How to succeed at being a graffiti artist
Building your product, getting up, be recognized and exit
Here is a recent presentation I gave at an unconference event. I don’t paint publicly today, but it’s a fascinating space so I presented on “how to succeed at being a graffiti artist”.
Thank you all for joining this session today! I’m going to be presenting on a topic slightly different than the originally proposed title “How to paint graffiti and everything you didn't know about street art.” A better title would be how to succeed at being a graffiti artist, y-combinator style. This is going to be a very deep dive into the career of a hypothetical graffiti artist, of which I largely don’t think exist. As a humorous way of synthesizing all the great sessions we have had, I’m going to share the parallels between graffiti artists' careers and growing a startup.
As a graffiti artist, you need to design your pieces and build your product, then you need to get sales, market your product to the masses, hire to expand your crew, and finally consider an exit strategy. Following this advice could lead you to glory and riches, but much more likely is you’ll end up in jail and jaded about the world.
A bit of background here - I became passionate about street art growing up in San Francisco, at the age of 8 - where I was regularly seeing abandoned shop faces and parking lots with big colorful murals. My brother at the time was himself painting graffiti and had a cache of spray cans that I remember seeing. As I got older, I found a job at a retail art store, and from there began my juvenile spray painting. Through high school, I got into a bit of trouble and was expelled - which did not deter me from continuing my nighttime pursuits of scaling buildings. Eventually, after college, I moved to China, where I was part of a local graffiti crew, and ironically also where I met my cofounder (not related to the graffiti). Eventually, I stopped painting publicly, but ended up making software related projects to help graffiti artists evade the police, and finally started indexing all the street art online through Instagram and Flickr. This project interestingly received some grants/funding and became indirectly my foray to getting funding in startups.
So starting off!
First, let's start with PRODUCT. All graffiti artists have a product. Of course, you have tools and resources you use, but the product is what you create. So for a graffiti artist, letter forms and characters are everything. Graffiti has changed a lot over the years - for one, it started in the north east, some say Philadelphia, others say New York - but essentially, it started in a concentrated area in the late 70s. If you want, you can watch a fascinating documentary that captures this period in a movie called Style Wars, which I believe is on YouTube. It very much has the vibes of Pirates of Silicon valley, which is a brilliant movie about Steve Jobs and Bill Gates - but street art related.
As you can imagine, the spray can is to street art, as silicon is to tech companies. Today a lot of street art and graffiti use all kinds of materials from dynamite to glue, but at the essence of it all is the essential brand or name that is being painted.
So - first you need to pick your name.
The name of your piece is going to be important because you are likely going to be working on this for quite a while. You likely will paint your name over and over again tens of thousands of times, so picking this carefully in the beginning is important.
Important aspects here are around the letters you pick, their combination and the deeper meaning of the word for you (founder-market fit?). The letters you pick are important because you can have uniquely expressive lowercase and uppercase letters. Sometimes the letter combinations are important also, because they will allow your entire word to either take up more space or be easier to read and write. For example, a lowercase g and an uppercase G are totally different shapes, so there's a lot you can do with it. Comparing this to a P/p for example, which doesn’t look that different in both forms. You also need to think about how distinguishable a letter is with various styles. For example, a U and V can look similar, so you need to be conscious how the letters will need to be drawn to make sure it is legible.
Unlike picking a good start up company name, you don't need to worry about it being easy to pronounce or getting a good dot com address. In fact, it’s probably better if it’s harder to pronounce, so the police records on you result in mistaken inputs, and less attention from the wrong people.
It’s worth noting, like many startup names, there is likely someone who already painted your word before you. It’s going to be up to you whether you can out execute and differentiate them when doubling down on yours.
Once you are clear on your name, then you need to understand your tools. Like building your startup, where there are tons of frameworks and languages you can use, you can decide to go commercial or bespoke.
As I mentioned, the tooling here is endless, but the goal is to make a mark that lasts. From the smallest point of impact with the longest lasting mark, many graffiti artists will have some form of a chisel. This lets you carve into plastic, mirrors, windows or metal. An amateur will carry around a key or sharp piece of metal, but the pros will have diamond tipped drill bits. You can get these at your local hardware store, and nothing will be out of your reach. With these drill bits, you will have high expressivity, but carry around a very small object.
