‘The people’s esquire’ Arleesha Wilson wins $10k prize, will grow her business, bridge justice gap


Arleesa Wilson, known as ‘The People’s Esquire.’

Arleesa Wilson, known as ‘The People’s Esquire.’

Cleveland Attorney Arleesha Wilson, known as ‘The People’s Esquire,’ is the winner of the $10,000 grand prize in JumpStart Inc.’s fall 2020 Core City: Cleveland Impact program. She intends to use the funds to grow her business and continue her mission of providing affordable legal resources for people who need them most.

“My mission is to close the justice gap one client at a time by helping them access legal services they can use,” said the 35-year-old entrepreneur, who has been running The Law Office of Arleesha Wilson at 600 Superior Ave. since 2018. “There’s a group of people who are underserved by the legal market. These are people who can’t afford to pay a typical retainer, which is going to be somewhere between $5,000 and $10,000.”

Wilson added that her law office focuses on real estate and bankruptcy litigation, with most of her clients’ annual incomes falling somewhere between $40,000 and $130,000, so they’re often unable to pay the standard retainer fee. That’s where her firm comes in, offering lower payment options that help people get legal help. Wilson says many people miss out on legal representation because they can’t afford to pay.

“It might be foreclosure and dealing with the bank, and the bank is not necessarily respecting their rights as an owner,” she explained. “It might include eviction, especially given the current economic crisis we have right now, there are a lot of evictions happening, so I represent both tenants and landlords in eviction.”


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Helping Cleveland Businesses Plan Ahead

Core City: Cleveland Impact is a free, 12-week intensive business assistance program. Shanelle Johnson, a senior deal flow associate at JumpStart and the Impact program’s administrator, said Wilson’s pitch was selected out of a group of six others that were part of this fall’s cohort. Participants in the 10th cohort ranged from eye wear producer Ispecz Eyewear to auto repair company Haynes Firestone Tires (see the full list here), but Johnson said it was Wilson’s personality and important community work that won the judges’ vote.

“Over the course of the 12 weeks, the clients meet with us in two to two-and-a-half-hour class sessions, and during that classroom time we will meet and discuss several different topics,” Johnson said. “The Impact program itself is entirely focused on financial projection and capital pitches. So that is our go-to-market strategy, financial projections, KPIs, milestones, as well as your value proposition.”


Shanelle Johnson of Jumpstart Inc.

Shanelle Johnson of Jumpstart Inc.

Working her way through the all-virtual course, Wilson said the most important thing she learned was how to analyze her business from a top-down perspective and how to create a business plan for her firm’s various stages of growth. Law school doesn’t teach students how to start their own practice, she continued, so it’s been up to her to identify resources to help her grow.

Johnson said JumpStart often looks at the Impact program as reverse tuition, since qualified businesses get 12 weeks of free assistance and educational opportunities without having to pay. Businesses must have a revenue threshold of $25,000 or more and demonstrate a significant impact on Cleveland in order to participate in the program, which is funded by Key Bank and the Cleveland Foundation.

Breaking Down the Pitch

In her pitch, Wilson outlined how she would spend the $10,000 grand prize, all with the goal of increasing her business revenue to $1 million by 2023. She said $2,500 will go to computer automation systems to streamline office work, while another $1,900 will be used to create up to five hours of online courses that will teach clients how to handle simple legal issues on their own.

She intends to spend $1,900 of the gift to train to practice fair housing law, which deals with discrimination in home sales and rentals, and an additional $1,600 to develop an app that will allow landlords to communicate more easily with their tenants. These expenditures are focused on making access to her financial litigation services as easy as possible, with the app and online courses especially putting ower into the hands of the people who need it the most.

According to Johnson, JumpStart’s programming is part of the Greater Cleveland Partnership’s Business Growth Collaborative and just one piece of a collaborative business education system that focuses on helping local minority-owned businesses prosper. Additional programs are available at organizations like Cleveland Neighborhood Progress, the Urban League of Greater Cleveland and the Hispanic Business Center.

“Most entrepreneurs, they have been bitten by the entrepreneurship bug and they jump right in,” said Johnson. “So this allows business owners to be able to really stop and look at what’s going on in their business instead of just working in the business.”

Registration to participate in the spring 2021 cohort of the Core City: Cleveland Impact person is currently live through Jan. 25, with the program set to begin on Feb. 26 and the pitch showcase that concludes it scheduled for May 14.

Jumpstart Inc. is an underwriter of The Land, helping to support stories about Cleveland’s entrepreneurial ecosystem.

Collin Cunningham is a freelance journalist who lives in Tremont. When he’s not writing or reporting, Collin likes to read, bike the city and spend time with his two lionhead rabbits, Curtis and Cloud.

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