VC Summer Analyst --> Full Time?

So for context, I'm an undergrad currently working with a GP of a VC firm and networked with him over LinkedIn. He has an incredibly impressive resume (think PayPal mafia, 2x HYPSMW, Sand Hill Rd office), and I could grow under his wing and network, but the VC firm itself is still middle-market.

He seems to be really eager for help, and since we agree ideologically on so many things, I've gotten lots of insider project work from him. I don't understand all of it since I'm still a current freshman, and so I'm interning at a more structured, large (>$50B AUM) buy-side role this summer. I believe if I couldn't land a sophomore IB internship, I'd be willing to/want to work with his firm (middle market, $100-$500mm) since I'm not really diversity either. 

To make things short and simple, should I ride on my career being secure as a VC analyst and assistant to a GP right out of undergrad, or should I still try to recruit for sell-side, do my two years of IB, and keep him in my network for future work as his relatively new VC firm grows? I don't want to miss the ship and be slogging away at Goldman if/when his firm takes off, and I legitimately have found the ample amount of work I've done under him super insightful. 

Because we have a unique connection, I think he would love to have me on full-time, especially after I develop more career/technical skills this summer.

Should I ultimately then focus on buy-side research for him and gain his favor, hoping to be one of their only full-time analysts, or should I recruit traditionally like everyone else at my school? Again, sorry for the long, drawn-out question.

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As a college freshmen, you are at a great place with an internship lined up and growing/developing deep relationships. 

You have the right idea of maintaining and continually developing relationship with the investor you are more deeply connected with. Even if you end up pursuing an opportunity outside of his network or geography, do everything you can keep the the relationship warm considering how you two are hitting it off (for example but not limited to catching up in person once a year, seek his advice regularly, refer him any founders/deals you stumble across)

Career wise, i would encourage you to keep your options open by pursuing additional interns across different areas (whether VC, startup roles at different scales, PE/Growth Equity, Big Tech). Depending on your schedule during the semester and if you do have ample time on hand, possibly you can volunteer to do research work for the investor's fund while you can pursue a sell side role in the summer. Doing so will give you the exposure to realize your unique strengths and opportunities for those roles. You have plenty of time and take every available opportunity to identify where you want to thrive.

Good luck and go kill it!

 

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