About Sahil Lavingia: “Sahil is the founder and CEO of Gumroad. He is the founder of solo GP fund on Angel list rolling fund.

Gumroad exists to help every creative earn a living selling the stuff they make directly to their audience. Previously, he was early at Pinterest — a service that lets users collect, organize, and share the things they are into — and worked on turntable's mobile apps.

He designs and builds products for fun and profit."

Below are the She-VC topics we discussed:

1. You have been employee #2 at Pinterest, founder of Gumroad, followed the drop out kid path of Zuckerberg, Gates, Jobs. Now one of the most talked about rolling fund VC. Where do you find yourself on your expectations?

2. You have raised $10M from Kleiner Perkins, Lowercase Capital, First round, Chris Sacca, Naval, Max Levechin. Why did you decide to be on the other side of the table and write checks for founders?

3. What is a barrier to entry for starting a traditional fund for someone like you who knows everyone at Sandhill road, because VC is a relationship based industry?

4. So what is a rolling fund? What is the future of rolling fund and emerging fund managers? Is there an option for liquidity for LPs in rolling funds?

5. How do you think the SEC rules play in effect in rolling fund considering many of you are vocal about raising money from LPs?

6. In a rolling fund, LPs commit for the first few quarters, how do you think you will manage your follow on strategy if you have one?

7. What message do you want to give to Institutional LPs who think it is highly risky to invest in first time fund managers? Do you think later on you will move to a traditional fund?

8. Let's talk about your thought process on startup performance data and how important it is for VCs to track that and how they can track that at an early stage.

9. How important is it to design a path to monetization in product architecture ?

10. I think venture capital is not a job but it is a lifestyle. So how are you preparing yourself for such a lifestyle. How do you analyze various thinking models? What are the LP resources that you read and follow. How do you maintain work life balance?

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