The Successful Bookkeeper Podcast

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 Here’s a special gift for YOU. Visit Plooto.com/TSB and try it for FREE for two months! That’s a FREE 30-day trial, plus an extra free month for Successful Bookkeeper podcast listeners! Don’t miss out, sign up TODAY! From Curiosity to Real Workflows Sam has been watching technology waves roll through the accounting profession for years — cryptocurrency, machine learning, practice management software. When AI chatbots arrived, he started testing them immediately, but it was a specific feature of Claude that changed how he worked: the ability to connect the tool directly to files on his computer. "That's how I got started with a lot of the more time-saving workflows that I was doing," he explains. The shift from chatting with AI to feeding it real documents opened the door to genuine time savings rather than novelty. The Tasks Best Suited for Automation Sam is direct about where AI earns its keep: document summarization, transaction categorization, and building QuickBooks rules. He recently spoke with a bookkeeper who used AI to generate an extensive list of transaction rules that could be imported straight into QuickBooks — a task that would have taken hours to build manually. His broader advice is to start with tasks that are data-heavy and repeatable, then layer AI on top of the tools you already use rather than replacing them outright. Handling Sensitive Data the Right Way This is where Sam slows down and gets careful, and so should you. For tax professionals in the US, IRS Code Section 7216 governs what client information can be shared with third-party systems — and most AI platforms have not yet been through the kind of SOC 2 certification process that established tax software has. Sam's personal rule: never upload anything containing Social Security numbers, EINs, or last names. For bookkeeping work, he sees a slightly lower barrier since transaction lists are often less personally identifying, but the principle holds. "Being more cautious than not — if you're unsure about it, probably take another step to make sure that information really doesn't have any personal identifying information on it." Upgrading to a Teams or Business plan on these platforms also adds a layer of data protection over personal accounts. Building TaxWeave: From Workaround to Platform The manual redaction problem — using Adobe to black out client details before running documents through AI — was slow and error-prone. That frustration pushed Sam to start building TaxWeave, a platform designed to handle the redaction automatically inside a secure environment, then run AI workflows on the cleaned documents. He built the initial prototype using Claude Code, which lets you describe what you want in plain language and generates the underlying code. "The barrier where you had to understand how to do that — it's removing that," he says. TaxWeave currently focuses on tax practice project management and client organization, with AI workflow integration being the layer built on top. Keeping Up as the Models Keep Changing AI models update constantly, and Sam's advice is to treat your workflows the same way you treat your engagement letters — review them periodically and adjust. He recommends using the Projects feature in Claude to maintain context across sessions, and revisiting your saved instructions whenever a new model version drops. You can even ask the AI itself what needs updating. For quality control, Sam still does his own research to verify AI-generated answers and checks outputs manually, paying attention over time to where the tool is weakest. "You can start to see what it's weaker on — what kind of things does it always miss — and what you can start trusting it with." Links Mentioned TaxWeave: taxweave.ai Sam Leon on LinkedIn: search Samuel Leon CPA Claude (Anthropic): claude.ai PureBookkeeping: purebookkeeping.com Pluto (sponsor): pluto.com/tsb About the Guest Sam Leon is a CPA with 14 years of experience in tax accounting, specializing in corporate tax, startup tax issues, R&D credits, and individual returns. After building his solo firm, The Millennial CPA, he was recognized in the 2026 Accounting Today Best Firms for Technology Awards. He is currently developing TaxWeave, an AI-powered platform built specifically for tax practices, and is active in conversations across the profession about safe, practical uses of AI in accounting.

