May 20, 2026

The Hedge · May 20, 2026 · Brutal Honesty Over Hype Since 2008

Copyright law was built on two assumptions: that expression is scarce, and that copying is detectable. AI has demolished both — and the legal system has no clean answer for what comes next.

A model can now ingest a novel, internalize its structure, voice, and ideas, then produce something functionally equivalent without reproducing a single protected sentence. That’s not a loophole. That’s a structural failure in the entire framework.

The cases on the docket

The litigation now working through the system — the NYT’s suit against OpenAI, the Authors Guild actions, Getty Images versus Stability AI — isn’t really about copying in the old sense. The central questions are whether training on copyrighted work constitutes infringement, and whether AI output competes with the original in the marketplace.

That second prong is where fair use gets complicated fast. The four-factor test has always weighted “market harm” heavily. If AI output replaces demand for the original, the “transformative use” defense takes serious damage — no matter how technically different the output is.

“Fair use was designed for humans doing creative work. An AI processing 100 billion tokens of human writing to produce commercial output doesn’t fit that mold — and courts know it.”

Where the doctrine breaks down

Fair use was designed for humans with expressive intent: a critic quoting a passage, a scholar analyzing a text, a parody riffing on an original. The doctrine assumes a person on the other end. That assumption is gone.

Courts will have to either stretch the doctrine until it’s unrecognizable, or acknowledge it simply doesn’t apply the same way. Neither path is clean.

The rewrite problem

Here’s the sharper issue: if AI can take any copyrighted work and produce a “better” version — cleaner prose, updated facts, same ideas — what exactly does copyright protect anymore?

Under current law: expression, not ideas. You can’t copyright a plot structure, a chord progression concept, or a journalistic angle. You can only copyright the specific words, notes, or images. A perfect paraphrase has always been legal. AI just industrializes it at a scale that makes the distinction feel hollow — because it is hollow, at that scale.

How this likely resolves

Four scenarios are on the table:

1. Licensing regimes emerge. Like ASCAP/BMI for music — a collective licensing system for training data. Publishers get a cut, AI companies get legal cover. Messy but workable. Probably the most likely near-term outcome.
2. Output rights get carved out. Courts hold that training is fair use, but AI output that directly substitutes for source material is not. Creates a two-tier system that will be a nightmare to enforce.
3. Congress acts. Probably the least likely near-term outcome given how slowly IP law moves. But pressure is building, and there’s bipartisan motivation when the targets are both large tech companies and foreign competitors.
4. Fair use expands and copyright atrophies. Courts decide transformation is so complete that most AI use qualifies, effectively gutting enforcement for a generation. Unlikely — but not impossible if lobbying balance tips hard enough.

The honest bottom line

Copyright was a bargain: society grants temporary monopoly rights to creators in exchange for eventual public domain contribution. AI breaks that bargain in both directions.

It learned from centuries of creative work without compensating anyone. It now produces work that may never need to enter the creative ecosystem at all. The legal system will patch something together — but it won’t be intellectually coherent. It’ll be whatever compromise the most powerful parties can negotiate.

The writers, photographers, and musicians are going to get something — probably not enough. The AI companies are going to pay something — probably not enough. That’s how these things usually resolve.

The people who built the internet learned this the hard way. Creators are learning it now.

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The Hedge has covered financial and legal disruption since 2008. Brutal honesty over hype — always.

The Hedge | Brutal Honesty Over Hype Since 2008

The S-corporation is one of the most common business structures for small businesses across the country — a pass-through entity that avoids corporate double-taxation while providing payroll tax savings for profitable businesses. In California, the S-corporation calculus is different from most states because California imposes an additional 1.5% tax on S-corporation net income that doesn’t apply to LLCs or sole proprietorships. Understanding when the S-corporation structure helps and when it hurts in California requires running the specific numbers for your situation.

