Retirement & Business Exit

Transitioning out of a business or real estate portfolio you spent years building. How you exit — and when — determines how much you actually keep.

Start Planning Earlier Than You Think

The best exits are planned 2–5 years in advance. Businesses that are dependent on the owner, have messy financials, or lack documented systems sell for less — or don't sell at all. Giving yourself time to clean things up creates a meaningfully better outcome.

Real estate portfolios have similar considerations: debt structure, depreciation recapture, 1031 exchange eligibility, and whether to sell all at once or in tranches all affect net proceeds significantly.

Business Exit Options

• Sell to a third party: Market sale — highest potential value but requires preparation
• Sell to employees (ESOP): Tax-advantaged, preserves culture, complex to structure
• Family transfer: Gift or sale to children — estate planning and valuation critical
• Seller financing the sale: Spread income over years, reduce immediate tax burden
• Close and liquidate: If no buyer exists — recover asset value and wind down

Real Estate Portfolio Exit

• 1031 exchange: Defer capital gains by rolling into a new property
• Installment sale: Spread gain recognition over years via seller financing
• Delaware Statutory Trust (DST): Exchange into a passive ownership structure
• Hold and pass down: Step-up in basis at death eliminates accumulated gains

What I Look At

• What's the business or portfolio actually worth today?
• What would maximize after-tax proceeds?
• What's the realistic buyer profile and deal structure?
• How does the exit align with your income needs in retirement?

Thinking about your exit? Let's start mapping out what that actually looks like.