Amanda Chestnut
Founder, Money Mastery LLC: Creating space for the human work of advisory
Wilmington, North Carolina, United States
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Amanda Chestnut, JD, founded Money Mastery LLC to help small-business owners understand how their books, taxes, and decisions fit together. Based in southeastern North Carolina, she helps owners uncover problems, anticipate tax consequences, and make informed choices while there is still time to act. She understands that behind those decisions are families, livelihoods, and people carrying more responsibility than others often see.
An Accredited Business Accountant through the National Society of Accountants and an elite-level Advanced QuickBooks ProAdvisor, Amanda brings more than 20 years of experience. Her bachelor’s degree in social psychology informs her approach: useful advice starts with understanding the person who needs to use it.
Amanda is rethinking how an accounting firm operates, using her own practice as a testing ground for AI. She is building systems that take on reviews, track documents, and support communication, while questioning which processes and software still earn their place. She generously shares what she learns with fellow accountants. Her purpose is to create space for the work that requires human attention: sound judgment, difficult conversations, and helping someone feel understood enough to ask the next question.
A Brunswick County Chamber of Commerce Emerging Entrepreneur Award recipient and NC Project LEAD Entrepreneur Innovator Award nominee, Amanda is a Reframe Society Leader and certified in Exactly What to Say for Accountants.
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Connect the Dots: From AI Chats to Firm-Wide Leverage
The document is in the portal. The explanation is in an email. The decision was made in a meeting. And somehow, you’re still the glue holding it all together.
You’ve used AI to save time on individual tasks. The bigger unlock comes when those tasks connect—and you stop having to reconstruct the story every time something needs attention.
I’m not a coder. I’m an accounting firm owner who got tired of the communication and document chase and started building a different way to work.
In this session, I’ll open up the attention router I built in Claude and show how its layers work together. We’ll get into the practical details: folders and projects, firm context, Markdown instruction files, reusable skills built from existing procedures, and connections that bring information into the process.
Then we’ll connect the dots. A meeting commitment links to an outstanding request. The request gets an owner and a follow-up point. Relevant information comes together in a draft response. Skills that help with one task become building blocks for coordinated work across the firm.
We’ll explain how agents can select and use those skills, how triggers start the work, and where permissions and human approval belong. We’ll also examine the iterations behind the working system: what it missed, what it misunderstood, and the verification checks added to catch those gaps.
Using the ROUTE framework, you’ll design your own attention-router blueprint. You’ll leave with a practical build plan and a clearer picture of the leverage available when your firm’s knowledge, procedures, and information channels work together.
Expect a plain-spoken look under the hood, with room for questions and those “Wait—we could use this for…” moments.
Pull Up a Chair: AI That Finally Makes Sense
Somewhere between “agents,” “models,” and the fifth must-have tool, you stopped asking questions and started wondering whether you’d missed the beginning.
You haven’t missed your chance. Pull up a chair.
I’m not a coder. I’m an accounting firm owner who started with everyday problems and discovered how much AI could change the way my firm works. I teach the way I like to be taught: plain language, familiar examples, and room to stop and say, “Wait. Explain that part again.”
Whether you’ve barely started or tried AI and got a bland answer back, this session will help you find your footing—and see why this can be genuinely fun.
We’ll take one ordinary task and build on it, layer by layer. Start with a spoken brain dump. Let AI ask the questions you haven’t thought to answer. Turn those answers into a reusable brief about your firm. Use that context to create a better client communication, then turn the process into something you can use again.
Along the way, you’ll see how the pieces connect: less repeated explaining, more useful drafts, and new ways to put your experience to work. We’ll also catch mistakes, question assumptions, and identify where your judgment is essential.
The START framework will keep us grounded in what to do first, what to check, and what can wait. We’ll explain unfamiliar terms as they arise and address privacy and access before connecting tools or sharing information.
You’ll leave with a practical starting kit and ideas for your own practice. The goal is that moment when AI stops feeling like one more thing to learn and starts opening possibilities you’re excited to explore.
Intended Audience:
Accountants, bookkeepers, and tax professionals who feel overwhelmed by unfamiliar AI terminology and too many tool choices, or who have tried AI without seeing its practical value. Designed for people who want an approachable starting point and a clearer picture of what becomes possible.
Clean Client Exits: Boundaries, Bridges, and Risk Mitigation
You’ve decided to end the engagement. The client hasn’t decided to accept it.
They may plead for another chance, dispute an unpaid balance, or become intimidating. Meanwhile, one team member is still answering questions, another has promised additional work, and nobody has checked whether your powers of attorney remain active.
