Couple things. (1) Someone else, possibly an estate representative, controls the company. The company may have to go through probate. Perhaps not. Seems like you know some details. (2) Don’t contact until after funeral has occurred. And you are trying to determine who controls the company now, preferably a non-family member (3) Consider snail mail, don’t be aggressive, be ultra non-aggressive. (4) follow up often, but passively (no calls). You may not know who is making decisions, how they are feeling, etc. If you know of intermediaries (accountants, attorney’s, etc) you may try through them. Ultimately, you may need to wait up to a year for probate to complete before a sale could occur. Move on and keep sourcing. Keep tabs gently on this one. Your time likely better spent on other deals. If this one comes to you, then so be it.

Agree with Donald

Adding:
-If you were in touch previously with owner, that is a good thing to mention when reaching out (e.g. you are continuing owner's vision of selling, not a vulture swooping in)
-Some additional research of what is going on is helpful (I was looking at an asset where the owner passed while looking to sell, and the wife stepped in and is likely to run the business for a period of time). BUT it could have been the opposite... the wife might have hated the business, not want/know how to run it, and want to sell faster
-Hopefully it is not going through probate as that may take a long time, and is likely going to create public records and notices that the competitors are more likely to pick up on and take advantage of

simply acknowledging that this is an awkward conversation and that you weren't sure on how to go about it would work the best.

"I know there's probably no right time to do this, and I was so worried that I was being insensitive, however, I've always really liked what you all do and I'd be very interested in talking about buying it when the time is right for you all."

Tyler, Unfortunately I came across this more than a few times during my search, with a slight caveat. Which is I did not know the owner had passed as I was reaching out. In one situation the wife responded to a letter (paper) I had sent, she worked in the business as well but did not want to continue in it. In another instance a letter I had sent to the CEO eventually ended up in the chairman of the board's hands and he reached out. Both were actively looking to sell. I share those to affirm what Donald said above about snail mail. You may consider investigating further to see if there is someone else at the business (ie on the board if there is one) you could address it to. Finally, in both instances that I described they were looking to sell and so receiving the letter was something that they looked favorably upon -- despite it being during less than ideal circumstances.

Thank you all for your great advice. I really like the idea of snail mail with a nicely hand written letter. I do not believe they are going through probate, but how would I know if they were? Also if the company has no website and very little info online how would I go about figuring out who controls the company now if I have never spoke with them and not close enough to know anyone who has.

I agree with these comments. In my industry I quite frequently come across owners that have recently passed away when calling to follow up on my "snail mail" letter. I will tell the receptionist, I am very sorry to hear that, are you still family owned? They will tell me. I think the positive note is that by reaching out you may be helping an owner/spouse/child who possibly does not want to run the business. If a small business is run by a couple then a lot of times one of them is the stronger driving force than the other.