The Stay-At-Home Bookkeeper Academy Podcast

Hosted by Bill & DeAnna Rogers

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Latest episode

Nov 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.

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50 recent

November 6, 202625 min

CEO Thinking: How to Take Control of Your Time and Business

Let’s be real—most of us have spent more time wondering “what if?” than dreaming about clocking in at some office for the rest of our lives. If you’re someone who wants more freedom, more flexibility, and work that actually fits your life, welcome to The Stay-at-Home Bookkeeper Podcast. In today’s episode, Emily and DeAnna get honest about one of the hardest—and most transformational—parts of starting your own business: making the leap from “employee” to CEO. We’re talking all about how to break out of task lists, self-doubt, and waiting for permission, and step into the driver’s seat of your life and work. Here’s what you’ll take away: What it really means to shift your mindset from employee to business owner Why being your own boss is less about perfection and more about learning as you go The power of getting comfortable with being uncomfortable (and why that’s a good thing!) Tips for protecting your why, claiming your time, and building a legacy you’re proud of If you’re tired of being stuck in a job that drains you, or you want to build a life-first business, this conversation is for you. Ready to stop waiting and start building a bookkeeping business that works for YOU? Book a free clarity call today or join us inside the Stay-at-Home Bookkeeper Academy. Let’s dive in! If you're interested in the chatting with us, you can talk with someone on our team about your goals, your situation, what it takes to get your bookkeeping business started (without any experience needed), etc. right here: https://calendly.com/the-stay-at-home-bookkeeper-academy/the-bookkeeper-academy-goals?utm_source=BuzzsproutPodcast Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

October 30, 202644 min

Stop Competing on Price: A Former Judge on Winning Clients Through Relationships

Dropping your price to land a client feels safe. It isn't. There's always someone who can go lower, and they can usually wait you out longer than you can. On this episode of Stay at Home Bookkeeper Podcast: Real Talk, DeAnna and Bill Rogers sit down with Roy Landers, an attorney, former judge, author, pastor and entrepreneur since age 12. Roy has spent decades negotiating across the table from other attorneys and watching people argue their case from the bench, and his advice for winning clients is surprisingly simple: listen more than you talk. Roy was raised by a single mom of eight who told her kids, "Don't ever tell me you can't." He sold homemade juice as a kid, worked all day and went to law school at night, and built plenty of businesses along the way, including a few that failed. His takeaway: there are no failures, only lessons. Today he's building a business with his daughter, helping veterans who own businesses get certified for federal contracting work. We discuss: Why Roy chooses to be a "go-giver" instead of a go-getter Listening, pausing and repeating back as a negotiation strategy A trial-prep exercise that helps with imposter syndrome before a big conversation How to show value before you have a long track record Why competing on price turns you into a commodity The 5 M's of marketing: message, market, media, measurement and ministry If sales calls make your stomach drop, or you've been tempted to undercut everyone just to land your first client, this conversation gives you a calmer way to think about both. You don't have to be the smoothest talker in the room. You have to be the one who listened. Subscribe, leave a review, and share this episode with the friend who keeps discounting their services to get a yes. Interested in starting your own bookkeeping business? Join us for our free virtual training on Tuesday: https://stayathomebookkeeper.co/livetraining Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

October 23, 202639 min

Start Messy, Keep Going: Sarah Wolf on Building a Business When Life Isn’t Perfect

You don't need a perfect plan to start. You need to start moving. But what do you do when your life looks nothing like the business you pictured as a kid? On this episode of Stay at Home Bookkeeper Podcast: Real Talk, Emily Kern and DeAnna Rogers sit down with Sara Wolfe, an entrepreneur and community builder who has coached women on six continents and now acquires businesses with her partner. Sara knew she wanted to be a businesswoman at seven years old. Life took a different route. She married young, homeschooled her kids, and later went through a season when she and her children were homeless. One moment at a grocery store register became her turning point. She started small by building a community for women entrepreneurs, moved into one-on-one coaching, and eventually discovered she didn't have to build everything from scratch. We discuss: Why it's easier to steer a moving car than a parked one Starting with community before you have a big budget The "not yet" habit that keeps your phone and to-do list from running your morning Open posture vs. bracing for impact on the hard days Why the early climb feels like a plane on the runway, and how comparison makes it worse What led Sara to buy businesses instead of always starting new ones If you're building a bookkeeping business from a less-than-perfect starting point, or you're stuck at a handful of clients wondering why nothing's moving, Sara's story is a reminder that messy progress still counts. So does the community you surround yourself with. Subscribe, leave a review, and share this episode with the friend who keeps waiting for the perfect time to start. Interested in starting your own bookkeeping business? Join us for our free virtual training on Tuesday: https://stayathomebookkeeper.co/livetraining Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

October 16, 202649 min

Marriage, Business & Boundaries: How Rachel and Dalton Left Their Jobs to Build a Business Together

