The paradox of being a homeless entrepreneur

Bad selfie, while sitting outside the downtown library in Richmond, Virginia, where I was living homeless, earlier this year.  I had just walked a long ways, carrying all my stuff, on a hot humid day, and I found this little ledge to sit down on and take a break.  I turned around, and saw this sign.  This photo just seems to sum up being homeless, anywhere you go, you're not wanted, it doesn't matter where it is.

For the last 20 years, since I left my good paying job as a "Hollywood" lighting technician, because of an injury, my life has been this crazy struggle, skipping along the bottom of society, struggling in and out of homelessness.  When I mention that, or people see me and realize I'm homeless, they jump to all sorts of conclusions, nearly all of which aren't true.

I've now spent about 10 years in some form of homelessness.  About 7 1/2 of those years, I was working full time, way beyond full time (70-100 hours a week as a taxi driver), or near full time.  Here's the kicker, I don't do drugs, legal or illegal.  I don't drink at all anymore.  I'm not an alcoholic who went through a program to quit, I pretty much stopped drinking (which I didn't do much, anyhow) while working as a taxi driver. After driving drunks home every night in my cab, I just stopped drinking, I just got sick of the world attached to beer and booze.

I did struggle with depression, in a serious way, after my dad's death in 2012.  That got serious, but I went through group therapy, took meds, worked through all that. I weaned myself off the depression meds a couple years ago, while a friend from group kept an eye on me in case I got sketchy. 

My main issue, the thing I've struggled with most, was simply not being able to find a good paying job after taxi driving went down the tubes in about 2003.  I struggled in the taxi until 2007, then had to quit for both health and business reasons.  Like millions of other people in other industries, the taxi industry got disrupted by new technology.  First computer dispatching replaced the old CB radios in the cabs, which changed the game, and then Uber and Lyft popped up.  Boom!  Business over.  Like millions of people who lost factory jobs in the 1970's, 1980's, and 1990's, I had to find a new way to make a living.  And I have struggled with that.

During that same time period, there has been a ridiculous amount of outside pressure and influence on my life, from a variety of sources.  I can't really tell the story of this, though it's been the dominant theme of my life for 17-18 years now, because it's so ridiculous.  Finally part of the story came out, and all this weird stuff happened, supposedly, because I scored absurdly high on an I.Q. test 34 years ago.  Someone, somewhere, decided they needed to control my life because of that.  Supposedly.  So I've struggled through nearly two decades of crazy adventures, busting my ass to simply survive, and I can't explain this whole mess to anyone.  The story is just too fucking crazy.  It would be more believable to more people if I said I got abducted by aliens in 2001, brought back ten years later, then dropped in the woods of Oregon where I lived with a Sasquatch family for a few years... and now I have to start over.  That kind of crazy tale is actually more believable than what's actually happened in my life.

So I have 20 years of craziness I can't really talk about.  Now I'm 53, homeless, living in the Hollywood area, with a mouthful of broken teeth (20 years of no dental insurance after a life of too much sugar), and working to rebuild my life and start a viable business around my Sharpie art and my writing. 

What I do have in common with many of you reading this (hopefully), is that I'm working to build a creative/artistic based business, and make a living from that.  What I don't have in common with most of you is my starting point.  I started actually selling my Sharpie art, 4 years ago, while living with my mom, in a small North Carolina town, literally without a dime to my name.  After applying for about 140 jobs over a year or so, and not getting called back, it became obvious a traditional job wasn't going to happen.  So I decided to focus on my Sharpie art, which made me a few buck now and then. 

I've sold over 80 major pieces of art in four years, nearly of all which took 35 to 45 hours to draw.  So while most people look at me and see only a complete failure, I've actually sold more pieces of art than most of the best known masters of painting in their lifetimes.  My drawings may suck, in your opinion, compared to the great artists, but 80+ people thought they were worth paying for.  That's something.  No I'm not making a "good living," at this, even after four years, but I have survived through some tough times, by selling artwork.  However lame my life may seem, there are thousands of people out there who wish they had sold 80 pieces of original art.  That's something.  Yes, I have a long way to go, but I have made quite a bit of progress in some areas.

