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…

What I do do

More heat in hot places, more cold in cold places. More taxes and fewer services. A litigious society where one accident can derail a hardworking family. Increasing health care costs with decreasing compensation for the people who provide it. The modification of food so it begins to kill us instead of making us stronger. Sheltering of corporate rights and protection for the people who make choices, sometimes illegal, that focus only on the bottom line. Whole areas of cities that are given up on by the state that is supposed to repair and police them, instead ruled by gun and drug trade. Crazy stories of people being raised in captivity, sold for parts. The bad news is everywhere.

Blocking it out only works so well. One day you may drive on that dangerous street, or have a kid born prematurely. It is hard to trust that the mechanisms we have in place can fix these problems large and small, individual and systemic. These checks and balances were here all along. Where has it gotten us?

If you think the world is unfair, and many or most people are getting screwed, even if it is not you what could you do?

What should you do?

There are some people who really go all in, move to the third world and embed themselves providing healthcare, religious education, school buildings, and pumps for fresh water. They are no longer of the problem, and are probably part of the solution, at least in the way they can be. Hands on.

Others start non profit organizations to try to lobby the government, and pick up the slack where possible. They are bogged down by licensing and paperwork and reporting and their programs do as much as they can, and how much is that? There is always a need for more.

Others bail altogether. Buy an island, build a boat, and feed their kids on locally grown food. They are living lightly on the earth, and still is this an act of protest or of self protection? How do we measure the value of this.

Despite its economic diversity for the most part I live in a bubble where people are getting screwed less. And some of us are doing the screwing. We debate which mountain to buy our season’s passes at and which piano teacher will be more motivating to our second grader. We worry about the cost of college and the debt our kids will have, but not whether college is an option at all. Most of us have cars that run well, and pay someone to work in our yards at least twice a year. Things are easier in Shelburbia than many places. And still…still… what can we really do?

If we aren’t going into public service, starting an NPO, or moving to an island what is possible, what is reasonable, and can it matter?

Can the choices I make fill every kids belly with food, or regrow the ice caps, can it give bus drivers fair schedules and make cities walkable, can it re structure the food system. No, no, no, maybe a little?

It feels like peeing into the ocean. If change on a personal level feels so ineffectual why do we do it? Even the largest sacrafice we can make, if we offer every hour of every day in service to correcting some of these wrongs will it make a difference? Some?

Are we going through motions to decrease our own guilt, model empathy for our kids or something more?

I want to be able to lead a comfortable life, one with sports utility vehicles, private summer camps, local art and Saturday morning farmers markets. I want to hire tutors for my children if they need them, and teach them lifetime “skills” like tennis. I want to spend $10/ gallon on raw local milk and know the names of the beef that I eat. I want the life of the 1%. Go ahead and make fun of me shopping at whole foods, I’ll be that patsy. And I want everyone else to be able to be a patsy too, if they choose.


Would I trade? Would I just randomly trade with another family of four somewhere in America? I don’t think so. I would do it for acclaim, or the story or the “experience”, but would I simply switch lives with them, if their lives were missing many of the privileges of mine? No. Would you?

Here are the things I do do. Pissing into the ocean as they may be.

For each privilege or luxury I will pay for someone else to do that same thing. I send my boys to sailing camp, I pay for two other boys to go to sailing camp. A 1 for 1 deal, but is sailing camp the very best way to have spent that money? I don’t know. A lot of times I forget and just get a babysitter for a night out. This is a luxury too.

I give gifts to non profits, non profits who focus on essential needs, education, art, literacy, science, health, farming, education. I don’t know the ROI, nor do I expect to. Hopefully some of it helps.

I invest in start up businesses directly, I am a partner in a local Venture Capital Fund that has as part of its mission to focus on local businesses, and I have helped fund and found a tech accelerator here in Burlington so some of the young talent might stay and work here, and perhaps become successful enough to employ other people who will be able to stay and work here and support their families.

I work with non profits to expand their fundraising efforts. Last year before I slept out with Specturm I met with the staff and pitched the idea of having kids and other organizations sleep out as well, at sites other than the main sites. They took that ball and ran with it. I gave nothing other than the concept, they created materials to support people who slept out and this year they doubled their participation. There are other stories like that, where I try not to remain the only one writing the check. I am not even close to wealthy enough to make a difference.

I buy local art. The creative economy is vital to growing a sense of place and growing a place. It is an old story. Artists discover an area and then it is gentrified. They are pushed to the edges and they do what they do and create anew. I am not the only one supporting the local art scene. Generally original art is not the first thing people think of spending their disposable income on. If there even is such a thing as disposable income anymore. I encourage you to try though. For a pretty small investment you might fall in love with the permanent window in your home that allows you to see the world through someone else’s eyes.

Is this as much as I can do? Surely, obviously, definitely not. Does any of this even make a fundamental community changing mindblowing difference? Nope. Do I feel self righteous and justified in my lucky life? Sometimes, a little bit. But mostly no.

I have no answers here. Just always more questions. What can we do? What should we do? How much redistribution is necessary and effective? Is there any amount we can keep for ourselves that isn’t too much? I don’t know.

Here is what we decided for our family. I have to say I am a bit shaky as I type this, because I used to feel unwavering at least in my personal disclosure and lately I have been a bit bumped and bruised by it, but here goes.

In the past 3 years we have earned 4 million dollars. We put 950k into properties that we own. We put 1 million in the bank. I gave away and invested the rest in local ventures. To me it feels like a lot. I don’t get to give myself everything I want. I don’t say that looking for sympathy or praise. Just explaining how it feels. There are certain higher end things (like the Tesla) that we could not afford to buy. As we are moving to a more expensive city we had to go down several rungs in quality of house. I would have been happier buying a nicer house. I feel that one a lot more than the car. We will be living for a time with furnaces that don’t work, windows that leak, and a kitchen that only fits one cook. It will be less comfortable than we are used to. I still get most things that I want. I can go to the grocery store buy organic products and wince at the bill, but still pay it. When I reverse into the mailbox for the third time I can afford to fix my taillight even though it is unreasonably expensive.