Next is your pens. Street artists love drips, so the best pens are the ones that let you control how much ink is released when you draw. These can be literal mops, that let you squeeze out ink on a surface, or they can be paint based with felt tips. Whichever you use, an intentional graffiti artist is going to want to last even if it's painted over. In this case, a good mixture of ink will seep through multiple layers of paint and leave a lasting impression.
The most common tool for a graffiti artist is going to be the spray can. Surprisingly, there are a lot of different kinds of spray paint, and even more so, there are countless types of spray paint tips. From the paint side, you can find a series of commercially available kinds, such as Rustoleum, which is aerosol oil paint, Krylon - which is a common acrylic, or even lighter materials that are meant for the likes of floral coloring. Technically, at some stores, you can also find aerosol food sprays, but that's not going to fit the “permanent” bill.
If you go to a true art store, you get an entire different category of spray paints which are going to specialize in details that matter for an on the run artist. For one, you can get a much wider array of colors, which aren’t going to be available on the mass market. Everything from avocado green to skylark blue. These wider colors come in a variety of materials , such as oil and acrylic also, but most importantly is that they can dry quickly due to a higher pressure, which gives you the ability to cover more surface quickly. Another key important detail is to decide on oil or acrylic, but not to mix them. Oil can paint on anything, but will break up an acrylic spray if painted over while wet.
Next are the spray caps. This is the heart and soul of a graffiti artists mode of expression. There are two main categories of a spray cap - female and male tips. Most consumer spray paint today uses a female tip insert, as the most common street artists tips are male based. As a result, the markets have adapted and started creating female tip adapters, but they often leak paint.
The spray caps will vary in a few important ways. First, the nozzle of a spray cap will control the release of paint from the spray can. What this means is that the surface of the spray can be controlled based on the size of the nozzle hole and the surface of a spray cap exit. A larger surface on a spray cap will let you have a larger cone of paint, which can distribute more paint quickly. Also this will allow you to have highly controlled effects when moving the spray can quickly closer and farther away from the wall. I’ll go into this shortly, but a talented artist will master their “can control”. A negative on the larger nozzles is that it will cause the paint to drip when not used carefully. You don’t want to be the artist with tons of drips, since it looks tacky and can take time to fix up. To compliment large nozzle spray caps are smaller nozzle caps. These are important for details, when you are trying to make fine lines. Also there are caps that control the speed of the spray, so you can create intentional airy looks, such as for certain visual effects. Finally, there are certain caps that will spray their nozzle cone unevenly, such that the edge of the cone nozzle will collect paint faster than the center - which allows you to create flares.
An important point to consider is that you need to take good care of your tips once you use them. Since the spray paint will dry quickly, it's good to give you caps a “cleaning” spray by turning your caps upside down and spraying out air, to make sure the nozzles don't clog and paint doesn't dry by affecting the cone output. For this reason, it's good to have backup nozzles.
Personally, my favorite tip is the NY Fat. This is a long time favorite and was originally inspired by the spray nozzles found on cleaning materials, such as spray-on bleach. As you can imagine, the original spray paint cans used spray tips from other household aerosol products, and did not have the wide range of selection. Another trick that used to be used for getting interesting color effects was to intentionally clog your tips with one color, and then use that tip on a new color can to get the after spray of the first color. This kind of mixing and technique is advanced.
Next you need to pick your style.
Next are throw ups. This is the meat and potatoes of the graffiti world. It's often a two color letter form that has a few core elements: a fill, and an outline. Creative artists will play tricks with letters and letter combinations here. The tip of an I for example can be much more than just a dot. You can make it into a crown, a face, or as a startup in growth mode - a dollar sign. Certain letter combinations are also fun to play with - and oppositely others can be harder to read.
The key motion for a throw up is that it should be possible to put up with two cans of paint in a few minutes. You first take your fill color and spray out your outline. Then in reverse order from the direction you painted your outline, you start filling the entire outline. Then you take your second color and go through one time to make a clean outline. One common effect when doing the outline is to add more weight on one side of your outline to create a shadow effect, which gives a popping out look to your letters. Depending on the surface you are painting on and the color contrast, it's good practice to then do one more final outline around the entire piece to create some intentional color contrast against the background. It's not uncommon to add final accents, like bubbles, stars or a common “big” Chinese character.
When it comes to picking the two colors, you want to maximize the contrast between your pieces. Good default colors are blue and white, silver and black, or something with similar contrast. If you get too creative with a red and orange, you risk the chance that the outline and fill aren’t distinct enough to read, and just waste paint.
