Author: Kreig Mitchell

  • Tax Planning for Net Operating Loss Carryback Elections

    Congress has used Section 172 for net operating losses to stimulate the U.S. economy. It has done this by allowing certain losses to be carried back, thereby generating cash refunds to the taxpayer. This puts cash into the hands of taxpayers who are suffering losses. One only has to look at the history of changes… Continue reading Tax Planning for Net Operating Loss Carryback Elections

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  • Who Qualifies as a “Designer” for Section 179D Energy Tax Deductions?

    Contractors regularly upgrade HVAC systems and lighting in commercial buildings to improve energy efficiency. These projects can be expensive. When the building owner is a government entity, the tax code allows contractors to claim an immediate tax deduction for the cost of energy-efficient improvements under Section 179D. But not every contractor who touches the building… Continue reading Who Qualifies as a “Designer” for Section 179D Energy Tax Deductions?

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  • Where AI Earns Its Keep in Professional Services, and Where It Quietly Fails

    There are two ways to be wrong about AI in professional services, and almost every firm is wrong in one of them. The first is to treat AI as a discontinuity — to assume it is about to remake the profession, displace the practitioners, and reward the firms that bet aggressively on rebuilding themselves around it. The second is to treat AI as a fad — to assume it is hype, that the existing way of doing things will reassert itself, and that any investment in it is a tax on a profession that has worked fine for a hundred years. Both views are reassuring in their certainty. Both are wrong. The reality is messier and more interesting, and getting it right requires resisting the urge to be certain about something that is still in motion.

    Every conversation about AI in professional services eventually arrives at the same set of questions. Will AI replace attorneys, accountants, bookkeepers? Will small firms lose to large firms with better technology? Will technology-first competitors disrupt incumbents? These are the wrong questions, or at least they are the wrong first questions. The right first question is far more boring: where, specifically, in the work that this firm does every day, can AI make the work better?

    The honest answer for most small firms today is “a few places, narrowly, with careful supervision.” That is less exciting than the broader claims, but it is what we actually see when we deploy these tools inside our firms. The places where AI works are surprising. The places where it does not are also surprising. The difference between the two has almost nothing to do with the underlying model and almost everything to do with the structure of the work — which is the part that gets the least attention in the AI discourse and that, in our experience, matters the most.

    Where AI Earns Its Keep Today

    Document review. Not the final review by an attorney, but the first-pass triage. Finding the relevant clauses in a hundred-page contract, surfacing the unusual provisions, comparing against a known good template. The attorney still does the legal judgment, but she does it on a curated and annotated document instead of a raw one. The time savings are real. The accuracy improvement is also real — the AI does not get tired on page sixty, the way a human reviewer does, which means the unusual clause that hides on page sixty-two no longer gets missed.

    Drafting. Standard letters, standard motions, standard engagement letters, standard responses to common client questions. The output is never publishable as-is, but it is far better than starting from a blank page. The skill is in writing the prompt correctly and in editing the output rigorously. The associate who knows how to do both does the same work in half the time. The skill of editing AI output is, importantly, not the same as the skill of drafting from scratch. It requires a different cognitive posture — a critical, suspicious, line-by-line read rather than a generative one. Firms that train their associates explicitly in this skill get more out of AI drafting than firms that simply hand the tools to the team and hope.

    Research. Tax research, case research, regulatory research. AI search is good at finding the relevant authority. It is not yet good at synthesizing the authority into a defensible answer. So we use it to find what to read, not to decide what to do. The distinction is operational: AI is a research assistant, not a research conclusion. The firm that treats it as a research conclusion will eventually issue an opinion that is wrong, lose a client over it, and discover that AI hallucination is not a theoretical risk — it is a malpractice risk hiding inside a productivity tool.

    Bookkeeping categorization. The marginal AI improvement here is enormous because the work is repetitive, the categories are well-defined, and the corrections are easy to learn from. The bookkeeper goes from coding every transaction to reviewing the AI’s codings. Throughput doubles. Accuracy goes up. This is the canonical example of AI fitting the structure of the work — a high-volume, well-defined, correctable task with clear feedback loops. Where the structure of the work matches the strength of the model, the value is unambiguous. Where the structure does not match, no amount of model improvement helps.

