The Successful Bookkeeper Podcast

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

See what the team at The Successful Bookkeeper has on right now → In the finale of his two-part conversation with Michael Palmer, Craig Taylor turns from personal security to the business side: how to train a team so that one rushed click doesn't become a ransomware headache. Craig is the founder and CEO of CyberHoot, and his message is encouraging. Most of what protects your firm is simple habits, taught in a way people want to repeat. Chapters [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: [email protected] 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 hostMichael PalmerMichael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.

See what the team at The Successful Bookkeeper has on right now → Bookkeepers sit right next to the money, and that makes them a favorite target for financially motivated hackers. In part one of this two-part conversation, Cyberhoot founder and CEO Craig Taylor explains how AI has changed the threats landing in your inbox, your texts and your phone calls. He also gives you a short list of habits that shut most of those attacks down. Craig started in cybersecurity 30 years ago with a psychology degree, and his focus is on behavior change rather than fear and shame. Chapters [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 hostMichael PalmerMichael 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 recommendationsThe Meteorologist Lesson: The Forecast Isn't the ProductDavid 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 QuestionMost 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 SignificanceOne 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 BelieveFor 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 SellingDavid 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 MentionedCerebral Selling website — free blogs, resources, and information on David's books and trainingSell the Way You Buy by David Priemer — available on Amazon, Audible, and KindleTo Sell Is Human by Daniel Pink — referenced during the discussion on sales perceptionShoe Dog by Phil Knight — referenced on leading with beliefDavid Priemer on LinkedIn — subscribe to his LinkedIn newsletterAbout the GuestDavid 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 hostMichael PalmerMichael 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'.