Of that 2 million plus that has left my account the vast majority of it doesn’t even have a chance of coming back. Sometimes I wish I were more discerning and shrewd, so I could put that money to work harder or better. Have those gifts and investments be more than one time gifts. The idea of supporting things in perpetuity rather than in start up is appealing to me, and I haven’t been able to make that happen.

I don’t know where to volunteer, what to donate, or what to protest in a way that will really fix things. I don’t know if things can be fixed. Except, eventually, our furnace.

I approve all comments, but would hope that you understand that no one chooses their circumstances in life, just how to respond to them, and this post is one in a series as I continue to navigate how to live with a higher than average but not ridiculous amount of wealth. I know I am lucky and do not offer any answers. Just questions.

Rain boots, rain boots, go away.

An Anna & Angela post.


I really don’t like my rain boots.  It’s raining today and every time I put on these boots, I think, “I really don’t like these boots.”  Cute rain boots exist, but mine are not cute.  They are utilitarian and totally functional, but they have zero personality.  I wear them because they were free.  Sent to us by a very generous friend of my husband’s who works for an outerwear company.  Free and void of any personality.  I really don’t like them.

But I wear them every time it rains, and when it’s not raining, I don’t shop for new boots.  I don’t even think about it.  But every time it rains I’m reminded that I do things for other people.  I do things to make other people happy.  I wear the boring rain boots because my husband always worries about money and why would I buy cute, expensive rain boots when I have a perfectly good pair of rain boots that just happen to be ugly?  I’m not that girl – the one who has to have cute things.  I’m the one who does what’s easy, partly because I’m lazy and mostly because I don’t like to rock the fucking boat.

Argh.  But what does MY boat look like?  Am I constantly a passenger on someone else’s fucking boat?  On my boat, we wear cute rain boots that make us feel good even if they cost more than rain boots ever should.  I want to be the captain on my own boat – or better yet, a pirate.  I will take over my own boat because the captain version of me is a pussy who needs to have her world rocked a little bit.  She needs to wake up and realize that IT’S OKAY TO HAVE YOUR OWN BOAT!!  Your boat can veer off course from time to time and rejoin the fleet later on in the voyage.  Your boat can explore.  And hey, the people from the other boats might even want to come aboard once they see how fun and free and expensive your boat is.

What the fuck am I even talking about?  I don’t sail.  I have no idea how to carry this metaphor through.  But I know that I don’t like my rain boots.  I know that I don’t take very good care of myself.  I know that I feel eternally conflicted; caught between doing what’s best for the people I love and doing what I actually want to do.  Thankfully, the two are very often one and the same.  But every now and then, I just want to buy the cute, expensive rain boots.

Cute rainboots that probably smell like plastic.
Cute rainboots that probably smell like plastic.


A few years ago I bought red rain boots with white polka dots. I forgot them in the closet for a bit. It would rain and I would wear whatever shoes I had on. Then one day I found my polka dot boots and my heart soared. I thought, what ever would be better than polka dots on a rainy day.

So I wore them.

And they smelled like plastic off gassing. And they made my feet slide around inside because they were molded from poison.

So I put them back in the closet. And every time I opened the door I could smell them more. Which didn’t make sense but seemed to in fact be the case.

So I got rid of them in the move. I was planning to donate them with all of the other stuff that I gave away, but I didn’t want anyone else to have to suffer the fate of the cute boots. The smelly, uncomfortable poisonous boots.

As for boating…I seem to sink most ships, so I’m trying to stay off the water. I mean that literally, I have owned and sunk three boats. That’s not a great record.

From what I know about your life you do an excellent job balancing things for you and for those around you.

The money thing is a bit trickier. Spending as little as possible seems to be a core value for your husband. I wonder, is there a way for him to accept that as his core value rather than a full family mission? I live at the far far other end of the spectrum, so I don’t think I am one to give advice. Its tricky though when one partner’s dogma lines up with the general world view of virtuous (don’t spend more than you need.) It makes it more difficult to establish a family norm.

I have been thinking and talking about spending and sharing more. Why is building wealth important?  If your family is comfortable, and your kids are taken care of why not spend, share, and donate the rest? There has to be room for cute boots. If you buy them from the right company the money pays itself forward. Maybe not for your family, but your community. And every time you wear the boots you can smile and look forward to the rainy days of life.

Just try not to pick boots that off gas.


I am going with none of yesterday’s choices. I started writing up Good Buy, and there is certainly material there…but the media files are too much for me this morning. I only have charcoal grey and white to offer so that is what you are going to get.

I was up until 2 am zillowing like a mad woman, researching every house over 850k in Vermont, tracking their days on market and their price drops coming to the conclusion that if the past is a predictor of the future in real estate we may actually be fucked. There are some real steals out there for 1.2, 1.3 though if you are in a position to sit on a property for 5 years while Vermont catches up with the rest of the country.

I’m not really sure about the high end market in the rest of the country though, so perhaps our bubble is a bubble and it all just shows that you don’t know. If someone could guarantee me a sale this summer or next summer I would just sit tight and maybe even put the dock in, but there is no one who can really do that so I have to start running numbers on furnished weekly rentals and then I am just guessing about other things. So I was “busy” with this until 2 am when I knew I really needed to sleep. This is not my usual insomnia pattern, generally I fall asleep before my boys only to wake up at 2 or 3 to worry whatever worries can only be attended to in the single digit am hours. Those elusive problems that seem to dissipate with daybreak. You might think that if they can’t survive the light of high noon inspection perhaps I should not allow them space in my brain at two or three, but I think I am just an early adopter of everything, including incubating worries. They are obviously going to get much worse so I’ll just get a jump on them now, while everyone else is sleeping.

