Category: Personal Finance
Collect Unemployment Benefits and 1099 Self-Employment Income: The State-by-State Rules for Founders and Freelancers
Every state has different rules about whether 1099 or self-employment income reduces your unemployment benefits — this guide breaks down...
How Much Term Life Do You Need When Your Family Depends on the Business?
A founder-specific five-layer framework for sizing term life insurance that accounts for income replacement, SBA loan personal guarantees, buy-sell agreement...
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,...
Freelance Bridge to Product: Fund Your Build Without Burning Savings
A targeted consulting sprint generating $8k–$15k/month gives recently laid-off professionals with domain expertise a powerful third path: fund your product...
Own-Occupation Disability Insurance for Founders: Benefit Math and Policy Design (2026)
Most founders have no employer disability plan to fall back on. This guide breaks down how to design a true...
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...
S-Corp Election Breakeven 2026: The Real Founder Math ($80K–$184K)
The 2026 S-corp election breakeven is ~$72K–$73K net profit using the corrected payroll tax formula. See the full tax savings...
QSEHRA 2026: The Micro-Business Health Benefit for Founders With 1-4 Employees
How founders with 1–4 W-2 employees can use a QSEHRA in 2026 to offer tax-free health reimbursements up to the...
ICHRA for a One-Person S-Corp: Can You Actually Reimburse Your Own Premiums?
A solo S-corp owner's definitive guide to ICHRA one person S-corp owner eligibility: why IRC 1372 blocks you from your...
Your Founder Benefits Package: Replacing the Corporate Safety Net Without a 9-to-5
Build your complete founder benefits package 2026 with real cost numbers: ACA health insurance, HSA, Solo 401k, disability insurance, term...
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