Category: FIRE
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...
QSBS / Section 1202 Exclusion Planning Before You Exit: 2026 OBBBA Rules
The OBBBA raised the QSBS Section 1202 exclusion cap to $15M and expanded the gross asset threshold to $75M —...
Cash-Flow Stacking: Layer 2-3 Income Streams to Reach FI Faster
A single SaaS income stream creates FI fragility. Learn the cash-flow stacking architecture — layering SaaS MRR, digital products, and...
12-Month Exit Prep for a SaaS or Service Business: What Buyers Actually Want
A month-by-month operator roadmap for bootstrapped SaaS and service business founders with $200K–$2M SDE who are 12–24 months from exit...
Tax-Aware Drawdown Order for a Post-Exit Founder in 2026
A founder-specific drawdown sequence for a $2M net exit: QSBS exclusion management, Roth conversion ladder timing, 0% LTCG harvesting, and...
SEP-IRA vs Solo 401(k) at Every Income Level: Which Wins in 2026?
The SEP-IRA and solo 401(k) both cap at $72,000 in 2026, but for self-employed founders the solo 401(k) shelters up...
Taking Chips Off the Table: Secondary Sales and Partial Liquidity for Founders
Full exits aren't the only way to convert business equity into cash. This post breaks down secondary sales, revenue-based financing,...
Defined-Benefit & Cash-Balance Plans for Solo Founders: Shelter Up to $290K/Year in 2026
Solo founders earning $300K+ who have maxed their solo 401(k) can layer a defined-benefit or cash-balance plan to shelter an...
Concentration Risk: 80% of Your Net Worth Is One Business — Now What?
When 80% of your net worth is locked in one illiquid SaaS, you have a concentration risk problem that no...
The Founder Glidepath: Shifting from Business Income to Portfolio Income (2026)
A 5-phase framework for founders mapping the transition from variable business cash flow to stable portfolio income — with milestone...
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