The Successful Bookkeeper Podcast

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Jessica McKellar has spent ten years proving that bookkeeping can be automated to a high degree, first by building an accounting firm as a test lab and now by packaging that technology for other firms as Meridian. In this Spotlight episode she walks Louie Prosperi through what an autonomous month-end close looks like, where AI belongs in a firm's workflows, and what it does to review time, staff morale, and security.

Chapters

From test lab to Meridian

Jessica and her co-founder began by writing software to help with their own month-end close, then spent a decade building Pilot as a place to stress-test automation against nearly 4,000 client businesses a month. Her shorthand for the first version is "the Iron Man suit for an accountant", with a human operating it. About 18 months ago, newer LLMs let them take the accountant out of the suit and plug in AI for an end-to-end close. Her motive for releasing it to other firms is simple: "I can't reach every small business owner myself."

What Meridian actually does

Meridian has four pieces: recurring work written as a checklist and executed in software, delegation of ad hoc tasks, an optional client portal, and team and firm management. It sits on top of your existing QuickBooks or Xero with no migration, posts directly to the GL, and inherits and rolls forward your supporting schedules. You can run the default close checklist out of the box, or customize a firm-level checklist down to the task level per client.

Keeping AI honest

Jessica would not "directly plug Claude into a client's GL and say have at it on the month-end close". That is too open-ended, with too few checks and too little visibility. In Meridian, work like reconciliations and schedule roll-forwards is deterministic software doing the math, and AI isn't asked to invent an answer. She advises firms building their own setup to decide what must happen the same way every time and what can be left to a model's judgment. Structure also surfaces the issues worth a client conversation, such as a payroll liability that isn't clearing or an invoice payment posted with no record behind it.

Cleanup work and broken feeds

Jessica describes onboarding a client with no business bank accounts, 800 receipts in multiple currencies, and incorrect Xero financials. She delegated the catch-up books as an ad hoc task. Meridian flagged duplicates, asked how to handle currency conversion, and called out receipts with no amounts. It finished in about two hours while she ate dinner with her kids. On data feeds, Meridian supports native GL feeds, Plaid-style third-party syncs, and statement uploads, and it can reveal a broken sync through balance sheet checks, like cash going out with no offsetting liability.

Review, capacity, and the team experience

If the operational work is done by software, the human time shifts to review, and clean books make for a faster review. Meridian leaves notes on why items aren't clearing and records client preferences in the checklist, which Louie, a reviewer who always asks staff to "show your work", appreciated. Pilot's internal target is $1 million in client revenue per production accountant. Jessica says the team feedback is "oh my gosh, this is so much better", and that after eight years of some clients always getting the short straw on deadlines, late closes no longer happen. Less context walks out the door when staff change, and PTO and turnover are easier to absorb.

Security and privacy

Meridian works on a principle of least access, and you can use it without storing data in it at all. Client data is not fed back into foundation models as training data. Jessica's larger point is that most security risk comes from a firm's own habits, such as password storage, credential rotation when employees leave, and who can download personal information, and less from the close automation tool itself.

Links mentioned

About the guest

Jessica McKellar is the co-founder and CEO of Pilot, where she helps shape how AI and technology are changing bookkeeping and accounting. She has a background in technology and engineering and has worked with her co-founder for nearly 20 years, since they met in the computer club at school. She still maintains a $500,000 client portfolio herself to stay close to the technology.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.

See what the team at The Successful Bookkeeper has on right now →

In the finale of his two-part conversation with Michael Palmer, Craig Taylor turns from personal security to the business side: how to train a team so that one rushed click doesn't become a ransomware headache. Craig is the founder and CEO of CyberHoot, and his message is encouraging. Most of what protects your firm is simple habits, taught in a way people want to repeat.

Chapters

Do you really need to change that password?

Michael opens with a question many of us get from clients: how often should the one password be changed? Craig's answer is "Never," as long as it's a long passphrase (20 characters or more) protecting your password manager and there's no sign of a breach. NIST rescinded its old 90-day rotation advice because "humans cheat," tacking on a year or a month and making the password easier for attackers to guess. Forced resets mostly create "entropy and chaos" and lockouts. Michael adds that passkeys have become the easy path, noting "it's more secure and it's faster."

Cyber literacy is the missing basic skill

Craig points out that we graduate people from school with reading, writing, and arithmetic but no cyber literacy, even though everyone runs their working life on a computer. He sees most breaches tracing back to human mistakes, and the fix is a program inside the company. His core rule for spotting trouble is to be suspicious whenever someone asks you to act "urgently, emotionally, with authority or secrecy," and to verify out of band by calling a known good number.