I try my usual tricks. I start up the Patriots Football weekly podcast and it obliges me with an infinite loop and at every commercial break it seems they play the same bit about Fred checking out Brett Farvres junk (this is way before the senators got into the act, when dick shots were left to the pro-bowlers) and Andy screeches out that he would never google a man’s junk that he LOVES breasts. And I think, for like, the 300th time that I have breasts and I use some eighth grade math to decide that Andy must LOVE me. And that makes me just a bit happy until I realize it is like 2:12 and tomorrow is walking wednesday and the boys really need to be OUT THE DOOR at 7. So Steve is just going to have to get up early.

So he does and they make it out and I am still asleep when Steve steps into the room dressed and showered and coffeed. And in my mind I am in my running clothes, but really I am squinting from weird mistimed sleep. So I ask him to carry the suitcase up from downstairs and I step on the scale and it is worse than I even thought, but I am too tired to feel bad. So I text my running partner to tell her how much I don’t want to run but that I will. And she texts back that her foot is broken and she can’t run. This is the kind of broken foot that is a lot like my brain tumor, or clogged arteries. There is something wrong in there, but it is likely not acute. So I set aside the potential sadness for my broken friend (can’t be more than a stress fracture I figure, knowing not a thing about this) and realize that the only polite thing to do is to wait for tomorrow when her stress fracture has healed and we can run together. I mean, thats what friends are for. So we both decide to go back to bed and its not even like skipping, more like postponing and since I am only in my running shoes in my mind it is super easy to just push one cat aside and snuggle next to the other one and answer the call from my mother that comes the exact moment 8:02 that I am back in bed. So I lie there for a while and talk to her about tumors (real actual ones) and cars (she has decided to put money into her 10 year old paint peely volvo, she is such a BAD nouveau rich person, she totally acts like old money) but then we discuss the kid’s college accounts and how Leo, at age 7 has ferreted out their existence and asked if the money NEEDS to be used for college, and it seems like at least one generation has an uncomplicated relationship with money.

I’m awake now, and figure I should write that Good Buy blog post, because the entire time I was zillowing I was coming up with funny phrases about it. And since my laptop isn’t in bed (big mistake) I get up and use the desktop but for the 5th time in the 2 weeks I have had it it has a connection time out. Does it have a little stool in the corner? Is it allowed to reconnect once it feel ready to join the others?

So I come downstairs and get the laptop and am going to write that post but the drop box isn’t syncing and I’ve just about had it so I go to the bakery. I am hosting a new friend for tea, and I want her to be a real friend so I don’t clean for her. Like the first time the new dad goes out for milk and comes home 8 minutes later and then the 3rd and fourth time it takes him 11 minutes because he checked his email in the car or just sat still in silence and the new mom is like YOU TOOK 3 MINUTES LONGER THAN LAST TIME ARE YOU HAVING AN AFFAIR? Except its her hormones talking and she didn’t even ask about the affair, she just begrudged him the 3 extra minutes because if she had 3 minutes she would sleep or wash herself. But she doesn’t so she can’t so THREE MINUTES. In any case my house is actually MESSIER than normal so the new friend will think we are minorly messy and then next time she will see that we are on the neat side of the spectrum if not holding the immaculate post at the end like she is.

But mess aside there needs to be food and Steve hasn’t been home to bake so I head to the bakery. On the way there I have time to see a snowflake. I knew you were around here somewhere I tell it, you can’t surprise me sneaky little snowflake. I head forth for pastries trying to determine if I will buy a tea there or not. Benefit. I will have tea. Cost. It has a cost. I am preparing for a happy reunion with the counter staff, who despite never learning each others names with dozens and dozens of requests on both sides, is one of those people that just makes me break into a huge grin and its seems the feeling is mutual since she always recounts how recently (usually very) I have been there and really really how glad she is to see me again. It is not her though. It is someone new.

There is a stylish younger than middle aged couple at the counter and there is obviously a low level problem because both sides are apologizing, and it seems they are not helping each other feel better. The dude and I stand back and watch, and in the end the customer seems satisfied and the staff seems a bit on tilt. Not, like angry on tilt, but like she should be treated with caution, because the next problem might make her really sad. I stay uncharacteristically in character of ‘person ordering food at a bakery counter’ and I order the food and she rings me up, and I ask (hope) she has forgotten the tea, but no, she has remembered it. Right on counter lady. So my order is 8 items, 4 savory 4 sweet, new friend. I study her as she studies the items. She is of mixed race, some sort of Asian, I’m thinking Chinese and probably white. She is larger than your average Asian, and I catch myself thinking of all of my trim petite Asian friends one of whom gets stuffed when she has a pomegranate. Every time I see a pomegranate I say out loud “I’d really like to have a pomegranate, but I am just too full.” Which is super funny to me, and not usually to my co-shoppers. So then I think about buddha, and he was pretty large, and Japanese I think. Wow, I’ve been studying Zen buddhism for a year and not only do I not really know his nationality, but I am up at night perseverating on house prices. I may need to ask for a refund. So then I am laughing out loud at the idea of demanding a refund from the Zen Center, and probably not Japanese or buddhist counter person looks at me thinking I am laughing at her and I realize I have slipped out of my role of ‘polite bakery orderer’.

