The Successful Bookkeeper Podcast

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: https://lauravanderkam.com
• Free time trackers (Google Sheets, Excel, and more): https://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'.

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
• https://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'.

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: https://meridian.pilot.com
• Pilot: https://pilot.com
• The Successful Bookkeeper: https://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'.

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: https://cyberhoot.com (book a demo; free 30-day trial)
• Free individual training: https://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: https://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'.

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
• [19:00] A listener's phishing story
• [22:00] Are QR codes safe to scan?
• [24:00] Password managers and passkeys
• [29:00] 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.

QR codes and a real-world phishing story

Michael shares a listener's story. After an office break-in, she tightened up her security, then got caught by a very good phishing email over a busy weekend and entered her password. 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." A manager only fills in credentials on the real site, so it protects you from phishing pages, and it saves you from changing 100 passwords after one breach. 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: https://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 https://www.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 (https://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 — https://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
• https://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.

Here’s a special gift for YOU. Visit https://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
• https://www.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: https://taxweave.ai
• Sam Leon on LinkedIn: search Samuel Leon CPA
• Claude (Anthropic): https://claude.ai
• PureBookkeeping: https://purebookkeeping.com
• Pluto (sponsor): https://pluto.com/tsb

About the Guest

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

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

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

Chapters

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

Sitting Is the New Smoking

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

Movement Snacks and the Hourly Reset

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

Tracking Your Metabolic Health

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

Hidden Energy Thieves

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

Fueling Your Brain Differently

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

Links Mentioned

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

About the Guest

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

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

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

Chapters

• [00:00] Opening quote on client value
• [01:18] Welcome and guest introduction
• [03:30] The provocative LinkedIn article
• [06:30] Defining what bookkeeping really is
• [10:00] Three times bookkeeping 'died'
• [15:00] AI as shepherd, not replacement
• [18:30] Who thrived through each shift
• [23:00] Evaluating tech without chasing shiny objects
• [27:30] Rising professionalism and community
• [31:30] Biggest opportunity the profession must not miss

Three "Deaths" That Were Actually Rebirths

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

The Core Job Has Never Changed

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

Humanity Is the Competitive Advantage

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

Thinking Clearly About AI Tools

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

A Rising Tide for the Whole Profession

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

Links Mentioned

• Lara Manton on LinkedIn — connect with Lara directly
• ACE-XL Ltd — Lara's finance process consultancy for larger businesses
• LJM Bookkeeping — Lara's UK bookkeeping practice
• https://purebookkeeping.com/ — episode sponsor, proven system for growing your bookkeeping business
• https://thesuccessfulbookkeeper.com/ — free business-building resources

About the Guest

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

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

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

Chapters

• [00:00] Opening: Fear and Opportunity
• [01:18] Alex Lee's Unlikely Path to AI
• [04:18] The Future Is Still You
• [08:00] Will AI Replace Bookkeepers?
• [12:00] Crawl, Walk, Run: Getting Started
• [16:30] AI Adoption Across the Profession
• [19:30] Data Privacy and Security Checklist
• [24:00] Vision for Accounting's Future
• [27:00] About Truewind

The Work That Has Always Mattered

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

The Spreadsheet Comparison Worth Remembering

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

A Crawl, Walk, Run Framework for Getting Started

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

Handling Data Privacy the Right Way

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

A Bigger Demand for Accountants Is Coming

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

Links Mentioned

• Truewind — Alex's AI-powered accounting platform
• The Successful Bookkeeper — show resources and guest information
• PureBookkeeping — episode sponsor, proven system to grow your bookkeeping business

About the Guest

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

About the host

Michael Palmer

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

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

Jon Sheldon has lived through more transitions than most people can imagine — Marine Corps infantry, corporate finance director, and now founder of Belleau Wood Coaching. This episode is a practical conversation about what it actually takes to lead yourself and your team well: getting clear on purpose, planning for what will go wrong, and building the kind of confidence that only comes from taking action. Whether you're just starting your bookkeeping practice or managing a growing team, there's something here for you.

