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

    1D AGO

    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 dreams If 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

    36 min
  2. CEO Thinking: How to Take Control of Your Time and Business

    APR 6

    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 ownerWhy being your own boss is less about perfection and more about learning as you goThe 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 ofIf 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 Academy, fill out this form we'll give you some details asap!! https://forms.monday.com/forms/703bc0857975139468aa8f2547977f4e?r=use1

    25 min
  3. Reinventing Success: How Kari Michelson Built Freedom, Flexibility, and Impact After Hollywood

    MAR 30

    Reinventing Success: How Kari Michelson Built Freedom, Flexibility, and Impact After Hollywood

    Welcome to the Stay At Home Bookkeeper podcast, where real stories about building freedom-based businesses take center stage! In this episode, Deanna Rogers sits down with her longtime friend and mentor, Kari Michelson, whose journey started as a child actress on a hit sitcom but led her to an impactful career as a speaker, consultant, and show host. Deanna Rogers and Kari Michelson dive into the heart of what it means to redefine success—leaving behind the glitz and grind for a life with more control, purpose, and flexibility. Kari shares her transformation story, from facing dark industry challenges and overcoming an eating disorder to discovering the joy of authentic storytelling, launching record-breaking product lines, and ultimately creating a business that lets her put family first. If you’ve ever felt torn between your career and your life—or wondered if you could become your own boss and work from anywhere—this episode is packed with encouragement, actionable tips, and real talk about the messy, magical process of creating your dream business. You’ll learn: The power of community and honest supportWhy “imperfect” action beats waiting for perfect confidenceHow to promote your unique story in ways that actually feel good- not salesyPractical steps to start showing up and sharing your passion Ready to design a business that fits your life? Grab your cup of coffee, settle in, and let’s get inspired. Your dream starts with just one step - let’s take it together!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

    40 min
  4. What Every Bookkeeper Needs to Know About Tax Strategy with Jim and Lorraine Conway

    MAR 23

    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
  5. 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
  6. 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
  7. 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
  8. 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
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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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