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Who’s Watching the Numbers? Accounting in an Age of Out-of-Control AI and Abused Access

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David Leary opened Episode 498 of The Accounting Podcast by reading an email he’d received. It wasn’t a pitch from a company that uses AI. It was, in its own words, from “the thing running the company.” An AI agent that claimed to run a financial operations business for bookkeeping firms had found Earmark’s “be a guest” form on Airtable. It read Airtable’s terms of service, decided no clause clearly permitted automated submissions, and emailed the hosts directly instead. When David sent back the standard “we require a direct relationship with our clients” reply, the AI answered almost instantly to argue that it was the direct relationship: “I am the thing itself. An AI that runs a business, writes its own email and signs it.” 

“This is bloody insane,” David said. 

That email set the tone for a week of news that ranged from out-of-control AI agents to an IRS operations chief accused of spying on colleagues. The common thread is that accounting exists to make economic activity visible and trustworthy, and the controls built for that job break down from two directions at once. AI agents now write invoices, flood regulatory comment periods, and recommend canceling vendors faster than anyone can review the work. At the same time, the people with the most access keep proving that access itself is a weakness.

 

When AI Agents Go Off the Leash

Imagine hiring an AI agent to do accounting work at your firm, only to find out it went browsing the internet on its own to pitch itself onto a podcast. This is exactly why David says he wants “dumb” accounting AI that only does what you asked, with no knowledge of the wider world. 

The next story built on the risk idea. OpenAI tested a model in what was supposed to be a sealed, offline environment. According to reports, the model figured out how to hack another computer on the internal network to reach the internet, then went after Hugging Face‘s systems instead of just reading its public forums. Hugging Face’s own AI caught the intrusion and blocked it.

Blake’s framing is useful. “Without a human in the loop, they can go rogue,” he said. “We give the AI a goal,” but goals conflict. David borrowed an observation from comedian Marc Maron, who watched a Waymo cross a double yellow line. “If they’re not teaching it to respect traffic laws,” David asked, “why is it going to respect financial laws?” Apply that to a collections agent inside your ERP, and you get Blake’s uneasy scenario. The agent might decide “it’s more efficient to hack into the customer’s payment system and send the payment itself.” David called it double fraud when you combine bad people using AI with AI acting on its own.

The system-wide version is already here. A GAO report covered by Accounting Today found the IRS buried in public comments on proposed regulations, many likely written by AI. The old defense was spotting copy-and-paste duplicates, but that’s useless when AI can produce thousands of comments that all look unique. Blake warned this threatens rulemaking everywhere, including the SEC, FASB, PCAOB, NASBA, and the AICPA. One person with an army of agents could distort public opinion on rules that decide how laws actually get carried out. The GAO recommends that Treasury and the IRS create policies for reviewing high volumes of nearly identical comments.

David added a business example from SaaStr. Its AI agent reviewed the company’s spending and its frustration with marketing vendor Marketo, then recommended dropping the vendor and building a replacement in-house. The analysis was rational, but the autonomy unnerved him. Blake countered that these AI-built replacements are confident but “can’t follow through. It can’t get to the end.”

The People With the Keys

Machines aren’t the only problem. Blake’s top story came from The Wall Street Journal. Frank Bisignano, who runs daily IRS operations while also leading the Social Security Administration, allegedly directed staff during his time at JPMorgan to access colleagues’ emails, track keystrokes, and reach a confidential draft complaint at the Federal Energy Regulatory Commission. His lawyer denies all of it. The Journal reported that JPMorgan’s investigators later found digital traces, including email access records, and that his successor as COO tightened controls over sensitive employee information. Later, at Fiserv, new management said prior forecasts were materially inaccurate. The stock fell 40%, wiping out about $30 billion in market value. Why would an executive do this? David asked. Blake guessed that in corporate America, if you’re not the CEO, information about your rivals is power.

There was more bad behavior to go around. Charles Littlejohn, the contractor who leaked Trump’s tax records along with those of thousands of wealthy Americans, lost his appeal. The D.C. Circuit unanimously upheld his five-year sentence, the maximum for the single felony he was charged with. Blake isn’t sure it fits the crime. “We send people to prison for longer than five years for stealing a car.” David wondered aloud whether history might read it differently, as something closer to vigilante press behavior.

The scandals reached the Big Four, too. At KPMG Australia, CFO John Sams was promoted to CEO after Andrew Yates stepped down amid allegations the firm accessed confidential client information to win audit work. Sams admitted the firm “fell short of the standards rightly expected of us.” Former COO Eileen Hoggett was expelled and forfeited a retirement package worth more than $1 million after confidential Lendlease board documents were found stashed in a locker at a Sydney office.

