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Nate Otto

About Nate Otto

I like to draw cities and little people. I am a regular contributor to Basecamp as an illustrator and an artist. I have pitched in since Basecamp was Spinfree.


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About five years ago I consciously willed an art career into existence. At that point I had been working a social services job for about five years. I initially took the job because it wasn’t specifically art related. It was a job I could feel good about — helping people with disabilities — but it wouldn’t tap my creative juices. I had learned many years before when I got a job doing graphic design that being creative at work drained my creative life bars during my down time. This social services job would leave me with enough creative energy to work on my art when I got home, but in reality that wasn’t really happening. Furthermore, the job itself was becoming a frustrating dead end. I had learned that working in a large organization with seven direct bosses wasn’t an environment in which I would thrive. What would my next move be? I was grown up and competent. I felt as though I could do pretty much anything.



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If there was a buddy cop movie starring the Geico gecko and the Aflac duck, I’m pretty sure it would outperform “Edge of Tomorrow” at the box office.

We love our anthropomorphized branding mascots. Shortly after Basecamp hatched its own such character, I was watching a big event on TV, and it seemed as though every product in every commercial had sprouted arms and legs. I guess we are part of the zeitgeist.

While I would love to take credit for inventing our Basecamp creature because he came out of the tip of my Micron, the fact is Jason asked me to create it, and it’s pretty hard to go wrong by adding humanoid features to the Basecamp logo. The results are bound to be adorable. Shawnimals had made a similar character months before with the Happy Sherpa, and our design intern this summer, Julia, also made a nice version. That said, I’m proud of the character I helped create, and I’m glad to see it gain momentum. What started as an experiment seems to have taken hold.

At Basecamp, our marketing is more intuitive than contrived. We don’t have dedicated marketing or sales staff. We pay attention to data but it doesn’t own us (take that Noah). I think the philosophy has been that the best marketing is a superior product. Basecamp sells itself, but it doesn’t hurt to have something cool to print on T-shirts. That is where this mascot comes into play. Internally we have been calling it “Basecampy,” and I heard someone call it “Mr. Basecamp” the other day. Let it be known, however, that it is genderless. It reproduces through binary fission. A creation myth is in the works. Basecampy may stick as the name, but we are open for suggestions. Leave your thoughts in the comments.

Extra Drawings

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For the last ten months at Basecamp I have been the guy that draws stuff. After making occasional contributions at 37signals over the years, they tapped me to make hand drawn images for the Basecamp marketing site that first appeared in February. Since then my drawings have crept into the app itself, into email blasts, onto banners at Pitchfork, all up in The Distance, plastered on the walls of the office, and into several employee’s avatars. We came up with a creative contract that allows me time to work on my other career as an artist while still providing substantial input at Basecamp.


Drawing Trouble

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One of the fun aspects of illustrating for the new marketing site is getting assignments from Jamie, Jason, and Mig. One of my favorite briefs I got was “can you illustrate browser trouble?”

Upon getting art requests, I usually search to see if there’s a standardized image for the concept. In this case I didn’t find any imagery that rose to the level of iconic, or was particularly interesting or clear. I opted to start from scratch.

Hmmm, browser trouble

Broken windows, bugs, injuries, cracked screens, dizzy people? I drew a page of visual brainstorms and posted it on our Basecamp project.

Whoever assigns me a drawing—in this case, Jamie—reviews my explorations and then ask me to flesh out one of the directions. Jamie liked the guy with the computer head and suggested that there be a browser window with a frown face.

I drew up another page with color.

With that, Jamie got back to me with “Awesome.”

I waited to see how the image would be implemented. Working with the Basecamp design team is great for me because I’m not particularly strong in Photoshop or Illustrator—those guys are all ninjas. I like to draw, and that is how my time is spent most efficiently.

Usually I have no idea how the images are going to be used until they are implemented live on the website, which is fine by me. I like the surprise of finding a fully rendered web page with my drawings.

Hopefully it is a page you will never have to find.

Million Dollar Art

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I have always struggled with the dark art of pricing artwork. Weird magic is involved. I have seen an interested buyer lose interest when I quoted a price that was too low. Oops, I mean… All of a sudden the aura of the work was gone. How could I be a serious artist if I was willing to sell for that price? Could it be that it certain cases, raising the price actually increases the demand?
I was talking about this recently with a friend and he told me an anecdote about a wine seller who had an overstock of a particular wine. When putting the wine on sale didn’t help it move, he greatly inflated the price and suddenly it began flying off the shelves. Does more expensive wine taste better? This Freakonomics podcast explores this question with surprising results. I thought my unsophisticated palette was to blame for the fact that I can’t tell the difference between five dollar and fifty dollar bottles of wine. Turns out I’m not alone. In blind taste tests, the experts may be just as clueless. I think wines with cool labels taste best.
I have discovered that there is something in economics called a Veblen Good, a luxury item for which price equates quality. Art can fit into this category. Economists in the house, please comment. My knowledge of the subject is confined to my recent Google history, but I’m happy it has a name.
At any rate I’m trying to make the best paintings I can. Below is a painting I recently completed. It can be yours for ONE MILLION DOLLARS.


