Earnouts appear in 25-40% of lower middle market deals. Learn how they work, when they make sense, the risks sellers face, and how to structure an earnout that actually pays out.
Posts Tagged
‘Exit Strategy’
Tax planning can save or cost you 20-40% of your sale proceeds. Learn asset vs. stock sale structures, capital gains strategies, entity type implications, installment sales, QSBS exclusions, and Tennessee’s no-income-tax advantage.
November 14, 2025
Business Owner, Exit Strategy, Lower Middle Market, Nashville, Selling a Business
Due diligence is where deals get repriced or killed. Here’s exactly what buyers request — organized by financial, legal, operational, insurance, and banking categories — so you can prepare before the clock starts.
October 21, 2025
Business Owner, Due Diligence, EBITDA, Exit Strategy, Lower Middle Market, M&A, Selling a Business
Commercial insurance is one of the most overlooked factors in M&A transactions. Buyers evaluate your coverage as a proxy for operational maturity — and gaps can reprice deals, trigger escrow holdbacks, or delay closing. Here’s what buyers expect and how to prepare.
Selling a lower middle market business typically takes 9 to 18 months from decision to close. Here’s the realistic stage-by-stage timeline — and what accelerates or delays every phase of the process.
Most M&A deals don’t die over price — they die in due diligence. Here are the five issues that consistently kill lower middle market deals, and how to prevent every one of them before you go to market.
September 30, 2025
Business Owner, Due Diligence, EBITDA, Exit Strategy, Lower Middle Market, M&A, Selling a Business
Private equity and strategic buyers evaluate your business through fundamentally different lenses. Understanding which is right for your exit — or why you need both at the table — is one of the most consequential decisions you’ll make as a seller.
Tennessee’s no-income-tax advantage, growing buyer interest, and Nashville’s booming economy make it one of the most attractive states to sell a business. Here’s the complete guide to selling a Tennessee business — from preparation and valuation through closing — for owners with $3M–$50M in revenue.
September 23, 2025
Business Owner, EBITDA, Exit Strategy, Lower Middle Market, M&A, Nashville, Selling a Business
Business, Exit Planning, Industry Insights, Selling Your Business
Most lower middle market businesses sell for 3x-8x adjusted EBITDA. Learn what drives valuation multiples, common mistakes that leave money on the table, and how to position your business for a premium sale price.
A fractional CFO brings senior financial leadership to growing companies without the $300K+ full-time cost. For businesses with $3M-$50M in revenue, this role fills the gap between a bookkeeper who records history and a strategic partner who shapes the future.
September 9, 2025
Business Owner, EBITDA, Entrepreneur, Exit Strategy, Growth Capital, Lower Middle Market
Everyone prepares you for the financial side of selling. Nobody prepares you for the identity crisis, the grief, the relationship changes, and the disorientation that follows. Here’s what the emotional side actually looks like and how to navigate it.
September 2, 2025
Business Owner, Entrepreneur, Exit Strategy, Selling a Business
The owners who get premium valuations spend 6–18 months preparing before going to market. Here are the five areas — financials, owner dependency, revenue diversification, recurring revenue, and data room readiness — where preparation creates the most value.
August 26, 2025
Business Valuation, EBITDA, Exit Strategy, Selling a Business
Before you engage an M&A advisor or get a valuation, there are questions worth sitting with. Financial readiness, personal clarity, operational gaps, and strategic options — the answers shape every decision that follows.
August 22, 2025
Business Owner, Exit Planning, Exit Strategy, Selling a Business
Recent Posts
- Bowling Green, Kentucky Economic Outlook & Business Opportunities (2025–2026)
- Clarksville, Tennessee Economic Outlook & Business Opportunities (2025–2026)
- Memphis, Tennessee Economic Outlook: Growth Drivers, Business Opportunities, and What Smart Operators Should Know
- Birmingham, Alabama Economic Outlook: Growth Drivers, Business Opportunities, and What Smart Operators Should Know
- Nashville, Tennessee Economic Outlook: Growth Drivers, Business Opportunities, and What Smart Operators Should Know
Recent Comments
Recent Posts
- Bowling Green, Kentucky Economic Outlook & Business Opportunities (2025–2026)
- Clarksville, Tennessee Economic Outlook & Business Opportunities (2025–2026)
- Memphis, Tennessee Economic Outlook: Growth Drivers, Business Opportunities, and What Smart Operators Should Know
- Birmingham, Alabama Economic Outlook: Growth Drivers, Business Opportunities, and What Smart Operators Should Know
- Nashville, Tennessee Economic Outlook: Growth Drivers, Business Opportunities, and What Smart Operators Should Know