How S-Corporations Save on Payroll Taxes

In a sole proprietorship or single-member LLC, all net business income is subject to self-employment tax — 15.3% on the first $168,600 (2024) and 2.9% on amounts above that. An owner-operator generating $200,000 in net income from a sole proprietorship pays approximately $27,000 in self-employment tax in addition to income tax.

An S-corporation allows the owner-operator to split their compensation between a “reasonable salary” — subject to payroll taxes — and a distribution — not subject to payroll taxes. An S-corp owner generating $200,000 in net business income who pays herself a reasonable salary of $100,000 (subject to payroll taxes) and takes the remaining $100,000 as a distribution (not subject to payroll taxes) saves approximately $13,500 in federal self-employment tax relative to the sole proprietorship structure.

The California S-Corp Tax Complication

California imposes a 1.5% tax on S-corporation net income — the “built-in gains tax” equivalent that partially offsets the federal payroll tax savings. On $200,000 in S-corp net income, the California S-corp tax is $3,000. This partially reduces the federal payroll tax savings but doesn’t eliminate them — the net benefit of S-corp election in California is still positive for most businesses generating more than approximately $40,000–$50,000 in net income annually.

The S-corp tax is calculated on net income after deducting the reasonable salary. An S-corp paying its owner a $100,000 salary and generating $200,000 in total income has net S-corp income of $100,000, generating a California S-corp tax of $1,500. The comparison against the LLC’s $800 minimum franchise tax (or the gross receipts-based LLC fee for larger companies) requires specific calculation for your income level.

The S-Corporation Conversion

California LLCs can elect S-corporation treatment for federal tax purposes by filing IRS Form 2553. The California S-corp election is generally made simultaneously. This conversion does not require forming a new corporation — the LLC remains an LLC for state law purposes while being treated as an S-corporation for federal and California income tax purposes. This “LLC taxed as S-corp” structure has become increasingly common for California small businesses because it combines the liability and operational flexibility of an LLC with the payroll tax advantages of S-corp treatment.

The practical considerations: S-corp status requires maintaining a payroll for the owner (including payroll tax filings, withholding, and W-2 production), keeping S-corp distributions separate from salary, and ensuring that shareholder eligibility requirements are met (no more than 100 shareholders, all shareholders must be U.S. citizens or residents, only one class of stock). Run the specific numbers for your income level with a California CPA before making the election.

The Hedge has been cutting through financial and business noise since 2008. Brutal honesty over hype — always.

The Hedge | Brutal Honesty Over Hype Since 2008

The sale of a California business is one of the most significant financial events in an entrepreneur’s life — and California’s tax treatment of business sale proceeds is one of the most punishing in the country. Founders who spend years building their businesses without thinking about exit tax planning routinely discover at closing that California will claim a large share of what they’ve earned. Pre-exit tax planning, done well in advance of a sale, can significantly reduce this burden. Done after the letter of intent is signed, your options narrow substantially.

California’s Capital Gains Treatment

California taxes long-term capital gains at ordinary income rates — there is no preferential capital gains rate in California, unlike the federal system which taxes long-term gains at 15% or 20% for most taxpayers. California’s top individual income tax rate of 13.3% applies to capital gains from the sale of a California business, regardless of how long you held it. On a $5 million gain from the sale of a California company, California income tax is approximately $665,000 — a substantial sum that would be $0 for the identical transaction executed by a Texas-based founder.

The California Residency Test

California taxes the capital gains of California residents on all their income, regardless of where the income is earned. A California resident who sells a California company, a Texas company, or a company incorporated in Delaware pays California income tax on the gain — California’s reach follows residency, not business location. California’s definition of residency is broad: a person who is in California other than for temporary or transitory purposes is a California resident for tax purposes. Part-year residents are taxed on California income during the residency period plus all income for the portion of the year they were California residents.