See what the team at The Successful Bookkeeper has on right now → Teresa Gregory has spent her career helping leaders find the hidden patterns that quietly shape every decision they make. In this conversation with host Michael Palmer, she turns that lens directly on bookkeeping professionals — the people who sit in a unique seat of trust with their clients every single day. Whether you manage a team, serve a full client roster, or are building your firm on your own, the mindset habits Teresa shares here apply immediately. Chapters [00:00] Introduction and Teresa's Background [03:13] Hidden Bias and First Impressions [07:00] Bias as a Biological Response [11:00] Working With Difficult Clients [14:30] The PAUSE Method Explained [19:00] Active Listening vs. Reloading [23:00] Strategic Client Check-Ins [27:00] Why Every Bookkeeper Needs a Coach [31:30] Positioning Yourself as an ROI Expert [35:30] Teresa's Resources and Wrap-Up Hidden Bias Is Running in the Background Every interaction you walk into carries invisible baggage. Teresa calls it the fight-or-flight response — a biological pattern your brain uses to assess safety and make quick judgments. The problem isn't that it exists; the problem is when you let a past experience cloud what's happening right now. "I'm reinforcing every time I have this engagement with them without identifying it and without saying, 'hey, this is what's going on,'" she explains. The first step is simply naming the bias before you walk into a meeting, a call, or a difficult conversation. The PAUSE Method for Breaking the Pattern Teresa teaches a five-step framework — Pause, Awareness, Unwind, Strategic, Effectiveness — that gives leaders a repeatable way to interrupt bias before it takes over. Pause and name what you're carrying. Build awareness of when it tends to show up. Unwind the reinforced pattern. Be strategic about what you'll do differently. Then evaluate honestly: did it work? "You have to identify it and say, 'this is what's causing me to do this,' and then look at how do I overcome it?" The method works whether you're prepping for a tense client review or walking into a room full of people you're slightly in awe of. Active Listening vs. Reloading Most people think they're listening. Teresa says they're reloading — nodding, making eye contact, and waiting for their turn to talk. Active listening looks different: you take in what the client actually said, reframe it back in your own words, and confirm you got it right. "What I heard you saying is…" followed by "Did I get that right?" This one shift builds more trust than almost anything else you can do. For bookkeepers — who already have deep, consistent access to business owners — it's a fast path to becoming a true strategic partner rather than a transactional vendor. Know What Your Client Actually Cares About Teresa is direct: you should have a running list of each client's core values and priorities. "If I cannot say to Michael, your number one important thing is ROI or bottom line or taxes, I need to be able to identify that. You should have a running list of what are the things that are important to that client so you can speak to those — and then any solution that you're proposing or any conversation you're having ties right back to it." Schedule intentional check-ins — monthly if possible, quarterly at minimum — to ask what has changed. Businesses change. Lives change. If you're not asking, you're missing it. Reposition Yourself as an ROI Expert One of the most practical moments in this episode is Teresa's challenge to bookkeepers to rethink how they introduce themselves. "If you were to tell me, 'I offer business owners a strategic advantage because I help them understand ROI' — now I'm like, whoa, I need that." Her own sister, a bookkeeper, spent six months practicing a new way of describing her work at local chamber events. The result: new clients in industries she'd never considered. You track every dollar that moves through a business. That is, by definition, the work of an ROI expert. Lead with that. Links mentioned Squared Success website: squaredsuccess.com Teresa Gregory on LinkedIn: search "Teresa L. Gregory" PureBookkeeping: purebookkeeping.com The Successful Bookkeeper: thesuccessfulbookkeeper.com About the guest Teresa Gregory is the founder of Squared Success, a leadership strategy and coaching firm. She began her career in training and development inside corporate organizations — including supporting the finance team at Microsoft — before transitioning into executive coaching for business owners. Her work focuses on helping leaders uncover hidden mindset barriers, break bias patterns, and build the intentional habits that drive real results. Teresa is also a speaker and, notably, coaches her own bookkeeper sister to help her grow her firm. About the hostMichael PalmerMichael 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 → Melissa Broughton, founder of Busy Bee Advisors in Sacramento, has built a bookkeeping firm that grows not just through referrals and marketing, but through strategic acquisition of other bookkeeping practices. In this episode, she pulls back the curtain on her complete acquisition process — from finding firms before they shut their doors, to vetting the financials, to integrating clients without losing them. If you've ever wondered whether buying a book of business could be part of your growth plan, Melissa's experience — including the deals that went sideways — is exactly what you need to hear. Chapters [00:00] Cold open teaser [01:15] Melissa's growth journey since last episode [05:30] Launching an online bookkeeping course [09:00] How the acquisition strategy began [12:30] The 70% rule and the water test [17:00] Vetting financials and avoiding pitfalls [21:00] What makes a firm attractive to buyers [25:30] Client integration and transition lessons [30:00] Reading the seller's personality [33:30] Capacity, formulas, and skipping brokers How Melissa Got Into Acquisitions It started with a pattern Melissa kept hearing from tax professionals: a bookkeeper with a thriving practice would simply close up shop, send clients a farewell letter, and leave them scrambling. "There were bookkeepers who had successful, thriving practices and they just decided to retire — they just closed their doors." That gap between a bookkeeper ready to walk away and clients who still need service looked like an opportunity. The goal became getting in front of those owners before they pulled the plug. The 70% Rule and Other Benchmarks Melissa's core filter is straightforward: would the acquisition still be profitable if you only kept 70% of the clients? "We look at, is the business still profitable if you only retain 70% of their business? That's our benchmark." She calls it the "water test," and a surprising number of potential deals don't pass it. She also looks at minimum client roster size, client interaction levels, software alignment (her firm runs exclusively on QuickBooks Online), and whether all clients are under a signed contract. A book of business built on handshakes and mixed software platforms is a much riskier buy than it appears on paper. Vetting the Financials — Don't Take It as Gospel Because bookkeepers are numbers people, Melissa says they're actually well-positioned to do the kind of financial scrutiny most buyers skip. "Ask for proof of those deposits. Make sure that the income lines up." She requests bank statements alongside tax returns, digs into payroll breakdowns, and checks lease agreements — because taking on a seller's remaining lease obligations can quietly sink a deal. She also warns against letting a seller's likability cloud the numbers: "Nice has nothing to do with it." Integration: What Makes or Breaks the Transition The smoothest acquisition Melissa ever completed involved an owner who was fully ready to walk away and sent a clean, brief handover note to clients. The hardest ones involved sellers who couldn't really let go. "We generally will not have the owners stay on — I can only think of two situations where we've had the owners stay on, and I will say I regretted it both of those times." For every acquisition, she brings on extra team support and deploys what she calls a "client whisperer" — a trusted admin who calls each new client, makes the introduction, and asks the question most people avoid: what did your previous bookkeeper do that drove you crazy? What Sellers Should Know Melissa also flips the conversation for bookkeepers thinking about eventually selling their practice. The three biggest value drivers in her eyes are: signed contracts with every client, a reasonable level of ongoing client communication (not too hands-off, not so personal that clients will leave when you do), and consistent use of mainstream software. She also recommends having payment on file rather than invoicing after the fact — both as a business practice and because it signals a well-run, collectible revenue stream to any buyer. Starting negotiations, Melissa uses a 1.25x multiplier on receivables as a baseline and works from there. Links Mentioned Busy Bee Advisors: busybeeadvisors.com Contact Melissa directly for her acquisition formula and checklist — email will be in the show notes The Successful Bookkeeper: thesuccessfulbookkeeper.com Pure Bookkeeping: purebookkeeping.com About Melissa Broughton Melissa Broughton is the founder and owner of Busy Bee Advisors, a fully remote bookkeeping firm headquartered in Sacramento, California, with team members spread across the United States. She has built and sold businesses across multiple industries and has applied those lessons to growing her bookkeeping practice through strategic acquisitions. In 2024, she launched an online course to help aspiring bookkeepers start their own businesses; by August 2025, more than 3,500 people had completed it. Melissa is a returning guest on The Successful Bookkeeper podcast. About the hostMichael PalmerMichael 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 → AI is moving fast, and the bookkeeping profession is squarely in its path — but not in the way most people fear. In this episode, Michael Palmer sits down with AI strategist and educator Benjamin Tasker to talk about what the shift actually looks like on the ground, which skills will separate bookkeepers who thrive from those who stall, and how to start building your own AI system without a data science degree. Chapters [00:00] Welcome and Ben's Background [03:15] From Data Science to AI Education [08:00] AI's Real Impact on Bookkeeping [12:00] Human Judgment as the Key Check [15:30] Skills That Separate Thriving Bookkeepers [21:00] Data, Systems, and AI Strategy [25:00] Opportunities to Move Up the Value Chain [29:00] First Steps for Integrating AI [32:00] Client Expectations and Transparency [35:00] Fear, Mindset, and Where to Find Ben AI Will Elevate Bookkeeping, Not Replace It Ben is direct about the headline fear: bookkeepers are not going away. "AI will help elevate what a bookkeeper does," he says. The repetitive work — transaction coding, receipt capture, anomaly detection, drafting reports — gets absorbed by AI, which frees up the bookkeeper to move from data entry to data judgment. Think less time in the books and more time coaching clients on their financial pain points. AICPA and Intuit both point in the same direction: the future of the role looks a lot more like analytics and advisory than data input. The Two Skill Lanes Every Bookkeeper Should Know Ben references the World Economic Forum's skills taxonomy, which divides skills into two tracks. AI skills — analytical thinking, systems thinking, coding — pay a premium today, but AI will eventually encroach on those. Human skills — communication, empathy, leadership — are undervalued right now but will command a premium as AI can only mimic, never genuinely replace, them. "AI can put on a facade of empathy and compassion, but it really can't have it because it's robotic." For bookkeepers, the practical focus areas are AI supervision (checking outputs rigorously), advisory thinking, digital and data fluency, and transparent client communication. The Human in the Loop Is Not Optional Ben's background in healthcare data — building algorithms to predict sepsis risk from bedside monitors — gives him a sharp view on why human validation matters. A small data error that goes unchecked can cascade into a much larger problem. "A mistake, especially for a small business owner, could cost tens of thousands of dollars." Bookkeepers already understand this: the work is either right or it isn't. That precision mindset is exactly what responsible AI use demands, and it is a genuine competitive advantage for practitioners who carry it into their AI workflows. Data Is the Oil — Build a System, Not Just a Stack of Tools One of Ben's clearest points: buying an AI tool is not an AI strategy. The framework he outlines is straightforward — start with your data (client records, call transcripts, templates, Google Sheets), run it through a system you build and control, apply AI to it, then validate and iterate. "Just because you buy an AI tool doesn't mean you have an AI strategy or even an AI business." He encourages bookkeepers to build their own processing systems rather than relying entirely on third-party integrations that can change without warning. Start small — something as simple as having AI draft follow-up emails from call transcripts is a low-risk, high-value first step. Practical First Steps and Client Communication For bookkeepers ready to start, Ben's advice is to pick a low-stakes problem, solve it, and let that build confidence. Use AI to profile prospective clients from call transcripts, automate follow-up reminders, or create a client-facing dashboard from existing data. On the client side, transparency is non-negotiable: communicate that you are using AI, explain how it benefits them, and teach them how to give better inputs so they get better outputs. "By providing inputs and encouraging your customers to use AI to show them the benefits of it, they're going to become less resistant over time." That kind of teaching deepens the client relationship well beyond what traditional bookkeeping alone can offer. Links Mentioned Ben Tasker AI: bentaskerai.com Ben Tasker on LinkedIn World Economic Forum Skills Taxonomy (AI skills and human skills tracks) The Successful Bookkeeper Pure Bookkeeping About the Guest Benjamin Tasker is an AI strategist, educator, and speaker with over 10 years of experience in data science and artificial intelligence. His background spans healthcare predictive analytics, higher education, and enterprise AI strategy. Today he helps entrepreneurs and large organizations build the skills and systems they need to navigate the AI revolution. You can find his prompting frameworks, podcast appearances, and upcoming events at bentaskerai.com. About the hostMichael PalmerMichael 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 → Anne Napolitano started her firm a decade ago as a solopreneur with an accounting degree, a background as a controller for Hermès of Paris, and a stint as a personal chef. Today she runs a 10-person firm with a specialty niche in food and beverage — and she has learned, often the hard way, how to charge what her work is actually worth. This episode is a practical, honest conversation about building advisory services into a bookkeeping firm, pricing with confidence, and communicating value so clients never have to wonder what you do for them. Chapters [00:00] Anne's Background and Firm Journey [05:03] Early Mistakes and Hard Lessons [09:07] Building Advisory Into the Practice [12:24] Tools, Confidence, and Clean Data [14:33] Selling Advisory to Skeptical Clients [18:20] Segmenting Clients for Higher-Tier Work [20:42] Packaging and Proposals That Work [23:34] Pricing Courage and Recovering from Undercharging [28:19] Communicating Value Before Clients Leave [30:29] Pivotal Moments and What She'd Do Differently From Bookkeeping to Advisory: It Takes Time to Grow Into It Anne didn't launch as a full advisory firm on day one — the advisory side evolved as her confidence and team grew. She credits closing the books fast (her target is the 10th–15th of each month) as the foundation that makes advisory possible. "The faster we can get the bookkeeping done, that allows us 2 weeks at the end of the month to meet with clients and to do the advisory type of work that we really enjoy." Without clean, timely data, there's nothing to advise on. Selling Advisory When Clients Don't Know They Need It Many clients assume advisory is bundled into their basic bookkeeping fee. Anne's approach is to start with bookkeeping, build trust, and then show — not tell — what advisory can do. She uses dashboards, charts, and graphs in prospect calls, sometimes pulling analysis directly from a prospect's QuickBooks file before they've even signed. "We have found that that has been a game changer." Visual tools lower the barrier for clients who tune out a P&L but respond immediately to a trend line. Segmenting Clients for Higher-Tier Services Not every client is ready for advisory, and Anne stopped pretending otherwise. She segments roughly the top 15–30% of her client base into higher-tier engagements based on revenue size, reporting complexity, or multi-entity structures — not just headcount. Clients who don't start there often grow into it. "Some of the other clients move themselves into advisory over time. Either they grow or become more complex, or we've shown them what we can do for them — and by then we have a relationship, so they trust us." The Pricing Trap: Being a Recovering Underpricer Anne is direct about the pricing mistakes she's still working through. She uses value pricing (no hourly billing), offers three-tier proposal packages, and spells out scope precisely to avoid scope creep and client assumptions. But the real obstacle is internal. "I'm a recovering underpricer. You need to be willing and able for them to walk away. Because if they're not going to pay your price, it's not a good client for you." She also anchors pricing against the cost of a full-time hire — converting monthly fees to an annual figure so clients can compare apples to apples. Communicating Value Before Clients Drift Away Losing clients not because of bad work, but because clients didn't understand what was being done for them, was one of Anne's hardest lessons. Her fix: overcommunicate. Her team now sends monthly summaries through their client portal covering what was done, errors caught, fraud signals flagged, and money saved. "We don't always communicate to a client, and we found that that was a big mistake." She describes it as an iceberg — clients see the surface, but the firm's job is to make the work below the waterline visible. --- Links Mentioned Anne Napolitano on LinkedIn Anne Napolitano on Instagram: search Anne Napolitano The Balance Sheet — Anne's monthly newsletter (contact her via social media to subscribe) The Successful Bookkeeper Summit — this year's theme: Owning Your Authority PureBookkeeping.com — episode sponsor Woodard conferences and education (mentioned as a resource for advisory skill-building) --- About the Guest Anne Napolitano is the founder of Anne Napolitano Consulting, a modern accounting and advisory firm she has grown over 10 years from a solo practice to a 10-person team. With over 30 years in accounting — including a role as U.S. controller for Hermès of Paris — Anne specializes in bookkeeping and CFO-level advisory services for food and beverage businesses, nonprofits, and general small business clients. She is based in the United States and is active on LinkedIn and Instagram.

"There were times I remember having to pull money out of our retirement savings to cover payroll. We weren't sleeping, we were stressed. We didn't know where to turn, and it was so stressful. It was not a good scenario." -Teresa Slack In this episode, Canadian bookkeeping expert and million-dollar firm builder Teresa Slack shares the hard truth about pricing and what it really costs when you get it wrong. She breaks down her journey from charging $18/hour and burning out to building a profitable, scalable firm using value pricing and better systems, along with the key mistakes to avoid and what actually drives growth. In this episode, you'll learn: The difference between fixed pricing & true value pricing How to raise your prices without losing your best clients Why identifying your ideal client changes everything To learn more about Teresa, click here. Connect with her on LinkedIn. Time Stamps 01:05 – Teresa's journey from struggling firm to success 04:00 – Early pricing mistakes & mindset challenges 07:01 – How poor pricing led to financial stress 09:42 – The turning point: systems & value pricing 17:36 – Where most bookkeepers go wrong with pricing 19:28 – How to raise prices the right way 21:42 – What happened after repricing clients 24:08 – The compounding effect of better pricing 28:10 – Finding your niche & ideal clients 36:09 – Why action builds confidence Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