ClickFix and the attacks to know about now

Craig's example of the moment is ClickFix, which the FBI issued an advisory on in September. A website asks you to prove you're human, then tells you to open a command prompt and paste in something it supplied. That pasted command is a PowerShell script that hands over remote access. His rule: "No human test has ever asked you to paste something onto your computer." He also mentions last year's smishing wave (the fake toll-violation texts) and says CyberHoot produces 12 new videos a year to cover whatever attackers did in the previous 12 months.

Carrots, not sticks: training that changes behavior

Phishing remains the top way into firms of 500 people or fewer, according to the Verizon breach report, and Craig says two habits stop nearly all of it: check the sender closely for one-letter differences like typosquatting, and call the person when a request is strange. He argues that punishing clicks doesn't change behavior. With a psychology background and years as a hockey coach, he favors positive reinforcement, such as taking your top performers to lunch instead of calling out the laggards at an all-hands. Gamification (levels, avatars, an anonymous leaderboard) turns training from work into play, and the repetition builds muscle memory: "go check the sender because I've done it 50 times."

What it costs and where to start

Craig puts training at roughly $1.50 to $3 per employee per month, against a breach that can cost "a million times" more, and notes that insurers increasingly require training and non-punitive phishing simulations before they'll cover a claim. If you can only do one thing, adopt a password manager and turn on MFA. Next comes awareness training, and after that a risk assessment from a fractional or virtual CISO so you spend limited time and money on your biggest risks first, whether administrative, technical, or physical.

Links mentioned

About the guest

Craig Taylor is the CEO and founder of CyberHoot, a company that builds cybersecurity awareness training and positive-reinforcement phishing simulations for businesses of all sizes. A lifelong cybersecurity professional with a psychology background and a level 4 certified hockey coach, he has built CyberHoot around the idea that people learn secure habits best when they're rewarded for them. The company recently received a patent for its approach to positive-reinforcement phishing simulation.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.

See what the team at The Successful Bookkeeper has on right now →

Bookkeepers sit right next to the money, and that makes them a favorite target for financially motivated hackers. In part one of this two-part conversation, Cyberhoot founder and CEO Craig Taylor explains how AI has changed the threats landing in your inbox, your texts and your phone calls. He also gives you a short list of habits that shut most of those attacks down. Craig started in cybersecurity 30 years ago with a psychology degree, and his focus is on behavior change rather than fear and shame.

Chapters

Why bookkeepers are a prime target

Craig is blunt about it: "Bookkeeping is the purse strings of the companies you're supporting." If you pay bills, wire funds or manage the financials of multiple companies, you are, in his words, "not just a little one, you're a prime target." Five years ago the attack was a clumsy gift card request with bad grammar. Today it can come from a breached inbox, with perfect spelling, the right branding, and urgency, authority and secrecy built in to rush you past your instincts.

Phishing, smishing, quishing and vishing

Craig walks through the whole family of scams: phishing (email), smishing (SMS text), quishing (QR code phishing) and vishing (voice). Fake toll violation texts and stickers pasted over parking meter QR codes are everyday examples. Voice is the scariest, because AI can clone a voice from two or three seconds of audio, and a call that sounds like someone you know carries built-in trust. As Craig puts it, the common thread is "getting you to react and do something financially without proper validation."

Verify before you act

The fix is the same whatever the delivery method: verify the identity of the requester. Craig's two best tips for bookkeepers:

Michael adds his own version of this: when someone calls claiming to be the bank or the government, look up the general number yourself and call in.

Are QR codes safe to scan?

Craig says scanning a QR code on your phone is relatively benign unless something is attacking the phone itself, but you should know where the code came from. A menu at a busy restaurant is fine, while a code on a telephone pole is not. If the next screen asks for a credit card when you only wanted an event date, stop.

Make this the week you adopt a password manager

If you do one thing after this episode, Craig says, make it a password manager: "It allows you to create unique passwords everywhere you go." It will save you from some phishing attacks, and from changing passwords in 25, 50 or 100 places when one account is breached. Craig also recommends passkeys, which can't be stolen and reused, and says to protect the manager itself with multi-factor authentication. Both he and Michael use 1Password. Set up the next-of-kin recovery feature so a trusted person can regain access after a delay. It also helps when staff change jobs: the next person can pick up the client accounts the last one managed.

Links mentioned

About the guest

Craig Taylor is the founder and CEO of Cyberhoot, a company that makes cybersecurity simpler, more practical and easier to manage for small and mid-sized businesses. He began his career in cybersecurity roughly 30 years ago after studying psychology in Guelph, Ontario, and worked at several Fortune 500 companies, including a large bank, Computer Sciences Corporation and Vistaprint. Twelve years ago he founded Cyberhoot to teach cyber literacy in a way people enjoy, using positive reinforcement rather than punishment and shame.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.

