Taylor TroeshModify

2026-06-09 08:00:00

tl;dr: If you earn considerable 1099 income in the US, report your business expenses to the IRS.

Federal Income Tax

Tariffs funded most US government spending until 1913.

The composition of US federal receipts, via census.gov and whitehouse.gov.

After the 16th Amendment legalized federal income tax, Congress levied it via the 1913 Revenue Act: a 1% income tax on high-earners (top ~2% of households).

Share of US households owing no federal income tax, via IRS SOI and Tax Policy Center.

To finance participation in World War I, the US expanded federal income taxation via the 1917 War Revenue Act. The government required entities to report income-like payments (i.e. interest, rent, dividends, wages) to the Bureau of Internal Revenue (which later became the IRS). The form for reporting such payments became known as Form 1099.

It goes like this:

1. Before paying a contractor, the payer collects a Form W-9 (personal information) from the payee.
2. Each tax season, the payer submits Form 1099 (payment history) to the IRS and the payee.
3. The payee reports their 1099 income on Form 1040 (individual income tax return) and sends the IRS a calculated portion of that income.

Effective federal income and payroll tax rate, via CBO, and Tax Policy Center. The average line aggregates the full payroll tax (employer and employee), but the median line only counts the employee share -- the gap reflects payroll incidence, not just progressive taxation.

To finance participation in World War II, the US expanded federal income taxation via the 1943 Current Tax Payment Act. This act required employers to withhold taxes from employee paychecks and send those funds directly to the government. Employers record the wages/withholdings on Form W-2, which employees report to the IRS via Form 1040 (individual income tax return).

All taxes (federal, state & local) as a share of GDP, via usgovernmentrevenue.com and OECD.

Nowadays, income is reported in many different flavors:

Meanwhile, self-employment is trending toward extinction. The modern wage economy swallowed self-governed farmers, artisans, shopkeepers, etc.

Independent vs wage-and-salary workers, via Lebergott/Census/BLS.

Contractors secure freedom at the cost of US employment protections (e.g. minimum wage, overtime pay, unemployment insurance, workers' compensation) and guarantees (e.g. workplace healthcare mandates).

Business Expenses

The original 1913 Revenue Act permitted business expense deductions. The 1918 Revenue Act refined these allowances for individuals:

All the ordinary and necessary expenses paid or incurred during the taxable year in carrying on any trade or business, including a reasonable allowance for salaries or other compensation for personal services actually rendered; and rentals or other payments required to be made as a condition to the continued use or possession, for purposes of the trade or business, of property to which the taxpayer has not taken or is not taking title or in which he has no equity.

The IRS adheres to the Internal Revenue Code (IRC), which codifies legislation (and court rulings) into enforceable statutes. The core of business expense deductions is defined in IRC §162:

There shall be allowed as a deduction all the ordinary and necessary expenses paid or incurred during the taxable year in carrying on any trade or business.

Let's break that sentence down:

• Ordinary: common and accepted in the trade or business, even if not habitual for the particular taxpayer. A once-in-a-lifetime lawsuit defending the business is ordinary; paying off someone else's bankrupt company's debts to burnish your own reputation is not.
• Necessary: "appropriate and helpful" to the business, not strictly indispensable.
• Paid or incurred during the taxable year: distinguishes deductible operating expenses from capital expenditures, which must be capitalized and depreciated over time. A $30 stapler is an operating expense you write off now; a $30,000 cargo van is a capital expenditure you recover over years (though §179 and bonus depreciation often let you expense it immediately anyway).
• Carrying on any trade or business: the activity must be a real, profit-motivated trade or business, not a hobby.

When you buy a long-lived asset (a van, a camera rig, a server rack), the IRS assumes it loses value gradually, so you deduct a slice of its cost each year over an IRS-defined "recovery period" (typically 3–7 years for equipment). In practice, §179 expensing and bonus depreciation let most small businesses skip the schedule and deduct the whole purchase in year one.

Business expenses are "above the line": they reduce your income before the standard deduction is applied. You need not itemize nor optimize -- qualified deductions stack atop the standard deduction that everyone receives.

