#entrepreneurship

Entrepreneurship

Financial guidance and accounting tips for entrepreneurs and startups

433 postsView all tags Back to All Posts

May 18, 202615 min read

Section 1235 Capital Gains Treatment for Patent Sales: How Inventors Convert Royalty Income Into Long-Term Capital Gain

Section 1235 lets individual inventors and qualifying early investors treat a patent sale as long-term capital gain — even without a one-year holding period — if they transfer all substantial rights. This guide explains who qualifies as a holder, why the rule survived the TCJA carve-out for self-created intangibles, and how to draft the transfer so the IRS sees a sale rather than a royalty license.

Mike Thrift

tax-planningcapital-gainstax

May 17, 202610 min read

Bookkeeping for Food Truck Owners: Cash Sales, COGS, and Sales Tax

A step-by-step bookkeeping system for food trucks — separating business money, building a truck-specific chart of accounts, running a daily cash close, tracking food cost at 25–30% of revenue, and treating collected sales tax as a liability rather than income.

Mike Thrift

bookkeepingsmall-businesscost-of-goods-sold

May 17, 202611 min read

Quality of Earnings Reports: How Sellers Protect Their Price in a Business Sale

A Quality of Earnings report normalizes a company's earnings, reconciles them to cash, and tests every add-back. Sellers who commission their own QoE averaged a 7.4x EBITDA multiple versus 7.0x for those who did not.

Mike Thrift

business-acquisitionsmall-businessfinancial-reporting

May 16, 202612 min read

Section 195 and Section 248: The First $5,000 Every Founder Can Deduct

Section 195 and Section 248 let founders deduct the first $5,000 of startup costs and the first $5,000 of organizational costs in year one, with the remainder amortized over 180 months. A guide to the $50,000 phase-out, the deemed election, and the mistakes that forfeit the deduction for LLCs, partnerships, and corporations.

Mike Thrift

tax-deductionsstartuptax-planning

May 16, 202613 min read

Section 7701(b) Substantial Presence Test for Foreign Entrepreneurs: The 183-Day Formula, Closer Connection, and Treaty Tie-Breakers

A practical walkthrough of IRC Section 7701(b) for globally mobile founders — the 31-day floor, the weighted three-year 183-day formula, exempt-individual rules, the closer connection exception (Form 8840), and treaty tie-breakers (Form 8833) — with a worked example showing how 130 U.S. days in 2026 can trigger worldwide taxation.

Mike Thrift

international-taxtax-complianceexpatriate

May 14, 202611 min read

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.

Mike Thrift

crowdfundingtaxtax-compliance

May 13, 202613 min read

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.

Mike Thrift

incorporationc-corptax-planning

May 13, 202612 min read

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.

Mike Thrift

taxtax-compliancesmall-business

May 11, 202615 min read

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.

Mike Thrift

tax-planningcapital-gainsstartup

May 10, 202612 min read

The 2026 SaaS Metrics Stack: LTV, CAC, NRR, and the Rule of 40

Track the SaaS metrics that win term sheets in 2026: LTV, CAC, NRR, churn, CAC payback, and Rule of 40. Includes benchmarks and calculation traps to avoid.

Mike Thrift

saasmetricsstartup

May 9, 202614 min read

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.

Mike Thrift

tax-compliancellcforeign-corporations

May 7, 202614 min read

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.

Mike Thrift

retirement-plansc-corporationfinancing

Start Free→Documentation