The Successful Bookkeeper Podcast

Hosted by Michael Palmer

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Nov 2026

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The Successful Bookkeeper Podcast is a weekly show to help increase your confidence, work smarter and build a business you love. Each week you'll listen to inspiring guests who will share their success secrets, so you can take your bookkeeping enterprise and life to another level. Some of them include New York Times Best-Selling Author of E-Myth, Michael E. Gerber, Pure Bookkeeping Co-Founder, Debbie Roberts, the host of The Productive Woman podcast, Laura McClellan and the author of *I Know How She Does It*, Laura Vanderkam. If you're a bookkeeping business owner who is looking for an uplifting, entertaining and informative podcast exclusively for YOU then you have arrived at the right place! Get ready because your journey towards success begins — now. Your Host Michael Palmer is an acclaimed business coach who has helped hundreds of bookkeepers across the world push through their fears and exponentially grow their businesses and achieve the quality of life they've always wanted.

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November 12, 2026Episode 55940 min

EP559: John McClane - Confidence Follows The Tools: Why AI-Using Bookkeepers Expect Growth With A Human In The Loop

See what the team at The Successful Bookkeeper has on right now → Plooto CEO John McClane joins Louie Prosperi to walk through the company's recent survey of more than 550 Canadian bookkeeping and accounting businesses. The headline is an optimistic one: 81% of respondents expect to grow in 2027, and the firms most confident about it are the ones already putting technology and AI to work. John also explains what "agentic" AI means, why the payments-to-reconciliation gap is where bookkeepers lose hours, and what peers say you should do before 2027 arrives. Chapters [00:00] Welcome and John's background [01:30] Why Plooto ran the survey [03:20] Why AI users expect more growth [08:00] Agentic AI explained simply [13:00] Accuracy, security, and starting safely [16:00] Capacity, hiring, and burnout [21:00] Strengths and gaps in firms [25:00] Payments, reconciliation, and integrations [29:00] Peer advice for 2027 [32:30] Big takeaways and where to learn more Confidence follows the tools Respondents were more upbeat about their own businesses than the economy: 81% expect growth, against 60% who feel positive about the Canadian economy. A quarter expect growth of 20% or more. The split between users and non-users is the striking part. 93% of respondents using AI across several workflows expect to grow, compared with 52% of those not using AI. John's read is that the optimism comes from agency: "If you're engaging with it, it's exciting. And if you're really hesitant to engage with it, then it's kind of concerning." Firms that name tech adoption as a strength came in near 90%, against about 80% overall. Agentic AI explained, and why a human stays in the loop Louie asked John to unpack the "agent" language, and the answer is practical. The same model behind a chatbot can now work in a browser or inside professional software, such as classifying expenses and handing you a draft to approve instead of making you do the line-by-line work. John points out that traditional software is deterministic while large language models are statistical and can still hallucinate. His advice is to "strike that right balance and have a human being in the loop, especially before you get into something like actually moving money." For hesitant firms, trying AI inside software you already trust is a good first step. Accuracy, security, and starting with rules-based work The survey shows enthusiasm paired with caution. 40% of respondents named accuracy and reliability as their top concern, and 37% named data security and client confidentiality. John calls that healthy for a profession that answers for the numbers. His suggested order of operations is to start with predictable, auditable, rules-based work like payments, then layer AI on top. As Louie put it, garbage in, garbage out. Capacity, hiring, and burnout 76% of respondents are prioritizing client acquisition over hiring. John's explanation is that automation is freeing capacity, so firms can add service lines and clients without staffing up. One customer, Marilyn Henschel of 2450 Solutions, saves at least 30 hours a month by automating payments and expects to double her business next year without hiring. John also stresses that "staff turnover is actually the number one driver of client turnover," so giving the team room to breathe protects client relationships. Louie added that spare capacity makes it easier to absorb a departure. Strong on relationships, short on operations Firms rated client relationships (42%), pricing and profitability, and staff expertise (35%) as their top strengths. Technology adoption and operational efficiency each landed at 27% and were also named among the most important areas to improve. The payments data shows the gap: 47% say clients pay digitally, but only about a third say those clients reconcile digitally. John's tip is to choose systems that talk to each other and to ask any vendor to demo reconciliation, including returns and failed payments, not just data import. 87% of respondents want to automate at least one core payments workflow next year. Advice for 2027 The advice respondents gave their peers was consistent: Train your team and plan rollouts so new tools get used. Use the time you save for clients and strategic work. Put safeguards in place, review outputs, and protect client data. Start small and build confidence. Keep your people at the center, because "technology's not going to replace your team." Links mentioned Plooto: plooto.com Download the survey report: plooto.com/2027report Plooto page for Successful Bookkeeper listeners and demo booking: plooto.com/TSB The Successful Bookkeeper: thesuccessfulbookkeeper.com About the guest John McClane is the CEO of Plooto, a payments automation platform serving bookkeeping and accounting firms and their small and medium business clients in Canada. He has spent nearly 25 years in business software and payments, based in Silicon Valley, working with companies from small businesses to large enterprises. Plooto offers two-way sync with QuickBooks Online and Desktop, Xero, and NetSuite. 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'.