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I made this drawing over the weekend while watching football on television, listening to an audiobook, and intermittently using my computer. Multitasking such as this is pretty common these days. Does anyone think that is a good thing?

Everyone Should Make a Painting

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Read that headline carefully. Note that I didn’t say everyone should start calling themselves artists and try to sell their paintings for thousands of dollars. I do, however, think the exercise of making a painting is a good one for all human beings.

Painting has been around almost as long as hunting and gathering, and there are very few activities that are so innate to our species. Resolving a painting is a puzzle, a maze, a riddle, a quest, all that. It is a process requiring a billion decisions. Want to try a great game? Put down that electronic device and pick up a brush. Get in touch with your human part. Even Michael Jackson’s former pet chimp, Bubbles, is doing it. Elephants do it. It’s a genus thing.

Getting started, the gathering part

You are going to need some paint, some instruments to paint with, and an object to paint on. Got a $100 bucks? That should be enough to get you started.
First off, don’t use really crappy paint. It is not impossible, but it is significantly harder to make a good painting with student grade paint. Get a set with eight to ten colors. This will cost you 35-50 bucks. Here’s one.
(Note: I’m spreading the links around between Blick, Utrecht, Amazon, and Cheap Joes. All are good options, as is Mom and Pop’s down the street. Look for sales.)
Next, get some brushes. Brushes can be crazy expensive. You don’t need fancy sable brushes to get started, but you shouldn’t get kid stuff either. Get a decent synthetic set with a variety of shapes: 20 – 30 bucks. I like long handles because they can also be used to kill vampires.
Get something to paint on. Canvas works. Do you have your own woodshop and like to make things ten times more complicated than they need to be? No, then don’t stretch your own canvas. There are some great options at the store. Get a few canvasses so you can make mistakes. One of my former instructors told me that you always make your best paintings on shitty canvasses, and I have found that to be true wisdom.
Rig up an easel. You can paint on a tabletop or on the floor, but I think it is really important to learn how to paint from a vertical position. If you have the option, hanging a canvas on the wall and working from there is preferable to working horizontally on a table. There are Easels that cost as much as a ‘04 Lexus ES300. You don’t need that one. Start out with a $20 tabletop easel. If you have more room and this pursuit is going to be lasting, get a real easel. Later on you can store it with the treadmill.
One more thing. You will also need a palette and a cup. Paper towels and newspaper may also be useful. For a palette I recommend a sturdy, disposable, plastic plate. Anything non-porous and solid will do. Glass, marble, old electronics, sealed cardboard, or even another painting will work as a palette. For a cup use something substantial enough in size and stable enough in shape to hold brushes. Old soup cans work. So do plastic beer cups. I have even sawed off the top of a Gatorade bottle and used that. This cup will hold dirty paint water. Choose a cup that you will never want to drink out of again. You don’t want to drink dirty paint water.

Getting started, the hunting part

Let’s paint. If you are painting on the counter with a tabletop easel, put some newspaper or something else down so you don’t ruin the counter, you idiot. Also, take off that expensive suit. Next, put the blank canvas on the easel, raise it to a comfortable height, and take in the intimidating blankness of it all.
Now what? Well you haven’t finished setting up yet. You are going to have to find a place to set some stuff down. Find a little side table, or a stool, if you aren’t already working from a table, and put it on the right or left side of the canvas, depending on your dominant hand. Now, go fill the cup 72% of the way with water and set it on your table. Also find some space for your palette and some tubes of paint. Take out those brushes and drop two of them, bristles first, into the water.
You are ready to paint.

A few things…


Deconstructing the Cityscape

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Red Cloudy by Nate Otto

About two years ago I was approached by Jason to make some art on the 37signals office walls. Around that time I was also beginning to delve into the notion of cityscapes. The first wall I did was an extension of an idea I doodled on a pizza box with a Sharpie marker.
In the time since I have been back to update the blackboards at the office several times and I have explored the cityscape idea further on my own. I have drawn and painted imaginary cities as cross-sections, from above, from every direction at the same time, quick and dirty, slow and precise, cloudy, vacant, abstracted, cartoonized, covered in streets that are like noodles, blanketed in billboards, brightly colored, monochromatic, big, small, and on and on. Each city is a new discovery to explore from whichever vantage I choose, and I’ve only just begun.
One of the things I love about being a “fine” artist is the freedom. When I’m starting a new painting or drawing, I am free to push the idea wherever it takes me. The onus is on me to take the ideas further, and venture out of my comfort zone. There have been so many times that I’ve gotten halfway done with a piece and thought to myself that this particular piece was a failure and amounted to nothing more than a bunch of wasted time and supplies, but then somehow, as if by magic, that work turns a corner and becomes my new all-time favorite. This transformation amazes me every time and it bolsters my often fragile confidence.
I have been an artist for a long time and I have gone through many phases. For years I exclusively did large abstract oil paintings, and there were times when I would draw nothing but cartoons. These past lives would seem to have very little to do with my current work, but the lessons learned from past experiences are not wasted. Instead, the skills and knowledge gained from being an abstract expressionist and in-class doodler will inform a new drawing. These are the tools I can use to build a brand new city, one that I never could have imagined before my hand began making the marks.

Color City
Dark Hill City