Articles
Plain-English guides to the tax and finance decisions small business owners actually face.
1099-NEC Filing Requirements: Who Gets One, When It's Due, and What Happens If You Miss It
Businesses must issue a 1099-NEC to every contractor paid $600 or more in a year. The January 31 deadline is firm, penalties are tiered, and collecting W-9s before payment is the system that works.
Business setupThe 30-Day Business Setup Checklist: What to Do Before Your First Dollar
A week-by-week action plan for new business owners — EIN, business bank account, bookkeeping software, tax savings habit, quarterly estimates, insurance, and the one conversation you should have with a CPA before you get busy.
S-corp planningThe S-Corp Accountable Plan: Reimburse Yourself Tax-Free for Business Expenses
S-corp owners can't deduct unreimbursed employee expenses on their personal return. An Accountable Plan lets the corporation reimburse you for home office, vehicle, phone, and other expenses — tax-free to you, deductible by the corporation.
BookkeepingAccrual vs Cash Basis Accounting: Which Method Should Your Business Use?
Cash basis recognizes income when received and expenses when paid — deferring taxes and staying simple. Accrual recognizes income when earned. Most small businesses can and should use cash basis. Year-end timing strategies that only work on cash basis.
Tax planningAlternative Minimum Tax (AMT): When Business Owners and Option Holders Get Caught
The AMT is a parallel tax system with different rules. Business owners encounter it through ISO stock option exercises, depreciation preferences, and high income. The ISO AMT trap, how the AMT credit works, and why you need to model it before year-end.
Deal structureAsset Sale vs Stock Sale: What Business Owners Actually Pay
A plain-English comparison of how each structure taxes the same exit — and why buyers and sellers usually want opposite things.
Tax strategyThe Augusta Rule: What It Is, What It Actually Requires, and How to Do It Right
Section 280A(g) lets you rent your home to your S-corp for up to 14 days per year — tax-free rental income, business deduction for the entity. Here's what the rule actually requires.
Tax planningBackdoor Roth IRA: How High-Income Earners Get Money Into a Roth
High earners above the Roth IRA income limit can contribute via the backdoor — contribute nondeductibly to a traditional IRA, then immediately convert to Roth. The pro-rata trap, how to avoid it, and the mega backdoor Roth for up to $46,500/year.
BookkeepingWhich Bookkeeping Software Should You Use? Wave, QuickBooks, Xero, and FreshBooks Compared
A plain-English comparison of the most common bookkeeping tools for small business owners — which one fits your business type, what each costs, and the one mistake to avoid when setting up.
BookkeepingBusiness Expense Categories: What to Track and How to Enter It in QuickBooks or Xero
The most common expense categories, QuickBooks and Xero names, and the special rules for auto, meals, and home office.
InsuranceBusiness Insurance: What Coverage Types Actually Apply to Your Business
General liability, professional liability, workers comp, commercial property, business interruption, cyber, commercial auto, key-person — what each type covers, when it actually matters, and which ones small businesses most often skip when they shouldn't.
Tax deductionsBusiness Meals Deduction: What's 50%, What's 100%, and What's Gone
Entertainment expenses are no longer deductible after TCJA 2017. Business meals are still 50% deductible — when there's a genuine business purpose and documentation. What qualifies, what doesn't, and what documentation the IRS requires.
Tax deductionsCell Phone and Internet Deductions for Self-Employed Business Owners
Self-employed owners deduct the business-use percentage of their cell phone and internet. S-corp owners must use an Accountable Plan — TCJA eliminated the unreimbursed employee expense deduction. How to document usage and determine a defensible percentage.
Tax deductionsBusiness Travel Deduction: What Qualifies, What Doesn't, and How to Document It
Business travel is deductible when the primary purpose is business — but the rules differ for domestic vs international trips, mixing business with personal travel, and whether you can bring a spouse.
Business deductionsBusiness Travel Tax Deductions: The Rules That Actually Apply
Adding personal days to a business trip is often less costly than you think — airfare is all-or-nothing based on primary purpose. Here's how the IRS rules work.
