The Successful Bookkeeper Podcast

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

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

Sammy Mattingly and Fred Ott are back for the finale of their two-part conversation with host Michael Palmer. Where Part 1 covered the leap into bookkeeping entrepreneurship, Part 2 gets into the gritty, practical work of making a young firm sustainable — documenting processes, surviving the first real growth wave, hiring employee number one, and deciding what kind of business they actually want to build.

Chapters

[00:00] Introduction and Episode Recap

[01:18] What Makes This Partnership Work

[04:30] Growth Wave Exposes System Gaps

[07:00] Hiring the First Employee

[09:00] Fixing Onboarding the Right Way

[12:00] Joining Pure Bookkeeping and Freedom Gateway

[15:30] Walls Hit and Lessons Learned

[18:30] Long-Term Vision and the Journey

[21:30] The 'How to Make a Few Thousand Dollars' Podcast

The Partnership Advantage

One of the quieter themes running through this episode is just how much the partnership itself has been a growth tool. Sammy puts it plainly: "Fred is the only one of my friends that I could do this with — and it's mostly down to that accountability piece and the amount of work that each of us is going to put into this." For bookkeepers considering a partner arrangement, this episode is a useful reality check on what makes it work — shared drive, mutual trust, and complementary skill sets — and what makes it hard.

When Clients Arrive Faster Than Your Systems

The real test of any process is live clients. Sammy and Fred thought their systems were solid after months of heavy networking. Then the referrals started rolling in, and the cracks showed fast. "We quickly realized our systems and our processes are not what we need to be able to support the growth that we have now and that we want in the future," Fred says. Their response was to pull back from networking temporarily, sit down together, and map out standard operating procedures from scratch — building workflows, identifying automation opportunities, and stress-testing everything against real client volume.

Onboarding: Break It, Fix It, Repeat

Onboarding was the first thing to crack under pressure. Rather than patching it on the fly, Sammy and Fred blocked a Saturday, mapped every pain point, and rebuilt it. When the next wave of clients came through a month later, the process was smooth — but it surfaced a new set of smaller issues. "There's always something rolling onto the pocket of like, okay, here's an issue with our process," Sammy says. "Now we need to set aside time to work together to map out how to fix that and how to implement it." That cycle of deliberate improvement is now a permanent feature of how they run the business.

Pure Bookkeeping and the Freedom Gateway

Sammy credits early podcast listening for pointing him toward Pure Bookkeeping, and describes the decision to join as straightforward once the need for a real system became obvious. What stood out most was the access to experienced guidance: "Having an hour with Lisa Campbell a week, someone who's done it, who's built a very successful firm — she was great in just helping us learn and develop and how to work on the business." They also appreciated that the system is customizable — their Pure and Pixie setup reflects their firm, not a template.

Building Toward Something (Without Telling Everyone What It Is)

When Michael asks about the long-term vision, neither Sammy nor Fred throws out a revenue number — and Michael approves. Fred frames it well: "Like we want to grow and do all these things, but ultimately the day-to-day — we want the day-to-day to be enjoyable. We like challenging ourselves, we're curious people, and we like learning." They're also currently working through Traction by Gino Wickman and have launched their own podcast, How to Make a Few Thousand Dollars, which earned an early shoutout from the entrepreneur who inspired the name.

Links Mentioned

Mattingly & Ott Financial Accounting

How to Make a Few Thousand Dollars — Sammy and Fred's podcast (search on your podcast app)

Pure Bookkeeping — the system referenced throughout the episode

Traction by Gino Wickman — EOS framework book Sammy and Fred are currently implementing

How to Make a Few Billion Dollars by Brad Jacobs — inspiration for their podcast name

The Successful Bookkeeper Episode featuring Theresa Slack — referenced by Michael as a model partnership story

About the Guests

Fred Ott and Sammy Mattingly are co-founders of Mattingly & Ott Financial Accounting, LLC, a growing bookkeeping firm built on referral-driven networking, deliberate systems work, and a commitment to serving small business owners in their community. Friends since high school, they made the jump from W-2 employment to entrepreneurship together and are now navigating their first year of real scale — with their first employee, a growing client roster, and a podcast of their own.

