Personal & Business Assessment
Before you build, you test the ground. Every number, relationship, and obligation is mapped.
1.1
Personal Financial Inventory
"Measuring the lot before designing the house"Know exactly what you own, owe, and what your life costs. This is the honest accounting of your personal financial world — separate from the business.
What We Measure
Net Worth StatementAll personal assets minus all liabilities
Annual Lifestyle CostTrue cost including business-paid perks
Estate Plan ReviewWills, trusts, POA, beneficiary designations
Insurance AuditLife, disability, umbrella, buy-sell funding
The Gap Number
Your Non-Negotiable FoundationMinimum post-tax wealth needed to fund your life forever
CEPAAdvisorCPAInsurance
Complete personal net worth statement
Calculate true annual lifestyle cost
Review all estate documents & beneficiaries
Complete insurance coverage audit
Calculate your Gap Number
1.2
Business Health Assessment
"Testing the soil"Diagnostics
Revenue QualityRecurring vs one-time; customer concentration
Adjusted EBITDATrue earning power with add-backs
Owner DependencyCan business run 90+ days without you?
Value Gap
Required Sale Price vs Current ValueHow much value do you need to build?
CEPACFOValuation
Analyze revenue quality & concentration
Calculate Adjusted EBITDA
Score owner dependency
Calculate your Value Gap
1.3
Family & Emotional Readiness
"Who's living in this house?"Alignment
Spouse/Partner AlignmentShared vision, timeline, lifestyle, identity
Children & InheritanceFair vs equal; who gets what
Identity TransitionWhat will you DO after?
Complete spousal alignment conversations
Document each child's role & expectations
Create post-exit purpose plan
Document Inventory
Let's see what you have and what you need
Before we move to the Blueprint phase, we need to take inventory of your current documents. Toggle what you already have — then we'll identify the gaps.
Valuation, Route & Tax Architecture
Get a formal valuation, select your exit route, and build the tax structure that determines how much you keep.
2.1
Valuation & Route Selection
"The appraisal and choosing the style"Valuation
Market ApproachWhat similar businesses sold for
Clean FinancialsAccrual, monthly close, reconciled, no personal expenses
ValuationCFOCPA
Engage valuation professional
Estimate business value range
Select exit route
Model net-after-tax for chosen route
2.2
Tax & Trust Architecture
"Pulling permits — structure = what you keep"Tax Strategies
Entity Structure (C vs S vs LLC)Double tax risk; 5-year conversion window; QSBS only for C-Corps
QSBS (Section 1202)Exclude $15M+ in gains — potentially tax-free (enhanced by OBBBA 2025)
SLAT / IDGT / GRATPre-transaction trust strategies
CPAEstate AttyAdvisor
Review entity structure
Evaluate QSBS eligibility
Establish pre-transaction trusts
Model total tax exposure
2.3
Exit-Route-Specific Requirements
"Each blueprint has unique permits"Each exit route has unique legal, financial, and operational requirements. After selecting your route, review and complete the items specific to YOUR path.
🏢 Third-Party Sale Requirements
M&A Advisor Selection & EngagementInterview 3-5 firms; understand fee structures (Lehman, flat, hybrid)
Data Room Preparation3-5 months to build; 200-500 documents organized
Management Presentation PreparationYour team presents to shortlisted buyers
🔄 PE Recapitalization Requirements
Management Equity Rollover Structure20-40% equity roll; tax-deferred if structured correctly
Employment Agreement & Incentive Plan3-5 year CEO agreement; equity incentive for second bite alignment
👥 Management Buyout Requirements
SBA Pre-QualificationBuyers must qualify 6-9 months before close
Seller Note Terms & SecurityInterest rate, term, covenants, lien position, personal guarantees
🏛️ ESOP-Specific Requirements
Independent Trustee SelectionRequired by ERISA; represents employee interests in the transaction
Section 1042 Qualified Replacement Property PlanningMust reinvest within 12 months; strict rules on what qualifies
S-Corp Election TimingConvert after ESOP sale for entity-level tax exemption
👨👩👧 Family Transfer Requirements
Buy-Sell Agreement UpdateMust reflect the succession plan; sets valuation methodology
Family Council & GovernanceFormal meeting structure; decision rights; conflict resolution
Valuation Discount DocumentationLack of control & marketability discounts; must be defensible
🤝 Merger Requirements
Equity Split NegotiationBased on relative EBITDA, growth, assets, management, and strategic value
100-Day Integration PlanBack-office, technology, customers, culture, communication
Complete route-specific requirements above for your chosen exit
Assemble advisory team (M&A advisor, transaction attorney, tax CPA, wealth advisor, estate attorney)
Interview 3+ candidates for each advisory role
Begin data room document collection (200-500 items)
Design key employee retention plan (stay bonuses, employment agreements)
Prepare confidential employee communication plan
Review all contracts for change-of-control provisions
Update buy-sell agreement to reflect current plan
Architecture Workshop
Build your entity & trust structure
Model your corporate structure in the Structure Lab, then design your estate plan in Life by Design. Take the results to your CPA and attorney for implementation.
