“The Best Long Con You Ever Pulled”, Yishan Wong, Sam Altman2015-07-11 ()⁠:

[by Yishan Wong] Here’s one.

In 2006, Reddit was sold to Condé Nast. It was soon obvious to many that the sale had been premature, the site was unmanaged and under-resourced under the old-media giant who simply didn’t understand it and could never realize its full potential, so the founders and their allies in Y Combinator (where Reddit had been born) hatched an audacious plan to re-extract Reddit from the clutches of the 100-year-old media conglomerate.

Together with Sam Altman, they recruited a young up-and-coming technology manager with social media credentials. Alexis Ohanian, who was on the interview panel for the new Reddit CEO, would reject all other candidates except this one. The manager was to insist as a condition of taking the job that Condé Nast would have to give up substantial ownership of the company, first to employees by justifying the need for equity to be able to hire top talent, bringing in Silicon Valley insiders to help run the company. After continuing to grow the company, he would then further dilute Condé Nast’s ownership by raising money from a syndicate of Silicon Valley investors led by Sam Altman, now the President of Y Combinator itself, who in the process would take a seat on the board.

Once this was done, he and his team would manufacture a series of otherwise-improbable leadership crises, forcing the new board to scramble to find a new CEO, allowing Altman to use his position on the board to advocate for the re-introduction of the old founders, installing them on the board and as CEO, thus returning the company to their control and relegating Condé Nast to a position as minority shareholder.


JUST KIDDING. There’s no way that could happen.

[Sam Altman’s response:]

Cool story bro.

Except I could never have predicted the part where you resigned on the spot ☺

Other than that, child’s play for me.

Thanks for the help. I mean, thanks for your service as CEO.

[“In October 2014, Reddit raised $66.79$502014 million in a funding round led by Sam Altman and including investors Marc Andreessen, Peter Thiel, Ron Conway, Snoop Dogg, and Jared Leto. In July 2017, Reddit raised $243.55$2002017 million for a $2.19$1.82017 billion valuation, with Advance Publications remaining the majority stakeholder. In February 2019, a $300 million funding round led by Tencent brought the company’s valuation to $3 billion. In August 2021, a $700 million funding round led by Fidelity Investments raised that valuation to over $10 billion. The company then reportedly filed for an IPO in December 2021 with a valuation of $15 billion.” Post-dilution level of ownership by Condé Nast parent: 30%.]

[“What I find interesting is that the two other admins who have responded seem to be agreeing with him. Even if it’s in just a joking sort of manner the fact that they are responding and not denying it in the slightest seems strange.”]