You can learn a lot about a buyer by the questions they ask. The average buyer sends over a due diligence checklist they got from ChatGPT. P&L statements, churn rates, traffic sources. Those things matter but it's table stakes. It tells you nothing about how seriously they're evaluating the business or how well they understand what they'd actually be buying.
The best buyers ask different questions. They ask things that make you pause and force you to look at your own business from an angle you (maybe) hadn't thought about. They're trying to figure out whether this thing still works once they're the ones running it.
I've been on the sell side of enough acquisitions across media properties, SaaS products, marketplaces, and communities to notice patterns. These are 50 questions that stood out. Not because they're the most common, but because they actually mean something.
If you're a buyer, asking the right questions shows you're serious and that you actually understand the business. If you're a seller, having answers to these ready before anyone asks shows you're prepared. And prepared sellers close faster and at better terms.
Revenue quality
What percentage of revenue comes from your top 10 customers? If one account makes up 40% of revenue, you're not really buying a business. You're mostly buying a relationship with that customer.
For credit or token-based purchases, how many of those buyers actually come back and buy again? This is basically your repeat purchase rate for non-subscription revenue.
Published by Arian Adeli