The answer is (probably) in the metrics: -Check the LTV for members, is it going up or down? -What is the number of rebuys a typical customer usually makes? -Wh

The answer is (probably) in the metrics: -Check the LTV for members, is it going up or down? -What is the number of rebuys a typical customer usually makes? -What is the usual cost to acquire a new customer, can that be improved upon? More ephemeral: - Identify if the business has "wide moats" [1] - Can a google algorithm update wipeout your traffic? Is organic google traffic even your biggest traffic source (OP, said "word of mouth" not sure if he meant literally or organic SE traffic) - Are there any competitors? - OP said the site depends on some scraping, any worry that the scrapee may cut off your access? etc, etc, etc Lots of stuff springs to mind without knowing the actual site being sold. [1] http://www.investopedia.com/terms/w/wide-economic-moat.asp#axzz28GgXxlLL http://www.investopedia.com/terms/w/wide-economic-moat.asp#a...