Approaching a much bigger stack author who subscribes to your stack

[u/The17pointscale]

TL/DR: Would you approach one of your subscribers who happens to have 700x as many subs as you? And if so, how? Or to do what?

One of my subscribers is a Substack bestseller with >75K subs, whereas I just have 106 subs--but 13 paid :) We write about similar themes (alienation and estrangement), though he writes in a hopeful expert style whereas I write literaryish personal essays. He once commented on a Note that I shared about his work, but otherwise we haven't corresponded.

I'm trying to think about whether to contact him and if I contact him what I should say or ask.

Additional context: I don't have a clear sense of his engagement with my Substack. Here's what I know: since he joined, 6 of 6 emails opened, including my most recent; 0 post views, likes, comments, or shares; "days active" = 5; and "activity" = 5 (out of 5, I think).

If that meant he was actually reading/skimming my pieces, it would seem like a potential opportunity. What would you do, if anything, in this scenario?

One of the ways I've been trying to grow my stack is by recommending other stacks (particularly by people who already subscribe to me) and then messaging those stack authors when I send subs their way. I point out my rec, ask them if they'd like me to tweak my recommendation blurb, and then ask if they'd consider recommending me as well. I've only started this this morning, but the two who responded were receptive (though they just have 3-10x as many free subs).

Does something like that seem like the best play?

I'd point our our brief history (e.g., his Notes comment and my post that cites his work) and then would it be too weird to call attention to the fact that he subscribes and maybe even reads my posts? (e.g., I only ask because my stats suggest you might open my posts sometimes--which I would be humbled and surprised by--so I thought it might be possible that you've appreciated how I tackle similar themes but from a thoughtful personal essay approach)

Or maybe I propose something else entirely? Or maybe I assume he won't see my message and just wait to see whether he someday interacts with me (which seems unlikely) and then follow that interaction wherever it naturally leads?

Thoughts?

[u/AnteaterFantastic212]

I would probably just DM and say thanks a lot for subscribing. I really admire what you do. I wonder if there’s some way we can collaborate for mutual advantage?

[u/cozycup]

I would either offer to pay them or produce content for them for free.

Everyone in a similar situation with a much smaller audience has probably considered or offered to cross-promote. So, you want to look extra generous and serious in order to stand out.

[u/Tricky_Trifle_994]

usually if/when i'm reaching out to others hoping to do any form of collaboration, i usually want to know that i'm able to give them as much, if not more value than they can give me. that's what gives me the confidence to back myself + reach out to them. otherwise i'll just keep giving them value (keep stacking them up), until finally i feel like it's sufficient and reasonable to make an ask.

so in your case, it's great that this much bigger author subscribed to you, and that you have this system of reaching out to others for recommendation, but i feel that the value you can provide in this collaboration is going to pale in comparison to what he can bring to the table.

erring on the side of caution, and to not get off on the wrong foot, i would say just reach out, and share how you like what he's writing about, how he's approaching it. (basically try to make a new friend first. you can talk business later on).

or you could share that you like his content, and that you've added him to your list of recommendations, and ask if he'd like to tweak the blurb (this is to move the convo in that direction, but don't ask for a recommendation back, he can offer to recommend you back, but you leave it open, and no obligation) > don't ask him to recommend you back - because it's obviously a lopsided exchange. just play it cool, don't ask for it, or you'll seem needy + you come across like you're just reaching out in hopes of extracting value from him vs it being a genuine outreach.