar to Community Services in Alexandria, Va., the Campagna Center. She first volunteered as a 22-year-old newlywed when her new mother-in-law demanded to know what she was going to do for her community. One day turned into years and fundraising became a passion. So when Liza and her husband bought a house on the Vineyard, their realtor, Sandpiper’s Elaine Miller, turned to her and said, “I’ve got a job for you.”

Follow the money

Forty committee members and many volunteers pitch in on auction day. Ray Ewing

One of the first things Liza and Jess realized when they sank their teeth into planning the auction was that the live dreams were only one part of the fundraising equation. With her background Liza could see that the number of sponsors for the event—at the time about a half-dozen—could easily be increased by approaching individuals and other businesses for supporting sponsorships.

“Fundraising has changed. People do have deep pockets, but not necessarily always for buying auction items,” Liza said. In general, the trend in fundraising is leaning heavily towards sponsorship of events. In just a few years, Liza and Jess have turned a roster of six sponsors into almost 40 in 2017. Over 30 have already signed on this year, with Ernie Boch, Jr.’s Subaru of New England back for a second year as presenting sponsor. Allan and Shelley Holt, as well as the Swartz Foundation and Comcast, are generous sponsors as well.

“The beauty of sponsorship is that heading into the day of the event, which is chaotic and stressful, since you never really know how much a dream is going to raise and how much people are going to bid, we already have this great pool of funding,” Jess said.

For Dreams chair Liza May, the live auction is only part of a successful formula for a great evening of fundraising. Ray Ewing

“Last year we raised right around $150,000 in sponsorship funds, and our goal this year is $165,000,” she said. They feel optimistic they’ll reach that goal this year, with $124,000 raised to date.

In addition to increasing sponsorship, the planners are constantly thinking of of new ways to broaden the event and to be more inclusive. Liza suggested the idea of a raffle (p. 14) when she came on board. It was a hard sell to the committee at first but is now a great success, raising $10,000 last year. Other ideas, including a golden ticket and super dreams, are in place to help the auction reach its 2018 goal of $500,000.

But reaching that goal has more challenges than you might think. Because the Possible Dreams auction is well-known and has been a successful fundraiser, Jess says that sometimes people believe they don’t need to give to MVCS. The reality is that if the dreams auction reaches that goal of $500,000 this year, Jess and her development team at MVCS still need to raise more than $1 million to fill the funding gaps for all the programs.“On average, each year the development department is charged with raising the funds to make up a $1.7 million gap in funding,” Jess says. “And every year that number gets higher. Some programs have a wider funding gap than others, but every program is in some way subsidized through the private funding that the development department does.”

Building Awareness

Jess hopes that this year the auction will bring more awareness to the range of programs Community Services offers (below). “Something we [Liza and I] have tried to do since we’ve been working on this together is to bring the mission of the organization into the event, because for a long time that wasn’t happening so much. Some people didn’t even know what they were coming to support,” Jess says. “Our goal this year is that everyone leaves with a deeper understanding of the breadth of the services we offer.

One way they are going to do this is with the “Fund-a-Need” feature (also referred to as a call to action or a paddle raise) they added two years ago. Before the live auction begins, the audience hears a story from someone who has benefitted substantially from one of Community Services’ programs. Then auctioneer Sherry Truhlar comes up and tells everyone they will have the opportunity to help close the funding gap for this particular program. Unlike bidding, where the money comes solely from the winner, in a cash appeal, all donations (in designated increments) are accepted. This year, for the 40th anniversary, Liza suggested they focus not on just one program, but several. As a result, they've tapped a great speaker who will relate how not one, but several MVCS programs have helped many members of his family. “We’re going to try to tell this whole story of Community Services through one family,” Liza said.

That seems only fitting. In expanding the Possible Dreams auction to be as inclusive as possible, Jess and Liza bring to it the spirit of both Community Services and the Vineyard.


What is Martha’s Vineyard Community Services?