" When you start speaking to yourself with more precise and definitive language, it changes how you show up for yourself. Think about how your clients and the people that you work with, it impacts how they see you." –Justin Atherton In this episode, former law enforcement detective, SWAT operator, and leadership coach, Justin Atherton breaks down a skill most bookkeepers overlook: precise communication. He explains how the words you use every day either build trust or quietly destroy it, and shares how vague language creates confusion, missed deadlines, and weak client relationships. If you've ever felt frustrated by clients not following through, this episode will change how you speak, write, and lead. In this episode, you'll learn: How "stop action verbs" sabotage your results How to replace "I'll try" with language that drives action How to communicate deadlines clearly & avoid confusion To learn more about Justin, click here. Connect with him on LinkedIn. Watch Justin's TEDx Talk: The Suspect Within. Buy his book, How To Get To The Damn Point at this link. Time Stamps 01:03 – Justin's background in law enforcement & leadership 05:06 – Why communication problems exist in every industry 06:25 – The danger of vague, abstract language 14:32 – The Wave Method explained 15:27 – Stop action verbs & how they weaken your message 19:10 – Awareness & catching your language in real time 30:06 – How to write clearer emails that get results 36:18 – Using accountability to change communication habits 41:30 – Justin's book & practical tools Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"This is how you look at success. It is only a narrative of people to people, to people. Why else wouldn't you wanna spend your time doing that more purposefully and intentionally?" -David Homan In the finale of our two-part series with community building strategist and author, David Homan, he will show you how to turn everyday interests into real connections and why the opportunities you're looking for are already closer than you think. You'll learn how to move past hesitation, stop overthinking networking, and start building relationships that lead to real trust, referrals, and long-term opportunities. In this episode, you'll learn: Why asking for help is less effective than offering it How to overcome intimidation & connect with anyone A simple habit that strengthens relationships & builds trust To learn more about David, click here. Connect with him on LinkedIn. Get a copy of Orchestrating Connection at this link. Time Stamps 01:00 – Turning everyday interests into connection 04:48 – Why gratitude calls create unexpected opportunities 07:42 – Overcoming intimidation & imposter thinking 12:09 – Shifting from "me" to "how can I help?" 17:17 – Reconnecting with people you've lost touch with 21:47 – How real opportunities are built through people 24:14 – Why small actions create bigger impact than you think Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"There's all that magic that seems to happen by those who are born with relationship privilege, but we can all build it. It just starts with how you can become more purposeful and intentional with what you want out of not just your life, but the people around you that form your purposeful community." -David Homan Community-building strategist and author of Orchestrating Connection, David Homan challenges the way you think about networking. He explains why traditional networking often feels forced and ineffective, and shows how shifting toward intentional, trust-based relationships can open doors you didn't think were possible. David shares how vulnerability, curiosity, and generosity create stronger connections, and why building a purposeful community matters more than collecting contacts. In this episode, you'll learn: Why most networking fails & what to do instead How to turn your existing network into a supportive community A simple way to create opportunities without asking for anything To learn more about David, click here. Connect with him on LinkedIn. Get a copy of Orchestrating Connection this link. Time Stamps 00:56 – Why traditional networking feels forced 02:08 – David's background & early exposure to relationships 09:34 – Network vs. purposeful community 11:40 – Using vulnerability to build trust 19:19 – Real connection vs. transactional conversations 23:29 – The five principles of meaningful relationships 29:16 – How to start building your community today Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"High performers liked to be with high performers. So if you start to train yourself as a manager, as a boss, as a business owner, as an entrepreneur, in holding people accountable, you will notice who doesn't mind that, who kind of thrives around that, and those kind of people attract more people like that." –Gina Cotner In this episode, founder and CEO of Athena Executive Services, Gina Cotner shares a practical framework for holding your team accountable without creating tension or fear. She explains why delegation alone is not enough, how accountability builds stronger leaders inside your firm, and how small shifts in communication can dramatically improve follow-through and results. In this episode, you'll learn: What to say when deadlines are missed & how to fix the real issue The simple question that drives ownership & initiative How asking "when" changes your team culture To learn more about Gina, click here. Connect with her on LinkedIn. Read about her company, Athena Executive Services at this link. Time Stamps 00:57 – Gina's business growth through rapid expansion & market shifts 11:56 – Why delegation without accountability fails 20:28 – Shifting ownership: "What do you need from me?" 22:24 – The power of asking "when" in every meeting 26:30 – What to do when work is not completed on time 28:02 – The million-dollar question: "What got in the way?" 33:59 – Why caring deeply gives you room to hold people accountable 40:03 – Negotiating deadlines without lowering standards This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!]]>

"At some point in the future, somebody's going to be watching a movie about our era and there's going to be a human bookkeeper. And they're going to turn to their parents 20 years from now, and they're gonna say, 'Bookkeepers used to be people? That's so weird. I thought they were always artificial intelligence. I thought they were always computers.'" -Joe Woodard In this spotlight episode, founder of Scaling New Heights, Joe Woodard shares a clear view of where the bookkeeping profession is heading as AI reshapes the industry. He breaks down how service models are evolving, why advisory must be structured differently, and what practical steps you can take today to stay relevant and valuable plus much more! In this episode, you'll learn: How to use AI safely while protecting client data The difference between AI-enabled tools & native AI platforms How to structure your services using "swim lanes" instead of pricing tiers To learn more about Joe, visit his LinkedIn profile here. To get your ticket for Scaling New Heights, click this link. Time Stamps 00:53 – Introduction to Joe Woodard & what's new since his last visit 02:15 – Why advisory is becoming the core value in bookkeeping 04:20 – Moving from pricing tiers to service "swim lanes" 06:04 – Breaking down transactional, controllership, FP&A & outsourcing 08:26 – How subscription models change pricing & scope conversations 10:16 – Why managing scope is harder than managing profitability 12:11 – How to handle scope creep using swim lane language 15:23 – Pricing differences for small versus larger clients 16:22 – The impact of AI on bookkeeping & accounting 18:03 – Book recommendations to understand the future of work 20:14 – The "Hidden Figures" lesson every bookkeeper should understand 22:18 – Two paths to adopt AI in your firm 25:41 – Native AI tools versus AI layered on existing platforms 28:34 – How to protect client data when using AI 32:21 – Practical advice for using tools like ChatGPT safely 35:36 – Scaling New Heights conference & what to expect Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"Oftentimes we get into burnout because we are saying yes to everything. We're getting scope creep, and we aren't billing for those extras."–Linda Hunt In this episode, the author of The Money Conversation: Speak the Truth. Set the Standard. Get Paid Without Apology, Linda Hunt explains why burnout often starts with unclear boundaries and underpriced services. She shares practical strategies to help you calculate your true capacity, package your services properly, manage scope creep, and position yourself as a strategic partner without overextending yourself or your team. In this episode, you'll learn: How to calculate your Minimum Aligned Price & set a sustainable pricing floor How to recognize scope creep & confidently charge for extra work How AI can free up time for deeper analysis & advisory conversations To learn more about Linda and her company, SumSolutions, click here. Connect with her on LinkedIn. Buy her book, The Money Conversation at this link. Time Stamps 01:06 – Linda's journey from corporate to building a remote accounting firm 04:25 – Why lack of structure leads to burnout 08:37 – Calculating your Minimum Aligned Price 13:55 – Assigning clients to specific days to improve focus 17:37 – Structuring annual packages & dividing by 12 19:10 – What scope creep looks like in real life 22:42 – Turning extra requests into paid projects 28:33 – Using AI to elevate your advisory role 34:25 – Linda's pricing reset session & upcoming book, The Money Conversation This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!]]>

"We always say 'Motivation is like a shower. You should visit it daily.' You have to keep yourself motivated every day. How do I get myself motivated and sold back on myself so that I can be the best version of how I want to show up for my clients?" –Julee Gracey In this episode, sales and marketing coach, speaker, and author of Highly Confident, Julee Gracey explains why confidence is the foundation of pricing, pitching, and growing a bookkeeping business. She shares practical strategies to help you strengthen your internal dialogue, communicate your value clearly, and attract higher-quality clients who are willing to pay for your expertise. In this episode, you'll learn: How to stop underpricing & stand firm behind your fees Why you must get sold on yourself before you try to sell your services How to identify your ideal clients & speak directly to their needs To learn more about Julee, click here. Follow Julee on Instagram. Get a copy of Highly Confident. Time Stamps 00:55 – Introduction to Julee & her background in sales 06:17 – Why confidence is required before you can sell 09:29 – Rewiring negative self-talk & managing imposter syndrome 12:49 – The difference between selling & closing 14:53 – Why you should stop handing out business cards 18:59 – Understanding the three types of clients 25:49 – How to overcome fear of networking events 32:09 – Shifting from price focus to return on investment 35:14 – A real example of raising prices & holding firm 39:17 – Overview of Julee's book Highly Confident This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!]]>

" In order to create that trust, you have to be honest enough to know that you're not the right person for everybody. But those people that you do connect with, when you find that connection, that is when you can start to go through that process." –Amy Jacobson In this episode, Australian emotional intelligence expert, speaker, and author of The Emotional Intelligence Advantage: Mastering Change and Difficult Conversations, Amy Jacobson explains why technical skill alone will not build a strong, sustainable bookkeeping firm. She shares how emotional intelligence drives trust, strengthens client relationships, and improves leadership inside growing firms, along with a practical five-step framework you can apply immediately. In this episode, you'll learn: How emotional intelligence builds client trust & retention How to adapt your communication style to different clients Why leadership requires a different skill set than bookkeeping To learn more about Amy, click here. Connect with her on LinkedIn. Buy her book, The Emotional Intelligence Advantage: Mastering Change and Difficult Conversations, at this link. Time Stamps 01:11 – Amy's background & her path into emotional intelligence 04:14 – A clear definition of emotional intelligence for business owners 06:08 – Where bookkeepers commonly struggle with EQ 08:58 – How trust is built through real connection 11:12 – The five-step emotional intelligence framework 13:59 – A real example of client loss due to poor communication 16:58 – Shifting from technical language to client-centered language 19:58 – Becoming part of the client's business instead of an outside vendor 22:32 – Why leadership is not the same as technical skill 26:01 – How reactive leadership drains time & energy 28:48 – A simple daily question to improve emotional intelligence 30:29 – Where to access Amy's books and free tools This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!]]>

