Real Firms

You have about three months before tax season ramps up, and this is the time to get comfortable with AI. Rebecca Driscoll and Charlie Barmore talk through how to prepare yourself, your firm, and your clients for a tax season where AI generated emails, work papers, and documents show up far more often than they did this year.

Charlie shares the instructions he gives clients to paste into a Claude or ChatGPT project, so their AI knows how to work with him and how to write him a short, useful email. Rebecca makes the case for educating clients instead of being offended by what they send, pointing out that a client who hands you a fully filled out 1120-S still chose to give it to you and not the IRS.

They walk through where to start: a long walk in voice mode to brain dump your frustrations and goals, building one small tool only you will use, and testing work papers with synthetic data instead of client data. Rebecca tells how a client analyzer spreadsheet turned into an interactive tool and taught her about hosting, domains, and GitHub along the way, and Charlie explains why every bad output is a chance to fix the setup so it doesn’t happen again. Along the way: using AI as a thinking partner, telling it to stop agreeing with everything, and how what you learn could become a new advisory service for your clients.

This week’s starting point: go for a long walk with voice mode on, tell AI where your firm is today and where you want it to be by January 15, and brain dump everything before you try to plan anything.

Where to go next.

Experiment with AI alongside other accountants in AI Lab for Accountants (ALFA). For conversations about running your firm, clients, pricing, capacity, and what comes next, join The Collaboration Room (TCR).

Your firm needs two AI plans: one for next tax season and one for what you want the firm to become. Rebecca Driscoll and Charlie Barmore talk through how to improve the work you have to do now while making room to rethink your services, client relationships, and business model as AI changes accounting.

Rebecca shares how a coffee with another mom turned into a conversation about cash flow, forecasting, and the gap between knowing AI exists and having time to use it. Charlie explains how a client lunch led him to build a cash dashboard across multiple businesses, and why solving that problem opened the door to a new paid service.

They talk about planning for next tax season while rethinking the longer-term firm, finding opportunities beyond tax returns and monthly financials, and testing a new service with one willing client. Along the way: using AI as a thinking partner, asking how an existing offering could be 10X better, and finding peers who will help you experiment. They also compare notes on recent AI announcements and how Charlie tests new models with his own accounting examples.

This week’s starting point: write down how your firm actually works. Document your workflows, tech stack, and where information lives so you and your AI have a clearer foundation for deciding what to improve.

Experiment with AI alongside other accountants in AI Lab for Accountants (ALFA). For conversations about running your firm, clients, pricing, capacity, and what comes next, join The Collaboration Room (TCR).

We sat down right after meeting with a firm owner who runs a mostly 1040 practice, and he asked the question we keep hearing in ALFA, in TCR, and in almost every conversation with firm owners lately: what will my firm look like next year, and what should I be doing about it today? His answer was to make two plans, a short-term AI plan for the coming tax season and a longer view of what the work could look like two or three tax seasons out. That framing shaped this whole conversation.

We talk about trimming the software you're paying for but barely using, why Charlie would sort a 1040 book into buckets based on which clients are likely to stay as AI gets better at returns, and how bookkeepers can move up the value ladder with projections, analysis, and CFO-style work. Charlie shares how a lunch with a business client turned into a cash dashboard he built over a weekend and a higher fee the client didn't blink at. Rebecca shares a coffee shop conversation with a business owner that reminded her how much regular business owners need an accountant who is curious about their whole operation.

We also get into asking AI to 10x something you've already built, trying a new service on one willing client before rolling it out, using AI to figure out what you actually want your firm to be, and why it helps to work through all of this with people who say "yes, and" instead of "no." Plus a quick take on this week's OpenAI announcements and how to tell whether a new model is really better, including the benchmark Charlie runs on fake client data.

If you do one thing this week: write down how your firm actually runs, your workflows, your tech stack, and where information lives, so AI has something real to work with when you ask it how to make things better.

What happens when you tell AI the goal instead of the process? Rebecca Driscoll and Charlie Barmore talk about what it means to be an AI-native firm, why every firm needs its own North Star before deciding how deep to go, and why band-aiding AI onto your current tools is a fine place to start but probably not where you want to stay.

They also get practical about how Charlie sets up his "harness," using client folders and context files so Claude knows exactly who the client is and what needs to happen, how that compares to projects in Claude or ChatGPT, and how to keep client information current after every meeting. They close with one thing to try this week: ask your AI to audit your setup and tell you what it needs to do its best work.

ABOUT REAL FIRMS
Real Firms is Rebecca Driscoll, CPA, and Charlie Barmore, CPA, CFE, CVA, figuring out what the accounting firm of the future actually looks like.
Charlie explores what AI and new technology are making possible. Rebecca looks at how work is organized, how technology fits into the firm, and how decisions about clients, pricing, people, and boundaries affect the business.
Real Firms sits at the intersection of AI Lab for Accountants and The Collaboration Room: what’s becoming possible meets what it takes to run the firm.
Real Firms: https://realfirms.co
AI Lab for Accountants: https://ailabforaccountants.com
The Collaboration Room: https://thecollaborationroom.co

How do you get comfortable using AI in your firm? Start with the small things. Rebecca Driscoll and Charlie Barmore discuss how everyday experiments build confidence, why voice conversations are an easy entry point, and how sharing what you learn helps your team get started.

They also explore what happens when clients bring their own AI agents into the relationship, how staff training could change, and where new advisory services might fit.

ABOUT REAL FIRMS

Real Firms is Rebecca Driscoll, CPA, and Charlie Barmore, CPA, CFE, CVA, figuring out what the accounting firm of the future actually looks like.

Charlie explores what AI and new technology are making possible. Rebecca looks at how work is organized, how technology fits into the firm, and how decisions about clients, pricing, people, and boundaries affect the business.

Real Firms sits at the intersection of AI Lab for Accountants and The Collaboration Room: what’s becoming possible meets what it takes to run the firm.

Real Firms: https://realfirms.co
AI Lab for Accountants: https://ailabforaccountants.com
The Collaboration Room: https://thecollaborationroom.co

Clients are starting to assume AI made your work faster, so your price should go down. Rebecca Driscoll and Charlie Barmore, both CPAs who have owned firms, talk through why that is actually the opening you have been waiting for: the deliverable stays the same, but for the first time you have the capacity to make it worth more. From there: what "AI native" means versus bolting AI onto a legacy process, when to leave the chat window for Claude Code, how Charlie pits two models against each other to catch errors, how to set up your AI on day one so it explains things in accounting terms, and why your staff should be better at this than you are.

Sometimes we get too excited talking about what is actually happening inside real accounting firms. We were already twenty minutes into this conversation before we remembered to hit record... 

Charlie is running the AI Native Firm series inside The Collaboration Room starting this month, four live sessions on exactly this: what it means to be AI native and what firm owners should do now. TCR is $100 a month, cancel anytime: https://community.thecollaborationroom.co/checkout/tcr-community-membership

ABOUT REAL FIRMS

Real Firms is Rebecca Driscoll, CPA, and Charlie Barmore, CPA, CFE, CVA, figuring out what the accounting firm of the future actually looks like.

Charlie explores what AI and new technology are making possible. Rebecca looks at how work is organized, how technology fits into the firm, and how decisions about clients, pricing, people, and boundaries affect the business.

Real Firms sits at the intersection of AI Lab for Accountants and The Collaboration Room: what’s becoming possible meets what it takes to run the firm.

Real Firms: https://realfirms.co
AI Lab for Accountants: https://ailabforaccountants.com
The Collaboration Room: https://thecollaborationroom.co