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Your QuickBooks Is Smarter Than You Think (And Getting Smarter Every Day)

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When you can upload a photo of a bank statement and watch QuickBooks turn it into perfectly categorized transactions, you know something big is happening in the accounting world. The tedious work that once took hours is disappearing, replaced by something far more valuable: actual business insights.

In episode 114 of The Unofficial QuickBooks Accountants Podcast, titled “Those Sneaky AI Agents,” hosts Alicia Katz Pollock and Dan DeLong explore the seven AI agents that Intuit built into QuickBooks Online. After testing these tools extensively, they conclude it’s “90% AI and 10% marketing,” a ratio that should interest any accounting professional wondering if these changes matter.

The Seven AI Agents

Intuit rolled out seven different AI agents across QuickBooks: accounting, payments, customer, finance, project management, analytics, and payroll. As Alicia explains, “All of this is not even version 1.0. It’s kind of version 0.5 at this point.” Some features are in beta, others depend on which QuickBooks version you use, and a few you might not see unless you’re using specific features like projects or payroll.

But these agents are turning QuickBooks from a recording system into something that actually helps you make decisions. “What they’re trying to do,” Alicia notes, “is take the data, make it actionable, and give us insight into what’s happening in the business so we can actually take action on it.”

The Accounting Agent: Your New Data Entry Partner

The accounting agent has completely redesigned how bank feeds work. While teaching a three-hour class on the new features, Alicia made a surprising discovery. “All the things I was taking out were all of the gotchas and the troubleshooting.” Problems that plagued users for years, like dealing with duplicate transfer rules, simply don’t exist anymore.

The new banking interface features inline editable fields, meaning you can categorize transactions without constantly clicking into detailed views. Yes, it looks more cluttered at first, especially on smaller monitors. But there’s a fix: hit Control+Period (or Command+Period on Mac) to activate Zen mode, which folds away the sidebar and gives you full screen for your banking work.

The AI now explains why it’s suggesting certain categorizations. As Alicia describes it, “This is why you are off base, or oh, this is why that actually makes sense.” The downside is you have to retrain the AI from scratch. The good news is it learns fast—usually after seeing each transaction type once for monthly items, or three times for quarterly ones.

The Game-Changing PDF Upload

Here’s where things get really interesting. If your bank doesn’t connect to QuickBooks, you no longer need to wrestle with CSV files. Just drag in a PDF, JPEG, or PNG of your statement—even a photo from your phone works. The AI scrapes the document and creates a functioning bank feed with all the categorization benefits of a direct connection.

There are limits. Statements with both checking and savings accounts on the same page won’t work (though you could split them with a PDF editor). Complex statements get sent to human reviewers who typically respond within two hours, and they use your statement to improve the system for everyone.

Collaboration Without Meetings

The new collaboration feature adds a speech bubble icon to each transaction. Click it to ask questions, request documentation, or explain unusual expenses, all without scheduling a meeting. One of Alicia’s clients who previously met monthly with her bookkeeper immediately saw the value. “She is really excited to not necessarily have to meet in real time.”

The “Ready to Post” feature finds the sweet spot between automation and control. Instead of auto-adding transactions, it identifies high-confidence categorizations and presents them in a bubble at the top of your feed. As Alicia explains, “These are the transactions that we are pretty darn sure we got right.” Review them all and accept them with just two clicks.

Smarter Reconciliation and Problem Detection

The new reconciliation screen looks complex at first, but it’s actually brilliant. Upload your bank statement, and QuickBooks shows you exactly where problems hide. Not just “you’re off by $150,” but whether the difference is in deposits or payments.

Each transaction now has two rows: one showing what the statement says, another showing what QuickBooks says. Colored badges instantly communicate status. Green means matched. Blue means it’s in QuickBooks but not on your statement. Orange flags special situations like voided transactions.

The anomaly detection feature takes this further. Blue sparkles appear on reports when something breaks from normal patterns. Alicia describes her old process: “I’ve always had to run a P&L by month and physically scan all of the numbers and then drill in to go see, well, why is this one higher than usual?” Now the AI simply tells her: “You have this extra transaction for five times as much as usual.”

The Payments and Customer Agents: Growing Your Business

The payments agent analyzes your invoice history to surface potential issues. When Alicia’s system revealed “84% of your invoices last year were paid late, or not at all,” it immediately suggested adding a 2% late fee and provided the setup right there.

For each customer, it tracks payment patterns individually. Do they always pay three days late? Twenty days late? This insight helps you make smart decisions about payment terms and follow-up strategies.

The Customer Hub (currently in beta) adds full CRM capabilities to QuickBooks. It can scan your Gmail or Outlook for business conversations and turn them into leads. Track prospects through your pipeline from inquiry to close. But the real magic happens after the sale.

