The Stay-At-Home Bookkeeper Academy Podcast

Tiffani Higgins
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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. 

  1. What Every Bookkeeper Needs to Know About Tax Strategy with Jim and Lorraine Conway

    2D AGO

    What Every Bookkeeper Needs to Know About Tax Strategy with Jim and Lorraine Conway

    Welcome back to the Stay At Home Bookkeeper podcast! In today’s episode, we’re pulling back the curtain on a game-changing topic that doesn’t get talked about enough—tax strategy—and what it really means for bookkeepers, business owners, and anyone building a freedom-based life. Deanna Rogers and Bill Rogers are joined by the powerhouse couple, Jim and Lorraine Conway, who have been working together for over 35 years (and married for 33!). They share their journey from financial advisors to full-time tax strategists, and get real about what it takes to work (and thrive!) with your spouse in business. More than just tax talk, this conversation is packed with insights about finding your lane in business partnerships, why the basics of tax strategy matter—even if you’re not wealthy—and how bookkeepers can become true heroes for their clients. Jim and Lorraine break down common misconceptions, real-life examples about deductible expenses (hello, meals and travel!), and powerful ways to add value as you grow your bookkeeping business. Whether you’re just starting out, thinking about leaving the 9-to-5, or looking for your next way to serve clients better, this episode is full of encouragement and practical, down-to-earth advice you can act on today. Want to follow Jim and Lorraine? Check out JCA ProGrowth Solutions on Facebook at www.facebook.com/progrowthfinancial Ready to learn how to build not just a flexible business, but a truly freedom-filled life? Let’s dive in! 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

    30 min
  2. Busy vs. Productive: How Bookkeepers Can Create Calm, Growth, and Work-Life Balance

    MAR 16

    Busy vs. Productive: How Bookkeepers Can Create Calm, Growth, and Work-Life Balance

    Ever feel exhausted by your business, but not actually seeing the growth to match? You’re definitely not alone - and this episode is for you. On today’s Stay at Home Bookkeeper podcast, Emily Kern and Deanna Rogers dive into one of the biggest struggles work-from-home entrepreneurs face: the battle between busy work and true productivity. They get real about that hamster-wheel feeling - when every day is packed, but your to-do list just grows and your goals stay out of reach. You’ll hear practical strategies for breaking free from “busyness,” like doing a simple time study, learning to set boundaries, and building actual systems so you’re proactive, not just putting out fires. There’s also a candid look at how tools like AI and time blocking can take the mental load off your plate, so you can focus on what actually moves your business forward. Both Emily Kern and Deanna Rogers share stories of tasks they used to do by hand - and the relief of finally automating or letting them go. If you’re tired of feeling overwhelmed, want real change, and dream of a business that gives you freedom - not just more work - jump in. You’ll walk away with mindset shifts and tangible tips to turn your hard work into real results. And if you’re wondering if a stay-at-home bookkeeping business could give you the life you want? This episode will help you figure out what “productive” really means to you, and how to start building it - one step at a time. Ready for that freedom? Let’s get into it. 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

    25 min
  3. Family, Flexibility, and Bookkeeping Success: Real Talk with Tracy Rosenberry

    MAR 9

    Family, Flexibility, and Bookkeeping Success: Real Talk with Tracy Rosenberry

    Ever wondered what it’s really like to build a business with your spouse, pivot when life throws you a curveball, or step into the world of bookkeeping—even if you’re not a numbers person? In this episode, Emily Kern and Deanna Rogers sit down with Tracy Rosenberry: business owner, Head of Education at the Stay At Home Bookkeeper Academy, and co-founder of Delightful Digits. You’ll hear the honest truth about navigating business with family, embracing the messy middle, and why it’s okay—not just possible—to change directions as you grow. Tracy Rosenberry opens up about how her initial dream (think: restaurant niche inspired by family life) evolved, why she finally pivoted away from taxes, and how she found new courage (and boundaries!) working alongside her husband. The conversation is packed with practical examples, from handling “imposter syndrome” when you’re just starting out, to using tools like AI to boost your confidence, communicate better, and save time. If you’re craving more flexibility, a supportive community, or just need that nudge to start even if you feel unprepared, this episode is for you. You’ll get real talk on the power of communication with clients, the importance of building relationships over being perfect, and the beauty of a business that grows with you—at any stage of life. Ready to hear stories of pivots, practical advice, a sprinkle of AI magic, and encouragement to take your first step (even if it’s messy)? Hit play, and get ready for inspiration you can actually use. And if you’re thinking, “Maybe I could do this…”—stick around for some straight-up encouragement and your next action 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

    47 min
  4. Juggling Work and Life: Intentional Routines for Home-Based Entrepreneurs

    MAR 2

    Juggling Work and Life: Intentional Routines for Home-Based Entrepreneurs

    Ever feel like working from home is more chaotic than calm? On this episode of the Stay at Home Bookkeeper podcast, Emily Kern and Deanna Rogers get real about what it actually takes to manage your time and stay productive when your home is your office. They share the good, the bad, and the sometimes hilarious realities of juggling laundry, emails, family - oh, and building your own business, all under one roof. You’ll hear their favorite time management strategies - like time blocking, intentional routines, and the difference between being busy and being truly productive. They open up about battling perfectionism, setting boundaries (with clients and yourself), and what to do when your day just goes off the rails (#resetrituals). Whether you’re thinking about launching a bookkeeping business, you’re already knee-deep in client emails, or you just want to make working from home… well, work for you - you’ll walk away with down-to-earth advice, encouragement, and a permission slip to take imperfect action. If you want more freedom, more balance, and more confidence in your ability to design a business (and a life) that fits you, this episode is your guide. Grab your coffee, settle in, and join the conversation! 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

