Knowledge Base
Small business & personal finance — in under 5 slides.
Concise, partner-written guides on the questions small business owners and individuals ask us most. Each resource is built as a short slide deck you can scan in three minutes.
All resources
Tax
S-Corp vs. LLC for Small Business Owners
When the S-corp election actually saves money for an LLC owner, and when it costs more in headaches than it pays in taxes.
Tax
K-1 Income: What It Is and How to File It
If you're a partner, S-corp shareholder, or LLC member, you'll get a K-1. Here's how to read it and where each number lands on your 1040.
Accounting
When (and How) to Switch From Cash to Accrual Accounting
Cash basis is simple but lies about timing. Here's when accrual is required, when it's just smart, and how to switch.
Fractional CFO
When Does a Small Business Need a Fractional CFO?
Bookkeepers record. Accountants close and report. CPAs file. None of them help you make the next decision. That's what a CFO does.
Tax
Multi-State Sales Tax for Remote and Online Businesses
Wayfair turned every remote-sale state into a potential tax obligation. Here's how to know where you owe, register, and stay clean.
Tax
Quarterly Estimated Tax for Self-Employed and Business Owners
If you're not on a W-2, the IRS expects four prepayments a year. Miss them and you owe penalties even if you pay in full at filing.
Tax
AMT, ISOs, NSOs, and RSUs: A Survival Guide
Equity comp tax is where high-income professionals lose the most money — usually to AMT. Here's the framework for each instrument.
Tax
California Small Business Franchise Tax Explained
The minimum $800 every California entity owes — and the layered taxes that surprise founders who form here without thinking it through.
Accounting
Month-End Close Checklist for Small Businesses
A repeatable monthly close cadence — what to reconcile, what to accrue, and how to know your books are actually done.
Accounting
Reading Your P&L: What Owners Should Actually Look For
The numbers your accountant hands you each month. Here's how to read past the gross totals to the signals that matter.
FP&A
Building a 13-Week Cash Forecast
The single most useful financial tool for a small business. Not a budget, not a P&L — a weekly cash projection you actually use.
FP&A
Pricing Analysis: Cost-Plus vs. Value-Based
Most owners price by adding margin to cost. The good ones price to the value the customer gets. Here's how to tell which approach fits.
Payroll
Multi-State Payroll Setup for Small Businesses
One remote employee in another state means new tax registrations, withholding rules, and compliance work. Here's the playbook.
Payroll
Contractor (1099) vs. Employee (W-2): The IRS Test
Misclassifying employees as contractors is one of the most common — and most expensive — small business mistakes. Here's how the IRS decides.
Business Valuation
Business Valuation Methods Explained
Three approaches — income, market, asset — and how appraisers reconcile them into a single defensible number.
Business Valuation
Buy-Sell Agreement Valuation: What You Need to Know
When a partner exits, the buy-sell agreement decides the price. If the valuation method isn't right, the deal falls apart.
Tax
BOI Reporting Under the Corporate Transparency Act
Beneficial ownership reporting (BOI) requirements for most U.S. small businesses — who must file, what's reported, deadlines, and penalty risk.
Tax
Solo 401(k) vs. SEP-IRA for Self-Employed Owners
If you're self-employed with no employees, both plans let you stash big retirement contributions — but the math, deadlines, and admin differ.
Payroll
1099-NEC and 1099-MISC Filing Checklist for Small Businesses
Who to send 1099s to, what the dollar thresholds are, when they're due, and how to avoid IRS penalties for late or wrong filings.
FP&A
Building a KPI Dashboard Your Business Actually Uses
Most KPI dashboards are pretty and ignored. Here's how to build one with the 5–8 numbers that should drive every owner conversation.
Fractional CFO
Owner Compensation: Salary, Distribution, and Profit Sharing
How owner-operators should pay themselves — salary vs. distribution split, reasonable comp, retirement contributions, and how it all interacts with tax.
Accounting
Revenue Recognition for SaaS and Subscription Businesses
ASC 606 changed how SaaS recognizes revenue. Here's the framework, what trips up small SaaS, and how to set up books that pass diligence.
Business Valuation
Estate and Gift Tax Valuation Discounts
DLOM and DLOC discounts can reduce the taxable value of a transferred business interest by 30–50%. Here's how they work and what survives IRS scrutiny.
Accounting
Chart of Accounts: Setup for SMBs by Industry
Your chart of accounts shapes every report you ever read. Here's how to set one up by industry — agencies, e-commerce, real estate, restaurants — so the numbers tell the truth.