November 10, 2026Episode 55834 min

EP558: Sharon Toerek - Stop Setting And Forgetting: Giving Your Client Agreements A Regular Checkup

See what the team at The Successful Bookkeeper has on right now → Most of us have a client agreement that was written once, borrowed from somewhere, or generated in a hurry, and then never touched again. In this episode, attorney Sharon Toerek explains why that "set it and forget it" habit is one of the biggest gaps she sees in professional service firms, and what a practical annual checkup looks like. Her work is with marketing agencies, but the lessons carry straight over to bookkeeping and accounting practices. Chapters [00:00] Why agreements need a temperature check [01:15] Sharon's path to founding Legal + Creative [04:30] Biggest blind spots in service firms [08:00] How often to review client agreements [12:00] Preparing your business model for counsel [16:00] Online terms versus signed engagements [20:00] Choosing a legal advisor in your industry [23:00] Niching as a business development strategy [26:00] Progress, not perfection, with your legals [28:00] Where to find Sharon The set-and-forget problem Sharon's biggest observation about service firm owners is that they move fast and skip the proactive work. "It's not very sexy to slow down and make sure that you've got all of your legal foundation or your process in place," she says, but not revisiting it "ends up costing you more time and money in the long run." The most common missed opportunity is the standard agreement itself, whether that's with clients, independent contractors, employees, or strategic partners. She calls a temperature check on those documents "a major opportunity gap" that is probably universal across professional service firms. What to review in your agreements Sharon's rule of thumb is to look at your evergreen agreements at least annually. She walks through the areas worth checking: Intellectual property ownership, especially if you reuse your own IP across multiple clients Fair competition covenants, such as clients poaching your staff or your staff poaching your clients Payment terms, and language that lets you recover collection costs if you have to chase unpaid fees Data protection, if you touch confidential or privacy-protected client data Liability limits that match the amount of risk you actually take on AI use, so clients understand how and when your firm uses it On AI, she is blunt: if you haven't received AI-created work product from a client, "I would love to meet you, because we get them every day and we're a law firm." Getting ready to talk to your lawyer Before anyone drafts or refreshes your contracts, your advisor needs to understand your business model: how you charge, what your proposals look like, whether you bill by project or by the hour. Sharon asks her own clients for two or three recent proposals so she can see how they talk about, price, and scope their services. She also pushes back on the idea that shorter is better. Her view is that an agreement "should be as long as it needs to be to cover the areas of potential exposure or risk." She adds that clients are just as unlikely to be put off by 13 pages as by 3, and that every clause should have a reason your lawyer can walk you through. Online terms versus a real engagement agreement Michael asked whether a firm can simply post its terms online and link to them. Sharon says that can work when the terms are technically deep and lengthy, ideally with a plain-English summary alongside. For most service engagements, though, clients still use a regular contract, signed digitally. The goal is not "gotcha contracting" but an agreement both sides actually understand. Choosing an advisor and the power of a niche Sharon suggests asking prospective lawyers what share of their practice is in your industry, whether they are active in it, and whether they publish or speak on it. She spends her own time at the conferences her clients attend, not at lawyer events, so she knows the challenges they face. Michael points out that this is also a model for bookkeepers choosing a niche. Sharon agrees: with AI changing every profession, deep industry knowledge is how you show the human value in the relationship. A niche, in her words, "makes you better at what you do," makes business easier to find, and makes the work more enjoyable. Progress, not perfection For anyone who suspects their legal foundation is a mess, Sharon's advice mirrors what bookkeepers tell clients about their books. Start where you are, find an advisor who will meet you there, and don't wait. "You pay now or you pay later," she says, and paying now usually costs less than waiting for a problem to show up. Links mentioned Legal + Creative (Toerek Law): legalandcreative.com The Innovative Agency podcast, hosted by Sharon Toerek Sharon Toerek on LinkedIn (T-O-E-R-E-K) The Successful Bookkeeper: thesuccessfulbookkeeper.com About the guest Sharon Toerek is the founder and owner of Toerek Law, which does business as Legal + Creative. About 13 years ago, after time at a large firm and at two entrepreneurial law firms, she started a practice serving independent marketing agencies across the US. Her firm focuses on intellectual property, contract development and negotiation, marketing law compliance, and AI governance. She also hosts The Innovative Agency podcast. 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'.