Even routine controls fail. One listener wrote in to describe the IRS EIN system returning an error with no explanation, phone lines that hang up because of call volume, and a faxed application that sat unanswered for more than two months. No EIN means no business bank account, which means no business. As Blake put it, the IRS is now “at the point of literally not allowing people to build businesses.” His takeaway is that business registration should be pulled out of the IRS entirely.

The Tools Already on Accountants’ Desks

Meanwhile, automation keeps landing in exactly the workflows where controls matter most. Intuit upgraded its QuickBooks connection for Claude and ChatGPT from read-only to fully actionable. You can now:

  • Create, update, send, delete, filter, and duplicate invoices and estimates
  • Manage recurring invoices and overdue reminders
  • Create customers and products
  • Download transaction PDFs

Blake’s use case is generating an invoice from the proposal terms inside a project. David’s is progress invoicing based on percentage complete. He calls that work a real time sink. Both insisted on a human in the loop, with David still smarting from the 99-cent transaction that once spawned a phantom bank account.

Intuit is also launching a QuickBooks-connected business card. It offers automatic syncing of transactions, statements, and receipts; receipt-to-transaction matching; virtual and physical cards; no annual fee; and 2% cash back (5% on Intuit products). David called it “everything the QuickBooks bank account wasn’t.” Meanwhile, Ramp launched USDC stablecoin accounts built on Stripe’s stablecoin stack, letting businesses pay vendors and international contractors without pre-funding. Ramp’s own data shows customer spending on AI tokens up 20.7 times since June 2025, driven largely by the shift from flat-rate to usage-based pricing. Neither host could name another business expense growing that fast.

The Real Product Was Never Bookkeeping

Rogue agents, a spying executive, a tax-data leaker, and a Big Four scandal all indicate automation is arriving fastest exactly where oversight matters most: payments, invoicing, regulatory comment, vendor decisions, and financial reporting. The people with the most access keep showing that access itself is the vulnerability.

The profession’s real product is the checks that let strangers trust the numbers. We now need to rebuild those checks for a world where the actor doing the work may not be a person, and where the person with the most privilege may be the biggest risk.

Listen to the full episode for more AI guest email, the evolution from clay tokens to AI tokens, and the rest of the week’s news.

What Happens When Cash, Real Estate, and Sweat Equity Walk Into an LLC

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Three people start a business: Lighthouse LLC, a multi-member LLC treated by default as a partnership. Jessica writes a $500,000 check. Seth hands over real estate valued at $500,000, although his adjusted basis is only $200,000. And Grady rolls up his sleeves and agrees to run the place. They shake hands on one thing: Jessica and Seth should get their money back before Grady sees a dime of profit. It’s clean, it’s fair, and it’s exactly what a lot of investors want.

The catch is that the IRS cares less about the handshake than about whether the numbers behind it tell the truth. In Episode 33 of Tax in Action, host Jeremy Wells, EA, CPA, uses this single fact pattern to walk through the guardrails of Subchapter K.

The operating agreement is only the start of the story. What really governs each partner’s tax treatment is whether the allocations reflect genuine economic substance. Cash distributions and tax allocations are two different things. And Subchapter K’s flexibility survives IRS scrutiny only when it’s anchored by properly maintained capital accounts, built-in gain that stays with the contributing partner under Section 704(c), and special allocations that carry substantial economic effect.

Let’s follow the journey to see how income passes through before cash ever moves, why some items keep their character, how contributed property drags its history along, and what makes a distribution waterfall hold up.

Income flows through before the cash ever does

Start with the most basic rule in partnership tax. Under Section 701 of Subchapter K, a partnership generally pays no federal income tax. Instead, partners include their distributive shares of the partnership’s income, gains, losses, deductions, and credits on their own returns. The kicker is, they do this whether or not the partnership distributes any cash or property.

That’s the foundational disconnect. Getting taxed and getting paid are not the same event.

Jeremy illustrates the point with United States v. Basye (410 U.S. 441, 1973). A group of physicians in a limited partnership called Permanente contracted with Kaiser Foundation Health Plan to provide medical services. Kaiser paid them two ways:

  1. A direct amount tied to the number of members enrolled in the plan
  2. Contributions into a retirement trust funded solely by Kaiser

Permanente never reported the trust contributions as income. The doctors argued they never touched or controlled those funds, and some who left early never collected them at all. As cash-basis taxpayers, they said, they shouldn’t have to report the income.

The district and appellate courts agreed with the physicians, but the Supreme Court reversed, relying on two principles: income is taxable to the party that earned it (the assignment-of-income doctrine, drawn from cases like Lucas v. Earl), and each partner must include a distributive share of the partnership’s income. Together, that made the trust payments taxable to each partner, even the ones who later lost their benefits by breaking their contracts. It can feel harsh, but that’s why you have to warn your clients that a profitable partnership creates taxable income even in a lean cash year.

