Unchained

Dragonfly raises a $650M Fund IV amid crypto's institutional vs retail sentiment gap, the industry exodus including Kyle Samani's departure from Multicoin, OpenClaw's OpenAI acquisition and crypto Twitter harassment, X402 payment standards for AI agents, Polymarket's controversial 5-minute Bitcoin betting markets, and the brewing federal vs state regulation battle over prediction markets.

Welcome to The Chopping Block — where crypto insiders Haseeb Qureshi, Tom Schmidt, Tarun Chitra, and Robert Leshner chop it up about the latest in crypto.

This episode kicks off with major news: Dragonfly just closed their $650 million Fund IV, making them one of the largest crypto VCs not through growth, but because others have downsized. The timing feels surreal — they keep raising right when markets dump, creating the biggest gap between institutional optimism and retail sentiment Haseeb has ever seen.

But money flowing in contrasts sharply with talent flowing out. Kyle Samani left Multicoin, Arianna Simpson departed A16z Crypto, and several other crypto veterans are moving on. The crew unpacks what this "great resignation" means for an industry that feels like it's shifted from pioneer phase to settler phase.

Then they dive into the OpenClaw saga — the viral AI coding assistant that got acquired by OpenAI, but not before its creator almost deleted it due to harassment from crypto Twitter demanding he launch a token. This leads to a deep discussion on X402 payment standards and why AI agents might prefer crypto over credit cards.

Finally, they debate Polymarket's controversial 5-minute Bitcoin betting markets and the brewing legal battle between federal and state regulation of prediction markets. Let's get into it.

Listen to the episode on Apple Podcasts, Spotify, Pods, Fountain, Podcast Addict, Pocket Casts, Amazon Music, or on your favorite podcast platform.
Show highlights
🔹 Dragonfly raises $650M Fund IV while other crypto VCs face "mass extinction" and downsizing
🔹 Kyle Samani's departure from Multicoin signals crypto's shift from pioneer to settler phase
🔹 Industry exodus includes Arianna Simpson, Toshi from Ethereum Foundation, and other veterans
🔹 OpenClaw creator almost deleted viral AI tool due to crypto Twitter harassment over tokens
🔹 X402 payment standard emerges as walletless protocol for AI agent transactions
🔹 OpenAI acquires OpenClaw through separate foundation structure, not direct acquisition
🔹 Polymarket launches controversial 5-minute Bitcoin up/down markets sparking gambling debate
🔹 CFTC chair files amicus briefs defending prediction markets against state regulation attempts
🔹 Federal vs state jurisdiction battle intensifies over event contracts vs sports betting classification
🔹 Institutional sentiment remains bullish while crypto native sentiment hits historic lows

Hosts
⭐️Haseeb Qureshi, Managing Partner at Dragonfly
⭐️Robert Leshner, CEO & Co-founder of Superstate
⭐️Tarun Chitra, Managing Partner at Robot Ventures
⭐️Tom Schmidt, General Partner at Dragonfly

Timestamps
00:00 Intro
01:04 Dragonfly Closes $650M Fund IV
03:26 Institutional vs Retail Sentiment
06:14 Bear Markets as Opportunity
13:48 Kyle Samani’s Exit
21:44 OpenClaw Gets ‘Acquired’ by OpenAI
24:03 Token Pressure & Harassment
25:05 Is OpenClaw Actually Useful?
31:01 Why Open Source Will Move Faster Than Big Labs
33:13 Agents, Memecoins, and the Dark Incentives
37:40 Why Crypto Payments Beat Credit Cards
40:09 Polymarket’s New 5-Minute Markets
49:43 State Gambling Laws vs CFTC Federal Preemption
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The crew tackles everything from the CFTC's controversial stance on prediction markets to the real-world impacts of rising crypto crime.

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The CFTC has announced an innovation council, Chair Mike Selig has asserted that prediction markets are under the agency's ambit, SBF wants another trial and Nancy Guthrie's kidnapping is casting crypto in a negative light.

In this episode of DEX in the City, hosts Jessi Brooks, Katherine Kirkpatrick Bos and TuongVy Le discuss how the distribution of the CFTC's council highlights industry's need for better gender equity, why Selig's stance on prediction markets triggers “a huge constitutional debate,” why SBF's push for a new trial is so dangerous for crypto, and whether the crypto industry can do more to mitigate crime.

Find out why SBF's search for a new trial has far reaching effects beyond his case. Plus, can crypto tackle crime without sacrificing its benefits?

If you want your crypto taxes done carefully — not guessed — Crypto Tax Girl is offering $100 off one-on-one crypto tax services.

Their team focuses solely on crypto and has been helping investors navigate tax season since 2017.

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Hosts:


⁠Jessi Brooks⁠, General Counsel at Ribbit Capital


Katherine Kirkpatrick Bos, General Counsel at StarkWare


⁠TuongVy Le⁠, General Counsel at Veda

Links:


Unchained:


SEC and CFTC Signal United Front on Crypto


Trump Won’t Consider Pardon for SBF: Report


DEX in the City: How Crypto Exchanges May Be Holding Up the Market Structure Bill


This week's good news:

How Ripple is Helping Great Ormond Street Hospital Charity to Unlock Crypto Philanthropy

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Stani Kulechov unpacks Aave Labs’ “Aave Will Win” proposal, explaining why the company wants the DAO to have power over its finances.

