The Stay-At-Home Bookkeeper Academy Podcast

Hosted by Bill & DeAnna Rogers

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Latest episode

Jun 2026

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EN-US

About the show

Welcome to "The Stay At Home Bookkeeper Academy Podcast"! The Bookkeeper Academy Podcast is where real people rewrite their futures — one honest conversation at a time. Whether you’re burned out from your 9–5, craving more flexibility, dreaming of owning your own business, or simply looking for a career path that gives you control of your time and your income… you’re in the right place. Each episode pulls back the curtain on what it actually takes to build a profitable, flexible bookkeeping business from scratch — even with zero experience. You’ll hear from mentors who built six-figure freedom-based businesses, guest experts who’ve helped thousands of bookkeepers succeed, and everyday entrepreneurs who turned “I hope I can” into “I can’t believe I did.” We talk about the things most people avoid: doubt, overwhelm, starting over, imposter syndrome, and what to do when life feels heavy but you know you’re meant for more. And yes — we also dig into the practical stuff: finding clients, shifting your mindset, building confidence, and taking the very first step.

Listen to episodes

44 recent

June 15, 202641 min

From Corporate to World Traveler How Shantha Built Her Dream Business on the Road

Let’s be honest — most of us didn’t imagine our dream life would involve staring at the same four walls every day. If you’re someone craving more freedom, more travel, and more connection with the people and places you love, this episode is for you.This week, we sit down with Shanta Mony, a travel pro who built her business while juggling a corporate job and raising a family. We talk real talk about:✔️ How to start something new while still working your 9–5✔️ Finding the courage to take imperfect action (even when it’s scary)✔️ Setting boundaries, especially when building a business with a partner✔️ Why travel resets your mental health and sparks creativity in your business✔️ Making networking and connections feel doable and fun — not intimidatingIf you’re tired of feeling stuck or you want to design a business that lets you work from anywhere — maybe even a cruise ship with a view — you’re in the right place.🛳️ Interested in booking your cabin on the Bookkeeping Freedom Cruise? Learn more here 👉 https://bookkeepercruise.lovable.app/ Ready to take the next step? Book a free clarity call or join the Stay-at-Home Bookkeeper Academy today. Your freedom starts now.If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

June 8, 202633 min

The ROI of Letting Go: Bookkeeping Success With Virtual Assistants

Let’s be real - building a business from scratch can feel like you’re stuck in a never-ending storm of busywork, overwhelm, and wearing every hat in the closet. If you’re someone who started your bookkeeping business for more freedom but now feel maxed out on time, energy, and sanity, this episode is for you.Today, we’re joined by Beejel Parmar, an expert in helping entrepreneurs escape the grind by embracing smart delegation. He shares how solopreneurs and small firm owners can get out of the weeds, reclaim precious time, and finally focus on what actually grows their business - all without breaking the bank.We’ll talk about:- How to know when YOU have become your business’s biggest bottleneck- The step-by-step system to figure out what you can and should delegate- Why you don’t need a huge budget (or a leap of faith) to get meaningful help- Simple, low-tech ways to communicate with your team (even if you’re not “techy”)- The mindset shift that unlocks real growth and frees you from tasks that drain your energyIf you’re tired of doing it all, craving more freedom, or just need a nudge to start, listen in. And if this episode sparks something for you - book a free clarity call and let’s talk about how you can build the lifestyle (and business) you actually want.If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

June 1, 202629 min

Juggling Family and Entrepreneurship: Real Talk with Jesse Jackson on Building an 8 Figure Empire

Let’s be honest - none of us grew up dreaming about running payroll or juggling receipts. What we did dream about? More freedom, more time with family, and the chance to carve our own path. Today on the Stay-at-Home Bookkeeper Podcast, we sit down with Jesse Jackson—a powerhouse entrepreneur who jumped from environmental engineering to software, and finally into owning eight (!) automotive shops, all while raising seven kids.If you’re someone who wants more flexibility or you’re tired of building someone else’s dream, you’ll want to hear Jesse’s story. She didn’t start off as an expert, but she kept taking the next brave step—even when it felt scary, even when people told her it couldn’t be done. This episode is packed with real talk about imposter syndrome, letting go of perfection, and giving yourself permission to start messy.We’re talking about:- How to grow from “wearing all the hats” to building a team you trust- Making scary leaps—even when you don’t feel ready- Why you don’t need to do business like everyone else (and how your differences can set you apart)- Practical ways to move forward, one courageously imperfect step at a timeSo, if you’re thinking, “Maybe I could do this…” - you’re right where you need to be. Listen in for inspiration and actionable steps, and if you’re ready for your own transformation, book a free call with us or join the Stay-at-Home Bookkeeper Academy!If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

