Reactive tax work
You find out the tax bill in March — after the year is locked. The planning window closed in December.
For business owners
CPA-led tax and wealth strategy for business owners.
We coordinate tax planning, exit decisions, and investment strategy before costly mistakes happen — so the numbers on your K-1, your cap table, and your portfolio all tell the same story.
- CPA-led
- Tax strategy with the numbers, not around them
- Fiduciary
- Investment advice aligned with your tax plan
- Integrated
- One team across tax, wealth, and exit
The problem
Your CPA and your advisor aren’t talking.
Most business owners have a tax preparer who files what already happened and a financial advisor who manages a portfolio in isolation. Neither is in the room when the decisions that actually move the needle get made.
Disconnected portfolio
Investment allocations ignore your concentration in the business, pending sale proceeds, or entity-level income.
Exit surprises
A letter of intent arrives and suddenly structure, basis, and state residency all matter — with weeks, not years, to plan.
Two sets of advice
Your CPA says one thing, your advisor says another, and you end up translating between them at your own expense.
Who we help
Owners whose tax and investment lives can’t be managed in separate rooms.
- 1
Operating business owners
$2M–$50M revenue companies where the owner still drives the P&L and the tax picture.
- 2
Founders approaching an exit
12–36 months from a sale or recapitalization, where structure and timing are still on the table.
- 3
Post-exit families
Liquidity event complete, now coordinating investment strategy, trusts, and ongoing tax planning.
Services
Three practices. One coordinated plan.
Through Reese CPA
Tax Planning
Proactive, multi-year tax strategy for owner-operators: entity structure, compensation mix, R&D and cost segregation, state residency, and year-end planning tied to the actual books.
- Entity & comp structure
- Year-round planning
- Federal + multi-state
Through Measured Risk Portfolios
Wealth Advisory
Fiduciary investment management that accounts for concentrated business ownership, deferred liquidity, and the tax profile your CPA is already building against.
- Tax-aware portfolios
- Concentration planning
- Trust & estate coordination
Joint engagement
Business Exit Planning
A coordinated exit runway — from deal structure and pre-sale entity moves to post-close reinvestment and multi-year tax smoothing — so the number on the LOI is close to the number you keep.
- Pre-LOI structuring
- Installment & QSBS analysis
- Post-close capital plan
Exit tax calculator
Estimate what an exit actually nets you.
Adjust the inputs below to see a simplified federal and state tax estimate for three common exit structures. This is an educational illustration — not tax or investment advice.
Your numbers
Estimate
Estimated gain
$7,300,000
Total estimated tax
$2,852,840
Net proceeds
$5,647,160
Effective rate on sale price
33.6%
Federal LTCG (20%)$1,241,000
NIIT (3.8%)$235,790
Federal ordinary (37%)$405,150
State$970,900
Planning flags
- California applies an additional 1% mental health surtax over $1M — not modeled here.
Structure comparison
Asset sale
$2,852,840
Net: $5,647,160
Effective: 33.6%
Assumes 15% ordinary allocation.
Stock sale
$2,708,300
Net: $5,791,700
Effective: 31.9%
No ordinary allocation; QSBS if toggled.
Installment
$2,852,840
Net: $5,647,160
Effective: 33.6%
Same total tax, spread over 5 yrs.
Educational estimate only. This calculator uses simplified assumptions: top federal LTCG rate of 20%, NIIT 3.8%, federal ordinary 37%, California 13.3% (other states as shown above). It ignores AMT, state-specific surtaxes, phase-outs, deductions, credits, and the full QSBS rules. Figures are for illustration and do not constitute tax, legal, or investment advice. Consult a qualified CPA and advisor before acting on any exit decision.
MR
Matt Reese, CPA
Founder, Reese Tax & Wealth
- — Licensed CPA, active practice
- — Owner-operator tax specialist
- — Investment Advisor Representative
About Matt
A CPA who also sits on the investment side of the table.
Matt built Reese Tax & Wealth after a decade of watching the same pattern repeat: owners getting tax advice that ignored their portfolio, and investment advice that ignored their K-1. The planning that mattered most — the exit, the reinvestment, the multi-year smoothing — lived in the gap between the two.
Today he leads tax strategy through Reese CPA and coordinates investment advisory through Measured Risk Portfolios, so owner-operators can get both sides of the conversation from one team that actually talks to each other.
10+ yrs
CPA practice
Owner-led
Client focus
Fee-based
Advisory model
How it works
Four steps from intro call to ongoing plan.
- Step 01
Intro call
30 minutes to understand your business, your timeline, and where tax and investment decisions are being made today.
- Step 02
Diagnostic
We review returns, entity structure, and portfolio. You receive a written snapshot of gaps and the two or three highest-value moves.
- Step 03
Coordinated plan
Tax work moves to Reese CPA; advisory moves to Measured Risk Portfolios; you get one integrated calendar and one team.
- Step 04
Ongoing quarterly cadence
Quarterly planning check-ins tied to real numbers, not year-end surprises. Exit work layers in when the timeline activates.
Resources
Short, useful reading for owners in planning mode.
Asset sale vs stock sale: what owners actually pay
A plain-English comparison of how each structure taxes the same exit — and why buyers and sellers usually want opposite things.
ReadCalifornia tax when selling a business
How California treats the gain on a business sale, what residency triggers, and where planning still moves the number.
ReadGoodwill and the tax on selling a business
Personal vs enterprise goodwill, why the allocation matters, and how it shows up on the final tax bill.
Read