EDITOR'S NOTE: this article on Douglas Dollars follows on from our interview with Mike Merrill, the man who sold shares in himself. MONTAG hasn't spoken to Douglas, but he shared all the information about his investments freely online. So, we created the story of Douglas Dollars' life by looking at his his money; as opposed to Mike Merrill, who is letting money create his life story.


It's easy to judge people on their first impressions. In the case of the semi-elusive Douglas Dollars, the first impression made by the header "I Always Win," at dougalwayswins.biz, followed by an unsmiling illustrated portrait, creates an impression of arrogance, competitiveness, certainty, and seriousness.

Douglas is the self-proclaimed "2nd-Greatest Investor in Interesting Projects" in North America, but this title would be hard to verify, given the vagueness of "interesting projects." Surely some of the investors in any of the projects listed on Wikipedia's list of the highest funded crowdfunding projects have made larger donations.

Then again, perhaps "greatest" doesn't have to mean the largest dollar amount. When trying to find out who exactly this Douglas Dollars fellow is based on his investments, we found out a lot of things about his preferences, hobbies, taste in media, arts, and culture. Judging someone and trying to determine their personality and what makes them tick based on how they spend their money isn't hard in general, but Douglas Dollars makes it extremely easy to paint a portrait with his paper trail.

And despite the unfriendly appearance of his website, Douglas actually does seem pretty great.

Selected investments in the first five years, 2008 - 2013

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His first donation listed chronologically is a January 2008 investment in a now-defunct art project that involved paying €30 which would go to Palestinian NGOs supporting infrastructure, in exchange for someone spray painting a message of love on the Palestinian side of the West Bank barrier. Douglas chose the message "Morrissey Knows Best."

A two year gap follows this initial investment, and his second is in March of 2010, a donation to a Kickstarter campaign for Open Goldberg Variations, a new score and recording of Bach intended for the public domain. The project was fully funded and you can now find free downloads of Kimiko Ishizaka's performance, as well as full scores including a braille edition at opengoldbergvariations.org and on the Internet Archive.

In August 2011, he bought stock in Mike Merrill. He currently holds the third-highest number of shares and number of dollars invested, and has a long trading history within Merrill's shareholder community. This is how we were first introduced to Douglas Dollars. Merrill wrote, "He’s actually a great example of the greatest power of the KmikeyM project. It acts as a beacon of like-minded people... I want to find all the Douglas Dollarses in the world!"

Finding it fascinating that although these two men have never met offline, yet negotiated this strange relationship through Mike's self-corporatization and Douglas' interest in the intersection of art and capitalism, we looked through Mr. Dollars' other investments in the early years to find more of these types of projects, and were not disappointed.

Capitalsm Works For Me! by Steve Lambert

In August 2011, Douglas Dollars backed a Kickstarter project called "Make Capitalism Work For Me," by the artist Steve Lambert. The project was a large-scale art installation of a 9 foot tall and 20 foot long light-up sign bearing the words "CAPITALISM works for me!" and two scoreboards on either side reading "True" and "False." The sign was accompanied by a podium where people could walk up and cast their votes about whether the statement was true for them or not. It was fully funded, making almost $7,500 over the initial goal of $9,500, and ended up being built and taken on tour of the United States, even being set up amongst the flashing lights of Times Square.

The next art project exploring capitalism and commerce that Douglas Dollars backed was The Garage Sale Documentary by Jared Whitham. Fully funded over its goal of $10,000, you can now pay $2.99 to rent or $11.11 to buy it online. Whitham calls garage sales, "The Last Free American Market Place" and the documentary itself "The first important social exploration of the American Garage Sale." He writes by way of description, "In times of financial crisis, increasing numbers of people gather supporting each other at this great American pastime. Money stays in town. Dreams are made, bills are paid and treasures are found. Cultural boundaries are broken, supernatural events take place and you finally meet your neighbor."

This focus, in the two projects listed above, on how communities form through acts of public art and the conditions of life in late capitalism, is right on the money for Douglas Dollars. And if you've ever walked around Edmonton, Canada, and found yourself compelled to take a "High Five Test," he may have had something to do with that particular intervention.

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In 2012, he was one of the backers of the first XOXO Festival, an art and technology festival in Portland that continued annually for the next four years.