The system can send automatic feedback surveys after invoice payment. Happy customers (4-5 stars) get asked when they want to work together again and if they know anyone who needs similar services. These responses appear as work requests and warm referrals in your Customer Hub. As Alicia emphasizes: “That’s new business. That is money in your pocket.”

Evolution, Not Replacement

These AI agents aren’t replacing accountants; they’re freeing us from tedious work to focus on what matters. As Dan notes about modern business, “If you’re waiting for a quarterly report to be done three months ago to make a decision these days, that’s just not fast enough.”

The key is Dan’s “trust but verify” approach. The AI excels at pattern recognition but needs human judgment for context. When his payments agent incorrectly suggested late fees for on-time payments, human insight caught what the AI missed.

Alicia’s advice? Start clicking those blue sparkles. Give feedback with the thumbs up and thumbs down buttons. Don’t just dismiss features because they’re in your way; actually evaluate if they’re helpful. As she puts it, “Thumbs down is ‘No, this thing is not accurate and it’s not helpful,’ not ‘I don’t want to look at it right now.'”

Ready to see these “sneaky AI agents” in action? Listen to the full episode where Alicia and Dan demonstrate each feature, share implementation strategies, and explain exactly which upgrades might be worth it for your practice. The future of accounting is here, right in your QuickBooks account.

Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT!

Deloitte’s $440,000 AI Fabrication Scandal Exposes the Accounting Profession’s Deepest Fears

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A startup founder discovered $2.1 million in embezzlement by his co-founder in just 18 minutes using Claude AI. The company’s internal auditors, external auditors, and even the CFO had completely missed it. Meanwhile, Deloitte was forced to refund the Australian government hundreds of thousands of dollars after delivering a report filled with AI-generated fabrications.

In this episode of The Accounting Podcast, hosts Blake Oliver and David Leary dig into these stories. They explore how AI is both exposing massive frauds and creating embarrassing failures, examine the chaos from the government shutdown, and question whether traditional accounting services still matter when 86% of major companies use broken charts that nobody even notices.

When AI Catches What Humans Miss (And Creates What Shouldn’t Exist)

The accounting profession is experiencing an AI identity crisis. On one hand, artificial intelligence can spot complex fraud that teams of professionals completely miss. On the other hand, professionals are using it to generate work that looks legitimate but is actually riddled with fabrications.

Let’s start with Deloitte’s spectacular failure. The Big Four firm charged the Australian government $440,000 AUD (about $290,000 USD) for a 237-page report on welfare compliance systems. The problem? It contained over 20 AI-generated errors, including completely made-up quotes from federal court judgments and references to non-existent academic papers.

Chris Rudge, a Sydney University researcher, spotted the errors immediately. One fabrication attributed a non-existent book to constitutional law professor Lisa Burton Crawford on a topic completely outside her field. “I instantaneously knew it was either hallucinated by AI or the world’s best kept secret because I’d never heard of the book, and it sounded preposterous,” Rudge said.

Even after getting caught, Deloitte insisted its findings and recommendations were still valid. This prompted Australian Labor Senator Deborah O’Neill to observe that Deloitte has “a human intelligence problem.”

But here’s where it gets interesting. While Deloitte was using AI to create fake references, a startup founder used it to uncover real fraud. He exported his company’s QuickBooks data into Claude AI and asked one simple question: “What’s wrong with this picture?”

In just 18 minutes, the AI found what everyone else had missed: 17 fake companies routing $2.1 million to his co-founder’s personal accounts through shell companies. The AI spotted patterns humans overlooked, including fake vendors paid on 23-day cycles while real vendors were paid on 28-day cycles, and payment amounts that followed Fibonacci sequences, which humans subconsciously create when making up numbers.

The founder has since turned this into a business, selling AI-powered fraud detection prompts for $10,000 each to 47 clients. He’s probably making more money from his fraud-detection business than from his original startup.

As Leary points out, this creates both an opportunity and a threat for accounting firms. “The real risk of AI taking accounting jobs isn’t that AI will take the job away. Clients are just going to say, ‘I can do that myself. I don’t need to pay somebody $400,000 to do a half-assed ChatGPT thing.’”

Government Shutdown: When Critical Systems Break Down

The conversation then turned to the government shutdown’s impact on air travel and tax services. The situation has become genuinely dangerous, with cascading failures that reveal how fragile our systems really are.

Air traffic controller-related delays jumped from a typical 5% to 53% as workers called in sick rather than work without pay. Oliver experienced this firsthand when his flight was delayed for hours with no official explanation, though flight attendants privately blamed air traffic control shortages.

