Hidden Gems: Meet Rebecca Montgomery of RM Executive Bookkeeping

Today we’d like to introduce you to Rebecca Montgomery.

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
My journey has been anything but linear. I became a single mom at a young age and had to learn how to be both mother and father to my two daughters. There were years when I worked two jobs just to keep things going, and I didn’t have the luxury of waiting for the perfect opportunity — I took what was in front of me and figured it out along the way.

Over the years, I’ve worn a lot of hats — bookstore manager, controller of multi-million-dollar construction companies, notary, serial entrepreneur, and now small business owner. Each chapter taught me something valuable: the discipline of hard work, the importance of continuous learning (even if it meant taking classes on my lunch break), and the resilience that comes from hearing “no” but choosing to move forward anyway.

My story, though, isn’t just about work — it’s about growth, love, and the people who helped me along the way. I’ve been fortunate to have a close, supportive family that showed up when I needed them most. And my daughters — they’ve always been my reason and my inspiration. They reminded me why I was pushing forward and, in many ways, taught me just as much as I taught them.

Today, I run my own bookkeeping firm and have co-founded Strong with Mom, a nonprofit dedicated to empowering single mothers through workshops, career support, and community. That work feels like the natural extension of my journey — turning lived experience into something that helps others build stronger futures for themselves and their families.

I’ve worked hard for what I have, but I also recognize the privilege of having support when I needed it. The combination of both — persistence and grace — shaped who I am today and continues to guide everything I do.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Has it been a smooth road? Not even close. But honestly, whose road ever is? There were seasons when I worked two jobs just to keep the lights on and food on the table while raising my daughters on my own. As a single mom, I had to be everything — provider, comforter, disciplinarian, chauffeur — and some days the weight of it all felt like too much.

Professionally, it wasn’t any easier. When I left my family’s construction company, I thought my experience would open doors. Instead, I couldn’t even get hired for entry-level jobs I was overqualified for. I remember applying to be a cashier and not even getting a call back. It was humbling — and, if I’m being honest, really discouraging.

But those hard seasons shaped me. Working for my dad’s company taught me finance, contracts, and leadership from the ground up. Getting turned down by employers pushed me to build something of my own. And raising two girls on my own taught me a kind of resilience I didn’t know existed. I was also lucky to have a close family who truly lived out “it takes a village.” Even when things were hard, I never felt completely alone — there was always someone reminding me that we’d figure it out together.

So no, the road hasn’t been smooth — but every bump built the foundation for the life I have now. What started as survival has become strength, and that strength is what I now get to pour into others.

Thanks – so what else should our readers know about RM Executive Bookkeeping?
My company, RM Executive Bookkeeping, provides concierge-style accounting and consulting services for small businesses. I specialize in going beyond “data entry bookkeeping” to deliver financial clarity and strategy. That means everything from cleanups and QuickBooks system reviews to high-level services like job costing, cash flow planning, forecasting, and reporting that actually helps owners make decisions.

What sets me apart is that I don’t just provide numbers—I help business owners see their books as a tool for growth. I’m known for creating order where there’s chaos, streamlining systems, and giving entrepreneurs back their time so they can focus on their craft. I’m most proud of building a brand that feels approachable and professional at the same time. Whether a client is a contractor, a salon owner, or a growing service-based business, I meet them where they are and help them build a financial foundation for the next chapter.

Are there any apps, books, podcasts, blogs or other resources you think our readers should check out?
I’m a lifelong learner, so I pull inspiration from a lot of places — books, podcasts, people, and everyday experiences. For business and mindset, I’ve leaned into books like Buy Back Your Time by Dan Martell and Start With Why by Simon Sinek. I love podcasts that mix inspiration with real talk, like Women & Money with Suze Orman and Unlocking Us with Brené Brown.

But the resource that really keeps me centered is my community. My BNI group — especially the incredible women you see in the photo — has been a huge part of my personal and professional growth. We push each other, we laugh a lot, and sometimes we literally jump for joy at the beach. There’s something powerful about surrounding yourself with people who are also building, learning, and showing up every day.

And of course, my daughters are my greatest inspiration. They remind me why I do this work — both through my business and through our foundation. Working alongside them as my co-founders makes everything I do feel that much more meaningful.

Contact Info:

• Website: https://www.rmexecutivebookkeeping.com
• Facebook: https://www.facebook.com/profile.php?id=61550975559187&mibextid=wwXIfr&mibextid=wwXIfr
• LinkedIn: https://www.linkedin.com/in/montgomery-rebecca/