Warnings and Pitfalls
What goes wrong and how to avoid it: common financial modeling errors, fundraising missteps, and expensive founder mistakes.
7 articles
The E-2 Visa Investment Spreadsheet: What Actually Counts as Qualifying Spend
A practical guide for founders tracking qualifying investment expenses for E-2 treaty investor visa applications. Eight categories of qualifying spend with typical ranges,…
The Personal Finance of Taking the Entrepreneurial Leap
Startup failure is typically caused by running out of personal money, not bad ideas. Four prerequisites: zero high-interest debt, 6-12 month emergency fund, health insurance…
Marginal vs Effective Tax Rates: The Myth That Costs You Money
People turn down raises and avoid side income because they misunderstand how tax brackets work. You only pay the higher rate on the income above the threshold, not on everything…
Managing Wealth After a Liquidity Event: The First-Year Playbook
Do nothing for 90 days. Assemble a wealth team. Separate operating capital from investment capital. Avoid the common post-exit financial mistakes.
Asset Sale vs Stock Sale: How Deal Structure Affects Your Take-Home
Deal structure can swing net proceeds by 5-15%. Buyers prefer asset sales for the tax step-up. Sellers prefer stock sales to avoid double taxation.
The Revenue Recognition Trap: When Your Books and Your Bank Account Disagree
Revenue recognition and cash collection are different. Deferred revenue, payment terms, and AR aging create gaps.
How to Write an Investor Update That Keeps Your Round Warm
Most founders either never send investor updates or send them only when things are going well. Both are mistakes. A well-written monthly update keeps warm investors engaged…