S-corp planningC-Corp vs S-Corp: When the 21% Flat Rate Beats Pass-Through Taxation
Most profitable small businesses choose S-corp. But a C-corp's flat 21% rate — combined with retained earnings, fringe benefits, and the Section 1202 QSBS gain exclusion — can produce a better outcome in specific situations.
Entity structureCalifornia LLC vs. S-Corp: The True Cost Comparison
In California, the S-corp pays 1.5% franchise tax on net income instead of the flat $800 LLC fee. Here's when the S-corp still wins — and when it doesn't.
California taxCalifornia's Pass-Through Entity Tax Election: How S-Corps and Partnerships Bypass the SALT Cap
The AB 150 PTET election lets California S-corps and partnerships pay state income tax at the entity level — making it federally deductible and effectively bypassing the $10,000 SALT cap. How it works and when to elect.
California taxesCalifornia Quarterly Estimated Tax Schedule: Why It's Different from Federal
California's quarterly schedule is 30% in April, 40% in June, nothing in September, and 30% in January — not the federal 25/25/25/25. Using the wrong one means penalties.
Sales taxAre Resale Purchases Exempt From Sales Tax in California?
How CDTFA-230 resale certificates work, when to use one, and the real consequences of misuse.
State taxCalifornia Tax When Selling a Business: What Owners Should Know
How California treats the gain on a business sale, what residency really requires, and where planning still moves the number.
Tax deductionsCan I Deduct My Car as a Business Expense?
Yes — but only the business portion. Here's how the two methods work, what actually qualifies as business mileage, why your commute doesn't count, and what the IRS wants to see.
Tax planningCapital Gains Tax Rates: Long-Term vs Short-Term, State Tax, and the NIIT Surcharge
Long-term gains are taxed at 0%, 15%, or 20% federally. Short-term gains are ordinary income. Add California's 13.3% and the 3.8% NIIT, and California business owners face effective rates above 37% on long-term gains — and above 54% on short-term.
Tax planningCharitable Giving for Business Owners: DAFs, Appreciated Stock, and Where the Deduction Goes
Pass-through owners deduct charitable contributions on Schedule A — not the business return. Donating appreciated stock avoids capital gains and maximizes deductions. Donor-Advised Funds, the bunching strategy, and the Qualified Charitable Distribution for IRA owners.
BookkeepingChart of Accounts Explained: The Financial Filing Cabinet for Your Business
What a chart of accounts is, what the five account types mean, and sample charts for a service business and a product-based business.
Equity compensationConcentrated Stock Positions: Five Strategies for the Exec Sitting on a Large Holding
Selling triggers full capital gains. Holding means concentration risk. There are five strategies in between — each with different tax, liquidity, and coordination requirements.
InsuranceCoordinating Insurance with Your Tax and Wealth Plan
Insurance decisions have direct tax consequences — the self-employed health insurance deduction, S-corp health on the W-2, HSA contributions, key-person and buy-sell life premium treatment, disability premium-vs-benefit taxability. How to coordinate the broker, CPA, and advisor so the decisions don't get made in silos.
Tax planningDefined Benefit and Cash Balance Plans: The High-Income Owner's $200,000+ Deduction
Solo 401(k) contributions cap out around $70,000. A cash balance plan can let a profitable business owner deduct $150,000 to $350,000 per year — dramatically lowering current-year tax bills while building a guaranteed retirement benefit.
Tax planningDepreciation Recapture: Why Selling Business Assets Costs More Than You Expect
When you sell a depreciated business asset, the IRS recaptures those deductions — taxing the gain up to the amount of depreciation taken at ordinary income rates. Section 1245 vs Section 1250, the impact of bonus depreciation, and how recapture affects business sales.
Business structureDo I Actually Need an LLC?
An honest answer to the question every new business owner asks. What an LLC actually protects, when it matters, when it doesn't, and what to do if you're not sure.
BookkeepingDoes Every Business Transaction Need to Be Accounted For?
Yes — and not every transaction is an expense. How to categorize correctly so your books actually tell you something useful.
