Podcast Summary: The Wolf Of All Streets – "Bitcoin Braces for Powell’s Jackson Hole Speech – $100K Next? | Friday Five"

Date: August 22, 2025
Host: Scott Melker
Guests: NLW (Nathaniel Whittemore), Co-host, Guest Analyst

Overview

In this lively episode of the Friday Five, Scott Melker (with NLW and a co-host) dives into the market tension surrounding Fed Chair Jerome Powell’s much-anticipated Jackson Hole speech. The discussion explores whether Bitcoin’s $112,000 support will hold amidst rate cut speculation, the rapidly evolving regulatory landscape in crypto, MicroStrategy’s recent drama, groundbreaking DOJ comments on code, and China weighing yuan-backed stablecoins. The mood is witty but analytical—a “touch grass” kind of week packed with big news for crypto and macro watchers.

Key Discussion Points

1. Powell’s Last Jackson Hole Speech and Market Jitters

Timestamps 00:01–05:25

• Atmosphere: Jackson Hole seen as the “Super Bowl of financial markets” ([00:08], NLW).
• Powell’s Legacy: This is Powell’s final Jackson Hole as Fed Chair; speculation if he'll make bold statements or “go out with a bang.”
  • “Is he going to, you know, throw a grenade? Explosions in the background as he casually walks away into the sunset like a Hollywood movie.” ([01:52], NLW)
• Rate Cut Uncertainty:
  • Market expectations of a September rate cut have dropped from “100%” last week to under 70% ([03:13]–[03:24], Co-host).
  • The prediction markets echo this decline—down to 60% ([03:30], Co-host).
• Powell’s Style:
  • Both hosts agree Powell will likely “tamp down the assuredness” of a rate cut without any surprise attacks.
• Market Sensitive to Language:
  • The whole event is about “deeply analyzing his tone. If he sneezes in the wrong direction… every single gesture that he makes.” ([00:08], NLW)
  • Compares potential grandiloquence: “He might try to get that JFK or MLK quote in there...” ([04:13], NLW)

2. Crypto Integration & Wyoming Blockchain Symposium

Timestamps 05:25–08:41

• Washington’s Tone: Wyoming Blockchain Symposium shows Washington establishment signaling deeper “integration of crypto and the financial system.” ([06:04], Co-host)
• Fed Officials’ Discussions:
  • “The conversation has shifted ... even the Fed should use crypto rails.” ([06:04], Co-host).
• Policy and Legislation:
  • Senator Lummis (of Wyoming) announces Wyoming’s Frontier Stablecoin project and predicts “market structure [legislation] by 2026” ([06:52], NLW).
  • Skepticism that 2026 feels “bearish” given prior expectations ([06:52], NLW).
  • Senate likely to “lean on the House’s version of the bill” for bipartisan support ([07:36], Co-host).

3. Crypto Legislation & Political Environment

Timestamps 08:41–10:27

• Regulatory Rush: Midterms loom, increasing the urgency for crypto legislation.
• Industry’s Political Push:
  • Winklevoss twins donate $25M to a pro-crypto super PAC ([08:41], NLW)
• Elizabeth Warren Warning:
  • Sen. Warren could chair Senate Finance Committee if Democrats flip Senate—“the queen of the anti-crypto army” ([10:27], NLW).
  • “It could be a very, very bad situation... You can't get complacent.” ([10:27], NLW)

4. MicroStrategy Drama & Market Psychology

Timestamps 10:27–16:37

• MSTR Volatility:
  • MicroStrategy stock drops 21%—outpaces Bitcoin’s price drop ([10:27], NLW).
  • Company loosened stock sale restrictions, causing investor nerves.
• Broader Market Volatility:
  • Risk-off attitude hitting “favorite stocks”—Palantir, AI sector ([11:33], Co-host).
  • “It’s a weird moment... all decisions are being made not based on fundamentals, but on narratives and conversations.” ([14:05], Co-host)
• Yield Opportunities:
  • Discusses MicroStrategy’s variable rate perpetual share, STRC: “trading now at 94.44... supposed to trade on par at 100... 8 or 9% yield” ([15:17], NLW).
  • “Be greedy when others are fearful...” ([16:10], Co-host)
• Memorable Moment:
  • “When the tide goes out, you can see who’s swimming naked, maybe you can just be the one stealing the clothes from those.” ([16:30], NLW)
  • “Yeah, exactly.” ([16:37], Co-host)