Chapters

• [00:00] Purpose as the Common Thread
• [02:54] Jon's Background: Marines to Finance
• [08:00] Life's Purpose vs. Purpose Right Now
• [10:48] Accepting the Cost of Transition
• [15:00] Contingency Plans Beat Burning Boats
• [17:54] The Six-Step Decision Framework
• [22:00] Failure, Resilience, and Confidence
• [26:00] The Four-Pillar Performance Blueprint
• [31:00] Accountability and Radical Honesty
• [34:00] How to Connect with Jon

Purpose Is Not Just a Cliché

Jon believes purpose is the most overlooked driver in business — and in life. "Most people I run into don't ever take the time to, or have never taken the time to, really plan it out or think about what, how are they living a purposeful life?" It doesn't have to be a grand existential answer. Finding what fills you with purpose right now is enough to start leading better — yourself and the people around you.

Plan for What Will Go Wrong

One of the most practical ideas Jon brings from his Marine Corps days is what he calls "accepting the cost." Most people building a business focus on the vision and avoid thinking through what could go wrong — because they don't want to scare themselves out of it. Jon flips that: "Most battles are won with better contingency plans. That's how most missions are won — by thinking through the challenges and obstacles that are inevitably going to come." Knowing your worst-case scenarios in advance doesn't kill confidence. It creates it.

A Six-Step Decision Framework

Jon teaches a repeatable process he calls Clarity, Condition, Cost, Align, Act, Adapt. Get clear on what you're deciding. Do a gear check — do you have everything you need? Establish the cost of what could go wrong. Make sure your first action actually aligns with your goal. Act. Then adapt based on what you learn. "I've had the best plan and then the first action has nothing to do with pushing my business forward." The framework keeps that from happening.

Failure Is Part of the Deal

Jon is direct about this: failing is how you build the confidence to lead. "You might not hire the right person the first time. You might not make a great investment here or there. It's how you bounce back from that and get resilient that's going to really boost your confidence." If you're just getting started, expect some rough patches. If you have a clear purpose tied to where you're going, those rough patches are easier to push through — because the destination still matters.

The Four-Pillar Performance Blueprint

Jon works with every client through a four-pillar framework: Purpose (your why), Vision (a day-in-the-life picture of where you're headed, three years out), Ecosystem (who and what you're surrounding yourself with — including your tools and your workspace), and Motivators (what actually energizes you to take action). From there, his coaching is high accountability and action-driven: clients leave every session with a tracked action step, session notes, and metrics they've defined themselves. As Jon puts it, he's "tactfully tough and radically honest" — because most business owners don't have enough people in their corner telling them the truth.

Links mentioned

• Belleau Wood Coaching website: https://belleauwood.coach
• Instagram: @belleauwood_coaching
• LinkedIn: Jonathan Sheldon (search "Jonathan Sheldon Belleau Wood Coaching")
• Start With Why by Simon Sinek

About the guest

Jon Sheldon is the founder of Belleau Wood Coaching and a former Marine Corps infantryman who completed two back-to-back deployments to Iraq, leading 13 Marines through more than 200 combat missions. After leaving the military, he built a 14-year career in financial planning — running his own practice and then directing a regional team — before going full time into leadership coaching. He works with business owners and their teams on purpose, decision-making, and building the kind of resilient confidence that actually holds up when things get hard.

About the host

Michael Palmer

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

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

Nancy Benet, CPA, fractional CFO, and founder of Fix It Accounting, joins Michael Palmer for a conversation that is equal parts hard-won life lessons and practical bookkeeping wisdom. If you work with small business owners — or you are one — this episode will give you a sharper eye for the financial warning signs that show up long before a crisis does.

Chapters

• [00:00] Nancy's Origin Story Begins
• [02:28] Five Failed Businesses, $650K in Debt
• [06:08] Robbing Business Cash Flow
• [08:40] Opening Up and Taking Responsibility
• [12:28] Hiring Before You're Ready
• [15:30] Hidden Costs of a New Hire
• [18:00] Building the Firm From Scratch
• [22:00] Advisory Work and a $600K Win
• [24:30] Finding Clients Today
• [27:00] Using AI With Clients

From Rock Bottom to Running a Firm

Nancy's path to accounting was anything but straight. After leaving a CPA firm, failing at five businesses with her husband, and waking up at 45 with four children, no income, and $650,000 in debt, she had no obvious next step. What she did have was her CPA license and a willingness to start over. She landed a lease on a building the day before her intended business deal fell apart, and instead of walking away, she decided to fill that space herself. "I think that was probably the moment in my life when I stopped being a victim and I started taking responsibility," she says. That shift — from blame to ownership — gave her the confidence to hustle her way to a real client base.

