Learn how business owners have structured sales, succession plans, and exit transactions to minimize capital gains taxes, defer recognition, and protect generational wealth.
20 highlighted engagements showcasing proven exit, sale, and succession strategies for business owners.
A technology startup founder sold their C-Corp shares for $12M after holding qualified small business stock for over five years. IRC Section 1202 allowed exclusion of $10M in capital gains, resulting in $2M in federal tax savings on the transaction.
A manufacturing business owner sold their company for $5M and structured the transaction as an installment sale under IRC 453. Spreading the $3.2M capital gain over ten years kept the seller in lower tax brackets each year, saving $380,000 compared to a lump-sum sale.
A family-owned distribution company with 45 employees established an Employee Stock Ownership Plan, selling 100% of shares to the ESOP for $8M. The seller deferred capital gains through IRC 1042 rollover, and the company became tax-exempt as a 100% ESOP-owned S-Corp.
Our team modeled both asset sale and stock sale structures for a $4.5M business transaction. The negotiated asset sale with optimal purchase price allocation saved the seller $85,000 in ordinary income tax while giving the buyer $125,000 in additional depreciation deductions.
Prior to selling a $6M business, the owner contributed shares to a charitable remainder unitrust. The CRT sold the shares tax-free, invested the full proceeds, and provided the owner with annual distributions for 20 years while generating a $540,000 charitable deduction.
A business owner transferred ownership of a $3M company to their children through a two-year GRAT, paying the required annuity from business cash flow. The strategy moved the business out of the owner's estate with minimal gift tax exposure, saving an estimated $450,000 in future estate taxes.
Married co-founders who each held qualifying C-Corp shares for over five years each claimed the $10M IRC 1202 exclusion upon sale. The combined $20M exclusion eliminated $4.7M in federal capital gains taxes on the transaction.
A parent sold their $2M business to an adult child using an installment sale with IRS-compliant AFR interest rates. The structure spread the gain over fifteen years while transferring ownership immediately, saving $180,000 in taxes versus an outright sale.
After selling a business for $4M with a $2.5M capital gain, the seller reinvested the gain into a qualified Opportunity Zone fund within 180 days. The investment deferred the original gain and, if held for ten years, will eliminate taxes on the new investment's appreciation.
A three-partner medical practice valued at $6M implemented a cross-purchase buy-sell agreement funded with life insurance. The structure ensured surviving partners received a stepped-up basis in the purchased interest, saving an estimated $280,000 in future capital gains taxes.
A C-Corp owner sold 30% of shares to an ESOP and elected IRC 1042 rollover treatment, reinvesting proceeds into qualified replacement property within 12 months. This deferred $1.2M in capital gains indefinitely, saving $285,000 in the year of sale.
In a $3M business sale, our team negotiated a $200,000 post-sale consulting agreement for the seller. This reallocated a portion of the purchase price from capital gain treatment to ordinary income spread over two years, reducing the seller's NIIT exposure and saving $52,000.
Anticipating a business liquidation, the owner contributed 25% of their appreciated C-Corp shares to a charitable remainder trust. The CRT received the liquidation proceeds tax-free, and the owner received a $320,000 charitable deduction while retaining income rights for life.
A business owner restructured their $5M company into a family LLC and gifted minority interests to children. The lack of marketability and minority interest discounts reduced the taxable gift value by 35%, saving $650,000 in gift and estate taxes on the transfer.
A 72-year-old business owner sold their company to a key employee using a self-canceling installment note (SCIN). The note's terms provided a premium for the cancellation feature, and upon the owner's passing, the remaining balance was canceled without triggering estate tax.
Our team identified that an LLC taxed as a partnership could convert to a C-Corp and qualify for QSBS treatment on future appreciation. After five years, the founders sold for $8M and excluded $5.2M in post-conversion gains from federal taxation.
In a $7M business sale, our team negotiated the purchase price allocation to minimize goodwill assigned to personal goodwill taxed at capital gains rates versus covenant not to compete taxed as ordinary income. The allocation shift saved the seller $68,000.
A business owner sold their $4M company to an intentionally defective grantor trust in exchange for a promissory note. The sale froze the value in the estate, future appreciation passed to heirs tax-free, and the owner paid income taxes on the trust's earnings, further reducing the estate.
A business sold for $3M upfront plus a $1.5M earnout tied to three years of performance targets. Our team structured the earnout as an open-transaction, deferring $900,000 in contingent capital gain until the earnout payments were actually received, saving $135,000 in the sale year.
A profitable S-Corp with $2M in annual net income transitioned to 100% ESOP ownership. Because an S-Corp owned entirely by an ESOP is exempt from federal income tax, the company saved $480,000 annually in taxes, redirecting those funds to employee retirement accounts and business growth.
Whether you are selling, transferring to family, or transitioning to employees, our team structures exits to minimize taxes and maximize your after-tax proceeds.
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