Common deductions include:

• Home office: Rent/mortgage interest, utilities, insurance, depreciation. Part of the home must be used "regularly and exclusively" as the contractor's principal place of business. Two methods: the actual-expense method (calculated on Form 8829) and the simplified method (flat $5/ft² rate, up to 300 square feet, capped at $1,500 per year).
• Vehicle expenses: Contractors choose between the standard mileage rate (set by the IRS each year) and the actual-expense method (gas, oil, repairs, insurance, depreciation, lease payments × business-use percentage). The choice generally must be made in the vehicle's first year of business use; once actual expenses with accelerated depreciation are claimed, the standard rate is unavailable in later years.
• Equipment, supplies, and software: Computers, phones, tools, software subscriptions; longer-lived assets can often be expensed in full in the year of purchase or as bonus depreciation.
• Self-employment tax deduction: One-half of the contractor's 15.3% self-employment tax is deductible.
• Self-employed health insurance: Premiums for the contractor (and family) are deductible above the line (if not otherwise eligible for an employer plan).
• Retirement plan contributions: SEP-IRAs, Solo 401(k)s, and SIMPLE IRAs allow substantially higher tax-deferred contributions than ordinary IRAs, and the contributions reduce taxable self-employment income.
• Qualified Business Income (QBI) deduction: Most pass-through business owners may deduct up to 20% of qualified business income. QBI is your net business profit (1099 income minus expenses) excluding capital gains, interest, dividends, self-paid wages.
• Professional development: Continuing education and licensing fees that maintain or improve skills in the contractor's current trade are deductible; education that qualifies the contractor for a new trade is not.
• De minimis safe harbor: Tangible property up to $2,500 per item may be expensed immediately, no depreciation schedule required.
• Standard meal allowance: Instead of tracking actual meal costs while traveling, deduct the federal per-diem rate, which varies by location.
• Other: Advertising and marketing, professional fees (legal, accounting), bank and merchant-processing fees, business insurance, contract labor paid to subcontractors (may trigger a 1099-NEC filing obligation of your own), business meals (50% deductible), and travel away from home.

Things that are not business expenses:

• Personal expenses: the costs of being a person rather than a business: groceries, everyday clothing, rent on personal living space. Mixed-use items (a phone, a car, an internet plan) must be split by business percentage.
• Commuting from home to a regular place of business (even for contractors). The trip from a home office to a client site, by contrast, is generally deductible because the home office is the business location.
• Entertainment expenses: Client entertainment (sports tickets, concerts, golf outings) can not be deducted, even when business is discussed. Business meals remain 50% deductible.
• Fines and penalties: Parking tickets, speeding tickets, and government penalties are never deductible, even when incurred on business.
• Political contributions and lobbying: Campaign donations and lobbying costs are not deductible, even if the outcome affects your business.
• Capital expenditures: Must be depreciated, not immediately expensed.
• Unreimbursed employee business expenses: W-2 employees cannot deduct out-of-pocket work costs; the deductions in this essay belong to 1099 income on Schedule C.

Bookkeeping

Treasury Regulation §1.6001-1 requires taxpayers to document their tax liability. A complete transaction ledger generally contains (1) amount, (2) date, (3) place, (4) business purpose, and (5) the business relationship. These metadata are naturally recorded by receipts, bank/credit-card statements, invoices, etc.

If records are imperfect but a business expense was clearly incurred, the Cohan rule allows courts to estimate the deduction "bearing heavily, if it chooses, upon the taxpayer whose inexactitude is of his own making."

IRC §274(d) forbids estimation for heavily abused categories: travel, meals, gifts, and "listed property" (chiefly vehicles).

You don't need an LLC or a corporation to deduct expenses. Anyone who earns self-employment income is a sole proprietor by default. The structure only changes which form the income lands on (and how much paperwork you sign up for).

If you'd rather not share your Social Security number with every client, grab a free EIN from the IRS.

Most 1099 contractors are not bookkeepers (and do not want to be). To avoid forensic accounting headaches, isolate your payment methods. For example, you can issue single-purpose debit cards via Mercury.

If your bank does not offer virtual debit card services, you can create isolated debit cards by opening new bank accounts. You can open a business checking account at many banks with just a personal SSN. If business accounts aren't available, personal checking accounts work perfectly fine.

Some people prefer the simplicity of having one true balance; others prefer budgeting against isolated balances. If using multiple accounts, direct business income to your business account and pay yourself regular wages.

Credit cards achieve the same end. If you charge business transactions to one dedicated credit card, your monthly statements will contain only business expenses. Consider enabling autopay to avoid unintended credit card debt.