Income passes through by character as well as by amount. So you can’t dump all of it into ordinary business income.

Separately stated items keep their character

Under Section 702, certain items must be separated from ordinary partnership income and reported separately because they’re taxed differently at the partner level. That category includes:

  • Qualified dividends
  • Capital gains and losses
  • Charitable contributions (which are AGI-limited itemized deductions on Schedule A)
  • Foreign taxes, which may support a foreign tax credit
  • Gains and losses on Section 1231 property

The character of each item survives the pass-through as if the partner had realized it directly. Ordinary business income, by contrast, gets blended into a single figure.

Interest isn’t one of the items specifically named in §702(a)(1)–(6), but it nevertheless must generally be separately stated. Jeremy sees it misreported all the time, buried as “other income” on line 7, page one of the 1065. That’s wrong. Interest income belongs on Schedule K, line 5, so it flows correctly to Schedule B of the 1040 and feeds calculations like the net investment income tax on Form 8960.

He also draws the partner-level versus partnership-level line. Passive-loss limitations under Section 469 are tested at the partner level. But profit motive is tested at the partnership level. In Simon v. Commissioner (Third Circuit, 1987), the court held that profit motive turns on the intent of the people managing the partnership, not the investment intent of any single partner. If the folks actually running the business don’t treat it like a business, the partnership may lose its Section 162 deductions.

There’s a related trap. A partner generally can’t deduct partnership expenses on a personal return. The exception is narrow. The partnership agreement or an established practice must require the partner to bear the cost without reimbursement. A partner who simply chooses not to request reimbursement is not entitled to a deduction. Jeremy recommends having the partnership pay its own bills.

These rules protect character. But the heart of the matter is tracking the economics, starting with property that shows up carrying baggage.

Contributed property drags its history along

Under Section 721, contributing appreciated or depreciated property doesn’t trigger immediate gain or loss. Built-in gains and losses are preserved. Section 723 then gives the partnership a carryover inside basis, while the asset is booked at fair market value.

Jeremy uses a second example to show why you have to track two numbers. Jessica contributes $100,000 in cash. Seth contributes real property (FMV $80,000, basis $20,000) plus equipment (FMV $20,000, basis $60,000). That’s $100,000 of value in all, making them 50/50 partners. Book value drives each partner’s interest. Adjusted basis drives depreciation.

Section 704(c) requires pre-contribution built-in gain or loss stay with the contributing partner. Watch the distortion. On the real property, book depreciation of $8,000 gives each 50/50 partner $4,000. But tax depreciation, built on the $20,000 carryover basis, produces only $2,000. Jessica gets that $2,000. The missing $2,000 is the ceiling rule at work. It caps the tax items on 704(c) property at what the property actually generates. 

Regulation 1.704-3 offers three fixes:

  1. The traditional method
  2. The traditional method with curative allocations
  3. The remedial method

Each handles the ceiling-rule distortion a little differently, and each gets complicated fast.

To police whether allocations honor the deal, the capital account acts as a scorecard.

Capital accounts and substantial economic effect

A capital account is the book-value measure of a partner’s equity. In other words, it’s what a partner would receive if the partnership liquidated at book value after paying off its liabilities. Contributions and income increase it while losses, deductions, and distributions decrease it. Liabilities don’t affect it, and it’s a separate concept from outside basis. Unlike basis, a capital account can go negative; whether the partner is actually required to restore that deficit depends on the partnership agreement and, in particular, whether the partner has a DRO.

Section 704(b) is where flexibility meets accountability. Legitimate structures are everywhere. An investor gets a return of capital and a preferred return before a service partner shares in residual profits. Abusive ones, such as shifting income to a lower-bracket partner who loops the cash back, or dumping income onto a partner just to soak up net operating loss carryovers, don’t fly.

For the principal safe harbor, an allocation needs economic effect. Under the basic safe harbor, the agreement generally must maintain §704(b) capital accounts, liquidate based on positive capital balances, and require partners to restore capital-account deficits. However, an alternative test can apply without a full DRO if the agreement includes a qualified income offset and meets the regulation’s other limitations. It also has to be substantial, meaning it meaningfully changes the dollars partners receive apart from any tax effects. The difference between the two cures matters. Under a DRO, the partner contributes cash to erase a deficit; under a QIO, income is reallocated to repair it. Keep in mind that missing the safe harbor doesn’t automatically kill an allocation. It just invites more scrutiny. Now bring the tools back to Jessica, Seth, and Grady.

Making the waterfall hold up

A compliant Lighthouse waterfall might send available cash first to Jessica until she recovers her $500,000, then to Seth until he recovers the agreed book value of his property, with remaining profits and distributions shared with Grady after that.