Pre-Exit Residency Change: The Most Powerful Strategy

For founders who are genuinely willing to leave California before a business sale, establishing residency in a no-income-tax state — Texas, Nevada, Florida, Wyoming — before the gain is recognized can eliminate California income tax on the sale proceeds. But California’s FTB aggressively challenges residency changes that appear to be motivated primarily by tax avoidance. A genuine residency change requires actually living in the new state, changing domicile, establishing new professional and personal ties, and being prepared to demonstrate that the change was genuine and not a temporary maneuver. Founders who change residency in November and sell their business in January face intense FTB scrutiny. Genuine residency changes typically require 12-24 months of establishing the new domicile before the sale to withstand FTB challenge.

Asset vs. Stock Sale Structure

The structure of a business sale — whether the buyer purchases the business’s assets or the seller’s stock — has significant California tax implications. Asset sales generally produce ordinary income for certain asset categories (inventory, accounts receivable, depreciation recapture) and capital gain for others (goodwill, going concern value). Stock sales generally produce capital gain on the entire proceeds. The California tax treatment of each structure should be analyzed by a qualified tax attorney before any deal structure is agreed upon — changing the structure after the letter of intent is signed is possible but complicated.

The Hedge has been cutting through financial and business noise since 2008. Brutal honesty over hype — always.

The Hedge | Brutal Honesty Over Hype Since 2008

For many California small business owners, the choice between operating as an LLC taxed as a sole proprietorship or partnership versus electing S-corporation tax treatment is worth tens of thousands of dollars annually in self-employment tax savings. This is not a commonly understood planning opportunity — most small business owners either default to their formation document’s default tax treatment or choose based on incomplete information. Understanding the S-corporation election in the California context can meaningfully change your annual tax bill.

The Self-Employment Tax Problem

Sole proprietors and single-member LLC owners who haven’t made an S-corp election pay self-employment tax — the combined employee and employer share of Social Security and Medicare — on their entire net business income. At 15.3% on the first $160,200 of net self-employment income and 2.9% (for Medicare) above that threshold, self-employment tax is a substantial cost that comes on top of federal and California income taxes. A California business owner with $200,000 in net business income pays approximately $28,000 in self-employment tax before any income tax.

How the S-Corporation Election Helps

When an LLC elects to be taxed as an S-corporation (by filing IRS Form 2553), the business owner becomes both an owner and an employee of the company. The owner must receive a “reasonable salary” for their services — subject to payroll taxes — but the remaining business profit passes through as a distribution that is NOT subject to self-employment tax. This salary/distribution split reduces the self-employment tax base, potentially saving thousands of dollars annually.

Example: A business owner with $200,000 in net business income sets a reasonable salary of $80,000. They pay payroll taxes (15.3%) on $80,000 = $12,240. The remaining $120,000 passes as a distribution subject to income tax but not self-employment tax — saving approximately $10,000 to $14,000 in self-employment tax relative to the non-election structure. The savings must be weighed against the additional payroll processing costs and accounting complexity of running payroll, which typically run $2,000 to $4,000 per year. Net savings: typically $6,000 to $12,000 annually at the $200,000 income level.

The California Complication

California adds a specific wrinkle: California does not conform to federal S-corporation treatment in all respects. California imposes a 1.5% franchise tax on S-corporation net income (with a minimum of $800), and California LLCs that elect S-corporation treatment still owe the LLC fee on gross receipts. The California-specific analysis sometimes produces different results than the federal analysis — occasionally making the S-corp election less advantageous in California than it would be in a zero-income-tax state.

Running this analysis correctly requires a California CPA who understands both the federal S-corp rules and California’s nonconformity. The election, once made, can be difficult to revoke. Making it without a proper California-specific analysis is a mistake that some business owners discover only when their California tax bill is higher than expected.

When the S-Corp Election Makes Sense

The S-corp election generally makes sense for California LLCs when: net business income consistently exceeds $80,000 to $100,000 per year; the owner actively participates in the business and can justify a reasonable salary that is meaningfully below total profit; the business has stable, predictable income that makes payroll processing manageable; and the California-specific analysis confirms that the federal self-employment tax savings exceed the California franchise tax cost of the election.