Remember that taxes are not automatically withheld from 1099 income. To avoid spending money owed to Uncle Sam, some contractors automatically redirect estimated taxes into an isolated high-yield savings account. Many clients are happy to send partial payments to two accounts, especially those who use direct deposit (ACH) services. If separate payments are not available, services like Mercury can be configured to automatically split income between accounts.

If you're looking for something more tailored/integrated, consider one of the many banking platforms for small businesses: Found, Lili, Novo, Relay, Bluevine, NorthOne, etc.

If you want even more control, modern bookkeeping software also connects directly to bank accounts and automatically imports/sorts transactions. Popular picks: QuickBooks Solopreneur, FreshBooks, Wave, Keeper, Xero, Expensify, etc.

In rare cases, you may need to record physical receipts. Digitize them immediately and throw them away. If the receipt-scanners in QuickBooks/FreshBooks/Expensify/etc. are insufficient, try dedicated apps like Dext and Shoeboxed.

Beware: thermal-paper receipts degrade over time. Never leave receipts in the sun.

Mileage is its own beast. If you are willing to share your live GPS location with corporations, consider apps like MileIQ, Stride, and Everlance.

Taxes are easy if you maintain good financial hygiene.

Tax Savings

When you make qualified investments into your business, the IRS will tax you as if you didn't earn that money.

Tax savings should be treated as a modest discount on business spending. Never excuse irresponsible spending because "it's a business expense".

Consider a single contractor with $100,000 of 1099 revenue and $15,000 of legitimate business expenses (tax year 2026, sole proprietor, no state income tax):

In this example, the federal government awards 30 cents for every business dollar; those dollars dodge self-employment tax and income tax and shrink your QBI base. Bookkeeping preserves 7.3% ($4,565) of the contractor's total income.

Spending proportionally more on your business yields larger percentage gains:

State taxes further increase these yields.

Income brackets (and spending habits) change these totals; the math is generally attractive to those who earn ~$60k+ per year. For those who earn (and spend) much more, a few hours of bookkeeping is the highest-paid work they'll do all year.

2026-05-25 08:00:00

Glossary

Currency

Currency in circulation — Federal Reserve notes and coin held outside the Treasury, Federal Reserve Banks, and depository institution vaults. Broken out by denomination ($100, $50, $20, etc.).

Deposits

Demand deposit — A bank account from which funds can be withdrawn on demand without prior notice (i.e., a checking account). Historically non-interest-bearing.

Household demand deposits — Checking-account balances held by individuals and nonprofits.

Business + government + foreign demand deposits — Checking-account balances held by nonfinancial corporations, state/local governments, and foreign entities at US banks. Excludes the Treasury's General Account at the Fed (which is not part of any M-aggregate).

Savings deposits — Interest-bearing accounts at depository institutions with no scheduled maturity. Includes passbook, statement, and online savings accounts.

Money market deposit account (MMDA) — A bank-issued, FDIC-insured deposit account that pays a money-market-like rate and allows limited withdrawals. Not the same as a money market fund.

Interest-bearing checking (NOW + ATS) — Checking accounts that pay interest, enabled by Negotiable Order of Withdrawal (NOW) accounts and Automatic Transfer Service (ATS) sweeps.

Time deposit — A deposit with a fixed maturity date and (usually) a penalty for early withdrawal. Certificates of deposit (CDs) are the most common form.

Small-denomination time deposit — A time deposit under $100,000 (a retail CD).

Large-denomination time deposit — A time deposit of $100,000 or more (an institutional or jumbo CD, often negotiable in the secondary market).

Money market funds

Money market fund (MMF) — A mutual fund that invests in short-term, high-quality debt and aims to maintain a stable $1 share price.

Retail vs. institutional MMF — Retail MMFs are open to households (lower minimums, individual share classes); institutional MMFs are restricted to corporations, pension funds, and other large investors.

Government MMF — An MMF that invests at least 99.5% in cash, Treasury securities, agency debt, and repos collateralized by those. The largest MMF category by assets.

Treasury-only MMF — A subset of government MMFs that hold only Treasury securities and Treasury repos.

Prime MMF — An MMF that invests in a broader range of short-term debt including commercial paper, large CDs, and corporate notes.

Tax-exempt MMF — An MMF that invests primarily in short-term municipal debt; interest is exempt from federal income tax.

Wholesale funding

Repurchase agreement (repo) — A short-term collateralized loan: the borrower sells a security and agrees to repurchase it later at a slightly higher price; the difference is interest. Treasuries are the most common collateral.