Tax deductionsEducation and Professional Development Deductions for Self-Employed Owners
Education that maintains or improves skills in your current trade is deductible. Education that qualifies you for a new career is not. What qualifies, how conferences and travel costs work, and how S-corp owners should handle it through an Accountable Plan.
Business operationsDoes Hiring This Person Actually Pencil Out?
The fully loaded cost of an employee vs. the salary number — employer FICA, FUTA, SUTA, workers comp, benefits, and the revenue math behind whether a hire breaks even.
Business operationsEmployee vs Independent Contractor: How the IRS Classifies Workers and the Cost of Getting It Wrong
Classifying a worker as a contractor when the IRS considers them an employee creates substantial liability — back payroll taxes, penalties, and interest going back years. The IRS three-category test, California's ABC test, and how to protect yourself.
AllocationGoodwill and the Tax on Selling a Business
Personal vs enterprise goodwill, why the allocation matters, and how it shows up on the final tax bill.
1099 formsI Got a 1099 — What Do I Do With It?
A 1099 is just a report. It means someone told the IRS they paid you. Here's what the different kinds mean, what to do with them, and what happens if the number is wrong.
IRS noticesI Got an IRS Notice — Here's What to Actually Do
Most IRS notices are not emergencies. Here's what the common ones mean, what requires action, what you can ignore, and the one thing you should never do.
Tax strategyPaying Your Children Through Your Business: The Tax Strategy That Actually Works
Children employed by a parent's sole prop pay no FICA on their wages. The income shifts from your high bracket to their near-zero bracket. Here's what makes it defensible.
Tax planningHiring Your Children or Spouse in Your Business: The Tax Benefits and the Rules
Business owners can hire their children and shift income to a lower tax bracket — and children under 18 working in a parent's sole proprietorship avoid FICA and FUTA entirely. Real work, reasonable wages, and documentation are required.
Business operationsHiring Your First Employee: The Compliance Checklist Most Owners Skip
A step-by-step guide to the actual legal and tax obligations when you hire your first W-2 employee — I-9, new hire reporting, workers comp, payroll setup, and what to do in the first week.
Tax deductionsThe Home Office Deduction: Who Qualifies, How to Calculate It, and Which Method Saves More
Self-employed business owners can deduct the business-use portion of their home — but only if it meets the exclusive-use test. Simplified vs actual method, S-corp Accountable Plan, and what the IRS looks for.
Owner payHow Profitable Business Owners Get Money Out of Their Business
Owner draws, payroll, distributions, and S-corp reasonable compensation — how the method depends on entity type and why sloppy owner pay creates audit risk.
EstimateHow Much Tax Will I Pay Selling My Business?
A walkthrough of the inputs that decide the bill — entity type, asset vs stock, basis, state residency, and deal terms.
Tax planningHow Much Should I Save Each Month for Taxes?
A simple monthly savings formula, why profit — not revenue — is the right starting point, and how to build a system you'll actually follow.
Owner payHow Sole Proprietors Pay Themselves: Owner's Draws, Profit, and the SE Tax Reality
Sole proprietors take owner's draws — not paychecks. All net profit is taxable whether or not you withdraw it. On top of income tax, self-employment tax is 15.3% on net profit. When to evaluate the S-corp election.
Tax planningHow to Choose a CPA for Your Business: What to Look For, What to Ask, and Red Flags to Avoid
Not all CPAs do the same thing. A filing CPA prepares your return; a planning CPA calls in October with recommendations. Questions to ask, red flags to avoid, specialization matters, and what a reasonable engagement costs.
S-corp planningHow to Actually Elect S-Corp Status: Form 2553, Deadlines, and What Happens Next
The calculator said it's worth it. Now what? A step-by-step guide to filing Form 2553, the March 15 deadline, late election relief, and what to set up in the first month as an S-corp.
Business setupHow to Get an EIN for Your Business (Free, Online, Takes 5 Minutes)
What an EIN is, why every business owner needs one, and how to apply for free directly from the IRS.
