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Private Wealth Managementwilliamblair.com Pre- and Post-TransactionPlanning Checklist When selling a business,owners often focus on closingthe deal. An additional focuson personal wealth planningopportunities could result insignificant savings on income,gifts, and estate taxes. Proactive pre-and post-transaction wealth planning can affectyour strategy as you consider the sale of your business. Factors to consider include: Liquidity and cash flow planningWealth transfer objectivesRisk managementInvestment planningCybersecurity Pre-Transaction Considerations Liquidity and Cash Flow Review structure and timing of the transactionReview consideration received: cash, equity, earn-outs, or a combinationReview income implications: ordinary income versus capital gainsConsider deferred compensation optionsAnticipate and plan for significant tax exposure and/or unique tax situations(net investment income tax, gift tax, foreign tax, multi-state income tax, etc.) Wealth/Liquidity Transfer Valuation - Is there an opportunity to maximize wealth transfer pre-transaction?Review current estate plan and asset flows to heirsEstablish timeline, amounts, and other considerations in transferring wealthto heirsDetermine optimal timing of asset transfers relative to the transactionBalance executives’ lifetime needs with wealth transfer goals Risk Management Outline current risk exposures and identify if they are covered by insuranceor self-insuredTitle assets to protect from creditorsConduct review of concentrated wealth hedging and monetization strategies:stock, cash, equity compensation, or business exposure Investment Planning Review current overall asset allocation and future allocation considerationspost-liquidityTest and review concentrated asset class exposuresReview income considerations and asset location for tax efficiencyIdentify capital loss opportunities versus gains received in liquidity eventReview current and anticipated portfolio income and taxation characteristics Private Wealth Managementwilliamblair.com Personal & Cyber Security Preparation Risk Management Personal security auditCybersecurity audit and preliminary precautionsSocial media and internet monitoring(pre and post transaction)Review steps you can take to minimizephilanthropic and monetary attention Fiduciary reviewInsurance review; retire obsolete or unnecessarypolicies, cover new exposed risksPersonal security review (personal information,cybersecurity, physical security, etc.)Identify the largest risk exposures and how to efficientlytransfer that risk Post-Transaction Considerations Investment Planning Liquidity and Cash Flow Escrow estimated tax payments after factoring intax strategyRe-create a paycheck with portfolio income vs.income from the businessCash flow planning: income versus expensesLarge purchase considerations (new real estate,homes, boats, planes, etc.)Determine current/future role in the company: equityrollover modeling, future income, earn-outs, etc. Transaction proceeds deployment, allocation, incomegeneration, and related tax exposureOngoing management and reporting of investmentsand private investment opportunitiesEstablish aggregated total balance sheet reporting Wealth/Liquidity Transfer Protect the legacy you leave your familyReview estate planning considerations given newfinancial picture or future plansQuantify surplus wealth versus lifetime capital needsCharitable considerations post-liquidity event (usinglower basis and more efficient assets)Synchronize charitable income tax benefits with theincreased tax exposure created by the transaction August 2025 This content is for informational and educational purposes only and not intended to provide or should not be relied upon for legal, tax, accounting, or investment advice or arecommendation to buy or sell any security. Investment advice and recommendations can be provided only after careful consideration of an investor’s objectives, guidelines,and restrictions. The factual statements herein have been taken from sources we believe to be reliable, but such statements are made without any representation as to accuracyor completeness. Opinions expressed are current opinions as of the date appearing in this material only. These materials are subject to change, completion, or amendment fromtime to time without notice, and William Blair is not under any obligation to keep you advised of such changes. This document and its contents are proprietary to William Blair& Company, L.L.C., and no part of this document or its subject matter should be reproduced, disseminated, or disclosed without the written consent of William Blair & Company,L.L.C. Any unauthorized use is prohibited. “William Blair” is a registered trademark of William Blair & Company, L.L.C.