Unchained, Ep. 908: Bits + Bips: How Wall Street Could Make a Killing off the Next Crypto Winter

Date: September 23, 2025
Host: Laura Shin (with regular "Bits and Bips" panel: Steve Ehrlich, Ram Alawalia, Austin Campbell, and guest Vinny Lingam)
Theme: Examining the intersection of crypto markets, macro shifts, and the emerging world of Digital Asset Trusts (DATs)—especially how Wall Street may profit in the next crypto contraction.

Episode Overview

This episode gathers crypto industry veterans and analysts to dissect macroeconomic signals, the transformation of reporting standards, the burgeoning Digital Asset Trust (DAT) sector, arbitrage opportunities, liquidation risks, and the looming specter of another major crypto downturn. With Wall Street circling DATs for profit opportunities, the conversation pivots between market fundamentals, structural concerns in new crypto investment vehicles, and wider macro dangers.

Key Topics & Insights

1. Macro Backdrop, Rate Cuts, & Market Sentiment

• [06:51] Discussion begins with the fallout from the Fed’s recent 25bps rate cut and its lukewarm market response.
• Ram Alawalia: “There’s been a spike in liquidations, including Ethereum… We haven’t seen this level… in quite a long time. Liquidations are usually viable.” (08:07)
• Market is in a weak seasonal window post-options expiry, with absence of buybacks or earnings catalysts.
• Ram: “The best economist in the world is called Mr. Markets—the S&P 500—and it’s the companies within and how they report.” (10:39)

2. Transparency & Corporate Reporting Evolution

• Quarterly vs. Semiannual Reporting Debate:
  [11:07 – 14:34]
  • Steve Ehrlich raises the pros and cons: transparency vs. operational burden.
  • Austin Campbell:

    “If…ConAgra…or Archer Daniels Midland went from quarterly to semiannually, does it really damage…the information granularity? Probably not really. On the other hand, should banks be moving from quarterly to semiannually? Perhaps not.” (12:48)

  • Potential for real-time, blockchain-enabled corporate data-streaming is discussed, with both promise and practical/data quality challenges.

3. Tokenized Stocks, Insider Trading & Globalization Risks

• [14:34 – 21:47]
  • Vinny Lingam:

    “Once you start tokenizing stocks, trade them globally…you can’t really have enforcement actions against people in foreign countries for insider trading.” (15:20)

  • Austin Campbell: Skeptical of truly “permissionless” tokenized stock trading: “There is a reason stocks are not permissionless. They come with control rights.” (19:47)
  • Discussion highlights difficulties in balancing transparency, privacy, and regulation.

4. Market Outlook: Defensive Sentiment, Gold, & Crypto

• [22:27 – 26:51]
  • Vinny Lingam expresses bearishness: “I’ve got a bunch of put positions… I don’t think [the Fed] should have cut… I think we’re going to see a lot of liquidity unwind.” (22:27)
  • Gold as a Defensive Asset:
    “Gold is, I’d say, a primary position for me right now just because I think it’s all about protecting purchasing power.” (24:53)
  • Macro Risks: Massive US deficits, and skepticism about productivity (AI) as a panacea.
  • Notable Quote:

    “Tell me how we get out of this mess… I’m not buying the tariffs story.”
    – Vinny Lingam (25:03)

  • Ram Alawalia: “Buying gold is what you’re really doing is just front running China, because China has shifted from buying U.S. treasuries to buying gold. They are the bid.” (25:51)

5. Digital Asset Trusts (DATs): Boom, Arbitrage, and Unwinding Risks

• [28:58 – 54:22]
  • Austin Campbell:

    “The eternal problem of the DAT is that they don’t have an internal price stabilization mechanism like the ETFs have…” (30:05)

  • DAT Arbitrage & M&A: Hedge funds are likely to profit by acquiring DATs trading at a discount to their net asset value (NAV), then harvesting the gap.
  • Vinny Lingam:

    “It’s going to happen in a downturn. The M NAV multiple is going to compress… you’re going to have one, maybe two big plays in each space.” (31:37)

  • DAT Survival:
    Austin predicts only DATs with genuine operating models or cash flows—or those exploiting regulatory/tax arbitrage—will survive.
  • DAT Bubble Narrative:

    “Welcome to crypto. That’s what it is… you don’t need that many DATs. A lot of this is liquidity seeking.”
    – Ram Alawalia (33:49)