Tax planningHow to Pay Quarterly Taxes as a Small Business Owner
What estimated taxes are, when they're due, and how to avoid surprise bills by saving the right amount throughout the year.
S-corp planningHow to Actually Pay Yourself From an S-Corp
S-corp owners get paid two ways: W-2 salary through payroll, and distributions from the business account. What each one is, how to set them up, and what the IRS expects.
Exit planningWhen and How to Start Planning a Business Exit
Exit planning should start years before a sale. Here's what to work on first and how the CPA, advisor, and M&A team need to align.
Tax deductionsHSA for Self-Employed Business Owners: The Triple Tax Advantage Account
Contributions are deductible, growth is tax-free, qualified withdrawals are tax-free — the HSA is the only account with all three benefits. HDHP requirements, 2025 limits, the stealth retirement account strategy, and how S-corp owners access it.
Tax planningIndependent Contractor Taxes: What You Owe and How to Plan
Going from W-2 to 1099 changes your tax picture significantly — SE tax on every dollar, no withholding, quarterly payments required. What the full tax bill looks like and the moves that reduce it.
Exit planningInstallment Sales: How to Spread a Business Sale Tax Bill Over Multiple Years
What an installment sale is, how the gross profit percentage works, and the §1245 recapture front-loading problem most sellers don't know about until it's too late.
InsuranceInsurance for Business Owners: What You Actually Need
Most business owners are over-insured in places that don't matter and under-insured in places that do. A framework for thinking about business and personal insurance — what each layer is for, the five gaps that show up most often, and how insurance decisions interact with tax planning.
Tax planningIRS Audit Guide for Business Owners: How Audits Work, What Triggers Them, and How to Respond
Most IRS audits of small businesses are correspondence audits — a letter asking about a specific item. What triggers audits, what to do when you get the letter, and how proper documentation prevents most problems.
California taxIs the California $800 LLC Tax Deductible?
When the annual LLC tax applies, when it can be deducted, and whether your entity structure still makes sense.
Tax planningSchedule K-1 Explained: What It Is, What the Boxes Mean, and Why It Affects Your Return
A K-1 reports your share of income, deductions, and credits from a partnership, S-corporation, trust, or estate. What each box means, where it flows on your personal return, and the passive activity rules that limit losses.
Business structureLLC Operating Agreement: What to Put in Writing When Two People Share a Business
An operating agreement governs your LLC when partners disagree, when someone wants out, or when contributions were never equal. What it covers, what California defaults to without one, and the provisions that protect the partner doing more of the work.
S-corp planningLLC vs S-Corp: Which Business Structure Is Right for You?
An LLC is a legal structure; an S-corp is a tax election — and most S-corp owners have both. When the S-corp election saves money, when it doesn't, and what the compliance costs actually are.
Quarterly taxesI Missed a Quarterly Tax Payment — What Actually Happens?
The penalty for missing a quarterly estimated tax payment is smaller than you think, and it's not a crisis. Here's the actual math, how to catch up, and what to do next.
Filing deadlinesWhat Happens If I Miss the April 15 Tax Deadline?
Missing the filing deadline is not the same as failing to pay. The penalties are different, the fix is straightforward, and filing late is almost always better than not filing at all.
Tax planningMulti-Member LLC Taxes: How Partnerships Are Taxed, Who Files What, and the SE Tax Trap
A multi-member LLC is taxed as a partnership by default — filing Form 1065 and issuing K-1s. Active members pay SE tax on their full distributive share. When the S-corp election saves money, and how partnership basis rules differ from S-corps.
Tax planningNet Investment Income Tax: The 3.8% Surtax That Surprises High-Earning Business Owners
The 3.8% NIIT applies to investment income for individuals above $200,000 in modified AGI — on top of regular income tax and capital gains rates. It applies to passive business income, rental income, and gains from selling a business.
Tax planningNet Operating Loss (NOL): What Happens When Your Business Loses Money
An NOL occurs when business deductions exceed income. Post-TCJA rules: no carryback for most, indefinite carryforward, 80% income limitation. How pass-through basis rules interact, and why tracking NOL carryforwards carefully is critical.
