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Tax Optimization Strategies for $10M–$50M Business Exits

by: Chapman SymePublished on: 03/20/2026

From home office to obsolete inventory, discover eleven tax breaks that regularly go unclaimed in small businesses—and why the right ones also improve your valuation before a sale. Chapman Syme from Blackland Advisors.

small business tax deductionsbusiness tax breakshome office deductionSection 179 depreciationbusiness owner tax planningretirement plan deductiontax credits small businessEBITDA tax planninglower middle market taxenergy efficiency tax credittax deductions small business owners misshome office deduction regular vs simplified methodvehicle expense deduction business ownerSection 179 bonus depreciation small businessself-employed health insurance premium deductionnon-qualified deferred compensation tax deductionobsolete inventory write-off timing business salebad debt deduction small businessstartup cost deduction new businessenergy efficiency tax incentives small businessSection 179D commercial building deductionhow depreciation affects EBITDA business valuationretirement plan contribution deduction small businessSEP-IRA vs Solo 401k business ownerhow tax planning affects business sale valuationinventory write-off timing before business saleemployer educational assistance exclusion Section 127business interest deduction Section 163j limitationtax breaks lower middle market business ownershow to connect tax planning to exit planningchapman syme
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