Tri-party repo — A repo where a custodian bank (e.g. BNY Mellon) handles collateral management for both sides. The dominant venue for general-collateral repo.

Bilateral repo — A repo arranged directly between two counterparties without a custodian.

FICC-cleared repo — A repo cleared through the Fixed Income Clearing Corporation, which steps in as central counterparty to reduce settlement risk.

Eurodollars — US dollar–denominated deposits held at banks outside the United States. The name predates the term being generic; today most are held in the Caribbean and London.

Treasury & corporate short-term debt

Treasury bill (T-bill) — US government debt with an original maturity of one year or less. Sold at a discount and redeemed at face value.

T-bill auction term — The original tenor at issuance (4-week, 8-week, 13-week, 17-week, 26-week, 52-week). When Treasury re-opens an existing CUSIP, the original auction term sticks — so a "26-week" bill four months later still appears in the 26-week bucket even though its remaining maturity is much shorter.

Cash management bill (CMB) — A T-bill with an irregular maturity (e.g., 14 or 35 days) issued ad-hoc when Treasury needs short-term cash.

Commercial paper (CP) — Unsecured short-term debt issued by corporations and financial institutions, typically maturing in under 270 days.

Financial CP — CP issued by banks, broker-dealers, and other financial firms.

Asset-backed CP (ABCP) — CP backed by a pool of assets (e.g., trade receivables, credit-card receivables, auto loans).

Nonfinancial CP — CP issued by nonfinancial corporations to fund payroll, inventory, and other working capital.

Savings bond (Series EE / I) — Non-marketable US government bonds sold directly to individual investors. Series EE pays a fixed rate; Series I pays a rate that adjusts every six months with inflation.

2026-05-19 08:00:00

For one week each Summer, my great grandma rented the same Newport Beach house for all our extended family to gather under one roof. Crying babies, drunk adults, religious disputes, sand everywhere, frequent injuries, potato salad, no parking -- it was pandemonium. Each day we somehow stuffed 80+ people in that 2-bedroom house. I miss those days.

That was long ago. Now I only attend ad-hoc (e.g. coffee) and/or obligatory (e.g. weddings) gatherings. I haven't seen my closest friends in years. I can't remember the last time I laughed/cried with them.

These were foreseen circumstances. My current lifestyle was composed of intentional choices: I got married, had a baby, then moved to a new city. I made decisions with tradeoffs, and my relationships inevitably change under such conditions. This is normal adulting stuff.

But conditions have changed again, and now I'm reaping the time/energy/money/trust dividends I've been sowing all these years. I'm so excited to reconnect with my friends.

Unfortunately, vacations require planning. As the self-appointed shit-disturber of my friend groups, I am responsible for such plans. To minimize planning and maximize pandemonium fun, I want to gather as many friends as possible together in the same spots each year.

The lazy/smart strategy is to coincide with established events. Here are some anchors that might work for me:

But my anchors are not your anchors. Your list should contain all your favorite events, people, places, and hobbies.

I'll obviously need to trim my list down a lot, but I thought it would be helpful to share some heuristics on how I choose events/places:

• I tend to abandon projects that require recurring work. If I want to see my friends regularly, I must prioritize convenience over cost/comfort/charm.
• My favorite anchors are charismatic friends with huge houses.
• I avoid giants like CES, but my friends are obligated to work at the event. You needn't attend an event to use it as an anchor; plan some meetups before/after the event.
• If my daughter attends scheduled programs (e.g. school), we might want to consolidate all family trips to school breaks, i.e. Summer, Spring break, Winter break. Even if she is homeschooled, she may want to visit friends who can only play during school breaks.
• 3-day weekends are double-edged swords. You and your friends skip work/school, but so does everybody else. The US becomes more expensive and crowded on those weekends.
• Camping is usually cheaper than hotel/AirBnB, but avoid major parks during busy seasons.

Don't overthink it. People like to do fun things together, again and again. Recurring experiences accrete into traditions. And with enough time, your traditions become their own anchors for future generations to inherit. Such things cannot be planned, nor can they happen without planning. Have fun.

2026-05-18 08:00:00

My grandma archives food. Her pantry contains foods which literally expired last millenium. She fills her freezer chests with unlabeled takeout containers, desserts from Trader Joe's, and half-full slush drinks from Starbucks/Costco/Jamba/etc. I am unsure whether to consult Marie Kondo, an archaeologist, or a priest.

