Rabbithole with Dave Nadig

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Rabbithole: Where investment nerd Dave Nadig grabs one investing idea in his teeth and will not let it go until all the blood has been drained from the stone. Zero BS. No niceties. Just digging in to learn something from an actual expert in 30 minutes or less. Think of it as hot wings but for your brain. You're welcome.

Episodes

  1. 09/05/2025

    How Bitcoin ETFs Really Work with Teddy Fusaro

    In this episode of Rabbit Hole, Dave Nadig sits down with Teddy Fusaro, President of Bitwise Asset Management, to dive deep into the mechanics and implications of Bitcoin ETFs. They break down how creations and redemptions really work, the SEC’s role in shaping the market, custody and compliance issues, and what the future of tokenization may hold. If you’ve ever wondered how crypto and traditional finance connect at the ETF level, this conversation offers a rare inside look from one of the industry’s leaders. Topics Covered: Evolution of ETFs and lessons for crypto ETFs How Bitcoin ETF creations and redemptions actually work The SEC’s restrictions and why cash creations dominated early on Transition to in-kind creations and their efficiency benefits Concerns around custody, AML/KYC, and “bad” Bitcoin Transparency of the blockchain and proof of reserves Custody risk, Coinbase’s role, and future diversification Common myths: paper Bitcoin, tax advantages, and wash sales Why large holders are moving into ETFs (estate planning, collateral, convenience) How this paves the way for multi-asset crypto ETFs The bold future: tokenized ETFs and on-chain finance Timestamps: 00:00 – Bitcoin ETFs and echoes of past ETF debates 01:19 – Introduction of Teddy Fusaro, President of Bitwise 02:59 – ETFs as “weapons of financial mass destruction” concerns 04:12 – SEC’s stance on in-kind creations and custody rules 07:00 – How cash creations work in practice 10:59 – Benchmark pricing and execution in Bitcoin markets 14:28 – Transition to in-kind creations and cost savings 20:05 – AML/KYC concerns and custody protections 23:11 – Transparency of blockchain and proof of reserves 26:50 – Coinbase custody and single-custodian risk 31:00 – SAB 121 and the rise of traditional custodians in crypto 32:08 – Myths about tax advantages and wash trading 35:12 – Why big Bitcoin holders are moving into ETFs 37:47 – Implications for multi-coin ETFs 39:00 – Future of tokenization and on-chain ETFs 40:33 – Closing thoughts and where to follow Teddy

    41 min

  2. 06/16/2025

    The Hidden Risk Behind ETF Growth | Eric Balchunas and Dave Nadig Debate If We've Gone Too Far

    ETF innovation or madness? In this episode of Rabbithole, Dave Nadig is joined by Bloomberg’s Eric Balchunas for a candid and wide-ranging conversation on the explosion of new ETFs—some useful, some ridiculous, and some outright dangerous. They debate where the line should be drawn between investor freedom and regulatory responsibility, why the current ETF boom feels different, and whether the rise of private markets and derivatives in ETFs is creating cracks in the financial system. From yield-maxing “hot sauce” products to private equity in public wrappers, this is a no-holds-barred look at where the ETF industry is heading. 🔍 Topics Discussed: Why not all ETF buyers are your mom—and why that matters The ETF rating philosophy: truth in labeling over moral judgment ESG ETFs and the dangers of overpromising The rise of “YieldMax” style products and their behavioral appeal Are leveraged and options-based ETFs pushing the ecosystem too far? ETF structure vs. mutual funds during liquidity crises When ETFs outgrow their underlying markets (and what that breaks) The problem with private equity ETFs and mark-to-myth pricing Buffers, derivatives, and the new face of retail-friendly structured products Eric’s crypto ETF thoughts, hopes for a uranium spot ETF, and more

    48 min

  3. 05/17/2025

    The Fourth Turning Is Now | Neil Howe on the Coming Financial Reset and Who Rebuilds What’s Broken

    What does it mean to come of age during chaos—and how does that shape the generations who must lead us through it? In this thought-provoking episode of Rabbit Hole, Dave Nadig speaks with Neil Howe—author of The Fourth Turning Is Here—about the evolving role of Gen X in today's world, the generational dynamics underpinning societal shifts, and what history teaches us about crisis, community, and rebirth. This is not just a theory session—it’s a practical guide to understanding where we are in the cycle and what might come next.Topics Covered: Why generational transitions are slowing—and why that matters The Gen X identity crisis: from latchkey kids to future elders How community rises from conflict during fourth turnings Millennials' collective investing mindset vs. Gen X contrarianism The historical role of financial repression and inflation in crises Parallels between Gen X and the Lost Generation How institutions are built—and who builds them Will the next societal reboot be state-driven or community-driven? Global synchronization of generational crises and what that implies What comes after the fourth turning—and how Gen X fits into it

    53 min

  4. 04/08/2025

    Tax Holy Grail? The Hidden ETF Strategy Nobody Talks About | Brent Sullivan

    For transcripts, commentary and further reading, visit https://www.nadig.com/ Join Dave Nadig as he dives deep into the complex world of ETF tax strategies with expert Brent Sullivan from Tax Alpha Insider. In this illuminating conversation, they break down the often misunderstood concept of "return of capital" distributions in ETFs and how these can impact your investment strategy and tax planning. ## Key Topics Covered: - What return of capital actually means and how it works in different market conditions - The origin of return of capital in Master Limited Partnership (MLP) ETFs - How modern buy-write and covered call strategies utilize return of capital - Tax implications when your cost basis reaches zero - Potential downsides and risks of aggressive return of capital strategies - How ETF sponsors manufacture return of capital through tax-loss harvesting - The difference between capital gains and ordinary income in distribution planning - What investors should track and monitor when investing in these products - How to find reliable information about an ETF's distribution characterization

    29 min

  5. 03/05/2025

    Money Delusions: Barry Ritholtz on the Elusive Definition of Money and How Not to Invest It

    In this initial episode of Rabbithole, Dave Nadig explores the psychology of money and investing with Barry Ritholtz, author of "How Not to Invest." Their conversation challenges conventional financial wisdom and reveals insights about what money is, and how we use and invest it. Key topics include: Why money is a tool for freedom and agency, not a store of value or end goal How childhood experiences shape our lifelong money behaviors and attitudes Why market crashes affect us differently at various life stages The dangers of algorithmic social media and information overload for investors Why avoiding mistakes is more important than chasing extraordinary returns Rethinking Bitcoin and other investments through better framing The wisdom of humility in financial decision-making Barry shares candid personal stories and draws on decades of experience as a trader, strategist, and wealth manager to identify the ideas, numbers, and behaviors that typically destroy wealth. Buy Barry's Book https://amzn.to/3F7APZP

    37 min
  • 5 Episodes

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About

Rabbithole: Where investment nerd Dave Nadig grabs one investing idea in his teeth and will not let it go until all the blood has been drained from the stone. Zero BS. No niceties. Just digging in to learn something from an actual expert in 30 minutes or less. Think of it as hot wings but for your brain. You're welcome.

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