Category: Founder Finance
90-Day Post-Layoff Financial Plan for First-Time Founders (2026)
The first 90 days after a layoff are your highest-leverage window to lock in founder runway — a week-by-week financial...
FIRE Variants Decoded for Founders: Lean, Coast, Barista, and Fat — Which Fits a Bootstrapper?
A founder-lens breakdown of Lean, Coast, Barista, and Fat FIRE variants — with real numbers, illiquid equity caveats, and a...
Seller Financing Structures That Actually Close Deals in 2026
Five concrete seller financing structures for small-business acquisitions in 2026 — with current interest rates, SBA subordination language, and a...
The Above-the-Line Health Insurance Deduction Every S-Corp Founder Misses (2026)
S-corp founders paying health insurance premiums can deduct 100% above the line under IRC §162(l) — but only if the...
Churn Math: How 5% vs 3% Monthly Churn Reshapes Your FI Timeline
A data-driven cohort analysis showing how monthly churn rate at 5%, 3%, and 1.5% reshapes MRR trajectory, LTV, and your...
Sequence-of-Returns Risk When Your Income Is the Business (Not a Portfolio)
Most FIRE frameworks treat sequence-of-returns risk as a portfolio problem — but for founders drawing variable business income, the real...
Can Your Business Equity Count Toward Your Coast FIRE Number?
Most FIRE content ignores illiquid business equity entirely. Here is a founder-specific framework to risk-adjust your business valuation, blend it...
QBI 199A Phase-Out Math for Founders: How to Keep Your 20% Deduction Above $200K
The 2026 QBI deduction phases out starting at $201,750 (single) or $403,500 (MFJ) — here's how pass-through founders use aggregation...
Severance Negotiation for Founders: Keep 6 Extra Months of Runway
Most employees sign the first severance offer. Bootstrapped founders-in-waiting who know what HR can actually flex on can negotiate 20–50%...
Barista FIRE Is Broken for Founders — Here’s the Healthcare Plan B
The 2026 ACA subsidy cliff adds $16K+ to Barista FIRE healthcare costs. For founders, a lean recurring-revenue business replaces the...
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