Alan Schaaf

In 2009, while an undergraduate at Ohio University, Schaaf launched the image-sharing site Imgur, and he earned a BS in computer science in 2010. Imgur was bootstrapped and profitable for five years, scaling to millions of users.⁠[1]

On April 3, 2014, San Francisco–based Imgur announced $40 million in investment from Andreessen HorowitzAndreessen HorowitzAndreessen Horowitz (a16z) is a venture capital firm founded in 2009 by Marc Andreessen and Ben Horowitz. It invests from the seed stage through the growth stage and provides operational support to its portfolio companies.Open the full entry, with a smaller, undisclosed investment from RedditRedditReddit is an online platform that organizes content and discussion around interest-based communities, founded by Steve Huffman and Alexis Ohanian in 2005. Users take part in communities by posting, commenting, and voting; its operating company, Reddit, Inc., listed on the New York Stock Exchange in 2024.Open the full entry; Lars Dalgaard of Andreessen Horowitz joined Imgur’s board. Imgur then had more than 130 million unique monthly visitors and a 13-person team, and planned to use the funds for product development, ad quality, and hiring.⁠[2]

Schaaf said that “over the course of the five years, we probably met with a dozen VCs and angel investors…but we never really clicked.” He added, “Our goal is to become a big, independent business,” and said the company was not pursuing an acquisition by YahooYahooYahoo is an internet brand founded by Jerry Yang and David Filo in 1994, with email, search, news, finance, sports, and advertising businesses. It developed from a web directory into a portal, underwent major acquisitions and security incidents, and sold its operating business in 2017, when the original listed company became Altaba. Apollo-managed funds acquired the brand’s operating business in 2021. Yahoo launched the AI answer service Scout in 2026.Open the full entry.⁠[2]

On November 10, 2017, Andreessen Horowitz (a16z) released the episode “a16z Podcast: How Founders Hire a VP of Product,” based on an event hosted by Caroline Horn of a16z’s executive talent team and moderated by a16z general partner Martin CasadoMartin CasadoMartin Casado is a computer scientist, entrepreneur and venture capitalist who is a general partner at Andreessen Horowitz, where he leads infrastructure investing. A major proponent of software-defined networking, he co-founded Nicira and served as its chief technology officer, and after VMware acquired the company he ran its networking and security business; he also co-founded the nonprofit MuralNet.Open the full entry. Schaaf appeared as founder and CEO of Imgur alongside Vijay Balasubramaniyan, founder and CEO of Pindrop; Shishir Mehrotra, founder and CEO of Coda; and Gokul RajaramGokul RajaramGokul Rajaram is a Silicon Valley product leader and investor who helped build Google AdSense early in his career, went on to serve as an executive at Facebook, Square (Block), and DoorDash, and sits on the boards of public companies including Coinbase and Pinterest; in 2024 he co-founded the investment firm Marathon Management Partners with a partner.Open the full entry of Square.⁠[3]

The episode discussed what the VP of Product role really is, how founders can hire for it and integrate it into the company, and how to avoid common pitfalls when handing over their “baby” to someone else. It was uploaded to the a16z YouTubeYouTubeYouTube is Google’s video-sharing and creator platform, founded in 2005 by Steve Chen, Chad Hurley, and Jawed Karim and acquired by Google in 2006. Built around video uploading, viewing, and creator earnings, the platform has developed Shorts, YouTube Music, Premium, YouTube TV, and products for children, and is headquartered in San Bruno, California, United States.Open the full entry channel on January 1, 2019.⁠[3][4]

Schaaf has more than a decade of experience as a professional coder, advocates for a free and open internet, and has spoken at events including TechCrunch DisruptTechCrunch DisruptTechCrunch Disrupt is a technology and startup conference organized by TechCrunch, combining interviews, product demonstrations, startup competitions and industry networking for founders and investors.Open the full entry, Collision, Web Summit, TEDxWellington, AWS re:Invent, and the a16z Summit. At the time of the 2014 funding, he said: “We want to conquer the internet in terms of self-expression and viral images.”⁠[1][2]