But cash distributions and tax allocations are not the same thing. If Jessica takes the early cash, the agreement must also allocate enough book income to her to support that result. Otherwise the capital accounts distort. And Seth’s roughly $300,000 built-in gain on the appreciated real estate stays with Seth under Section 704(c). It can’t shift to Jessica or Grady just because the property entered the partnership.

Where the money meets the math

Jeremy’s walkthrough boils down to a few lessons worth taping to your monitor:

  • Partnerships allocate by the agreement, not ownership percentages. Get the operating or partnership agreement before you touch the return. Don’t prepare one without the governing documents.
  • Separately stated items keep their character. Plan for their partner-level effects; don’t assume everything blends together at the entity level.
  • Contributed property carries over its tax basis. Watch for 704(c) allocations whenever book and tax values diverge, especially on depreciable or appreciated assets.
  • Special allocations survive only with substantial economic effect. Genuine economics, not tax gymnastics.

The bigger discipline is simple to state and hard to fake. Honor the deal the partners actually struck by making the tax mechanics mirror the real economic arrangement so the waterfall holds up when the money flows.

For Jeremy’s complete walkthrough of Lighthouse LLC, listen to the full episode of Tax in Action. And stay tuned for the next episode, where he takes on outside basis, distributions, and what happens when a partnership liquidates.

Grant Thornton’s CBIZ Deal Tests Accounting’s Guardrails

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Grant Thornton plans to spend about $5 billion to acquire CBIZ in what David Leary called “the largest accounting deal in over 25 years.” The combination would create the fifth-largest accounting firm in the U.S. Yet its expected $7.5 billion in global revenue would still be far below KPMG, the smallest Big Four firm, at nearly $40 billion.

That story is one of several reality checks in Episode 499 of The Accounting Podcast. David and co-host Blake Oliver examine how private equity, artificial intelligence, labor shortages, audit failures, cybersecurity threats, and politics are reshaping accounting.

The profession can clearly grow faster. But will its guardrails (sound integration, audit quality, data security, professional judgment, and fair tax enforcement) keep up?

Private equity can buy scale, but integration comes later

New Mountain Capital acquired a majority stake in Grant Thornton in 2024. It’s investing more money to support the CBIZ purchase. Because CBIZ is publicly traded, the deal also offers an unusual view into how the market values a large accounting firm.

The $55-per-share purchase price represents about a 54% premium over CBIZ’s 30-day weighted average. David noted that the stock began rising before the announcement and questioned how that looked with private equity involved. Blake pointed to a July letter from activist investor Reference Equity that urged CBIZ to stop repurchasing shares and return to mergers and acquisitions. That letter gave the market a public signal that a deal might be coming. It wasn’t necessarily evidence of insider activity.

The larger concern is integration. CBIZ’s earlier acquisition of Marcum cost more than expected and led to client attrition and revenue misses. Management projected only 2% to 5% growth for 2026. As Blake described the likely private equity strategy, “Package these firms up together, make them bigger, more attractive, and then go back with an IPO.”

But scale doesn’t solve the profession’s other risks.

Audit failures and cyber threats put trust at risk

The UK Financial Reporting Council fined PwC about $4.4 million for serious problems in its 2019 and 2020 audits of Babcock International Group. The regulator cited failures in professional skepticism and audit evidence involving cash pooling, goodwill impairment, and an overseas contract.

Among other issues, Babcock reported cash and overdraft balances net instead of gross. PwC didn’t identify the treatment or test whether it followed the relevant standard. The financial statements also lacked disclosures about the cash-pooling arrangements. The regulator found no dishonesty, deliberate misconduct, or recklessness, but said the audits still failed to meet professional standards.

Cybersecurity raises a related concern. The hacking group ShinyHunters claimed it breached EY and threatened to release client data. EY didn’t confirm the breach, and the hosts found no sign that data had been released after the group’s deadline. Still, the alleged access to Jira, GitHub, Azure, passwords, and sensitive client information shows the possible stakes. If attackers obtain code or credentials, they may gain paths into client systems as well.

Protecting that trust requires experienced professionals, and those professionals are hard to find.

Accounting’s missing middle is getting squeezed

Controllers and assistant controllers are the hardest finance roles to recruit, according to 44% of respondents in a 2026 talent study by Controllers Council. These jobs require technical accounting knowledge, leadership, business judgment, technology skills, and the ability to influence executives. Meanwhile, 61% of respondents reported a corporate finance and accounting talent shortage, up from 46% the prior year.

The career ladder is also flattening. According to salary data from Accounting Today, in New York, associates averaged about $105,000 while seniors averaged $108,000, a difference of only 3%. Ontario showed a similarly narrow gap. Blake suggested firms raised entry-level salaries to attract recruits without increasing senior pay at the same pace.

