The best thing I have ever done with 40 dollars

Our family lives amply. We have a summer house, tennis lessons, and someone to scrub our toilet every other week. Or more specifically our four toilets because why would we ever want to wait to pee. We can pay for braces times 4 because now kids get braces twice. We grumble, we track, we wish it weren’t so, but we still have the money to buy organic berries to get their seeds stuck in those expensive metal brackets.

I have spent 40 dollars treating a friend to sushi lunch, getting a pedicure, and adding a new chime to my video doorbell. In fact most things we buy are MORE than $40. The electric battery for my fancier than necessary lawnmower costs $150. The replacement cushions for my outdoor furniture somehow add up to $800. We spend 3 times $40 on annuals to put in expensive pots to make the entry to our house more cheerful.  I could go on. And on. And on and on and on.

The staff led us in the same cheer that they offer each other every morning.
Last week my son’s middle school had its “big” fundraiser. Big of course is a relative term as this school with its 65% free and reduced lunch raised one quarter of what the elementary school raised despite having 3 times the students. If you can work through that run on sentence and that math you could attend the honors portion of his middle school. Instead of vacation packages and other opulent offerings we sold kid’s art and $5 raffle tickets. Luckily we sold a lot of both of these items. Despite living on teacher’s salaries the staff showed up in large numbers. They bought gift cards, signed up for each other’s pie making classes and even donated in the paddle raise.

We also featured choir, Shakespeare and chamber performances by students. I had worried that the kids would distract from the drinking and spending and realized quickly how wrong I had been. They arrived in gowns, straightened each other’s ties and trailed committed family members behind them. Ahead of time we had arranged to waive the $15 admission for families of performers and any other family who needed it. This was an inelegant effort. As you can imagine in a school with 750 students speaking a dozen languages there were some families who didn’t receive the full information.

One of these women arrived on the arm of her seventh grader. The girl’s eyes were bright as she scanned the room for the music stand she had painted. The mother’s eyes were cast downward. I had told the City Year volunteers working the door that all of the comped tickets were on their list. By the time the mom realized that her name was missing her daughter had found her music stand and was gesturing with excitement. The mother wouldn’t take a step into the room.

I had drifted over and asked the mom how I could help. She told me she didn’t need help she just needed to take her daughter and go…they didn’t have a ticket.

Setting up her stand. 
When I told her that every family whose kid had contributed to the benefit got free tickets she was suddenly as bright as her daughter. She hustled across the room and they looked together at the colorful music stand, their eyes as large as the ones her daughter had painted. The eyes on the stand cried tears of music notes. In a moment of life imitating art the girl’s eyes also welled with tears as she noticed that her stand was one of three featured in the prime corner of the room.

The price on the music stand? $40.

There was no way they could take it home. I suggested that they pose for pictures with it. They must have taken 25 shots. After digging into the buffet I saw the mother and daughter leaving arm and arm as they had arrived.

A half an hour later I went to put my name on the music stand that Oliver had painted, as instructed, in the colors of our living room. When I told him to do it I felt a bit guilty…this was certainly curtailing his creativity…but I wanted it to look good with our red leather couch. A few stands over the large eyes cried their musical tears.  As I added my name to this piece as well, I was pretty sure her mother would not care if it complimented their decor.

Such a little thing. One missed pedicure. One fewer sushi lunch. And yet it wasn’t a little thing at all.

The art teacher reported that the student had tears in her eyes once again when she realized she could bring her piece home. The next day Oliver thrust the following note into my hand:

I think about our bounty a lot. We give back in many ways. Even when we write big checks it never feels like enough. Yet somehow this forty dollar gift left me feeling more effective than many of my larger scale efforts. 

This student wanted me to have seen her mom’s face. But I already had. I saw the beauty in her mother’s facial expression as she marveled at the beauty in her daughter’s artistic expression.

I can imagine what she looked like when her daughter presented her with the stand to keep. And I can imagine it again and again as she watches her daughter create art supported by the music stand, and in some small way, me.

Do you have a small gift that moved you in a big way? I would love to hear your story…

Dinner Date

The president just asked me to dinner.

What? you too?