See what the team at The Successful Bookkeeper has on right now →

If you've ever worried that AI will make bookkeepers obsolete, this episode is the antidote. David Priemer, founder of Cerebral Selling and a scientist-turned-sales expert, makes a compelling case that the human experience of working with a trusted professional is the product — and no app can replicate it. Michael Palmer and David dig into how bookkeepers can identify what clients truly value, tell better stories, and attract new business without feeling like a salesperson.

Chapters

• [00:00] Guest intro and origin story
• [03:42] From research scientist to sales expert
• [08:00] Why meteorologists still matter
• [12:00] The forecast is not the product
• [16:00] What clients actually buy from you
• [21:00] The one-thing question
• [26:00] Using one client story effectively
• [32:00] Selling if you hate selling
• [37:00] Building a belief-led message
• [43:00] Resources and book recommendations

The Meteorologist Lesson: The Forecast Isn't the Product

David opens with a striking analogy: anyone can check a weather app, yet millions still watch meteorologists on TV. Why? Context, trust, and the reassurance of another human being. "When you hire a bookkeeper, you're not hiring a machine to run the books for you and give you the answer," David explains. "You're paying another human being to care about your business, to help you grow, and bring all of their experience and expertise to help you avoid some of the pitfalls." The data — like the forecast — is just the starting point. The experience of working with a professional is what clients are actually buying.

Ask the One Thing Question

Most bookkeepers sell the technical side of what they do. But when clients are asked why they love their service providers, they rarely mention technical skill. They talk about responsiveness, feeling heard, and getting proactive advice. David's fix is refreshingly simple: ask one question. "What's one thing you find most valuable about our meetings?" Framing it around a process rather than yourself removes the awkwardness and focuses the client's mind. The answers you collect — even from just one or two clients — are legitimate and powerful material for marketing and prospecting conversations.

You Don't Need Statistical Significance

One of David's most freeing pieces of advice: you don't need 100 data points to craft a point of view or share a client story. "Don't worry about having statistically significant feedback," he says. "A couple of data points that allow you to go out to the world and say, here's some of the things I've heard my clients say about why they value working with me — that is very powerful." For bookkeepers who are wired to get things exactly right, this is a meaningful permission slip to tell real stories and share real observations without waiting for a perfect sample size.

Lead With What You Believe

For bookkeepers who hate the idea of selling, David offers a way in that doesn't feel like a pitch: lead with what you believe. Inspired by how Phil Knight talked about running — not shoes — and how Steve Jobs described changing the world before mentioning a product, David encourages bookkeepers to articulate the problem they see in the world and why it matters. "Beliefs are very powerful and intoxicating," he says. The one trap to avoid: sounding like everyone else. A belief statement needs an edge — a named problem or a clear "enemy" — to cut through the noise and stick in a prospective client's mind.

Three Ways to Sell If You Hate Selling

David distills his approach into three practical moves any bookkeeper can take: lead with what you believe, tell more client stories, and create content that does the selling for you. That last point has an unexpected bonus — roughly a third of the new clients who find David now come through AI-powered searches, simply because he has published enough content that reflects his distinct point of view. A digital footprint built on real beliefs and real client experiences doesn't just attract people; it also sharpens your own thinking. "The act of writing and crystallizing your point of view is very powerful for you," David notes — not just your audience.

Links Mentioned

• Cerebral Selling website — free blogs, resources, and information on David's books and training
• Sell the Way You Buy by David Priemer — available on Amazon, Audible, and Kindle
• To Sell Is Human by Daniel Pink — referenced during the discussion on sales perception
• Shoe Dog by Phil Knight — referenced on leading with belief
• David Priemer on LinkedIn — subscribe to his LinkedIn newsletter

About the Guest

David Priemer is the founder and Chief Sales Scientist at Cerebral Selling. A former research scientist who fell into sales during the dot-com boom, David went on to lead sales teams at four high-growth tech companies — including five years at Salesforce running small business sales for the Eastern US. For the past nine years he has run his own practice, teaching science- and empathy-based selling to companies around the world. He is the author of Sell the Way You Buy and writes a widely read newsletter on modern selling. Find him at cerebralselling.com.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.

See what the team at The Successful Bookkeeper has on right now →

Debra Kilsheimer has been in the accounting profession for 45 years, and she has never been more excited about its future. In this episode, she and Michael Palmer dig into what AI actually means for bookkeepers right now — not as a threat, but as a tool that clears away the task work and makes room for the conversations clients have always needed. If you have been wondering how to position your firm in an AI world, this episode is a practical place to start.