So she is holding up a box muttering to herself “I think they will all fit” and it is so clear that they will not all fit but I know that people learn better through experience so I am quiet and think instead about her musing aloud. I muse aloud a lot. But its not really for me, and it is not really musing, it is maybe more like quipping, I try to draw the people around me in. When she does it, I feel it is really for her, not for me so I leave it be and wonder if she has a blog. I would like to read her blog. And then I think of blogging as navel gazing (what better post than this for that…the super super long version of ‘I’m sipping a cup of tea’) and realize that is isn’t really like gazing, blogging is more like masturbating in that you expect the exercise to give you some release, and take you to a different place. So I tap a quick note on my phone just about the time that she has figured out that 4 of the 8 items will fit in her box. And Siri delivers me a little gift, Madturbating, the note reads.

The act of improving ones mood through self pleasure. Or maybe the opposite…you are feeling fine but then things are coming together as quickly as you would like so you are getting a little mad. Or the individual sex act of a crazy person. Whichever it is I like it. Madturbating. Any of which is a good proxy for blogging. The act of improving a bad mood through writing about ones self. Or You think you are spinning a great tale, but things just don’t come together the way you expect and the post makes you mad. Or, obviously, the individual writings of a mad person.

She has both boxes packed and I grab them, balancing the hot tea on top and head to the car. Standing at the car door I cant’ figure out how to open it without setting the tea on the curb and since I am a bad parker that is too far away. (Do I not want to leave the tea unattended because of the rash of rohypnols in Shurlburbia?) So I tilt just slightly and avoid scalding my hand, and move boots and vests, and parking tickets, and books, and boxes from the front seat to the back. We are on our way home the tea and me and I swing elegantly out of the three quarters of the parking space that I had taken up and the entire tea dumps backward onto my pile of stuff. I watch the vest absorb it. No tea for me.

So I sit down to write this post and get exactly to the point where Siri tells me to go madturbate. Or at least tells me to use the word in a sentence and there is a knock on my door and she arrives (not Siri, the new friend) with a bakery bag in hand. It is not a box so I know we won’t have any duplicates other than the duplicates I bought and she unpacks her bag and she has brought 4 savory and 4 sweet items. So the two of us have 16 baked goods to choose from. Or, 6, because she bought hers ark style and I just got 4 apple crisps and 4 savory bacon croissant bread puddings with melted cheddar. And yes they are as good as they sound.

Finally I can have tea and we have fun, and I think we really may be friends, with the patriots sweatshirt and the bountiful baked goods, and the convenience of living so close by.

So I skipped the run, and the post (s) remain unfinished and my fifth round of IRS documents are not due until tomorrow at noon, plus I haven’t showered (remember the not run) and I haven’t unpacked so I am a bit frozen with possible activities. I decide the only answer is to head to Party City to compound my Halloween woe.

In Florida we went to Target. Here I will use the Target picture that I was planning to integrate into the Good Buy post .

Leo on pillows in a color that  only looks good against just the right shade of blue. Please do not attempt to use this color without proper adult supervision.
Leo on pillows in a color that only looks good against just the right shade of blue. Please do not attempt to use this color without proper adult supervision.

So Leo wanted to be a penguin and Oliver wanted to be Chewbacca and it has taken me 4 years to admit that I am the only one who cares about costumes and I care about them in the way a rabid sports fan cares about her team…they can bring me so much pain when they arent right and only just a tiny bit of pleasure.

So time is tight and ideas of crafters felt and glue guns and gasp, hand sewing are out. Why don’t they just sell a brown fur suit that can be a monkey, or a dog, or a wearwolf, or a chewbacca, but Target was never going to deliver this and I thought I had lucked out with the screen printed minecraft block head cardboard box masks so we could at least use the kids real clothes and it could represent something they really truly cared about and we were close enough to having that happen that we had them in our cart. The kids found the skylanders giants costumes though and so I was twice screwed. No penguin. And no block head.

If you don’t know skylanders giants a. consider yourself lucky and b. it is perhaps from a cartoon but defintely from a wii game. My Shelburbia warning system is at full red alert.

Is the costume mass produced: YES
Is it made of flammable material: YES
Probably by child labor: YES
Does it represent a cultural symbol: YES
Of a video game: YES
Do these characters have weapons: YES
Is the costume itself so crappily made as to be falling apart before we leave the store and create a full on crying fit in 2/3 family members: YES
Will it twist and mistfit to continue the crying fit through each time the costume is donned: YES
Is it so thin that without underlayerment the Vermont kids will turn into frozen skylanders: YES

Ladies and Gentlemen….a perfect score.

So the only fix for spending too much money on crappy storebought costumes? Borrow from friends? Get crafting? Amateurs. Head to an even more expensive store to buy costumes you like better but the kids will never put on because did you see the perfect score on the other costumes? Bonus points for neither set of costumes being returnable.

So I leave Party City (was iParty too virtual? Was Party Town too close to a really really funny Starz show?) $200 poorer with 3 store bought costumes…all of which require modification.

The only smart thing I did all day was finish this post before I began the frustrating act of modifying costumes that my kids don’t even want in the first place. I’m not a total sucker. Except that I am.

Pretty sure this was definition 2 of Madturbation.

How to get me to give you money.

What do I do? I mostly crush dreams, and sometimes throw a bit of my own money in to go down with the ship. I am an angel investor in Vermont, and this is part of the story.

Someone has a seed of an idea. That person talks to a friend or a colleague about it. Together they sketch out a more complete vision of the project, product, or program. Its all pro right now, except for the most part the team is made of amateurs.

They put together something, a pitch deck or a pilot program. They begin testing and iterating. So It is better and more clear than it was before. Also more clear? Their needs. Time, advice, equipment, space CASH. These are the early days. Days of possibilities.

So these two take the idea into the world to get feedback and support. This is casual. They talk to friends and family, build out a prototype, and carry it or images of it around with them. If they live in Vermont they might get to the point where they take it to a non profit who helps incubate business ideas, or the economic development office, or our friendly accessible local venture firm. Or just a friend of a friend of mine. If, like most emerging enterprises, you have an incomplete team, an underdeveloped marketing scheme, a smaller than necessary distribution funnel, or are not in fact poised to immediately make money, they get sent to me.