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

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

Sammy Mattingly and Fred Ott co-founded Mattingly & Ott Financial Accounting in their mid-twenties, with backgrounds in Big Four auditing and investment management — and a brief, memorable detour into portable sanitation. In Part 1 of this two-part conversation, they walk through the early decisions that shaped their firm: getting certified, landing first clients, and discovering that digital ads were no substitute for showing up in person.

Chapters

[00:00] Cold open and intro

[01:18] Sammy's listener origin story

[03:15] Backgrounds before bookkeeping

[06:30] The porta potty adventure

[11:00] Finding bookkeeping on YouTube

[13:00] Five-week plan and first clients

[16:00] Why paid ads flopped

[18:30] Discovering networking as a strategy

[21:00] Building one-to-one meeting habits

[24:30] Shifting to strategic partnerships

From Porta Potties to ProAdvisor

Before bookkeeping, Sammy and Fred tried their hand at entrepreneurship the hard way — buying 20 used porta potties off a site called Crapper King, shipping them across the country on a semi-truck, and eventually moving them on Facebook Marketplace after a good pressure wash. The experience wasn't profitable, but it was formative. As Michael notes on the show, it gave them a layer of genuine empathy for clients: "They don't have all the answers, they're making mistakes, they're trying to figure it out." After a few more ideas, a YouTube video on starting a bookkeeping firm was all the spark Sammy needed. "I watched it, and I was like, well, if this guy can do it, Fred and I can do this."

The Five-Week Launch Plan

Once they committed to bookkeeping, Sammy and Fred moved fast. They built a five-week plan: get QuickBooks certified, become ProAdvisors, and land one client. Two large cleanup projects came through the QuickBooks ProAdvisor directory almost immediately — enough to justify going full-time. Fred describes those first weeks as equal parts doing the work and learning on the fly: "We were certified in QuickBooks, but it's like — we've got to figure out how this works. We've never done a QuickBooks cleanup for this type of company before."

Why Paid Ads Weren't the Answer

With their first projects underway, they turned to paid social media ads hoping to fill the pipeline. Six weeks and 15 or 16 leads later, the results were discouraging — contacts who were hard to reach and nowhere near ready to hire a bookkeeper. "We were finding they were all super unqualified," Fred says. That dead end turned out to be the pivot point. A conversation with a local small business attorney introduced a word they'd barely considered: networking.

Networking as a Growth Engine

Neither Sammy nor Fred would describe themselves as natural networkers — both lean introverted. But they committed fully, spending two to three months filling their days with open networking events and one-to-one coffee meetings. The accountability of working as a team made the difference: knowing the other person was putting in the effort kept each of them showing up. Fred's father, a career salesman, gave them the frame they needed: "Unseen, unheard, unsold." They tracked weekly one-to-one meeting goals, walked up to strangers, shook hands, and asked people to coffee — regardless of whether an obvious business connection was visible.

Strategic Relationships Over Volume

Over time, the approach evolved from broad networking to targeted relationship-building. Sammy describes the shift as following the data: "We took a step back and we were like, okay, what percentage of our referrals is coming from CPAs or whoever? And it's like, okay, well, if 80, 90% of our referrals are coming from these types of people, we need to go to rooms where there are these types of people." Tax preparers, business brokers, and other professionals who rarely attend networking events became the focus — making Mattingly & Ott's presence at those events even more valuable.

Links mentioned

Pure Bookkeeping — the system Sammy and Fred found through the podcast

Pixie — practice management tool they discovered through The Successful Bookkeeper

thesuccessfulbookkeeper.com — resources, episode search, and Ask the Show feature

About the guests

Sammy Mattingly and Fred Ott are co-founders of Mattingly & Ott Financial Accounting, LLC. High school friends turned business partners, they launched their bookkeeping firm roughly a year and a half ago and went full-time within the first few months. Sammy brings a background in Big Four audit; Fred comes from investment management. Together they serve small, service-based businesses and have built their client base almost entirely through in-person networking and strategic referral relationships. Part 2 of their conversation covers how those relationships translate into referral systems and scalable growth.