For those of you not on his mailing list, Barack is offering 4 seats at a “casual supper among friends” for supporters who give $5 or more. He will pay your airfare, and you get to rub elbows with some big names.

This is a brilliant fundraising strategy. He is building the bottom of his pyramid. Those of us who have raised money for a living know that it all starts from the bottom. Once our pyramid has a stable base we can move donors up a level by “engaging them” and showing the effects of their money at work.

Those of you who are interested in marketing…Obama just got you to PAY to join his email list. This dinner invite will get forwarded along and $5 is a low risk high reward proposition. Me+Barack+other powerful people. This is really voting with my wallet!

It is time to rethink exclusivity in favor of expansiveness. Create the same go big or go home experience, but broaden your guest list. Find ways, through lottery, raffle, or hometown hero nomination forms, to get MORE people involved. Use our technical connectedness to grow your base.

Let your big names and big donors take a night off- invite them to send an assistant, mentee, or grandchild in their stead. New energy, new ideas, this is the benefit of 0ffering a seat (or four) at the table.

Learning from Wesabe. And beta max.

Second, Mint focused on making the user do almost no work at all, by automatically editing and categorizing their data, reducing the number of fields in their signup form, and giving them immediate gratification as soon as they possibly could; we completely sucked at all of that. Instead, I prioritized trying to build tools that would eventually help people change their financial behavior for the better, which I believed required people to more closely work with and understand their data. My goals may have been (okay, were) noble, but in the end we didn’t help the people I wanted to since the product failed. I was focused on trying to make the usability of editing data as easy and functional as it could be; Mint was focused on making it so you never had to do that at all. Their approach completely kicked our approach’s ass.

Mark Hedlund CPO, then CEO of Wesabe says it like I need to hear it.  Many of you have asked (and at times shrieked) about why I have pulled winwin offline. The answer is in Mark’s quote. Read his full write up about his startup’s failure here.

To boil it down for those of you who dread the click through he blames his failure on three things:

  1. Himself- he worked “peerlessly”
  2. Focus on changing user’s behavior rather than giving them instant access to simple data
  3. Building an internal aggregation system rather than partnering with one that was already on the market.

His reasons for 2 and 3 are clearly understandable- he wanted to afford users secure, accurate and prescriptive views of their financial habits. To do this he avoided partnering with a crumbling and opaque data aggregation system. His hubris that he could help the our entire countries culture of spending is laudable…if not accurate.

Why is this a cautionary tale for winwinapps?

So many many ways.

  1. Our beta (now deemed prototype) version was written on a custom frameowrk, and was not able to take advantage of entire development communities advances
  2. I worked essentially alone, with expertise in the world that our customers lived in and not the technological field.
  3. I prioritized the ability for users to customize and manage every aspect of fundraising and marketing from the winwin dashboard, rather than making each tool as simple as possible to use.

Customers who met me, and were trained side by side with me felt that the app solved all of their organizations problems, and for that I feel some measure of pride. New users were unable to reap the benefits.

winwinapps 2.0 is growing slowly, and each module is stupid simple. Check out the first iteration using as a tester. Thanks for your patience as we re-build you a stupidly simple product to help you raise money.


I’m starting the design phase of the next winwin app. Its working title is Lifework or Worklife.

Imagine an app that helps you monetize all of the things that you already do in your daily life. Then helps publicize them on a mobile platform, and makes it super easy to give back to your community. Well even if you can’t imagine it, I am imagining it…but I need some help.

Although this app is all about one of a kind, individual goings on, we still need to bow down to the technological search gods every now and then. So I am seeking categories in the forms of verbs.

I’m aiming for the fewest possible verbs that can work to shoehorn in every kind of gathering, sale, activity, and effort in the universe. No problem right? Please comment and help me with this task.  My starting point:

Working-For volunteer sign up, services offered, think year round cinderfella

Learning-Lectures, symposia, and the like

Playing-sports, group hikes, kids stuff

Connecting-Networking, hiring, dating other legal interactions

Dining-eating and drinking.

Where does shopping go? That is a primary life event (and selling our stuff is one of the most time honored ways of monetizing our personal lives) Hoarding?  Isn’t working too broad, and sometimes it costs money…What about fundraising?

Social Venturers

I’d like to start each week introducing you to the people around me who inspire me to give my time, money and ideas.