Accounting
Deferred Revenue for Service Businesses (Not Just SaaS)
Agencies, consultancies, memberships, retainers, and subscription services all sit on deferred revenue. Here's how to set it up and what most owners get wrong.
Accounting
GAAP vs. Cash vs. Tax Basis: When Each Matters
Three ways to keep your books — each with different rules and audiences. Here's when each basis matters and which one your business needs.
Accounting
ASC 606 Revenue Recognition for Service Businesses
ASC 606 isn't a SaaS-only rule. Agencies, consultancies, memberships, and project-based services all need to apply the five-step model. Here's how.
Accounting
Reading the Balance Sheet: What Owners Should Look For
Most owners stare at the P&L and ignore the balance sheet. That's where the early-warning signals actually live. Here's how to read yours.
Tax
5 Bookkeeping Mistakes That Trigger IRS Audits
Most IRS audits start from patterns in the books, not random selection. Here are the five bookkeeping mistakes most likely to put you on the audit list.
Tax
5 Multi-State Sales Tax Mistakes E-commerce Owners Make
Wayfair turned every remote sale into a potential tax obligation. Here are the five sales tax mistakes that turn into back-tax exposure.
Tax
5 Owner Compensation Mistakes That Trigger IRS Scrutiny
How you pay yourself decides how much tax you pay — and how much audit risk you carry. Here are the five owner-comp mistakes that cost owners the most.
Business Valuation
5 Estate Planning Mistakes Family Businesses Make
Family businesses without estate plans usually don't survive the founder's death. Here are the five mistakes that destroy enterprise value and family relationships.
Tax
The Augusta Rule (§280A(g)): Rent Your Home to Your Business
Up to 14 days/year of personal residence rental to your own business — tax-free to you, deductible to the business. Here's how to do it right and why the IRS scrutinizes it.
Tax
Accountable Plan Reimbursements for S-Corp Owners
Legally pull money out of your S-corp for home office, mileage, cell phone, and internet — without it becoming taxable income to you. Here's how to set one up.
Tax
Backdoor Roth IRA and Mega Backdoor Roth Explained
High-income earners can't contribute to Roth IRAs directly. The backdoor and mega-backdoor strategies legally route after-tax money into Roth — here's how each works.
Tax
Defined Benefit & Cash Balance Plans for High-Income Solo Owners
When Solo 401(k) and SEP-IRA caps aren't enough, defined benefit and cash balance plans can shelter $200K–$300K+ per year. Here's when they make sense.
Tax
QBI (Section 199A) Deduction: The Full Walkthrough
The 20% pass-through deduction has SSTB phase-outs, wage and UBIA limits, REIT/PTP rules, and aggregation elections. Here's the complete framework, not the surface version.
Tax
Year-End Tax Planning Checklist for SMB Owners
The 15-item checklist of things to confirm or do by December 31 to optimize your tax position. Updated annually.
Tax
Tax Changes Taking Effect in 2026: SMB Owner Edition
What's changing for small business owners and individuals in 2026 — TCJA sunset provisions, bonus depreciation phase-down, OBBBA permanent items, and more.
Tax
California PTET: The SALT-Cap Workaround for High-Income Owners
California's Pass-Through Entity Tax election lets passthrough owners pay state tax at the entity level, sidestepping the $10K federal SALT cap. Here's how to elect and when it pays off.
Tax
New York PTET: Election Mechanics and When It Pays Off
New York's Pass-Through Entity Tax election bypasses the federal SALT cap for passthrough owners. Here's the New York-specific rules, deadlines, and trade-offs.
Tax
Illinois PTET: SALT Workaround for Illinois Passthroughs
Illinois's Pass-Through Entity Tax election lets passthrough owners deduct state tax federally by paying at the entity level. Here's how Illinois's version works.
Tax
Massachusetts PTET (Pass-Through Entity Excise): How It Works
Massachusetts's Pass-Through Entity Excise — the PTET equivalent — lets passthrough owners deduct state tax federally by paying at the entity level. Here's the Massachusetts version.
Tax
The Short-Term Rental Tax 'Loophole' Explained
How material participation in short-term rentals can let W-2 earners offset wages with rental losses — the legitimate framework, not the influencer pitch.
Tax
Real Estate Professional Status (§469(c)(7)): The Complete Framework
Two tests, strict hour requirements, spouse aggregation rules, and the elections that make it work. The definitive walkthrough.
Tax
Self-Rental Rules: When You Rent Property to Your Own Business
Renting your own building to your own business sounds like a clean tax move — but §469(c)(2) recharacterizes the income and changes the math. Here's what you need to know.
