IPO Lockup Expiration: Topics to Clarify With Your Advisors Before Your Shares Unlock
When your IPO lockup ends, the tax timing and planning decisions around your shares benefit from early advisor input. Here are the key topics to address.
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
business sale
exit planning
wealth management
1031 exchange
capital gains
estate planning
financial advisor
equity compensation
fiduciary
Asset Sale vs. Stock Sale: Questions to Review With Your Advisors
Business owners exploring a sale encounter an early decision about transaction structure. This overview reviews the key tax, liability, and operational topics to discuss with your advisors when considering an asset sale versus a stock sale.
1031 Exchange Identification Period: What to Clarify Before the 45-Day Window Closes
The 45-day identification window leaves no room for uncertainty. Clarifying the rules, the written requirements, and the interaction with your tax return deadline before the relinquished property closes can prevent the mistakes that disqualify exchanges.
Understanding Earnout Structures in a Business Sale
Earnouts allow buyers and sellers to bridge valuation gaps, but they transfer risk to the seller in ways that are not always obvious at signing. Here is what to review with advisors first.
Tax Planning for Concentrated Stock Positions
Concentrated stock positions - whether from equity compensation, a business sale, or inheritance - require careful tax planning before any diversification. Here is what advisors typically review.
SPAC Mergers: What Equity Holders Need to Review Before the Vote
When a private company announces a SPAC merger, employees and early investors face a set of decisions very different from a traditional IPO. Here is what to review before the vote.
Secondary Sales of Private Company Stock: Topics to Review
For employees and investors in private companies, secondary sales offer a path to liquidity outside of an IPO or acquisition. Here are the topics to review before pursuing one.
Reverse 1031 Exchanges: What Real Estate Investors Need to Know
A reverse 1031 exchange inverts the typical order - acquire first, sell second - but the tax rules, financing constraints, and timeline are significantly more complex than a forward exchange.
Inheriting a Business: Financial Questions to Address First
Inheriting a business creates decisions that are more time-sensitive than most inherited assets. Here are the financial, legal, and operational questions to address before taking any action.