The Successful Bookkeeper Podcast

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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

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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.

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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

[00:00] Opening quote on client value

[01:18] Welcome and guest introduction

[03:30] The provocative LinkedIn article

[06:30] Defining what bookkeeping really is

[10:00] Three times bookkeeping 'died'

[15:00] AI as shepherd, not replacement

[18:30] Who thrived through each shift

[23:00] Evaluating tech without chasing shiny objects

[27:30] Rising professionalism and community

[31:30] Biggest opportunity the profession must not miss

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

Lara Manton on LinkedIn — connect with Lara directly

ACE-XL Ltd — Lara's finance process consultancy for larger businesses

LJM Bookkeeping — Lara's UK bookkeeping practice

PureBookkeeping.com — episode sponsor, proven system for growing your bookkeeping business

thesuccessfulbookkeeper.com — free business-building resources

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

[00:00] Opening: Fear and Opportunity

[01:18] Alex Lee's Unlikely Path to AI

[04:18] The Future Is Still You

[08:00] Will AI Replace Bookkeepers?

[12:00] Crawl, Walk, Run: Getting Started

[16:30] AI Adoption Across the Profession

[19:30] Data Privacy and Security Checklist

[24:00] Vision for Accounting's Future

[27:00] About Truewind

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

Truewind — Alex's AI-powered accounting platform

The Successful Bookkeeper — show resources and guest information

PureBookkeeping — episode sponsor, proven system to grow your bookkeeping business

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'.

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Jon Sheldon has lived through more transitions than most people can imagine — Marine Corps infantry, corporate finance director, and now founder of Belleau Wood Coaching. This episode is a practical conversation about what it actually takes to lead yourself and your team well: getting clear on purpose, planning for what will go wrong, and building the kind of confidence that only comes from taking action. Whether you're just starting your bookkeeping practice or managing a growing team, there's something here for you.
Chapters
[00:00] Purpose as the Common Thread
[02:54] Jon's Background: Marines to Finance
[08:00] Life's Purpose vs. Purpose Right Now
[10:48] Accepting the Cost of Transition
[15:00] Contingency Plans Beat Burning Boats
[17:54] The Six-Step Decision Framework
[22:00] Failure, Resilience, and Confidence
[26:00] The Four-Pillar Performance Blueprint
[31:00] Accountability and Radical Honesty
[34:00] How to Connect with Jon
Purpose Is Not Just a Cliché
Jon believes purpose is the most overlooked driver in business — and in life. "Most people I run into don't ever take the time to, or have never taken the time to, really plan it out or think about what, how are they living a purposeful life?" It doesn't have to be a grand existential answer. Finding what fills you with purpose right now is enough to start leading better — yourself and the people around you.
Plan for What Will Go Wrong
One of the most practical ideas Jon brings from his Marine Corps days is what he calls "accepting the cost." Most people building a business focus on the vision and avoid thinking through what could go wrong — because they don't want to scare themselves out of it. Jon flips that: "Most battles are won with better contingency plans. That's how most missions are won — by thinking through the challenges and obstacles that are inevitably going to come." Knowing your worst-case scenarios in advance doesn't kill confidence. It creates it.
A Six-Step Decision Framework
Jon teaches a repeatable process he calls Clarity, Condition, Cost, Align, Act, Adapt. Get clear on what you're deciding. Do a gear check — do you have everything you need? Establish the cost of what could go wrong. Make sure your first action actually aligns with your goal. Act. Then adapt based on what you learn. "I've had the best plan and then the first action has nothing to do with pushing my business forward." The framework keeps that from happening.
Failure Is Part of the Deal
Jon is direct about this: failing is how you build the confidence to lead. "You might not hire the right person the first time. You might not make a great investment here or there. It's how you bounce back from that and get resilient that's going to really boost your confidence." If you're just getting started, expect some rough patches. If you have a clear purpose tied to where you're going, those rough patches are easier to push through — because the destination still matters.
The Four-Pillar Performance Blueprint
Jon works with every client through a four-pillar framework: Purpose (your why), Vision (a day-in-the-life picture of where you're headed, three years out), Ecosystem (who and what you're surrounding yourself with — including your tools and your workspace), and Motivators (what actually energizes you to take action). From there, his coaching is high accountability and action-driven: clients leave every session with a tracked action step, session notes, and metrics they've defined themselves. As Jon puts it, he's "tactfully tough and radically honest" — because most business owners don't have enough people in their corner telling them the truth.
Links mentioned
Belleau Wood Coaching website: belleauwood.coach
Instagram: @belleauwood_coaching
LinkedIn: Jonathan Sheldon (search "Jonathan Sheldon Belleau Wood Coaching")
Start With Why by Simon Sinek
About the guest
Jon Sheldon is the founder of Belleau Wood Coaching and a former Marine Corps infantryman who completed two back-to-back deployments to Iraq, leading 13 Marines through more than 200 combat missions. After leaving the military, he built a 14-year career in financial planning — running his own practice and then directing a regional team — before going full time into leadership coaching. He works with business owners and their teams on purpose, decision-making, and building the kind of resilient confidence that actually holds up when things get hard.
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'.