"The biggest one and the most impactful one is not making the time every week to work on the business. They get themselves into the rat race. They spend the money on these programs, and then they don't make the time to implement them. That's the biggest mistake that I see. Do the hard things 'cause we can all do hard things and it's okay if we screw up."–Teresa Slack In the final episode of this four-part series, co-founder of Financly Bookkeeping Solutions, Teresa Slack shares how her bookkeeping firm shifted from survival to stability by building the systems, pricing, and team structure needed to scale. She breaks down the decisions that increased profitability, supported growth, and turned the firm into a sellable asset, along with the real challenges of restructuring roles, working through setbacks, and preparing for a successful exit. In this episode, you'll learn: What made the firm scalable & no longer dependent on the owners Why systems, profitability & cloud operations increased business value What buyers actually looked for when acquiring the firm Click here to learn more about Teresa and email her at [email protected]. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool she used to turn her business around). Click here to join the VPA on Skool platform free training and support. Time Stamps 01:43 – Realizing the business was no longer fragile 02:04 – Setting new goals for growth & team support 03:26 – Building benefits & a sustainable work environment 04:22 – Turning revenue goals into clear action plans 05:46 – Growth setbacks & unexpected challenges 07:15 – Restructuring roles into bookkeepers & client managers 09:33 – Why the transition was harder than expected 12:01 – Systems that finally made the new structure work 13:36 – How role clarity improved efficiency & client service 14:59 – Using outsourced bookkeeping to support scale 16:41 – When selling the business became a real option 18:16 – Choosing buyers who aligned with the firm's values 20:09 – What increased the firm's valuation 22:55 – Preparing financially before selling 25:19 – Why systems & owner independence matter to buyers 27:22 – Lessons learned after selling the firm 28:37 – The biggest mistakes Teresa sees firm owners make 30:02 – What's next for Teresa & how she supports other bookkeepers Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"You can have all the great checklists and all the great systems for quality bookkeeping and you can hire all the right people, but if you don't know how to price your services, you are going to fail. You will not be profitable."–Teresa Slack In part three of this four-part series, Teresa Slack, co-founder of Financly Bookkeeping Solutions, shares the phase where momentum finally began to build. After resetting the firm, she and her sister shifted their focus to working on the business, not just surviving inside it, and made real progress through uncomfortable pricing conversations, focused implementation time, and disciplined investment in systems and training. In this episode, you'll learn: Why systems alone are not enough without proper pricing The difference between fixed pricing & true value pricing How Teresa increased prices & discovered clients were willing to pay To learn more about Teresa, click here and email her at [email protected]. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool she used to turn her business around). Click here to join the VPA on Skool platform free training and support. Time Stamps 00:54 – Entering the phase where momentum begins to build 02:29 – Why poor pricing guarantees failure, even with great systems 03:29 – Fixed pricing versus value pricing explained 04:22 – Presenting higher prices & hearing clients say yes 05:47 – Making large investments without feeling ready 06:40 – Closing Fridays to work on the business 08:17 – Turning training into real results through implementation 09:35 – Fixing pricing mistakes & rebuilding confidence 12:02 – Hiring experienced bookkeepers using structured systems 13:56 – Why skills alone are not enough without the right mindset 18:09 – Building a training process that sets staff up for success 20:16 – Repricing existing clients & facing the fear 22:09 – Increasing revenue by 45 percent in six weeks 23:27 – Losing the wrong clients & moving forward stronger 24:16 – What's coming in the final episode Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"We can do hard things even though you're afraid, even though you don't know if it's going to work. You have to try. You have to do different things and you will fail. And that's part of the growth. Part of the learning is to not be afraid to take that leap." –Teresa Slack In part two of this four-part series, Teresa Slack, co-founder of Financly Bookkeeping Solutions, shares the breaking point that forced her and her sister to reset their firm. With the business no longer working, they made hard calls that led to Financly 2.0, including letting staff go, rebuilding client trust, and investing money they didn't have into systems, coaching, and pricing education. In this episode, you'll learn: How poor hiring & hourly pay created bigger losses as the firm grew The difference between fixed pricing & true value pricing How investing in systems &coaching changed how they viewed their value To learn more about Teresa, click here and email her at [email protected]. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool she used to turn her business around). Click this link to join the VPA on Skool platform free training and support. Time Stamps 01:19 – Hitting the breaking point & questioning whether to continue 01:43 – Deciding to rebuild the firm from the ground up 02:23 – Investing in systems & support with no margin for error 02:44 – Letting staff go & repairing client relationships 03:56 – Realizing pricing was a major problem 04:52 – Discovering value pricing for the first time 05:13 – Rolling out fixed packages & why it made things worse 06:11 – Paying staff more than clients were paying the firm 06:57 – Committing to hard changes & doing things differently 07:40 – Investing in pricing education despite fear 08:14 – Learning to believe in the value of bookkeeping work 09:35 – Having pricing conversations without panic 11:18 – Why systems & hiring processes became the turning point 15:04 – What's coming next in part three Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"The mission was always to build a million dollar bookkeeping firm. Our goal was to grow a large bookkeeping firm with clients and staff across Canada. That's what we wanted to do. And that's kind of what we are now." –Teresa Slack In part one of this special four-part series, Teresa Slack, co-founder of Financly Bookkeeping Solutions, shares the honest story of launching a virtual bookkeeping firm in 2014 with big goals, low pricing, and no clear path to profit. She shares how her business grew fast and looked successful on paper, but behind the scenes the pressure was intense as underpricing, early hiring, and years without owner pay slowly drained the firm and took a personal toll. In this episode, you'll learn: Why rapid client growth exposed serious pricing & margin issues What really happens when you hire staff before fixing your business model How fear, stress & lack mindset show up when owners stop paying themselves To learn more about Teresa, click here & email her at [email protected]. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool Teresa used to turn her business around). Click here to join the VPA on Skool platform free training & support. Time Stamps 01:14 – Launching a virtual bookkeeping firm in 2014 03:15 – Using cloud tools & early adoption of QuickBooks Online 03:35 – Running free financial literacy seminars to attract clients 04:01 – Growing from five clients to dozens across bookkeeping, tax & consulting 04:21 – Feeling overwhelmed & deciding to hire staff 05:09 – Charging hourly rates that left no room for profit 06:06 – Paying staff & overhead while taking no income 07:03 – Driving hours to Toronto to build a client base 08:25 – Why the numbers looked good but the business wasn't healthy 08:44 – The original vision to build a million-dollar firm 09:50 – Not getting paid & questioning personal success 10:34 – Realizing they needed help but feeling unable to afford it 11:16 – Fear, lack mindset & pulling from savings to make payroll 12:39 – The emotional strain of running a business with a sibling 13:18 – Creating "business hat" conversations to manage conflict 14:20 – Keeping communication open during stressful seasons 14:43 – What's coming next in part two Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"The hardest thing is to not try and solve their problem in the sales interview, just listen to the business case, and then come up with clever ways to achieve that business case really as easily as you possibly can. So you're looking for smaller projects, not bigger projects. It's, it's a complete mind shift." -Jonathan Stark Jonathan Stark, author of Hourly Billing is Nuts, breaks down why hourly billing holds you back. He shares how shifting to value-based pricing changes your income, your clients, and your time. Jonathan explains how writing, teaching, and niching help you stand out, and why clients buy outcomes, peace of mind, and confidence, not hours. In this interview, you'll also learn: Why hourly billing rewards inefficiency & limits growth What mindset shifts you need to stop selling time How specialization & authority support higher pricing To learn more about Jonathan, click here. Get a copy of his book, Hourly Billing Is Nuts, at this link. Connect with him on LinkedIn. Time Stamps 00:58 – Why hourly billing is nuts & how Jonathan discovered it 04:00 – Discovering value-based fees & applying them in year one 05:40 – Breaking the habit of scoping during sales calls 09:18 – Pricing options based on outcomes, not deliverables 11:30 – How fixed pricing improves trust & client behavior 16:21 – Connecting your work to revenue growth or cost reduction 18:55 – Selling peace of mind as a measurable outcome 20:58 – Why working fewer hours should not mean earning less 22:31 – How AI & automation increase value, not risk 25:35 – Why predictable pricing benefits both you & your clients 29:00 – Identifying what different clients truly value 31:09 – Letting go of poor-fit clients to grow sustainably 36:10 – Why Jonathan wrote Hourly Billing Is Nuts 38:57 – Books that support the shift away from hourly billing 42:17 – What it means to "own your authority" 44:25 – Why being different matters more than being cheaper 47:07 – Using specialization to escape price competition 48:57 – Writing as a long-term growth strategy 50:12 – Where to find Jonathan's free resources Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"Slow down. I think we move so fast and we're trying to go in straight to the solution and there could be multiple things that the customer needs and we miss opportunities when we move too fast." -Syvonia Brown In this Spotlight episode, Syvonia Brown, Director of Sales at Sage 50 US, talks about emotional intelligence and why it matters more than most bookkeepers realize. She shares practical ways to handle tough client conversations, slow down reactive thinking, and build trust without taking on unnecessary stress. In this interview, you'll learn: How active listening changes difficult client conversations Why silence can be a powerful communication tool How to show empathy without absorbing client emotion To learn more about Syvonia, click here. Explore Sage at this link. Time Stamp 01:20 – What emotional intelligence really means in client work 02:10 – Checking in with yourself before client conversations 02:55 – Why jumping to solutions causes problems 04:25 – Using silence to help clients feel heard 05:17 – Simple techniques to avoid filling the silence 06:46 – Phone, video, or email how & tone changes everything 10:42 – Empathy without taking issues personally 12:21 – Why apologizing can make things worse 14:06 – De-escalating upset clients without matching their tone 16:14 – Taking accountability when mistakes happen 18:30 – Handling issues when you don't know the full story 20:01 – Embedding emotional intelligence into firm culture 21:22 – Training teams to lead with empathy 23:21 – How emotional intelligence drives loyalty & referrals 25:29 – Practical habits bookkeepers can apply immediately Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

" Selling is not necessarily the answer. Exit can mean continuing to be part of it, but in a different way." –Salim Omar In this episode, Salim Omar, CPA and author of The CPA Firm Exit Playbook, shares what it takes to build a firm that works without constant owner involvement. Drawing from 30 years as a firm owner, Salim explains how systems, marketing, and leadership shape firm value and future options. In this interview, you'll learn: Why owner dependency limits growth & firm value How systems & teams prepare your firm for the next chapter What buyers actually look for in an accounting firm To learn more about Salim, click here. Get a copy of his book, The CPA Firm Exit Playbook. Connect with him on LinkedIn. Time Stamp 01:49 – Salim's journey from CFO to firm owner 04:22 – Discovering The E-Myth & changing how he ran his firm 06:03 – Shifting from technician to business owner 08:49 – Leading with curiosity & leaving ego behind 12:37 – Why Salim wrote The CPA Firm Exit Playbook 14:14 – The biggest exit planning mistakes firm owners make 16:15 – Removing owner dependency years before selling 18:21 – Why growth & marketing matter to buyers 22:49 – Education-based marketing & attracting better clients 29:01 – Redefining exit without fully stepping away 30:59 – Straight Talk Transitions & available resources Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