Notably, when doing a throw up, it's either common to see a quick style that is done alone, or two different people throw up next to each other. As you can imagine, depending on the location you are painting, either you want to have a look out and a switch off between the person painting and person watching - or you want to paint with someone else to simply keep company. If you want to extrapolate to starting a startup, you could say that this person is your cofounder, and while you talk to customers (aka watch for police), your cofounder builds - or vice versa.
This throw up style can also be done at scale, with groups of people. In this case, if you wanted to cover an entire train car in three minutes, you would need 8-10 people who simultaneously know which letters or parts they are covering, and during the fill motion, use one can per hand to do the fill quickly. After the fill in is done, again you coordinate to choose who covers which letters, and then quickly if needed a final clean up can be done.
After throw ups, the more common style is a mural also known as a wild style. This is the most common quality graffiti you will see and varies significantly in quality. Unlike the throw up, these will involve countless colors, attention to detail and many times characters to compliment the letter style. Also when it comes to larger murals, it's more common to see groups of artists paint together. These groups are often not individuals in isolation coming together, but generally are part of a crew. Again, extrapolating a bit, this could be like your startup. This means they are artists who identify with each other and either paint one another’s names on their own pieces for recognition, or have an abbreviated tag that everyone in their crew will paint. The abbreviation is normally a three letter combination, such as MSK or SLC, which may have an original meeting, but they will also use the abbreviations in other sentences that use the same starting letters.
Beyond the traditional tag, throw up and mural, today you have many artists who define themselves either with other materials or characters. Some of the interesting ones being stencils, like the well known Banksy, but others being explosives like Portuguese artist Vhils. Beyond that, bucket paint is also used for very large pieces, which are done with paint rollers and are known as roll outs.
A note about the legibility of the three core types of pieces. When you paint your name in any style, you want to make sure it is easy to read, at least by other graffiti artists. To do this, you will need to make sure the letters you paint have strong power lines. This means the E looks like an E and not an F. The core parts of the letter should be distinct, and to do that you make the core shape of the letter clear or use good colors to contrast the visuals.
One note here on the product - you are going to try and innovate on your letter form, but there is a limited number of letters and ways to draw them legibly, so feel free to take inspiration and copy others. Like a startup pricing model, you don’t need to reinvent the wheel. Find some letters you like and just copy them for your own word. That being said, you should be distinct enough that people don't look at your letters and immediately think that you copied them from a more well known artist. This can happen when another artist has defined a certain style, such as 3d letters or a certain type of block letter form.
Okay - that was a lot on the product. Next I’m going to talk about SALES - or as a graffiti artist would say, “getting up”. Getting up is everything, so you can also think of it as capturing market share. In any city, there is a limited number of spots that you can safely paint at that are available at any time. Being able to differentiate on when you get up will define how you are recognized.
Of course, when you pick locations there are the basic places like bridges and tunnels, or abandoned buildings which are going to lend for longer painting times. Often these places will also have your pieces last longer, but if a city has a limited number of painting spots, you can also expect your pieces to be painted over by another artist at some point. These can be found in any city and the right eye will know where to look.
Next you are going to have higher profile places. These are going to be higher risk, but with the reward of lasting longer. Higher profile here will mean that more eyeballs will see what you paint. This can mean painting near a high traffic area, like a freeway, or getting up on a roof that has large visibility across a larger area.
When it comes to painting in high profile areas that aren’t hard to reach, you can also expect your piece to be painted over quickly by the “buff”-ers (not to be mistaken with bandwidth), so you’ll want to make sure to get a picture in case it's painted over even by the morning time. Most cities will have a hotline that citizens can call, and a budget to pay for painting over graffiti. Based on this budget, a number of contract based graffiti removing services will be rewarded for the pieces they paint over. This is actually a larger business than most people realize and if I wasn’t such pro-graffiti, would likely be something I’d build a better version on.
Finally in regards to location, you want to also consider opportunities to get moving landmarks. The most notable type is a train car. You can imagine getting a full train with your tag moving around the city, but in reality, the moment a train car is painted, they are taken out of service and cleaned. In 1980s New York, the subway culture surrounding trains was one where people painted the trains in the train yards before they would go out, then watch them in circulation.
