Think

My favorite stories are all about hustle and Jeremy’s story is precisely that. In the fall of 2014, Jeremy Wolff quit his nine to five day job doing marketing and sales in the pharmaceutical industry. He did this while living in New York City of all places and took a huge leap of faith to pursue his dreams: being an artist.

I spoke with Jeremy to get his story of how he went from a corporate slave to becoming a full time artist, and flipping the term “starving artist” on it’s head by making many, thousands of dollars for his paintings and selling them to artists, celebrities and athletes.

Dan Reich: What was the decision of quitting your job like?

Wolff: Quitting my job was probably the biggest and hardest decision I have ever made. It was not something I just did randomly one day. It was a thoughtful process and a decision I had thought about for years before actually doing so. It is my opinion that hundreds and thousands of people go through life never knowing exactly what they want to do with their career. They end up jumping from job to job, chasing that higher title and salary down a path through standard and monotonous corporate America. I often questioned what it was I wanted to end up doing. I knew I had a diverse and creative skill set, but I never was given an opportunity to show that at any of the jobs that I had during my corporate stint.

It wasn’t until I took a 10-day vacation on a trip to Israel for my birthright where I got to reflect on my career and think deeply about what I wanted my life to be. We were in a very artsy town and I had noticed a lot of street art and vendors selling their artwork for hundreds of dollars and I looked at my friends and said, “I can absolutely do that.” My friends looked at me like I was crazy at first but it was that day that I knew I was eventually going to give it a go.

Reich: What were some of the first steps you took to changing your career and becoming an artist?

Wolff: The first thing I thought about was whether it was realistic or not. I thought about my immediate network of family, friends, and past co-workers. I knew my strongest asset in the beginning would be word of mouth. In fact, I still think that is my strongest asset as I continue to grow and build my network. I have always prided myself as someone who never burns bridges. I have always made an effort to be the best I can at staying in touch with people. I figured if I could get one or two people from that core network to commission me for a painting in the beginning months it would be a great start. After all, I didn’t even have a portfolio of work to show off in order to gain any exposure. I knew I had to work diligently to have something to show in order to gain clients. Sure enough I did get a couple commissions from some friends and family and thus my art career had begun.

Reich: It must have been tough in the beginning not knowing when your next paycheck was going to come in. How did you manage to pay your bills?

Wolff: Tough is an understatement. It was always a grind. 20-hour days. Not all of those hours were spent doing tangible work, but more so brainstorming my next steps and figuring out my path. I knew I needed a way to make some quick cash any time I needed it. Gotta eat right? So, it was the beginning of September, nearing the end of the baseball season and September 25th, 2014 was Derek Jeter’s last home game. I thought this would be a great opportunity by doing a Derek Jeter portrait and having some prints made up to sell in front of the stadium. I painted an oil painting close up of Jeter taking an at bat, had 150 prints made, along with some business cards that featured the painting on it. I packed up the prints in a bag, borrowed my friends Jeter jersey, and stood out side Yankees Stadium selling prints from anywhere between 5 to 20 dollars each. Each time I sold a print I made sure to give the buyer a business card and told them I also work on commission. I ended up selling around 100 or so of those prints during that series and made right around $1200 cash. Not only that, but a dozen of those people that bought a print contacted me and commissioned me to do an original piece for them later on.

So I had figured out a way to make some quick cash while also getting my name out there. I continued with the New York sports theme for a little while and knew that whenever I needed some emergency money, I could go out to Madison Square Garden or Metlife Stadium to sell some Rangers or Giants prints. It was a large portion of my initial income when some would say I was a “starving artist”.

Reich: But you’re not starving anymore. I know social media has played a huge role in your success. Can you elaborate on your use of Instagram and other social media?

Wolff: There is so much to tell about social media so I will do my best to give everyone as much insight as I can. Instagram has changed my life and social media has given the term “over night success story” a new meaning. Instagram alone has over 600 million active monthly users. As a visual artist this was my obvious choice in terms of which outlet I focused most on. I told myself that I am not only an artist, but I must become an expert in social media as well. I consider Instagram half my job. In two years I have gained 16K followers and that number grows each and every day.