The Hidden Cost of Robbing Business Cash

One of the most common mistakes Nancy sees — and lived herself — is pulling cash out of the business too early to fund a lifestyle the business hasn't earned yet. Big houses, expensive vehicles, family payroll that isn't justified by revenue: the money leaks out gradually and owners are often blindsided. Her advice is direct: keep three to six months of business expenses in the bank at all times, and live below your means in the early years. "That is what leads to problems later on," she says. "You just don't realize."

Fix the Systems Before You Hire

When clients come to Nancy wanting to add staff, her first question is whether they've made their existing operation as efficient as possible. Hiring looks like growth, but without the cash or the systems to support it, it just accelerates the leak. She walks clients through the full cost picture — not just salary, but holiday pay, absenteeism, the time spent fixing errors, and a training curve that can stretch a full year even for experienced hires. "A lot of newer businesses are not efficient at all," she says. "How can we address your systems first before you go into hiring, especially if you can't afford it?"

When Clients Won't Listen — and What to Do

Bookkeepers and accountants often see red flags that clients aren't ready to act on. Nancy is candid about the limits of what advisors can control: you can raise the concern, frame it carefully, and ask if they're open to a conversation, but you can't force a decision. What you can do is stay consistent and keep the door open. The clients who are willing to be guided, she finds, are also the ones most likely to grow — and to ask for the deeper advisory work that makes the relationship genuinely valuable.

Building Advisory Services and Using AI

Nancy started offering CFO-style work after a quick conversation with a client helped him decide to buy two pieces of equipment instead of paying off a loan — a choice that increased his net income by $600,000 the following year. That moment convinced her the advisory layer was worth building intentionally. On the technology front, her firm now uses a private AI instance to compare monthly financials year-over-year, then distills the output down to three bullet points for clients. "The client can't comprehend" a long analysis, she notes, so keeping it tight opens the door to a deeper conversation rather than closing it.

Links mentioned

• Fix It Accounting — Nancy Benet's CPA and fractional CFO firm
• CareerSource — free hiring and skills-testing resource for business owners (search your state's local CareerSource office)
• Pure Bookkeeping — episode sponsor
• The Successful Bookkeeper — show resources and guest information

About the guest

Nancy Benet is a CPA, fractional CFO, and the founder of Fix It Accounting, based in Florida. She built her firm from the ground up after overcoming significant personal and financial setbacks, starting with IRS problem resolution and growing into a full-service accounting, bookkeeping, and business advisory practice. Nancy works with small business owners to help them understand their numbers, make smarter financial decisions, and build businesses that actually support the life they want.

About the host

Michael Palmer

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

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

Customer experience expert Shep Hyken is back, and this conversation cuts straight to one of the most stubborn problems in the bookkeeping profession: the race to the bottom on price. Shep lays out why competing as a commodity is a choice — and a dangerous one — and gives bookkeepers a practical framework for building client relationships that make price almost irrelevant.

Chapters

• [00:00] Welcome and what has changed
• [02:35] AI, automation, and human jobs
• [06:30] The commodity trap explained
• [10:00] Competing on experience not price
• [13:00] Panera and moving humans to high-impact roles
• [16:00] Making routine interactions memorable
• [19:00] The six-step I'll Be Back framework
• [25:00] Journey mapping your client touchpoints
• [28:00] Consistency is what amazing looks like
• [30:00] Free resources from Shep Hyken

The Commodity Trap Is a Choice You Make

When a client sees you as a commodity, they're looking at your price, not the value of the experience you deliver. Shep argues that most bookkeepers already have the expertise to serve virtually any client well — so expertise alone no longer differentiates you. "Somebody that views you as a commodity is looking at your price, not just the experience that you have to offer." The solution isn't to slash rates; it's to make the relationship so strong that price becomes a secondary consideration. Competitive pricing and lowest pricing are not the same thing.

AI Amplifies Who You Already Are

Shep is clear that AI and automation aren't going away, but the firms quietly losing ground are the ones that have over-automated and stripped out the human element. He describes his own CPA firm eliminating his year-end review meeting in favor of a digital questionnaire — and how that single change made him start shopping around. "By going automated and not having that meeting, they just threw themselves into a commodity." The better move is to use automation to absorb the repetitive, low-touch tasks so you have more capacity for meaningful client conversations — not fewer.