So now I'm dealing with a weird paradox, as I work to build my art/writing business in a new area, in the cliche' of all cliche's, Hollywood, California.  On one hand, as a homeless man, struggling for food money, bus fare, and basic need money, day to day, my main focus is simply keeping my spirits up, and not getting deeply depressed.  The struggle of homelessness is a struggle not to succumb to depression and give up.  The hardcore street people you see in large cities have mostly given up.  I've found the way to keep my spirits up while homeless is to give myself little "gifts."  In my case, it's mostly food, I'll spend a little money on a caramel sundae at McDonald's, or buy a $6 pepperoni pizza at Little Caesar's.  Little gifts to myself help me keep feeling like an actual human being, a person who will do cool stuff again, some day, not the "homeless person," most people see me as.

But as an entrepreneur, trying to start a small business, I need to spend as little money as possible, to put every dime I can into my little business, buy more art supplies, or copies of drawings to sell, or money to promote somehow.  So my biggest struggle right now, is making small amounts of cash day to day, and to try not to eat too much, but to eat enough to keep my attitude positive, because I get really grumpy when I don't eat much. 

We all have our struggles, the things we battling and struggling with right now.  That's mine.  What's yours?  What's keeping you from the small business, or small creative business, you really want to have?

How I sold 80 major pieces of art, starting without a dime, while homeless

It's a really long and crazy story.  At age 49, I wound up living with my mom in a small North Carolina town, and could not get hired for any job whatsoever.  I sold a drawing in my weird Sharpie "scribble style," now and then.  I decided to focus on making money with my art.  That was in November of 2015.  I literally didn't have a dime to my name.  I had my art supplies, a room in a small apartment, and a refurbished HP laptop still running Windows XP.

I still don't make an actual decent living from my artwork.  But in the last 3 1/2 years, I've sold over 80 of my drawings, most of them for $120 to $160 each, a few sold through a gallery for $250 each.  These drawings, 18" X 24," take me 35 to 45 hours each to draw, on average.  That's not much money per hour of drawing, mostly because I was homeless most of the time I've been drawing and selling these drawings, and have been selling them to pay basic living expenses.  Obviously, if you start in a better position than I did, and you art is of a good quality, much more is possible.

Here's how I sold those 80 drawings:

1.  I committed to doing what it took to actually sell my work.  I decided I was actually going to do the day to day work needed to make and sell my Sharpie drawings.

2.  I sat down at the computer one night, looked through all kinds of art online for about three hours, and asked myself, "What would I actually want to put on my wall?"  I simple stencil of my first childhood hero, Bruce Lee, was the answer to that question.  So I printed out the photo, and drew it in my style.  I knew then that I needed to focus on drawing picture of inspiring people.  That was the subject matter that worked best for my style at that time.

3.  I tapped into the online following I already had from my BMX freestyle blog.  I primarily used Facebook, my main social media platform at the time, to show people my artwork, and ask if anyone would like me to draw them something.  My first orders came within a week or two of doing that.

4.  I sold my art cheap to start with, and offered to re-draw any drawing people didn't like.  A lot of people will tell you, "Don't lower your price, your art is worth much more than that."  Those people don't actually sell art.  They may make a lot of it, and show it off on Instagram and Facebook, but they don't sell much.  Let people get a cool piece of your work for a reasonable price, and make sure they're happy with it.  My first few drawings I sold were 12" X 18," they took me 8 to 12 hours to draw, and I sold them for $20-$25.  The key word there is, I SOLD them.

