Unchained Podcast Summary

Episode: The Chopping Block: Dragonfly's $650M Fund + Crypto's Great Resignation + OpenClaw vs Crypto Twitter
Host: Laura Shin
Panelists: Haseeb (Dragonfly), Tom, Robert (Superstate), Tarun (Gauntlet)
Date: February 19, 2026

Overview

This episode of Unchained’s “The Chopping Block” delivers a deep insider view of the recent shifts and dramas in the crypto and web3 industries. Key discussions cover Dragonfly’s successful $650M fundraise in an industry downturn, the “Great Resignation” of prominent crypto leaders, the OpenClaw phenomena and its fraught intersection with crypto, and the ethics and practicalities of ultra-short-term prediction markets. The conversation weaves together humor, market realism, and genuine reflection on the state and future of crypto and adjacent tech fields.

Key Discussion Points & Insights

1. Dragonfly’s $650 Million Fund: Success Amid Market Doldrums

Segment: [00:51]–[06:05]

• Announcement: Haseeb shares Dragonfly’s closure of a $650M fund, noting how challenging fundraising has become as most other VC funds shrink or close.
  • "It's the same size as our previous fund. We're now...one of the largest VCs in the space. Not because we have grown...but because a lot of other VCs have downsized." [01:20]
• Market Context: Dragonfly’s consistency in fundraising during downturns compared to other VCs' “mass extinction.”
• Institutional Participation: The vast majority of capital comes from large institutions, who remain bullish despite retail and native crypto pessimism.
  • "Institutions are bullish. Crypto. They believe all that shit...and they're continuing to invest into the space through institutions like us." [03:38]
• Fashion Moment: Lighthearted jab at the team photo, as co-founder Bo stuns in a purple velvet suit among "Silicon Valley schlubs." [02:36]

2. The “Great Resignation” in Crypto

Segment: [03:13]–[18:47]

• Prominent Departures: Leaders such as Kyle Samani (Multicoin), Ariana Simpson (a16z), Tamash (Ethereum Foundation), Akshay (Solana Foundation), and Nader (EigenLayer) are moving on—often beyond crypto (e.g., AI, longevity).
  • "It feels like we're having this moment of reshuffling, a lot of senior people from the industry suddenly moving on." [05:06]
• Industry Realignment: Panelists reflect that many early crypto pioneers leave as the space matures from “wild pioneer” culture to institutional “settler” mode.
  • "We've exited the pioneer phase and we're now in the settler phase. And the people who settle the towns...are a very different kind of psychology." – Haseeb [13:36]
• Bear Market Opportunities: Bear markets are seen as the best time for founders and VCs to make strategic moves, away from the chaos and FOMO of bull markets.
  • "When there's less competition for deals, you can take longer...You can actually think more than in a bull market when it's an outright mania." – Robert [09:06]
• Emotional Reflection: Haseeb is deeply affected by Kyle Samani’s departure, linking it to a generational shift in the industry.
  • "Seeing Kyle leave honestly hit me harder than anybody else leaving." [18:47]

3. OpenClaw: Viral Open Source, AI Agents, and Crypto Twitter’s Meme Wars

Segment: [21:30]–[34:03]

• OpenClaw Origin & Acquisition: Explains how the open-source AI agent project (once Claudebot) became a phenomenon, recently acquired by OpenAI (with a somewhat ambiguous foundation structure). [22:09]
• Crypto Invasion & Harassment: Founder Peter Steinberger describes being nearly driven to delete the project by aggressive crypto coin shillers and harassment.
  • "‘Crypto people are not just good at harassment, they're also really good at using scripts and tools… I was that close to just deleting it.’" [24:45]
• Why It Resonates: Despite technical limitations, the vibe and TikTok-ready demos spark imagination about the future of agentic automation and permissionless AI.
  • "It's one of these things where you can see the sci-fi movie just poking through the membrane...people love it so much because they want it to get there." – Haseeb [26:57]
• Crypto/AI Overlap: Discussion about how both sectors share technologies, investors, and personnel, making for frequent “collisions” and cross-pollination.
  • "For two industries you would not think have any similarities, there's actually a lot of overlap in terms of the people and the technologies." – Tom [25:07]
• Vulnerabilities & Open Source Edge: Open source allows faster improvement but also introduces major security/prompt-injection risks—something the big labs will tiptoe around.

