Y Combinator's First Batch (YC SO5)

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Y Combinator (YC), the most prestigious startup accelerator in the world, has funded 4,000+ companies, including Airbnb, Stripe, Dropbox, DoorDash, Coinbase, and Reddit. The combined valuation of YC’s portfolio is over $600 billion.

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Paul Graham, Jessica Livingston, Robert Morris, and Trevor Blackwell founded YC on March 11, 2005. Frustrated by the pace of VC investing, the original YC thesis was that investors should be making more, smaller investments, funding hackers instead of suits, and they should be willing to make bets on younger founders.

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The founders of the eight companies in the first batch, YC S05, turned out to be “surprisingly good.” Their fingerprints are all over the startup ecosystem. So let’s see what they’re up to now.

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1. Reddit

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Founders: Alexis Ohanian, Steve Huffman, Aaron Swartz

Company Status: Active

Company Tagline: The front page of the Internet.

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Alexis Ohanian is the most prominent founder of the most successful company in YC’s original batch, Reddit. Reddit, the social news platform and one of the most visited US websites, was last valued at $10 billion. Since founding Reddit, Alexis started two venture capital firms, Initialized Capital and Seven Seven Six.

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Steve Huffman left Reddit in 2009 to start another company, Hipmunk, which YC funded as part of their YC S10 batch, before returning to Reddit as their CEO in 2015. Hipmunk was a travel planning company that shut down in 2020 after being acquired by SAP Concur in 2016.

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Aaron Swartz left the company in 2007 after Reddit sold for $10 million to Condé Nast Publications shortly after its founding. Swartz led a life of activism before he was arrested on January 6, 2011, by MIT police for breaking-and-entering charges after connecting a computer to the MIT network to download academic journals. He was later charged with two counts of wire fraud and eleven Computer Fraud and Abuse Act violations. Before he served his time, Swartz was found dead in his apartment at the age of 26. The medical examiner ruled it a suicide.

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2. Kiko 

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Founders: Justin Kan, Emmett Shear

Company Status: Acquired

Company Tagline: We’re the best online calendar solution ever to exist. Period.

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Justin Kan founded Kiko, the online calendar solution, with Emmett Shear. Kiko grew to 90,000, with its initial distribution coming from a TechCrunch Article. Google launched Google Calendar, and Kiko didn’t believe they could compete with the product. They ended up auctioning off Kiko on eBay. Tucows, a software company, bought Kiko with a winning bid of $265,000, beating out thirteen other bidders. Justin went on to found Twitch, an interactive live-streaming service. YC funded Twitch as part of their YC W07 batch. Amazon acquired Twitch for nearly $1 billion in 2014. Since his Twitch exit, Justin founded Atrium, Fractal, and Rye. Atrium ended up failing after raising a significant amount of venture capital, and Fractal and Rye are still early-stage venture-backed companies. In addition to founding more companies, Justin founded a venture capital firm Goat Capital to supplement his angel investments, including OpenSea, Mercury, and Scale AI. He’s one of the top 100 angel investors (2023).

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Emmett Shear, the other founder of Kiko, joined Justin as CTO at co-founder of Twitch. In 2011, Shear became CEO of Twitch until stepping down earlier this year in March 2023.

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Following the removal of Sam Altman as CEO of OpenAI on Nov. 17, 2023, the OpenAI board selected Shear to be his successor as the Interim CEO.

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3. ClickFacts 

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Founders: Mikhail Ledvich, Mikhail Gurevich, Greg Gurevich

Company Status: Acquired

Company Tagline: SaaS tools for online advertising networks and publishers to stop offensive content, annoying ads, and malware.

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Mikhail Ledvich founded ClickFacts with Mikhail Gurevich and Greg Gurevich. ClickFacts’ YC Company Page lists the company’s status as Acquired, but I could not find any public reports of the company being acquired. It looks like the company stopped operating in July 2007, as that’s the date when two of the co-founders moved on to the next step in their careers. Ledvich was the Product Architect for ClickFacts and worked at several e-commerce companies afterward. Most notably, he was VP of Marketing at Moonsoon Commerce and then Shippo before landing his current role as SVP, Senior Digital Manager at Bank of America.