    Where AI Quietly Fails

    Anything that requires the model to understand who the client actually is, what they actually want, and what they have actually agreed to. AI does not know your client. It cannot tell you whether the answer that is technically correct is also the answer your client should hear, in the way your client should hear it, given the relationship you have with them.

    Anything that involves novel judgment. The first time a fact pattern looks like X but is actually Y, AI will get it wrong, because it is averaging across cases it has seen. The exceptions are where the practitioner earns her living. AI cannot replace the practitioner there and probably should not try.

    Anything that introduces material risk. We do not let AI send anything to clients without human review. We do not let AI sign anything. We do not let AI make decisions that we would not let a first-year associate make on her own. The standard is the same one we have always used for first-year work: useful, but always reviewed.

    The “quiet failure” framing in this section’s title is deliberate. AI does not usually fail loudly. It fails by producing output that looks plausible, that is wrong in ways that are subtle, and that requires a knowledgeable reviewer to catch. The firms that get hurt by AI are not the firms whose AI tools crashed. They are the firms whose AI tools worked just well enough to be trusted by people who did not have the skill to verify the output. The reviewer-skill problem is the actual problem. The model-quality problem is a secondary one, and it is one the vendors will solve faster than the reviewer-skill problem will be solved. The firms that invest in their reviewers’ AI literacy are the firms that will use AI well over the next decade. The firms that invest only in tools are buying half the answer.

    The Deterministic Layer Is the Point

    We have written elsewhere about the line between deterministic systems and nondeterministic ones. AI is nondeterministic by nature. The work in our firms is mostly deterministic by nature — the same kinds of matters, the same kinds of documents, the same kinds of decisions, with the same kinds of safeguards. The way we use AI is to put nondeterministic steps inside deterministic workflows, with deterministic checks on the output. This is unglamorous and it is also what works.

    A modern tax controversy practice looks the same as it did five years ago from the client’s perspective. The forms are the same. The deadlines are the same. The IRS is the same. What has changed is that the steps in between — pulling transcripts, summarizing notices, drafting responses, calculating projections — happen faster and with fewer errors. The practitioner spends more time on the substantive judgment and less time on the mechanical work. That is the entire promise of AI in this kind of practice, and it is enough.

    The architectural insight here is worth stating explicitly. The job of the firm is to deliver deterministic outcomes — the right legal advice, the right return, the right book of accounts. The job of the workflow is to deliver those outcomes reliably. AI is a tool that can do some of the intermediate steps faster, but it cannot be allowed to compromise the determinism of the outcome. So we wrap the nondeterministic AI steps in deterministic scaffolding: a structured input, a known-good template, a human reviewer, a checklist verification. The scaffolding is the firm’s promise to the client. The AI is the productivity multiplier inside the scaffolding. Firms that get this layering right move faster without losing reliability. Firms that get it wrong move faster and lose reliability at the same time, and the loss of reliability is not visible until the first time it matters, at which point it is too late.

    The Talent Implication Most Firms Miss

    The popular narrative is that AI will reduce the need for junior associates. The narrative is partially right and mostly misleading. The mechanical work that junior associates used to do — first-pass document review, basic research, template drafting — is exactly the work AI is best at. So firms will indeed need fewer hours of that work from juniors. But the firms that will thrive are the ones that take the time they used to spend supervising juniors on mechanical work and reinvest it in training juniors on the judgment work that AI cannot do. The output is the same headcount, but a different developmental curve — juniors who are doing harder, more cognitively demanding work earlier in their careers, and reaching senior judgment maturity faster than their predecessors did.

    The firms that get this wrong will hollow out their talent pipeline. They will keep the same supervision model — juniors doing mechanical work, seniors reviewing it — but with AI in the middle, which means the juniors are not actually doing the mechanical work, which means they are not building the muscle that the mechanical work used to build. Five years later, those firms will have senior associates who have never had to read a hundred-page contract from cover to cover, and who therefore cannot reliably catch the things that the AI missed. The talent risk of AI is not that it will replace the juniors. The talent risk is that it will produce a generation of seniors who never developed the underlying skill that AI is now imperfectly performing. The cure is to be deliberate about what juniors do learn, given what they no longer have to do.