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

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

If you've ever quoted a price, panicked at the silence, and then talked yourself into a discount before the prospect even responded — this episode is for you. In the finale of this two-part series, Natalia Zacharin, Founder and Principal of Zacharin Consulting, picks up where she left off: taking a firm from underpriced and overworked to a multi-million-dollar operation built on confident pricing, high-caliber hires, and fractional CFO services that change businesses from the inside out.

Chapters

[00:00] Cold open and episode intro

[01:37] Non-negotiables and self-care

[04:48] The hiring formula and pricing shift

[08:00] Price it and zip it

[11:00] Joining a mastermind, betting on herself

[13:30] Building referrals and CFO services

[17:30] What fractional CFO work really looks like

[23:00] AI, pricing pressure, and quality

[26:30] Hiring up and scaling out of production

[29:00] Final advice and where to find Natalia

The Moment She Stopped Underselling

For a long time, Natalia was closing deals she immediately regretted. She'd set a minimum of $500 a month, get on the sales call, hit silence — and before the prospect could say a word, she'd already dropped the number. "I would get off the call and then be mad at myself because I did it again," she says. The fix was deceptively simple: state the price and stop talking. That uncomfortable pause exists for the client to process, ask questions, or push back — and it's not your job to fill it. Learning to sit in that silence was the turning point that finally gave her room to hire.

The Hiring Formula Behind the Growth

Natalia uses a straightforward formula: between $200,000 and $300,000 in gross revenue per employee. She was at $300,000 and wanted to hire — but the numbers said she needed to be closer to $500,000 first. So she raised her prices, created the margin, and then hired. Her early lesson: the first hire was underqualified, which meant she spent more time training than delegating. "Looking back, I should have hired someone with a lot more experience that was more expensive, maybe even a manager level." Hiring up — paying well, offering full benefits, building a team that can run without you — is the model she's stayed with ever since.

Fractional CFO Services: Already Doing It for Free

The expansion into fractional CFO work didn't start with a strategy — it started with Natalia noticing she was already answering CFO-level questions at the end of every bookkeeping sales call. Clients kept asking: how do I get more profitable? How much cash do I actually need? When should I hire? "If you're already giving advice, you're already doing that for free unless you're charging for it." She formalized those conversations into a monthly engagement built around projections, accountability, and the kind of honest focus that keeps business owners from avoiding the hard work that actually moves the needle.

AI, Pricing Pressure, and Leaning the Right Direction

With AI tools multiplying and overseas competitors undercutting on price, Natalia's response is deliberate: go the other direction. "Don't feel the pressure of constantly lowering your pricing. That's going in the wrong direction. You need to actually be even better." Her firm uses AI to work faster and more accurately, but every file is reviewed by an in-house controller regardless of client size. The value isn't in the tool — it's in the trained eye that knows where to look and what the numbers mean for that specific business.

Scaling Yourself Out of the Business

Getting out of day-to-day production takes longer than most people expect. Natalia spent four years trying to hand off payroll before she finally found a payroll-only specialist with decades of experience — not a generalist bookkeeper. The message for anyone building a firm: don't give up when a hire doesn't stick. Keep looking for the right person. "It took me four years to get out of payroll… I'd be on vacation, walking the beach, running someone's payroll on my phone because it kept coming back to me." The same patience applies to every role you want to transition out of.

Links Mentioned

Zacharin Consulting website: zacharynconsulting.com

LinkedIn: Grow Your Bottom Line

Instagram: Grow Your Bottom Line

Pure Bookkeeping: purebookkeeping.com

The Successful Bookkeeper resources: thesuccessfulbookkeeper.com

About the Guest

Natalia Zacharin is the Founder and Principal of Zacharin Consulting, a full-service bookkeeping and fractional CFO firm she built from the ground up as a single mother. Starting with cold LinkedIn outreach and clients at $75 a month, she scaled the firm to multi-million-dollar revenue by combining confident pricing, strategic hiring, and advisory services that help business owners understand and act on their numbers. She is based in the United States and serves clients across industries including logistics, IT, and professional services.