Reich: Tell us more about your Instagram activity. What are some tips you can give to other entrepreneurs?

Wolff: One great thing about social media is that everyone of importance is represented on social media and if they aren’t then they are way behind the eight ball. Because of that, it is so important to be as active as possible. The more activity you have the more you will align with the algorithm of Facebook/Instagram.

The first thing I recommend when it comes to Instagram is to have role models. There has got to be one person or business that you look at and say to yourself, “I want to be like that.” For me, there were several artists that I chose to use as role models for my career. I used well known artists like Alec Monopoly, Retna, King Saladeen, BK The Artist, Bradley Theodore, and Mr. Brainwash just to name a few. I made it a purpose of my life to study these individuals. What connections have they made? What people are they talking to? Not only that, but I have taken it further and gone out and met a lot of those artists and have become friends and acquaintances. I think it is fair to say that I have piggy backed off some of those artists success.

Every night before I go to sleep I will go to one of the aforementioned artists page, take their most recent photo and begin following the accounts that have liked the picture. I also unfollow accounts to maintain a comfortable followers ratio. Then I ‘like’ over 1000 random pictures using hashtags that align with what I am working on. I am sure many people are aware that there are plenty of computer robots that can do this automatically for you, and there are. You can pay for this service, but why pay to have something completely automated when you can do it yourself but smarter? I focus in on my target market. I am coming in contact with people who I know are already interested in art because I am finding them through other artist’s accounts. This gives me better odds that I will one day come in contact with one of there collectors who may be spending thousands of dollars and investing in emerging artists like myself.

Reich: Tell me more about the business side of art.

Wolff: I think I am learning it as I go. I think there is a whole side of the art world I haven’t even come close to divulging into yet. The gallery scene is something I have every intention of breaking into one day when the right opportunity comes along. One thing I do know is that it is changing. Artists are beginning to realize they don’t necessarily need the galleries. I like to think about Chance The Rapper and how he became who he was with out a record label. We have the tools to do everything on our own these days.

Reich: What are some of your best experiences so far on this journey?

Wolff: Oh wow, there are some pretty surreal moments, I can’t lie. That’s a tough question. I have met some of my child hood sports hero’s who have personally signed my original pieces. Kim Kardashian posted one of my paintings on her website, that was a wild morning. I got to live body paint a model during this past Art Basel in Miami. I have met some amazing people that inspire me to be great, people you wouldn’t normally get to meet. But, I think the best experiences are when I get to see people admiring my work. Putting smiles on faces from a painting is so powerful. Being able to inspire other people to chase their dream. Being able to spread a message through imagery that I created. It’s just a special feeling and one that is hard to describe.

Reich: What do you have on your horizon?

Wolff: I have some really cool projects coming up. I am currently working on my “Cartoon Money Team” series, which as you know features a Forbes Magazine cover with “Cartoon’s Richest Characters”. I have around 12 ideas in which I am going to include the 5 characters I deemed to be the Money Team. So you can be on the look out for that theme to continue. I also have a few murals planned to happen in 2017 and have already begun working out details on painting my first exotic car during Art Basel week 2017 down in Miami.

Reich: Give one piece of advice to other entrepreneurs and artists.

Wolff: My one piece of advice is the cliché that Rome wasn’t built in one day. While it is possible to get a viral hit in today’s day and age, being an entrepreneur is about gaining a reputation and that seldom happens over night. Just as in the corporate world you need a resume to get a job, it works the same way for yourself. I look at my career as an artist and entrepreneur the same way I looked at it while I had the normal 9 to 5. I told myself I am at the entry level of being an artist and I need to work my way up. For some it happens quicker than others as it does with corporate jobs as well. But, you need to crawl before you walk and walk before you run. Take it step by step. Small goals first and make them bigger and bigger each year.