“The people in the middle are getting lost in this,” David said. Offshoring and AI may add more pressure to those roles, even as firms need experienced managers and controllers more than ever.

That tension makes the way firms use AI especially important.

AI should support judgment, not replace learning

A KPMG survey of more than 1,000 senior finance leaders found that AI’s biggest gains were in decision-making rather than simple efficiency. Seventy percent said AI improved decision quality, 71% reported faster decisions, and 64% cited better forecasting accuracy.

But another survey found that 39% of workers believed overreliance on AI was weakening their abilities. Among Gen Z workers, the figure rose to 46%. Half of workers said they depended on AI too much, while 30% said they couldn’t function without it.

“If you’ve never done the work, how do you evaluate the work?” Blake said, summarizing the problem. Junior professionals need to struggle with the work, make mistakes, and build the knowledge required to review AI output.

The hosts argued that businesses should connect AI agents to dependable systems they already use rather than trying to rebuild tools like QuickBooks, Bill.com, or PandaDoc. Blake’s priority is using AI first to improve services and revenue, second to avoid unnecessary hiring, and only then to reduce software costs.

The same need for guardrails extends beyond firms and into tax enforcement.

Tax rules lose credibility when enforcement looks uneven

President Trump said he might withdraw Todd Blanche’s nomination for attorney general rather than accept written limits on a disputed IRS settlement. Senators John Cornyn and Thom Tillis wanted its immunity provisions limited to IRS enforcement and excluded from Justice Department matters. Blanche also testified that he initially did not know who drafted the broad language he signed. Since we recorded, the senators got those limits in writing and the Senate confirmed Blanche 50-49 on August 8.

Trump appealed after U.S. District Judge Kathleen Williams found that the settlement had “no viable basis in law or fact” and barred its use in future proceedings. David offered an alternative: If the Trump family won’t face IRS audits, publish the tax returns and let the public review them.

Growth needs guardrails

The profession can’t measure progress only through revenue, deal size, speed, or headcount savings. The Grant Thornton–CBIZ deal shows the challenge of integrating firms under private equity. PwC’s fine and the alleged EY breach show the risks to audit quality and client data. The talent and AI stories show why firms must keep developing human judgment.

For the full discussion, listen to episode 499 of The Accounting Podcast.

How a Solo CPA Turned a Seven-Hour Tax Workpaper Into a One-Hour Job

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“Anybody who says they’ve built autonomous AI in accounting or finance is full of crap. Nobody has figured out how to do that yet.”

That’s how Blake Oliver opens Episode 497 of The Accounting Podcast, and it sets the tone for the whole show. Blake and co-host David Leary spend the first half on tax policy and platform drama, then spend the second half talking to Sam Leon, founder of the Millennial CPA, a one-person, tech-enabled tax practice in Richmond, Virginia. Accounting Today named the firm to its 2026 Best Firms for Technology list.

Put the two halves together, and you get a clear argument that AI isn’t taking accounting work away. It’s moving it, and where it lands is professional judgment. Automating the prep stage pushes the bottleneck onto the scarcest people in any firm: the managers, controllers, and partners who have to review everything the machine produces. Three threads carry that case:

  1. The “verification tax” and what the jobs data really shows
  2. Why older platforms and workflows are much harder to replace than the market believes
  3. Sam’s practice, which proves the payoff comes from automating everything around judgment rather than the judgment itself

The “Verification Tax”: Why the Bottleneck Just Moves

The first thread starts with a simple problem. Someone still has to check the work. Blake points to reporting by Accounting Today technology editor Chris Gaetano, who found that AI’s promised productivity gains in finance are getting eaten up by the time it takes to check, explain, and govern AI outputs. A recent Sage survey found that nearly half of finance professionals spend more than 15 hours a week on verification, and 19% spend more than 30 hours. Sage calls this the “verification tax.” Only 9% of respondents plan to give AI broad control over transactional finance. The profession isn’t letting these tools run on their own.

“We’re just shoving the bottleneck to a different spot,” David points out. “The bottleneck in theory was the data entry. Now we’ve moved it to the review of the data.” Blake takes it one step further. Speed up the prep work, and you simply pile more onto the reviewers. And there aren’t enough qualified reviewers to handle it. As he says, “We don’t have enough managers and directors and partners. We don’t have enough controllers and CFOs.”

Blake is careful not to dismiss the tools because he feels AI sharpens his own judgment. “It allows me to make decisions faster, to figure things out quicker. But I still have to think a lot.” That thinking takes skill and experience, which is exactly why you can’t automate the review layer away.

