Where we add the most value
Entity and exit structure
C-corporation versus S-corporation, the Section 1202 QSBS exclusion and its holding-period clock, installment sales, and rollover equity. For stock issued after July 4, 2025, QSBS can exclude up to $15 million of federal gain per issuer, with partial exclusions after three and four years; older stock keeps the $10 million cap and the five-year all-or-nothing rule. The decision has to be made years ahead, which is why we start here.
Retirement plan design
401(k) with profit sharing, cash balance plans, and the trade-off between owner deductions and employee cost. For an owner in their 50s with stable profits, a cash balance plan layered on a 401(k) can turn a six-figure tax bill into a six-figure retirement contribution.
Depreciation and real estate
Whether to hold real estate inside or outside the operating company, when a cost segregation study pays for itself under 100% bonus depreciation, and how depreciation recapture affects a later sale. See Is cost segregation still worth it?
Risk and insurance structure
Buy-sell agreement funding, key-person coverage, and when a captive insurance arrangement is worth its complexity. We do not sell insurance, so the recommendation is only about whether you need it.
Concentration and the years before a sale
Diversifying outside the business in a Personal Index Portfolio managed within a written tax budget, pre-sale gifting and estate moves that work better before a valuation jump, and a plan for the proceeds so a liquidity event does not become a tax event twice.
How an engagement runs
- Discovery. We read the returns, the operating agreement, the buy-sell, and the retirement plan documents, and we talk with your CPA.
- Analysis. We model the alternatives with your numbers: entity change or not, plan design, depreciation timing, sale structures.
- Written recommendations. A plan your CPA and attorney can implement, with the trade-offs stated plainly.
- Implementation and follow-through. We coordinate the professionals, track deadlines, and revisit the planning as the business and the law change.
Case studies and reading
- Case study: the anesthesiology group that saved $1.2 million
- Case study: how a business pivot almost cost a founder $2.4 million
- The $15 million exit mistake: Section 1202 QSBS
- Planning for a liquidity event
- Top 7 tax planning tips for business owners
Ready to start early? Schedule a meeting or ask your CPA to reach us through our CPA Partners page.