" We need to do things that the other people aren't doing because that's how you make ways, that's how you revolutionize, that's how you pave a new path for the other people that think like you, but maybe don't have the strength at this point yet to pave the way." -Sharrin Fuller In this episode, Sharrin Fuller, strategic advisor and founder of Glass Wallet Ventures, shares why she believes the future of bookkeeping is client-facing, relationship-driven, and systemized. She breaks down how she scaled smarter, reduced her team, embraced technology, and rebuilt her firm to run smoothly with less effort. Sharrin also shares the thinking behind her book, Unfollow The Rules: The Messy Truth About Burnout, Bad Decisions And Building Until It Worked and why challenging traditional models matters more than ever for firm owners. In this interview, you'll learn: Why scaling smarter beats hiring more staff How technology replaces tasks but not relationships What bookkeepers must do to stay relevant as AI advances To learn more about Sharrin, click here. Connect with her on LinkedIn. Buy her book, Unfollow The Rules, at this link. Time Stamp 00:00 – Why only client-facing roles matter in the future 01:03 – Sharrin's career journey & building multiple firms 03:47 – What inspired her book Unfollow The Rules 11:23 – Scaling smarter without adding people 12:23 – Reducing a team from 12 to 2 without losing clients 14:45 – Challenging traditional business models 19:53 – How to decide what to outsource or automate 24:08 – The downside of fast-changing technology 27:56 – What Sharrin is building next & where to find her Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"Your data is good to go. Customer comes into Hub Analytics and starts chatting with the chat bot to ask questions about the data, get visualized charts and graphs, and really have kind of this virtual CFO experience, which is cool." -Tommy Vincent Tommy Vincent, Co-Founder and Chief Revenue Officer at Hub Analytics, returns to explain how AI is reshaping analytics, advisory, and the bookkeeper's role. He shares how data diagnostics improve pricing confidence, why early forecasting matters, and how AI tools give clients clearer financial insight without added complexity. In this interview, you'll learn: How AI checks bookkeeping work in seconds & catches errors early Why forward-looking analytics matter more than past reports How to deliver CFO-level insight without becoming a CFO To learn more about Hub Analytics, click here. Connect with Tommy on LinkedIn. Time Stamp 00:00 - How AI scans bookkeeping data & flags issues 02:13 - Why AI fits naturally into accounting & finance 05:01 - Using AI to validate work & reduce review time 06:22 - Moving from historical reports to forward-looking insight 08:37 - Why many bookkeepers don't want to deliver CFO services 09:13 - How the Hub Analytics partner program works 11:45 - Using data diagnostics to check & price new clients 14:22 - Catching errors & unknowns before onboarding 16:10 - Why small businesses need forecasting earlier 19:36 - Cash flow forecasting & scenario planning 20:34 - Using AI chat tools as a virtual CFO 22:32 - Turning insights into real business decisions 25:02 - How bookkeepers stay connected to advisory work 29:57 - Making CFO-level insight affordable for small businesses 32:14 - How to get started with Hub Analytics

" I'm not gonna say people can't change. What I will say is that it is hard work to change attitude. Changing skills, super simple. Attitude, it's a losing battle for the vast majority of business leaders." -Mark Murphy Welcome to 2026 and the 10th anniversary year of our podcast! In this episode, Mark Murphy, founder of Leadership IQ, shares how to hire better and build teams that actually work. He explains why most hiring problems come down to attitude and outlines the five roles every strong team needs. In this interview, you'll learn: •The five roles every winning team needs • How to ask interview questions that reveal real behaviour • Why attitude—not skills—is behind most failed hires To learn more about Mark and Leadership IQ, click here. Connect with him on LinkedIn. Time Stamp 00:00 Mark shares why attitude makes or breaks new hires 04:10 The real reasons nearly half of new hires fail 08:30 How to ask interview questions that reveal the truth 14:30 Why managers ignore red flags & how to stop 20:20 The five roles every winning team needs 29:30 How business owners can stop trying to be "everything" 33:40 Adaptive hierarchy & better decision-making 37:50 Leading remote teams with clearer roles 44:10 Where to learn more about Mark Murphy & Leadership IQ

"Ethics and integrity are a bookkeeper's superpower." -Heather Smith Kick off your new year with clarity and momentum in this special Year-In-Review episode! Host, Michael Palmer brings together an international panel of leaders to unpack the biggest wins, surprises, and lessons from 2025. This conversation gives you a grounded look at what actually changed in the bookkeeping world and what you can expect moving into 2026. You'll hear real stories from Canada, Australia, and the United States about technology shifts, economic pressures, client transformations, team challenges, and the rising demand for advisory. Our final episode of 2025 is packed with insights that you don't want to miss! Thank you so much for listening to our show and being a part of our community! Your support is the reason this podcast continues to grow. Wishing you a HAPPY and SUCCESSFUL 2026! To find out more about our guests, click below: Lisa Campbell Teresa Slack Heather Smith Christina Springstead Time Stamp 01:11 – Michael introduces the Year-In-Review panel 03:38 – Biggest surprises from 2025 04:51 – How bookkeepers embraced AI 05:12 – Personal breakthroughs & executing on training 07:04 – Economic pressures & global ripple effects 11:24 – Setbacks bookkeepers faced this year 16:41 – Capacity challenges & communication gaps 19:22 – Heartwarming client wins 23:05 – Helping clients understand their numbers 27:23 – The ripple effect bookkeepers create 30:03 – Why new bookkeepers matter 32:16 – Heartbreaks & financial vulnerability 34:06 – Ethics as a bookkeeper's superpower 39:26 – What worked well in 2025 40:10 – Hiring support to free up time 42:12 – Workflow systems paying off 46:11 – What didn't work & lessons learned 49:26 – Overwhelm from too much change at once 50:59 – Trends shaping 2026 54:58 – The rising need for human connection 1:02:37 – Personal focus areas for 2026 1:05:05 – Closing thoughts & New Year wishes

"You get to a place little by little of just working with these wonderful people that really appreciate what you're doing. They're paying top dollar and you love what you're doing." -Lisa Campbell Lisa Campbell, author of Beyond Bookkeeping and bookkeeping mentor, joins host Michael Palmer for part two of this special live series recorded at Accountex Canada 2025 at the Metro Toronto Convention Centre. She shares how to filter ideal clients, step into advisory with confidence, and build a business that supports your life—not drains it. In this interview, you'll learn: Why most bookkeepers already are doing advisory without realizing it One simple step you can take this month to start leading clients How boundaries create freedom and stronger client relationships To learn more about Lisa, click here. Connect with her on LinkedIn. Order a copy of Beyond Bookkeeping. Time Stamp 01:09 – The biggest myths bookkeepers believe about advisory 02:25 – Why you're more qualified than you think 03:08 – The one conversation that can start your advisory journey 04:40 – How honesty builds trust & opens deeper client relationships 06:32 – Systematization as the path to freedom 07:36 – The emotional toll of staying stuck & overwhelmed 08:13 – Why boundaries matter & how to set them 09:36 – Stopping late-night messages, constant emergencies & scope creep 11:02 – Charging premiums for urgent work 11:50 – Seeing yourself as a leader, not a laborer 12:47 – The mindset shift that unlocks real advisory 13:39 – Why losing the wrong clients makes space for the right ones 15:24 – How ideal clients show up when you raise your standards 20:19 – Building your business mindset through learning and curiosity 22:01 – Differentiating yourself from low-cost competition 24:17 – How niching creates authority & demand 25:08 – The future of bookkeeping and the rise of AI-supported advisory

"You learn, you read, you surround yourself with other people. Don't stay isolated behind your computer. You come to things like this. You join groups, you learn what other people are doing, and a lot of it is just understanding the value yourself." -Lisa Campbell Lisa Campbell, author of Beyond Bookkeeping and longtime bookkeeping mentor, joins host Michael Palmer for a special two-episode series recorded live at Accountex Canada 2025 at the Metro Toronto Convention Centre. She shares how a single "midnight moment" pushed her to rebuild her business, break free from burnout, and step confidently into advisory work. In this interview, you'll learn: What finally broke the cycle of burnout & overwork How systemizing business unlocked time, freedom & new opportunities Why shifting from compliance to advisory starts with mindset To learn more about Lisa, click here. Connect with her on LinkedIn. Order a copy of Beyond Bookkeeping. Time Stamp 01:16 – Lisa shares her "midnight moment" & the push to change everything 03:14 – The shift from having a job to building a business 06:16 – How burnout & overwork showed up in her daily life 07:03 – The mindset change that unlocked growth 08:12 – What "beyond bookkeeping" really means 09:17 – The moment she realized her systems were working 10:26 – How long it took to make the shift & why timing is different for everyone 11:46 – Breaking through time constraints & building structure 12:44 – How she stayed connected to her why during tough seasons 15:11 – How Profit First transformed her business & her clients' 16:20 – Why more clients doesn't equal more profit 18:10 – Moving from hourly work to value & subscription pricing 18:53 – The hidden gold bookkeepers give away for free 20:12 – Why learning, community & awareness help you charge your value 21:23 – Lisa's exercise to uncover value adds 24:12 – How she rewired her thinking & found new opportunities 25:16 – Shifting from compliance work to advisory 26:50 – Building an ecosystem for the entire client journey

" You do not want a business that is entirely dependent on you. You want an independent running business." -Ron Bester Ron Bester, VP of Client Experience at Successful Bookkeeper Global, breaks down why so many bookkeepers feel buried in day-to-day work and how the SODA framework helps you reclaim time, reduce stress, and build a business that doesn't rely on you to survive. In this episode, you'll learn… How to spot where your time is leaking & fix it Build simple systems that remove bottlenecks Use automation to cut repetitive tasks & free up hours Connect with Ron on LinkedIn. Time Stamp 00:00 – Why running a business is different from doing work you enjoy 03:00 – The common pitfalls small business owners face 07:00 – Why every business needs a plan, systems & an exit strategy 10:00 – Introduction to the SODA framework 12:00 – Systemize: building processes that create consistency 15:00 – Outsource: letting experts handle non-core work 17:00 – Delegate: breaking the "only I can do it" mindset 20:00 – Automate: using tech to remove repetitive tasks 23:00 – The biggest transformation bookkeepers experience with SODA 26:00 – Early wins & what shifts first 28:00 – Why most owners don't realize they are the bottleneck 30:00 – One small action you can take today 31:00 – How the SODA pre-checklist and intensive work 33:00 – Building a business that runs independently of you

