Category: Founder Finance
Building a Personal Holding Structure for 3-5 Small Business Bets
Once you own 2-plus income-producing assets, a personal holding LLC structure gives small operators a treasury layer that reduces self-employment...
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...
Section 179, Vehicle & Home-Office Deductions Done Right: The Audit-Safe Founder Playbook
Section 179 and home-office deductions can save founders thousands — but the vehicle caps, business-use rules, and S-corp accountable plan...
Boring Business Second Income Stream: De-Risk Your Startup with Predictable Cash
A boring business—vending route, cleaning company, or laundromat—can generate $2k–$4k/month in predictable net income that makes a startup's zero-revenue phase...
Broker vs. Direct Sale: Fees, Outcomes, and When Each Path Wins for Founders
Business brokers charge 8–12% on sub-$1M deals — on a $1M exit that's up to $120K off the top. This...
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...
Expansion Revenue for a One-Person SaaS: How to Push NRR Above 100%
A solo SaaS founder's guide to engineering net revenue retention above 100% — the compounding metric that grows MRR from...
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...
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