The scariest incident happened at Burbank Airport in Los Angeles, where the tower went completely unmanned. “When that happens, there is a backup procedure, which is that the pilots have to do their own air traffic control,” Oliver explains. “They get on a shared frequency and have to communicate with each other. There’s no intermediary. So that not only slows things down. It also creates risk. There’s a huge risk of these planes crashing into each other because they miscommunicate.”

The economic impact is staggering. The US Travel Association estimates $1 billion in weekly losses to the travel economy. Over 750,000 federal workers have been furloughed, while more than a million work without pay. For TSA screeners earning an average of $51,000, the situation is untenable. “If they don’t get paid, they are not paying their bills,” Oliver notes. “They’re going to go drive for Uber to pay the bills.”

The IRS shutdown creates serious problems for accountants. Nearly half of IRS staff have been furloughed. While electronic returns continue processing and automated refunds still flow, human support has collapsed. Phone support is essentially gone, paper returns sit unprocessed, and audits have stopped. Yet interest and penalties continue to accrue, and all deadlines remain in effect.

Adding to the chaos, Trump fired over 4,100 federal workers instead of furloughing them. The Treasury alone lost 1,446 employees, including about 1,300 IRS workers. “It’s the first time in modern history that mass firings have happened during a funding lapse,” Oliver observes.

The administration also created a new “CEO of the IRS” position to bypass Senate confirmation, appointing Frank Bisignano, former CEO of Fiserv, who still owns about $300 million in company stock. This creates obvious conflicts of interest, especially since Fiserv is involved in launching digital stablecoin initiatives. “This is why you have to have hearings. You can’t just appoint somebody to a position,” Leary emphasizes.

When Independence Becomes a Joke

Next, Oliver and Leary discussed how financial entanglements are destroying audit independence while regulators focus on trivial violations.

Take BDO’s current crisis as an example. The firm took a $1.3 billion loan at approximately 9% interest from Apollo Global Management to finance its employee stock ownership plan. The debt forced the company to lay off employees, freeze travel, and conduct emergency cost reviews across all divisions.

But while BDO was giving First Brands a clean audit opinion, Apollo was actively shorting the company. First Brands collapsed months after BDO’s clean audit. “If I’m BDO and I audit a company that is being shorted by a company I took a $1 billion loan from, where’s the independence?” Leary asks. “What is the fraud triangle? Opportunity, rationalization, and financial pressure. All the parts of the fraud triangle are here.”

Meanwhile, EY is celebrating a “dramatic audit quality turnaround,” with its deficiency rate dropping from 46% in 2022 to below 10% in 2025. They achieved this miracle by firing 132 public company audit clients. In other words, the problematic audits didn’t disappear. They just moved to Deloitte and KPMG. “Have we actually achieved anything here? Or have we just shifted the bad audits somewhere else?” Oliver wonders.

The hosts also discussed a new scheme where crypto promoters target CPA firm clients. The Truevestment Bitcoin Legacy Fund wants CPAs to help raise $150 million from their clients, which institutional investors will then match before merging into a Nasdaq entity—essentially a SPAC wrapped in Bitcoin speculation.

The marketing compares buying Bitcoin today to “buying the Dow at 900.” But as Leary points out, when the Dow was at 900 in the mid-1960s, it consisted of companies like AT&T and General Electric—”companies that made things” and created real value, not speculation.

Why Nobody Cares About Financial Reports Anymore

Perhaps the most damning revelation from the podcast’s recent news roundup is that 86% of major companies are using broken charts in their financial reports. A CPA Journal study found bar charts with misleading axes, pie slices that don’t match percentages, and deliberate distortions to exaggerate performance. Of 1,584 charts reviewed, 12% had fatal flaws that completely misrepresented the data.

“The fact that so many of them have errors and nobody’s pointing them out indicates to me that nobody’s reading them,” Oliver observes. Indeed, 10-K filings get downloaded an average of just a few dozen times.

The hosts even shared a bizarre example where social media bots criticizing Cracker Barrel’s new logo caused the stock price to tank. According to Wall Street Journal data, 44.5% of posts about the logo change were from bots. “Maybe nobody cares about your charts because nobody even cares about the financial statements,” Leary suggests.

What This Means for Your Firm

The key insight from Hector Garcia stuck with David: “AI is never going to do perfect accounting, but it’s going to do it good enough.” For most clients, “good enough” financials that they can generate themselves might be perfectly adequate.

Accounting professionals can embrace AI for meaningful fraud detection and insights, or watch clients realize they can generate “good enough” work themselves. As this episode of The Accounting Podcast makes clear, the traditional value proposition of professional accounting services is crumbling. The firms that survive will be those that identify and deliver human value that transcends what AI can do: strategic insight, ethical judgment, and genuine expertise that no algorithm can replicate.