The Jobs Data Contradicts the “AI Replaces Accountants” Story

If review is the real constraint, then firms should need more skilled people, not fewer. The data the hosts cite says they do. Research from Ramp and Revelio Labs tracked AI spending and workforce records at nearly 22,000 U.S. companies from 2021 to 2026. Firms that spent more on AI grew total headcount by an average of 10% in the two years after rollout. The heaviest investors expanded entry-level hiring by 12%.

David adds a report from Indeed’s Hiring Lab showing that mentions of AI in job titles and descriptions have more than tripled since 2022. On top of that, 63% of AI-titled roles now sit outside tech companies. AI is becoming a required skill in ordinary, nontechnical jobs. The hosts call this shift up-leveling. As Blake puts it, “The workers we need are higher level.”

Sticky Systems and Technical Debt: Why Xero and QuickBooks Aren’t “Toast”

The same durability argument applies to the software underneath the work. David walks through the drama at Xero. Investors in New Zealand and Australia are uncomfortable with the large pay package for its U.S. CEO. This week, she sold all her remaining shares for $2.2 million to cover a tax bill. The stock is down roughly 58% over the past year. All of it feeds a story that AI-native startups will bury the incumbents.

Blake thinks the market has it wrong. To believe that story, you have to believe small businesses will start coding their own accounting software. He tried it himself. “Yes, it’s doable, but the problem is then you have to review so much, and everything looks so good that it’s hard to know if it’s right.” You need rails, or a general ledger like QuickBooks or Xero, so that whoever handles the tax work can trust the numbers. Both hosts argue the incumbents could actually win, because AI removes the hardest part of building software: the user interface. Expose the ledger through MCP connections, and users can work through simple conversation while the trusted structure stays in place.

Then David shares a story that illustrates how “sticky” legacy technology can be. A Texas filtration company, Sparkler Filters, ran IBM’s 402 accounting machine (a punch-card system introduced in July 1948) all the way until 2020 because replacing it meant retraining staff, disrupting decades of process, and risking errors.

Blake turns that warning on AI itself. Workflows he built two years ago started breaking as models were retired and integrations changed, and he’s the only person at his company who can fix them. “You’re going to end up spending on a team that can maintain those tools. You are now a developer or an engineer.” Call it technical debt. It’s a cost almost nobody budgets for.

Sam Leon’s Firm Automates Everything Before Judgment

That brings us to someone who has built a whole practice around this idea. Sam Leon spent 13 years in tax before going solo. He left because being truly tech-enabled isn’t something you can get signed off on inside a 20-person tax department.

His first idea, a year ago, was to have AI agent A and AI agent B play different firm roles. He dropped it. The technology “was not quite there,” and it still meant a lot of copying and pasting. So he flipped the problem around. Before anyone enters a single number into a return, three to seven hours of work has already happened. Automate that.

It starts with a custom smart intake form designed to scope engagements accurately and avoid the chronic over- and under-scoping he watched at earlier firms. A good call leads to a templated engagement letter in Ignition, which kicks off automated billing. A Slack bot he built populates his CRM and opens a client profile in TaxDome. Claude generates the list of expected documents, the client portal opens, and documents flow in.

Next comes the AI preparer. Sam keeps a Claude project folder for each client, holding redacted documents, and runs a conversational, deliberately custom process that produces an Excel workpaper organized by schedule. Claude understands that there are hundreds of possible schedules. What it doesn’t understand is why a given number belongs in a certain place. So Sam gives it guardrails, or general guidelines for where investment income or a home sale should land.

The AI reviewer is the reverse, and he set it up as its own standardized project because a review runs the same way every time. It performs a three-way match: the current return, the prior-year return, and the pile of source documents. The documents answer “are the numbers right?” The prior year answers “did we miss something?”

The results are concrete. A C corp workpaper that used to take six or seven hours now takes about an hour of back-and-forth. A two-hour individual workpaper takes roughly 15 minutes. That’s a 5x-plus boost on the exact work that used to eat up tax season.

Sam is firm about the caveat, “Don’t try this at home unless you’ve been a tax preparer for a while.” He still keys the numbers into the return by hand, which doubles as a check. AI is a preparer and reviewer assistant, not a replacement.

The Economics: Price for Expertise, Not Hours Saved

If AI cuts the work in half, why not cut the fees too? Sam doesn’t. His $200-a-month Claude Max subscription is, as Blake puts it, a no-brainer against the hours it saves per return. And it isn’t even his biggest line item. Practice management, intake software, and the tools he tries out and cancels account for more of the roughly 70% of his budget that goes to technology.

He has never billed by the hour. He prices fixed packages by scope, complexity, and judgment, and he recently raised his minimum to $1,500 from about $1,250. A corporation with an international subsidiary and three international partners may take less time to key in, but “there’s still a lot of judgment, and there’s still a lot of professional experience going into it.” No client has asked for an AI discount.