Difficult exits often begin with concerns we postpone addressing. When the ending comes, unresolved issues and inconsistent communication can blur responsibilities and create commitments the firm never intended to make.
Drawing on my legal education, insurance-defense experience as a law clerk, and client transitions in my own firm, this session connects critical conversations and professional boundaries to practical risk mitigation.
We’ll work through one realistic exit scenario involving strained expectations, unpaid fees, and resistance to the firm’s decision. Using the CLOSE framework, you’ll review a flawed exit plan, strengthen the client and team communication, and identify overlooked obligations.
We’ll create the exit checks by reverse engineering the engagement letter and onboarding process: what the firm promised, what authority and access it obtained, and what must be completed, transferred, withdrawn, or retained. Specific checks include filing deadlines, powers of attorney, information authorizations, stored credentials, and QuickBooks access and subscription control.
I’ll also demonstrate the disengagement skill I built in Claude to help organize those details and prepare communications, highlighting where human judgment and verification remain essential.
You’ll leave with language for holding boundaries without needlessly burning bridges and a practical process for keeping an emotional ending from becoming an open-ended engagement.
Intended Audience:
Firm owners, partners, managers, and client-service leaders responsible for difficult client conversations, team coordination, and client transitions.
Who Am I Without This Work?
A role changes. A position ends. Retirement becomes a real possibility. The practical question is “What happens next?” Underneath it may be a harder one: “Who am I now?”
One lesson from my grief training changed how I understand these moments: grief can be what we feel when we lose something, or experience a change, that we did not want. That can include familiar work, relationships, belonging, or a future we expected. Even a departure we choose can involve losses we weren't prepared for.
I know the fear and shame of losing a position and wondering whether I would find my footing again. Later, a mass departure from my firm and my own career crossroads challenged what I understood about leadership, relationships, and identity. My grief training and two years of leadership coaching helped me put words to those experiences.
Now AI is bringing questions about our professional futures into the room. Some people fear being pushed out. Others are considering retirement or leaving the profession and feel conflicted about letting go.
A central lesson guides this session: grief must be witnessed. We'll make room for those questions with empathy, acknowledging each person's experience without judging their response or rushing them toward an answer.
Using the CARE framework and career-transition exercises I have used myself, we'll practice critical conversations and explore identity, strengths, and possibilities beyond a current role. Whether you're supporting a colleague, advising a client, or considering your own next chapter, you're welcome here. Sharing is optional. You'll leave with a conversation guide and a practical next-step exercise that allows uncertainty alongside possibility.
AI Saved an Hour. Why Are You Still Exhausted? The REST Framework for Resilience
You finish faster, squeeze in one more client, and answer one more “quick question.” Somehow, the time you saved never becomes time for you.
AI can help us get more done. But people-pleasing, over-responsibility, and the discomfort of disappointing others can quickly claim whatever space it creates.
I learned the hard way while navigating a serious health crisis, a personal loss, and a major restructuring of my firm. AI helped me keep going. It also helped me overwork more efficiently. I had changed how the work got done without changing what I believed I had to carry.
Drawing on my background in social psychology, communication training, and lived experience, this session offers room to speak honestly about the weight beneath the workload. If you’re tired of being the dependable one who always finds a way, you’re welcome here. Sharing is optional, and there is no judgment about where you’re starting.
Using the REST framework, you’ll recognize the strain, examine the expectations behind it, practice saying what you need, and choose a restorative step. You’ll leave with words for a conversation you’ve been avoiding and a practical plan for protecting some of the time technology saves.
That space supports the foundational skills of good advisory: listening with empathy, asking questions with curiosity, exercising sound judgment, and having critical conversations with care.
This breakout is for Accounting, bookkeeping, and tax professionals, including firm owners, leaders, and team members. Especially relevant to those who find it difficult to say no, feel responsible for keeping everyone happy, or are getting more done with technology while still feeling stretched thin.
The Words Machines Can't Say: Talking Your Way Past the Four Fears Holding Your Firm Back
AI can prepare the return. It can't sit across from a nervous client, name a fee with confidence, or ask for the business. Those moments come down to what you say next, and for most accountants, fear is doing the talking.
This workshop tackles four fears that quietly cap firm growth: fear of selling, fear of pricing conversations, fear of rejection, and fear of AI replacing your value. For each, participants will learn why the fear shows up, what it sounds like in real client conversations, and the specific language that moves past it. Attendees will practice word-for-word frameworks, then adapt them to their own clients and services.
Participants will leave with a personal script library they can use Monday morning: how to explain their value in an AI world, quote fees without apologizing, handle "that's too expensive," and turn advisory opportunities into engagements without feeling like a salesperson.
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