5. DOJ: Code Writing & Criminality

Timestamps 16:38–18:50

• Department of Justice Statement:
  • “Writing code without bad intent is not a crime.” ([16:38], NLW)
  • Seen as a major advance for developer rights in crypto.
• Cautious Optimism:
  • Yet, as Co-host observes, “difference between... representatives saying a thing and... it being enshrined in law.” ([17:19], Co-host)
  • “If you are a developer, every sort of statement like that is helpful... but... it’s always going to be some amount of gray area.” ([17:19], Co-host)
  • NLW: “If you’re Roman Storm... your appeal just got more bullish.” ([18:15], NLW)
  • “It’s 100% bullish, it’s just... how positive is its actual impact?” ([18:21], Co-host)

6. China’s Yuan-Backed Stablecoin Proposal

Timestamps 18:50–21:40

• Major Policy Shift:
  • China contemplating yuan-backed stablecoins to advance yuan’s international role ([18:50], NLW; [19:32], Co-host).
  • “China is watching the US Dollar have its... best long-term resurgence potential created because of stable coins.” ([19:32], Co-host)
• Control vs. Adoption:
  • Discussion of how much control China is willing to cede to private sector to expand adoption.
  • “Stablecoins are now a geopolitical force.” ([20:18], Co-host)
• Skepticism:
  • NLW: “It’s not going to work. When has a stablecoin backed by anything other than US dollars gained any traction anywhere?” ([21:03], NLW)
  • “Supply, in this case, I do not think creates demand.” ([21:19], Co-host)
  • Speculates on China’s ability to wield trade leverage for adoption.

Notable Quotes & Memorable Moments

• On Powell’s Style:
  “If he sneezes in the wrong direction, which way he coughs and every single gesture that he makes. It’s Pal Day. Are you celebrating?” ([00:08], NLW)

• On Regulatory Urgency:
  “People need to remember that Elizabeth Warren would become the chair of the Senate Finance Committee… the queen of the anti-crypto army… that could be a very, very bad situation.” ([10:27], NLW)

• On MicroStrategy’s Moves:
  “He changes it, there are going to be market participants who haven’t dug too deeply… feel a bit panicked or… like he’s a bit panicked...” ([13:32], NLW)

• On Market Sentiment:
  “It’s a weird moment... all decisions are being made not based on fundamentals but based on narratives and conversations.” ([14:05], Co-host)

• On DOJ’s Coded Message:
  “Writing code without bad intent is not a crime. This is one of the biggest talking points we’ve had for years...” ([16:38], NLW)

• On China’s Stablecoin Plan:
  “It’s not going to work. I get why they’re doing it... doesn’t mean that anybody’s going to all of a sudden want to use Chinese currency.” ([21:03], NLW)

• On Market Coping Strategies:
  “Be greedy when others are fearful is also, you know, long term historic wisdom… for those with long term conviction, not a lot of better moments than this, I guess.” ([16:10], Co-host)

Timestamps for Key Segments

• 00:01–05:25: Powell/Jackson Hole anticipation, rate cut speculation
• 05:25–08:41: Wyoming Blockchain Symposium, stablecoin state news, legislative landscape
• 08:41–10:27: Political calculus around crypto legislation and midterms
• 10:27–16:37: MicroStrategy stock drop, market volatility, psychological takeaways
• 16:38–18:50: DOJ states code writing not criminal; implications for devs
• 18:50–21:40: China’s potential yuan stablecoin, global currency influence

Episode Tone & Takeaway

Wry, measured, and sometimes self-deprecating, the episode captures a crypto industry caught between major macro uncertainty and real progress in regulation and innovation. Repeatedly, the advice is to “touch grass”—take a pause, stay grounded, and remember that narratives, not just fundamentals, drive market moods. The palpable sense is that both threats (political, regulatory) and opportunities (integration, new products) are accelerating as the industry navigates an exceptionally uncertain and noisy late summer.

Final Take:
“Go touch grass.” – ([22:07], Co-host)
A reminder that amidst volatility, speculation, and endless narratives, sometimes the best move is to step back, breathe, and gain perspective.