When Dida Clifton launched a small bookkeeping business to keep busy while her husband flew fighter jets, she never imagined it would evolve into a full-blown mission. Today, she’s the CEO and Founder of TheOfficeSquad, a back-office support company that’s helping small business owners across the country run faster, smarter, and with more clarity than ever before.
What began as a side gig has turned into a nationwide vision—one that blends Dida’s military background with her relentless drive to fix broken systems and support entrepreneurs in real, sustainable ways.
Accidental Entrepreneur. Intentional Impact.
Dida’s career didn’t start with a business plan—it started with service. As an Air Force veteran and technician in fighter operations, she saw the parallels between fighter pilots and small business owners: high-stakes decisions, intense focus, and egos built for survival.
She also saw a broken industry full of unqualified bookkeepers causing chaos for the very people trying to grow. “I wanted to fix it,” she said. “To provide real support—with accountable, professional bookkeeping. And… here we are.”
Growing a Business, One Hard Lesson at a Time
Building a company from scratch wasn’t easy. “The hardest part was figuring out how to grow when you know nothing at the start,” she admits. Entrepreneurs often feel they need to have all the answers—but Dida knows the truth: growth comes from learning, adjusting, and doing it anyway.
The most rewarding part? Watching her clients finally get it—seeing the moment they realize trustworthy, affordable help does exist. “When they begin to trust the process and see their business finally stabilize or grow—that’s amazing.”
Breaking Barriers, Building Confidence
Raised without limitations around gender roles, Dida grew up changing oil and fixing tires just like her brother. That upbringing shaped her mindset—one she carried into the military and business world.
So when she sees today’s conversations about women in business still framed in terms of limitations, she pushes back. “It’s almost 2026. Why are we still pointing out the difference? My advice? Pursue whatever you want. Dream big. And don’t believe people who haven’t caught up yet.”
A Brand That Took Flight (Once She Let It)
The turning point in Dida’s entrepreneurial journey came in 2017, when she stopped listening to other people’s opinions about her brand. Her use of fighter pilot metaphors, military structure, and a unique, all-inclusive model for back-office support? She leaned into it—finally.
And it worked.
“When I finally said ‘F it’ and did what I wanted from the start, the brand started to grow,” she said. “Imagine where I’d be if I started that in 2001.”
What’s Next: National Expansion
Dida has been chasing the same mission for 15+ years: to create a national brand that empowers small businesses through exceptional bookkeeping and operational support. The path hasn’t been linear—there’ve been pivots, pandemics, and plenty of chaos. But she’s closer than ever.
IAW: A Surprise Support System
When Dida moved to a small town and transitioned her team to remote work, she joined IAW to make new connections. What she found was something even better.
“I didn’t expect the support system IAW provides. It’s been a resource I didn’t know I needed,” she shared. Her advice to new members? “Make the time to attend events. Every time I do, I leave more confident in myself and my goals. It’s always worth it.”
Connect with Dida Clifton
🌐 www.theofficesquad.com
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