  • Potential for Nuclear Winter:

    “…the next crypto winter will be a nuclear winter, because what will happen is these DATs will trade at discounts. Hedge funds come in… will buy up the company, short before, then dump it…”
    – Vinny Lingam (38:29)

  • Wall Street Arbitrage Play:

    “Wall Street is going to make so much money on the way down.”
    – Vinny Lingam (41:53)

  • DATs as Minsky Machines:
    Austin: “For anybody who’s in the asset part that’s trading at a premium, you’re in the final phase of Minsky already. And we all know how [that ends].” (48:00)

6. ETFs, Regulation, & the Future of Crypto Investment Vehicles

• SEC’s Accelerated ETF Listings:

  “With ETF listing standards we’re going to have staking inside of the ETFs now… for DATs that are not going to be buying real, cash-flowing businesses, what the hell is it doing existing?”
  – Austin Campbell (52:21)

  • Only DATs that “buy operating companies” (as in, those adding value beyond just holding tokens) are likely to survive.
  • Ram Alawalia: “Stick to quality.” (54:20)

Memorable Quotes & Timestamps

• Vinny Lingam: “The next crypto winter will be a nuclear winter… DATs will trade at discounts.” (00:00, 38:29)
• Austin Campbell: “If you listen to most people trying to explain why their DAT should trade at an M nav premium, it’s a version of the joke: part one, a miracle happens, part two…” (46:58)
• Ram Alawalia: “Wall street says, when the ducks are quacking, feed the ducks…when you see a proliferation of new issuance, that is a contra signal.” (34:17)
• Steve Ehrlich: “I’m just waiting for somebody to put…an ongoing quarterly report on a blockchain where it runs autonomously…” (14:07)
• Austin Campbell: “There are a handful of DATs with operating cash flow—okay, maybe you’re going to work. But for anybody in the asset part trading at a premium, you’re in the final phase of Minsky already…” (48:00)
• Vinny Lingam: “If someone can explain to me how this magically comes together and we don’t have a sovereign debt crisis in the next couple of years…” (59:41)

Contrarian & Closing Thoughts

[54:42 – end]

• Ram Alawalia: S&P’s total return “crushes” gold, and bets on Norwegian Cruise Lines and the aging US demographic.
• Austin Campbell: Predicts the next economic breakdown in the US will look more like Japan’s “aging population” problem, not a traditional crash. Services for the elderly will outperform; beware intergenerational “warfare.”
• Vinny Lingam: As wealth increases, focus shifts from making money to protecting purchasing power. Current state and government deficits make gold and defensive positions attractive, as AI productivity may not save the system:

  “As much as we can over index in productivity, I think for some people…protecting purchasing power is the most important.” (59:47)

• Macro-Finance Debate:

  “None of this matters when Elon's automated robots kill us all anyway.”
  – Austin Campbell (60:37)

Notable Segments & Timestamps

• Vinny’s background & Civic ICO history: (02:15 – 06:51)
• Macro market state, liquidations, and seasonal rundown: (08:07 – 11:07)
• Quarterly vs. Semiannual reporting debate: (11:07 – 14:34)
• Tokenized stocks, KYC, and insider trading risks: (14:34 – 21:47)
• Gold, treasuries, and US macro risk discussion: (22:27 – 27:13)
• Digital Asset Trusts (DATs), arbitrage, and market structure: (28:58 – 54:22)
• Final contrarian and closing thoughts: (54:42 – end)

Tone & Style

The episode is energetic, skeptical, and deeply technical, favoring hard-won wisdom over hype. Panelists spar on details but share a wariness of crypto’s new Wall Street vehicles. The tone slants toward macro caution with darkly humorous asides (e.g., “nuclear winter,” “Elon’s robots will kill us all”), all underpinned by industry experience and an eye for the next structural shakeout.

In Summary

The panel scrutinizes the risks in the current crypto market structure, warning of how Wall Street may profit by arbitraging, acquiring, and liquidating DATs during the next downturn. Despite hopes for regulatory and technological advancement (ETFs, tokenization), the experts remain wary—favoring defensive assets and stressing the importance of true operational quality in crypto companies. The episode is a cautionary tale for anyone eyeing quick profits in the wild new world of institutional crypto vehicles.