From Teen Mum to CEO: How Her Executive Assistant Side Hustle Grew Into a 30-Person Team

Renee Hastings did not plan to become a chief executive. In 2014, while holding down a corporate job in Atlanta, she began taking on executive assistant work on the side, a one-woman operation squeezed around the day job once her children had left home. A decade later, that side hustle is Executive Help Now, a virtual assistance agency with a team of around 30. She told the Side Hustle Saturday podcast that others saw the business she was building before she did.

Side hustles have become less common. Just 27% of US adults reported having one in 2025, the lowest share since 2017 and down from 36% a year earlier, according to Bankrate.

The turning point came in 2019. A member of Hastings' online Bible study group put her in touch with an executive who had gone a year without an assistant. 'My boss needs an assistant. He hasn't had one in a year, and you can tell,' the woman said. Once the executive understood how a remote assistant could work, he pushed her to think bigger. 'You need to figure out how to scale this thing. This is genius,' he said. She took the advice and built a team.

How the Executive Assistant Business Took Shape

Executive Help Now runs on a tiered structure, with a business operations manager overseeing success coaches who manage the assistants. Every team member handles administrative work, then specialises in an area such as graphic design, social media, project management or human resources. Beyond assistants, the firm offers business consulting and podcast production support, and matches new clients to a profile based on where their time leaks.

The firm's client base now includes small business owners and content creators, as well as venture capital firms, private equity and real estate investors, and family offices, according to Executive Help Now. Hastings has said demand for virtual assistance doubled during the pandemic. Globally, the market for virtual assistant services was worth about $19.5B (£14.6B) in 2025.

The service draws on the skills Hastings spent decades building in other people's offices. Her first taste of the work came through a summer youth employment programme in Madison, Wisconsin, organising a library for the local Urban League and helping at a temporary staffing agency.

She left school at 16 with a one-month-old son, which put university on hold and moved her straight into clerical work. From there, she rose through administrative posts to executive assistant roles supporting a director, a company president, and eventually chief executives at Fortune 100 and Fortune 500 firms.

The standard she holds staff to reaches back further still. The granddaughter of a sharecropper who moved the family from the American South to an Amish community in Wisconsin, Hastings grew up as the only Black family in the area and was raised to represent it well. 'Everything we do is a representation of this family,' she recalled her grandfather saying. Inside her company, she tells staff that even internal messages should go out without typos.

Scaling Executive Help Now Toward Its Next Chapter

Scaling the business meant learning to let go. 'I never realized how hard it was for my clients to delegate until it came time for me to delegate,' Hastings said, describing the nerves of handing work to her first hire. It also took prompting from friends before she accepted the title that came with it. 'You are the CEO of a whole business,' they told her.

The company has since branched out. After learning podcast production from a retired Sony Music executive of 25 years, Hastings' team built a done-for-you service that was spun into a separate company, Live Stream Editors, which now also produces her own show.

Artificial intelligence handles much of the research, she said, and she named Claude as her preferred tool over ChatGPT, though she is firm that 'AI cannot replace a human.'

Now rebranding and turning down offers to buy the business, Hastings said she still feels she is living out her purpose. Her main lesson for anyone scaling a venture is blunt: 'Put everything in writing.'