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

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

Natalia Zacharin had no bookkeeping background, no clients, and no safety net when she started Zacharin Consulting in January 2019. She was 49, a single mom, and her invoicing clerk job was being phased out. In part one of this two-part conversation, Natalia lays out exactly how she went from that starting point to building a firm that now employs 16 people, targets $4 million in revenue, and landed at number 802 on the 2025 Inc. 5000 list.

Chapters

[00:00] Cold open: asking the right questions

[00:52] Introducing Natalia Zacharin

[03:00] From invoicing clerk to business owner

[07:00] Where the firm stands today

[10:00] First client via LinkedIn

[13:00] Self-teaching bookkeeping on YouTube

[16:30] Hiring a CPA manager — lessons learned

[19:00] Building the pipeline: 4 clients to 12

[23:00] Doubling down and working 7 days a week

[26:00] COVID, the PPP pivot, and early burnout

Starting From Zero — And Meaning It

Natalia's entry into bookkeeping wasn't a career pivot she planned. Her fiancé suggested it over coffee when she couldn't find another job. She enrolled in an online course, started messaging business owners on LinkedIn in January 2019, and landed her first client on January 29th of that year — a landscaping company owner in California who is still a client today. Her prior experience as an invoicing clerk in Microsoft Dynamics and NetSuite gave her attention to detail, but she had never opened QuickBooks.

YouTube as a Training Program

When Natalia got into her first client's books, she found the revenue hadn't been recorded — showing a negative $2 million on the P&L. Rather than walking away, she cleaned it up herself using YouTube, watching videos second by second and refreshing the balance sheet after every change to see what happened. "That was how I learned," she says. "I taught myself how to read financials, not how to do just data entry." It was slow, it was self-directed, and it worked.

The Formula for Getting Clients Early On

Natalia built her first pipeline through two channels: LinkedIn outreach and a local women's business group. Her LinkedIn approach was simple — start genuine conversations, never lead with a pitch, and ask questions. "No one likes it when you just come out with a full three paragraphs of what you do. No one cares." At in-person events, she set a clear intention before walking in: she was there to get a client, not just to have lunch. By August 2019 she had 4 clients and quit her day job. By November she had 12 — enough to cover her bills.

Doubling Down on What Works

After quitting her job, Natalia worked 12 to 14 hours a day, seven days a week, iterating constantly on what was generating new business. Her core principle: if something moves the needle, do more of it faster. She avoided prescriptive networking formats like BNI in favour of methods she could control and test. "Selling is psychological, it's not intuitive," she says. "I just didn't give up. I didn't feel like I had other options, so I just kept going."

COVID, the PPP, and a Hard Lesson About Burnout

In January 2020, Natalia called her mother — who had been helping her financially — to say she no longer needed the support. Three months later, COVID hit and her clients' revenues collapsed. She pivoted immediately to helping clients apply for PPP and EIDL loans, achieving near-perfect approval and forgiveness rates. But by August 2020, working alone under enormous pressure, she stopped exercising and started running out of energy. Part two of this series picks up there — with hard-won lessons on burnout, pricing, and scaling a team.

Links Mentioned

Zacharin Consulting: zacharinconsulting.com

Pure Bookkeeping: purebookkeeping.com

The Successful Bookkeeper: thesuccessfulbookkeeper.com

About the Guest

Natalia Zacharin is the Founder and Principal of Zacharin Consulting, a full-service accounting firm based in Maryland that offers bookkeeping, accounting, and fractional CFO services. She started the firm in 2019 with no formal bookkeeping training and grew it to a 16-person team tracking over $3 million in annual revenue. In 2025, Zacharin Consulting was named to the Inc. 5000 list of fastest-growing companies in the United States, ranking number 802.

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