Selling or Swapping a Life Insurance Policy Can Make the Death Benefit Taxable
Under IRS Section 101(a)(2), selling a life policy for value makes the death benefit taxable above your cost — five exceptions decide if you owe.
#succession-planning
Succession Planning
Strategies for transferring business ownership and leadership to ensure long-term continuity
Farm Succession Planning: How to Pass the Land, the Equipment, and the Management to the Next Generation Without Splitting the Family
Only 23% of family farms have a succession plan. Transfer management first, use LLC interests plus IRS Sections 2032A and 6166, and keep the farm intact.
Your Beneficiary Designations Override Your Will: The Audit Every Business Owner Should Run
A beneficiary form beats your will. Audit every 401(k), IRA, life policy, POD and TOD account for missing contingents, ex-spouses and minors.
Concentrated Stock Risk: When Your Business Is Most of Your Net Worth
About 70% of a business owner's wealth sits in the business; measure the ratio, then diversify with staged sales, Section 1202 QSBS, and outside accounts.
Selling the Family Business to Your Children Without Handing the IRS a Second Payday
An IRS Section 453 installment sale spreads the gain across your retirement, while $19,000 annual gifts and 20-40% valuation discounts move value tax-free.
Stock Sale vs. Asset Sale: A Small Business Seller's Guide to the Tax and Liability Trade-Offs
In a stock sale the seller reports one capital gain and the buyer inherits every liability; in an asset sale the price is allocated across seven Form 8594 classes, so depreciation recapture, inventory, and C corporation double taxation convert much of the gain to ordinary income. Here is how each structure taxes the seller, what the 338(h)(10) election and personal-goodwill carve-out change, and which liabilities follow you past closing.
Passing Your House to Your Kids Without Probate: How Transfer-on-Death and Lady Bird Deeds Work
A transfer-on-death deed names a beneficiary for your house the way you would for a bank account — recorded now, revocable any time, effective only at death. More than 30 states plus DC authorize one; Florida and Michigan use the Lady Bird (enhanced life estate) deed instead. Here is what each does, how to record one correctly, and the filing errors that send families back into a 9-to-18-month probate.
The Small-Business Retirement Wave: How to Build an Exit Buyers Will Actually Pay For
A March 2026 survey of about 1,000 U.S. small business owners found 40% expect to retire within a decade while 70% have no formal succession plan. Buyers price a small business on seller's discretionary earnings times a 2x–4x multiple, discounted for owner dependency, customer concentration and unreliable books. This guide lays out a six-part, three-to-five-year plan — two target numbers, three years of clean financials, operational replaceability, risk de-concentration, a deliberate exit path (third-party sale, family succession, management buyout or ESOP), and a reverse-built timeline with a CPA and attorney — plus the three mistakes that shrink exits.
Holding Company vs. Operating Company: When Two Sets of Books Beat One
A holding company owns the assets and an operating company runs the business, but the liability firewall between them holds only if each entity keeps its own bank account, its own ledger, and documented intercompany loans, leases and settlements. This guide covers when the two-company structure pays off for a small business, when it is pure overhead, how to book intercompany transfers correctly, and why consolidated financial statements differ from the 80-percent-ownership consolidated tax return.
The Succession Planning Perception Gap: Why 65% of Small Business Owners Have No Exit Plan — and How to Build One Buyers Will Trust
40% of small business owners plan to retire within 10 years but 70% have no formal succession plan and only 8% are fully prepared; Revenued finds 59% of successors assume a plan exists while only 35% of owners have one — this guide explains the 24-point gap, valuation methods, clean-book QofE prep, and a 12-month exit plan to make your business lending-ready.
Phantom Stock Plans for Small Businesses: Reward Key Employees Without Giving Away Ownership
A phantom stock plan grants key employees hypothetical units that track company value and settle in cash — no shares issued, no dilution, no voting rights. Payouts are ordinary income subject to FICA when paid, the employer deducts them in the same year, and cash-settled awards are liability awards remeasured at fair value each reporting period. Paying within 2½ months after the year units vest satisfies Section 409A's short-term deferral exemption; a two-to-three-participant plan typically costs $4,000–$10,000 to launch.
The Silver Tsunami Is Here: How to Buy or Sell a Business in the $5 Trillion Great Ownership Transfer
About 6 million U.S. small and mid-sized businesses will change hands by 2035 as baby boomer owners retire, and McKinsey estimates more than 1 million of those are sellable, representing up to $5 trillion in enterprise value — yet only about 35% of owners have a succession plan. This guide covers the three-year seller timeline, how valuation multiples of 2x to 4x SDE are earned, SBA 7(a) and seller-financing structures for buyers, due diligence, and the bookkeeping habits that separate a sellable business from one that quietly closes.