How I Continued Investing Into My Business Despite Some Financial Losses

Published: July 19th, 2020
Ursula Barton
from Portland, Oregon, USA
started February 2012
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Hello again! Remind us who you are and what business you started.

I am a Portland-based artist, and I first started my own brand back in February 2012, featuring my cityscape and bridge ink drawings. Once my own brand became sustainable after three years of non-stop hustle, I started a female artist collective, gallery, and art studio space called Jailhouse Studios in 2016. This then grew into a larger movement once I teamed up with Bethany Von Steuben to expand into retail to amplify the voices that have historically been ignored by the Art wold: BIPOC, Queer, and Female Identifying artists. We remodeled the space in the Buckman neighborhood of Portland that was originally built as the first southeast police department complete with a holding cell, in 1902. We named this new expansion of the gallery and art space Jailbreak Studios and celebrated our Grand Opening on October 4th, 2019.

My main role at Jailbreak Studios is to curate and offer mentorship to Portland-based emerging artists from underrepresented communities. By 2015 I had created a successful mural business for my own work and was looking for a way to reinvest my growing budgets from my commercial art back into my community and help create a more inclusive art scene. One I could be proud to be a part of. I have experienced a considerable amount of sexism in the Art world, from clients and colleagues alike. The mural scene especially has a long way to go with creating environments that embrace and value the female perspective, and not just tokenize it.

I started working with an intersectional feminist activism group called NXT LVL in 2016, it was clear that my experiences in Portland as a white woman in a man’s industry was just a fraction of the inequities being exorcised in our community across all industries. I wanted to do something about it, and thanks to a few large commercial mural projects from 2017-2019, I had some capital to invest in my mission. Curating the Gallery with fine art from many different voices, and finding small-batch, hand-made goods from skilled artists and artisans became my new favorite job. The amount of talent in my community is stunning. From books of poetry to ceramic mugs with a realistic eye sculpted on them, to cheeky collages, and handmade candles I get to smell anytime the stress of owning a small business becomes overwhelming, Jailbreak became an expression of the wide range of high-quality artwork and products that have been copied and undervalued by the Art world I grew up with, and never felt comfortable in.


Tell us about what you’ve been up to! Has the business been growing?

I am lucky that my personal brand has continued to grow more each year, and I am honored to be the first commissioned piece of art for most of my clients. This is something I am proud of, and have been working hard to develop within my brand since my last Starter Story. I took a look at my past three years of commissions and the demographic that was responding to, and supporting my work, and quickly noticed that my clients were overwhelmingly Millenials and young Gen X, and working with me had been their first time commissioning a piece of art by a living artist. This really touched me because it meant that my work, and the way I do business, has invited a new generation to invest in living artists (investing in living artists is radical, paying fairly for creativity is activism). This meant that they felt comfortable enough with me, and resonated with my work enough to try something new, and participate in the art world (as opposed to the Art world) on an economic level, this decision strengthens the creativity you can see in the world around you, I know from experience that the first original painting you connect with and decide to buy despite the financial discomfort it evokes is the hardest painting to buy. It is a difficult decision to make for most people, but once you live with the daily joy it brings to you, the value of art creeps in and becomes contagious.

When you support the small businesses in your community don’t be shy to work together, share resources, and promote one another.

Accessibility and inclusivity are what I have been focusing on within my brand. I have worked to create a safe space for my clients to offer their personal taste and creativity through in person, or FaceTime consultations, as well as expanded on the payment plans I offer so that my time and creativity is valued and buying a work of art is achievable for their income. This approach is true to who I am, and how I feel about the elitism of the Art world, and it has paid off. I am now booked with private commissions for the remainder of 2020.

And I am so glad I am, because since the coronavirus hit Jailbreak has had to close its doors since March 11th, and my county has just now opened for Phase 1 but our number of infections continues to go up, and retail continues to struggle. With no help from the federal or local government, because my business is too young to qualify for most grants, I have been funding the creation of Jailbreak’s new online store from my personal work. With the Black Lives Matter movement in tandem with the pandemic, it is increasingly important to me to keep investing in Jailbreak despite the financial losses. I feel I owe it to the artists I work with to give it everything I have and attempt a pivot in order to support a diverse range of voices reacting to, creating artwork about, and speaking up during this time in history.

