Category: Founder Finance
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...
Mega Backdoor Roth via Solo 401(k): Putting $47,500 of After-Tax Savings to Work in 2026
How solo founders can use a custom solo 401(k) plan document to contribute up to $47,500 in after-tax dollars in...
Best Recession-Resilient Business Models to Start in 2026
Six business archetypes — B2B services, niche SaaS, info products, physical goods, staffing, and maintenance/repair — scored against four recession-resilience...
First-Time Acquirer Due Diligence Checklist: 47 Items Before You Wire Money
A 47-item due diligence checklist for first-time SMB acquirers in the $300K–$2M range, covering financials, operations, customers, legal contracts, and...
The MRR-to-FIRE Bridge: Turning Recurring Revenue Into a Founder FI Number
A rigorous dual-stack FI methodology for bootstrapped founders: how to discount MRR as a synthetic annuity, why your founder FIRE...
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...
Founder Emergency Fund: How Much Runway You Actually Need When Income Is Variable
The 3-6 month emergency fund rule is designed for salaried employees — not founders with variable income. Here is the...
The Two-Income Household With One Founder: How to Structure Everything
For the household with one W-2 spouse and one founder: how to structure health insurance, tax brackets, runway accounting, and...
Safe Withdrawal Rate When Part of Your Income Is Active Business Cash Flow
A founder-specific blended safe withdrawal framework showing how to haircut business distributions for reliability and calculate your true portfolio burden...
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