You’re married. You’re business partners. And now you’re together 24/7. How do you build something meaningful without letting work take over your relationship? In this episode of Stay at Home Bookkeeper Podcast: Real Talk, DeAnna and Bill Rogers sit down with Rachel and Dalton of Big Sky Automation to talk about leaving their jobs and building a business together. Rachel and Dalton share their journey from side hustles in a tiny home to full-time entrepreneurship, including how they found their roles, learned to trust each other’s strengths, and handled doubts from family. We discuss: Taking the leap from employment to entrepreneurship Dividing responsibilities instead of overlapping on everything Communicating as spouses and business partners Setting boundaries when business follows you everywhere Choosing opportunities that fit your shared vision Celebrating small wins and making time to enjoy the life you’re building Whether you’re building with a spouse, a family member, or on your own, this conversation offers a practical reminder: clear roles, honest communication, and room for life outside of work matter. Subscribe, leave a review, and share this episode with someone you’d love to build something with. Interested in starting your own bookkeeping business? Join us for our free virtual training on Tuesday: https://stayathomebookkeeper.co/livetraining Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

October 9, 202629 min

20+ Years of Bookkeeping Lessons: Building a Business & Avoiding Costly Mistakes

What does it really take to build a successful bookkeeping business? And what are the financial mistakes that could be holding business owners back without them even realizing it? In this episode of Stay at Home Bookkeeper: Real Talk , hosts Emily Kern and DeAnna Rogers sit down with Kelly Callis, owner of Callis Bookkeeping , for an honest conversation about entrepreneurship, finding clients, knowing your worth, and the financial realities of running a business. Kelly shares how she went from working with CPAs to launching her own bookkeeping business, the fears she faced when starting out, and how a simple conversation landed her very first client, who's still with her more than 20 years later! But the conversation doesn't stop there. Drawing on her years of experience working with small businesses, Kelly pulls back the curtain on the bookkeeping mistakes she sees every day, from mixing personal and business expenses to relying on a bank balance to determine profitability. She also explains why even profitable businesses can struggle with cash flow and why putting off your bookkeeping can create bigger problems down the road. And if you've ever felt embarrassed about messy books or wondered whether it's time to bring in professional help, Kelly has some reassuring advice. Whether you're dreaming of starting your own bookkeeping business, working to grow one, or simply trying to get a better handle on your business finances, this episode is full of real stories, hard-earned lessons, and practical advice you can put to work. Because building a business isn't about knowing how to do everything yourself. It's about knowing your value, understanding your numbers, and surrounding yourself with the right people. Connect with Kelly Callis at Callis Bookkeeping: Website: http://www.callis-bookkeeping.com Email: kelly@callis-bookkeeping.com Facebook: https://www.facebook.com/CallisBookkeeping LinkedIn: https://www.linkedin.com/in/kelly-faulkner-callis-cpb Ready to build your own bookkeeping business? The Stay at Home Bookkeeper Academy helps everyday people learn how to start and grow a bookkeeping business from home, even without prior bookkeeping experience. Learn more: https://stayathomebookkeeper.com/ Enjoyed this conversation? Follow Stay at Home Bookkeeper: Real Talk so you never miss an episode, and share this one with a fellow entrepreneur or aspiring bookkeeper! Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

June 22, 202635 min

From Tragedy to Triumph: Finding Your Sparkle and Building Consistency with Helen Brahms

Let’s be honest—life as an entrepreneur (or dreamer, or caretaker, or just a regular human) isn’t always sunshine and spreadsheets. Sometimes it’s loss, grief, and the kinds of challenges you never see coming. In this episode, we sit down with Helen Brahms—a woman whose journey takes her from heartbreak and rock bottom to new adventures, daily triumphs, and yes, more sparkle than you’d think possible. If you’re someone who wants more freedom, but life keeps throwing curveballs—or if you just need some proof that transformation can happen, no matter where you start—this conversation is for you. We'll dig into the power of gratitude, the magic of simply taking a “half a shuffle” forward even when that’s all you've got, and why showing up with discipline (sticky notes included!) is the real secret to moving mountains in your business and life. Ready to get inspired, feel hopeful, and maybe laugh a little? Tune in. And if you’re listening and thinking, “Maybe I could do this…” then this is your sign: Book a free clarity call and let’s talk through what’s possible for your next chapter. Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

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 intimidating If 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. Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

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 energy If 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. Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

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 time So, 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! Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease

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 opportunities Belinda 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. Curious what a flexible bookkeeping career could look like for you? Register for our free virtual training, where we walk through what it takes to get your bookkeeping business started (no experience needed), right here: https://webinar.stayathomebookkeeper.com/flexiblecareer?utm_source=PodcastRelease&utm_medium=Description&utm_campaign=PodcastRelease