Lest you think this selection of investments in the early years of the Douglas Dollars Charitable Trust is evidence of whimsy, one of the most interesting investments of this time period was in Tikker, a watch that counts down the seconds of your life. The manufacturers calculate your life expectancy according to "a simple calculation and questionnaire" (i.e. most likely an actuarial table), with the philosophical implication being that if we are made constantly aware of our fleeting mortality, we may make better choices and the world will be a better place. "All we have to do is learn how to cherish the time and the life that we have been given, to honor it, suck the marrow from it, seize the day and follow our hearts. And the best way to do this is to realize that seconds, days and years are passing never to come again." Backed on Kickstarter in November 2013 to the tune of $98,000 (their original goal was only 25K!) the Tikker became a real product that you can buy today for $59.99 on mytikker.com.

2013 - 2017

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Through his very active middle years of investing, Douglas Dollars backed a number of creative projects, often by many of the same makers or with interesting similarities. Several documentaries and video projects make the list, such as Pier Kids: The Life, about the lives of homeless gay and transgender youth. There are a number of tabletop and card games, including Werewolf and Secret Hitler, both by Max Temkin, the co-creator of Cards Against Humanity. He also backed Temkin's zine project, Maxistentialism, and a card game by the team behind the humor site Rooster Teeth called Million Dollars, But..., which asks what you would do for a million bucks, putting your "morals, imagination, and friendships to the test," and was backed for $1.3 million.

There are also numerous projects by the Maximum Fun podcasting network's Jesse Thorn, including One Thousand Free Ice Cream Cones (The Movie), which is exactly what it sounds like: Jesse Thorn and Jordan Morris attempting to distribute one thousand ice cream cones and making a movie of it. "Why? Because it's summer, and everyone loves ice cream, and it would be fun to buy a thousand people ice cream. We're not changing the world here, there will be no TED talk, we promise. We just think it would be a great thing to do with a weekend of our lives."

It's this philosophy, of not changing the whole world, but having a fun thing to do, spreading joy, and supporting the media makers that make the kind of media that you want to see more of in the world, that runs through Douglas Dollars' investment history.

Odd pieces of hardware like the C & C bottle cutter and the Pon Pin reveal a love of DIY projects and interior design. A few cookbooks and a simple syrup making kit reveal a love of good food and craft cocktails (if the backing of a grilled cheese food truck that you can still find roaming the streets of San Francisco wasn't enough).

All of the above paint a picture of a well-rounded, fun-loving individual; someone who can throw a really nice board game evening, with dinner and discussions of current events and social issues, without getting too serious – a very different man than is implied by the tenor of the site that lists these interests!

If you haven't already fallen in love with Douglas Dollars and want to be his friend, read on.

2017 and Beyond

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He lists his most recent, and seemingly largest, investments at the top of his site, out of chronological order, and it appears that his investment strategy has shifted from the fun to the purely philanthropic.

The first link is to DonorsChoose.org, which provides funding for public schools. According to the site, he has supported over 2,000 students across the US by backing 21 different projects, including an initiative to buy calculators for low-income students in Pennsylvania, providing engaging learning materials to ESL students in Nevada, and furnishing a classroom in a very high poverty school district in New York with a comfortable rug for third graders to sit on for free reading time.

Second is charity: water, where the description for Doug's Ultimate Water Party reads: "I want you to have the ultimate brag. We’re going to give FOUR HUNDRED PEOPLE access to clean water if you chip in here. This means 400 humans no longer ingesting parasites from water that looks like chocolate milk. Forever. Because of you. How much do I need from you? $35, or whatever you want to share." Under "Emotional Leverage," he writes: "you could consider it a gift of $35 for my 35th year, but really I’m just trying to make you look cool, as usual." For this project, Douglas Dollars matched all the donations of his friends with his own contribution, and Google matched the cumulative donations for a total of $12,000.

The charity:water campaign ended in September of 2017, and since then he hasn't updated dougalwayswins.biz, but has revealed his 2018 goals on a different site, suitably titled mygoals.website.

"In addition to several charitable, financial, and personal goals,
I have some public goals for 2018
Gimme a shout if you think you can help any of these along.
GOAL: Get a cat or dog 😺 / 🐶
GOAL: Learn some Spanish, Mandarin, or Japanese
GOAL: Step on a beach or two
GOAL: Print a book of 60 photos, my five favorite per month 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷 📷📷📷📷📷"

What we've learned

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Douglas Dollars is a force for good in the world.

Based on what we can learn about him purely by how he chooses to spend his money, he's a pretty cool guy, with good taste in media and art.

What Mike Merrill wrote about wanting to find "all the Douglas Dollarses of the world!" is true for us as well, but unfortunately for humanity, there may not be too many people like Douglas Dollars in the world.

He's a special person, and we can't wait to see where his drive for supporting artists, good causes, and questions of how to change the world for the better with his dollar-power take him. Viva la Doug!

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