I am a VERY common first  or second step in this area. I have hosted hundreds of pitch meetings. Although hosted makes it sound as if I have planned them. This is rarely the case. Usually I am the crochety guest. You would imagine that by now I have a format that I follow, or even another person in the room, but it is usually just me. At my conference table, my dining table, a restaurant table. So the table is a constant.

These people are new at this. Maybe even new to one another. They don’t know what to expect from me, except someone told them to meet me, and now they are meeting with me. At a table some where.

So here we are. I am early, because I can’t not be early. To their credit they are usually early also. I say hello, ask them how they found me (who I should plotting my revenge on.)  It is almost always someone more formal and organized, like a VC firm, who punted to me because these folks are no where near venture ready.  So after I have my target I tell them I won’t give them money.  Just to save them time on the pitch. They laugh. I am probably not kidding, but we go ahead with the pitch anyways. By saying this I am hoping both to help them relax and decrease the chances I will write a check purely out of a sympathetic urge. Sometimes they say they are only looking for advice and then I know they are lying, except in the case of that one guy who seems to genuinely take pride in how many times we have met without me giving him money and in the end his weird reverse psychology is working and I am shoving a check at him.)

Now I tell them that I am completely unqualified to provide any help. I remind them that I have between 4-10 failed businesses to my name depending on how you count, so their best move might just be to disregard everything I say. So far no one has left so I try again, telling them that I will likely be mean at the meeting. The more of these I do the meaner I get. I do try to be funny mean instead of just mean mean, but that is probably in the ears of the beholder.

They have a pitch deck. What is a pitch deck? Well ideally it is a simple explanation of the background of the team, the problem they will be solving, the program or product that will solve it, what the competitive landscape is, what differentiates them from the competition, how they will build and test the thing, how they will identify their audience and turn them into customers and how the money that they bring in from their customers will be more than the money they are spending. And how that money will grown and be scalable.

Easy enough, right? But it requires a fair amount of extrapolation (or bullshit) because some amount of this has not been done or they wouldn’t be in a room with me.

If they are designers the deck itself is the project and it looks great.  Lately that means clean and white. If they are product people the idea is good, it probably has a name, but they likely have fundamental confusion between a product and a business . The branders know their audience, have a tagline, and usually an excellent logo. The solution folks have the “competitive landscape” and “minimal viable product” portions of the pitch nailed with fewer and fewer details as things progress. The biz guys always have huge and deep theoreticals which are too small to read from the chair. And almost always green with plenty of acronyms.

What do all of the pitches have in common? Totally unrealistic expense numbers (if they have expenses enumerated at all), the fact that they used “conservative estimates” (of the 80 billion moms on planet earth only .1% need to use our product for us to become quadrillionaires (which means I guess that the .1% is the conservative number), and the fact that they used too little orange.

That is a tip I give freely. Use more orange. People like orange.

What else might be wrong? They may have poured too much of their time and capital into it or too little. Both tricky. Too much and there is usually a sort of “you owe it to me to fund this” vibe. Which doesn’t work well for me. Too little and it is clearly how easy it will be for them to walk away unscathed. If I am going to take a risk on them they need to be taking a risk as well.

They often have the wrong ask in mind.  For non profits they can look back at past gifts and know how to target their ask. With angels it is tough to know. Even if we are registered on angel list the amount of the gift is not listed. I have given between $1,000 and $150,000 in individual checks to other people’s ventures. So asking me for $500 may feel like a slam dunk but it is really a waste of time. Anyone who asks me for $500,000 is way off. Anyone who asks a VC firm for $100,000 is way off in the other direction. If you are asking for that little their return will be proportionately small. That is an even bigger waste of time.

The most interesting to me is the group who finishes their pitch deck and then doesn’t pitch. Ideally you will go through the deck and then ask me for feedback on the product, the roll out, something. Ask if I agree with your target audience? If I tell you (and I will) that I care about how this exact idea is going to get money back into vermont focus on that.  But be careful…you need to be that most elusive thing…sustainable, and if you are reinvesting too much in the community you are not maximizing your chance to succeed. Says the pot to the kettle.

So I’ve interjected enough now so you’ve taken my temperature, adjusted things to sound a little more earthy crunchy than you would for a banker. You can tell I am not big on systems, so you emphasize how things will be nimble and responsive (for that banker you’d want to highlight checks and balances without redundancies) you need to show me you know your audience for the pitch to convince me you will know your audience for your business.

If you have any inside connections, a partnership with an established company, a media economy of scale, you should have those in there. Whatever makes you not just the idea guy is good.

Years ago my friend told me that he values the idea part of the company at 10%, it seemed low to me. We met for lunch again recently and re-evaluated. The idea is worth 2%. At most. A crappy idea with a streamlined build out and some sort of connection for distribution is much more likely to succeed than the best idea in the world that my eight year old has.

So now you do the ask. Its the hardest part. What are you looking for overall? And from me? What will this first in investment allow you to do? What is there that ONLY cash allows. No in kind, no sweat equity, no college roomate coding late at night.

Now what?

1. I give you what you ask for. Try not to look surprised. That makes all of us look like assholes.

2. I give you more than you ask for. Don’t say no. That makes me look like an asshole.

3. I give you less than you ask for with a specific direction. I want you to use this money to pay this professional person to investigate the legalities of x, write code for the mvp on such and such a platform, run a split test on your name idea v. my name idea.

4. I give you nothing.

This is when its good to have a fall back. I’ve said no to giving you money before we started. That should take the sting out of the second no. But what else can I do for you? Even though I have sat at this (these?) table(s) many many times I still want to feel helpful. I want to be an insider and a part of the start up team. I imagine I am not the only angel that feels this way. So what else do you need? Conference space? Introductions? Advice on a first media buy? I agree that cash is like oxygen and you should NEVER dilute your ask with these other possibilities until the money answer is a no.