True story: my wife once found a cat in her great aunt's refrigerator. They loved that cat but couldn't find the time to cremate its remains.

Today is May 18, 2026. This is the top of my ideas.txt file, where I store one project/essay/etc idea per line. It is 6,564 lines long. Entries like /scissor point to external files; I'm sitting on ~2MB of unpublished plaintext notes. I expect to die in ~4 decades.

I will never make a serious dent in this list, and that's not the point. It fulfills me to imagine, to curate, to tinker, and to sketch. Sometimes I even share my ugly little darlings with others.

Or that's what I tell myself. To publish my work is to admit "this is the best I can do". It's easier to hide my mediocrity in the freezer. "It's not a failure; I'm just not finished yet."

There is nothing wrong with being a chronic tinkerer nor a completionist. But it is difficult to be both. You cannot freeze your cake and eat it too.

There's a tradition of saving the top tier of a wedding cake and eating it on your first anniversary.

When I make wedding cakes, I'd rather they not have freezer-burned cake ruining their memory. I promise them a duplicate of the top tier on their anniversary.

One pair of friends froze it anyway. And… six years later, after the divorce, we pulled it out of the freezer. It was perfect; the fresh raspberries in the filling looked like they were picked yesterday.

Maybe it's because it was a fondant-covered cake. I don't usually do fondant, because as pretty as it is, nobody wants to eat it. It seemed appropriate for this couple, though in retrospect maybe that should have been a sign.

-- jfengel

2026-05-08 08:00:00

tl;dr: Try out telecast.company; share your complaints/gripes on GitHub.

2005 birthed the iPod Video and YouTube.

20 years later… it's 2025. Compare YouTube against the podcast (iPod broadcast) ecosystem. YouTube pisses off its creators, fuels a clickbait thumbnail arms-race, and fosters addiction (protip: disable recommendations). Podcasters thrive in an ecosystem of interviews, educational content, and long-form journalism.

Okay, this is a bit unfair. Trash podcasts exist. Quality YouTube channels exist (and are strafing over to Nebula). Incentives tend to produce different median media on their platforms; YouTube's centralized advertising model seems to encourage unsustainable behavior from its advertisers, its creators, and its consumers.

Yes, video podcasts have been a thing since 2005, but YouTube dominated online video by simplifying hosting/delivery/discovery. Twenty years later, creating/consuming video podcasts remains an awful experience.

"vidcast" and "vodcast" are clunky portmanteaus, so I'm co-opting the term "telecast" (television broadcast) for video podcasts.

Proof-of-Concept

And so I built a very crappy video podcast player.

Some initial features/findings:

• I first tried VanJS, but ended up using Elm. Elm is handy for medium-sized projects like this!
• podcastindex.org is a great resource for jumpstarting podcast search! Unfortunately, it doesn't provide any easy means of exclusively searching video podcasts/episodes, so I'll likely have to build my own directory from scratch.
• Podcasts apparently support live broadcasts!
• YouTube already already exposes an RSS feed for every channel! But searching/browsing YouTube channels will impede telecast adoption.
• I eventually want to facilitate creator donations, but web monetization is not quite there yet.
• The loading times for thumbnails was prohibitively slow for many podcast feeds.
• Full local-first will not be feasible with limited browser storage, but it will ease the transition to native apps
• The app looks way too empty/intimidating on first load. I'll want to create some curated starter packs.

Throw One Away

That prototype was too crappy. I tossed it in the proverbial garbage.

"Throw One Away" is my favorite way of acclimating to a new problem domain.

Here's what it looks like now:

It's designed to be local-first software; nearly everything lives in the frontend. The only server endpoints are (1) a public search API and (2) a CORS/cache proxy for RSS feeds and video thumbnails.

I used duckdb and some nasty sql to load the search database with ~100K feeds from PodcastIndex.org.

curl -O https://public.podcastindex.org/podcastindex_feeds.db.tgz
tar -xzf podcastindex_feeds.db.tgz -C /tmp/
sed "s|\$DATABASE_URL|$DATABASE_URL|" import_feeds.sql | duckdb

Thanks to PodcastIndex.org for helping make the internet open, free, and accessible!

Beyond video podcasts, I also added a bunch of my favorite RSS feeds from YouTube, plus channels from Kagi's smallyt.txt list.

The code is on Github. It's crappy, but it's mine -- I'm tired of smelling other people's crap.

Try it out at telecast.company

2026-04-08 08:00:00