The Hedge has been cutting through financial and business noise since 2008. Brutal honesty over hype — always.

The Hedge | Brutal Honesty Over Hype Since 2008

California Labor Code Section 2802 requires employers to reimburse employees for all necessary expenditures incurred in the discharge of their duties. This sounds straightforward. In practice, it’s a compliance minefield that generates significant PAGA litigation, creates unexpected costs for employers who haven’t budgeted for it, and extends to expense categories that most employers don’t think about as reimbursable — particularly in a remote work environment.

What Must Be Reimbursed

The California reimbursement obligation covers: business travel expenses (mileage at the IRS rate, airfare, lodging, meals when traveling for work); work-related supplies and equipment purchased by employees; professional dues, licenses, and subscriptions required for the job; home office expenses for remote workers — and this is the category that surprises most employers: cell phone expenses when employees use their personal phones for work; and internet service when employees work from home. The obligation is broad, non-waivable (employees cannot contract away their Section 2802 rights), and applies even if the employee chooses to incur the expense voluntarily.

The Remote Work Reimbursement Expansion

The remote work era significantly expanded Section 2802’s practical scope. An employee working from home uses their personal internet connection for work purposes — California courts and the DLSE have consistently held that this creates a partial reimbursement obligation. The employee’s home electricity usage increases when they work from home — there’s a reasonable argument that a portion of the electricity bill is reimbursable. The employee uses their personal cell phone for work calls and emails — definitely reimbursable under established California law.

Most California employers with remote workers have not established systematic reimbursement programs for these expenses. Many have learned about the obligation through PAGA demand letters rather than proactive compliance planning. Each unreimbursed expense is a Labor Code violation. With PAGA penalties of $100 per employee per pay period for initial violations, a two-year lookback period, and 50 remote employees each spending $50-$100 per month on reimbursable expenses, the exposure is substantial.

The Practical Compliance Approach

The most common compliant approach to cell phone and internet reimbursement is a fixed monthly stipend that represents a reasonable approximation of the work-related portion of the expense. For cell phones, a stipend of $30-$50 per month is typically defensible for employees who use their personal phones for work. For home internet, $25-$50 per month covers the incremental work-related portion in most scenarios. A written policy documenting the stipend program, the employer’s acknowledgment of the reimbursement obligation, and the methodology for calculating the stipend is essential.

For mileage, use the IRS standard mileage rate (currently $0.67 per mile) for all business miles driven. For other expenses, require receipts and document business purpose. The administrative cost of a compliant reimbursement program is modest. The cost of discovering the obligation through litigation is not.

The Hedge has been cutting through financial and business noise since 2008. Brutal honesty over hype — always.

The Hedge | Brutal Honesty Over Hype Since 2008

For most entrepreneurs, the business exit — the sale, the IPO, the merger — is the event they’ve been building toward. In California, that event has state tax consequences that are among the most severe in the country. Understanding how California taxes business exits before you commit to building in California is essential planning, not optional afterthought.

California’s Capital Gains Treatment

California does not offer preferential tax rates for long-term capital gains. While the federal system taxes long-term capital gains (assets held more than one year) at rates of 0%, 15%, or 20% depending on income, California taxes capital gains at the same rates as ordinary income — up to 13.3% for incomes above approximately $1 million. This means a California founder selling a company after ten years of work pays California income tax at the same rate as wages earned last month. There is no holding period benefit.

On a business sale that generates $5 million in capital gain, the California tax is approximately $665,000 — on top of federal capital gains tax of approximately $750,000 for a founder in the top federal bracket. The combined federal and California tax burden on a $5 million gain is approximately $1.4 million, leaving the founder with approximately $3.6 million after tax. The identical transaction for a Texas founder produces no state capital gains tax — leaving approximately $4.25 million after federal tax alone. The California founder pays approximately $665,000 more on the same exit.

