50 questions to ask before you buy a business
The average buyer sends over a due diligence checklist they got from ChatGPT. Don't do that.
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.
Was there a single month that skewed the annual numbers? What happened?
How long does your average customer stick around and what keeps them there?
Have any customers pre-paid annually? When do those renewals come up?
What’s the refund rate and has it changed in the last six months? Rising refunds usually show up before churn kills you.
How much of last month’s revenue came from marketing spend versus organic?
Is there seasonality in the business and what does it look like? This isn’t a red flag. An exam prep app will obviously spike around academic cycles. What matters is whether the seller understands the pattern and uses the off-season productively. Things like shipping features during quiet months, building partnerships, or planning campaigns for the next cycle. Seasonality with a strategy behind it is fine. Seasonality that catches the seller off guard is not.
Audience and engagement
What’s the open rate trend over the last twelve months? Not the average. The trend.
What’s the comment rate, and what’s the reply rate to those comments? This separates actual engagement from passive consumption. High views with no replies usually means people are scrolling, not reading.
How many subscribers have been on the list for more than a year and still open regularly?
Have you ever missed a publishing cadence? What happened to traffic and engagement when you did? If nobody notices when you skip a week, that’s a problem.
Has any single piece of content or event driven a disproportionate chunk of subscriber growth?
If you removed social media distribution entirely, what would traffic look like? A Substack newsletter has way higher platform dependency than one on Beehiiv or Ghost, and that distinction matters for what you’re actually acquiring.
