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ESOP (Employee Stock Ownership Plan) — Tax-Free Exit for Founders

Sell your C-corp to an ESOP + §1042 rollover into 'qualified replacement securities' = 0% federal tax on sale.

Overview

Founder sells 30%+ of C-corp to an ESOP (leveraged with bank/seller financing), then invests proceeds in Qualified Replacement Property (QRP — publicly-traded U.S. stocks/bonds) within 12 months for full §1042 gain deferral. If QRP held until death, gain permanently escapes tax via step-up basis. Alternative: sell 100% to ESOP as S-corp — ESOP pays NO federal income tax on its share (100% ESOP = 100% tax-free operating business). Complex ($200K+ setup), best on $5M+ EBITDA.

Best fit
C-corp founders exiting $10M+ businessesEmployee-legacy-minded ownersEstate-planning founders
Estimated impact
0% federal capital gains on business sale

Click Generate advisory deep dive for mechanics, IRC citations, a step-by-step execution plan, a worked numeric example on your profile, costs, risks, and this-week actions.

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