The pitch was right up Marc Andreessen’s alley: a fledgling but buzzy digital media startup, which intended not only to produce its own content but to sell its content-management software to other publishers—and, if that worked, to scale its platform to anyone willing to pay. The co-founders? Three men in their 30s, deeply fascinated by technology and the internet, who already had money from Google executive chairman Eric Schmidt and who would take funding from Peter Thiel’s Founders Fund, too.

This was 2012 and the startup attracting Andreessen’s attention was The Atavist, a high-touch web magazine with dreams of becoming a software company as well. The co-founder was Nicholas Thompson, the top editor of NewYorker.com, who was juggling his day job, his startup and his young family. Though Thompson had to drag his toddler to the office one Saturday to pitch Andreessen, the investor was sufficiently impressed to hand over $50,000 to Thompson and his co-founders.

It was a small amount for his venture capital firm, Andreessen Horowitz, but Andreessen’s considerations went beyond a single deal. Now known as a firebrand venture capitalist and vocal scourge of the woke mainstream media, Andreessen took a far different approach to the media back then. In fact, his outreach to The Atavist was a sign that he aimed to play nice with the press, according to a former Andreessen Horowitz executive familiar with the deal. In 2012, his firm was only a few years old, making it advantageous for Andreessen to maintain his chummy relationship with journalists, who would look favorably at his support of a high-minded outlet like The Atavist.