November 3, 2026Episode 55739 min

EP557: Laura Vanderkam - Time Abundance Is A Story: Zooming Out To Find Space During Busy Seasons

See what the team at The Successful Bookkeeper has on right now → Tax deadlines, month-end, and a dozen clients who all need something at once make "I don't have enough time" feel like plain fact. Laura Vanderkam, author of Big Time: A Simple Path to Time Abundance , returns to the show to argue that time scarcity is a story, and that a different story is more useful even when you're slammed. Her ideas are practical and easy to test: zoom out, plan like a ringmaster, protect your own priorities first, and track your time the way you'd track any other resource. Chapters [00:00] Meet the ringmaster: episode preview [01:30] Laura's fascination with how we spend time [04:00] Why time scarcity is just a story [09:00] Zooming out to the week and year [14:00] The ringmaster mindset: complexity, not chaos [19:00] Pay yourself first with your time [25:00] Why cramming tasks backfires [29:00] Small steps, War and Peace, little bets [34:00] What time tracking reveals [41:00] Resources and a gift idea for clients Zoom out from the day to the week and the year When the day you're in is packed, Laura suggests looking at a bigger window. "We don't only have one day. Most of us live our lives in kind of cycles of weeks." Zooming out shows you that things don't have to happen daily or at the same time every day. That might mean a 45-minute gym session on Tuesday morning and a 20-minute walk on Thursday, even in a crunch week. Zoom out to the full 8,760 hours of a year and a brutal deadline season looks like one season among several. She uses her own choir schedule as an example: one very full week, balanced by a summer with no rehearsals at all. Be the ringmaster, not the one buried in chaos Laura makes the case that a real circus is "the most orderly thing you will ever see." Complexity and chaos are not the same, and you can have a lot going on without it being chaotic. She suggests managing three rings (career, relationships, and self), doing a weekly planning session to look at what's running in each, and thinking ahead about what might go wrong so there's a net under every act. Michael adds that a ringmaster is enjoying the show, and Laura agrees: "A good circus is managed for delight." The point is to put fun in your schedule too. Pay yourself first with your time Bookkeepers often build the schedule around client requests and squeeze their own priorities into whatever is left. Laura compares this to saving money: if you save what's left at month-end, there usually isn't anything. She suggests blocking an hour or so at the start of your workday for your own goals before you open client email. If mornings don't work, try keeping Tuesdays and Thursdays protected. She also draws a line between being responsive and being constantly available. "There is such a huge space between being instantly responsive and being one of those weird people who won't get back to people for a week." Michael adds that setting clear expectations with clients takes pressure off you. Stop cramming tasks into every spare minute One thing that feeds the feeling of scarcity is trying to do a productive little task in every open moment. Laura recommends keeping a running list of small tasks and plowing through them in a single 30-minute block at the end of the day. That frees up the gaps between meetings for a real break, like a short walk outside, which leaves you more rejuvenated than booking a flight or answering a personal email would. Michael notes how rarely we let ourselves be bored, quiet, or still. Small steps and little bets on big goals Whether you want to hire, build a new system, or add advisory services, Laura says any big project is a series of small steps. Break it down until there's no resistance, put the steps in your calendar, and keep going. Her own example is reading War and Peace one chapter a day for 361 days. She pairs this with "little bets": try something small, see how it goes, and keep or drop it. For example, send four feelers a week to grow your network. Some won't go anywhere, but over a year you may end up with ten solid new connections. Track your time like any other resource Laura tracks her own time on a weekly spreadsheet with half-hour blocks and recommends every busy person try it for a week. Logs usually disprove the catastrophic stories we tell ourselves. If you worked 55 hours and slept 55 hours, there are still 58 waking hours left in the week. She describes a client whose log showed a clear hour and a quarter at night that vanished into wandering and tiredness because she hadn't picked anything she wanted to do. Michael points out that bookkeepers will recognize it as "mystery spend" for time. Links mentioned Big Time: A Simple Path to Time Abundance by Laura Vanderkam Laura's website: lauravanderkam.com Free time trackers (Google Sheets, Excel, and more): lauravanderkam.com/manage-your-time Before Breakfast , Laura's short daily podcast on productivity and mindfulness Signed stickers for client gifts (US and Canada): email laura@lauravanderkam.com Previous episodes with Laura on The Successful Bookkeeper About the guest Laura Vanderkam is an author and speaker who studies how people use their time. She is the author of Big Time: A Simple Path to Time Abundance and several other books on time management. She hosts the daily podcast Before Breakfast , and she has tracked her own time for over a decade and worked with hundreds of people on theirs. 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'.

