Owner Transition Planning

Most owners are off by 30% on what they actually need post-transaction. Build the personal cash-flow model before you build the deal model.

• Annual lifestyle spend, post-tax, in retirement (be honest)
• Healthcare cost without a company plan
• Capital gains tax on the transaction (federal + state)
• Charitable and family gifting plans
• Reserve for the next thing you'll do — most owners don't actually retire

Once a transaction is 'reasonably anticipated,' the IRS deems gifts of stock to be valued at the deal price — not pre-deal valuation. The planning windows close fast.

• Engage an estate attorney 18+ months before any sale process
• Consider GRATs, IDGTs, or charitable trusts while valuation is lower
• Use lifetime gift exemption thoughtfully (current and future)
• Coordinate with your CPA — tax planning ≠ legal planning
• Document business purpose for any restructuring (defense against step-transaction)

The identity work is the part most owners postpone until it's a crisis. The conversations to have now — with your spouse, your kids, and yourself.

• What does a good Tuesday look like at 11am, six months after closing?
• What relationships in your life depend on you being 'the owner'?
• What's the next thing — board roles, investing, philanthropy, a smaller business?
• How will your spouse experience your presence at home full-time?
• What story do you tell yourself about why you sold, and is it true?