Then try to keep me on the hook.

Maybe I will write you a check the next time.

Just don’t call me about it.








First In and Out

Which game show is it where you have to identify mashups of familiar phrases? Like Easier said than done is good. Easier said than done. Done is good. Now that I’ve insulted your intelligence by breaking down my post title I can go back to insulting myself…my real forte.

So I was going to try to write around the particulars so as not to upset my friends at Burlington City Arts, but I am pretty sure I am the only jackass in this story. I tell it to try to learn something.

4th floor gallery
4th floor gallery

For almost a decade Doreen Kraft and I have had lunch once a quarter or so to shoot the shit (my phrase) review the local arts scene and very occasionally tap into me as a supporter of BCA. She knows (because I tell her) that I prefer to support the arts by buying art, that my gifts to NPOs are smaller than they once were because I am focusing on social ventures, and that I don’t actually have that much money. Nonetheless we generally enjoy lunch, she often has an incredible partnership story to share and I can make her laugh.

A few times we get into it a little more deeply and we talk about pieces of their mission that I feel could be boosted by programs or events. Like most small scale donors I talk about my particular areas of interest, and like most skilled fundraisers she indulges me in highlighting the importance of my ideas. One of the things I wish for in our community is to cultivate the next generation of art colletors. If they become supporters of the visual arts scene in general that is a positive byproduct. But what I really want is for Shelburbian moms to take their pottery barn budget and use 2/3 of it on original artwork. Selected correctly this will enhance their homes and lives in a way no mass produced ceramic cornucopia can. AND the artist might well be able to support him/herself by, you know, making art. Something that, despite the “my 1st grader could have made that” attitude, most of us never even dream of doing.

Your first grader is a: a child who has yet to lose his imagination, b: someone who through the school system and various enriching activites actually devotes time each week to looking at, talking about, and making art, and c: actually has an art teacher. Put your kids at home without materials, prompts and instructions and you are probably back to stick figures, but I digress. (Don’t cut art, it allows them to see the world differently, shape imaginary outcomes, and let off frustration in a completely beneficial way.)

BCA has plenty of great educational programs, but my interest is in making Burlington a city where it is viable to live as an artist. The ways that an art infused city enhance our daily lives exist below your general radar I would expect, but they are everywhere. Not just public art, but temporary expression, what the bathroom looks like at Lucky Next Door, signage, painted junction boxes, and tumbled marble from an international sculptor gathering decades ago hidden in the overgrowth of your walking path.

So 2 years ago we talked about a CSA, community supported art share, where members could pay a super affordable price, attend opening events and select art off the wall for their homes. The logistics were tricky, would BCA commission the work, or go into backstock. Would they be limited edition? Would the selection be first come first served? How broad did it need to be to appeal to most of the share members tastes? Could taste shaping be baked into the events? I was part of these early discussions.

Then I stopped taking phone calls. This might sound familiar to those of you who have tried to reach me. There are about 12 people I will speak to on the phone in this world and I’m pretty sure none of them are work- like. Well, I talk to my accountant right now because of the audit, and my money manager’s manager because of ML bizarre (bizarre only to me obviously, almost everyone else agrees that sending account numbers, passwords and wire details through email is dumb) security laws, but even with those two I think my phone people fit in the bakers dozen.

So Doreen has been calling me for a year, while I put off lunch due to a mix of depression and other activities. A few months ago she took to emailing me, so I actually answered. She would ask to break bread to talk about the gallery and catch up and I would reply with gibberish about properties and activities. Basically I was an asshole. But I figured that wouldn’t really effect me. If people want money or ideas or both from me they can work with my quirks and schedule.

So yesterday I get a long lovely email with a bunch of attachments crediting my idea, telling me they have moved forward, inviting me to the opening, crediting me with connecting her with some of the money that they have received, and asking me to be a founding member. Pretty good formula. Appreciation, credit, more credit, optimism, invitation. And me? Panties = bunched.

In reply to Doreen’s last ditch email (last ditch because she has been trying to see and or talk to me for a very long time) I bang out a two sentences…I’m not giving you money I’ll try to make the opening. (Steve and I have a standing Thursday sitter, so this is super do-able, but first I seem to need to act out a bit.) Then I text my friend Kerri who is standing working her butt off in the gallery instead of putting her kids to bed. I tell her I think BCA has mishandled me.

Then after I do both of those things I stop and think. Actually I am not yet thinking. I am still feeling the full on bunch of the panties.

Steve and I stand at the sink washing up after dinner. He does the washing I rant next to him, slamming down pots almost close enough for him to reach. “So I gave them this idea, and then I get invited to the opening the day before.” The suds from the dishes smell good. I lean in a little closer. Steve continues his rinsing. “So you never returned her call?” “No!” I answer in outrage, “it was a CALL!” “mmm hmmm.” “I think that if someone wants something from me, ideas, money, connections, the least they can do is NOT CALL ME.” “But then she emailed” Steve reviewed. “Yes, she emailed, but she didn’t tell me why she was emailing, she said she wanted to have lunch and talk about some things, I didn’t know it was the idea I cared about.” “OK, fine, but do you always have to be so rigid about phone calls?” Standing there I am thinking that I obviously have to be MORE rigid about phone calls if people are still calling me. I have rerecorded my home message leaving the cell number, but I am pretty sure I need to somehow disconnect the cell message telling people text or nothing. I am lost in this train for a minute, so thrilled that iOS 7 agrees with me and allows me to answer and incoming call with a text reply. Those are the best. I mean, like, 8 years late, but still. Steve has not lost his train of thought. ‘Do you really think, you can be angry when someone made every reasonable effort to contact you, and, you just didn’t answer, I’m not trying to challenge you…” I mean he was OBVIOUSLY trying to challenge me, and although I feel myself digging in to the whole phone thing it is at the same time that I am letting go of the gallery opening. Scraps of conversation are coming back to me, Kerri telling me about her progress. Sarah mentioning it at her studio. I have blocked them out. They didn’t integrate into whatever I was focused at the time. I realize that what I am really upset about is that my checking in and out of things whenever I want has left me out of the loop on this one. I’m not sure I would have given the money, or if I would have even had any ideas to make the event better (fuck that I’m SURE I would have had the best possible ideas in my opinion.)