October 27, 2026Episode 55635 min

EP556: Dickson Wasake - Every Job Needs A Bookkeeper: A CPA's Case For Confidence In Your Industry

See what the team at The Successful Bookkeeper has on right now → Dickson Wasake has worked from Uganda to the Bahamas, the UK, Canada and now Illinois, with stops at PwC, Baker Tilly and Deloitte's national office. Today he runs Jedidiah CPA, and he says plainly that he can't do his work without a bookkeeper on the team. In this conversation he tells bookkeepers what a CPA looks for, what raises a red flag, and how to build the kind of partnership that brings referrals your way. Chapters [00:00] Every job needs a bookkeeper [01:10] Dickson's global career path [04:00] Leaving a big firm in 10 days [07:00] What makes a great bookkeeper [11:00] Red flags and asking for help [15:00] CPA and bookkeeper as partners [19:00] Audit readiness all year long [23:00] Balance sheet and building confidence [27:00] Reconciled versus decision ready [31:00] Vetting new partners and finding Dickson The leap from big firm to your own practice When private equity bought his large CPA firm, Dickson had 10 days to decide whether to stay on in a changed role or go out on his own. He calls it "extremely, extremely tough," especially as a family man, but three-plus years later his reaction is "why didn't I do this earlier?" What he values most is the freedom and the diversity of cash flows. He also has a message for solo bookkeepers who doubt themselves: "Someone will always need bookkeeping support. There is no job I do without needing a bookkeeper." What a great bookkeeper looks like to a CPA Getting the basics right, meaning regular reconciliations and clean bookkeeping, is the starting point. What sets the best bookkeepers apart is being proactive: flagging items early and doing what they said they'd do. If they can't get back to him today, they say so, and then they follow up on the day they promised. Dickson also names the opposite behaviors that signal trouble: Assuming things and posting entries without checking in, such as expensing a capital purchase Not being "humble enough to ask for help," which he does himself all the time Waiting until the last minute, or letting reconciliations slip two or three months Michael adds that communication is a small-business survival skill, and that a system for tracking incoming messages beats good intentions. A partnership, not a turf war Dickson has never had friction over who does what. He knows his own strength is helping clients make unstructured decisions, and he needs a bookkeeper to tell him what has happened in the numbers. He shares the story of a bookkeeping firm owner who wrote a memo laying out a messy audit client's problems, and who became his first call whenever another client needed a bookkeeper. On building the confidence to speak up, he compares it to a good marriage: find someone you trust, "that even when you get it wrong, they lift you up and not tear you down." Audit ready all year, and decision ready every month Drawing on his Deloitte quality review work, Dickson calls audit readiness "a mindset": could someone understand your work without you there to explain it? In practice that means supporting documents uploaded for entries, a monthly close, and thinking about controls over payments, system access and adjustments. He also shares a "secret": when books are messy, the fastest fix is the balance sheet, because a balance is a matter of fact. He also separates reconciled from decision ready. A bank rec can tie out perfectly while the client sits in overdraft month after month, and "a balance sheet can balance and still be fundamentally wrong." Vetting a new bookkeeper With a bookkeeper he hasn't worked with, Dickson treats it like a job interview and listens to the questions they ask. Asking how a client likes to be contacted, whether by WhatsApp, phone or email, tells him he may have someone to refer business to. After that, it comes down to routine: reply to messages and don't ghost. If the first one or two months go well, he says, you can have a long-term relationship. Links mentioned Jedidiah CPA PLLC (search "Jedidiah CPA"): website with blog and service details Jedidiah CPA on LinkedIn Jedidiah CPA on Substack thesuccessfulbookkeeper.com About the guest Dickson Wasake is a partner at Jedidiah CPA PLLC, based in Illinois about an hour from downtown Chicago. He began his career at PwC in Uganda, became an audit partner at Baker Tilly in the UK after 13 years, and later served in Deloitte's national office in Canada, where he worked on audit risk and quality. He now advises small business clients and works closely with bookkeeping firms. 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'.

