The 2026 Founder Tax & Money Playbook
Keep more of what your business earns in 2026 — deadlines, entity and retirement structure, exits, and the money mindset to run it all calmly. Every link is a full guide on this site.
Running a business in 2026 means the tax code is one of your biggest line items — and one of your biggest opportunities. The OBBBA changes, the return of bonus depreciation, new SECURE 2.0 catch-up mechanics, and the ACA subsidy cliff all hit solo founders in ways generic advice ignores. This hub gathers our writing on keeping more of what you earn, structuring compensation sensibly, and using deadlines as decision triggers rather than panic moments.
How to use this hub
- Have a filing date looming? Start with the deadlines & audit guides first.
- Got breathing room? Move to entity, compensation & retirement structure.
- Eyeing a sale or acquisition? See acquisitions, exits & severance.
- Then use the money-mindset pieces to keep the whole plan calm.
Tax Deadlines & Audits to Run Now
OBBBA mid-year tax audit: 5 moves before September 15
Five mid-year moves to run before the September 15 estimated-tax date under the new OBBBA rules.
Read the guide →01R&DSection 174A R&D expensing and the 2022–2024 refund deadline
How Section 174A restores R&D expensing — and the refund window for 2022–2024 you may still be able to claim.
Read the guide →02DEPRECIATIONBonus depreciation in 2026: how to spend $50K before December 31
Bonus depreciation is back; how founders time year-end purchases to capture the deduction.
Read the guide →03QBIQBI 199A phase-out math: keeping your 20% deduction above $200K
The phase-out math for keeping the 20% QBI deduction intact as income rises.
Read the guide →04Entity, Compensation & Retirement Structure
S-corp reasonable compensation in 2026
Setting a defensible S-corp salary in 2026 without overpaying payroll tax or triggering scrutiny.
Read the guide →01RETIREMENTThe SECURE 2.0 Roth catch-up trap for solo 401(k) owners
The new SECURE 2.0 Roth catch-up rule and the trap it sets for solo 401(k) owners.
Read the guide →02HSAUsing an HSA as a stealth triple-tax retirement account
Why an HSA can act as a triple-tax-advantaged retirement account for founders.
Read the guide →03HEALTHCAREThe ACA subsidy cliff: 5 income levers for founders
Five income levers to manage the ACA subsidy cliff when your income is lumpy.
Read the guide →04Acquisitions, Exits & Severance
Laid off to LLC: the 60-day checklist for turning severance into a business
A 60-day checklist for turning a layoff and severance into a funded business start.
Read the guide →01NEGOTIATIONSeverance negotiation: keep 6 extra months of runway
How to negotiate severance to add months of runway before going solo.
Read the guide →02FINANCINGSBA 7(a) financing stack for acquisitions: rates and real costs
The SBA 7(a) financing stack for acquisitions — real rates and all-in costs.
Read the guide →03ACQUISITIONBuy a boomer business with 10% down: the SBA 7(a) playbook
Buying an established "boomer" business with as little as 10% down via SBA 7(a).
Read the guide →04ACQUISITIONRecession as opportunity: acquiring a cash-flowing business
Why a downturn can be the best time to acquire a cash-flowing business.
Read the guide →05EXITSaaS exit math: engineering your way to a higher multiple
The levers that move a SaaS valuation multiple when you plan to sell.
Read the guide →06METRICSChurn math: how 5% vs 3% reshapes your timeline
How a couple of points of churn reshape revenue, valuation, and your timeline.
Read the guide →07Money Mindset & Cash-Flow Discipline
Recession signals that matter more than headlines
The few recession signals worth watching past the headlines.
Read the guide →01COSTSHow founders audit SaaS subscriptions and cut software costs
A repeatable way to audit SaaS spend and cut software costs without breaking workflows.
Read the guide →02DECISIONShould I pay off debt or invest in 2026? The calm decision tree
A calm decision tree for choosing between paying down debt and investing.
Read the guide →03INVESTINGS&P 500 index fund confusion: the beginner mistake
The common beginner mistake when buying S&P 500 index funds — and the fix.
Read the guide →04HABITSWealthy habits that actually move the math
Which "wealthy" habits actually change the numbers and which just sound smart.
Read the guide →05BEHAVIORWhy tracking every expense makes you worse with money
Why obsessive expense-tracking can backfire, and what to do instead.
Read the guide →06Don't miss the next founder-finance playbook.
Weekly, sourced guidance on taxes, money, and building wealth as a founder.