18 tagged with "Succession Planning"
Strategies for transferring business ownership and leadership to ensure long-term continuity
The Connelly Trap: How a Unanimous Supreme Court Decision Broke Decades of Buy-Sell Agreements—and What Co-Owners Must Do Now
Connelly v. United States, decided unanimously on June 6, 2024, ruled that company-owned life insurance proceeds count toward a deceased shareholder's estate—adding $889,914 in federal estate tax for one Missouri family. This guide explains why redemption-funded buy-sell agreements now backfire and walks through five workable alternatives, including cross-purchase structures, insurance LLCs, and ILITs.
ESOP Section 1042 Rollover: How C-Corp Owners Can Sell to Employees and Defer (or Eliminate) Capital Gains Tax
Section 1042 of the IRC lets a C-corporation owner selling shares to an ESOP defer federal capital gains tax indefinitely — and potentially eliminate it through step-up at death. This guide covers the five qualifying conditions, what counts as Qualified Replacement Property, the floating-rate-note diversification strategy, and the trade-offs founders should weigh against a strategic sale.
Key Person Life Insurance and Section 101(j) Compliance
Key person life insurance pays the company, not the family, when a founder, rainmaker, or specialist dies. IRC Section 101(j) makes the death benefit taxable unless written notice and consent are completed before the policy issues — a step most small businesses skip, turning a $1M tax-free benefit into roughly $600K–$700K after tax.
See-Through Trust as IRA Beneficiary: How Conduit and Accumulation Trusts Work Under the SECURE Act 10-Year Rule
A see-through trust named on an IRA beneficiary form must navigate the SECURE Act 10-year rule. Conduit trusts pass every distribution through to the beneficiary by year ten, while accumulation trusts retain assets but face compressed trust brackets that reach the 37 percent federal rate at just $16,000 of retained income in 2026.
Business Succession Planning: A Complete Guide for Small Business Owners
Learn how to create a business succession plan that protects your legacy. Covers the five main succession options, buy-sell agreements, business valuation, tax planning, and a step-by-step timeline for small business owners.
Estate Planning for Small Business Owners: Protect Your Legacy and Your Business
A complete guide to estate planning for small business owners. Covers trusts, buy-sell agreements, the 2026 estate tax exemption changes, tax-smart transfer strategies, succession planning, and a practical estate planning checklist.