Another great moving landmark are box trucks. These are large white trucks with clean surfaces
Today the best kinds of trains to paint are freight trains. Freight trains are going to travel around the country and will often not get painted over if you follow one keynote: don't paint over the serial number. Freight cars each have key identification blocks which contain the train information and car. As you paint freight trains, either in their train yards or even while they are moving slowly, you want to avoid painting over the ID information, so the train cars have no reason to be serviced.
One last point when it comes to locations - there are rules around places that you definitely don't want to paint. The key places are government buildings, places of worship, and peoples houses. For obvious reasons in each, you just don't do that.
Going back to marketshare, since there are a limited number of good spots in any city, you need to watch out for competition. In graffiti, every time someone is painted over, it's loaded with meaning. It's almost always intentional. I like to think of this as the equivalent of buying ads against the search terms of your competitors. The main difference though is that with a startup, it can feel like getting punched in the face, but with graffiti, your competition will actually punch you in the face.
If you paint a piece and then someone else paints over it, it's a message saying “I can do it too” or “I’m better than you”. This is important because if someone paints over you, you have to make it your life's mission to paint over anything you see of theirs. Also in regards to crews, if a member of your crew gets painted over, that means your whole crew will be unleashed on that person, if not their entire crew.
Unsurprisingly this can get very aggressive very quickly, and with the internet, it can get amplified when there is any kind of artist beef.
When you paint for visibility, one goal is to be photographed and even get press. Some pieces will be very instagram-able, and others will be in locations that naturally get photographed - and therefore shared. In regards to the press, there are countless graffiti blogs for cities specifically and also the world. It's always a goal to get featured in one of the larger graffiti magazines that are printed. This Techcrunch for the graffiti world.
Also like any sales process, you don't want to be limited to a small region. If you are serious, you should look for international presence. This can mean you travel solely for graffiti related trips. It can be in tandem with an art show or large art festival,
Once you have your PRODUCT and you have a clear idea of your SALES plan, then you want to think about a mature MARKETING strategy.
Graffiti “marketing” is very simple but important. In an instagram world, you can often get more views on a piece that is posted and well tagged, than you will for in person views.
Back to the location point, your location is everything when it comes to getting strangers to photograph and post your work. If you are in an art district, you will likely get the visiting street art photographers to post your pieces, but you want to go beyond that and get bystanders who just like your visual aesthetic.
In the rare but ideal cases, it's wonderful to get your art pieces in iconic places that can also be eternalized. Specifically, getting your pieces in places where they end up being in the background of a movie or major photograph is a huge win. This can be strategic, in that you scout upcoming movie sets and paint at night, or keep a steady presence in places that you know to be common photogenic locations for ads.
This is a lot, so I’m going to quickly go through the final two parts: Hiring and Selling.
As I mentioned earlier, a good artist is going to be part of a crew. And a good crew is going to get much more market share than an individual artist. (Indie founder vs great founding team?) To get good at hiring, you are going to need to find undervalued talent and be an active member of your community. While most crews will be a group of close friends, there are also numerous international crews with large scale presence in multiple cities. When prominent artists join prominent crews, it's very widely recognized in the graffiti world.
I won’t go into too much detail here, but key ways to find great talent are looking in under valued places. For one, countries that you wouldn’t normally check for street art or in cities that you might figure have good street art presence.
One major find for the art world was from Australia. For reasons, I’m not too sure about, Australia has an incredible graffiti culture and some of the best “unknown” artists emerged from there over the past twenty years. Unlike places with a rich hip hop history like New York, the unknown artists in graffiti hot spots or emerging art countries are a great add to your graffiti crew.
To conclude, many graffiti artists are going to paint for the love of painting, but another ulterior motive is the eventual existence. An exit for a graffiti artist can look like one of a few options: either a large brand deal, a lifestyle business, or major gallery offerings. Some major brand deals are the likes of Sheppard Faire, who got wide acclaim around his work on the Obama campaign posters. There are countless life style graffiti artists who sell clothes, toys or prints on the side.
And finally, all that work for publicity can pump the major artists gallery offering. One of the more publicly prominent ones are the likes of Banksy, who uses his publicity and stunts to pull in tens of millions of dollars for his works.
To conclude, with all the points shared, the obvious outcome for most graffiti artists is getting arrested, so buyer beware. And maybe it’s not so far off from starting a startup, knowing that the default case is your company dying. But we do it anyway. If you are generally just curious about painting and want to avoid all the drama, there is some great VR content that lets you experience the experience of spray painting with surprising accuracy. If you want the experience of starting a start up though, I guess you are all in the right place.