The Moment
You sold your business — the company you built for years or decades — for $250,000 to $1,000,000. The proceeds are in your account. The emotions are complex: relief, pride, loss of identity, excitement, and uncertainty.
At this level, the financial decisions are consequential enough that professional guidance pays for itself many times over. A CPA who saves you $30,000 in taxes costs $2,000. A financial advisor who prevents a $100,000 investing mistake costs $1,500. The ROI on professional help is enormous.
The 90-Day Plan
Days 1-30 — Secure and assemble. Park proceeds in a HYSA or short-term Treasuries. Stay under $250,000 per bank for FDIC insurance (spread across 2-4 banks if needed). Hire a CPA with business sale experience and a fee-only financial advisor.
Days 30-60 — Tax strategy. Your CPA determines the tax liability based on sale structure: - Asset sale vs stock sale (different tax rates for different asset classes) - Capital gains treatment (long-term if business held 1+ year: 15-20% federal) - Installment sale provisions (if receiving payments over time) - QSBS exclusion (if C-Corp held 5+ years, up to $10M in gains may be excludable) - State taxes (vary from 0% to 13%+)
Days 60-90 — Deploy. - All consumer debt: eliminated - Emergency fund: 12 months (business owners often have variable post-sale income) - Max all retirement accounts - Diversified investment portfolio in taxable brokerage - Estate plan: will, trust, umbrella insurance ($2-5M policy) - Health insurance: ACA marketplace if no employer coverage
The identity transition: Many business owners struggle after selling. The business was not just income — it was purpose, identity, and social structure. Budget time and money for this transition. A business coach or therapist experienced with exits is a worthwhile investment.
Run Your Numbers
Enter your sale proceeds.
$500,000+ Windfall Allocator
What to explore next
- →How do I minimize taxes on my business sale?
- →Do I qualify for the QSBS exclusion?
- →How do I invest $500,000+ from a business sale?
Frequently Asked Questions
Can I retire on $500,000-$1,000,000 in sale proceeds?
At a 4% withdrawal rate: $500,000 supports $20,000/year; $1,000,000 supports $40,000/year. Combined with Social Security ($20,000-$40,000/year), total income is $40,000-$80,000. For modest lifestyles with paid-off housing, this can work. For higher lifestyles or early retirement (before 62), it may be insufficient. Run a detailed retirement projection with your advisor.
Should I start another business?
Wait at least 6-12 months. Post-sale euphoria and identity loss drive many entrepreneurs into new ventures prematurely. If you start another business, allocate a defined amount from the proceeds (10-20% maximum) and invest the rest. This preserves your financial security if the new venture fails.