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Bootstrapping A Remote Option

By Audrey Elsberry, posted Apr 19, 2024
Michelle Penczak, shown with her husband, Marine Corps officer Sean Penczak, formed a business because of her own experience as a military spouse. (Photo c/o Michelle Penczak)
Remote work seems an ever-present option in today’s post-pandemic, digital-first world. But for Michelle Penczak, a remote job was a necessity as a military spouse who was constantly moving. The year was 2015, before the rise of Zoom and work-from-home. Penczak’s job as an online personal assistant fell through when her employer went bankrupt. She needed to find something more stable – remote work built for her lifestyle. 

Penczak, who lives in Pender County, built her own solution with Squared Away, her company that now employs over 400 virtual assistants, almost all of whom are also military spouses. Squared Away has been boot-strapped since its founding in 2017, Penczak said. The company has scaled exponentially, increasing its revenue by about 140% between 2022 and 2023 to a total of about $13 million in revenue today. 

Her work with Squared Away landed her on Inc. magazine’s 2024 Female Founders list, which included 250 women whom Inc. highlighted as influential, inspiring and impactful female entrepreneurs. 

This year’s list features women-owned businesses such as Los Angeles clothing brand Show Me Your Mumu and Austin-based soda brand Poppi. Squared Away has received additional nods from Forbes, the Wall Street Journal and the New York Times. 

Penczak was one of two women from North Carolina who made this year’s list.

She gained recognition from Inc. once before. Squared Away was included in the Inc. 5000 2023 list of fastest-growing private companies in the U.S., ranking No. 297 based on revenue growth. The list’s website stated Squared Away gained 1,908% revenue growth over a three-year period.

Squared Away’s clients range from Fortune 500 companies to single-person entities. The business model hinges on filling the niche needs of each client, Penczak said. Her personal assistants can fill needs for larger companies or help small business owners who don’t have the budget to hire a full-time employee. 

“I can take a company that has 2,000 employees and say, ‘Here is where you can save money,’” Penczak said. “And then I can look at a small business that has maybe four or five part-time employees and say, ‘Hey, you can go down to three [employees] or you can outsource XYZ to cut your expenses.’” 

About a month before she moved to Pender County, Penczak applied for Inc.’s Female Founders list. She found out she made the cut in the car on the way to the mountains for a Presidents Day weekend family trip. 

“My husband told me told me I almost blew out his eardrums screaming,” she said. “And then after that, I just burst into tears.” 

Her inclusion on the list of female founders signaled that she had reached her biggest goal as an entrepreneur. When she started Squared Away, her first goal was to sign on 30 military spouses, which she achieved a year later. 

“It’s still sinking in,” she said. 

For Squared Away’s team, the job is entirely online with rigorous expectations for problem-solving and administrative skills, Penczak said. To be a team member at Squared Away, you need to be tech-savvy. 

“We were remote before remote was cool,” she said. “When everybody went remote, we’d already been doing it. The pandemic actually helped us as a business. … We helped our clients shift from in-person work and how to work from home with kids and going from more of a strictly professional to a fully holistic approach to our service.” 

Exemplifying the purpose of her remote-first company, Penczak and her family moved to Hampstead in November. She’s moved with her husband, who’s in the Marine Corps, to Hawaii, Texas, California and now North Carolina. 

The Tar Heel state holds a special place in her heart. Penczak was born and raised in Clinton but feels more known nationally than in her home state. She laughed at the juxtaposition of her national recognition with her neighbors’ mundane responses to her career. Now that she’s back in Eastern North Carolina, she is trying to increase her visibility in the area. 

“Now, looking back, I think about all the struggles that I had,” she said. “I just think about all the sleep that was lost and all the challenges that I’ve overcome. It’s amazing to look back and say, ‘You know what, it didn’t break me, and we are for sure badasses now.’”
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