Chapters

• [00:00] Opening Hook on AI and Jobs
• [01:18] Welcome and Guest Introductions
• [03:30] Blazer Accounting: An AI-Native Firm
• [08:00] Pivoting From Task Work to Advisory
• [13:00] The Doctor Analogy and Client Conversations
• [18:00] Winning Clients With Sample Reports
• [23:00] Real Workflow Wins With AI Tools
• [28:00] Human Connection AI Cannot Replace
• [32:00] How to Start Small With AI
• [35:00] Closing Thoughts and Resources

The Shift From Task Work to Expertise

Debra's core message is simple: if you are only selling data entry and reconciliations, AI can replicate that. But if you are selling interpretation, insight, and relationship, no machine touches you. "If all you're selling is getting the numbers on a piece of paper, Chat will take your job," she says. The opportunity for bookkeepers is to move confidently into the role they have always wanted — explaining what the numbers mean and helping clients build the business and life they are after.

Building an AI-Native Firm

Debra and her colleague Donna Reed launched Blazer Accounting (getblazer.ai) specifically to test what an AI-first practice looks like in the real world. Their premise: bookkeeping should be free, because the machines now handle the transactional work. What that frees up is time for advisory — the higher-value conversations clients genuinely want to pay for. She also described concrete workflow wins, from having Claude automatically process PDF sales reports into a standardized template, to using AI to track tip payments from a hair salon's texted receipts before weekly payroll runs.

Winning New Clients With Sample Advisory Reports

One of the most actionable ideas in this episode is Debra's approach to prospect meetings. Before sitting down with a potential restaurant client, she uses AI to generate a sample monthly advisory report — using anonymized data from an existing client in the same industry — so the prospect can see exactly what working with her looks like. "They literally will sign on the spot," she says. "We're getting clients at like twice the pay that we were getting before. Because they've never had this. Never." It reframes the conversation away from transaction counts and toward outcomes.

The Human Element AI Cannot Replace

Debra is enthusiastic about AI, but she is equally clear about what it cannot do. It has no soul, no personal connection, and no real understanding of what a client wants out of their life. She draws the analogy of WebMD versus a doctor: a symptom checker might give you the right answer, but you still want a human to look you in the eye, ask the right questions, and catch what the algorithm missed. "You give your clients a connection that AI cannot give them," she says. "AI is just data — it's not the personal connection that only you can give."

How to Get Started Without Getting Overwhelmed

For bookkeepers who are not yet using AI tools, Debra's advice is to start small and stay curious. Pick one task — a bank rec that won't foot, a client report you want to draft — and try it. She recommends using Claude for number-heavy work and ChatGPT for writing and communication tasks. Most importantly, she says, don't compare your progress to anyone else's. "You are in your journey with this where you are. And where you are is great."

Links Mentioned

• Blazer Accounting — getblazer.ai
• Bookkeepers on Fire (YouTube channel with Donna Reed) — live every Tuesday at 3 p.m.
• Behind the Scenes Financials — Debra's traditional accounting firm
• Deb Liberate — Debra's speaking and consulting brand
• Women Who Count conference — upcoming keynote
• Reframe stage, Miami — upcoming speaking appearance
• The Woodard Report and OnPay — publications Debra writes for
• PureBookkeeping.com — episode sponsor

About the Guest

Debra Kilsheimer is an accounting professional, speaker, and founder of Deb Liberate, where she helps accountants and bookkeepers price their services, communicate their value, and lead with confidence. She is co-owner of Behind the Scenes Financials alongside her husband Hal, and co-founded Blazer Accounting, an AI-native firm, with Donna Reed. She also co-hosts the Bookkeepers on Fire YouTube channel and writes regularly for The Woodard Report and OnPay. Debra is based in Port Orange, Florida, and can be found on LinkedIn.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.

See what the team at The Successful Bookkeeper has on right now →

Hunter Rademacher has closed roughly 250 bookkeeping, payroll, and accounting deals in five years as an Account Executive at CSI Accounting & Payroll. In this conversation with guest host Louie Crossberry, Hunter shares the practical sales framework he uses every day — the kind of thinking that bookkeepers rarely get exposure to, but desperately need when it comes to winning new clients and holding on to good-fit ones.

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Chapters

Stop Talking About Your Services First

The most common mistake Hunter sees bookkeepers make is diving straight into what they do — features, software, deliverables — before the prospect has even explained their situation. Business owners often think of bookkeeping as a necessary evil, so opening with a feature list gives them nothing to connect with emotionally. "Tell me about your business" is the simple opener Hunter uses to let prospects surface their own pain. From there, the questions go deeper, and the prospect usually does most of the talking.