Real estate taxPassive Activity Loss Rules: Why Rental Losses Get Stuck
Rental losses are passive by default — they can only offset passive income, not your W-2 or business income. Here's how the $25k allowance works, when it phases out, and the three exceptions.
Business operationsPayroll Taxes for Employers: FICA, FUTA, SUTA, Deposit Schedules, and the Trust Fund Penalty
When you hire employees, you're responsible for withholding and remitting payroll taxes on a strict schedule. Late deposits trigger penalties starting at 2%. The trust fund penalty — 100% of withheld taxes, assessed personally — is not theoretical.
InsurancePersonal Insurance for Business Owners: The Coverage Gaps That Matter
Health, term life, disability, long-term care, personal umbrella — which coverages are non-negotiable for self-employed business owners, which are over-marketed, and the disability gap most owners don't realize they have until it's too late.
BookkeepingHow to Read a Profit & Loss Statement (With Real Examples)
A plain-English walkthrough of what a P&L actually tells you, with sample statements for a personal trainer, therapist, salon, and franchise restaurant.
Tax deductionsThe QBI Deduction: How the 20% Pass-Through Deduction Works for Business Owners
Section 199A lets pass-through business owners deduct up to 20% of qualified business income. Who qualifies, what the income limits are, and how it interacts with S-corp structure.
Exit planningQSBS §1202: The $10M Tax Exclusion Most C-Corp Founders Have Never Checked
How the §1202 exclusion works, who qualifies, and the five-question check that could save C-corp founders up to $10M in federal tax on a business sale.
Business operationsQSEHRA: How Small Businesses Reimburse Employees for Health Insurance Tax-Free
A Qualified Small Employer HRA lets businesses under 50 employees reimburse employees for individual health insurance and medical expenses — tax-free, deductible, no group plan required. 2025 limits, notice requirements, and QSEHRA vs ICHRA comparison.
Tax planningQualified Opportunity Zones: Defer and Potentially Exclude Capital Gains
A QOZ investment defers capital gains from a recent sale if reinvested within 180 days. Gains held in a QOZ fund for 10+ years are excluded from federal capital gains tax. Three-tier benefits, the 180-day window, QOZ vs 1031, and fund quality considerations.
Tax planningSolo 401(k), SEP-IRA, and SIMPLE IRA: Which Retirement Plan Is Right for Your Business?
The three main retirement plans for self-employed business owners compared — contribution limits, who qualifies, deadline rules, and when each one makes sense. With 2025 limits.
Tax planningRoth Conversion Strategy: When and How to Convert a Traditional IRA or 401(k) to Roth
A Roth conversion moves money from a pre-tax account to Roth — you pay income tax now, then the account grows and withdraws tax-free forever. When it makes sense, how to calculate the optimal conversion amount, the Medicare IRMAA trap, and how business owners use income control to create conversion windows.
Equity compensationRSU Tax Treatment: What You Owe When Shares Vest
RSUs create ordinary income at vesting — not capital gain. The 22% supplemental withholding rate leaves most high earners short. Here's how the math works and what to do about it.
S-corp planningS-Corp Distributions: How They Work, When to Take Them, and How to Avoid Triggering an Audit
S-corp distributions are not subject to payroll tax — but you must pay a reasonable W-2 salary first. How distributions work, when they become taxable, and how to structure the salary/distribution split correctly.
S-corp planningS-Corp Reasonable Compensation: What the IRS Actually Requires and How to Set Your Salary
The IRS requires S-corp owners to pay themselves a 'reasonable salary' — and has audit procedures to enforce it. What factors the IRS considers, how auditors typically approach S-corp compensation cases, and a practical method for setting a defensible number.
Sales taxSales Tax for Small Business Owners: Collection, Reporting, and What Triggers It
When you have to collect sales tax, what nexus means, California rates and registration, how to remit, and the most common mistakes.
San Diego businessSan Diego Business License Requirements: City, County, and State
There's no single San Diego business license — requirements differ by city, unincorporated county land, and industry. Here's what actually applies to you.