The Six Questions That Build an "I'll Be Back" Experience

Shep walks through his six-step framework for understanding why clients choose you, why they might choose a competitor instead, and how to borrow ideas from outside your industry to raise your own standard. The exercise ends by asking: after everything you've learned, does your answer to "why me?" change? He also points to Amazon's order-confirmation model as an example bookkeepers can adapt — proactive, personal communication that keeps clients informed and feeling looked after.

Journey Mapping: Find the Pain Before Your Client Does

One of the most practical ideas in this episode is journey mapping every touchpoint a client has with your firm — from how the phone is answered to how the monthly invoice lands. Shep uses the example of restaurateur Will Guidara, who turned paying the bill at a high-end restaurant into a moment guests couldn't wait to tell their friends about. The same thinking applies to bookkeeping: "Find where those memorable opportunities are." There are moments in every client relationship — onboarding, monthly reporting, the annual review — that feel routine to you but could be genuinely memorable for them.

Consistency Is What "Amazing" Actually Looks Like

Shep closes with a reframe that is easy to miss: you don't need to be dramatically better than the competition. You need to be consistently and predictably better than average. "When that word always creeps in there — they always get back to me quickly, they always have the answers — you are operating above average." Trust is built through repetition, not grand gestures. Clients who can rely on you without having to think about it are clients who never seriously consider leaving.

Links Mentioned

• Hyken.com — Free annual customer experience research report and the Customer Confidence Score PDF (no email required)
• "Unreasonable Hospitality" by Will Guidara — Referenced for journey mapping and memorable experience design
• Pure Bookkeeping — Episode sponsor: https://purebookkeeping.com
• The Successful Bookkeeper — Show home and episode resources: https://thesuccessfulbookkeeper.com

About the Guest

Shep Hyken is the Chief Amazement Officer at Shepard Presentations and a hall-of-fame keynote speaker and New York Times bestselling author specializing in customer service and experience. He has advised organizations across industries on building loyalty, reducing churn, and creating cultures where clients feel genuinely cared for. Shep is a returning guest on The Successful Bookkeeper and brings research-backed, immediately actionable thinking every time he joins the show.

About the host

Michael Palmer

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

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

This is the second and final part of Michael Palmer's conversation with Andrew Seguin, founder of Seguin Financial. If you want a candid look at how a bookkeeping firm doubles revenue without a big advertising budget, this episode delivers. Andrew walks through the real levers he pulls: a four-day workweek that keeps his team loyal, a disciplined approach to scope creep, and a referral engine built entirely on great service.

Chapters

• [00:00] Introduction and Episode Recap
• [01:18] Four-Day Workweek Announcement
• [03:30] Andrew's Fridays: A Work in Progress
• [05:30] Scope Creep: How to Catch and Address It
• [09:30] Time Tracking as a Profitability Tool
• [12:00] How the Firm Doubled Revenue
• [15:00] Partnerships and Referral Strategy
• [18:00] Service as the Real Differentiator
• [21:30] Going Virtual Across Ontario
• [24:30] Final Advice: Start With Something

The Four-Day Workweek in Practice

Andrew made the switch to a Monday–Thursday, 36-hour week — with no pay cut for his team. "Working one hour extra per day doesn't feel as a big burden, but you get a whole day off every week, all year long," he explains. The response from clients has been overwhelmingly positive, and the retention impact has been real. For Andrew himself, it has gradually freed up his Fridays too — without the guilt of stepping away while his team is still at their desks.

Catching Scope Creep Before It Costs You

Andrew's approach to scope creep starts with the team: coach them to flag anything that feels different from the usual work, then back it up with time tracking so the numbers tell the story. Rather than hitting a client with a hard "that's out of scope," his firm offers two paths — "we can show you how to do it yourself, or we can have a conversation about a monthly increase to accommodate this." That framing keeps the conversation collaborative, not combative, and gets results either way.

Partnerships and Referrals as a Growth Engine

Seguin Financial grew from around a million dollars to double that in roughly 2.5 years — without meaningful advertising spend. The fuel? Strategic partnerships with fractional CFOs, outreach to franchise head offices, and a deliberate focus on asking the firm's best clients for referrals. "Our easiest client to take on is a referral," Andrew says, "because they've done probably so much work behind the scenes that at that point it's almost inevitable that they're going to become a client." Referrals arrive pre-sold — and they rarely price-shop.

