We just worked with a client on a profitable yacht brokerage business in FL. Long history, seller of retirement age, great lease, decent staff, more than $10M in listings. BTW listings are the only thing of value in any brokerage. So, all was right with the world.
Local bank liked the financials, contracts with listing owners (used boats only) and the buyer had the collateral. The seller had done a great job wih SEO and was getting solid inbound traffic/leads from the internet.
As is customary in our firm all businesses get looked at by at least two of us. Myself, of course, and one intermediary who has experience in the industry. I sent the package over to Gary and asked him to get back to me with his thoughts (Gary has owned 2 yacht brokerages). He called me within the hour and said the company was worth less than half what the seller wanted! Most of the listings were overpriced and therefore the adjusted value of the commissions was overstated.
On behalf of the client we went back to the seller and diplomatically renegotiated the terms of the sale and everyone won.