Listen to this episode to understand not just the challenges facing accounting, but what you need to do differently starting today.

The IRS Can Hit Your Clients With Criminal Charges for Bad Bookkeeping (And Most Tax Pros Don’t Know It)

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If you’ve ever received a shoebox full of receipts from a client or struggled with QuickBooks files where half the expenses are labeled “miscellaneous,” you know the frustration. But according to Jeremy Wells, EA, CPA, in this episode of Tax in Action, poor recordkeeping isn’t just a workflow problem. It’s a legal violation that could cost your clients thousands in penalties.

Most tax professionals treat recordkeeping like a suggestion. But it’s actually a federal requirement with serious consequences, including a 20% penalty on underpaid taxes and even potential criminal charges. Understanding these requirements can transform your practice and create new revenue opportunities.

Your clients are breaking the law (and they don’t know it)

Wells starts with a section of the tax code that most practitioners overlook. IRC Section 6001 doesn’t suggest or recommend. It requires taxpayers to “keep such records, render such statements, make such returns, and comply with such rules and regulations as the Secretary may from time to time provide.”

The Treasury regulations spell it out even more clearly. Taxpayers must keep “permanent books of account or records, including inventories, as are sufficient to establish the amount of gross income, deductions, credits, or other matters required to be shown by such person in any return.”

“The way I read this,” Wells explains, “you as a taxpayer, in order to file a tax return, need to have permanent books and records you can rely on in order to justify and substantiate any amount of gross income, deductions, credits, or anything else that you’re putting into that return.”

Here’s what catches many people off guard: tax returns themselves don’t prove anything. In Wienke v. Commissioner (T.C. Memo 2020-143), the Tax Court established that returns are “merely statements of claims and are not considered evidence of the claims themselves.” The real evidence must come from the taxpayer’s books and records. So when your client thinks their signed tax return proves their income to a lender, they’re wrong. Without proper records backing it up, that return is just a piece of paper with numbers on it.

The penalties for inadequate recordkeeping can devastate a small business. Section 6662 imposes a 20% accuracy-related penalty on any underpayment due to negligence, which specifically includes “any failure by the taxpayer to keep adequate books and records, or to substantiate items properly.” That’s 20% on top of the taxes owed, plus interest.

But it gets worse. Section 7203 makes willful failure to keep records a criminal offense. The penalties are up to $25,000 for individuals or $100,000 for corporations, plus up to a year in prison. While Wells notes that your typical shoebox client probably won’t face jail time, the existence of criminal penalties shows how seriously the IRS takes recordkeeping requirements.

The three warning signs every practitioner must recognize

These requirements create ethical obligations for practitioners too. Circular 230, Section 10.34(d) allows you to rely on client information, but requires “reasonable inquiries if the information as furnished appears to be incorrect, inconsistent with an important fact or another factual assumption, or incomplete.”

Wells calls these the “three I’s” that should trigger immediate concern. He shares a common example: “When I ask them what their business mileage is, they’ll just tell me a flat number that has three or four zeros at the end of it. As soon as I see that information, I already know, just in my gut looking at that information, whether it appears to be incorrect, inconsistent, or incomplete.”

When you spot these red flags, you can’t just ignore them. Wells describes the uncomfortable conversation that follows when he asks for a mileage log. “Nine times out of ten, they’re going to tell me they didn’t actually keep up with one.” At that point, you face a tough choice. Do you push harder for documentation, accept questionable information, or potentially end the client relationship?

“It might be a tough decision to stop working with a taxpayer because they want to claim a certain amount of miles,” Wells acknowledges. But when clients repeatedly ignore recordkeeping requirements despite annual reminders, “at that point, we might have to reconsider the relationship.”

How good records flip the script on IRS audits

While penalties provide the stick, there’s also a powerful carrot for maintaining proper records. Wells reveals how good recordkeeping can completely change the dynamics of an IRS dispute.

Normally, the IRS holds all the cards. The Supreme Court established in Welch v. Helvering (1933) that “the commissioner’s determinations have a presumption of correctness while the taxpayer bears the burden of proving the IRS position wrong.” Wells calls this “a tough hill to climb, especially for a taxpayer that has not kept good books and records.”

But IRC Section 7491 flips this burden. When taxpayers introduce credible evidence, comply with substantiation requirements, and maintain proper records, the burden shifts to the IRS to prove the taxpayer wrong.

“If a taxpayer shows up to an examination or an audit with good books and records,” Wells explains, “then the auditor knows that under Section 7491, now it’s on the IRS to prove the taxpayer is wrong.”