So this is a long, public apology to Doreen and Kerri, who while trying to manage 1,000 projects also had to deal with a grumpy friend/donor with particular odd communication rules that also happen to be a moving target.

It is also something about IP and founding, and first in stuff. As much as I work on letting go of attachments (or I used to, and imagine I will again someday (see how unattached I am to that practice? go me)) I still have a tether of connection to my ideas and how they are executed. This is dangerous. I need to give them freely or not at all. If I want to manage the way an idea comes to life I should not share it. Thats on me. This idea was always best for BCA, even if the details are not as I would have chosen them (and I don’t even know maybe every detail is how I would have done it.))

These questions have been in my mind lately as contracts come across my desk that limit future consulting work because of a current gig, (non competes) and I write checks to help fund start ups and then try to direct my money towards the exact instrument that I want explored. I seem to want it both ways. No limits on me, but with overreaching oversight. I want this imbalance to be negotiated without contract or paperwork. I want to be first in, first out, and with the outcome I imagine but don’t help execute. Seems like my recipe is a bit off. It might need some tweaking.I’m pretty sure non competes in Burlington Vermont are utter bullshit though, just saying.

If anyone is free tonight in the BTV area come join me celebrating the 4th floor gallery at City Arts…I’ll be the one with the egg on my face.

Heads up, shut down.

It was a very social weekend, he tells me. I read into this and try to pry more details out of him. This friend keeps things to himself effortlessly, so this is about as effective as asking Bellichick for an injury update. (Can any of you tell me how I have been a rabid Patriots fan for 20 years and have not learned how to spell our head coaches name? No?) There is a bit of something there though, so I work on the nail with my screwdriver, unequipped to get the job done. He sums up his non story like this: “I think I might just have my head up these days.”

I know what he means.

There are times when we are aware and everything feels possible. Our town delights us with new restaurants, the act of mulching around a bush feels like a gift to the neighborhood, the people sitting in the cafe look engaged and intelligent, each a possible friend or colleague. Posters show concerts, pop up dinners, pumpkin patches, and fundraising runs. I want in on each of them.

Quick meetings leave to do lists that are evenly distributed, easily accomplished and with community wide pay off.

The row of closed doors don’t represent lives unled, but lives yet to be led. Knock and enter, or just barge in. See what is back there, get messy with it and make something. These are the good days, the heads up days.

Then in a phone call the I come crashing down to earth. The accountant has finally gotten through to the IRS after the shut down and amongst other unsavory details informs me that the interest meter was running during the shut down. I want to howl with the unfairness of it all. I took a risk, tried to create a product to help families, poured time and money into it. The worst part of the audit has been revisiting my efforts. I really tried to make Marble Jar work. Conferences, sponsorships, blogger outreach, many many marketing efforts and product refinement. So many. Now, not only did I lose over $100,000, but the IRS is claiming it was not a business but a hobby. If I can’t prove that it is a business by providing contracts (bank statements and Amex statements don’t count) for each of my expenses then not only will I owe $16,000 for 2011 but will have to go back to 2010 and ahead to 2012, and there will be interest and penalties to pay. This is after I paid over $250,000 in taxes. And for fucks sake this is the worst hobby on earth.

When I quit things early it is a protective mechanism. Quitting is less painful than failing. But this research into 2011 puts me face to face with failure. A piece of me still believes that if I try hard enough I can do anything. I don’t want to disabuse myself of that idea. It is what makes me take risks, and believe in my kids. Its hard to nurture that belief when I revisit an above and beyond effort that failed so spectacularly that the IRS claims it was never a business venture at all.

I’ve got my nose to the door and my eye to the keyhole, but from the outside the reverse fisheye makes everything so small and far away.

Possible has turned to impossible, curiosity to my own kind of shut down. I wonder why any of us put ourselves out there.

We may want in, but staying out seems safer…it might just save us an audit.

It is easier to keep our heads down. I’m just not sure easier is better.

Possibilities, or dead ends?
Possibilities, or dead ends?

This doesn’t make cents

Here’s another sticky point about money. By its very nature it is taking us away from the present. Originally we all bartered. Chicken for wood, my help in construction for your cow, etc. skill and effort matted as much as luck. Then money came along to allow “fair trade” deferring what one party brings to the barter agreement.

I don’t quite know what I am saying, butit is something about being a giver v a taker. Where giving represents being generative, adding to our world in some way and the other is simply a consumer. In capitalism consumers have a vital role, and I often argue to myself that conscious consumerism is a generative act.

Since I am not a maker, adding to society means something more abstract. And I struggle with that. It’s not as simple as production. I use the word generation. But I struggle with all of it.

At my most philosophical I think that the enlightened state is the exact point between production and consumption. That is where living each day is the focus, we don’t rush forward. It is not my natural state. Maybe no ones?

I’m trying to change my mental picture from treading water to floating. You stay in the same spot. However one takes a hell of a lot more effort than the other.