Tax
Opportunity Zones: Capital Gain Deferral and Tax-Free Growth
Defer (and potentially eliminate) capital gains tax by investing in Qualified Opportunity Funds. Here's how it works and when it makes sense.
Accounting
Concierge Medicine & Direct Primary Care: Tax & Accounting Structure
Membership-based medical practices have unique accounting and tax considerations. Here's how to set up books, recognize revenue, and structure the entity.
Tax
The Solo Practitioner Retirement Stack: 401(k) + Cash Balance + DB
How high-income solo physicians, lawyers, and dentists combine multiple plans to shelter $300K+/year. The full stack with sequencing and trade-offs.
Tax
Section 1202 QSBS: Up to $10M Gain Tax-Free
Qualified Small Business Stock can exclude up to $10M (or 10× basis) of gain from federal tax. Here's eligibility, holding requirements, and OBBBA's 2025 tiered rules.
Tax
ISO Exercise Multi-Year Strategy: AMT-Optimized Planning
Exercising ISOs all at once usually triggers crushing AMT. Splitting the exercise across multiple years minimizes the surprise. Here's the framework.
Tax
Amazon FBA Multi-State Tax: Nexus, Marketplace Facilitators, and Filings
Amazon FBA warehouses create physical nexus in 20+ states. Marketplace facilitator laws shift collection but not registration. Here's the FBA seller's tax map.
Accounting
Inventory Costing Methods Compared: FIFO, LIFO, Weighted Average
Choosing among FIFO, LIFO, and weighted-average affects your gross margin, taxable income, and balance sheet — here's how to pick the right method.
Tax
1099-K Threshold Changes: What Stripe/PayPal/Venmo Report
Third-party payment networks must report payments above thresholds that have been phased in. Here's the current rule, the past delays, and how to reconcile with your records.
FP&A
DTC Unit Economics for Non-VC Brands: CAC, LTV, ROAS, Margin
Direct-to-consumer unit economics framework adapted for bootstrapped and growth-stage DTC brands — without the VC-pitch framing.
Tax
FICA Tip Credit: An Overlooked Restaurant Tax Credit
Restaurants can claim a federal credit for the employer portion of FICA paid on employee tips. Often missed; worth $5K–$50K+ per year for a typical restaurant.
Accounting
Multi-Unit Restaurant Accounting: Consolidating From One Location
When one location becomes three, accounting complexity grows fast. Here's how to set up consolidated books that produce comparable P&Ls and roll up into a meaningful group view.
Accounting
Cash Control Procedures for Cash-Heavy Businesses
Restaurants, salons, retail with significant cash collections face heightened IRS scrutiny. Here are the cash control procedures that defend an audit.
Accounting
Job Costing for Small Contractors Without Enterprise Software
How to set up real job-level profitability tracking in QuickBooks or Xero — without buying construction-specific software you don't need.
Payroll
Certified Payroll & Davis-Bacon Compliance for Public Works
Federal Davis-Bacon and state prevailing wage laws require certified payroll filings on public projects. Here's the compliance framework.
Fractional CFO
Bonding Capacity and the WIP Schedule
Construction contractors need bonding to win larger projects. Bonding capacity hinges on financial statements — and the WIP schedule is the critical input.
Tax
FBAR and Form 8938: Foreign Account Reporting Walkthrough
FBAR (FinCEN 114) and Form 8938 (FATCA) report foreign financial accounts to the U.S. government. Different thresholds, different penalties, both essential.
Tax
PFIC Rules on Indian Mutual Funds: Why They Hurt
Indian mutual funds, ULIPs, and many Indian investment products are PFICs under U.S. tax law — and PFIC tax is brutally punitive. Here's what to do.
Tax
RNOR Transition Planning: Returning to India from the U.S.
Returning Indians enjoy 'Resident but Not Ordinarily Resident' (RNOR) status for up to 3 years — sheltering foreign income from Indian tax. Here's how to maximize the window.
Tax
Section 6166: Pay Estate Tax in Installments on Family Business Estates
When a family business is the bulk of the estate, §6166 lets heirs pay estate tax over 14 years at favorable interest — saving the business from forced sale.
Business Valuation
ESOPs for SMB Owners: An Alternative Exit Strategy
Employee Stock Ownership Plans let SMB owners sell their business to employees with significant tax benefits. Here's the framework.
Business Valuation
GRAT and IDGT Primer: Wealth Transfer for Family Businesses
Grantor Retained Annuity Trusts (GRATs) and Intentionally Defective Grantor Trusts (IDGTs) are wealth-transfer tools for SMB owners with appreciating businesses. Here's the framework.
More guides coming. Building a venture-scale startup? See StartupCFO.AI resources for venture-stage finance topics.
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