October 22, 2026Episode 55551 min

EP555: Jessica McKellar - Spotlight: Iron Man Suit For Accountants: Automating The Month-End Close With AI Tools

See what the team at The Successful Bookkeeper has on right now → 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 [01:30] Jessica's background and Pilot's origin [04:00] The Iron Man suit and LLMs [07:00] How Meridian works with your ledger [11:40] What firms should delegate to AI [14:10] Hallucinations and deterministic structure [18:20] Cleanup work and messy onboarding [22:10] Broken feeds and sync monitoring [25:00] Reviewing work and firm visibility [28:00] Staff culture and $1M portfolios [31:00] Data security and privacy 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 Meridian: meridian.pilot.com Pilot: pilot.com The Successful Bookkeeper: thesuccessfulbookkeeper.com 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'.

October 20, 2026Episode 55427 min

EP554: Craig Taylor - Cyber Literacy Is Just Common Sense: Training Your Team To Spot Social Engineering Attacks

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 [01:00] How often should you change passwords? [04:00] Passkeys and the human firewall [07:00] Why cyber literacy should be taught [09:00] ClickFix: the paste-a-command attack [12:00] The phishing rubric and two simple rules [16:00] Rewarding good behavior, not punishing [20:00] Gamification and AI-powered phishing [23:00] What cybersecurity training really costs [26:00] Where to start: risk assessments [28:00] CyberHoot trial and listener offer 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 CyberHoot: cyberhoot.com (book a demo; free 30-day trial) Free individual training: cyberhoot.com/individuals Sales contact: sales@cyberhoot.com Listener offer: mention The Successful Bookkeeper for 20% off your first year of CyberHoot services Part one of the conversation with Craig Taylor (previous episode) More resources: thesuccessfulbookkeeper.com 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'.

October 13, 2026Episode 55328 min

EP553: Craig Taylor - You Are A Prime Target: Why Bookkeepers Must Understand Modern Cyber Threats

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 [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'.

October 6, 2026Episode 55243 min

EP552: David Priemer - Sell the human, not the data: Why clients still need you in an AI world

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'.

September 29, 2026Episode 55140 min

EP551: Debra Kilsheimer - Beyond The Numbers: Why AI Makes Your Expertise More Valuable

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'.

September 22, 2026Episode 55032 min

EP550: Hunter Rademacher - Sell The Pain: How To Close More Bookkeeping Deals With Ease

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. Here’s a special gift for YOU. Visit Plooto.com/TSB and try it for FREE for two months! That’s a FREE 30-day trial, plus an extra free month for Successful Bookkeeper podcast listeners! Don’t miss out, sign up TODAY! 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'.