Tax planningSection 1031 Exchange: How to Defer Capital Gains Tax When Selling Real Property
A 1031 exchange defers capital gains and depreciation recapture when you sell investment property and reinvest in like-kind property. The 45-day identification and 180-day close deadlines are absolute. How it works, the basis carry-over, and the step-up at death.
Tax deductionsSection 179 and Bonus Depreciation: How to Deduct Equipment and Vehicles in Year One
Section 179 and bonus depreciation let businesses deduct the full cost of qualifying equipment, vehicles, and software in the year purchased — instead of depreciating over 5–7 years. 2025 limits, the SUV cap, and what California doesn't conform to.
Tax deductionsSelf-Employed Health Insurance Deduction: How It Works and Why Most Owners Miss It
The self-employed health insurance deduction reduces your adjusted gross income — not just your taxable income. Here's who qualifies, how to claim it correctly, and what's different for S-corp owners.
Tax planningSelf-Employment Tax Explained: Rates, Calculation, and How to Reduce It
Self-employment tax is 15.3% on net profit — on top of income tax. How SE tax is calculated, what the deductible half actually saves, and the three ways to reduce it.
Real estate taxShort-Term Rental Tax Rules: The 7-Day Rule, Passive vs. Non-Passive, and the Vacation Home Trap
If your Airbnb averages 7 days or fewer per stay, it's not a rental property under the tax code — it's a business. That changes whether your losses can offset your ordinary income.
Tax deductionsSolo Service Business Tax Deductions: The Complete Checklist
Eight deductions every sole prop and freelancer should be claiming — with dollar values at $100k and $150k net profit. None require an S-corp.
Tax deductionsDeducting Business Startup Costs: The $5,000 Rule and 15-Year Amortization
The IRS lets you deduct up to $5,000 in startup costs in your first year of business — but only if total costs stay under $50,000. Above that, startup costs must be amortized over 180 months.
Tax planningTax Extensions Explained: What Filing an Extension Does (and Doesn't) Do
A tax extension gives you more time to file — not more time to pay. Taxes owed are still due on the original deadline. Key deadlines, how to file, when extensions are the right call, and the penalty comparison between filing late with vs without an extension.
Tax planningAre Business Loans Taxable Income? How Debt, Interest, and Forgiveness Are Taxed
Loan proceeds are not income — but forgiven debt usually is. Business interest is deductible when the loan funded business purposes. Shareholder loans from S-corps require written notes and market interest to avoid reclassification as distributions.
Tax deductionsVehicle and Auto Deductions: Standard Mileage vs Actual Expense
Two methods to deduct business vehicle use — standard mileage (70¢/mile in 2025) or actual expense. How to choose, what documentation is required, and the luxury car and SUV limits that change the math.
Tax deductionsWhat Counts as a Business Write-Off?
The ordinary-and-necessary standard, common deductible expenses, and why personal charges don't become write-offs just because they clear the business account.
Tax formsWhat Is a K-1 Form? (And What Do You Do With It?)
A K-1 is your share of income or loss from a pass-through entity. It arrives late, it's confusing, and yes — you owe tax on it even if no cash was distributed.
SE taxWhat Is Self-Employment Tax? (And Why Is It So High?)
Self-employment tax is 15.3% on your net profit — on top of income tax. Here's why it exists, how it's calculated, what the deduction does, and when an S-corp starts making sense.
Tax deductionsWhat Is the QBI Deduction? (The 20% Pass-Through Deduction Explained)
Section 199A lets most sole proprietors, partnerships, and S-corp owners deduct 20% of their business income. Here's how it works, who qualifies, and what kills it.
Tax planningWhat Proactive Tax Planning Actually Looks Like
Filing a return tells you what already happened. Planning changes what the next one looks like. Here's what the difference looks like in practice.
RecordkeepingWhat Tax Records Do I Actually Need to Keep?
The IRS has a 3-year window to audit most returns. Here's exactly which records to keep, for how long, and the simplest system that makes tax time not a nightmare.
