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

    2D AGO

    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 game Feeling 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

    43 min
  2. From Overlooked to Unstoppable: Bold Ways Bookkeepers Can Stand Out Locally

    APR 27

    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=deanna865 If 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

    41 min
  3. The Power of Small Steps: Scott Bell’s Guide to Sustainable Business Growth

    APR 20

    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 freedom If 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

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

    APR 13

    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
  5. 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
  6. 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
  7. 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
  8. 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
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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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