This episode is a fun one as I had the pleasure to interview Sahil Lavingia, founder of Gumroad, an online platform that allows creators to sell directly to their consumers. The company has facilitated the sale of $356 million in products since its launch in 2011 and now helps over 70,000 creators.

Gumroad raised capital from legendary angels like Ron Conway, Chris Sacca, Naval Ravikant, and from distinguished venture firms such as First Round Capital, Accel Partners, and Kleiner Perkins. After a failed series B in 2015, Sahil was forced to lay off the majority of his staff and pivot his company building strategy to one atypical to the traditional venture model, but in the last year Gumroad doubled its ARR to $10MM.

Drawing on his experiences as an angel investor backing companies such as Hellosign, Figma Design, and Lambda School, Sahil decided to raise his own venture vehicle and using the nascent AngelList Rolling Fund product, quickly secured $1MM/quarter in LP funding. Today’s he’s the most prominent AngelList Rolling Fund Manager with nearly $10MM of annual commitments.

In this episode, Sahil and I discuss the following:

* Sahil’s start at Pinterest and how he applies his founder experiences in investing.

* His learnings from working with VC’s and his thoughts on what he believes makes for a great VC partner.

* Why he decided to go down the investment route, and what was it like raising LP capital through a Rolling Fund.

* Why founders may be more inclined to raise early capital from other founders rather than traditional institutional investors, and how Sequoia has created a savvy model to combat this trend.

* Thoughts on the early stage funding market moving forward.

* How he thinks about portfolio construction as a Rolling Fund investor.

* His hopes for innovation in the venture: Expansion of rolling funds, buyers and sellers being directly connected, and the breaking of the geographical privilege bubble.

Mentioned in this episode:

* Gumroad

* My blog post on rolling funds

I’d love to know what you took away from my conversation with Sahil Lavingia. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.

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