"Like this is not just a gig, but this is my career. You grow into wanting more of that for your clients and you start recognizing if a client isn't about that. The last thing I want is just agree to do a subpar job because a client doesn't really care and then they decide to care in two years and they look back at the history and they're like, 'This has been a mess.'" -Christina Springstead Christina Springstead, owner and founder of Springstead Solutions, returns to share what she's learned from handling complex cleanups and growing her business with intention. From refining systems to managing client expectations, Christina explains how bookkeepers can balance quality, communication, and growth—without burning out. In this interview, you'll learn: How to spot hidden issues in cleanup projects before you quote Why communication & transparency build client trust How to manage pushback & set professional boundaries To learn more about Christina and Springstead Solutions, here. Connect with her on Linkedin. Time Stamp 02:13 – Christina shares her background & path back to bookkeeping 04:34 – Lessons learned from recent cleanup projects 06:00 – The hidden costs of missing bank feed data & auto rules 07:42 – When CPA journal entries hide deeper problems 08:42 – How cleanup checklists evolved into better systems 09:41 – Why deeper diagnostic reviews protect both client & bookkeeper 10:56 – Expecting problems: guilty until proven innocent approach 11:51 – When "accurate" AR & AP numbers aren't accurate at all 13:35 – The danger of ignoring small errors today 14:24 – How to handle client pushback with transparency & purpose 15:12 – Choosing clients who care about accurate books 16:03 – Why clean books protect long-term business value 17:10 – Setting boundaries & recognizing red flags in clients 18:37 – The difference between hobby clients & business-minded ones 19:16 – Holding clients accountable for financial quality 19:52 – Managing stress & staying flexible during heavy work periods 21:35 – Communicating delays honestly with clients 22:47 – Building trust through consistency & openness 24:31 – Why clear communication increases client value perception 25:51 – Real client story: turning nonprofit chaos into clarity 27:45 – How bookkeeping education empowers boards & leaders 30:11 – Hiring a VA and assistant to buy back time & focus 31:43 – Building a business around your lifestyle, not fear 32:31 – Manifesting growth & designing your dream business 33:53 – Recommended books: Who Not How & Buy Back Your Time 36:23 – Why mindset, focus& vision drive real success 39:02 – How the new Summit experience connects the bookkeeping community This episode is brought to you by our amazing friends at Hub Analytics! Imagine having all your financial data in one place, with real-time analytics and customized reports at your fingertips. Hub Analytics is a financial platform that streamlines bookkeeping operations, so you can focus on what really matters—delivering high-quality results for your clients. With Hub's easy-to-use tools, you'll save time, reduce errors, and gain deeper insights into your clients' financials! Ready to take your bookkeeping to the next level? Book a demo to learn more and start your FREE trial TODAY!]]>

"Do not be tempted to undervalue yourself just because it happens to be something that's fast or easy for you to produce." -Casey Brown In the finale of this two-part series, pricing expert and president of Boost Pricing, Casey Brown, returns to share how bookkeepers can move from fear-based pricing to confident, value-driven conversations. She explains how to stop pre-discounting, test your true pricing ceiling, and communicate your worth with clarity and confidence. In this interview, you'll learn: Why pre-discounting hurts your profits How to identify & attract better, higher-value clients How to package & present your services with confidence Connect with Casey on LinkedIn. To buy her book, Fearless Pricing, click here. Watch her TED Talk, or video on 12 things I Hate About Hourly Billing. To learn more about Boost Pricing, click this link. Time Stamp 02:03 – The two types of discounting: negotiated & pre-discounting 03:52 – How to test your true price ceiling 04:54 – Overcoming scarcity mindset & fear of losing clients 06:02 – Why fewer clients at higher prices can be more profitable 07:31 – Letting go of price-sensitive clients who drain your energy 09:30 – Why bad clients cost more than they're worth 10:00 – The gender gap in business pricing & confidence 11:32 – How women undervalue their services & why it costs them 12:39 – Messaging & packaging your services for higher value 14:04 – Half of pricing success is the number; half is how you frame it 15:39 – Stop obsessing over numbers & focus on context 16:34 – The problems with hourly billing models 17:34 – Why fixed-fee & value-based pricing work better 18:13 – When & how to offer pricing packages 19:34 – Avoid overwhelming clients with too many choices 21:15 – Be the expert—guide your client's decision 23:18 – Why clear messaging builds trust & confidence 24:44 – The Picasso lesson: charge for your experience, not your time 25:45 – How to articulate the process & value you deliver 26:08 – Where to find Casey's free resources, book & programs 27:29 – Fearless Pricing community & how to join This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"Bookkeeping is a commodity. My accounting software can be a commodity. So how do we strike that emotional cord and how do we give the confidence that we are the right choice going forward? We're not a commodity. We are differentiating. We're building that difference." -Melanie Spillman Melanie Spillman, Vice President of Sales for Sage US Medium Businesses, shares practical ways bookkeepers can build stronger client relationships—through listening, follow-up, and authenticity. She explores how trust is earned, why active listening matters, and how to keep human connection alive in an increasingly automated industry. In this interview, you'll learn: How to build trust quickly & consistently with clients The art of active listening & letting silence do the work Why understanding your client's past & future builds connection Connect with Melanie on LinkedIn. To learn more about Sage, click here. Time Stamp 01:41 – How to build trust quickly with clients 03:34 – The power of timely follow-up 05:19 – Setting expectations & communicating clearly 06:33 – Teach, tailor & take control in client conversations 07:53 – How to ask better questions & listen actively 09:23 – Staying present & focused during meetings 12:22 – The value of silence in communication 13:54 – Showing authenticity & passion with clients 15:53 – How to build trust in the first meeting 17:22 – Asking about a client's past & future to deepen connection 20:09 – Why focusing only on history limits your impact 21:15 – How to stand out in a competitive market 22:29 – The "front door" story: lessons in emotional connection 25:39 – Why people buy with emotion & justify with logic 27:31 – Turning services from a commodity into a connection 29:34 – Keeping the human touch in an automated world 31:27 – Using AI to free time for more meaningful client work 33:22 – Understanding what really motivates clients 36:48 – Make every client interaction meaningful 38:46 – How Sage uses AI to empower bookkeepers

"It's the bookkeeper who has to sell his or her own services, and so they're not a professional salesperson. So a lot of times there's a lot of fear and we get in our heads, we get in our gut, we feel pushy, we feel salesy, we feel weird and we discount. And so to me, it's about arming the person whose job it is to sell this value with the skills and tools to do it." -Casey Brown In part one of this two-part conversation, pricing expert and resident of Boost Pricing, Casey Brown, joins the podcast to help bookkeepers overcome fear, self-doubt, and hesitation around pricing their services. Drawing from her journey as an engineer turned pricing strategist, she explains how your "money story" shapes your pricing decisions—and how to change it. In this interview, you'll learn: How mindset & money stories limit what you charge The biggest pricing mistake small firms make How to handle pricing objections without discounting Connect with Casey on LinkedIn. To buy her book, Fearless Pricing, click here. Watch her TED Talk, or video on 12 things I Hate About Hourly Billing. To learn more about Boost Pricing, click this link. Time Stamp 00:00 – Why pricing confidence matters for bookkeepers 02:10 – Casey's journey from engineer to pricing strategist 04:38 – Lessons from working at GE & entering the pricing world 05:56 – Shifting from big corporations to small businesses 07:14 – Why analytical pricing models don't work for small firms 08:13 – Helping bookkeepers sell their own value with confidence 10:24 – From pricing analytics to pricing mindset training 12:31 – How training teams led to massive profit increases 13:36 – Why pricing problems start between your ears, not in spreadsheets 15:14 – Common sales beliefs that hold business owners back 17:19 – The myth that "the market sets the price" 18:52 – How changing beliefs can boost profitability 20:18 – Why most people fear talking about price 21:01 – Understanding your personal money story 22:41 – How emotions affect pricing decisions 23:13 – Exercises to detach emotion from pricing 24:22 – Casey's advice for bookkeepers ready to charge more This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!

"We have to stop trading time for money. Hourly billing traps you. It gets you in the cycle of undervaluing yourself. Discounting just to get a client to sign up with you and think that you're going to charge more in the future is another trap. Doing free work, answering quick questions, answering an abundance of emails and never getting paid for it is a trap." -Michelle Weinstein Michelle Weinstein, founder of The Abundant Accountant and The Pitch Queen, talks about how bookkeepers can confidently sell their services without feeling pushy or uncomfortable. Drawing on years of experience helping accounting professionals close high-value clients, Michelle shares simple strategies to increase revenue and build trust with prospects. In this interview, you'll learn: How to overcome fear & hesitation around pricing and sales Questions that turn discovery calls into meaningful conversations How to position your value instead of selling your time To learn more about Michelle, click here. Connect with her on LinkedIn. Time Stamp 00:00 – Why selling is a skill every bookkeeper needs 03:05 – How Michelle helps bookkeepers sell with confidence 05:40 – Shifting your mindset from "selling" to "helping" 07:02 – The biggest mistakes bookkeepers make in sales calls 09:35 – How to ask powerful questions that uncover client needs 12:00 – Why you should never discount your services 14:12 – The difference between pricing & value 16:53 – Turning consultations into lasting client relationships 19:35 – How to talk about money without fear or guilt 22:50 – Using Dext tools to add more value to clients 26:02 – Building confidence through practice & preparation 29:00 – Michelle's top advice for bookkeepers ready to grow 31:20 – Where to learn more about Michelle & The Abundant Accountant This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"The more intentional you get with your money, the more intentional you get with your time as well." -Jennifer Hume In our 500th episode, Jennifer Hume, owner of Coronation Bookkeeping & Tax Services, shares how she built a successful virtual bookkeeping firm and expanded into coaching for real estate professionals. She reveals what worked, what didn't, and how she uses systems, marketing, and speaking to grow her business with purpose and profitability. In this interview, you'll learn: How niching and storytelling drive growth and confidence Why systems are essential for scaling How Jennifer built a $250K firm through referrals To learn more about Jennifer, click here. Connect with her on LinkedIn. Time Stamp 02:03 – Jennifer's journey from family business to starting her own bookkeeping firm 05:28 – Lessons learned from her father's failed business & what she'd do differently 06:08 – The importance of systems & Profit First for building a strong foundation 06:41 – Transitioning from data entry to leadership & advisory work 07:07 – How Jennifer built a $250K firm through referrals & strong processes 09:36 – Learning to market intentionally & step outside her comfort zone 11:54 – Building referral partnerships with accountants & real estate brokerages 13:58 – Overcoming fear & learning to pick up the phone to grow the business 15:58 – How niching into real estate transformed her business 18:33 – Why specializing makes marketing easier & attracts better clients 19:58 – What marketing tactics didn't work (and what to watch out for) 20:59 – Email marketing & newsletters that actually connect 23:46 – How creating a professional speaker's reel set her apart 25:35 – The power of storytelling on stage & building confidence through speaking 29:03 – Using AI tools like ChatGPT to craft speeches & prompts quickly 32:13 – Building a coaching business for real estate professionals 33:47 – Why 90% of realtors quit within five years & how coaching helps 34:31 – How financial & time habits create happier, more balanced lives 36:23 – Where to find & connect with Jennifer online This episode is brought to you by our amazing friends at Hub Analytics! Imagine having all your financial data in one place, with real-time analytics and customized reports at your fingertips. Hub Analytics is a financial platform that streamlines bookkeeping operations, so you can focus on what really matters—delivering high-quality results for your clients. With Hub's easy-to-use tools, you'll save time, reduce errors, and gain deeper insights into your clients' financials! Ready to take your bookkeeping to the next level? Book a demo to learn more and start your FREE trial TODAY!]]>