This is the highest function of art, to express the human experience. This era of unchecked capitalism has been exposed for its corruption and lack of support for small businesses throughout this pandemic, and I hope that with the introduction of our online platform we can survive in order to continue to support and amplify the voices of our artists despite the uphill battle ahead of us. My workdays have doubled in length as I get back to the early days of the 80-hour hustle, my job title morphing minute by minute as I try to think creatively and strategize on how to connect creators with appreciators.

What have been your biggest lessons learned in the last year?

After 9 months of working together, my business partner decided to go off on her own to create something uniquely hers. Receiving this unexpected news during a pandemic in late April challenged every aspect of myself. This amount of change within our economy, society, and my own professional life took me to a place of fear I had not visited since the beginning of building my brand with a few hundred dollars seven years ago. I had to reevaluate EVERYTHING.

Through this experience, I learned the value of taking a moment to pause and think very honestly about what I was willing to invest into my business, what I was capable of achieving alone, what I was not capable of achieving alone, what kind of help I needed, and what was it I was working so hard for?

My immediate reaction was to give up on Jailbreak and focus on my own growing art brand. But the truth is, creating landscape artwork is only part of who I am as a person, and who I am as a businesswoman. Activism is the other part. I understand that I have earned a lot of my success as an artist because my work is not controversial nor political in nature. I have a great love for my process of art-making and the ongoing exploration of my medium, ink. My fascination with urban patterns, color, and textures drives my style and subject matter, and I am fully aware that landscape paintings are rarely divisive. But I want to create social change, local to global. I want there to be more voices heard, and more income generated for the perspectives of BIPOC, Queer, and Womxn artists and creators, we all deserve to tell our stories and showcase our talents.

Funneling the money I receive from landscapes into a platform that puts these values into action is worth fighting for. This realization fuels the long days that fill a workweek that has no days off. I learned that being honest with myself, what I want to invest my time and money into, my strengths, my weaknesses, and who to ask for help was the first step to getting past my paralyzing fear. This step helped me come to terms with scaling back, investing my remaining capital in eCommerce, and promoting the mission of Jailbreak to create a more inclusive art world as clearly as possible, and unapologetically.

What’s in the plans for the upcoming year, and the next 5 years?

How do we plan for the future in 2020? My only plan is to stay informed on what is going on in the world, pay attention to what is happening around me in my community, and try to find as many intersections of how I can use my voice to help create a better future for EVERYONE and generate income to keep our platform alive so that I can continue to fund the artists I believe in.

In the next 5 years, I want to live in a world with thriving small businesses, diverse expressions of creativity, and a more inclusive society. I am in a place where my strategies change day to day because our realities and circumstances are changing daily. My main plan is to stay true to my voice as an artist, as an activist, and a businesswoman, in order to create as much positive change as possible as I react with thoughtful care to what I have no control over.

Have you read any good books in the last year?

One of my favorite reads this year was Side Effects Of Remembering The Little Things by Bella, an incredibly talented young Portland-based poet who has collaborated with Jailbreak since the beginning. Her new book of poetry is an incredibly honest recount of the full experience of surviving an abusive relationship. Even though her story is about a romantic relationship, the honesty of her emotions paired with her self-awareness helped me examine the relationships and patterns in my life that do not serve me but I continue to return to within my business and personal life.

I have to continually work on reminding myself that I can’t go back to old habits and partnerships just because they are familiar. I struggle with mistaking familiar for comfort. 2020 has no place for this self-inflicted abuse. If you are going to succeed, we need to be deliberate in our decision making, open to new ways of doing things, and kind to ourselves.

Advice for other entrepreneurs who might be struggling to grow their business?

The pandemic is not your fault, our government has not prioritized strengthening small businesses, this is also not your fault (but don’t forget to vote). Focus on what your mission is. Why is it your mission? Do you still agree with it? If you still align with that mission try to find like-minded entrepreneurs with skill sets different from yours. This is a time for collaboration and community building.

We cannot compete with the Amazon’s of the world, but we can choose to spend our money in the community where we live, at the businesses owned by people we care about. When you support the small businesses in your community don’t be shy to work together, share resources, and promote one another. I believe this is the only way small businesses have a chance of survival in 2020.

Are you looking to hire for certain positions right now?

Unfortunately, my ability to pay an employee was one of the casualties of the pandemic.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!