Think different | Leading 1st rounds for whacky ideas | General Partner @PortalVentures | @Wharton
New York, NY
Joined August 2021
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I often think about what makes a legendary investor. It is to be daring when nobody else is and to step up when nobody else wants to.
The rational decision framework for an investor is often to wait for signals of de-risking. That could mean seeing companies find a lead, demonstrate significant revenue and growth, or doubling down only when they’ve raised a significant round from other notable investors.
But that’s also when founders no longer need you.
Run toward others’ vulnerable moments — it’s a rule I live by and @PortalVentures invests by. This is why we only come in at the 1st round — and only lead. We believe when nobody else does.
And oh man, it is hard. Decisions are often against the math — and we have to be very, very ballsy. Often, we don’t know if we were early and right or just wrong for months, even years. And every time we stick our necks out for these founders without concrete validation, we are putting our reputation on the line.
But go big or go home, right? Let’s play.
Catrina retweeted
AI predictions for next 6-9 months
-> Anthropic/ OAI fail to ban OSS in the US
-> Anthropic/ OAI continue to innovate product but stall on fundamental tech breakthroughs
-> SOTA Gemini 4 launches at 10x lower cost
-> Elon open sources Grok
-> Anthropic/ OAI ARR growth stalls as enterprises move from tokenmaxxing to rational token consumption/ OSS
-> slow realization in public markets that AI may not replace human labor in next 1-3 years/ has not had a fundamental tech breakthrough in over a year/ lacks ROI/ AI hyper and lab spend not durable
-> moonboy VCs/ hedge funds/ softbank continue to fund Anthropic/ OAI equity raises in private markets as public markets for them are now fully closed
-> CXMT, YMTC announce capacity expansions significantly above market expectations
-> hypers deliver good q326 results on first look but fail to show meaningful AI ROI, guide to "significant capex expansion in fy27"
-> broad realization in public markets the AI dream we got sold on is not anywhere close to realization
-> 10yr hits >5%
-> hyper bonds reprice >10%, CDS hit 3x current levels, and AI credit market dries up as market realizes GPU ABF was not a good idea
-> hyper equities reprice 30-50% lower
-> ORCL falls below $30 as rumors of bailout make the round
-> market realizes memory is cyclical and LTAs won't hold
-> 50% of korean traders get wiped within a week
-> hypers cut fy27 capex
-> semis reprice >80% lower
-> fed cuts >150bps to avoid recession
Against all odds’ encapsulates what @VestExchange is about.
They say you need a massive marketing budget to win the attention economy. Vest did it with no ads, no token incentives, and no shortcuts.
It is incredibly inspiring to witness this journey as an investor: just five years of relentless execution and an unwavering belief that the best product can sell itself.
A belated but massive congratulations to @VestExchange, and shoutout to fellow co-investors @coinbase @SeliniCapital @Auros_global @ambergroup_io @thirdeye_fund @Gold_Mansack and many more!
At most prop firms, ~6% of evaluations ever end in a payout.
At Vest, nearly a third of traders receive a payout. We still have a lot of work to do to make that number higher.
Grateful to @FortuneMagazine for sharing more on the Vest story:
fortune.com/2026/10/07/exclu…
Agreed - human define consciousness & rights based on relationships (dog vs. steak). This just made it 10x more confusing & insidious