This creates “a more positive settlement climate,” according to a 2003 Tax Notes article Wells cites. Auditors become more willing to negotiate reasonable settlements rather than risk losing in court. He notes that even when a taxpayer takes a “technically incorrect position,” having good records to explain their reasoning can lead to much better outcomes.

Why the Cohan Rule won’t save your clients

Many practitioners rely on the Cohan Rule as a safety net, but Wells warns it’s been dangerously misunderstood. This 1930 court decision allows taxpayers to deduct “a reasonable estimate of the amount of a verifiable trade or business expense if the exact figure is unavailable.”

“I’ve heard, between bad tax advice on social media and some practitioners who haven’t really read the court case,” Wells says, people claiming “if the client doesn’t know how much, we’ll just fill in a number and appeal to the Cohan rule.” But that’s not how it works.

Courts take a harsh view of taxpayers trying to use Cohan without basis. In Barrios v. Commissioner (2023), the court stated it “bears heavily against the taxpayer who failed to more precisely substantiate the expense.” Translation: courts will slash your estimates, sometimes to zero.

Wells cites Williams v. US (1957), where the court refused to “guess” at expenses, calling relief without evidence “unguided largesse.” The message is clear: you need some reasonable basis for any estimate, not just a number that feels right.

Making matters worse, Section 274 completely blocks the Cohan Rule for certain expenses:

  • Travel
  • Entertainment
  • Business gifts
  • Listed property (especially vehicles)

For these categories, taxpayers must keep contemporaneous logs showing time, place, amount, and business purpose. Wells emphasizes how strict this is: “There have been tax court and federal court cases where the mileage log was simply thrown out and no deductions were allowed because the taxpayer attempted to recreate that log after the fact.”

Turn recordkeeping problems into profitable services

Instead of fighting poor recordkeeping every tax season, Wells outlines specific services that transform this challenge into recurring revenue.

His foundation is a “bookkeeping review service.” You’re not doing actual bookkeeping. Instead, you review the client’s records quarterly and flag issues. “We’re probably not going to look through a lot of five, ten, twenty dollar office expenses,” Wells explains. “But we might look through some expenses that are four or five, six figures.”

During these reviews, you might spot expenses that should be capitalized instead of deducted, deposits miscategorized as revenue when they’re actually loans, or aging receivables signaling cash flow problems. The key is efficiency. “They don’t take nearly as much time as actual bookkeeping does,” Wells points out.

He also strongly advocates for direct communication with clients’ bookkeepers, eliminating the game of telephone that wastes everyone’s time. Set up quarterly check-ins to discuss categorization questions, journal entries, and ownership changes before they become tax-time emergencies.

“This should not be free,” Wells stresses. “This should not be just included. You should not just start doing this out of the goodness of your heart.” Whether bundled into tax prep fees or structured as a monthly subscription, these services must generate revenue.

Some practitioners take this even further with preferred partner networks. Wells knows firm owners who refuse to prepare returns unless the books come from their vetted bookkeepers. While it sounds extreme, the benefits are clear. “They’re never going to have to worry about whether a deposit was really revenue or contribution of equity or new line of credit, because they trust the bookkeeper to have taken care of that already.”

For maximum scalability, Wells suggests creating educational resources. Use screen recording tools to solve common problems once, then share those videos with multiple clients. “Each time a client asks you a question, you know others have that same question,” he notes. This transforms repetitive education from a time drain into a reusable asset.

Listen to transform your practice

Recordkeeping isn’t optional; it’s legally required, with penalties ranging from 20% of underpaid taxes to potential criminal charges. But understanding this framework doesn’t just protect you and your clients from disasters. It opens doors to shift audit dynamics in your favor, negotiate better settlements, and create profitable advisory services.

Will you keep wrestling with shoeboxes every tax season, hoping estimates will pass muster? Or build systematic solutions that generate recurring revenue while protecting everyone involved?

Listen to the full episode to learn exactly how to implement these strategies in your practice. Because when you understand the legal framework—the requirements, the penalties, and most importantly, the opportunities—you stop just surviving busy season and start building a practice that thrives year-round.

Smart Accounting Firms Are Done Being Yes People

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Picture an  accounting firm that keeps partner salaries locked away like state secrets. Staff spend years wondering what partnership actually pays. Meanwhile, another firm down the street posts everyone’s salary on a public leaderboard. The path to partnership comes with clear milestones and transparent rewards.

This stark difference shows just one way “renegade” firms are shaking up the accounting profession.

In episode 104 of the Earmark Podcast, recorded live during the Advisory Amplified tour in Austin, host Blake Oliver digs into what it means to be a “renegade” in accounting. He’s joined by Madeline Reeves, founder and CEO of Fearless Foundry, and Wesley McDonald, go-to-market leader at Relay. Together, they explore how forward-thinking firms and tech companies challenge everything we thought we knew about running an accounting practice.