Service Is What Clients Can Actually See

Andrew draws a clear line between quality of work and quality of service — and argues that for most clients, only one of those is visible. "Business owners are probably not going to always look at our reports. They might not really care a lot about the quality of the work. But the service they can see." Being responsive — not available at 8 PM, but back within 24 hours with an action plan — has moved Seguin Financial into a different tier in the eyes of their clients and made referrals far more frequent.

Start With Something, Then Let the Data Lead

Andrew's parting advice is straightforward: start tracking, even if it's just two spreadsheets. "Without time tracking, you're blind. You're honestly blind to which clients are doing very well for you and doing pretty poorly for you." He reviews his firm's analytics every month, makes a video for the team, calls out wins, and flags what to watch. That monthly discipline is what keeps the firm's profitability from quietly eroding — and what surfaces the clients worth doubling down on.

Links Mentioned

• The Successful Bookkeeper
• PureBookkeeping
• Seguin Financial — find Andrew on LinkedIn

About the Guest

Andrew Seguin is the founder of Seguin Financial, a virtual bookkeeping firm based in Cornwall, Ontario, Canada. With over eight years in the business, Andrew has grown his firm to serve clients across Ontario, with a focus on e-commerce and owner-operated businesses. He is known in the bookkeeping community for his data-driven approach to profitability and his commitment to building a firm culture that keeps great people around for the long haul.

About the host

Michael Palmer

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

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

Andrew Seguin was already running a strong bookkeeping firm when he last appeared on this podcast — at $1 million in revenue with a team of eight. Two and a half years later, he's back with a $2 million firm and a team of fifteen. In Part 1 of this two-part conversation, Andrew walks through the real work behind that growth: the systems he built, the delegation habits he had to form, and the profitability metrics that changed how he runs everything.

Chapters

• [00:00] Opening quote on delegation
• [00:42] Introducing Andrew Seguin
• [02:30] From $1M to $2M: the story
• [05:30] Getting out of the weeds
• [09:00] Building training systems that scale
• [13:00] Managing change without overwhelming the team
• [17:00] Introducing the effective hourly rate
• [23:00] Building the profitability dashboard
• [28:00] Time tracking: getting team buy-in
• [34:00] Pricing strategy and the 3-month clause

Getting Out of the Weeds

Even after hitting $1 million, Andrew was still deep in the day-to-day — doing bookkeeping, managing clients directly, and holding too much tax knowledge himself. The path to $2 million required him to deliberately reduce his own workload. "I was probably still doing a lot of day-to-day work," he says. "I knew I had some goals for '24 and '25, which was to reduce my own workload." That meant hiring a dedicated payroll team, bringing on a tax specialist, and doubling down on the pod structure — senior and junior team members working together as a unit.

Delegation Starts With Systems, Not Just Trust

One of Andrew's clearest lessons: delegation without a proper training system is just dumping work on people. He invested heavily in building a training package so that new hires could learn the firm's tools, standards, and workflows without having to figure things out from scratch. "You spend a little bit of time upfront — it's always hard because you have to find time to do it. But once you get over that hump, that's where things really start cascading into a really strong effect." He also cautions against piling on too much change in a single year, aiming instead for one meaningful improvement goal per year so the team isn't overwhelmed.

The Effective Hourly Rate: A Metric That Changed Everything

The single biggest profitability driver Andrew introduced was tracking each client's effective hourly rate (EHR) — revenue divided by hours worked on that file. His firm uses ClickUp for time tracking and QuickBooks Online for revenue data, feeding into a custom-built dashboard that shows the team exactly where they stand, client by client. "We essentially cut about 10% of our clients and then priced up about 40% of our clients to a rate that we wanted internally." The target range is $125–$150 per hour, minimum. Before this system, the firm's average was around $106–$108 per hour. After 18 months of using the data, it's closer to $250.

Transparent Data, Aligned Teams

Andrew doesn't hide this metric from his staff. The management team sees it. The bookkeepers who work on those files are aware of it. When a client's EHR falls short, the conversation isn't about poor performance — it's about scope creep, underestimated complexity, or pricing that needs revisiting. He also ties compensation growth directly to hitting those rates, so the team has a real reason to track their time accurately. "I'm very transparent — you guys wouldn't have these increases the way you have been getting for the last 3 years if we didn't have this data."