MVCS is a non-profit organization that provides comprehensive support, counseling, education, and services to an estimated 6,000 Islanders through several core programs that include youth support, veterans support, substance use recovery, domestic and sexual violence advocacy, disability services, employment services, childcare, family education, a Head Start program, and a Thrift Shop (Chicken Alley). While many people may associate Community Services with the one program they may be familiar with—the early childhood programs, The Island Counseling Center, the Connect to End Violence program, or the Island Wide Youth Collaborative—the organization is all of these programs and more. To learn more about MVCS, visit mvcommunityservices.com


Dreams do come true

The Possible Dreams auction is for everyone. You don’t have to buy a fancy dress or meet any kind of financial bar to attend the party. A ticket for admission is only $25. You can then purchase a food and drink bracelet for $20, which will get you five drinks or bites (a $5 discount, since everything, including cocktails, is priced at $5). This year there’s also a special ruby ticket for $40 that will cover both your admission and your food and drink bracelet. Everyone who plans to attend is encouraged to buy a ticket ahead of time on line at mvcommunityservices.ejoinme.org/RubyPDA   

Once you’re there, if you’re not planning to raise a paddle during the live auction, you can still participate in the silent auction or buy a raffle ticket. Raffle tickets are one for $10, three for $25, and 12 for $100. Prizes range from a Patriots package to a Nantucket getaway to a set of jewelry designed by Stephanie Wolf just for the auction to a $900 Taste of the Island gift certificate to restaurants. Buying a raffle ticket is a great way to support Community Services if you want to make a small donation.

Professional auctioneer Sherry Truhlar of Red Apple Auctions (here with auction chair Liza May) keeps the auction moving at a good pace. Ray Ewing


Dream Big

Here’s a sneak peek at some of the “live dreams” at the 40th anniversary Possible Dreams auction.

The “live dreams” are what make the Possible Dreams auction so special. “They’re unique ‘unbuyable’ experiences,” chair Liza May says. Over the years dream winners have walked across the Brooklyn Bridge with David McCullough, gone for a sail around the Vineyard with Walter Cronkite, toured the set of Ghostbusters with Dan Aykroyd, had lunch at the Washington Post with Katharine Graham, spent an afternoon painting with Allen Whiting, and had their DNA tested and explained by Skip Gates. They’ve spent time on TV sets, visited with professional athletes, cooked with professional chefs, toured museums behind the scenes, and hung out with all manner of Island personalities.

This year authors, athletes, artists, and celebrities of both the off-Island and on-Island variety are stepping up to offer exciting dreams. 

At press time, Liza and Jess Rogers, development coordinator for MVCS, had secured 19 of the 21 dreams they hope to offer and were happy to be wrapping the list up a little ahead of schedule. The latest dream confirmation is a Seth Meyers New York Experience. The winning bidder and a guest will be invited to attend a taping of Late Night with Seth Meyers and will have a meet and greet with the host. Accommodations and some additional NYC experiences will round out the package.

If you’re the winning bidder on author Elin Hilenbrand’s dream, she’ll mention you in her new book, Summer of ’69, and invite you to a book club luncheon at her Nantucket home.

At the very outset of planning for the 40th anniversary, Vineyard painter and farmer Allen Whiting (who is now also technically a movie star after the release of the film, A Painter Who Farms) offered to donate a painting honoring the anniversary theme of “lighting a path [to a bright future].” Whiting is just one of many long-time Island supporters. Windsurfing legend Nevin Sayre will offer a windsurfing lesson to a winning bidder and a guest. Interestingly, it was Nevin’s mother, Harriet Sayre, who first asked Art Buchwald to serve as the emcee and auctioneer for the auction in the early days. 

Speaking of throwbacks, a popular dream from back in the day makes a return this year: A fabulous dinner with singing waiters. The updated version will feature Vineyard Sound as entertainment, and the boys will do a bit of serving, too. Private chef Gavin Smith (the Food-Minded Fellow), will cater the dinner at the winning bidder’s home.

The dream that brought the largest dollar amount in last year is back: watching the OB Fireworks from atop Offshore Ale. And this year a second fireworks watching dream—this one on a Packer tugboat—is in the mix. Other returning dreams include the Stanley Cup winning Washington Capitals package and the Boston Bruins dream. This year cookbook author and grilling guru Steven Raichlen will offer a 3-hour Barbecue University class. You can also bid on other dreams that include a trip for 8 to Ireland, a two-night stay at the Charlotte Inn with dinner at the Terrace, a cocktail party at the Granary Gallery with Alison Shaw, a Murdick’s Fudge getaway to Mackinac Island, and a sail on a Black Dog schooner with author Lisa Belcastro. 

Stay tuned and get ready to raise your paddle on July 29th at 5 p.m. (Silent auction begins at 3:30 p.m.)