It's an Emotional Decision, Not a Logical One

Hunter is direct about something that trips up a lot of number-focused professionals: "People don't know that it's an emotional decision. And us accountants and bookkeepers especially think everything's logical and it should make sense." He's lost deals that were clear no-brainers on paper — the prospect just wasn't emotionally bought in. The fix is digging past surface-level answers to find the real pain, then being explicit about how you'll take that pain away.

Building Strategic Partnerships That Actually Send Referrals

CPAs get all the attention, but Hunter finds that other bookkeepers, business bankers, and consultants are often overlooked and highly valuable. His key insight is that a great strategic partner isn't just someone who'll trade referrals — it's someone who genuinely needs clean, timely financials to do their own job well. When reaching out cold, a vague "I'd love to work together" won't cut it. Instead, Hunter ties his outreach to something timely and specific: a filing deadline, a common client pain, a real reason they should care right now.

Pricing: Give a Range Early, Then Offer Options

Hunter pushes back on the old advice to hide pricing until the very end. Today's business owners research before they call, so stalling on price can feel evasive. He recommends giving an honest range early ("generally somewhere between $500 and $1,000 for a business your size") and explaining the factors that move the number up or down. When it comes to the proposal itself, presenting three service tiers shifts the conversation from "do I want to hire you?" to "which option fits me best?" — a much easier question for a prospect to answer.

The Follow-Up: Give Something Worth Coming Back For

When a prospect says "call me later," Hunter's move is to offer a free financial review — a look at their current books that delivers real value regardless of whether they sign on. "I want everybody that meets with me to have a great experience," he says. Even prospects who don't become clients often leave a Google review or send a referral. Building that reputation for genuine helpfulness, consistently, is what compounds into a full pipeline over time.

Links Mentioned

About the Guest

Hunter Rademacher is an Account Executive at CSI Accounting & Payroll in Minnesota, where he has spent five-plus years closing bookkeeping, payroll, and accounting engagements for small businesses ranging from $250K to $10M in revenue. With a background in finance and early experience at ADP, Hunter brings a rare combination of numbers fluency and genuine sales craft to the bookkeeping world.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.

See what the team at The Successful Bookkeeper has on right now →

If you have ever wondered what it actually looks like to build AI into your accounting practice — not in theory, but day-to-day — this episode is for you. Sam Leon, CPA and founder of TaxWeave, joined guest host Louie Prosperity to share exactly how he went from experimenting with ChatGPT to building his own secure AI platform for tax professionals. The conversation is practical, honest about the risks, and full of ideas you can act on right away.

Chapters

• [00:00] Introduction and Sam's Background
• [02:45] Why Sam Chose Claude Over Others
• [06:30] Claude Code: Beyond Just Chatting
• [09:30] Workflow Automation for Bookkeepers
• [12:30] The Data Security Problem
• [16:30] Building TaxWeave as a Secure Platform
• [20:00] Top AI Tasks to Tackle First
• [24:00] Keeping Up as AI Models Evolve
• [26:30] How Sam Checks His AI Outputs
• [28:30] Where to Find Sam and TaxWeave

From Curiosity to Real Workflows

Sam has been watching technology waves roll through the accounting profession for years — cryptocurrency, machine learning, practice management software. When AI chatbots arrived, he started testing them immediately, but it was a specific feature of Claude that changed how he worked: the ability to connect the tool directly to files on his computer. "That's how I got started with a lot of the more time-saving workflows that I was doing," he explains. The shift from chatting with AI to feeding it real documents opened the door to genuine time savings rather than novelty.

The Tasks Best Suited for Automation

Sam is direct about where AI earns its keep: document summarization, transaction categorization, and building QuickBooks rules. He recently spoke with a bookkeeper who used AI to generate an extensive list of transaction rules that could be imported straight into QuickBooks — a task that would have taken hours to build manually. His broader advice is to start with tasks that are data-heavy and repeatable, then layer AI on top of the tools you already use rather than replacing them outright.

Handling Sensitive Data the Right Way

This is where Sam slows down and gets careful, and so should you. For tax professionals in the US, IRS Code Section 7216 governs what client information can be shared with third-party systems — and most AI platforms have not yet been through the kind of SOC 2 certification process that established tax software has. Sam's personal rule: never upload anything containing Social Security numbers, EINs, or last names. For bookkeeping work, he sees a slightly lower barrier since transaction lists are often less personally identifying, but the principle holds. "Being more cautious than not — if you're unsure about it, probably take another step to make sure that information really doesn't have any personal identifying information on it." Upgrading to a Teams or Business plan on these platforms also adds a layer of data protection over personal accounts.