Pricing, Minimums, and the 3-Month Revisit Clause

Andrew's pricing approach is a hybrid of fixed and value-based: estimate the hours, multiply by the target EHR, then add complexity factors like multi-currency, e-commerce, or payroll. The firm's minimum for monthly engagements is $1,000, with an average around $1,600. Critically, every new engagement includes a clause allowing the firm to revisit pricing after three months — when actual time and complexity data is in hand. "We've had to do that a few times because there is no perfect system. A questionnaire and a quick conversation isn't going to tell you enough about the complexities and the volume of the file."

Links Mentioned

• PureBookkeeping — episode sponsor
• The Successful Bookkeeper — resources and episode archive
• ClickUp — project and time-tracking tool used by Seguin Financial

About the Guest

Andrew Seguin is the founder of Seguin Financial, a virtual bookkeeping firm based in Canada with a team of fifteen full-time staff. Over eight and a half years, Andrew grew his firm from a solo side practice to a $2 million business, built around strong systems, transparent team culture, and data-driven client management. He is a frequent speaker and educator in the bookkeeping community.

About the host

Michael Palmer

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

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

Amanda McKinney is back, and this conversation picks up right where the field is most uncomfortable: the place where your own capability quietly becomes the ceiling on your growth. If you've ever thought "it's faster if I just do it myself," this episode was made for you. Amanda brings her accountability coaching lens to the real-world pressures bookkeepers face — the revolving door of client work, the resistance to delegation, and the habits that quietly drain capacity before burnout ever arrives.

Chapters

• [00:00] The 3-Times System Rule
• [01:18] Welcome and Guest Introduction
• [03:30] Amanda's Journey Since 2023
• [08:30] Working With Teams Long-Term
• [13:00] When Capability Becomes an Obstacle
• [17:00] Warning Signs of Unsustainable Pace
• [21:00] The Case for Hobbies
• [25:00] Building Systems to Delegate
• [29:00] SOPs in Practice: Quarterly Taxes
• [32:30] Amanda's Podcast Pause

The Highly Capable Trap

Being good at your work is a genuine asset — right up until it isn't. Amanda explains that capability creates capacity, and capacity gets filled. "The problem with being capable is that it opens up more capacity. And when you have more capacity, you get more work. Either it's given to you or you give it to yourself." For bookkeepers, where the work never truly stops, this cycle can accelerate fast. Recognizing the pattern is the first step out of it.

Warning Signs Worth Watching

Amanda walks through the early signals that something needs to change — before burnout forces the issue. Physical heaviness when someone asks how you're doing, or the moment you realize your only answer to "what do you do for fun?" is your work. She shared that in 2024, that was her own reality. "I realized, oh my gosh, I have no hobbies. I don't have anything that I do just for fun." Intentionally adding even 15 minutes of something non-work-related a week can start shifting that.

The 3-Times Rule for Systems

This is the practical core of the episode. Amanda's rule of thumb: if you do something more than 3 times, it needs a system. She uses invoicing as a quick gut-check — if you can't describe your process fast, you're spending unnecessary brainpower every single time. The fix is straightforward: the next time you do that task, record yourself walking through it using a screen recorder like Loom or Neato (free). That recording becomes your SOP, and that SOP becomes your delegation tool. She applied this to her own quarterly tax payments: "I did it in like 15 minutes. Whereas that would have taken me an hour or two if I didn't have those steps written out."

Delegation Without the Dread

Most bookkeepers resist handing work off because training someone else feels slower than doing it themselves. Amanda reframes this: a documented system removes most of that training burden. The SOP does the heavy lifting, and the person you're delegating to — whether human or software — gets a clear path to follow your standards. As Michael put it during the conversation, "SOPs are the pathway to profitability."

Sustainable Growth Requires a Pause

Amanda recently did something that surprised her own audience: she intentionally paused her podcast after eight straight years of weekly content. The flood of concerned emails she received made her realize how rarely people pause before something forces them to. The message for bookkeepers is the same — growth that lasts has to be built on something sustainable. Waiting for a crisis to rest isn't a strategy. "You don't have to be burnt out before you make a decision to change something."

