Stewart
Alsop

Santa Fe, New Mexico is not where venture capitalists go to win. It's where they go to retire, or to find themselves, or to make pottery. Stewart Alsop went to Santa Fe, and then he raised a $15 million seed fund from the state government and started backing the next generation of media technology companies. He's been doing this sort of thing for 50 years.

You know him as the guy who backed Twitch when it was still called Justin.tv - a scrappy live-streaming platform that Amazon bought in 2014 for roughly a billion dollars. Or maybe you know him as the Fortune columnist who wrote in 1997 that Apple's acquisition of NeXT was "precisely the wrong thing" and dismissed Steve Jobs's return as "sheer nonsense." That column is still cited as one of Silicon Valley's most spectacular wrong calls. Alsop wrote a follow-up titled "Steve Jobs Keeps Rocking My World." He keeps his errors on the shelf where everyone can see them.

That quality - the willingness to be wrong in public, loudly, with your name on it - is part of what makes him unusual among people who manage other people's money. He doesn't hedge his opinions into oblivion. He wrote in 1991 that "the last mainframe will be unplugged on 15 March 1996." The Computer History Museum dedicated a page to him "eating his words." The mainframes are still running. Alsop thinks this is funny.

What's less funny, and considerably more interesting, is how someone with that track record of public misses has also made some of the most prescient bets in Silicon Valley history. Twitch was a seven-year hold that returned extraordinary multiples. TiVo, backed during his years at New Enterprise Associates, redefined how Americans thought about television before streaming existed. The DEMO Conference he founded in 1991 was where Palm debuted the PalmPilot and VMware first showed the world it could run multiple operating systems on a single machine. Alsop had already moved on by the time those products became cultural milestones, but his instinct for the right stage at the right time was never the question.

The family business was words. His father, Stewart Alsop Jr., co-wrote the thrice-weekly "Matter of Fact" column in the New York Herald Tribune and parachuted into Nazi-occupied France during World War II to support the Resistance. His uncle Joseph Alsop was one of the most influential Cold War columnists in America. The Alsop Papers - plural, covering both brothers - occupy a significant section of the Library of Congress.

Stewart Alsop II graduated from Occidental College with a degree in English in 1975 and discovered that the journalism world was not waiting for him. He enrolled in bartending school. The bars were not hiring either. He tells this story often, with the particular relish of someone who has since been proved correct about enough things to afford the luxury of self-deprecation.

By 1983 he was the third editor of InfoWorld, which put him in Silicon Valley at precisely the right moment - the personal computer revolution was happening in real time, and he had a publication that talked directly to the people building it. He founded P.C. Letter in 1985, a fortnightly newsletter that functioned as the essential intelligence report for executives at major hardware and software companies. It was narrowly targeted, deeply sourced, and expensive in the way that things were expensive before the internet made distribution free. The Agenda Conference and DEMO Conference followed, turning product demonstrations into high-stakes theater.

His column "Alsop On InfoTech" ran in Fortune from 1996 to 2003. Seven years of calling things. Some calls landed. Some didn't. All of them had his name on them.

In 1996, Alsop joined New Enterprise Associates as a Venture Partner - the same year Mike Moritz, another former journalist, made the move to full general partner at Sequoia. The parallel was not lost on the industry. Journalists had always influenced where money went in Silicon Valley; now two of them were managing the money directly.

By 1998 he was a General Partner at NEA. The Twitch investment came later, after he left NEA in 2005 and co-founded Alsop Louie Partners with Gilman Louie in 2006. Louie's background was in national security and defense technology; Alsop's was in media, publishing, and the consumer-facing side of computing. Together they built a firm with roughly $100 million under management, focused on early-stage technology companies willing to take real risks.

Alsop's investment thesis was shaped by three decades of watching technology products succeed and fail. He describes looking for founders who are "pigs" - entrepreneurs willing to die for their vision - who hold "true north" (genuine domain expertise) and "speak in tongues" (use industry-specific language rather than VC jargon). The terminology is blunt by design. So is the man.

He was on the Sonos board from 2006 to 2013. He has been removed from multiple boards for being too direct. He considers this consistent behavior and defends it as ultimately serving the companies better than the alternative. Whether the companies agree is a matter of record.

The name TK MediaTech Ventures is a journalist's joke. TK is editorial shorthand for "to come" - the placeholder you drop in a draft when you don't have a fact yet and need to come back for it. It appears in half-finished copy across every newsroom in America. Alsop and his co-founder Jim Ward chose it deliberately. They are two media guys who moved to New Mexico and eventually realized they were in New Mexico with capital market knowledge and media expertise that nobody else in the state was deploying.

In September 2024, the New Mexico State Investment Council committed $15 million to TK MediaTech Ventures. The fund targets 15 to 20 seed- and early-stage U.S. media technology companies over a seven-year exit timeline. The investment thesis is what Alsop calls the "third convergence" - the intersection of computing, artificial intelligence, and immersive media, which he believes is as significant as the first convergence (computers and telecommunications) and the second (mobile and cloud).

His Substack newsletter, "What Matters (To Me)," has been running since 2020. Recent pieces include "The Slow Death of Social Networks" and an analysis of "Twitter vs DOGE." He describes himself as an "OG pundit and VC investor thinking small and big thoughts." The self-description is accurate and deliberately modest.

He co-hosts a podcast called "Stewart Squared" with his son, Stewart Alsop III - who separately runs the 660-episode "Crazy Wisdom" podcast covering AI, consciousness, and philosophy. Father and son use "Stewart Squared" to explore how computing history predicts the future of artificial intelligence. The family journalism gene runs in both directions.