Here’s a sentence I never thought I’d say: you can buy a house with your Bitcoin — without ever selling it.

That’s the financial revolution Josip Rupena is building. He’s the founder and CEO of Milo, the fintech startup that’s already issued over $60 million in crypto mortgages — loans backed by your Bitcoin, not your bank account. And here’s the kicker: they’ve never issued a single margin call.

In this episode, we break down how it works, what happens behind the scenes, and why this could be one of the most powerful wealth-generating tools in the Bitcoin ecosystem. We also talk about tokenizing mortgages, using AI to streamline lending, and the potential for a future where your Bitcoin unlocks real-world utility — like homes, yield, and financial freedom.

This is a rare mix of macro insight, startup strategy, and a deep dive into how crypto is transforming the mortgage game.

This episode contains strong language.

Milo Crypto Mortgage – www.milocrypto.com

Custodians: Coinbase & BitGo

Bybit Hack (Largest Hack in History)

Tokenized Mortgages & Yield Products

Real Estate + Bitcoin as a Dual-Asset Lending Model

AI Tools in Underwriting and Client Onboarding

US Housing Inventory Trends (2024–2025)

Email Charlie directly and find episodes and transcripts at CharlieShrem.com

Thank you for listening to The Charlie Shrem Show. For more free content and access to over 400 episodes, visit www.CharlieShrem.com.

My buddy Chris Jenkins just got back from ETHDenver, and he’s buzzing about the convergence of crypto and AI.

He’s the head of operations at the Pocket Network Foundation, and right now, they’re gearing up for their biggest protocol upgrade ever: Shannon. What they’re doing is wild — opening up full permissionless access to decentralized data, from blockchain RPC calls to AI models, Tor nodes, and everything in between.

We talk about agentic systems, LLMs, censorship-resistant data delivery, and why the future of open infrastructure needs crypto tokens to work at all. We also get into what it takes to build B2B tools that feel like B2C, why content creators (like podcasters) should be thinking about data licensing, and why the days of centralized APIs and broken bridges may be numbered.

This one’s nerdy, future-forward, and full of practical examples for how it’s all being built right now.

This episode contains strong language.

Pocket Network Foundation – pokt.network

ETHDenver 2025

Shannon Upgrade (Pocket Network’s protocol upgrade)

fly.pieter.com – Massive AI flight sim built with LLMs

Tornado Cash and Censorship Resistance

Decentralized RPC and Open Data Infrastructure

Drag-and-Drop LLM Interfaces

Email Charlie directly and find more episodes at CharlieShrem.com

Thank you for listening to The Charlie Shrem Show. For more free content and access to over 400 episodes, visit www.CharlieShrem.com.

Pete Rizzo Thinks We're Losing Bitcoin's History. I'm Helping Him Fix That.

Pete Rizzo’s been called Bitcoin’s historian — and after this conversation, you’ll understand why.

He’s spent the past few years diving deep into the stories, people, and drama that built Bitcoin from nothing into a global force. We talk about that work — the threads, the archives, the stories that never made it into the headlines — and how much of our history is already at risk of being forgotten.

This one goes deep: early Mt. Gox days, the Silk Road fallout, Ross Ulbricht, Julian Assange, the Dragon’s Den Slack channel, Bitcoin IRC logs, and even a theory that maybe Satoshi was Julian himself. There’s a lot here — from serious analysis to our own untold stories.

We also get personal: Rizzo opens up about why preserving this history became his mission, and I share how prison, books, and a Muslim roommate changed how I see the world — and Bitcoin.

This episode contains strong language.

Mentioned:

Pete Rizzo’s “Bitcoin Legends” Twitter threads

The Genesis Book by Jonathan Bier

The Satoshi Affair by Andrew O’Hagan

Assange’s RubberHose encryption protocol

Blockworks’ Supply Shock Podcast

Follow Pete:

Twitter/X: @pete_rizzo_

Podcast: Supply Shock

Quotes:

"Bitcoin is the only asset where history actually matters — and yet we’re letting it disappear."

"We treated Ross like a pariah. Now he’s a symbol. That didn’t happen overnight."

"People think Bitcoin started with Satoshi. It didn’t. It started with the people who kept it alive after Satoshi left."

"When I left prison, I was at zero — actually, below zero. But I came out with the most valuable thing: stories."

Thank you for listening to The Charlie Shrem Show. For more free content and access to over 400 episodes, visit www.CharlieShrem.com.