Thank you to our sponsors!


Adaptive Security

Aave Labs has proposed a “Aave Will Win” framework that will direct all revenue to the DAO to bring the protocol under “a token-centric model.”

In this episode, Aave founder Stani Kulechov explains why Aave Labs is putting its funding at the mercy of the DAO and how the framework could drive DeFi innovation.

Plus wen Aave v4? And is Aave Labs’ requested budget too much?

Guest:


Stani Kulechov, Founder of Aave Labs




Previous appearances on Unchained:


Why Aave's Founder Is 'More Bullish on Ethereum Than Anything Else’


Why the Founders of Aave and Sky Are Still Bullish on Ethereum DeFi


Satoshi, Shorter Blocks, & Secret Plot - The Chopping Block


Stani Kulechov on Why Aave Is So Successful - Ep.212

Links:


Unchained:


Aave Revenue Overhaul Sparks Governance Clash


Aave Labs Proposes Off-Protocol Revenue Sharing With Token Holders


The Chopping Block: Aave Civil War + Flow Hack + Coinbase Super-App


Aave’s Rushed Governance Vote Draws Backlash


How Aave Labs and the DAO Should Split Ownership of the Brand – Uneasy Money


Uneasy Money: Why Token Holders Have No Rights & Why Every DAO ‘Has Failed’


‘Poison Pill’ Proposal Calls for Aave DAO to Take Over Aave Labs


AAVE Holders Question if DAO Quietly Redirected Revenue Away From Treasury

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The Mag 7 have committed over $700 billion to AI infrastructure, but the companies building the models may never capture the value.

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Adaptive Security


Fuse: The Energy Network

The BLS just quietly revised away 862,000 jobs, and real-time inflation trackers now peg price growth below 1%, less than half of what official figures report. 

If the Fed is steering monetary policy with stale data, investors need to ask what else the models are getting wrong. 

At the same time, the Mag 7 have committed more than $700 billion to AI infrastructure, with Anthropic alone projecting $1 trillion in revenue within five years. Is that conviction or the early stages of a debt cycle nobody is pricing? 

And then there is the institutional side of crypto: BlackRock's BUIDL fund just landed on Uniswap with $2.4 billion in assets, Apollo acquired $90 million in Morpho tokens, and AI agents are already settling micropayments in stablecoins. 

Austin Campbell, Ram Ahluwalia, and Christopher Perkins sit down with Truflation’s CEO Stefan Rust to ask whether the numbers we trust are telling us the truth.

Hosts:


⁠Ram Ahluwalia⁠, CFA, CEO and Founder of Lumida


⁠Austin Campbell⁠, NYU Stern professor and founder and managing partner of Zero Knowledge Consulting


⁠Christopher Perkins⁠, Managing Partner and President of CoinFund

Guest:


Stefan Rust, Founder and CEO of Truflation

Links:


Unchained: 


BlackRock Just Chose Uniswap. The Market Didn’t Care. Here’s Why.


Apollo Moves Into DeFi Lending With Morpho Token Deal


UNI Spikes on BlackRock DeFi Move, Then Gives It All Back

Macro:


NBC: U.S. had almost no job growth in 2025


PBS: Inflation measure falls to nearly five-year low as gas prices fall and housing costs cool


Crowdfund Insider: Secretary Of The Treasury Scott Bessent Calls Out Truflation's Inflation Numbers At Senate Banking Hearing

AI CapEx:


Amazon, Google And Others Are Pouring $700 Billion Into AI CapEx, Top Analyst Explains Why This Makes It 'Hard' To Bet Against Nvidia


CIO: Data center capex to hit $1.7 trillion by 2030 due to AI boom

Reuters: OpenClaw founder Steinberger joins OpenAI, open-source bot becomes foundation

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As miners approach historical stress zones, Bitcoin’s correlation with tech stocks is hitting at the worst possible moment. Enter AI.

Thank you to our sponsor Crypto Tax Girl!

Public mining companies are once again approaching breakeven territory, a zone that in prior cycles preceded forced selling and capitulation. But unlike past downturns, balance sheets today are cleaner, leverage is lower, and many operators are pivoting toward AI data center hosting as a structural offramp.

At the same time, Bitcoin has been trading alongside frontier technology stocks. That correlation is resurfacing at precisely the wrong moment, as growth equities face renewed pressure. If growth portfolios were the marginal buyers during the rally, they may now be the marginal sellers.

In this episode, Steven Ehrlich speaks first with John Todaro about miner economics, hash rate dynamics, and whether another round of selling could emerge if Bitcoin remains near breakeven levels. Then Zach Pandl joins to examine Bitcoin’s correlation with tech stocks, the mechanics behind recent gold volatility, and why the next phase for crypto may be driven by differentiation rather than broad beta.

Hosts:


Steven Ehrlich, Host of Bits + Bips: The Interview

Guests:


Zach Pandl, Head of Research at Grayscale


John Todaro, Managing Director, Crypto & HPC/AI Equity Research at Needham & Company

Links:

Bitcoin Miner Danger Zone


Major Bitcoin Miners Face Shutdown Risk If BTC Falls Below $70,000

Miner Pivot to AI


America’s Biggest Bitcoin Miners Are Pivoting to AI

The Tech Selloff


Wall Street’s Anything-But-Tech Trade Shakes Up US Stock Market

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