Building TaxWeave: From Workaround to Platform

The manual redaction problem — using Adobe to black out client details before running documents through AI — was slow and error-prone. That frustration pushed Sam to start building TaxWeave, a platform designed to handle the redaction automatically inside a secure environment, then run AI workflows on the cleaned documents. He built the initial prototype using Claude Code, which lets you describe what you want in plain language and generates the underlying code. "The barrier where you had to understand how to do that — it's removing that," he says. TaxWeave currently focuses on tax practice project management and client organization, with AI workflow integration being the layer built on top.

Keeping Up as the Models Keep Changing

AI models update constantly, and Sam's advice is to treat your workflows the same way you treat your engagement letters — review them periodically and adjust. He recommends using the Projects feature in Claude to maintain context across sessions, and revisiting your saved instructions whenever a new model version drops. You can even ask the AI itself what needs updating. For quality control, Sam still does his own research to verify AI-generated answers and checks outputs manually, paying attention over time to where the tool is weakest. "You can start to see what it's weaker on — what kind of things does it always miss — and what you can start trusting it with."

Links Mentioned

• TaxWeave: taxweave.ai
• Sam Leon on LinkedIn: search Samuel Leon CPA
• Claude (Anthropic): claude.ai
• PureBookkeeping: purebookkeeping.com
• Pluto (sponsor): pluto.com/tsb

About the Guest

Sam Leon is a CPA with 14 years of experience in tax accounting, specializing in corporate tax, startup tax issues, R&D credits, and individual returns. After building his solo firm, The Millennial CPA, he was recognized in the 2026 Accounting Today Best Firms for Technology Awards. He is currently developing TaxWeave, an AI-powered platform built specifically for tax practices, and is active in conversations across the profession about safe, practical uses of AI in accounting.

See what the team at The Successful Bookkeeper has on right now →

If you work 8-plus hours a day in front of a screen, your body is paying a price you may not fully see yet. In this episode, host Michael Palmer welcomes back nutritionist, TV host, and bestselling author Julie Daniluk for a frank conversation about what sedentary desk work is actually doing to bookkeepers' bodies — and, more importantly, what you can do about it starting today.

Chapters

• [00:00] Standing desk setup intro
• [01:37] Julie's plane crash recovery
• [03:54] Why sitting harms your body
• [07:00] Walking pads and movement snacks
• [09:48] Diagnosing your energy crashes
• [12:00] Continuous glucose monitors explained
• [17:00] Oura Ring and sleep tracking
• [21:00] Hidden energy thieves and diet
• [26:00] Ketones, brain fog, and yerba mate
• [30:00] LumaBody program and resources

Sitting Is the New Smoking

The phrase sounds dramatic until you hear what the research actually shows. "Sitting still for 8 hours a day is absolutely horrendous for your health," Julie explains. "You end up with very poor blood sugar control. It reduces your insulin sensitivity. It's hard on your heart, and it certainly reduces your circulation." The solution, she argues, isn't to stretch after work — it's to stop sitting so much in the first place. A desk topper that converts any standard surface into a standing workspace, combined with a compact walking pad (now as small as 2.5 feet long), can let you move your legs while you work without disrupting your typing rhythm. Alternating between a standing position and a balance ball chair throughout the day adds an unexpected core workout on top of the circulation benefits.

Movement Snacks and the Hourly Reset

Julie recommends treating movement the way many bookkeepers treat their billable time — in structured intervals. "Every hour you should be taking a small movement break," she says, whether that's 50 squats, calf raises, arm swings, or even just tapping your feet under the desk. She calls these "movement snacks," and the research behind them is clear: brief bouts of muscle activity pull blood sugar down, restore circulation, and fight the metabolic slowdown that comes with prolonged stillness. Pets help too — Julie walks her dog twice a day and counts an energetic ball-throwing session in the backyard as a legitimate movement break.

Tracking Your Metabolic Health

One of the most practical tools discussed in this episode is the continuous glucose monitor (CGM) — a small microchip worn on the back of the arm that pairs with a smartphone app to show real-time blood sugar readings throughout the day. No doctor's prescription required; they're available at most drugstores. Julie uses them regularly with clients and consistently finds surprises: smoothies, fruit-bottomed yogurt, and white rice can spike blood sugar just as sharply as obvious offenders like donuts. "It's going to give you charts and graphs to show you" exactly which foods cause peaks and crashes — and the crashes, she notes, are when fatigue, brain fog, and headaches hit hardest. The Oura Ring comes up as a complementary tracker for sleep quality, with Julie crediting mouth taping and acupuncture for doubling her nightly deep sleep.

