Unpacking Regulatory Challenges and Innovations in Stablecoins

In this episode of Crazy Wisdom, host Stewart Alsop sits down with Juan Samitier, co-founder of DAMM Capital, for a wide-ranging conversation on decentralized insurance, treasury management, and the evolution of finance on-chain. Together they explore the risks of smart contracts and hacks, the role of insurance in enabling institutional capital to enter crypto, and historical parallels from Amsterdam’s spice trade to Argentina’s corralito. The discussion covers stablecoins like DAI, MakerDAO’s USDS, and the collapse of Luna, as well as the dynamics of yield, black swan events, and the intersection of DeFi with AI, prediction markets, and tokenized assets. You can find Juan on Twitter at @JuanSamitier and follow DAMM Capital at @DAMM_Capital.

Check out this GPT we trained on the conversation

Timestamps

00:05 Stewart Alsop introduces Juan Samitier, who shares his background in asset management and DeFi, setting up the conversation on decentralized insurance.
00:10 They discuss Safu, the insurance protocol Juan designed, and why hedging smart contract risk is key for asset managers deploying capital in DeFi.
00:15 The focus shifts to hacks, audits, and why even fully audited code can still fail, bringing up historical parallels to ships, pirates, and early insurance models.
00:20 Black swan events, risk models, and the limits of statistics are explored, along with reflections on Wolfram’s ideas and the Ascent of Money.
00:25 They examine how TradFi is entering crypto, the dominance of centralized stablecoins, and regulatory pushes like the Genius Act.
00:30 DAI’s design, MakerDAO’s USDS, and Luna’s collapse are explained, tying into the Great Depression, Argentina’s corralito, and trust in money.
00:35 Juan recounts his path from high school trading shitcoins to managing Kleros’ treasury, while Stewart shares parallels with dot-com bubbles and Webvan.
00:40 The conversation turns to tokenized assets, lending markets, and why stablecoin payments may be DeFi’s Trojan horse for TradFi adoption.
00:45 They explore interest rates, usury, and Ponzi dynamics, comparing Luna’s 20% yields with unsustainable growth models in tech and crypto.
00:50 Airdrops, VC-funded incentives, and short-term games are contrasted with building long-term financial infrastructure on-chain.
00:55 Stewart brings up crypto as Venice in 1200, leading into reflections on finance as an information system, the rise of AI, and DeFi agents.
01:00 Juan explains tokenized hedge funds, trusted execution environments, and prediction markets, ending with the power of conditional markets and the future of betting on beliefs.

Key Insights

1. One of the biggest risks in decentralized finance isn’t just market volatility but the fragility of smart contracts. Juan Samitier emphasized that even with million-dollar audits, no code can ever be guaranteed safe, which is why hedging against hacks is essential for asset managers who want institutional capital to enter crypto.
2. Insurance has always been about spreading risk, from 17th century spice ships facing pirates to DeFi protocols facing hackers. The same logic applies today: traders and treasuries are willing to sacrifice a small portion of yield to ensure that catastrophic losses won’t wipe out their entire investment.
3. Black swan events expose the limits of financial models, both in traditional finance and crypto. Juan pointed out that while risk models try to account for extreme scenarios, including every possible tail risk makes insurance math break down—a tension that shows why decentralized insurance is still early but necessary.
4. Stablecoins emerged as crypto’s attempt to recreate the dollar, but their design choices determine resilience. MakerDAO’s DAI and USDS use overcollateralization for stability, while Luna’s algorithmic model collapsed under pressure. These experiments mirror historical monetary crises like the Great Depression and Argentina’s corralito, reminding us that trust in money is fragile.
5. Argentina’s history of inflation and government-imposed bank freezes makes its citizens uniquely receptive to crypto. Samitier explained that even people without financial training understand macroeconomic risks because they live with them daily, which helps explain why Argentina has some of the world’s highest adoption of stablecoins and DeFi tools.
6. The path to mainstream DeFi adoption may lie in the intersection of tokenized real-world assets, lending markets, and stablecoin payments. TradFi institutions are already asking how retail users access cheaper loans on-chain, showing that DeFi’s efficiency could become the Trojan horse that pulls traditional finance deeper into crypto rails.
7. Looking forward, the fusion of AI with DeFi may transform finance into an information-driven ecosystem. Trusted execution environments, prediction markets, and conditional markets could allow agents to trade on beliefs and probabilities with transparency, blending deterministic blockchains with probabilistic AI—a glimpse of what financial Venice in the information age might look like.