The 2026 Founder Tax & Money Playbook

Running a business in 2026 means the tax code is one of your biggest line items — and one of your biggest opportunities. The rules shifted again this year: the OBBBA changes, the return of bonus depreciation, new SECURE 2.0 catch-up mechanics, and the ACA subsidy cliff all hit solo founders and small teams in ways most generic advice ignores. This playbook gathers everything we have written about keeping more of what your business earns, structuring compensation sensibly, and using deadlines as decision triggers rather than panic moments. Start with the audit pieces if you have a filing date looming, move to entity and retirement structure when you have breathing room, and use the money-mindset pieces to keep the whole thing calm. Every link below points to a full guide on this site.

Tax Deadlines & Audits to Run Now

• OBBBA mid-year tax audit: 5 moves before September 15
• Section 174A R&D expensing and the 2022–2024 refund deadline
• Bonus depreciation in 2026: how to spend $50K before December 31
• QBI 199A phase-out math: keeping your 20% deduction above $200K

Entity, Compensation & Retirement Structure

• S-corp reasonable compensation in 2026
• The SECURE 2.0 Roth catch-up trap for solo 401(k) owners
• Using an HSA as a stealth triple-tax retirement account
• The ACA subsidy cliff: 5 income levers for founders

Acquisitions, Exits & Severance

• Laid off to LLC: the 60-day checklist for turning severance into a business
• Severance negotiation: keep 6 extra months of runway
• SBA 7(a) financing stack for acquisitions: rates and real costs
• Buy a boomer business with 10% down: the SBA 7(a) playbook
• Recession as opportunity: acquiring a cash-flowing business
• SaaS exit math: engineering your way to a higher multiple
• Churn math: how 5% vs 3% reshapes your timeline

Money Mindset & Cash-Flow Discipline

• Recession signals that matter more than headlines
• How founders audit SaaS subscriptions and cut software costs
• Should I pay off debt or invest in 2026? The calm decision tree
• S&P 500 index fund confusion: the beginner mistake
• Wealthy habits that actually move the math
• Why tracking every expense makes you worse with money