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Discussion on: I'm Vivek Saraswat, investor in Dev Tools + Infra startups @ Mayfield and former product leader @ Docker/VMware/AWS. AMA!

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Jacob Herrington (he/him) • Edited

Hey Vivek!

I listened to your interview and really enjoyed it, thanks for sharing.

Two questions:

1) How did you transition from managing tech products to investing? Any key transformative periods or was it a gradual change? Did you receive any traditional education regarding early-stage investing or did you learn as you went? (I'm reading your post from July about a year in VC, but any other thoughts would be awesome!)

2) Favorite edition and/or class in D&D (or your preferred tabletop game if you don't play D&D)?

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Vivek Saraswat Ask Me Anything

Hi Jacob! Thanks for listening to the interview.

1) I was lucky enough to make the transition because the folks at Mayfield gave me an incredible opportunity. My biggest realization as a product manager was that I liked helping other people build things, and venture gave me the chance to do that at scale by working with multiple companies and helping their teams grow. During my time at VMware and Docker I spent time helping VCs with due diligence around the cloud-native ecosystem, and at Stanford I took one class which walked through mechanics of the venture industry (e.g. term sheets, investments, etc.). Most of my education and past experience was focused on operating life however, and much of the venture side was learned on the job.

2) I've been playing D&D since 2nd edition. My favorite version is definitely 5E. I think it strikes the right balance between simplicity, game balance, and freedom of expression. In terms of favorite class, I really like what they've done with the Paladin in 5E. No longer tied purely to Lawful Good, the smiting mechanic is awesome, and the subclasses have a lot of interesting flavor variances (Oath of Ancients being my personal favorite).

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Jacob Herrington (he/him)

Thanks for getting back to me! Seems like you've got a super interesting path.

I've only played 5e, but I love the simplicity and focus on storytelling. May the dice gods favor you. :)

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