Hidden Energy Thieves

Beyond movement, Julie identifies several drains that busy bookkeepers rarely connect to their afternoon slumps. Liquid calories — think blended coffee drinks topping 700 calories — don't register as fullness the way solid food does, so they spike insulin without satisfying hunger. Ultra-processed foods borrow nutrients like B vitamins, zinc, and chromium from your body's own reserves just to metabolize their empty carbohydrates, leaving you with less energy than you started with. Food sensitivities to gluten, corn, soy, or refined sugar can trigger an immune response that feels like pure exhaustion. And caffeine, she clarifies, doesn't give you energy — it suppresses adenosine, your body's fatigue signal, which is a very different thing. Her recommended alternative: yerba mate, which naturally stimulates GLP-1, reduces appetite, and delivers gentler stimulation without wrecking sleep.

Fueling Your Brain Differently

For bookkeepers struggling with brain fog, Julie points to ketones as an underused fuel source. When sugar intake drops, the liver produces ketones that can power the brain with remarkable clarity. "In the absence of sugar, how extraordinary my focus and memory really can be," she says, drawing on her own experience managing ADHD through nutrition. Therapeutic ketone powders and medium-chain triglycerides (from coconut products) offer a way to access this fuel without committing to a strict ketogenic diet. She also advocates for a protein-forward breakfast — a batch-cooked frittata made with a dozen eggs, roasted peppers, olives, and feta — as a practical way to stabilize blood sugar from the first hour of the workday and push carbohydrates to the evening, when they support sleep rather than afternoon crashes.

Links Mentioned

• Desk topper / standing desk riser — links to be added in episode resources
• Walking pad (compact) — links to be added in episode resources
• Continuous glucose monitor (CGM) — available at major drugstores; pairs with a smartphone app
• Oura Ring — ouraring.com
• LumaBody metabolic health program — juliedaniluk.com
• The Successful Bookkeeper community — community.thesuccessfulbookkeeper.com

About the Guest

Julie Daniluk is a registered nutritionist, TV host, and bestselling author whose work focuses on anti-inflammatory nutrition and metabolic health. She is the Program Director of LumaBody, a 12-week coaching program designed to help people reduce visceral fat, lower inflammatory markers, and build lasting energy through food and lifestyle changes. After recovering from a serious plane incident in Vancouver, Julie brings a deeply personal as well as professional perspective to walking her talk every single day. Find her at juliedaniluk.com and on social media at @JulieDaniluk.

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Lara Manton has a gift for reframing panic as possibility. The founder of ACE-XL Ltd and a 15-year UK bookkeeping veteran, Lara delivered a talk at Accountex titled I've Watched Bookkeeping Die 3 Times — and in this episode she brings that same clear-eyed optimism to Michael Palmer. If you've been anxious about AI or wondering whether your role still matters, this conversation will shift your thinking.

Chapters

Three "Deaths" That Were Actually Rebirths

Lara's three moments of supposed bookkeeping extinction track neatly with major industry shifts: the cloud and OCR revolution, COVID forcing everyone to work remotely, and now the rise of AI agents. Each time, the prediction was the same — software will replace the bookkeeper. Each time, the profession adapted and came out doing more meaningful work. "Every time the software changes," Lara says, "it changes what bookkeepers do. It changes the nature of bookkeeping, maybe not what we do, but how we do it."

The Core Job Has Never Changed

Strip away the tools and the underlying mission is the same it has always been: get accurate data to help businesses make decisions. Lara argues that AI and automation simply speed up the data-gathering part, which frees bookkeepers to spend more time on the part that actually matters to clients. "The rewarding thing isn't entering data," she says. "The rewarding thing is understanding a business and helping a business owner. And that bit doesn't change."

Humanity Is the Competitive Advantage

The bookkeepers who thrived through every disruption shared one trait: they stayed curious about their clients. Lara makes the case that asking the right questions — specific to each business, not generic ones — is where the real value lives. "You can learn to ask the right questions, not the questions that everyone asks, but the right questions for that business. And then that's where you can start to add value. Because unless you actually relate those numbers back to the business itself and what they're trying to achieve, those numbers are gonna mean nothing to them." She warns that if you communicate like a robot, AI will eventually be able to replace you — but the innately human skills of listening, pattern recognition, and relationship-building are much harder to replicate.

Thinking Clearly About AI Tools

Lara draws a sharp line between AI accounting tools and accounting tools with AI built in. The former often lack foundational accounting knowledge; the latter layer intelligence on top of proven principles. She shared a real example: a client ran their VAT return through Claude and came back with a list of confused questions — because the AI didn't understand international reverse charge VAT. "It's about shepherding that information and reviewing the information rather than necessarily doing the data entry, but being aware of the other things that matter to a business owner." The lesson: use AI to augment your expertise, not to bypass the need for it.