What Makes a Firm “Renegade”?

So what exactly is a renegade firm? Reeves has worked with many of them, and she has a clear answer.

“A renegade firm is leading their clients to somewhere new and is not settling for the ways things have always been done,” she explains. These firms challenge the status quo. They see tech companies as partners, not just vendors. And they push their clients and technology partners to do better.

These firms also stand out in unexpected ways. Take Lance CPA (now part of Revel CPA). When they signed new clients in the brewery and hospitality space, they didn’t just send a standard engagement letter. They delivered beautiful welcome kits complete with custom beer glasses and cool socks. It was their way of saying this isn’t your typical accounting relationship.

But being a renegade goes deeper than nice gestures. These firms also excel at saying no.

“A lot of firms are dedicated to being acts-of-service people,” Reeves notes. “They become a little bit of “yes people” or people pleasers. But the real renegade firms are like, ‘I do not do that service or I do not work with that industry.’”

They’re not trying to be everything to everyone. They focus on being exceptional at what they do best.

Taking the Lead with Clients

Traditional firms often let clients call the shots. They use whatever software the client prefers. They adapt to the client’s processes. They follow rather than lead.

Renegade firms flip this completely around.

Reeves puts it perfectly: “When I go to the dentist, I’m not telling the dentist, ‘No, don’t use that drill in my mouth.’ I don’t know how to do dentistry. So if you’re an accountant, it’s your job to lead your clients.”

These firms come to the table saying, “This is how we do this job well and effectively for you. If the goal is advisory services, this is how we get there better, faster.”

When you’re the professional, you set the standards for how the work gets done.

Breaking Open the Black Box of Compensation

One radical change happening in renegade firms involves money—specifically, who knows what about everyone’s pay.

“On the most successful sales teams I’ve been a part of, there’s a leaderboard that shows exactly how much people have attained in their salary in that quarter,” McDonald shares. “Which is a wild concept to think about in some industries.”

Oliver points out the obvious problem with traditional secrecy: “One of the biggest secrets is how much the partners make. But if we want everybody to want to be a partner, why don’t we tell them?”

It’s not just about knowing the numbers, though. Reeves emphasizes that firms need “not just pay transparency but pathway transparency.” People need to see the clear steps to advancement, not just the end goal.

McDonald, drawing from his tech experience, says promotions shouldn’t be about time in seat. “You’re ready to move to the next level as soon as you’re performing at that level.”

This represents a huge shift from the traditional model where you might wait five years for a promotion regardless of your performance.

Building Teams That Actually Want to Work Together

The old model pits high performers against each other. Remember those weekly emails showing who billed the most hours? Competition is the traditional way to drive performance.

Renegade firms take a different approach.

“If you have people on your team who think the only way up is their own performance, your whole team is going to be fighting against each other,” Reeves explains. She learned this building sales teams. When she tied part of compensation to team performance, not just individual metrics, “We saw performance double because people were suddenly willing to turn to the teammate next to them and show them what was working.”

This collaborative approach is essential for attracting younger professionals. As Reeves notes, “There are a lot of young people who are coming out of school, and there’s nothing exciting to them about working 90 hours a week during tax season. They’re like, ‘hard pass.’”

“You can tell people to do the work and you can pay people to do the work,” Reeves says. “But to actually get people to want to show up and fully do the work, it has to align around the things that genuinely motivate them as a human.”

When Banking Becomes a Partnership

Banking isn’t usually seen as innovative. But companies like Relay are changing that, starting with how they work with accountants.

Most people choose banks for passive reasons. “It’s because I know that bank exists or they’re down the street or my parents bank there,” McDonald observes.

But what if your bank actually worked for you and your accountant?

“Relay is purpose built for our accounting partners and their clients,” McDonald explains. Traditional banks gatekeep information. Relay surfaces it to accountants so they can actually help their clients.

The difference is stark. “I’m not even sure how I would give feedback to Chase or Bank of America or Wells Fargo,” Oliver admits. In contrast, McDonald says, “If a partner of ours has an idea and they bring it to us, we will act on that idea.”

This isn’t just talk. Being a champion for SMEs and their partners is one of Relay’s seven core values. They were the first banking platform to go to market specifically through accounting professionals.

Reeves shares her own frustration with traditional banking. She wanted to support a local community bank that shared her values. But they had no online banking. Getting statements required writing emails to a banker.

“If you’re really serving small business at the core of who you are,” she says, “making me have to email a banker to get a bank statement isn’t serving small business. That’s creating extra manual work for me or for my accountant.”