Value Build & Business Readiness
12-36 months strengthening what buyers scrutinize. Every dollar here returns multiples at closing.
3.1
Financial & Operational Build
"Level foundation, strong frame"Financial Readiness
Accrual AccountingRevenue when earned, not when cash received
Monthly Close ≤15 daysReconciled books, financials available fast
Operational Value
SOPs, Management Team, Operating SystemDocumented processes, leadership depth, meeting rhythm
Customer Diversification & IP ProtectionNo customer >15%; trademarks filed
Transition to accrual accounting
Implement monthly close process (≤15 days)
Document SOPs (80%+ coverage)
Build management team depth — strong #2 in place
Reduce customer concentration (no customer >15%)
Implement operating system (EOS, Scaling Up, or equivalent)
File IP protections (trademarks, trade secrets, NDA templates)
Update all employment agreements (non-competes, NDAs, IP assignment clauses)
Resolve pending litigation, regulatory, or compliance issues
Complete cybersecurity assessment (increasingly required by buyers)
Audit benefit plan compliance (401k, health, ERISA)
Review all contracts for change-of-control or assignment provisions
Environmental assessment if real estate or manufacturing involved
Wealth & Risk Infrastructure
Invisible systems that protect and channel wealth for generations.
4.1
Wealth Pre-Planning & Risk Architecture
"Plumbing and insulation — ready before the water flows"Before the Wire Hits
Investment Policy StatementWritten rules: allocation, risk, benchmarks
Day One Wire PlanExact destination for every dollar
Reps & Warranties InsuranceReduces escrow, more cash at close
Draft Investment Policy Statement
Create Day One Wire Plan
Establish charitable giving vehicles
Evaluate RWI and D&O tail
Overhaul personal insurance
Transaction Execution & Close
Stage, show, negotiate, survive diligence, close with every dollar accounted for.
5.1
Deal Execution
"Staging, showing, negotiating, closing"Go to Market
CIM, Data Room, Buyer Universe30-60 page brochure, secure doc repository, buyer targeting
LOI, Negotiation, Purchase AgreementAlways model "net to you" — not the headline
Complete CIM and data room (200-500 documents)
Engage investment banker / M&A advisor
Conduct management presentations (rehearse 3-5x)
Evaluate LOIs — model "net to you" for each
Negotiate working capital peg (use trailing 12-month average)
Survive buyer due diligence (respond within 48 hours)
Review reps & warranties line-by-line with counsel
Evaluate RWI insurance to reduce escrow holdback
Analyze Section 280G (golden parachute) exposure
Execute employee communication plan (tiered rollout)
Finalize Day One Wire Plan destinations
Sign Purchase Agreement & Close
Life After Exit
Execute critical financial moves, navigate identity transition, build governance for generations.
6.1
First 90 Days & Stewardship
"Settling in for generations"Critical Actions
Deploy, Fund, Pay Taxes, GovernInvest per IPS, fund trusts, estimated taxes, family meetings
🌳 The Most Important Statistic
70% of family wealth lost by Gen 2 — almost always from communication breakdown, not bad investments. Build governance alongside wealth.
Deploy proceeds per IPS (dollar-cost average over 3-6 months)
Fund trusts & charitable vehicles (DAF, CRT) in sale year
Make estimated tax payments (federal + state) immediately
File gift tax returns (Form 709) if trusts were used
ESOP sellers: complete QRP reinvestment within 12 months
MBO sellers: set up note monitoring & covenant tracking
Purchase D&O and E&O tail insurance (3-6 year tail)
Calendar escrow release date & earnout measurement periods
Track non-compete compliance (know your restrictions)
Execute transition obligations professionally (customer intros, knowledge transfer)
Establish annual family wealth meeting & governance
Create next-gen financial education plan
Honor the 90-day rule: no major decisions for 90 days
30-day check-in: How are you feeling? Journal it.
60-day check-in: Meet with executive coach or therapist
90-day check-in: Review purpose plan — ready for next chapter?
Define & pursue your next chapter 🎉
Legacy Planning
Design where the wealth goes next
You've closed the deal. Now protect and transfer the wealth across generations with trust planning, governance, and an attorney-ready estate plan.