Entity and S-corp comp
The single biggest recurring lever for most owner-operators. We build a defensible reasonable compensation analysis and re-run it as the business grows.
For owner-operators
Business owner tax planning, built to run year-round.
The tax return tells you what already happened. Planning decides what the next one looks like. We run both — entity structure, owner comp, quarterly estimates, year-end moves, and the coordination with the long-term portfolio that most owners never get.
The gap
A tax preparer files. A tax plan changes the number.
Most owners have someone who files a return once a year. Far fewer have someone who owns the rhythm of decisions that shape the return before it’s filed — the entity, the comp, the estimates, the retirement plan, the allocation at year-end.
Quarterly estimates
Safe-harbor vs projection-based estimates, coordinated with distributions so cash actually matches what the IRS and FTB expect.
Retirement plan architecture
Solo 401(k), SEP, SIMPLE, or a cash balance / defined benefit layer — matched to profit, age, and staff. This is where high-earning owners shelter the most.
Year-end moves
QBI optimization, depreciation elections, accountable plans, PTET, and the timing of major expenses or distributions — run before December, not in April.
What’s inside
The pieces of a business owner tax plan.
Entity structure review
Sole prop, LLC, S-corp, partnership, or C-corp — we review the current election against your revenue, number of owners, exit plans, and state exposure, and flag when a change actually pays back.
S-corp tax planningOwner compensation & payroll
Reasonable compensation built on industry data, owner duties, and revenue. Documented so the decision holds up — and re-examined as the business scales.
How we set S-corp compQuarterly planning cadence
A real check-in every quarter, tied to current-year books. Estimates adjusted, entity decisions revisited, and a short list of moves for the next 90 days.
Year-end planningWealth coordination
Distributions coordinated with the long-term portfolio, retirement plan design, and concentration from the business itself — through Measured Risk Portfolios.
Tax & wealth planningEquity comp coordination
RSUs, ISOs, NSOs, ESPP, and concentrated founder stock — multi-year planning that sits alongside the business and not in isolation.
RSU & equity compExit & liquidity planning
When a sale or partner buyout is actually on the table, we run the pre-LOI structure, the sale mechanics, and the post-close reinvestment plan.
Selling a businessThe rhythm
A quarterly cadence, not a March scramble.
Tax planning has real windows. Miss them and the decision is already made. This is what an owner’s year looks like when someone owns the calendar.
Q1
Prior-year return and extension call. Entity and owner-comp decision set for the year.
Q2
Mid-year projection and estimate check. Retirement plan funding plan confirmed.
Q3
Fall planning window — QBI, depreciation, entity elections, and PTET considerations.
Q4
Year-end moves locked in before December 31, including distribution and comp trueups.
The bigger picture
Tax is the wedge. Wealth is the engine.
A strong tax plan keeps the business efficient year to year. But the real compounding happens when distributions and owner income are converted into an investable balance sheet — and when the portfolio is coordinated with the entity, the concentration, and the tax picture.
- Retirement plan design that matches profit and owner age
- Distribution timing coordinated with portfolio cash needs
- Concentration management for owners heavy in one business or one stock
- Estate, trust, and succession coordination as wealth grows
Get started
Run your business off a plan, not a March surprise.
Start with a business-owner review. Two returns, the entity, the comp decision, and the portfolio — reviewed end to end, with a short list of moves worth making this year.
Educational information only. Not tax, legal, or investment advice. Tax services through Matt Reese, CPA; investment advisory through Measured Risk Portfolios.