The Charlie Shrem Show Podcast

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.

📚 Mentioned:

Milo Crypto Mortgage – www.milo.io

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)

✉️ Feedback or guest ideas?

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.

📚 Mentioned:

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

✉️ Thoughts? Guest suggestions?

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.

Welcome back, everyone! I sat down with my new friend Daniel Wedman, the head of special situations at Sopris Capital. We delved into a variety of topics, focusing on the dynamic world of Bitcoin and crypto investments, and the evolving landscape of capital markets.

Daniel's Career Journey

Daniel shared his fascinating career trajectory, starting from his early days at Citigroup on a special situations team, to his roles at SL Green and Wheelock Street Capital. His journey into the crypto world began as a side hobby of mining Bitcoin, which eventually led him to join Galaxy Digital's Bitcoin mining team.

Sopris Capital and Investment Strategies

At Sopris Capital, Daniel initially joined to build out the real estate arm but soon found himself pitching innovative investment ideas to Andy Paul, the open-minded founder. One notable strategy involved an ASIC arbitrage, where they imported ASICs from Asia, mined Bitcoin while waiting for them to sell, and then sold them at a premium.

Bitcoin ATMs

We discussed the lucrative business of Bitcoin ATMs, which Daniel stumbled upon through a meetup in New York. Sopris Capital started with 50 machines in Canada and expanded to 200 in the U.S., with plans for further growth. Daniel highlighted the strong cash-on-cash returns and the significant market potential, especially among the underbanked.

Stranded Energy and Bitcoin Mining

Daniel explained the concept of stranded energy and how Bitcoin mining can utilize cheap, otherwise wasted energy sources. He shared an example of a curtailed wind energy project in West Texas, where they built a data center to mine Bitcoin using cheap wind energy.

Economic Shifts and Investment Opportunities

We touched on the broader economic shifts and how they create opportunities for agile and flexible investors. Daniel emphasized the importance of reading the tea leaves and understanding the second and third-order consequences of policies aimed at helping working-class Americans.

Compliance and Industry Maturation

The conversation also covered the increasing compliance requirements in the Bitcoin ATM industry and how this is leading to consolidation, with smaller players being acquired or going dark. Daniel sees this as a positive development, signaling the maturation of the industry.

Future of Energy and Compute

Daniel shared insights from his time at Galaxy Digital, emphasizing the critical role of energy in the future of digital networks and compute. He expressed optimism about breakthroughs in energy technology, which could unlock a new era of innovation.

Closing Thoughts

It was a pleasure having Daniel Wedman on the show. His deep knowledge and innovative approach to crypto investments provided valuable insights for our listeners. As always, major changes in the world present opportunities for those who are prepared to adapt and innovate.

Thank you for tuning in to The Charlie Shrem Show. Stay tuned for more deep dives with influential leaders in the Bitcoin and crypto space.

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

In this episode, I sit down with Joe Flanagan, the Co-Founder and Executive Chairman of Maple Finance, a leading institutional lending platform in DeFi. With nearly $6 billion in loans issued, Maple is one of the few crypto companies bridging the gap between traditional finance (TradFi) and decentralized finance (DeFi).

We cover some of the biggest trends in crypto right now:

• The real value of tokenized assets and why tokenization alone isn’t enough
• How Maple built a transparent, institutional-grade lending market on-chain
• Why crypto’s next big users won’t come from TradFi—but from meme coin traders evolving into DeFi investors
• How regulations are shifting in 2025 and what it means for institutional adoption
• Why DeFi UX is still broken—and how cross-chain strategies can fix it

If you're interested in real-world adoption, institutional DeFi, and where crypto finance is actually headed, this is an episode packed with insights from one of the builders making it happen.

Key Takeaways:

✅ Tokenization alone isn’t the game-changer—what matters is the new financial products that emerge from it.
✅ Institutional-grade DeFi lending is here, but it’s still mostly crypto-native capital participating.
✅ The next wave of DeFi adoption might come from meme coin traders learning how to deploy capital more effectively.
✅ With regulatory uncertainty easing, crypto builders finally have the freedom to innovate at full speed.
✅ Cross-chain user experience is still fragmented, but new infrastructure is emerging to unify ecosystems.

Listen & Subscribe:

🎧 Available on Spotify, Apple Podcasts, YouTube, and wherever you get your podcasts!

Follow Us:

📢 Follow me on Twitter (@CharlieShrem) for more insights, behind-the-scenes content, and updates!

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