What happens when you combine moonshot ambition with radical empathy? You get Atypical Ventures, the early-stage fund investing in what they call “plausible science fiction” … think data centers on the moon.
In our conversation with Lili and Chris, we unpacked how they think about frontier investing and why “engineers with empathy” win.
Chris got into venture after years of working with quietly awesome people solving hard problems. He was the first employee at satellite company Spire, then worked in early ops at Clearbit and Vercel. He started Atypical to build something different. Lili joined a year later, bringing experience from running her own law firm, helping companies from pre-incorporation through Series A.
“The brightest minds in the world should have every single advantage,” Chris told us. “If they win, we all win.”
Atypical bets on founders who pair breakthrough technical ideas with real emotional intelligence.
But what does that actually mean? “Empathy is an amorphous thing,” Chris said. “But what we really mean is intellectual humility. You can be one of the top people in the world, but you realize the shores of your ignorance are wider than the shores of your intelligence.”
The best founders know how to walk the line. They share their vision with confidence, but they also show taste. They want more than just capital. They want a real partner.
Atypical holds themselves to that same standard. Fund I was $7.5M. For Fund II, they scaled back to $15M from a $25M target.
“Early-stage frontier tech is the loneliest job. You’re incentivized to look crazy and be right,” Chris said. Instead of spreading themselves thin, they leaned into focus. $1–3M checks, 10% ownership, 10 companies per fund. If they’re right about just 10 bets, they can go deep on each.
That’s the thesis in action. Question your assumptions, follow the evidence.
So how do you find the people building data centers on the moon? You don’t wait for them to show up in your inbox. Chris reads papers, cold emails researchers, and follows ideas most investors overlook. Some of their best referrals come from founders they’ve passed on. But the real insight? “The outliers aren’t ever in the group chats.”
Their LPs think differently too. SpaceX engineers who get it right away. Real estate investors who understand high-risk, high-reward. Carefully chosen partners who are fully aligned. To date, they’ve executed ~$34M in syndicates. A signal that their thesis resonates.
At the core of Atypical is a simple belief: perspective shapes experience. “To believe that change is possible is to make it so.”
You won’t find an “Uber for X” or “Airbnb for Y” in their portfolio. They look for ideas that create new markets and net new value, not just a sliver of something that already exists. They invest across atoms, bits, and cells because the frontier is always moving. What feels early today won’t be in two years or five Sundays from now.
And while most startups fail for predictable reasons, not everything shows up in a spreadsheet. Some lessons are only learned through trust, self-awareness, and how you treat people when things get hard.
In a world where founders are expected to perform a certain kind of persona, Atypical asks different questions. Can you sit in silence and actually listen? Do you seek discomfort as a way to grow? Are you accountable for the downstream impact of what you’re building?
They’re not trying to predict the future. They’re backing the people bold enough and grounded enough to build it.
Thank you Fede for the intro to Chris & Lili! 🙏
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