Unchained

Shehan Chandrasekera, CPA and Head of Tax Strategy at CoinTracker, delves into the complexities of crypto tax reporting, emphasizing the significance of tax-loss harvesting and the implications of the new 1099-DA form. Sebastien Derivaux, Co-founder of Steakhouse Financial, highlights the risks of high-yield chasing in DeFi, the future of stablecoins beyond the US dollar, and the importance of institutional-grade risk curation. Together, they discuss crucial tax strategies and emerging trends shaping the crypto landscape.

Markus Thielen, CEO of 10x Research and expert in crypto trading strategies, dives into the evolving world of prediction markets. He outlines why these markets are still in their early stages and discusses the migration of crypto traders toward them. Markus shares insights on Polymarket and Kalshi, highlighting their strengths and weaknesses. He also reveals ten unique trading strategies that allow for successful predictions without previous biases and emphasizes the importance of the collective wisdom from market participants.

Tensions rise as Jupiter faces accusations from Kamino over misleading contagion risks in their DeFi products. The hosts debate the implications of Hyperliquid's algorithm and its controversial liquidations. Lighter's zero-fee model comes under scrutiny, with comparisons to Robinhood's approach to retail trading. Meanwhile, Farcaster's shift to a wallet-first strategy opens discussions on the future of Web3 social media. The podcast navigates through complex market dynamics, lending strategies, and the evolving landscape of decentralized finance.

Citadel's controversial letter calls for the SEC to regulate DeFi protocols, igniting debates about traditional finance's view on crypto. Hosts explore how AI agents can exploit smart contracts for just $1, raising security concerns. They discuss the implications of a crypto bubble and the need for better communication with traditional finance. Plus, there's a call to support the Samourai Wallet developers amid legal challenges. The episode wraps up with a heartwarming story of crypto donations aiding Hong Kong fire victims.

The hosts dive into the controversial claim that Web3 is dead, driven by spam and weak network effects. They explore whether prediction markets could serve as the true social backbone of crypto. The debate heats up over Layer 1 valuations, weighing their early promise against potential overpricing. Insights into crypto burnout emerge, spotlighting Ken Chan's candid reflections on wasted years. The discussion wraps up with a deep dive into October's cascading liquidations and the flaws they exposed in current systems.

Ryan Rasmussen, Head of Research at Bitwise, and David Nage, Portfolio Manager at Arca, share their insights on the crypto market's surprising downturn in 2025 and their optimistic outlook for 2026. They discuss the implications of Vanguard's major crypto pivot and explore whether Bitcoin's classic four-year cycle is coming to an end due to institutional adoption. The duo also delves into the transformative potential of tokenization and the role of stablecoins in the financial ecosystem, likening stablecoin evolution to the early days of email.

Hosts dive into the intriguing dynamics between traditional finance and crypto. They debate the future of interest rates and dissect the unexpected rise in oil demand. The conversation steers toward the implications of BlackRock's staked ETH ETF and the emergence of decentralized staking rates. Ripple's strategic funding round raises eyebrows, while Citadel's push for DeFi regulation sparks industry discussions. The frantic quest for crypto partnerships among major players reveals a rapidly evolving financial landscape.

Owen Lau, Head of FinTech Research at Clear Street, explores the intricate relationship between crypto equities and Bitcoin and discusses the significance of stablecoin revenue. David Schamis and Bob Diamond from Atlas Merchant Capital delve into the innovative Hyperliquid Strategies DAT, detailing its token economics and performance during market volatility. They also share insights on the regulatory landscape and the potential for growth in digital assets, emphasizing the importance of strategic investments in infrastructure and market structure.

In a riveting discussion, Mark Palmer, a Senior Equity Research Analyst at The Benchmark Company, and Vinny Lingham, co-founder of Praxos Capital, tackle MicroStrategy's recent struggles. Palmer advocates for the company's potential despite cash and dilution concerns, while Lingham critiques its preferred stock model, calling it 'vampiric' to common shareholders. They debate the impact of MSCI risk and the role of regulatory clarity in shaping the future of Bitcoin holdings, providing insights on the crypto landscape and investment strategies.

The hosts dive into Ethereum's Fusaka upgrade and its impact on transaction dynamics. The controversy surrounding Infinex's token sale reveals community backlash and innovative ICO mechanics. They analyze Hyperliquid's perpetual contracts for tokenized equities and the looming regulatory risks. Tensions in Solana’s DeFi with Kamino and Jupiter spark debates on user choice and market fairness. Finally, discussions on AI's role in security and the implications of recent exploits shine a light on the ever-evolving landscape of crypto.