    What We Are Building Toward

    Over the next several years we expect AI to keep moving from optional to assumed inside the firms we own. The associates we hire will use it because it makes their work better. The clients will benefit because the work will be faster, cheaper, and more accurate. The competitive advantage will accrue to firms that integrate AI carefully into their existing workflows, not to firms that try to rebuild themselves around it. Quiet integration beats loud rebranding every time.

    The firms that will struggle are not the ones that are slow to adopt AI. They are the ones whose underlying processes were so undocumented and so ad-hoc that they cannot tell where AI would fit. The pre-condition for using AI well is having a real process to begin with. That has always been the pre-condition for everything else in a professional services firm, too. AI is not a way to skip the work of building a real firm. It is a multiplier that rewards firms that have already done the work. The multiplier on zero is still zero, and a lot of firms are about to discover that their AI investments are multiplying the wrong thing.

    What to Do Monday Morning

    Pick three tasks in your firm that are repetitive, well-defined, and currently consume meaningful associate time. Document those tasks. Then pilot AI on them, with explicit human review at every step. Measure the time savings, the accuracy delta, and the reviewer experience. The pilot is the data. Once you have the data, you can decide whether to expand the use of AI on that task — and whether to expand it to other tasks of similar shape.

    Resist the temptation to deploy AI across the firm at once. The deployment that scales is the one that is preceded by a documented process and followed by measured results. The deployment that fails is the one that is announced before it is tested. There is enormous pressure inside firms right now to be seen to be using AI. The pressure is mostly cultural, not commercial, and it is causing firms to make commitments faster than their actual experience with the tools supports.

    And finally, decide explicitly what you will not let AI do. Write it down. Tell the team. The list is as important as the list of what you will let AI do, because the boundary is what protects the firm from the quiet failure mode. Firms with clear lines about what AI does and does not do produce reliable work with AI in the mix. Firms with fuzzy lines produce variable work and eventually a malpractice claim. The clear-line firm is the durable firm, and the durability is the point.

  • Qualified Offer Delivery: “Addressed To” vs “Delivered To”

    You’ve done everything right in working with the IRS and the IRS still got it wrong. You’ve exhausted your administrative remedies and you have to hire a tax attorney. Now you are incurring costs just to correct the IRS error. The attorney has you make a proper qualified offer under Section 7430(g) to recover attorneys… Continue reading Qualified Offer Delivery: “Addressed To” vs “Delivered To”

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  • Convert Interest Income to Capital Gains on Sales by Omitting Interest?

    Business transactions can be structured in any number of ways. Those who are tax savvy can structure their transactions to minimize and even avoid paying taxes. There are tax provisions that specifically allow for tax savings. To achieve the tax savings, one only has to structure the transaction to meet the requirements of the statute.… Continue reading Convert Interest Income to Capital Gains on Sales by Omitting Interest?

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  • Can the IRS Require Personal Information for a Business Tax Debt?

    You have a business entity. You took the time to form it. You made all of the tax filings. And then the business can’t pay its own tax liabilities. It owes the IRS back taxes. As you try to work with the IRS to resolve the balance, the IRS wants to know about your personal… Continue reading Can the IRS Require Personal Information for a Business Tax Debt?

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  • Churches, Families, and Private Inurement

    When you earn a dollar, you pay income tax and probably paid payroll or self-employment tax on it. When you spend what is left of the dollar after these taxes, you often pay a sales tax, property tax, or excise tax on the item purchased with the dollar. You may also pay an inflated price… Continue reading Churches, Families, and Private Inurement

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  • Decentralized by Design: Why We Hire Operators, Not Managers

    There is a recurring fiction in professional services about how firms get run. The fiction is that someone, somewhere, is making the decisions. A managing partner. A founder. A board. Pull on the thread long enough and you find that the decisions are actually being made by whoever happens to be in the room when the question comes up, and whoever can hold the floor longest. This is fine for a four-person firm. It does not scale. It also does not produce the kind of accountability that a serious organization runs on, because nobody can be held accountable for a decision they did not realize they were making.

    The serious version of the question — “who decides what?” — is the most important organizational question any platform of firms has to answer, and it has to be answered explicitly, in writing, with consequences attached. The platforms that answer it well end up running on something that looks like decentralization. The platforms that answer it badly end up running on something that looks like consensus, which is a form of decentralization that has no accountability attached and that produces neither the speed of centralization nor the local intelligence of true decentralization. The right answer is a third thing, and the third thing is what we have been trying to build.

