1/ Recently a new founder asked me: “How do I approach anyone to be a mentor to me? It seems like a very overwhelming ask sometimes.” Here’s what worked for me & this was my advice to him that I thought I'd share for others...
2/ I find asking someone to be your mentor is a bit awkward & you won't even know if it'll be a positive relationship yet. You might not like them or their advice may not feel applicable to you. I often found quickly that my personality didn't match theirs at times. Baby steps...
3/ Instead, I'd recommend developing a relationship with someone by seeking some small advice first & continuing to develop that relationship over time by asking more questions. If they feel taxed by you, they won’t respond. Be nice & empathetic. Don't be scared though.
4/ If it turns out the person enjoys spending time with you & you do too, things will naturally progress: (a) they invest & become a defacto mentor, (b) you graciously offer equity to them given all the time they've spent & formalize things, or (c) the relationship just continues
5/ In my case: @mlevchin became my mentor by defacto investing in us. A great distributed systems eng mgr at the co. I interned at became an advisor cuz he helped w/ our early scaling challenges. Some mentor relationships were short but I got great advice. I still thanked them!
6/ How do you approach them? Ask to meet via email/fb msger/linkedin. Tell them it'll be just 30 min. Provide questions in advance. That may be good enough if they just answer your questions async. Do your mtg over the phone at first since in-person mtgs can take a lot of time.
7/ I wouldn't over think this. Just hit people up and see if you vibe together. Have fun!