    36 min
  5. Wealth Strategies for Women: Mastering Money, Mindset, and Business with Tamar Hermes

    FEB 23

    Wealth Strategies for Women: Mastering Money, Mindset, and Business with Tamar Hermes

    Welcome back to the Stay at Home Bookkeeper podcast! In today’s episode, Deanna Rogers sits down with her friend and powerhouse entrepreneur Tamar Hermes, the founder of Women Growing Wealth. Tamar Hermes shares her journey from climbing the corporate ladder in television to building financial freedom through real estate investing and guiding other women to do the same. If you’ve ever wondered how to turn business success into lasting personal wealth or if you keep asking yourself, “How do I make sure my hard work leads to real freedom?” - you’ll want to stick around. In this conversation, Tamar Hermes reveals the practical (yet often-overlooked) habits that every business owner should have, why managing your personal “wealth column” matters as much as your business income, and how to avoid the most common financial pitfalls that trip up even seasoned entrepreneurs. We’ll also dig into topics like building work-life balance, getting comfortable with imperfect starts, and making space for the ideas that really align with your dream life. This episode is packed with both wisdom and super-actionable tips that’ll help you step into the next level of freedom - whether you’re just getting started or already scaling your business. Ready for some real talk about what it takes to build a business and a life you love? Let’s dive in! 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

    41 min
  6. How Real Bookkeepers Start Their Day: Unfiltered Routines for Success and Sanity

    FEB 16

    How Real Bookkeepers Start Their Day: Unfiltered Routines for Success and Sanity

    Welcome back to the Stay at Home Bookkeeper podcast—where real talk meets real freedom. In this episode, Emily Kern and Deanna Rogers are breaking down the realities of work-from-home life, focusing on the power of a personalized morning routine. Forget the influencer-approved 5am hustle—this conversation gets honest about what it really takes to start your day on your own terms, whether that’s coffee from Costa Rica, a sticky note to-do list, or simply taking a quiet moment to scroll Facebook before the madness starts. You’ll hear stories of how routines can shape your day, why there’s no one-size-fits-all solution, and the little habits that help you stay centered—especially when you’re running a business from home. If you’re someone craving more freedom, flexibility, and a way to design work around your life (not the other way around), this episode is for you. Get ready for practical tips, relatable stories, and permission to find a routine that works for you. Grab your favorite drink, get comfortable, and let’s dive in! 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

    25 min
  7. From Dead-End Job to Family Business: Kristie Lawson’s Journey to Bookkeeper and Freedom

    FEB 9

    From Dead-End Job to Family Business: Kristie Lawson’s Journey to Bookkeeper and Freedom

    Welcome back to the Stay-at-Home Bookkeeper podcast! In today’s episode, we’re pulling back the curtain on what it really looks like to build a bookkeeping business from scratch - and why it’s so much more than just numbers. Emily Kern and Deanna Rogers sit down with Kristie Lawson, the powerhouse Student Success Coordinator at the Stay-at-Home Bookkeeper Academy, who shares her raw and inspiring journey from overworked, undervalued employee to fulfilled business owner (and homeschool mom of four!). Kristie dives into how she took the leap - even when it felt scary - and how she’s built a business for her family, with her family. You’ll hear real talk about: - The not-so-glamorous breaking point that sparked Kristie’s transformation, - What bookkeepers actually do (versus CPAs - and why both matter), - Building a business that fits your life, - How procrastination and sticky notes can go hand-in-hand with success, - The reality of learning-as-you-go and embracing imperfect action. If you’ve ever wondered if bookkeeping is really the door to more freedom and flexibility - or questioned if you’re “experienced enough” to make a change - this conversation is your sign that possibilities are closer than you think. Ready to see how real people create real freedom? Let’s dive in. 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

    36 min
  8. How to Build Your Bookkeeping Brand: Marketing, Referrals, and Real-Life Advice with James Lucente

    FEB 2

    How to Build Your Bookkeeping Brand: Marketing, Referrals, and Real-Life Advice with James Lucente

    On today’s episode of the Stay at Home Bookkeeper podcast, host Deanna Rogers sits down with marketing expert—and her longtime friend—James Lucente. If you’ve ever wondered how to start building your brand or get your bookkeeping business noticed online (even if you’re terrified of posting on social media), this conversation is for you. Together, they break down the real-life process of discovering your unique voice, leveraging AI tools like ChatGPT, and finding the confidence to put yourself out there—even when it feels awkward. You’ll hear practical stories about starting messy, leaning into community, and why giving back (yes, even for free sometimes) can lead to referrals that change everything. From using your phone to make compelling videos, to engaging authentically online, to building a business that feels good—not just profitable—you’ll pick up actionable marketing strategies and lots of encouragement. If you’re someone who dreams of breaking free from the 9-to-5, craves flexibility, or just wants to know how to get your first client as a stay-at-home bookkeeper, this episode will help you get started—no perfection required. Tune in to learn how to build your presence, attract clients you love, and grow your confidence one post at a time. And remember: if you’re ready to take the leap, book a free clarity call to see if the Stay-at-Home Bookkeeper Academy is your next 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

    42 min
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About

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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