Learning from Renegade Mistakes

Being a renegade means trying new things. And that means making mistakes.

Reeves shares a particularly painful one. She built what she thought was an innovative compensation model, paying top performers a percentage of deals they closed. Then she discovered a senior employee was committing fraud, jacking up prices in their proposal system to increase her cut.

Reeves recalls discovering the fraud just before a major conference and having to lock down all her banking immediately. The experience taught her to “trust but verify.” You need systems to ensure people act the right way, even those you trust.

McDonald shares his own revelation about breaking from the traditional path. He started his career as a fixed income broker. But as he earned promotions, he looked around and realized, “everyone there had been doing it for 30 years. I thought, ‘Can I do this for 25 more years?’”

He chose the non-linear path instead, moving between sales, consulting, and building teams. “I had stopped my learning journey,” he reflects. “I want to be a lifelong learner.”

Oliver’s “mistake” was majoring in music at the most expensive university in the country. But the experience taught him how to teach himself anything—a skill that proved invaluable in accounting. “If you can sit in a practice room for six hours a day and learn how to play a concerto, that’s all just breaking problems down into literally measure by measure, note by note.”

The Path Forward

The renegade firms discussed in this episode aren’t making small tweaks to the traditional model. They’re rebuilding it from scratch.

They’re becoming strategic leaders who guide rather than follow clients, creating transparent cultures where collaboration beats competition, and embracing technology companies as true partners rather than necessary evils.

With younger professionals rejecting traditional firm culture and clients demanding strategic guidance over compliance work, the old model is dying. The renegade approach offers a sustainable alternative that actually addresses why people leave accounting.

These innovations are happening right now at thriving firms. From brewery-themed welcome kits to banking platforms built for accountant collaboration, these changes prove accounting firms can create experiences that rival any modern service business.

Want to hear the complete conversation? Listen to the full episode. You’ll get the full story of how Reeves uncovered fraud through her proposal system, Olivers’s journey from professional musician to accounting innovator, and detailed strategies for implementing renegade principles in your own firm.

The Accounting Platform That Achieves 96.5% Automation Reveals How They Did It

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“No one’s going to be outcompeted by the AI itself. You are going to be outcompeted by firms that really adopt this aggressively,” warns Jeff Seibert, whose company just hit 96.5% accuracy in automated bookkeeping—something that seemed impossible just a few years ago.

In this milestone 100th episode of the Earmark Podcast, Blake Oliver sits down with Jeff Seibert, co-founder and CEO of Digits, to explore how AI is fundamentally changing the architecture of accounting software. Seibert brings fresh eyes to accounting—he previously led consumer product at Twitter and built Crashlytics (now running on six billion smartphones). His frustration was simple: Why could product teams access real-time analytics while business owners waited weeks for black-and-white spreadsheets?

Founded in 2018, Digits set out to reimagine accounting in the age of machine learning. While traditional software treats transactions as meaningless text in rigid databases, Digits achieves near-perfect automation by treating financial data as interconnected objects that learn from patterns across millions of transactions.

The 30-Year-Old Problem Holding Back Accounting

As Seibert sees it, the fundamental issue facing bookkeeping automation is that every major accounting platform—QuickBooks, Xero, and even NetSuite—runs on relational databases designed 20-30 years ago. These systems treat transactions as simple text entries with no understanding of what they mean.

“QuickBooks is just going to see an Uber transaction as “U-b-e-r”. It just sees text,” Seibert explains. “It doesn’t understand the data, it doesn’t know what Uber actually is.”

This limitation explains why Intuit, with all its resources, has yet to deliver meaningful automation. The answer is architectural. Each QuickBooks company exists in its own isolated database, preventing the software from learning patterns across businesses. The constraints run so deep that QuickBooks still can’t handle having a vendor and customer with the same name—it appears they chose “name” as the primary database key decades ago.

Digits takes a completely different approach using what’s called a vector graph data model. Everything becomes an object—Uber is an object, your expense categories are objects, your bank accounts are objects. Transactions become connections between these objects, creating a web of financial relationships the AI can understand.

This mirrors how large language models (LLMs) work, converting transactions into vector embeddings, essentially plotting them in multi-dimensional space where similar items cluster together. When trained on 170 million transactions representing nearly $1 trillion in business activity, patterns emerge that would be obvious to humans but invisible to traditional software.

“When you have that scale of data and you see how everyone has booked Uber before, you start to see patterns,” Seibert notes. “The model starts learning. If it sees Lyft in your accounting for this client, it then knows how to book Uber.”