4. X402 Standard: Agent-to-Agent Crypto Payments

Segment: [34:36]–[37:40]

• What is X402?: A simple protocol designed by/for AI agents to pay each other without the complex wallet apparatus typical in crypto. Recently attracted adoption by companies like Coinbase and Stripe.
  • "The main point is it's so simple that you don't need to know anything about crypto to use it. Which is...why it might be more popular for web2 devs." – Robert [36:49]
• Why Crypto for Agents?: Unlike credit cards (merchant required) or bank rails, crypto is natively accessible to autonomous agents with no country or compliance barriers.
  • "Crypto was kind of made for machines more than it was made for humans." – Haseeb [37:40]
• Outlook: Small at present but expected to grow as more agentic workflows and economic value cross over between AI and on-chain infrastructure.

5. Polymarket & Short-Term Prediction Markets: Gambling, Incentives, and Utility

Segment: [40:32]–[49:44]

• Super Bowl and New Offerings:
  • Huge spikes in volume for Polymarket and CallSheet during the Super Bowl.
  • Polymarket introduces 5-min and 1-min “up/down” Bitcoin prediction markets—sparking panel debate over whether these are innovative or just turbocharged gambling.
• Panel’s Positions:
  • Robert: Sees ultra-short prediction markets as a more risk-controlled alternative to highly leveraged perps; but admits they’re essentially gambling. [41:12]
  • Tarun: Expresses ambivalence—these markets subsidize more informationally valuable markets but are inherently zero-sum and addictive for most.
    • "You have to have these apps that make a lot of money...that subsidize the platform for the ones that are information containing." [45:24]
  • Haseeb: Argues that these “casino” products are crucial for the business model, allowing less liquid, more informative markets to exist.
    • "The five minute markets are subsidizing all of the positive externality markets." [42:59]
  • Tom: Points to the normalcy of similar products in TradFi (e.g., binary options, zero-day options), challenging critics’ selectivity.
• Social Utility vs. Business Reality: References to Vitalik Buterin’s call for markets to maximize social value, but consensus is that businesses need gambling-like activity for broader positive externalities.
  • "Vitalik's proposal...is basically saying, don't build a business." – Haseeb [48:32]

6. Legal Gray Zones: Gambling, Prediction Markets & Regulatory Fights

Segment: [49:44]–[54:06]

• State vs Federal Control: The US is a patchwork—the states control most gambling, but federal preemption can take over if Congress or agencies step in.
• Current Battle: CFTC Chair Michael Selig supports prediction markets’ right to operate federally, clashing with state efforts to shut them down.
  • "This fight about is it gambling, is it sports betting...or are they going to have to stay in their lane and only offer these kind of informational contracts? We'll see." – Haseeb [54:06]
• Comparisons with Other Jurisdictions: The panel marvels at how boundary lines are arbitrary, with the US’s “states’ rights” system being unique and confusing even for professionals.

Memorable Quotes & Moments

• On The Industry’s Mood:
  "Are we the Japanese on the island, kind of fighting when the war is over?" – Haseeb [05:06]

• On Crypto’s Institutionalization:
  "The people who build the social networks are very seldom the people who steward them going forward. It's not Reid Hoffman. Mark Zuckerberg is maybe the only exception." – Haseeb [13:36]

• On OpenClaw Harassment:
  "They crypto people are not just good at harassment, they're also really good at using scripts and tools. I underestimated those people. Honestly, I was that close to just deleting, deleting it." – Peter Steinberger (quoted by Haseeb) [24:45]

• On Short-Term Gambling Products:
  "I just don't think that a five minute market on the price of Bitcoin serves any predictive capability...it's just gambling. Is it healthy? No. Is it sustainable? Probably not." – Tarun [41:23]

• On the Cyclicality of Crypto:
  "Every cycle there's a new VC firm that pops up and becomes meteoric in their rise." – Haseeb [20:57]

Timestamps for Notable Segments

• Dragonfly’s Fundraise & VC Landscape: [00:51]–[06:05]
• Crypto Great Resignation & Industry Shift: [03:13]–[18:47]
• OpenClaw, Crypto, and AI Intersection: [21:30]–[34:03]
• X402 and Agent Payments: [34:36]–[37:40]
• Polymarket’s Prediction Markets – Debate: [40:32]–[49:44]
• Legal Battles over Gambling/Prediction Markets: [49:44]–[54:06]

Conclusion

The episode paints a dynamic portrait of crypto in early 2026: established institutions double down even as grassroots and pioneer figures depart, and the lines between crypto, AI, and social experiments grow blurrier. The panel provides rare candor about the morale, mechanics, and incentives in web3—highlighting both the hope and tension as the ecosystem professionalizes, diversifies, and continually redefines itself.

For further detail, listen to the full episode or follow the panelists on Twitter for their ongoing takes.