    When we acquire a firm we replace the implicit decision-making with something different. Not centralization — the opposite. We push real authority down to the people closest to the work, and we make that authority specific enough that it is unambiguous who decides what. The result looks decentralized because it is decentralized. But it is decentralized by design, not by accident. Decentralization by accident is just chaos. Decentralization by design is a system, and a system is what allows a platform to scale without losing the local intelligence that makes the firms worth owning in the first place.

    Hire Operators, Not Managers

    The most common mistake we see in small professional services firms is hiring a manager when what the firm needed was an operator. A manager coordinates. An operator owns the result. A manager attends meetings about a problem. An operator solves the problem and then writes a one-paragraph memo about what was done. The skills look similar from the outside; the outcomes are not.

    We hire operators. We pay them like operators. We give them real budgets and real decision rights and we measure them against real outcomes. The trade-off is that operators are harder to find, harder to train, and harder to manage in the conventional sense — because the conventional sense of “manage” mostly means “review and approve,” and operators do not need that.

    The most reliable test for whether someone is an operator or a manager is to give her a problem and watch what happens in the first forty-eight hours. The operator goes and looks at the problem. She talks to the people involved. She forms a working hypothesis. She makes a small decision to test the hypothesis. By the end of the second day, the problem is either smaller or better understood. The manager, given the same problem, schedules a meeting. She circulates an agenda. She compiles a list of stakeholders. She writes a project plan. By the end of the second day, the problem is exactly the same size it was, but is now accompanied by a calendar invite. Both behaviors are defensible in the abstract. Only one of them produces movement, and movement is what we are paying for.

    The second-order consequence of hiring operators is that the holding company needs less of itself. An organization full of managers requires layers of oversight to coordinate the coordination. An organization full of operators requires a lean center whose primary job is to clear obstacles, allocate capital, and stay out of the way. The leaner center is cheaper, faster, and harder for the operators to resent — because the operators do not feel managed, they feel supported. That feeling is the difference between an operator who stays for ten years and an operator who leaves for someone who will give her the room she needed in the first place.

    Clear the Obstacles, Do Not Direct the Work

    Our role as the holding company is to clear obstacles. That sentence is short and easy to say, and most of what we do every day is figure out what it means in practice. It means we buy the practice management software the firm needs and could not afford alone. It means we hire the controller who lets the firm leader stop doing AR by herself. It means we negotiate the lease, the malpractice insurance, the bank line, the vendor contracts — everything that has nothing to do with serving clients.

    What it does not mean is telling the firm what work to take, how to price it, or which clients to fire. Those are the firm’s decisions. We are sometimes asked our opinion. We sometimes give it. But the decision is theirs and the result is theirs.

    The discipline of obstacle-clearing without direction is the hardest part of our job. The temptation to direct is constant, because direction is what holding companies traditionally do, because direction feels like value-add, and because direction lets the holding company executives feel like they are earning their pay. We resist the temptation because direction destroys the very thing we are paying the operators for. An operator who is being directed is not an operator anymore. She is a contractor with extra steps. The operator who runs her firm because we cleared her runway, and not because we gave her the playbook, is the operator who actually produces returns over a decade.

    Accountability Over Activity

    Most professional services firms are organized around activity. Billable hours, time entries, meetings attended, emails sent, documents drafted. None of these things are outcomes. None of them tell you whether the firm is actually getting better at the work. Reorganizing a firm around outcomes is harder than it sounds because almost every existing system — software, compensation, status hierarchy — reinforces activity.

    We measure firm leaders on a small number of things and we measure them honestly. Client outcomes. Client retention. Staff retention. Financial performance, but properly defined, not just revenue. The depth of the bench they are building. The state of the systems they inherited and are improving. That is the report card. Everything else is noise.

    The honest version of accountability is harder than the polite version. The polite version is “we have aligned on the metrics and we are tracking them together.” The honest version is “if these numbers are wrong for two years in a row, the firm leader will be replaced, and she knows it.” The polite version produces firm leaders who manage expectations. The honest version produces firm leaders who manage the firm. The first kind of accountability is theater; the second kind is architecture. Operators want the second kind, because they want to know what game they are playing and whether they are winning it. Managers prefer the first kind, because the theater protects them from being measured. The clarity of the honest version is part of why we are able to recruit the operators we recruit.