May 25, 202634 min

Building a Solid Foundation: How to Scale a Bookkeeping Business Without Burning Out

Let’s be real...most of us aren’t dreaming about “operations” when we wake up in the morning. But if you’re someone who wants more freedom, more time, and a business that won’t fall apart the second you step away, this episode is for you.Today, Belinda Ginter joins us to talk about how to break your business down to the basics—the studs, as she puts it—and rebuild with systems and delegation so you’re set up for growth and time freedom. As a Certified Scalable Business Advisor and Business Consultant who has helped transform more than 300 seven- and eight-figure businesses, Belinda brings a powerful mix of operational strategy, mindset coaching, and real-world leadership experience to the conversation.If you’ve ever felt like you’re the bottleneck in your business—or like you need everything to be perfect before you can really grow—you’re going to want to hear this.In this episode, you’ll learn:- Why having a “visionary” brain is awesome—but you still need operator support- How to slow down and choose the right systems before scaling- Why you DON’T have to wait for “perfect” to get started (progress beats perfection every time)- How to start delegating—even when it feels hard- The hidden power of pausing and saying “not right now” to the wrong opportunitiesBelinda has spoken internationally on mindset and business strategy, been featured in publications like Business Insider and The Huffington Post, and has spent years helping leaders build businesses that can thrive without constant oversight. She’s passionate about helping entrepreneurs create scalable operations, strong teams, and businesses that actually support the life they want to live.If you’re tired of being stuck in the weeds and want to start building a business that gives you breathing room, you’re in the right place. Book a call to learn how the Stay-at-Home Bookkeeper Academy can help you get there, step by step.If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

May 18, 202635 min

Why Every Business Owner Needs a Plan: Lessons from an Estate Attorney

Today on the Stay at Home Bookkeeper Podcast, Bill and Deanna Rogers sit down with A.J. Yolofsky, a nationally recognized business and estate planning attorney, to break down what it really takes to protect the business you’re working so hard to build. We’re talking about how to set up a rock-solid foundation, avoid the most common mistakes new business owners make, and seriously level up the value you bring to your clients.If you want to know:- How estate planning is really about living better now (not just “pushing daisies”)- Why having the right business structure isn’t just red tape—it’s peace of mind- The top pitfalls you can skip by getting the right team in your corner- How to turn your bookkeeping knowledge into something clients can’t live without…then you’re in the right place.If you’re craving more flexibility, wanting to help your clients in powerful new ways, or simply tired of Googling your way through legal questions—listen in. And if you’re ready to stop playing small and start building your own advisory dream team, book a call with us or join the Stay-at-Home Bookkeeper Academy today!If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

May 11, 202636 min

From Fear to Freedom: Marketing Mindset for New Bookkeepers with Dolores Hirschman

Let’s be honest - starting a business from scratch can feel pretty overwhelming, especially when you’re staring down a mountain of “shoulds” and feeling stuck in fear. If you’ve ever wondered how anyone actually finds joy, confidence, and momentum in those early days, this episode is for you.In this powerful conversation, Deanna Rogers and Emily Kern sit down with brand expert and serial entrepreneur Dolores Hirschman to talk real talk about what it takes to market yourself as a new business owner. You’ll hear about dropping the idea that you need to be “perfect” before you put yourself out there, how to center everything you do around helping others, and why having fun is actually the secret to productive marketing.If you’re tired of feeling stuck or wondering where to begin, you’ll get practical tips, simple mindset shifts, and plenty of hope that starting messy isn’t just normal, it’s exactly how you build your dream life.In this episode, you’ll learn:- How to start marketing your business (even if you’re brand new)- The simplest ways to spark client conversations without feeling awkward- Why consistency and fun beat perfection every time- Practical tips for staying motivated and confidentIf you’re someone who wants more freedom, or if you just need permission to start where you are, you’re in the right place. Ready to take your first step? Book a free clarity call and let’s chat about your next move!Own a business and need bookkeeping help? Reach out at info@stayathomebookkeeper.com and we’ll connect you with a bookkeeper who fits your needs.If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

May 4, 202642 min

Protecting Your Business and Building Trust: Insurance Essentials for New Bookkeepers with Nathan Glass

