Long Journey Ventures closes $181M fund three, bets on 'magically weird' pre-consensus investments

Summary

Long Journey Ventures has closed its third institutional fund at $181M, a figure the firm's co-founders Lee Jacobs and Cyan chose deliberately — 18 is a numerological reference to "chai," meaning life in Hebrew, and the number reflects their framing of venture capital as gift-giving to entrepreneurs.

The firm launched in 2020 after Jacobs and Cyan, who had worked together at AngelList, decided to partner up. The $181M vehicle is technically their fourth fund overall.

Investment thesis

Long Journey's core mandate is what they call "magically weird" — pre-consensus bets that most investors won't touch. Looking back at their highest-returning companies, the one common thread was that nobody believed in them at the time. The logic is simple: if you enter after something becomes a buzzword, you've already lost the price advantage.

With the AI application layer now crowded, Jacobs says Long Journey is already thinking past it. Portfolio examples of the picks-and-shovels approach include Crusoe and Together AI, as well as a stealth chip company. The firm deliberately avoids the "Cambrian explosion" of high-valuation AI application bets circulating right now.

Adventure partner Justin Marsden exemplifies the firm's earliest-stage conviction — he backed Kettle & Fire in 2015 when bone broth was an unfamiliar concept and has a pattern of finding companies at inception, often before they have a pitch that fits any conventional thesis.

Diamond Foundry and the sci-fi investing framework

Cyan invested in Diamond Foundry when the market assumed it was purely a lab-grown gemstone play. Her actual thesis was industrial and compute-grade diamonds — wafers for semiconductors and industrial cutting applications — not the wedding-ring market other investors kept referencing. That investment was directly shaped by Neal Stephenson's novel The Diamond Age, which describes a post-scarcity future where synthetic diamond manufacturing underpins advanced technology.

Cyan draws heavily on Stephenson's work as an investing framework. Snow Crash anticipated VR and virtual social worlds; The Diamond Age informs her view that in a world of manufactured abundance, human artisanship, original thought, and handmade goods become the scarce and therefore valuable things. She argues AI-generated mass production of art, music, and code will make the authentic human-made artifact more valuable, not less.

Utopia deficit and media

Cyan's sharpest observation outside the fund itself: Hollywood defaults to dystopia because wastelands are cheaper to render than utopias. AI-generated production could change that cost equation and make optimistic science fiction viable to produce. She's alarmed that at a recent talk, only one person in the audience — a 20-year-old — had read The Diamond Age. More science fiction, and specifically more utopian science fiction, is something she sees as genuinely consequential for how the next generation thinks about the future.

Geography

Long Journey has invested globally — Europe, Brazil, and elsewhere — but Jacobs expects the majority of the new fund to deploy into US companies. His reasoning is structural: America's tolerance for failure and its established legal framework for business make it easier to invest with conviction. He sees the current wave of network states and pop-up cities as genuinely interesting but still too frontier to drive significant capital allocation.