Category: FIRE
Multiple-Expansion Levers: What Moves Your Sale Multiple from 3x to 5x
On a $500K SDE business, the gap between a 3x and 5x multiple is $1M in founder proceeds — and...
Health Coverage Bridge: From Early Retirement to Medicare at 65 for Founders
A complete 10-year healthcare bridge playbook for founders retiring before 65 — covering ACA MAGI management, HSA drawdown strategy, COBRA...
Lean vs Fat FI Target for the Founder Who Can Always Earn More
A founder with marketable skills has a different FI risk profile than a salaried retiree — here is how to...
MAGI Engineering: How Founders Control Premium Tax Credit Eligibility in 2026
How self-employed founders with $50k–$130k income can use Solo 401(k) deferrals, SE health insurance, HSA contributions, and revenue timing to...
When the Business IS the Retirement Plan — And Why That’s Fragile
Fewer than 20–30% of businesses listed for sale actually sell — yet nearly 80% of owners plan to fund retirement...
Post-Exit Reinvestment Plan: Turning a $1M–$5M Wealth Event Into Lasting FI
A founder exiting with $1M–$5M net-of-tax has a narrow window to make high-leverage allocation decisions. Here is the structured post-exit...
Founder Net Worth Tracking: Separating Business Equity From Personal FI
Most founders track net worth in one column—masking whether business equity growth is actually moving personal FI progress. This two-column...
Rental Income + Operating Business: The 2-Asset FI Blueprint for Founders
Owning a single-family rental alongside a SaaS business is the most common second income stream among founders on the path...
Earnouts and Asset vs. Stock Sale: The Tax Gap That Can Cost You Millions
The same $3M deal can produce wildly different after-tax outcomes. Learn how asset sale vs stock sale tax consequences and...
Dividend Income as a Founder’s Cash-Flow Stabilizer in 2026
A bootstrapped founder with $80k–$120k in a taxable brokerage can build a dividend portfolio (SCHD, VYM, DGRO) yielding 3.5–4.5% to...
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