The Residency Timing Strategy

California’s capital gains tax can be significantly reduced or eliminated if the founder establishes genuine residency in a no-income-tax state before the taxable event occurs. The key word is “genuine” — California’s Franchise Tax Board is sophisticated about residency changes motivated by tax avoidance and aggressively audits founders who claim to have left California shortly before a significant liquidity event.

What constitutes genuine California residency termination: physical relocation to the new state, updating driver’s license and voter registration, changing primary banking relationships, transferring vehicle registration, joining local community organizations, and — most importantly — actually spending the majority of time in the new state rather than California. Founders who move to Nevada or Texas on paper while continuing to operate their business from a California office and spending most nights in a California home are still California residents for tax purposes.

Qualified Small Business Stock (QSBS) — The Federal Offset

Section 1202 of the Internal Revenue Code provides a federal exclusion of up to $10 million (or 10x the taxpayer’s basis) in capital gains from the sale of Qualified Small Business Stock — stock in a domestic C-corporation with gross assets under $50 million at the time of issuance, held for more than five years. California conforms to this exclusion for sales after 2013, with some limitations. For founders who have properly structured their company as a Delaware or California C-corporation and meet the QSBS requirements, the combined federal and California tax savings can be substantial.

QSBS qualification requires careful attention to corporate form, asset thresholds, and holding period. It is worth a dedicated analysis with a California tax attorney early in the company’s life — not at the time of exit when the planning window has closed. The compliance cost of maintaining QSBS eligibility is minimal; the tax savings on a qualifying exit can be millions of dollars.

The Hedge has been cutting through financial and business noise since 2008. Brutal honesty over hype — always.

The Hedge | Brutal Honesty Over Hype Since 2008

California’s tax enforcement agencies — the Franchise Tax Board (FTB) for income and franchise taxes, and the Employment Development Department (EDD) for payroll taxes and employment status — conduct audits of California businesses with enough frequency that every California entrepreneur should understand what triggers them, how they proceed, and what good preparation looks like. Being audited in California is expensive and time-consuming even when you’ve done nothing wrong. Being audited when you have compliance gaps is potentially devastating.

What Triggers FTB Audits

The FTB uses a combination of automated screening and targeted audit selection. Automated red flags include: large discrepancies between federal income (reported on Form 1040) and California income (reported on California Form 540); significant deductions that are unusual for your income level or business type; California-source income without corresponding California tax filing; business losses that continue for multiple years; and transactions with related parties that may not reflect arm’s-length pricing. Targeted selection focuses on specific industries, specific compliance issues the FTB has identified as systemic problems, and referrals from other agencies or the IRS.

What Triggers EDD Audits

The EDD conducts audits specifically focused on payroll tax compliance and worker classification. EDD audits are frequently triggered by: former workers who file for unemployment insurance after being classified as independent contractors (triggering an EDD review of whether they should have been employees); complaints from current or former workers about misclassification; referrals from the Labor Commissioner following wage claims; and systematic selection of industries where contractor misclassification is known to be prevalent (construction, technology staffing, entertainment production, gig economy companies).

The AB5 Audit Risk

AB5’s expansion of the ABC test for contractor classification has significantly increased EDD audit risk for California companies that use contractors. Companies that relied on contractor classifications that were legally defensible before AB5 may find those same arrangements subject to reclassification under AB5’s stricter standards. An EDD audit that results in reclassifying contractors as employees can produce assessments of back payroll taxes, interest, and penalties reaching years into the past — a retrospective liability that can be significant for any company with meaningful contractor usage.

Audit Preparation

The best audit preparation is year-round compliance: accurate and contemporaneous record-keeping, properly classified workers with documented classification analysis, wages and salaries supported by written agreements, business expense deductions supported by receipts and business purpose documentation, and complete and timely tax filings. When an audit notice arrives, engage a California tax attorney or CPA with audit experience before responding to anything. The initial audit notice often requests records — how you respond to that initial request shapes the entire audit process. Don’t navigate a California tax audit without professional representation.

The Hedge has been cutting through financial and business noise since 2008. Brutal honesty over hype — always.