A Rising Tide for the Whole Profession

Lara sees bookkeeping's public profile improving — driven partly by institutional efforts in the UK to bring bookkeeping into university curricula, and partly by accountants increasingly recognising bookkeepers as collaborative partners rather than a cheaper alternative. She also points to the bookkeeping community's culture of sharing as a quiet competitive strength. "Bookkeepers talk to one another. We don't gatekeep in the same way. We share information quite freely." That generosity of knowledge, she believes, is one of the things that will carry the profession forward — and attract software companies who want to build better products with practitioner input.

Links Mentioned

About the Guest

Lara Manton is the founder of ACE-XL Ltd and runs LJM Bookkeeping, a UK-based practice working with limited companies and service-based businesses. A two-time Xero Award winner — including Xero's first UK Bookkeeper / Small Firm of the Year — Lara sits on the ICB's Advisory Board and chairs their Tech Board. She has spoken at every major UK accounting event, including Accountex, and works with approximately 50 clients worldwide across outsourced finance and bookkeeping engagements.

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If you've been watching the AI wave roll in and wondering what it means for your bookkeeping practice, this episode is for you. Alex Lee, co-founder and CEO of Truewind, brings a clear-eyed perspective grounded in three and a half years of building AI tools specifically for accountants. His message is direct: the future of accounting has always been about you, and that isn't changing.

Chapters

The Work That Has Always Mattered

Alex draws a useful historical line — from carving debits and credits in limestone, to paper ledgers, to file cabinets, to cloud software, and now AI. "I see AI as the next iteration of technology that may shape how accountants are doing the work," he says. "But ultimately, the work of the accountants is the same." What AI does is create space for bookkeepers to spend more time on the things that are genuinely hard to automate: being a trusted advisor, being a real business partner, and — as Alex puts it — shaking hands and looking someone in the eye. Those things don't disappear no matter how good the models get.

The Spreadsheet Comparison Worth Remembering

When the fear of replacement comes up — and it does — Alex points to a pattern that has played out before. When spreadsheets arrived, people predicted mass job losses in accounting. Instead, the profession grew. Some small business owners did start managing their own five-line chart of accounts, and some will use AI to handle basic recordkeeping themselves. But that's not your client. "As accountants, it puts you in a very unique position to elevate yourself in terms of your AI skills and demonstrate to businesses, I know how to use this tool exceptionally well." The expertise gap has always been the value. AI doesn't close that gap — it widens it in your favor if you lean in.

A Crawl, Walk, Run Framework for Getting Started

Alex is practical about adoption. Start by picking one AI tool you've already heard of — maybe tried once — and use it for everyday tasks: drafting a client email, writing a performance review, planning a trip. Get comfortable at that level before adding complexity. Walking looks like connecting your AI to your Slack, email, or call recordings and asking it to synthesize information — summarizing client pain points before a proposal, for example. Running is letting AI handle a meaningful portion of your day-to-day operations. "Just get started," Alex says. "Over time, get more sophisticated, and then over time, let it be the primary operating system for you."

Handling Data Privacy the Right Way

Financial data demands careful handling, and Alex doesn't gloss over it. His checklist for vetting any AI vendor: confirm they are SOC 2 Type 2 compliant with a reputable auditor (not a quick rubber-stamp), verify that data privacy agreements exist between your vendor and the underlying model providers like OpenAI or Anthropic, and look for a genuine philosophy of data protection — not just a claim on a website. For teams that are still nervous about connecting client data to AI tools, his advice mirrors the crawl-walk-run approach: start by using AI internally with your own team's Slack and shared drives. Build confidence there before expanding to client-facing workflows.

A Bigger Demand for Accountants Is Coming

Alex's outlook for the next one to five years is genuinely optimistic. He sees AI acting as a catalyst for what he calls a "Cambrian explosion of demand for accounting." As business models shift from billable hours toward fixed-fee engagements and technology enables firms to handle more clients with the same headcount, he expects more businesses — not fewer — to seek out qualified accounting professionals. "Accountants can get more done with less, driving an influx of demand for what accounting firms can provide." The firms positioning themselves now, building AI literacy and deepening client relationships, are the ones that will be ready to capture that demand.

Links Mentioned

About the Guest

Alex Lee is the co-founder and CEO of Truewind, an AI-powered accounting platform built for accounting firms and corporate finance teams. Before founding Truewind, Alex worked as an aerospace engineer at Boeing, spent time in venture capital, and built a financial planning and analysis company. Truewind launched in the same month as ChatGPT and has spent the past three and a half years building what Alex describes as an "agentic workspace" for accountants — integrating with QuickBooks Online, Sage Intacct, and NetSuite to help teams cut close time by 30 to 50%. You can reach Alex directly on LinkedIn or learn more at truewind.ai.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast and co-founder of Pure Bookkeeping and The Successful Bookkeeper. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.