Stephanie Cummings: Helping You Manage Household Upkeep

Need an assistant to handle some tasks around your home? There’s an app for that

When Stephanie Cummings started doing odd tasks around people’s houses four years ago to make some extra money on the side, she had no idea that concept would be the heart of the tech company she runs today.

headshot of Stephanie Cummings, CEO of Please Assist Me
Jenny Wang

Cummings founded Please Assist Me in 2018 alongside her husband, Rashad Cummings, after feeling like there wasn’t a solution to manage upkeep around the house. Please Assist Me is a tech platform that connects people with reliable assistants to help them manage day-to-day chores and tasks. 

"I knew that tech could be a solution to a lot of the problems that people are facing at home," Cummings told Lifewire in a video interview. "That was kind of what prompted me, like wow, a lot of people say there are a lot of players in the home space, but there really [is] no one that’s providing a solution that can help you manage it all in an efficient way."

Trained assistants on Please Assist Me’s platform connect with users to handle tasks such as grocery shopping, cleaning, laundry, or anything they need around the home. Please Assist Me is currently operational in Washington, DC, at select apartment complexes.

Quick Facts

  • Name: Stephanie Cummings 
  • Age: 29
  • From: North Carolina
  • What she does for fun: Reading, coding, being outdoors, and exploring historical areas around DC.
  • Key quote or motto she lives by: "I try to tell myself to get off the roller coaster. In startup life, you can have your biggest high and biggest low on the same day."

How Becoming a Tech Founder Came Naturally

Cummings’ mom was her calculus teacher in high school and she inspired Stephanie's love for STEM. With her father being a software engineer, her mother an industrial engineer and educator, and her cousins coders, Cummings had plenty of mentors to guide her on this journey. She said she was lucky to be surrounded by technologists growing up because it helped her ease into her role today. 

"It’s kind of natural in our family, which I think is very unusual for African American families," she said about her technologically advanced family, which she’s not used to seeing in her community. "I’m very lucky to be born into the family that I was born into."

"The mission is to help people find balance in this crazy thing called life and we’re really trying to solve the work-life balance problem."

All of Please Assist Me’s technology has been built by Cummings, herself. With the company in the midst of raising a venture capital round, she’s now looking to hire some outside help. Cummings said she taught herself and became proficient in some frameworks for building applications like React and React Native, on the front and back end.

Facing Adversity

Cummings said she often is doubted for her technological skills, as if people wouldn’t believe she built the company’s application on her own.  

"So I am a female tech entrepreneur and African American. [You’d] be surprised when I’m having investor conversations and the number one question we get is, 'Well who coded your app?'" Cummings shared.

Woman in a Please Assist Me shirt arranging pillows on a couch
Jocelyn Burks

Cummings said she has countless stories about the blatant racism and sexism she has come across in her line of work. But to avoid being labeled as an "angry Black woman," she often pushes these instances to the side and stays steadfast on what she’s trying to accomplish with Please Assist Me. Despite these incidents, Cummings said moving her business to Washington, DC from its original home in Nashville has been successful, since its a more progressive market.

"There’s been multiple times that we have been at networking events, especially high-end networking events, where people automatically assume that we’re there to collect their glass or give them an hors d'oeuvre," Cummings shared. "It’s something we experience everyday, but it’s kind of water off our backs at this time."

Pushing Forward

Please Assist Me has raised $415,000 in venture capital from a few investors, friends, and family. As of two weeks ago, the company now officially is raising its seed funding round. Cummings said this funding will help advance her company’s mission and allow her to bring on marketing and sales help. 

Even though Cummings and her husband run the business full time, along with a marketing coordinator, one of the unique aspects for Please Assist Me is the fact that all of the assistants using its platform are W-2 part-time employees, which adds an extra layer of job security for them. A majority of the assistants on the platform are minority women, and, with the company currently in a big hiring push, Cummings is looking to bring on more people. 

"I knew that tech could be a solution to a lot of the problems that people are facing at home."

"A lot of people say the home services space is a graveyard because there are companies who try the Uber model and use it for a home," she said. "It doesn’t work that way, you can’t send some random person you haven’t trained, haven’t vetted into someone’s home and expect for it to turn out well."

Taking that extra step to train and invest in employees seems to be paying off. Cummings said 90% of clients continue to use Please Assist Me’s services until they move out of the company’s service areas, which are mainly in Opportunity Zones with affordable housing. 

A pair of black Please Assist Me laundry bags resting on a bed
Jocelyn Burks

Please Assist Me took a big hit when Cummings was forced to pause all in-home services last year in the midst of the pandemic. She took a step back to evaluate the proper path to continue serving clients, like getting personal protective equipment, offering deep cleanings, and only allowing contactless services like grocery drop-offs for some time. Since reopening, Cummings said business has been booming. This year, she’s focused on hiring, expanding her business platform, and trying to reach more markets.

"The mission is to help people find balance in this crazy thing called life, and we’re really trying to solve the work-life balance problem," she shared. "This year is really to grow our base in the DC market and demonstrate how profitable this could be."

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