"The number one driver of small to medium sized businesses not making it is cash flow problems. It's not that they're not profitable. This is the big thing with net cash that most people don't realize, is that you can run a profitable business and run out of money." -Tommy Vincent In this spotlight episode, Tommy Vincent, Co-Founder and Chief Revenue Officer at Hub Analytics, returns to share how bookkeepers can confidently step into advisory by focusing on just 3 key metrics. He explains how to measure, track, and present them to clients in a way that builds trust and drives business growth. In this interview, you'll learn: The 3 metrics every bookkeeper should track Why consistency matters more than dozens of KPIs How net equity shows a business owner's true wealth To learn more about Hub Analytics, click here. Connect with Tommy on LinkedIn. Time Stamp 00:00 – Introducing 3 Key Metrics 02:16 – Why bookkeepers are well-positioned to deliver advisory services 03:59 – Why less is more with KPIs for small business clients 04:54 – The three core metrics 06:33 – Breaking down net operating income & what it reveals 07:50 – Industry nuances & why measuring consistently matters 09:30 – Using consistent monthly tracking to spot improvement 12:20 – Net equity explained 14:27 – Why 78% of a business owner's net worth is tied to their business 16:04 – Loans, distributions & reinvestment 20:54 – Why profitable businesses still fail without cash 23:10 – Healthcare & construction industries & cashflow gaps 25:59 – Watching DSO & DPO to avoid cash crunches 27:21 – How bookkeepers can differentiate by tracking just 3 KPIs 28:29 – How to package advisory 30:55 – Why most existing clients won't pay more 33:18 – Advisory is best suited for businesses over $1M revenue 34:56 – How Hub Analytics supports bookkeepers with AI-driven reporting

"I think that the hacker mindset is a superpower because what it does is it fosters independent thinking. And independent thinking enables a person to observe or discover overlooked pathways, overlooked opportunities, things that other people have missed." -Ted Harrington Ted Harrington, cybersecurity expert and author of Hackable: How To Do Application Security Right and his upcoming book Inner Hacker: A New Way Of Thinking, returns to talk about the hacker mindset and how it can transform both business and life. In this interview, you'll learn: The four traits of the hacker mindset How AI is shaping cyberattacks Ways to tap into your inner hacker To learn more about Ted, click here. Connect with him on LinkedIn. Check out his new book, Inner Hacker: A New Way Of Thinking here. Time Stamp 01:22 – Ted Harrington returns with his new book Inner Hacker 02:47 – Why thinking like a hacker is a superpower 08:08 – The four traits of the hacker mindset 11:30 – What holds people back from channeling their inner hacker 17:15 – How the book supports his business & clients 22:04 – AI's role in modern cyberattacks 28:11 – What's changing for small businesses & cybersecurity awareness 31:22 – Why hackers target small businesses 35:27 – Protecting yourself by knowing where you're vulnerable 36:36 – Ted's future plans & keynote speaking This episode is brought to you by our amazing friends at Hub Analytics! Imagine having all your financial data in one place, with real-time analytics and customized reports at your fingertips. Hub Analytics is a financial platform that streamlines bookkeeping operations, so you can focus on what really matters—delivering high-quality results for your clients. With Hub's easy-to-use tools, you'll save time, reduce errors, and gain deeper insights into your clients' financials! Ready to take your bookkeeping to the next level? Book a demo to learn more and start your FREE trial TODAY!]]>

"You have to keep evolving. We're always evolving. Never stop growing. Never stop learning. If you're not happy with what you're doing, there's always a way to change. And you can lean on great thought leaders like this to help you get there. " -Lisa Campbell Lisa Campbell, Founder of Accelerate 2 Advisor, returns for part two of her series about Stephen Covey's 7 Habits of Highly Effective People. She shares practical ways bookkeepers can apply the next four habits to strengthen client relationships, build stronger teams, and sustain long-term success. In this interview, you'll learn: How to create win-win client & team relationships Why discovery calls should focus on understanding, not selling The power of synergy with your team and professional partners To learn more about Lisa, visit her profile on LinkedIn. Sign up for her Masterclass here! Time Stamp 00:00 – Win-win results with accountants through systemized books01:25 – Habit 4: Think win-win 06:57 – Habit 5: Seek first to understand, then to be understood08:43 – Why selling is ongoing & rooted in understanding clients' real needs 11:16 – Listening & trust with clients & team members 14:13 – Habit 6: Synergy 17:08 – Building referral networks & partnerships for growth 20:02 – Niching & connecting with industry vendors & partners for referrals 22:13 – Real-world example: systemized bookkeeping driving strong CPA referrals 23:55 – Habit 7: Sharpen the saw 28:38 – The most transformative habit for bookkeepers 33:48 – How proactive bookkeepers put first things first to reach advisor level 34:44 – Wrap-up & invitation to Lisa's Accelerate to Advisor masterclass This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"The opportunity now is huge with accountants and bookkeepers to provide more of a proactive service, more forecasting, more future visibility. But certain things have to be in place for that to happen." -Paul Lodder Paul Lodder, VP of Accounting Product and Strategy at Dext, discusses how bookkeepers and accountants can use cash flow forecasting and automation to move beyond compliance and become true strategic advisors. In this interview, you'll learn… Why 1 in 4 small businesses face cash flow issues How to make cash flow forecasting personal How automation frees time for advisory To learn more about Paul, click here. Time Stamp 00:01 – Dext study on 500 Canadian SMBs 02:27 – Why 42% fear closure 04:48 – Opportunity in cash flow forecasting 07:22 – Make cash flow personal for clients 10:25 – Cost of manual vs automation 14:39 – 1 in 4 face cash flow issues 18:09 – Barriers: capacity & strategy 20:44 – Scenario planning & sensitivity 23:42 – Key metric: debtor days 27:11 – Charging for automation, value pricing 32:28 – Tech plus relationships build trust 37:29 – More conversations, more advisory 38:17 – Where to find the Dext study This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!

" Beginning with the end in mind is very helpful for people who are starting, but also for people who are already in the weeds and they just like, 'I can't do this anymore. I need to do something else.' Figure out what it is that you want to build and then reverse engineer it and build it." -Lisa Campbell Lisa Campbell, founder of Accelerate 2 Advisor, shares how to apply the first three of Stephen Covey's 7 Habits of Highly Effective People directly to your bookkeeping business. In this interview, you'll learn: Why being proactive creates stronger client relationships How to begin with the end in mind to design the business you want The importance of putting first things first & delegating effectively To learn more about Lisa, visit her profile on LinkedIn. Sign up for her October 20th Masterclass here! Time Stamp 00:01 – Importance of systemizing every transaction for accurate books 01:04 – Focus on Stephen Covey's first three habits 02:11 – Lisa shares her backstory: from overwhelmed bookkeeper to mentor 03:26 – Discovering Pure Bookkeeping & freeing time to grow beyond data entry 04:45 – Building the Accelerate to Advisor Mastermind program 06:30 – Lisa introduces Level Up Live & her sessions on Covey's habits 09:13 – Habit 1: Be proactive 14:07 – Habit 2: Begin with the end in mind 20:02 – Habit 3: Put first things first This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"Anyone who grows plants knows that sometimes you have to trim the leaves to have an overall healthy plant. Not every customer will come with you as you grow your business, and that's actually a good thing. It keeps your business efficient and healthy." -Etinosa Agbonlahor In the finale of this two-part conversation, Etinosa Agbonlahor, behavioral economist and CEO of Decision Alpha, returns to share practical strategies for raising prices without losing confidence or clients. She explains how to overcome resistance, use behavioral nudges, and position your services to attract the right customers. In this interview, you'll learn: How to spot signals your pricing is off Simple nudges & choice architecture that boost client acceptance How to raise prices with confidence & retain long-term relationships To learn more about Etinosa, click here. Connect with her on LinkedIn. Learn more about Decision Alpha. Download your free Behavioral Pricing Playbook here. Time Stamp 03:01 – The fear of losing customers & why churn can be healthy 07:23 – Building confidence to justify premium pricing 11:16 – Signals your pricing isn't working 18:01 – Behavioral nudges that influence client choices 25:27 – Using choice architecture to present pricing 29:28 – Raising prices while honoring long-term clients This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"You should be distinct enough and positioned just a bit enough that people go, 'Oh, I am caring about the value they're gonna bring to me, to the point where I wanna double click.'" -Etinosa Agbonlahor Etinosa Agbonlahor, behavioral economist and CEO of Decision Alpha, shares how pricing is about more than numbers. She explains why understanding your value and talking to clients is key to building a profitable bookkeeping business. In this interview, you'll learn: Why most bookkeepers underprice their services How client conversations uncover real value Ways to position yourself so price isn't the only factor To learn more about Etinosa, click here. Connect with Etinosa on LinkedIn. Learn more about Decision Alpha. Download your free Behavioral Pricing Playbook here. Timestamps 02:32 – Etinosa's career journey in finance & behavioral economics 04:57 – Why businesses leave 11% profit on the table 07:56 – The number one mistake in pricing: not talking to customers 09:58 – How bookkeepers often copy pricing from competitors 12:41 – Should you show prices on your website? 14:16 – Positioning: are you in the bazaar or the premium store? 17:48 – Differentiation through unique processes or systems 20:01 – Telling your story to build perceived value This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"Just having the courage to allow some of your real story to come through publicly is your differentiator. It builds trust, opens doors to sales conversations, and draws future customers to you." –Jess Jensen Jess Jensen, co-founder of Co-pilot Communications, is back for the second part of this powerful conversation. In part one, she revealed why your personal story is the ultimate marketing tool. Now, she's sharing how to put it into practice with a clear, step-by-step framework for building a digital presence that feels authentic, consistent, and achievable. From breaking through inconsistency, to leveraging AI for content ideas, to showing just the right kind of imperfection—Jess shares practical strategies small business owners can use to show up online and grow their influence. In this interview, you'll learn… How to overcome the biggest barrier to showing up online: inconsistency Why the right kind of imperfection can make you more trustworthy than polished content How AI can accelerate your content creation while still keeping your voice authentic To learn more about Jess, click here. Connect with her on LinkedIn. For listeners of the show, Jess is offering quick, practical 25-minute reviews for business owners and senior leaders who think their profile might be holding them back. You'll get a real-time audit and a handful of actionable next steps. Openings begin the third week of October. No cost, no catch, just clarity. Here's the booking link. Time Stamps 00:00 – Why courage & vulnerability build trust 01:25 – Simple ways to dip your toe into posting 02:20 – Why responding matters more than likes 04:04 – The real barrier: inconsistency 06:17 – How AI can help with idea generation 07:53 – Treating AI like a junior employee you train 10:55 – The psychology of showing up online 13:25 – Imperfection as a powerful differentiator 17:03 – Why collaborators & "yes/no" people matter 17:45 – Where to find Jess online & claim your free LinkedIn audit This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"People are interested in other people. So you can talk about your practice or where you see perhaps the industry going down the road, but from a point of view that is informed and experienced and maybe has a little bit of vulnerability woven in." -Jess Jensen Jess Jensen, co-founder of Co-pilot Communications, has helped leaders at Microsoft, Qualcomm, Adidas, and now small business owners across North America build their digital presence. In part one of this two-part series, she shares why personal storytelling is key to standing out in today's crowded market. In this interview, you'll learn… Why personal voices connect more than brand voices How storytelling humanizes small businesses Ways to overcome fear & self-doubt To learn more about Jess, click here. Connect with her on LinkedIn. For listeners of the show, Jess Jensen is offering quick, practical 25-minute reviews for business owners and senior leaders who think their profile might be holding them back. You'll get a real-time audit and a handful of actionable next steps. Openings begin the third week of October. No cost, no catch, just clarity. Here's the booking link. Time Stamps 00:00 – Why people connect with personal stories 01:23 – Journey from global brands to co-founding Co-pilot Communications 03:16 – Helping executives build digital platforms 04:31 – Humanizing brands through leadership voices 05:33 – Applying storytelling to small businesses 08:38 – Overcoming fear & finding your voice 12:31 – Differentiation: "Differences sell, similarities don't" 14:54 – Step 1: Define your "audience of one" 19:14 – Step 2: Clarify what you want to stand for 23:24 – Step 3: Practice creating content & iterate 24:27 – Step 4: Build relationships in the comments 25:32 – Preview of part two: Jess's full four-step playbook This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!]]>

