7/2/2026 at 4:48:05 PM
This was an excellently written, salient post with some good tidbits.I've learned some of these lessons the hard way. I'll add a few. Proof of work is important, but it's not about the magnitude of energy you spend. I went through two iterations of reaching out to my college network. The first time I put so much time into handwriting notes and trying to provide my relatable background. 100 notes, not a single response.
The second time I sent emails that were a few sentences. I had a much clearer ask and devoted the effort into fitting my questions into the email. I wanted a conversation really, but I also tried to communicate what I planned to ask.
15% response rate and invaluable conversations. Less overall "work".
Secondly, and relatedly, don't ever waste someone's time. Don't ask for / accept a meeting if you don't have some semblance of a clear ask. It's hard, especially in early stage business where you're trying to discover what you don't know. But you can try to lay out your tier 1 "here's what I think", "here are the follow ups".
I sensed once that I had irritated someone by lacking the agenda. Another time I took a mutual connection up on an intro where I didn't know what I really needed. I regret both of these.
Thirdly try to pay it forward. It won't always come back around, but you can feel more comfortable asking for help and more cognizant of what a helper (so to speak) is thinking
by jackconsidine
7/2/2026 at 7:43:17 PM
When I was younger, I was always paranoid when I reached out to somebody and didn't hear back. Now that I'm older and busier, I totally get it. Clearly state who you are, what you want, and what your timeline is. It's far easier to reply to a message like that, than to parse paragraphs of fluffery looking for an ask.by andyfilms1
7/2/2026 at 5:38:34 PM
> I went through two iterations of reaching out to my college network. The first time I put so much time into handwriting notes and trying to provide my relatable background. 100 notes, not a single response.This is a thoughtful gesture, but there are at least two problems with it
First, a handwritten note isn't easy to respond to. With an e-mail, you can leave the message in your inbox until you have time to respond and then it's one click to start responding. With a hand-written letter the recipient would have to context-switch from reading mail to using a digital device and they'd have to transcribe your e-mail address. It's not much work, but it's still work that someone has to make time for.
Second, it's an unusual thing to do. It's important to communicate with people through normal, comfortable communication channels where the etiquette is known. Having someone handwrite a letter and look up your mailing address is unusual. Unusual behavior triggers people's suspicions. You weren't trying to scam anyone, but you should be aware that one of the tricks used in scams is to invest unusual amounts of attention and energy into someone. It can trigger a suspicion that you're really after something else.
Your second round of sending short e-mails had neither of these problems. Easy to reply to, nothing unusual about it. It's the way to go.
by Aurornis
7/2/2026 at 6:27:11 PM
> I sensed once that I had irritated someoneSolid advice, (but to others reading) don’t optimize for not irritating people.
Especially your professional network. You built those relationships because you wanted to use them in the future, and the future is now… so, tap them! If they don’t like that, no big deal, no sweat, move on.
If you’re irritating multiple people constantly, then yea you’re probably doing something wrong. But if it’s one person once in a blue moon, that happens, don’t over optimize for avoiding that. You can’t make everyone happy
by cj
7/2/2026 at 5:27:40 PM
+1 that there are few things more exhausting than listening to someone's "proof of work"i'd rephrase as "visible lack of effort is problematic" - anything above that passes the bar for me, and other factors become critical
by bbminner