Lost my summer 2023 internship, filthy rich retired mentor has asked to help…

kazeemwahid

He probably could, but is that what you want (having previously secured a tech internship)? Here's what I'd do:

1/ Determine some roles you'd like to explore this summer and why (preferably in areas where you think he has knowledge/network of) - eg. xyz roles in tech firms like [one that fell through] because I'm interested in abc and long term I think it'll set me up for DEF. But I'm also interested in finance roles because xyz...

2/ I'd take an indirect approach to the lunch conversation as your mentor also likely wants to learn about your motivations/goals and provide advice/mentorship, rather than simply be transactional. He knows "how the game is played" (him = successful, mentor at a target, you = aspiring junior, 1st gen diversity). The key is being likeable, which requires building empathy and making "your ask" feel natural. 

The conversation should naturally explore 1/, and if he doesn't bring something up like ("I know a few people in x, let me have a chat with them / forward your resume") then you could ask some open ended questions like:

• Based on my career goals / interests, do you think the types of opportunities I'm exploring make sense? 
• If you were me, what types of opportunities / companies should I be targeting?
• A bit more direct: "Do you know anyone looking for summer interns that might be a good fit for what I'm looking for?" 

Thank you sincerely for the thoughtful response. I'm going to pocket those lines for use on Friday. So honestly, I just fell into the tech "business" internship. The opening was emailed to us by this university group I'm in, it seemed somewhat interesting, a big tech name that would look solid on my resume, solid money, and I wanted to live in California for a summer because I've never really been anywhere. Interview was a breeze. In retrospect, I should have pocketed that offer and explored what else was out there. I read The Journal every day and I have always been intrigued by finance (and the earning potential, obviously), hence I've perused WSO from time to time and came here to post this thread. That said, all of my friends on campus who have their prestigious finance summer associate gigs lined up are a special sort of hyper-driven and obsessive. I'm honestly envious of them and insecure about competing with them (I frankly can't compete with them). And I was too naive to realize how helpful this mentor could have been on that front, especially had I asked him for help last fall or even 9 to 12 months ago during summer 2023 recruiting, right? With the connected tech/finance mentor randomly reaching out and eager to help, it made me wonder if I could put finance back on the table? But I have no idea what is even possible. I am sure he can get me a random "finance" internship, but I'm pretty sure I could land something random myself. At the risk of sounding like a pretentious (and probably delusional) prole, can he get me into a prestigious summer role? What is realistically the best-case? Like is something my GS, MS and JPM bound pals will be like 'w-t-f, how did that happen?' even possible? The fact that it is nearly April is making me assume no, but I'm obviously clueless as to how this world works.

OP, are you male or female biologically, (not the bullshit identify as one).

Male.