Let’s face it—insurance isn’t the first thing most new business owners get excited about. But protecting your business matters, and understanding how to do it doesn’t have to be a snooze-fest. In this episode, we sit down with Nathan Glass, who brings a fresh perspective and a whole lot of heart, making insurance less intimidating and a lot more empowering for bookkeepers at every stage.If you’re tired of feeling unsure about what coverage you actually need, or you’re wondering when is the “right” time to set up protection (spoiler: it’s sooner than you think), this episode is for you.Inside, you’ll learn:- The most common insurance mistakes new business owners make, and how to avoid them- What E&O (professional liability) and cyber liability really mean for bookkeepers- How consistent, genuine relationships (not just a once-a-year policy renewal) are the real secret to sustainable business growth- Simple ways to spot red flags for your clients and add surprising value as a bookkeeper- Why investing in the right community and networking rooms can totally change the gameFeeling overwhelmed by all the options or worried you forgot a step? It’s normal to start messy—but you don’t have to figure it out alone.Want to learn more about Nathan's business - click here: https://utopiarisk.com/ If you’re someone who wants more freedom in your life, more peace of mind, and a business that’s set up to last, this is your episode. Listen in and, when you’re ready, book a free clarity call to get personalized guidance on building your flexible bookkeeping business—with the protection you need from the very first client.If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

April 27, 202640 min

From Overlooked to Unstoppable: Bold Ways Bookkeepers Can Stand Out Locally

Let’s be real—when you’re starting a business, “marketing” can sound expensive and overwhelming. But what if the best way to get noticed isn’t about big budgets or fancy funnels? In this episode, Deanna sits down with Rachel Smith and Dalton Joyner, two creative entrepreneurs who are all about thinking outside the box—especially when it comes to getting your name out there.You’ll hear how Rachel Smith and Dalton Joyner use direct mail in a way that’s smart, affordable (sometimes free!), and makes you unforgettable in your community. From sticky postcards that end up on the fridge to tapping into local business networks, they share strategies for marketing without draining your wallet. Plus, they’ll break down how you can leverage community resources—sometimes, it’s as simple as asking the diner owner if you can leave a flyer near the register.👉 Want to check out the tools, templates, and community Rachel and Dalton use? You can explore everything here: https://communitycardplaybook.com/communitycardhome?am_id=deanna865If you’re someone who dreams of more freedom, or you’re tired of feeling invisible in your bookkeeping business, don’t miss this uplifting and practical conversation. You’ll walk away with new ideas, renewed confidence, and the reminder that marketing doesn’t have to be scary—or expensive—to work.Ready to try something new? Book a free clarity call or join the Stay-at-Home Bookkeeper Academy and take your next step toward the business (and life) you actually want.If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

April 20, 202635 min

The Power of Small Steps: Scott Bell’s Guide to Sustainable Business Growth

Let’s be real...sometimes life throws you a curveball, and suddenly the path you pictured for yourself is totally different. In this episode, we sit down with Scott Bell, a business coach who’s lived through dramatic life transitions - from the unexpected loss of a loved one to inheriting multiple businesses overnight, completely restructuring, scaling, and eventually selling them for more freedom.If you’ve ever found yourself stuck, doubting what you’re capable of, or just craving a life that fits you better, you’re not alone. Scott Bell opens up about overcoming imposter syndrome, weathering tough moments, and the little daily habits that can keep you moving toward your goals, even when everything feels overwhelming.We're diving into:✅ How to stay resilient when your whole life shifts unexpectedly✅ Simple mindset shifts to turn self-doubt into action✅ The power of small, daily routines (including Scott Bell’s “Awesomeness Swipe File” you’ll want to steal)✅ How taking imperfect action is the real secret to building freedomIf you’re looking for inspiration, practical tools, and a reminder that it’s OK to start messy, this one’s for you. Book a free clarity call or join the Stay-at-Home Bookkeeper Academy - because your dream business really does start with one small step.If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

April 13, 202635 min

Just Give It a Go: Marketing and Mindset with Hannah Shea

Let’s be honest — figuring out marketing and new tech can feel a little daunting, especially if you’re shifting careers or building something fresh from scratch. But what if the secret is just being willing to say, “Sure, I’ll give it a go,” even if you’re not sure exactly how it’ll turn out?In this episode, we’re joined by Hannah Shea, our marketing program manager at the Stay-at-Home Bookkeeper Academy. Hannah’s journey didn’t start in a marketing office — she began as a musician and opera singer, learning how to pivot, try new things, and transfer her creative skills to supporting bookkeepers and building her own flexible career.We talk about:- The power of just saying yes (even if you’re nervous)- Marketing tips that actually work for bookkeepers today — including what to post on social and why simple, authentic video matters so much- Easy systems for organizing your content (no overthinking required)- How AI tools like ChatGPT and Claude can take the overwhelm out of content creation and bio writing- Embracing the pivot: why your past experience is never wasted, and how multiple income streams can support your dreamsIf you’re ready to build a business that fits your life, not the other way around — and maybe you need a little nudge to try something new — you’re in the right place.If you’re someone who wants more freedom, who’s tired of feeling stuck, or just ready to learn as you go, join us. And when you’re ready for real support and friendly accountability, book a clarity call or join the Stay-at-Home Bookkeeper Academy. This is your sign — just give it a go!If you're interested in the Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1