Then I sold a bunch of 18" X 24" drawings, that took me 18 to 22 hours to draw, for $40 to $50 each.  Again, I SOLD them.  I got better at my craft, my drawings improved, and I raised my prices to $75 each, then to $100 each, then to the $120-$160 range.  I always offered to re-do the drawings if people weren't satisfied.  I never really want to re-draw anything, but I do want people to be happy with my work.  These days, after thousands of hours of drawing, that's not really an issue.  Guess what, not one person who bought a $50 drawing is bummed that my drawings later sold for $150.  I'm now at the point where I'm raising the prices to $350.  I'd rather not sell the original and sell prints at this point, anyhow.

5.  I started a Go Fund Me campaign early on, the idea was to earn raise $1,000 quickly so I would have money to make prints to sell.  I didn't just ask for donations, I did drawings for everyone who pledged money.  In reality, I did raise the $1,000, but I did it drawing by drawing over four months time.  The Go Fund Me campaign just became an easy way to order and pay for my drawings online.  The $1,000 goal encouraged people to help me out and order a drawing.  It also allowed me to draw every single day for four months straight, and get into the rhythm of being an actual working artist.  By the time I reached my goal, I got set up on Paypal, and just kept taking orders online.

6.  Moved to a city that had a decent art scene in North Carolina, though I couldn't afford any place to live.  I wound up living in a tent in the woods, which I definitely DON'T recommend, and scraped by.  Some guys who saw me drawing one day suggested I show my work to a local record shop, which I did.  They liked it, and I wound up doing a small art show there.  That shop, a really cool one, was Earshot Music, and Phred, the owner used my Kurt Cobain drawing for the online flyer (above).  Only a handful of people came to the show, but one was an artist and collector from the 1980's New York City art scene.  He bought the Cobain drawing the day before the show, and wound up buying three more drawings form me.  I also sold about 10 more drawings through the record shop, most to one couple.  That just shows the power of getting artwork out where people can see it. 

I also found one studio/gallery owner who really liked my work in the downtown art scene there, and she sold a few more.  I wound up having trouble getting paid for some of my work there, so that relationship wound up bittersweet.  She promoted my work a lot, but also had trouble paying me sometimes because her cash flow issues.  That's another risk of this that you just have to deal with as things happen. 

7.  When I moved into the tent in the woods, I had several blogs going.  I brought them all into one single personal blog, Steve Emig: The White Bear.  Though three of my blogs drew good sized followings over the seven years before that, I wasn't sure anyone would read a blog about old school BMX freestyle stories, Sharpie artwork, and my thoughts on the future and the economy.  But that blog just had its two year anniversary, and has 76,000 page views in two years.  My blog readers are where most of the early buyers of my artwork came from, and where I still keep getting some art sales from.  I highly recommend a blog, or for most people these days, a Vlog, to promote your artwork, in addition to Instagram, Facebook, and whatever other social media you're using. 

8.  I used Pinterest to help build my web presence for my artwork, and I found one good hashtag to use all the time, #sharpiescribblestyle.  I use other hashtags, particularly on Instagram, which I'm not very psyched on, to be honest.  But Instagran has a huge reach, and can definitely get you followers, and maybe sales.  Use the social media platforms most that you actually like most.  Nearly all my online sales I've done have been handled on Facebook from people who read my blog.  But I took the time to make sure that is you look up #sharpiescribblestyle on Instagram, Twitter, Facebook, Pinterest, or Google images, you'll see A LOT of my drawings.  That just took work, day after day, of actually taking the time to put stuff on each platform, with tags and hashtags, day after day. 

Like I said, I did this while living much lower, and with less resources, than most all of you reading this will ever have to deal with.  I'll go into more depth on these ideas in this blog as time goes by.  But these 8 ideas above are the basics of how I sold over 80 major pieces of art, while homeless most of the time, in the last 3 1/2 years.  Hopefully soon I'll be able to finally get to a place where I can turn this writing and art into an actual, stable living.  I've had a lot of headwinds holding me back at times, but I've had a lot of people help me out, as well, at key moments. 

My battery's going dead, no place to charge at the moment, so I'm going to post this and proffread it when I can.  Sorry for any typos at the moment...