Rollover Equity in a Business Sale: Topics to Review With Your Advisors Before Signing
Rollover equity looks like a small line item on a term sheet. It changes what your exit actually looks like. Topics to review with your advisors before signing.
Ideas for sharper advisor conversations.
Read practical guides for business sales, real estate exits, equity liquidity, windfalls, and other moments where the right advisor questions matter.
tax planning
1031 exchange
business sale
advisor-coordination
exit planning
financial advisor
liquidity event
real estate
capital gains
equity compensation
Depreciation Recapture in a 1031 Exchange: Topics to Review With Your Tax Advisor Before Your Replacement Property Closes
A 1031 exchange defers depreciation recapture rather than erasing it. Here are the coordination topics to walk through with your tax advisor and QI before closing.
Inheriting a Brokerage Account With Embedded Capital Gains: Topics to Review With Your Tax Advisor
An inherited brokerage account with embedded gains follows tax rules that surprise most heirs the first time. Here are the topics worth raising with a tax advisor.
Disqualifying Disposition of ISOs: Topics to Review With Your Tax Advisor Before Selling Within the Holding Period
Selling ISO shares before the holding periods end changes the tax character. These are the questions worth raising with your tax advisor first.
Advisor Succession Planning: Topics to Clarify Before Engaging
A long advisor relationship may outlast the advisor's career. Here are the succession and continuity topics to raise during the engagement conversation.
Management Retention Agreements During a Business Sale: Topics to Review With Your Advisors
Management retention agreements look simple on the surface. The tax, legal, and financial layers underneath often need three different advisors to untangle.
Estimated Tax Payments After a Liquidity Event: Topics to Review With Your Tax Advisor to Avoid Underpayment Penalties
A liquidity event often produces tax bills that withholding does not cover. These are the questions worth raising with your tax advisor about estimated payments.
Section 83(b) Election: Topics to Review With Your Tax Advisor Before the 30-Day Window Closes
A Section 83(b) election has a strict 30-day filing window and meaningful long-term tax consequences. Here are the topics to review with a tax advisor before deciding.
State Residency Considerations After a Liquidity Event: Topics to Coordinate With Your Tax and Estate Advisors
A guide to state residency questions that come up after a liquidity event and the topics worth coordinating with your tax and estate advisors.