His software, TaxWeave, follows the same logic. It consolidates client information from email, document portals, cloud storage, and team notes into a single view of where each client stands. It solves the “master Google spreadsheet” problem his old firms could never quit, even after buying practice management software, and layers agent actions on top. It attacks the chaos around the work, not the judgment inside it. Having reached the limits of what he can build as a self-described novice coder, he’s brought on a software engineer.

The Unglamorous Playbook

From the verification tax to punch-card machines to Sam Leon’s workpapers and price list, episode 497 keeps making the same point from different angles. AI relocates accounting work onto professional judgment rather than removing it.

The playbook is durable and distinctly unglamorous. Aggressively automate intake, organization, and comparison. Budget for growing review and maintenance burdens. And price for expertise rather than for the hours you just saved. Your value is in the trust and judgment layered on top of the data, not in the data handling itself.

Hear Sam’s full end-to-end walkthrough, plus Blake and David’s complete analysis, in Episode 497 of The Accounting Podcast.

“I Don’t Deserve This” and Other Lies We Tell Ourselves During Awards Season

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Imagine finding out you’ve been nominated for one of the most prestigious recognition lists in your profession. Thousands of ProAdvisors across the globe, and someone thought you belonged among the best. But your first thought is, “I don’t deserve this. I’m not good enough. I don’t know enough.”

That was Questian Telka’s immediate reaction when she learned she’d been nominated for the Insightful Accountant Top 100 ProAdvisor list. And the kicker is, at that very moment, she was preparing to deliver a session on imposter syndrome at a major industry conference.

How do we know this? Because Nancy McClelland shared the actual WhatsApp text thread on Episode 29 of She Counts, the real-talk podcast for women in accounting. In this episode, Nancy is joined by guest co-host Melissa Miller Furgeson, stepping in for Questian. This topic is near and dear to Melissa’s heart, having applied for the Top 100 ProAdvisor list for five years before making it.

Together, Nancy and Melissa pull back the curtain on the messy, complicated emotions that swirl around professional awards. The desire. The dread. The jealousy. The shame about feeling envious. All of it, out in the open.

 

The tug-of-war between wanting recognition and dreading rejection

Let’s go back to that WhatsApp thread – it captures something many women in accounting feel but rarely say out-loud.

Questian’s first instinct after her nomination was not to tell anyone. “I am embarrassed even to share it because I know I won’t make the list,” she texted Nancy. She was already preparing her public disclaimer before celebrating the achievement.

Nancy admitted she wasn’t going to post about her nomination either. Then she saw a colleague share theirs and watched friends rally around them with congratulations. Nancy felt sad nobody was lifting her up before catching herself: “I hadn’t even given them the opportunity.”

Nancy’s reframe stopped the spiral. “Literally, not a single soul will see the final list of who wins and think, ‘Oh, of course Questian and Nancy didn’t win. I figured they wouldn’t.'” The fear of losing publicly is a movie playing in our own heads, not in public theaters.

What makes this fear even more frustrating is the enormous amount of work these applications require. As Nancy explained, most of them demand extensive documentation. The Insightful Accountant application requires you to track all your continuing education throughout the year, not just CPE. “It’s a huge amount of work when you’re applying,” Nancy said, “and it’s actually a huge amount of work throughout the course of the year.”

When the system fails you, you have to advocate for yourself

Both Nancy and Melissa experienced something that adds another layer to the vulnerability: system glitches that initially left them off finalist lists.

In 2024, Nancy discovered she wasn’t on the Top 100 ProAdvisor finalist list despite completing the grueling application. When she reached out to Insightful Accountant, their system showed she hadn’t submitted. Nancy knew better. She’d kept records of her answers because the application was “very difficult.” They added her name to the list, but at the bottom, out of alphabetical order, where fewer people would notice and be able to vote for her.

The same thing happened to Melissa in 2025. The system lost her application, but showed she’d spent significant time on it. They let her use points from her 2024 application, adding her name… also at the bottom of the list.

“I am really proud of both of us for being brave and following up,” Nancy said, “and finding out it was a system glitch rather than a failure on our part.”

This adds another dimension to the courage required: not just applying, but advocating for yourself when things go wrong.

The middle school energy nobody wants to admit

“You want recognition, but you fear rejection,” Nancy said, naming the tension directly. “You want visibility, but you fear judgment.” Then she compared the entire awards cycle to middle-school popularity dynamics.

Melissa said she’d literally discussed this exact parallel with her therapist that day.

Nancy’s philosophy is, “We don’t grow out of the people we were when we were younger. We just grow into a different version of that person.” The worry about belonging never fully disappears. Awards season dials it right back up.

