The Successful Bookkeeper Podcast

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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

[00:00] Why bookkeepers are targets

[02:00] Craig's path from psychology to cybersecurity

[08:00] How AI changed phishing attacks

[11:00] Smishing, quishing and vishing explained

[15:00] Safe words and callback verification

[17:30] Are QR codes safe to scan?

[19:45] Password managers and passkeys

[24:30] Next-of-kin recovery and staff transitions

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:

Set a safe word with every client. Never publish it in email or any electronic format. If an urgent wire request comes in by phone and the caller can't give the safe word, "click, they hang up" and move on to an easier target.

Call back on a number you already trust. Use the one saved in your phone, not the one in the email, because attackers will swap in a number they answer themselves.

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

Cyberhoot

1Password

The Successful Bookkeeper: thesuccessfulbookkeeper.com (resources and links)

Part 2 of this conversation: business-side cybersecurity and preparing your team

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

[00:00] Opening Quote on Emotional Decisions

[01:12] Hunter's Background and Path to Sales

[04:30] Dos and Don'ts When Engaging Prospects

[07:00] Discovery Questions That Surface Real Pain

[10:30] Building Strategic Partnerships

[16:30] Cold Outreach and Research Tactics

[21:00] Using AI to Prepare for Sales Calls

[25:00] Why Deals Fall Apart: Lack of Discovery

[29:00] Handling the Pricing Conversation

[33:30] Follow-Up and the Free Financial Review

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

Connect with Hunter Rademacher on LinkedIn: search Hunter Rademacher (R-A-D-E-M-A-C-H-E-R) and send a DM — he's offering a free sales audit of your current sales process to listeners of this episode

CSI Accounting & Payroll

PureBookkeeping.com — the proven system to grow your bookkeeping business

The Successful Bookkeeper — free business-building resources

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.