    Long Horizons

    Decentralization works only if the people you have decentralized to know they are going to be there long enough to live with the consequences of their decisions. Most professional services firms run on much shorter horizons than the work demands — quarterly hour targets, annual partner draws, three-year strategic plans that change every twelve months. The result is that the operators in those firms make decisions on the timescale of their reviews, not on the timescale of the firm.

    We are a permanent holder. We do not have a fund clock. We do not have a sponsor pressing for an exit. The firm leaders we hire know they are going to be running their firm five years from now, ten years from now, longer if they want it. That changes how they make decisions. They make better ones.

    The economic literature has been pointing at this for a long time, and the professional services industry has been ignoring it for almost as long. Short-horizon principals produce short-horizon agents, who produce short-horizon decisions, which compound into a portfolio of firms whose long-term value is significantly lower than the sum of their parts. Long-horizon principals do not have a magic touch — they just remove the pressure that forces operators to make decisions they know are wrong on a five-year view because they are right on a five-quarter view. The structural choice of being permanent capital is one of the highest-leverage choices a holding company can make. It changes nothing about any individual decision. It changes everything about the distribution of decisions over time. We have made that choice. It is the choice that, more than any other, is responsible for the kinds of firms we can build.

    What This Looks Like on a Random Tuesday

    The probate firm leader needs to decide whether to take on a complex litigated matter that will tie up two associates for six months. She does not need our permission. She does not ask for it. She decides, takes the case, and a week later sends a short note explaining the reasoning. We file it away. If the case goes badly, we will not second-guess the decision; we will look at what the firm learned. If it goes well, we will not take credit for it; we will look at what the firm learned.

    That is what decentralized leadership looks like in practice. It is not a slogan. It is a series of small, specific moments in which the person closest to the work decides, owns, and learns. We are betting that over time, a platform of firms run by operators who own their decisions outperforms a platform of firms run by managers who report on theirs. So far the bet is paying off.

    The cultural insight underneath this Tuesday is that ownership cannot be granted in theory and withheld in practice. Either the firm leader has the authority to take the matter or she does not. If the platform reserves the right to second-guess the decision after the fact, then the authority she has is conditional, and conditional authority is a kind of pseudo-authority that produces all the work of decision-making with none of the benefits. We have decided to give real authority and to accept the occasional bad decision that comes with real authority, because the alternative is to retain the right to micromanage and to receive, in exchange, firm leaders who behave like middle managers. The bad decision is bounded. The pseudo-authority is corrosive. The trade is obvious once you have lived on both sides of it.

    What to Do Monday Morning

    Write down, by role, who decides what. Do it in enough detail that there is no ambiguity. The firm leader decides on staffing, pricing, work selection, and local marketing. The platform decides on systems, capital allocation, and the leadership of the firm. The audit is the document. The document is the architecture. The architecture is what protects the decentralization from drifting back into the default centralization that every organization eventually slides toward.

    Hire operators, not managers, even when the resume of the manager looks more impressive. The manager will be easier to evaluate in the interview and harder to live with after. The operator will be harder to find, harder to read, and a better long-term bet. Train yourself, as a leader, to recognize the operator pattern in interviews — the bias for action, the comfort with incomplete information, the willingness to be wrong in writing.

    And finally, lengthen the horizons of the people you have decentralized to. If you cannot promise them that they will be there in five years, do not pretend you can decentralize to them in the meantime. Short-horizon decentralization is just an excuse to push hard decisions onto people who cannot afford to make them well. Long-horizon decentralization is what produces the firms that compound into something durable, and the durability is the entire point.

  • The Difference Between a Bad Business Investment and a Theft Loss

    Business ventures fail for countless reasons. Partners mismanage funds. Projects never materialize. Promises about how capital will be deployed go unfulfilled. When an investment goes south, the parties have to figure out how to minimize the damage. This often shifts the focus to how to benefit from the loss, which can warrant closer examination of… Continue reading The Difference Between a Bad Business Investment and a Theft Loss

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