Links Mentioned

• Loom — screen and voice recording tool for creating SOPs
• Neeto — free alternative screen recording tool (used by The Successful Bookkeeper team)
• https://www.purebookkeeping.com — episode sponsor; system to grow your bookkeeping business
• https://www.thesuccessfulbookkeeper.com — show resources and guest info
• Accountable podcast by Amanda McKinney (300+ episodes available; currently on intentional pause)

About the Guest

Amanda McKinney is an accountability coach, speaker, and the host of the Accountable podcast (formerly The Unapologetic Entrepreneur). She works primarily with driven entrepreneurs and leadership teams to help them follow through on goals that keep getting pushed to the back burner — without burning out in the process. She has been coaching since 2017 and now leads engagements ranging from 90-day individual programs to 9–12 month team partnerships. You can find her through her podcast archive of 300+ episodes or by reaching out directly through her website.

About the host

Michael Palmer

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

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

Your clients' financials tell one story. What your clients think about their business tells another. In this episode, fractional CFO, course creator, and speaker Debra Angilletta returns to show how closing that gap — through simple, curiosity-driven conversations — is the most direct path to selling advisory services. No complicated sales process required.

Chapters

• [00:00] Opening Quote and Intro
• [01:35] Meet Debra Angilletta
• [03:30] Why Bookkeepers Struggle to Sell Advisory
• [06:10] The "Curious" Question Technique
• [09:20] Staying Human in a Digital World
• [11:50] Finding Your First Five Clients
• [14:30] The Advisory Transformation
• [17:30] What 100 Business Owners Said
• [20:30] About the Book: Hidden Profits
• [22:40] Rapid Fire: Steps to Take Now

The Missing Half of the Story

Numbers give you the facts; your client's perspective gives you the context. Debra frames advisory as the natural result of putting those two pieces together: "When you put those two pieces of information together, that's where the magic happens, and that's where you can fill the gap." The good news is you already have one half. You just need to ask for the other.

One Word That Changes Everything

If you're not sure how to start a probing question without sounding nosy or accusatory, Debra has a single practical fix: lead with "curious." Saying "Curious — I noticed this in your books, can you tell me more?" removes any sense of blame, gives your client permission to explore rather than defend, and opens the conversation rather than closing it down. It's a small shift with a big effect on how clients respond.

Finding Your First Five

You don't need to overhaul your entire practice to get started. Debra's advice is to scan your client list, pick five people who seem most open to a deeper conversation, and book a 30-minute call — framed simply as "I saw some interesting things in your books that might be of value." That's it. The goal isn't to pitch advisory on the spot; it's to practice having the conversation. "There's nothing complicated here," Debra says. "I don't want to make it complicated for your audience at all."

Business Owners Are Waiting for You to Ask

Debra interviewed 100 small business owners while writing her book Hidden Profits, and the finding stopped her in her tracks. When she asked what they wished their bookkeeper did that they weren't doing, the answer was overwhelming: more strategic advisory. "I wish they would give me information that I can use to drive my business forward." Most business owners operate in isolation, with no one to think out loud with — and your existing financial relationship puts you closer to that trusted-advisor seat than you might realize.

The Transformation on the Other Side

Bookkeepers who start having these conversations consistently go through a noticeable shift. Debra sees it regularly: once they experience what advisory conversations feel like, they want more of them. More importantly, the relationship with the client changes. "It actually uplevels you to partnership level... they're going to see you as that trusted advisor." The compliance work stays valuable — but it's no longer the ceiling on what the relationship can be.

Links Mentioned

• Hidden Profits: Stop Chasing Cash, Predictable Profit in 90 Days by Debra Angilletta — http://findmyhiddenprofits.com (free download of first 3 chapters) or search "Hidden Profits" on Amazon
• MasterMySales.com — Debra's sales training for financial professionals
• http://purebookkeeping.com — episode sponsor
• http://thesuccessfulbookkeeper.com — show resources and guest links

About the Guest

Debra Angilletta is a fractional CFO, course creator, and speaker at MasterMySales.com who specializes in helping bookkeepers, accountants, and financial professionals sell and deliver advisory services with confidence. She works primarily with small business owners in the $500K–$3M revenue range and is the author of Hidden Profits: Stop Chasing Cash, Predictable Profit in 90 Days. Debra is a returning speaker at The Successful Bookkeeper Summit and a consistent audience favourite.