There is no better place to start than with Leslie Halperin.

Bit ‘O Background:

Leslie has worked for the VT Women’s Commission and  worked on social mission programs for Ben and Jerry’s. (Those of you visiting the Waterbury Ben and Jerry’s can spy Leslie in their tour video talking about the ParterShop program.)

Her latest and greatest social venture is The Clothes Exchange. Which I have already written about at greater length. Short version: she has found a way to combine shopping and recycling to give back to a VT based non profit that works to improve the lives of women and girls. In her nice words: Clothes Exchange is a mission driven social enterprise, dedicated to turning clothing into cash for community benefit.

Why I love her:

  • She introduced me to fattoush salads.
  • She has the most welcoming family in the world.
  • She can write beautifully about anything.
  • She remains true to herself and her vision while always trying to please her family, friends, partners, and volunteers…a difficult balancing act that I now know is possible.

Why you should love her:

  • She sees the strengths in people and systems, and each beneficiary (both staff and organization) emerges from their relationship enriched and re-invigorated.
  • She makes philanthropy fun.
  • She has created one of the largest single fundraising events in the state of Vermont, which almost doubles each year.

So here is the point of this…even those people that I hold up as models need help. Looking for leads on the following

What she needs to do more good:

  • An accountant. The Clothes Exchange is growing rapidly, and Leslie needs someone to watch her books and her back.
  • Retail/warehouse space. Her pop up shop this weekend attracted 150 shoppers and made $6600+. A totally volunteer run event the proceeds went to sustain The Clothes Exchange and to support Vermont Children’s Trust Foundation. Despite the generosity of Russ and Roxanne Scully (who donated their incredible Pine Street Space, and own The Spot) and 1-800- got junk, Vermont Tent Co, and her clothes exchange board this was still a backbreaking event. Leslie was on her feet for 14 days, racking,tagging, etc. A permanent space to store clothes, and act as an office would make these satellite events much easier to execute. Men’s shop anyone? Holiday sale? The ideal space would be 800-2000 sf and have lots of parking. The Clothes Exchange can contribute something, but not full market value. So send this idea on to your landlord, and realtor friends.
  • An interior designer. Leslie is always stylish, and her house is equally appealing. One half of her living room needs help though. Anyone out there want to lend your eye?

Leave any connections in the comments. Thanks

Lessons from the line

Event organizers dread them…but why not take advantage of your captive audience.

Look over there at The Clothes Exchange. Last year we had 400 shoppers, this year we almost doubled that. What does it mean? A bit of panic for sure, last minute streamlining the check in process (save those marketing questions for check out or your follow up survey) but it also provides an incredible opportunity to establish our brand, educate our shoppers, and raise extra money.

Getting in the Door

  • Set the stage. Your decor, customer service, all should appear in the waiting area. We have 8 or more “greeters” who hand out fresh lemonade, explain the process, and answer any questions shoppers may have. Next year we have the greeters administer our marketing surveys in iPads online.
  • Share your message. Once they are in the door our shoppers are interested in one thing only: THE CLOTHES, this is the time to share the mission of the our beneificary The King Street Center, and the logos and tag lines of our sponsors.
  • Whet their appetite. We hang sample items (shoppers can pull off of clothes lines and buy right there), as well as set up outward facing windows with one of a kind temptations. When possible we pipe music into the line area, and offer bits of entertainment.

Getting out the Door

  • Upselling and personal appeals.  This is our last chance for raffle tickets, branded merchandise and a great opportunity for thank yous- we staff the check out line with board members and staff of our beneficiary organization. An appeal from them has more meaning, and a thank you together with a quick story (viewed now as connection rather than distraction) can turn a shopper into a supporter.
  • Rethink and revise. For 2011 we are relocating our silent auction to the check out holding area. We will set it up on skinny tables, or have clipboards hanging from clothes line. We will use the auction as a way to define the line, and give folks waiting to check out a chance to bid.
  • Bottom line basics. No matter how busy the line, we always take time to ask for a specific round up donation, and double check the email address.  Emails are necessary for their winwin receipt, thank you, and future communications. Our beneficiaries often add hundreds of local supporters to their lists each year.

