#entrepreneurship
Entrepreneurship
Financial guidance and accounting tips for entrepreneurs and startups
Crowdfunding and Taxes in 2026: When Kickstarter, GoFundMe, and Indiegogo Money Is Taxable Income
Kickstarter and Indiegogo proceeds are business income reported on Schedule C, while GoFundMe donations may be tax-free gifts only if they pass the IRS detached and disinterested generosity test. The OBBBA reset the Form 1099-K threshold to $20,000 and 200 transactions for tax year 2026, but the reporting rule does not change what counts as taxable income.
Section 351 Tax-Free Incorporation: The 80% Control Test, Boot Traps, and QSBS for Founders
Section 351 lets founders incorporate without immediate tax only if the transferor group owns 80% of voting power and every non-voting class right after the exchange. Miss the control test, contribute services instead of property, or assume liabilities greater than basis, and the gain surfaces anyway. A practical playbook covering boot, the Section 357(c) trap, basis carryover under Sections 358 and 362, and how to preserve QSBS eligibility under Section 1202.
The 90-Day Letter: How Small Businesses Challenge IRS Audit Findings Without Paying First
A Statutory Notice of Deficiency gives a small business 90 days to petition the U.S. Tax Court before the IRS assesses additional tax. This guide explains the CP3219A deadline, Form 5564 waiver, S-case election, and the four realistic responses every owner should weigh.
Section 1045 QSBS Rollover: How Founders Defer Capital Gains by Reinvesting Within 60 Days
Section 1045 lets non-corporate taxpayers defer capital gains from a QSBS sale by reinvesting proceeds into new qualifying small business stock within 60 days. After the 2025 OBBBA expansion (75M gross assets cap, tiered 50/75/100 percent exclusion at 3/4/5 years), the rollover can convert a missed Section 1202 exclusion into a deferred, and potentially excluded, gain.
The 2026 SaaS Metrics Stack: LTV, CAC, NRR, and the Rule of 40
A founder's guide to the SaaS metrics that win term sheets in 2026 — how to calculate MRR, ARR, CAC, LTV, NRR, churn, burn multiple, magic number, and the Rule of 40, with current benchmarks and the calculation traps that quietly destroy investor confidence.
Form 5472 for Foreign-Owned US LLCs: The $25,000 Penalty Trap That Catches Single-Member Disregarded Entities Off Guard
Foreign owners of US single-member LLCs must file Form 5472 by April 15, 2026, even with zero revenue. A capital contribution as small as $1 triggers the requirement, and a missed filing carries a $25,000 minimum penalty plus uncapped $25,000 continuation fees every 30 days after IRS notice.
ROBS Rollover for Business Startups: How to Use Retirement Funds to Finance a Small Business Without Tax or Penalty
A working guide to Rollover as Business Startup (ROBS) arrangements — the five required steps, why only a C corporation qualifies, the Form 5500 and prohibited-transaction rules, IRS-documented failure rates, and when alternatives like SBA loans or 401(k) participant loans make more sense.
Form 5471 Decoded: A US Shareholder's Guide to Filing Categories, Schedules, and Avoiding Six-Figure Penalties
Form 5471 carries automatic $10,000-per-corporation initial penalties capped at $60,000 per year for U.S. persons who own, control, or serve as officers of foreign corporations. Covers the five filing categories, modular schedules, GILTI's rename to NCTI for tax years beginning after December 31, 2025, and the Streamlined and Delinquent Submission routes back into compliance.
SAFE vs Convertible Note: A Founder's Guide to Choosing the Right Early-Stage Financing
A SAFE is a contract granting future equity with no maturity or interest, while a convertible note is a loan with 4–8% interest and an 18–24 month maturity that becomes due if no priced round closes — and Y Combinator's 2018 post-money SAFE locks each investor's ownership at Investment ÷ Cap, dilution that hits founders, not prior SAFE holders.
The Proposal Letter That Wins: A Template and Playbook for Closing More Business
A section-by-section proposal letter template with a real fractional-CFO example, win-rate data on customization and speed, the five mistakes that quietly lose deals, and a seven-point pre-send checklist.
Price Increase Letter to Clients: A Service Business Playbook
A practical playbook for writing a price increase letter that retains clients — covering timing (30/60/90-day notice), the six required elements, industry-specific phrasing, two adaptable templates, and a 60-day rollout timeline for service businesses.
Scope of Work Template: A Freelancer and Small Business Guide to SOWs That Prevent Scope Creep
A practical scope of work template with seven required sections, the difference between SOW and statement of work, and the ambiguous verbs that turn signed contracts into billing disputes.