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Mikhail Gurevich, the CIO of ClickFacts, co-founded another company called ZepFrog and AltLending. Unfortunately, neither company was that successful. Instead, Mikhail Gurevich became a Managing Partner at Dominion Capital, a family office, and RD Advisors, a financing solution for real estate projects.

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Greg Gurevich transitioned into the finance world after ClickFacts, where he was an Analyst at BlackRock, Trader at RBC Capital Markets, and eventually started his own quantitative Hedge Fund called Maritime Capital Partners.

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4. TextPayMe

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Founders: Philip Yuen

Company Status: Acquired

Company Tagline: An SMS payment service that lets you send money to other people using cell phone text messaging.

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Amazon acquired TextPayMe in 2006 and became the foundation for what is known as Amazon Payments. As part of the acquisition, Philip Yuen, the Founder of TextPayMe, worked at Amazon to oversee the product from 2006-2010 before leaving for Zynga to become their Director of Products. Years later, Philip founded Aurabeat Technologies, which went through YC’s W21 batch. Aurabeat Technologies creates air filter technology to eliminate COVID-19 and sells it to hospitals and quarantine facilities.  

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5. Loopt

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Founders: Sam Altman, Nick Sivo

Company Status: Acquired

Company Tagline: A mobile social-mapping service that allows individuals to use their location to discover the real world around them.

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Sam Altman co-founded Loopt with Nick Sivo. Loopt was acquired for $43.4 million in cash by Green Dot in March 2012. While Justin Kan and Alexis Ohanian started billion-dollar companies, Sam may have the best tech career when all is said and done. Sam became a Partner at YC before eventually stepping into the President role in 2014. In 2020, Sam Altman left to focus full-time as CEO and Co-founder of OpenAI. OpenAI was last valued between $27-$29 billion in April 2023 and is the fastest-growing consumer app ever, surpassing 100 million users in less than two months.

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Nick Sivo, a co-founder of Loopt but also the longtime boyfriend of Sam Altman. The two dated for nine years before they broke up shortly after Loopt sold in 2012. Like Sam, Nick worked at YC after Loopt was acquired. He was an engineer and contributed to Hacker News and other YC products. Nick keeps a pretty low profile, and there isn’t much information about him online.

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6. Infogami

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Founders: Aaron Swartz, Simon Carstensen

Company Status: Inactive

Company Tagline: A business intelligence solution.

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We discussed Aaron Swartz earlier in this post since he became a founder of Reddit after co-founding Infogami with Simon Carstensen.

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Simon Carstensen co-founded another startup called Jottit with Swartz after Infogami ceased operations in 2005. Jottit was a startup that made it simple to create a website. Unfortunately, that startup failed after a year, and Simon became a web developer at several companies, including GoMore, Peytz & Co, Watchdog.net, Wemind A/S, and G13. He worked as a freelancer for many years and recently took a job as a full-stack engineer at TRAEDE.

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7. Memamp

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Founders: Zak Stone, Chris Slowe

Company Status: Inactive

Company Tagline: A better desktop search solution.

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Zak Stone co-founded Memamp with Chris Slowe. Zak ended up becoming a career big-tech employee where he went on to work as a Machine Learning Strategist at Apple and is now a Product Manager for Google TPUs on the Google Brain Team. Zak has been at Google for the last seven years.

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Chris Slowe joined the founders of other companies in his YC batch to help them build their companies. Chris joined Reddit as a Senior programmer before becoming the Lead Architect and Manager. In 2010, Chris left Reddit to work with Steve Huffman on Hipmunk as the company’s second engineering hire and Chief Scientist. After five years at Hipmunk, Chris rejoined Reddit as its Director of Engineering before being promoted to CTO in May 2017. Chris is still the CTO at Reddit and has been there for eight years during his recent stint.

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8. Simmery

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Founders: Jesse Tov

Company Status: Inactive

Company Tagline: Social websites.

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Jesse Tov founded Simmery, but the company failed five months after it was founded. Jesse went on to have a successful career in academia, where he lectured at Harvard and Northwestern. He left academia in 2021 and has worked at a stealth finance company in New York since February 2022.