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

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 confident

If 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!!
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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

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

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

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

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 Academy, fill out this form we'll give you some details asap!!
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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 support
• Why “imperfect” action beats waiting for perfect confidence
• How to promote your unique story in ways that actually feel good- not salesy
• Practical 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