About the host

Michael Palmer

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

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

Dr. Sabrina Starling has spent over 20 years helping small business owners build profitable, sustainable companies without burning themselves out. In this episode, she brings her business psychology background directly to bookkeepers — walking through her $10,000-an-hour framework, the mindset shift that changed everything for her, and the practical steps you can take right now to stop trading hours for dollars and start building a business that works without you.

Chapters

• [00:00] Opening and guest introduction
• [01:35] Burnout and starting a business
• [04:40] The E-Myth epiphany
• [08:10] The $10,000-an-hour framework
• [12:40] First hire and finding A-players
• [17:00] Time audits and glass ceilings
• [19:10] What has and hasn't changed in 20 years
• [22:40] AI and the human advantage
• [25:30] Serving your top clients and micro-innovation
• [28:50] The free download and closing thoughts

From Burnout to 25 Hours a Week

Sabrina started her business fresh out of a gruelling career as a psychologist in community mental health — working 40- to 50-hour weeks, taking on-call shifts, and running on empty. When she launched her coaching practice and started a family at the same time, she made what she calls a "very naive declaration": she would only work 25 hours a week. What felt like an impossible constraint turned out to be one of the best decisions she ever made. "Limits force innovation and creativity," she explains. That boundary forced her to be ruthlessly focused on only the work that moved the business forward.

The $10,000-an-Hour Framework

The turning point came when Sabrina started categorising every task in her business by its dollar-per-hour value — $10, $100, $1,000, or $10,000. She printed the chart and put it behind her monitor so she'd see it constantly. "Inevitably, I would be nose down working on something for a client, and then I would look up and say, oh my gosh, I've just spent 4 hours in $10 and $100 an hour activity." Blocking her highest-value work on the calendar first — before checking email, before firefighting — is what made the difference. She's made the chart available as a free download at tapthepotential.com/10k, along with two podcast episodes walking through how to use it for yourself and with your team.

Hiring A-Players Into the Right Seats

Sabrina's first hire was a virtual assistant — and the thinking she put into that hire became the seed of her How to Hire the Best book series. Rather than hiring fast out of desperation, she asked: what strengths does this role actually require to deliver results day in and day out? Her original VA, hired for her people skills and attention to detail, is still with the company 20 years later. "One A-player in the right seat working from their strengths will be 900% to 1,200% more productive than a warm body team member." For bookkeepers, payroll is already the biggest profit leak — and it's usually not optimised with A-players.

AI, Adaptability, and the Human Advantage

AI is reshaping bookkeeping, and Sabrina doesn't sidestep that. But her take is direct: when you offload $10-an-hour busywork to AI, you free yourself to do the work that actually can't be automated — deeply understanding your best clients, spotting problems they can't see in their own numbers, and delivering insight that goes far beyond the books. "When we convey to our team members that we want them doing $10,000 an hour work and we're going to show them how, they get so excited and they are relieved because they know they have job security at that point." The bookkeepers who will thrive are the ones having real conversations with their top clients and continuously innovating around their needs.

Working From Your Sweet Spot

Sabrina encourages bookkeepers to identify the 20% of clients driving 80% of revenue — and then narrow that further to the ones who are also a genuine joy to work with. Those are the relationships worth doubling down on. Use your natural detail orientation to tune in to what those clients are worried about, what's keeping them up at night, and where you can remove friction for them. She calls the result "micro-innovation" — small, consistent improvements that compound over time and make you genuinely irreplaceable. "Small steps forward taken in a consistent direction lead to big change over time."

Links Mentioned

• Free $10,000-an-hour activity chart + bonus podcast episodes: https://tapthepotential.com/10k
• The E-Myth by Michael Gerber
• How to Hire the Best book series by Dr. Sabrina Starling
• Profit by Design Podcast (Tap the Potential)
• https://thesuccessfulbookkeeper.com

About the Guest

Dr. Sabrina Starling is a business psychologist, speaker, and author, and the founder of Tap the Potential LLC. She helps entrepreneurs build profitable, sustainably run companies by hiring A-players, building strong systems, and designing businesses that support their lives — not the other way around. Her entire team works 25 hours a week, and she has personally worked down to about 10. She is the author of the How to Hire the Best series and hosts the Profit by Design podcast.

About the host

Michael Palmer

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