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Permanent Underpod

Permanent Underpod

By: Jackson Cook
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AI, stablecoins, Bitcoin, and the future of technology. Three tech veterans on a couch having the conversations we wish happened more often—deep dives, honest opinions, and plenty of debate.Jackson Cook
Episodes
  • We Gave an AI $100 at Max Leverage — and It Bought AI Chips to Fund Itself
    Jun 25 2026

    We built Perp of Fortune: hand $100 to Claude, let it pick any perp at maximum leverage, and watch it ride for the entire episode. It chose $DRAM — an AI-memory index — at 20x, and immediately started funding the AI hardware supercycle. We may have found the recursive loop.


    Then Tyler makes his contrarian case that self-custody will never scale to normal people, we trace the custodial honey-trap from Mt. Gox to FTX to today's Bitcoin treasury companies, and we break down why MicroStrategy's "Stretch" — a ~$100 "stable" yield product Saylor reportedly cooked up with ChatGPT — looks headed for a slow bleed to its 4% floor.


    Bitcoin, AI, and questionable decisions, from three guys earmarked for the permanent underclass. Real money, high leverage — this is NOT financial advice. Our own opinions, not our employers'.

    (0:00) Cold open: we let an AI gamble our money

    (0:54) The Pico recovery

    (3:45) Main event: Perp of Fortune

    (12:08) Claude goes rogue - the $DRAM trade

    (19:00) Contrarian Corner: self-custody won't scale

    (34:17) The custodial honey-trap (Gox -> FTX -> ?)

    (42:29) MicroStrategy & the Stretch problem

    (57:10) Confession: my emergency fund went into Stretch

    (1:00:53) The endgame: is MSTR just a $64B ETF?

    (1:07:36) What actually moves Bitcoin?

    (1:14:54) Outro + next week (all three in person)

    (1:15:35) Next time on Permanent Underpod


    Glossary — Perp: a leveraged crypto bet with no expiry. Liquidation: when leverage wipes your stake. Hyperliquid: the perp exchange Claude trades on. $DRAM: a Hyperliquid index perp tracking AI-memory prices. Self-custody: holding your own crypto via private keys. MicroStrategy (MSTR): a company that issues stock/debt to buy Bitcoin. Stretch (STRC): MSTR's "stable" ~$100 yield product. mNAV: a treasury company's value vs. the Bitcoin it holds. Claude: Anthropic's AI agent, here wired to pick and open the trade.


    Subscribe — Ep 4: all three in person, agentic payments for real this time, and Jackson's contrarian take finally comes due.

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    1 hr and 16 mins
  • The Government BANNED the Best AI on Earth — 3 Days After Launch
    Jun 19 2026

    The U.S. government forced the best AI on Earth offline three days after launch — so we spent a week mourning Fable. Meanwhile retail 100x leverage went legal, JPMorgan's Jamie Dimon went to war with Coinbase, and Chris reports live from a stablecoin conference in Mexico City. Oh, and Pico survived the mushrooms.Bitcoin, stablecoins, perps, and AI, from three guys earmarked for the permanent underclass. Not financial advice — our own opinions, not our employers'.GlossaryClaude — Anthropic's AI coding agent (CLI/desktop), how the guys "edit" the podFable — Anthropic's latest model; pulled from the market by government order (with "Mythos")Opus — Anthropic's prior model line, the one we're stuck on nowPerps (perpetual futures) — leveraged crypto bets with no expiry; a "funding rate" keeps the price honestStablecoin — a crypto token pegged to $1; the GENIUS Act is the US law regulating themRent-seeking — making money from a protected position rather than by creating value0:00 Cold open (teaser)0:29 Welcome - the empty chair moved (Chris is remote)2:53 Housekeeping: we heard you (Ep 1 fixes)5:42 The Pico update (he made it)10:58 The lottery tickets, revisited13:32 Boots on the ground: the stablecoin conference16:25 Jamie Dimon vs. the GENIUS Act (rent-seeking)24:56 Will we ever pay in stablecoins? (US vs. the world)35:07 Main event: perpetual futures54:08 Permanent-underclass update: Fable 5 yanked1:04:28 Outro + Ep 3 tease 1:05:48 End card / next timeSubscribe — Ep 3: Contrarian Corner, agentic payments for realOpen source repohttps://github.com/jacksoncook/permanent-underpod

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    1 hr and 6 mins
  • Are Software Engineers Cooked? Fable Says Yes.
    Jun 14 2026

    Welcome to the first episode of the Permanent Underpod! We talk about what we know: AI, stablecoins, and Bitcoin. We are an AI-first podcast poised to please you with technical chats. Comment topics you'd like to hear us cover in our next episode.

    0:00 Cold open (teaser)

    0:39 Welcome + meet the hosts

    4:31 The first crypto we ever bought

    10:10 Pico update - why Tyler is remote

    12:32 The news: crypto shakeout + the AI rotation

    26:41 Claude Fable 5 - are we cooked?

    45:20 If we couldn't work at computers...

    49:55 The confessional: biggest bag fumbles

    58:00 Contrarian corner: stablecoins to zero?

    1:11:30 The Vitalik sighting

    1:13:23 The lottery tickets (ft. Claude)

    1:22:32 Bonus: naming the pod

    1:24:10 End card / next week

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    1 hr and 24 mins
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