"A woman came up to me and said, 'You know, you really get me.' And I thought that's really the mantra I want to kind of go with. I want people to understand that I get what they're saying. I can't be them, but I can translate the pain and the successes that they're having." -Jennifer Kahnweiler Introverted leaders bring unique strengths to the workplace, but they're often overlooked. In this episode, Jennifer Kahnweiler, an expert on introverted leadership, shares how introverts can thrive, influence, and lead with confidence. In this interview, you'll learn: How the Four Ps help introverts succeed in leadership Practical ways introverts can influence without being loud How listening can become a powerful sales advantage To learn more about Jennifer, click here. Connect with her on LinkedIn. Time Stamp 00:00 - Introduction to Introverted Leadership01:57 - The Journey to Understanding Introversion 05:31 - The Evolution of Introverted Leadership 10:22 - Creating Introvert-Friendly Workplaces 13:49 - The Impact of COVID on Introverts 18:43 - Navigating the Changing Workplace 20:02 - Empowering Introverts in the Workplace 21:55 - Embracing Introversion in Leadership 23:28 - The Evolution of the Introverted Leader 25:21 - The Four P's of Introverted Leadership 31:25 - Listening as a Key Skill for Introverts 37:09 - Recognizing & Valuing Personal Accomplishments This episode is brought to you by our great friends at Sage! Drowning in paperwork? AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients. Learn more about AutoEntry or get started for free at Sage.com.]]>

" I think it's important that you go for it. You imagine what that looks like. I didn't go into this with the intention of having a big company. It happened one employee at a time. How do you get the 30 employees? Well, start with one." -Jenny Groberg In this episode, we wrap up a two-part conversation with Jenny Groberg, founder of BookSmarts Accounting and Bookkeeping, where she shares how she turned a small team into a high-performing force, overcame personal challenges, and scaled her business to seven figures. In this episode, you'll learn… Raising expectations & setting clear boundaries How to delegate effectively to focus on growth & leadership Adopting subscription pricing to streamline billing & boost cash flow To learn more about Jenny, click here. Connect with her on LinkedIn. Time Stamp 00:01 – Transition from hobby employees to a committed team 03:55 – Personal recovery journey & building a supportive culture 05:30 – Giving back through scholarships, donations & teaching 11:37 – Shift to subscription pricing & improved cash flow 20:01 – Letting go of toxic clients to safeguard staff 25:37 – Encouragement to set big goals, delegate & believe in yourself This episode is brought to you by our great friends at Sage! Drowning in paperwork? AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients. Learn more about AutoEntry or get started for free at Sage.com.]]>

" When I'd go on appointments I would say, 'You know, I do work with so and so', and then that would kind of just help them feel reassured that I knew what I was doing, but I never pretended to know everything. I would be very upfront. If there's something I don't know, let me do some research and I'll get back to you." -Jenny Groberg Jenny Groberg, founder of BookSmarts Accounting and Bookkeeping, shares her powerful story of building a seven-figure firm from scratch. Listen to this episode to learn how small actions can lead to big wins in your bookkeeping business. In this episode, you'll learn… How a $500 QuickBooks certification launched her business Why asking for client reviews changed everything Ways to scale while balancing family life To learn more about Jenny, click here. Connect with her on LinkedIn. Time Stamps 00:01 – Jenny's start in bookkeeping with no money & two kids 02:43 – The $500 QuickBooks investment that paid off 03:32 – Asking for reviews & building credibility 08:33 – Turning small clients into long-term relationships 17:03 – Hiring the first employee & scaling the team 19:52 – Overcoming setbacks & a traumatic brain injury 31:30 – Keys to growing a seven-figure firm This episode is brought to you by our great friends at Sage! Drowning in paperwork? AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients. Learn more about AutoEntry or get started for free at Sage.com.

" One of the most famous quotes ever from Tony Robbins, this one I take with me every single day. 'Fall out of love with yourself and fall in love with your customer and watch the magic happen'. And you gotta fall in love with your customer. When you fall out of love with what you offer or your package, and you fall in love with your customer, you have a beautiful relationship that happens." -Lynn Gagne-Webb In this episode, we wrap up our two-part conversation with Lynn Gagne-Webb, founder of Custom Bookkeeping. Lynn dives into the challenges of pricing, managing client expectations, and building a bookkeeping business that truly fits your goals. In this episode, you'll also learn... Why understanding communication styles can transform client relationships The pros & cons of hourly billing versus value-based pricing How to handle scope creep without burning out your team To learn more about Lynn, click here. Connect with her on LinkedIn. Time Stamp 01:00 – Intro to part two with Lynn Gagne-Webb 01:44 – Trust & communication with clients 03:26 – Color coding for better communication 05:14 – Airplane analogy for pricing & expectations 08:33 – Handling clients wanting more for less 17:13 – Switching from packages to hourly rates 19:54 – Managing rising costs with the airplane model 24:14 – Flat rate questions & subscription fatigue 28:56 – Adapting to industry changes 31:43 – Focus on loving your customer 32:21 – Courses & Learn Bookkeeping Canada

" You're on your own as a business owner. You're trying to figure out, there's no course that anybody gives you to tell you how to be a business owner." -Lynn Gagne-Webb In the first of a two-part series, Lynn Gagne-Webb, founder of Custom Bookkeeping, shares her journey from the corporate world to running and selling a successful bookkeeping firm. As well, Lynn dives into her unique approach to building a team, and reveals how creating a culture of trust and flexibility helped her attract and keep loyal staff for years. In this episode, you'll also learn... The struggles of being a business owner The importance of taking CEO time to review your own business health How to focus on leading your business To learn more about Lynn, click here. Connect with her on LinkedIn. Time Stamp 01:23 – Lynn shares her journey from corporate to entrepreneurship 03:37 – Lynn's vision for supporting small business owners 04:18 – The challenges of being on your own as a business owner 05:22 – Why small businesses struggle & how lack of knowledge hurts them most 06:41 – Getting caught up in growth & forgetting to review your own numbers 07:51 – The value of CEO days & looking at your business health 08:49 – Why even bookkeepers shouldn't do their own books 10:17 – The difference between detail-oriented & problem-solving bookkeepers 12:22 – Knowing your strengths & weaknesses as an owner 15:38 – Lynn's hiring experiences & lessons learned in building a team 18:14 – How flexibility & trust created a loyal workforce 22:12 – The impact of culture on retention & business success

"But we just don't have the time if we're on the gerbil wheel of doing the same thing over and over again every month is just a new month. Where do I find time to ask three or even one new question when I'm busy doing the stuff that I have to do, and we've got to focus our attention on fewer clients, but deeper work for those clients. And that's when we create the capacity to do the kind of work that matters to those clients." -Geni Whitehouse In the finale of our two-part conversation with Geni Whitehouse, she shares practical tools and mindset shifts to help you step confidently into advisory and build stronger client relationships. In this interview, you'll learn.. Why mindset, not skill, holds most bookkeepers back from advisory How DISC behavior styles improve client communication Why listening is your secret superpower To learn more about Geni, click here. Connect with her on LinkedIn. Time Stamp 01:06 - Doing deeper work for fewer clients 03:00 - Using humor & storytelling 05:15 - DISC behavioral styles 08:18 - Listening as a key advisory skill 10:01 - Importance of aligning meeting style with client behavior 11:58 - Why Flexibility leads to more relevant outcomes for clients 14:57 - "Mindset, Toolset, Skillset" framework 15:40 - Mindset shift 17:56 - Focusing on fewer, higher-value clients 23:01 - Biggest mistake: not starting 25:50 - Prioritizing client impact over fear of failure 29:03 - Geni's websites and how to join her training programs

"Nobody knows what we're really doing, and so if we wanna increase the value of what we deliver, we've gotta break down those barriers to understanding and find ways to make the information meaningful and relevant to what they're trying to accomplish." -Geni Whitehouse In part one of a two-part series, Geni Whitehouse, founder of The Impactful Advisor, shares her journey from tax and tech to transforming how accountants and bookkeepers connect with clients. In this interview, you'll learn.. Why simple language builds stronger client connections The power of asking, 'Where do you go to see if your business is on track?' Shifting focus from showing expertise to empowering clients Plus much more! To learn more about Geni, click here. Connect with her on LinkedIn. Time Stamp 01:09 - Geni's journey from CPA to tech & training 02:48 - Realizes tax work didn't help clients the way she wanted 04:36 - Using humor to make accounting concepts clear & engaging 05:45 - Focusing on advisory, helping accountants ask better questions 06:04 - Advisory work with wineries — helping owners understand numbers 09:33 - Shift from proving knowledge to empowering clients 14:01 - Simple, clear language builds value 19:23 - Key question: "Where do you go to see if your business is on track?" 21:00 - SCOPE method to guide client conversations 24:42 - Find each client's true "why" to deliver real value 27:13 - Small changes (like one more bottle sold) can drive big impact