Hey fam,
CK and I recently sat down with Fiskantes to talk about AI and crypto.
Fisky needs no introduction. Sigil Fund’s CIO does not come from a gilded Wall Street apprenticeship. He discovered markets in a high-school stock-picking contest, then paid the rent playing online poker before turning a $150K post-2018 crash bankroll into a $250M+ hedge fund.
It’s proof that streaks of luck compound when you keep taking calculated swings.
Here’s what we learned from him:
1. Look for the bottleneck, buy the monopoly
Fiskantes’ AI equity playbook is painfully simple: track where the constraint is, then back whoever’s easing it.
Three years ago, that was raw compute, so he loaded up on NVDA and chip enablers like TSMC and ASML. When geopolitical risk made data sovereignty a priority, he added Palantir, a company with no real peer in analytics platforms.
2. How He Uses AI in Investing
Humans lost the millisecond trading game long ago. The edge now lies in stretching the time horizon.
Fiskantes uses Karpathy’s analogy of AI as an Iron Man suit: it serves to amplify human judgment, not replace it. The models do the grunt work; but humans still have to make the high-stakes calls on narrative and sizing.
If you feed the AI models average questions, you get average outputs. The edge flows to those who can frame sharper, first-principles questions. That’s the true skill.
3. Why future AIs will bank on-chain
Spinning up a thousand Ethereum wallets for AI agents takes seconds. On the other hand, opening a thousand bank accounts would bury them in KYC paperwork.
Crypto rails are cheaper, faster, and permissionless, which makes them the obvious payment layer for the agentic internet.
4. Ignore the noise
Fiskantes estimates that 90% of “AI + token” pitches are hot air: vague “agent frameworks” and token schemes that add no real value.
He sees a common pattern driven by adverse selection: the best AI founders will go and raise equity rounds because they’re building real products. Others go into web3, slap on a token, and hope crypto VCs will fund anything they can flip.
It’s a noisy space.
Our full conversation packs even more: why stablecoins could become AI’s cash drawer, how to size positions when volatility feels personal, and the one habit that rescues him from ChatGPT rabbit holes.
→ Listen on Apple Podcasts, Spotify, or watch it on YouTube.
02:02 Fisky's Journey into Investing
06:46 Investing in AI and Key Stocks
12:31 The Evolution of AI Usage
20:49 AI's Impact on Investing and Future Trends
25:22 Bullish on New Tech and Crypto
29:40 Crypto vs. Stocks: The Investment Landscape
36:42 Evaluating AI-Crypto Projects
41:44 Contrarian Views on AI and Crypto
47:32 Final Words of Wisdom for New Investors
Remember to subscribe so you never miss a new episode when it drops. We’ll be interviewing more smart guests in the coming weeks, so stay tuned!
Cheers,
Teng Yan