Tips from Switch on clarity and directed-giving">Switch: How to Change Things When Change Is Hard</a><img src="// the Founder’s Bookshelf:

I am currently re-reading “Switch: How to change things when change is hard” by Chip Heath & Dan Heath. Amongst the many dog-eared, and underlined sections is a brief line on page 17: “What looks like resistance is often a lack of clarity.”

The author’s example is a public health campaign in West Virginia that specifically directed residents to switch their milk drinking from whole to 1% or skim. Instead of the valuable – but diffuse and difficult – goal of simply “acting healthier,” the campaign gave clear instructions.

What can this mean for non-profits? Quite a bit.

At a recent fundraising auction checkout, one of our cashiers requested “an additional donation to support the work of the beneficiary.” Her line had a smaller than 5% donation rate. Our other checkout line asked winning bidders to “round up their purchase by 2, 5, 10, or 18 dollars” (whatever brought them to the nearest $100 figure). This money would go to purchase a new pick up truck to be used by members. This second line had a 37% round up rate. For a small non-profit that was the difference between $10 dollars in the first line and $475 in the second. Neither was enough to buy a pickup, but with clear instructions the actual dollars in the bank increased by 40 times.

What about you? How specific are you with your asks? Do you tie gifts to specific programs, ask for discrete amounts at particular times, or take advantage of triggers in the environment of your supporters?

Other take home messages from Switch for fundraising:

  1. Follow your bright spots. If a campaign, donor, or programming is exceeding your goals, try to determine why and replicate it.
  2. Marry long term goals with short term critical moves. Your mission is critical, but showing your staff and supporters how you will get there shrinks the change, and energizes giving.
  3. Script the moves. For an organization that fights homelessness, linking a monthly gift equal to 1% of a donor’s mortgage payments can keep your mission front of mind and the amount and timing of donation clear.
  4. Grow your people. Increase their role and identity within your organization. Donors who support a public health campaign might become “messengers” – with their donation receipt you can arm them with support materials and task them to teach 10 friends the importance of breast self exams.
  5. Act more like a coach and less like a scorekeeper. Everything looks like  a failure in the middle. Focus on the valleys of a program as learning opportunities rather than failures. There should be no “never” – only “not yet.”
  6. Use the score when it can help you. The herd mentality can work for you. If the majority of your board members have exceeded last year’s gift, use that fact. People tend to fall in line with their peers.

What is your favorite take home from “Switch”?

– Anna

winwinner Wednesday: CarShare Vermont

CarShare Vermont is cool nonprofit on a mission to provide Vermonters with an affordable, convenient, and reliable alternative to owning a car.

The idea: If more Vermonters skipped owning and driving cars in favor of using shared vehicles just when they needed wheels, we’d reduce greenhouse gases, save money, and create a stronger community.

How it started: In 2002, a group of Burlington residents caught wind of “car-sharing,” an innovation that was growing in cities across the country. The group reached out to the San Francisco Bay Area’s nonprofit City CarShare, where by chance, Vermont native Annie Bourdon answered the phone. Annie collaborated with the group over several years, and when she finally moved back to Burlington, she helmed a grassroots effort to get the initiative off the ground. By 2008 many volunteers (individuals and businesses) were involved, and the service launched in December 2008 as CarShare Vermont.

The winwin: Area residents use one of 5 Priuses and 4 Imprezas parked throughout Burlington, VT to get around town, do errands, etc. Residents don’t have to bother with the expense and hassle of owning, maintaining or parking a vehicle the city has less traffic congestion, and the air has fewer greenhouse gases. Now that’s a winwin!

How they used winwin apps: CarShare Vermont’s 1 year anniversary event, “Share the Love,” was a fundraiser at the Main Street Landing in Burlington, VT. CarShare was a tester of winwin apps’ early software, using it to promote the event, register attendees, and manage their fundraising auction.

More info: CarShare offers memberships for individuals, families, and businesses with rates starting as low as $4.95 an hour and $0.25 per mile, including gas and insurance. Users can reserve by the hour or day and only pay for what they need. For more info, visit

About “winwinner” Wednesday: Each week we profile one of the nonprofits using winwin apps to make the world a better place. If you’d like to be featured on our blog, drop us a line!