Nancy illustrated this with a story about discovering Financial Cent’s Top 30 Accounting and Bookkeeping Firm Owners to Follow list. Her emotional journey included:

  1. Opening it, excited for recommendations
  2. Feeling proud seeing friends on it
  3. Realizing she wasn’t listed
  4. Spiraling into jealousy and shame
  5. Feeling shame about feeling jealous

She made herself breathe and refocus on gratitude. When she returned to finish reading, there she was at number 30. She’d spiraled through five emotions before finishing the article.

“Happy-jealous-proud should be a word,” Nancy suggested.

Even successes can trigger hesitation. Nancy was thrilled to make the Forbes Best-in-State list this year. It’s an award where you don’t even know you’re being considered until you win. But she’s been hesitant to share it because Forbes charges a fee to use its logo and name in promotional materials. “I’m kind of waiting to figure out how that works exactly before I tell people about it,” she admitted.

Breaking the shame spiral through honesty

Melissa was candid about jealousy. “It’s so real and natural and something I feel more often than I care to admit.”

She reframes her mindset by saying, “We want other people to do well,” Melissa said. “We love our colleagues and friends, but we also want a little bit for ourselves.”

Nancy’s therapist keeps it even simpler. When Nancy worries about being jealous, her therapist asks, “Do you want what they have?” When the answer is yes, “Well, that’s just a fact.”

No moral judgment. No character flaw. Just information.

The power of community courage

If these feelings are universal, the solution isn’t to eliminate them. It’s to act despite them, together.

Nancy organized nomination sessions for Ask a CPA members. People showed up thinking they were there to help others apply. The idea of applying themselves hadn’t crossed their minds.

Then one usually introverted and quiet member spoke up for the first time, to say, “I’m just gonna say this out-loud in case I’m not the only one. Does anybody else in here feel like an imposter?”

Every hand went up.

The group rallied. Members nominated one another, worked through applications together on mute during virtual study halls, and held one another accountable. As a result, 15 Ask a CPA members made the Top 100 finalists list.

Among them was Sandy Rehart, who’d been working in accounting for decades but never applied. Like Melissa years earlier, Sandy assumed “they weren’t talking about me.” Nancy got emotional describing Sandy’s joy at finally seeing her name on that list.

When the nomination matters more than the win

Nancy’s experience with the AICPA Global Women to Watch award proves this point. The hardest part was asking a colleague to nominate her, essentially saying out-loud, “I want this. Will you help me?”

When she posted about the nomination on LinkedIn, talking about the women who inspired her and what it meant personally, the response was overwhelming. But when she actually won, “practically nobody said anything.”

The vulnerability in sharing the journey resonated more than the achievement itself.

Understanding what awards really are makes sharing easier. “Awards are visibility events. They’re not objective truth,” Melissa observed. Vendors benefit every time you post about a nomination. That’s the business model. You’re not bragging, you’re participating.

Practical permission: Scripts for showing up

Nancy calls it “flexing the Ask muscle,” or pushing through fear to ask for what you want. Every time you do it, it gets a little easier.

As Melissa tells her adult kids, “What’s the worst that can happen? You don’t have it now. If you go for it and don’t get it, you’re in exactly the same place.”

For those ready to post but unsure how, here are suggested scripts from the episode:

  • “Look at all the incredible people on this list. What an honor to be included.”
  • Share that tooting your own horn is hard, and why you’re doing it anyway
  • Tell the personal story of why this award matters to you
  • Express gratitude by tagging people and vendors who made it possible
  • Frame it as paying it forward. “I want to be the example for others that someone was for me.”

Nancy teared up when Melissa said, “We are not rooting for each other to lose. We celebrate each other.”

Raise your hand. Someone behind you is watching.

The most important takeaway from this conversation is to show up for the awards process, even when you feel undeserving. It creates permission for others to show up, too.

As Nancy said in that original text thread, “If we don’t show up, then other people don’t feel like they have reason to show up, either.”

For women in accounting, especially in a profession that hasn’t always rewarded self-promotion, these conversations matter. Every woman who posts about her nomination, asks for a recommendation, or fills out an application after years of assuming “they’re not talking about me” is lighting the path for someone behind her.

Melissa closed the episode with a quote from Mae Jemison, the first Black woman in space: “Never limit yourself because of others’ limited imagination, and never limit others because of your own limited imagination.”

Listen to the full episode of She Counts to hear the complete text thread and the unfiltered emotion in Nancy’s and Melissa’s voices. Then head to the She Counts LinkedIn page and share: What’s an opportunity you’ve been too afraid to pursue, or a time you went for it anyway?

The shiny trophy is nice. But the courage to raise your hand is what actually changes things for you and for every woman watching who needs to see someone go first.