How AI Agents Actually Work (Hint: Like Clever Interns)

The accounting world is buzzing about “AI agents,” but what are they really? Seibert explains, “An agent is simply an LLM that you run in a loop. You give it a task, it attempts the task, you ask if it completed it. If not, it continues until it’s done.”

Think of them as clever interns who never get tired. Digits has been running these agents in production since January 2024, primarily for researching unfamiliar transactions.

The system uses three layers of intelligence. First, it checks if this specific client has seen this transaction before. If yes, it books the transaction exactly the same way. Second, if the transaction is new to this client but familiar to the platform, it uses its global model trained across all users. Third, for completely novel transactions, the agent literally Googles them.

“What would you do as an accountant? You would probably Google it,” Seibert explains. “What do our agents do? They literally Google it, research the transaction, build a dossier about it.”

As a result, only 4-5% of transactions now require human review, compared to the 20% that typically slip through even well-maintained rule-based systems. Notably, the system maintains strict confidence thresholds. Any transaction it is unsure about gets flagged for human review. It never guesses when uncertain.

The upcoming reconciliation feature shows how sophisticated these agents have become. The system pulls statements directly from banks or extracts them from PDFs, then matches transactions with pixel-level precision. “You can literally click on the transaction and see it on the statement and vice versa,” Seibert says. This builds trust with accountants who need to see exactly where the numbers come from.

What This Means for Your Firm’s Future

As of August, Digits hit 96.5% accuracy, up from 93.5% in spring. Each percentage point represents thousands of transactions that no longer need human touch. But it begs the question: how do you price services when the work happens automatically?

“If you’re charging purely per hour right now, then automation may make that challenging,” Seibert acknowledges. But forward-thinking firms are already adapting. They’re moving to fixed-fee models for routine work like monthly closes, which become increasingly profitable as automation reduces time investment. Many use a hybrid approach, charging fixed fees for the close, and hourly rates for advisory work.

At a flat $100 per month (with volume discounts for accounting partners), Digits offers predictable pricing that contrasts sharply with QuickBooks’ constant increases. The platform even offers specialized SKUs for ledger-only or reporting-only clients, accommodating diverse practice needs.

The staffing implications are real but not apocalyptic. Junior bookkeeping roles focused on data entry will diminish. But Seibert points out this could make the profession more attractive: “You don’t want to just sit there doing data entry all day long. You want to learn how to advise businesses.”

Seibert recommends firms start small when implementing automated bookkeeping. “Pick one client in your firm and see what you can achieve,” Seibert challenges. Choose a simple, digital-native business like consultants, SaaS companies, or agencies with predictable electronic expenses. Build confidence, then expand to complex cases.

Building Trust Through Transparency

With financial data flowing through AI systems, security is crucial. Digits addresses this with architecture developed at Seibert’s previous companies, where they handled crash data from billions of smartphones.

Everything stays within Digits’ systems; they don’t send raw data to OpenAI or other third parties. All data is encrypted at rest using per-object envelope encryption, where each object has its own encryption key. Even if breached, stealing one key wouldn’t compromise the system.

The platform is SOC 2 Type 2 certified, with complete audit trails showing who changed what and when. You can even grant granular access, like giving your marketing manager visibility into only marketing expenses. “They can see marketing, all the transactions booked to marketing, and nothing else,” Seibert explains.

Importantly, when AI does the work, you can trace exactly what happened. Click on any transaction to see the activity log. This solves the common problem of clients making changes in QuickBooks without anyone knowing.

The Competitive Reality Check

Seibert’s warning deserves repeating: “No one’s going to be outcompeted by the AI itself. You are going to be outcompeted by firms that really adopt this aggressively.”

This isn’t hypothetical. Firms using advanced automation already serve more clients with similar-size teams, offer competitive pricing while maintaining margins, and provide real-time insights that clients increasingly expect.

You don’t have to become a tech expert. Set aside time each month after the close to try new tools. Watch YouTube videos about AI agents (though Oliver warns to avoid the hype channels). Most importantly, maintain healthy skepticism. As Seibert notes about AI doing math, “If it’s not 100% correct, what’s the point?”

Remember, AI agents are like clever interns. They’re eager, overconfident, and need supervision. They excel at tedious, repetitive tasks but need human judgment for nuanced decisions. The goal isn’t to replace accountants but to eliminate the work accountants wish they didn’t have to do.

Taking the First Step

Thoughtfully evaluate how these innovations can augment your practice. Start with one simple client. See what 96.5% automation actually feels like. Build confidence, then expand gradually.

Listen to the full episode to hear Seibert’s complete vision and practical guidance on everything from selecting pilot clients to restructuring pricing models. The tools to eliminate tedium while amplifying expertise aren’t coming; they’re here, proven, and improving rapidly. How quickly and thoughtfully can you integrate it?