Overheard at the gym

This is not what I see at the gym
This is not what I see at the gym

It took not one, not two, but three friends pressuring inviting me to work out this morning for me to make it to the gym. Because I was planning an 8:40 departure I had 2 full hours to sit in my pee bed and ring myself with various devices in order to play plenty of candy crush. Some people pay for new lives, some people cheat and set the clock on their phone a month ahead. In the true spirit of excess I just use my six iPads to rotate from one to the other as get stuck on a level. If you don’t know what I am talking about consider yourself very lucky.

As I drive to the gym I see the gas light. I remember seeing it yesterday, and (is this right?) the day before. I switch the display to miles to empty and it reads 2, and as I wrap my brain around that it switches to 0.

My first thought is one of elation. NO WORK OUT! I could be literally out of gas.

But it is pouring . So the walk to the gas station would be as bad as the exercise class. Maybe.

During the class I barely make it through the 30 seconds exercise 30 seconds rest, and get to the stretch portion where the ladies loll around on foam rollers. Most twisting into different positions to stretch out glutes, hammys, and other adorably nicknamed large muscles. I sit in proximity to the roller.

To my right a friend and friendly acquaintance are chatting about parenting. First of all I have tuned in late and don’t know the context of their conversation, second of all I have been working out, so my internal monologue is crowding out most of my ability to hear. It sounds like this. PHEW thats done. Now we don’t EVER HAVE TO WORK OUT AGAIN. Wow, I smell bad. Why are all exercise bottoms black?

Back in the stretching circle I hear a bit about her daughter crying. Then she says. “I just can’t let her fail.”

Despite making eye contact with a friend across the way and miming the universal sign for zipped lip I chime in. “But if we are all guaranteed to have a set amount of failure in the world, wouldn’t you rather her go through it now, when it teaches resilience, then later when the stakes are higher?” Or thats what I would have said if I had been sorted out. Instead I said “Isn’t it better to fail now than later?” “no.” She answers me emphatically. No. I can’t let her fail.

So I turn away, back to my mimed stretching and think about it for a minute. I wonder why I believe in some sort of conservation of failure. Its not like we have this predestined amount of trial and tabulation, and we can just move through it early in life and coast later. But we all fail some time. Really lots of times, and it takes practice.

Limiting the scope creep of failure, knowing that we are still lovable even if a friend ditches us, or that we can still become experts at something if we struggle with foreign language, or there is a point to running even if we don’t win the race. (Well I actually don’t believe the last one, but you get the idea.) Its better to do that when the stakes are low. That is why we emphasize process and effort and things within our control, not outcomes to children. And still there are winners to races, and one kid picked for the lead in the play. And that is OK. It is OK not to be invited to a party.

[Tweet theme=”basic-white”]That is why we emphasize process and effort and things within our control, not outcomes to children. @annawritesstuff[/Tweet]

Just yesterday Leo told me that Oliver spent all of recess alone because his one closest friend wasn’t in school. I asked Oliver how he felt about it. He said fine, he just walked around. I remember eating lunch in the band room, hiding in bathroom stalls. Despite some vicious and lonely times I have more friends than I can effectively spend time with now. It is all temporary this life of ours.

So it is time to stop stretching. Or stop pretending to stretch, and three of us decide to go get $8 smoothies. Mine turns out to be an $11 juice and it is almost comical. It takes 25 minutes for the little juice dude to prep our three juices and we could have fed a family of four on what we paid. A first world snack stop.

We catch up, talking about philanthropy and social ventures, and then my blog. Which people read and talk about even if they DONT COMMENT. I tell them about my private emails numbering almost 100 after the money post. Seriously people. Start talking about money. You all want to. I joke about putting standard disclaimers at the bottom of each post. “I think about Syria [insert current important global issue], I just don’t write about it” and “I don’t edit, its part of what you love about me. Ignore grammatical errors or stop reading.”

We check in about our afternoons and I tell them I am going back to bed to play candy crush. They know me well enough to no I am not joking, but they only get disturbed when I reveal that my bed has been peed on. (Not by me) We talk about pet problems and how I think putting down the obese, snoring, bed wetting, lumbering one eared cat would send the wrong message to my kid who still does a bit of bed wetting himself. You pee you die.

And thats it. Workout and juice is over. A perfect morning in Shelburbia. Off to crush some candy. We leave with a wave, and she calls out to me. “Don’t get in the pee bed. Don’t do it.”



 I think about Syria [insert current important global issue], I just don’t write about it.

 I don’t edit, its part of what you love about me. Ignore grammatical errors or stop reading.

Oh, and if you want to tell me something I pretty much always want to hear it but I suck at secrets. So maybe use a pseudonym. Or something.



More money thoughts

Sort of like the sex posts I’ve gotten tons of private responses to my money blog.

Thank you all for having this conversation with me.

The last post was a history of how I have money to share.

I’m pretty sure you could read the feelings of conflict in that story.

Fundamentally I feel really really lucky. A sense of luck, and honestly if you could take the edge of off the word, of entitlement, has been surrounding me as far back as I can remember.

Once again, to let my actions explain my mental state…

I don’t plan to leave my boys money. My mother may/will, and I hope I can be executor of those trusts, and save them for things like school, and housedownpayments. Even so it will effect their trajectory.

There might have been something to that 35 year old trust of my grandmothers.

I am a non conformist. Having money has, like my father, enabled me to live that way unchallenged. I am almost 40 and have spent in total 4 years of my life working for other people. One of them in a Harvard research lab where the head scientist had somehow literally and figuratively left the building, two of them as Ed of non profits accountable to boards who for the most part were simply happy to have me, and teaching, where as integration facilitator I made the plans and answered to no one. The principal wanted to pretend I didn’t exist, and when he balked I had the law and scary statistics on my side.

I don’t think I have ever called anyone my boss.

What if I had? Would I be thinner (more disciplined), happier?

I don’t know. There is no control group for me. But the bottom line is, I feel lucky, but don’t want to share this kind of luck with my kids.

Money changes everything.