Buying a businessWhat to Do Before vs. After the LOI When Buying a Business
Pre-LOI is cheap exploration. The LOI is the commitment moment. Post-LOI, the meter starts running. A stage-by-stage action guide for first-time business buyers.
ReturnsWhy Your Business and Personal Tax Returns Need to Be Coordinated
When business and personal returns are handled separately, key decisions get made in the dark — retirement limits, QBI, distribution timing.
CPA & advisorWhy Your CPA and Financial Advisor Should Be Coordinating
Most owners have a CPA and an advisor who have never spoken. Here's what gets missed when those two conversations stay separate.
Planning guideThe First-Year Setup Guide: S-Corp, Salary, and Quarterly Taxes
S-corp election decision, defensible W-2 salary, payroll setup, and a quarterly tax routine — with embedded calculators at each step.
Planning guideThe Busy Owner's DIY Tax Planning Guide
Set your S-corp salary correctly, calculate quarterly estimates, and build a proactive plan that eliminates April surprises.
Planning guideThe Cash & Distribution Strategy Guide
Build a distribution plan, move money out of the business efficiently, and start turning profitable years into a personal balance sheet.
Planning guideThe RSU & Stock Option Tax Coordination Guide
Coordinate RSU vesting, ISO/AMT exposure, and concentrated positions so your CPA and advisor are working from the same picture.
Planning guideThe Solo Service Pro's Tax Strategy Guide
SE tax break-even analysis, deductions most solo pros miss, the S-corp question answered with actual math, and a quarterly routine that eliminates April surprises.
Planning guideThe Business Owner's Payroll Tax Guide
Deposit schedules, the trust fund penalty, worker classification risk — what most owners with employees don't know until it's too late.
Planning guideThe Business Exit Tax Planning Guide
Asset sale vs. stock sale, QSBS eligibility, installment elections, and California exit tax — the decisions that determine how much you actually keep.
Planning guideThe First-Year Business Owner's Tax Guide
What self-employment tax is, how quarterly estimates work, the business foundation steps that protect you from April surprises, and the deductions available from day one.
Planning guideThe Solo Owner's Deductions and Tax Strategy Guide
QBI deduction, Solo 401(k), home office, vehicle, and SE health insurance — with calculators built in.
Planning guideHow to Set Up an S-Corp: The 60-Day Transition Guide
A step-by-step guide for sole proprietors and single-member LLCs making the switch to S-corp — Form 2553 timing, salary setup, payroll service selection, and quarterly tax rhythm.
Business operationsBooks and Podcasts for New Business Owners: A Short, Opinionated List
Most business book lists are too long to be useful. This is a short, opinionated list of what actually helps new owners understand money, tax, and how a business works.
California taxCalifornia Capital Gains Tax Rate: Why CA Has No Preferential Rate
California taxes capital gains as ordinary income, at rates up to 13.3%, with no special long-term rate. Here's what that means for a California high earner selling stock or a business.
California taxCalifornia Franchise Tax for LLCs and S-Corps: What You Actually Owe
California's franchise tax is not one charge — it's two for LLCs, and a percentage of income for S-corps. Here's how the $800 minimum, the gross receipts fee, and the 1.5% S-corp rate work.
Tax deductionsTax Basics for Inventory-Based Businesses: COGS, Resale Certificates, and Sales Tax
When your business buys things to resell, the tax picture is different from a service business — cost of goods sold, resale certificates, and tracking purchase cost.
Tax planningSEP IRA vs Solo 401(k): Which Is Better for the Self-Employed?
Both plans let self-employed people shelter up to $72,000 in 2026, but they work differently — in contribution deadlines, Roth options, catch-up contributions, and administrative complexity.
S-corp planningWhen to Convert Your LLC to an S-Corp: The Income Threshold and the Timing
An S-corp election saves self-employment tax, but it adds payroll and compliance costs. Here's the net-profit level where the savings usually win, and the March 15 election deadline.
Tax planningYear-End Tax Planning Checklist for Small Business Owners
The decisions that reduce your tax bill are mostly made before December 31, not in April. What to act on before year-end, and what can wait until the filing deadline.