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.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)

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.

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 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.

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.

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.

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.

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.

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.

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.

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.

✅ 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.

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

📢 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.

In this episode, I sit down with Hart Lambur, the co-founder of Risk Labs, the team behind UMA and Across Protocol, two projects solving some of the biggest challenges in crypto—cross-chain interoperability and on-chain data verification.

Ethereum has scaled, but in the process, it’s fragmented into over 50 Layer 2s, creating a messy user experience. Hart and his team are pushing for a cross-chain intent standard (ERC-7683) to make blockchain transactions feel instant and seamless—because let’s be real, waiting minutes (or days) to move assets across chains is a joke.

We also dive deep into:

• The “two-second rule” for crypto UX and why speed is king
• How ERC-7683 enables cross-chain swaps without waiting for block confirmations
• Why Ethereum’s fragmentation problem could kill adoption if we don’t fix it
• The future of prediction markets and decentralized oracles
• How Chainlink maintained dominance in the Oracle space—and whether that’s changing
• Why AI-powered agents will need blockchain-based dispute resolution

If you're into DeFi, cross-chain tech, and the future of Ethereum, this episode is packed with insights you won’t want to miss.

✅ Ethereum has scaled, but it now feels like 50 separate chains—interoperability must be solved.
✅ The two-second UX rule: If a transaction takes longer, users will lose focus and abandon it.
✅ ERC-7683 introduces cross-chain intents, allowing instant swaps by having solvers front transactions.
✅ Optimistic oracles (used by UMA) enable decentralized dispute resolution, powering prediction markets like PolyMarket.
✅ AI agents will need on-chain contract enforcement—blockchain oracles will play a crucial role.

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

📢 Follow me on Twitter (@CharlieShrem) for behind-the-scenes insights 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.

In this episode, I sit down with Eran Barak, the CEO of Midnight, a groundbreaking new privacy-focused blockchain incubated by IOHK (Input Output, the team behind Cardano). Eran has an incredible background—before diving into Web3, he built the financial world’s digital plumbing at Symphony, a secure communications platform used by thousands of banks and institutions. Now, he’s bringing privacy and selective disclosure to blockchain, solving one of the biggest hurdles in getting businesses to adopt the technology.

We dive deep into:

• Why privacy isn’t just a buzzword, but a necessity for blockchain to go mainstream
• The problem with public blockchains and how metadata leaks can be dangerous
• How Midnight is using zero-knowledge proofs (ZKPs) to protect data while keeping it usable
• The rise of AI and why your private data is the next target for machine learning models
• Why traditional finance players are still struggling to adopt Web3—and what needs to change

If you’re interested in the intersection of AI, privacy, and blockchain, this is an episode that will blow your mind and show you where the industry is really headed.

✅ Blockchain can’t go mainstream without solving privacy, but regulators still resist full anonymity.
✅ The Midnight blockchain introduces a dual-token system to balance compliance and privacy.
✅ Zero-knowledge proofs allow selective disclosure, meaning your data remains private while still proving facts about it.
✅ AI is the next frontier—your personal data is already public, but blockchain can help protect what’s left.
✅ Traditional finance still relies on outdated infrastructure, but Web3 can offer a better, more secure alternative.

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

📢 Follow me on Twitter (@CharlieShrem) for behind-the-scenes insights 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.

In this episode, I sit down with my longtime friend Arthur Breitman, the co-founder of Tezos, one of the OG blockchains that has been innovating since 2018. We dive deep into the evolution of tokenization, why the first wave fell short, and how the next iteration can unlock real value. Arthur also shares insights on Tezos’ latest upgrades, the growing demand for privacy in crypto, and an unexpected but fascinating use case—tokenizing uranium.

We also explore:

• Why stablecoins became the most successful “real-world asset” in crypto
• The role of privacy in blockchain and the regulatory challenges ahead
• How Tezos continues to innovate with faster block times and seamless upgrades
• The surprising connection between commodities like uranium and crypto markets
• The reality of DeFi and whether planned maintenance on blockchains makes sense

If you’re interested in the future of tokenized assets, crypto infrastructure, and why banks still feel like they’re stuck in 1999, this is an episode you don’t want to miss.

✅ The first wave of tokenization failed due to misaligned expectations—crypto traders weren’t looking for stable, bond-like investments.
✅ Stablecoins became the ultimate “real-world asset” because they’re not an investment but a convenience, especially in regions with weak local currencies.
✅ Tezos continues to evolve with fast block times, liquid proof-of-stake, and a strong developer community.
✅ Tokenizing commodities like uranium opens up new financial markets that were previously inaccessible to retail investors.
✅ Privacy remains a core value in crypto, but regulatory pressure is making it harder to implement.

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

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

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

Global Talent Pool: Andy dives into why 85% of software development talent is located outside of the U.S. and how companies can leverage this global talent pool for competitive pricing and higher efficiency.

The Critical Role of Due Diligence: Learn how to avoid costly mistakes when choosing partners or outsourcing teams. Andy emphasizes how deep due diligence—going beyond surface-level research—can save companies millions by ensuring credibility and trust.

Cultural Alignment & Effective Teamwork: Andy highlights how cultural alignment is essential for building strong, integrated teams. He discusses using scorecards to evaluate potential partners based on various factors including language proficiency, time zone alignment, and technological expertise.

Servant Leadership: A core concept Andy champions is “Servant Leadership,” which is about focusing on empowering your service providers to do their best work in return for long-term results and loyalty.

The Intersection of Crypto & Traditional Outsourcing: Andy explains why software developers in the cryptocurrency space face unique challenges that require tailored solutions. He sheds light on how companies can efficiently build their development teams around niche expertise like Bitcoin and blockchain development.

The Importance of Building a Strong Framework: Learn why taking the time to define a framework for collaboration is essential for successful partnerships. Andy stresses that rushing into relationships without proper planning often leads to failure.

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

Episode Notes:

• Charles Wayn’s Web3 Evolution: From DLive’s decentralized live streaming platform to the evolution into Galxe, a Web3 powerhouse, Charles shares his journey of innovation in crypto.
• Introducing Gravity: The launch of Gravity, a Layer 1 blockchain designed for high-performance and cross-chain functionality, is a game-changer. Charles explains how Gravity provides a scalable, decentralized solution for bridging multiple blockchain ecosystems with lower costs and higher speeds.
• Web3's New Era of Community Building: Learn how Galxe is reimagining the way Web3 communities grow, engage, and thrive. With a rewards platform that offers customizable quests and tokenized loyalty programs, Galxe is helping projects reach their full potential.
• AI Meets Blockchain: Charles talks about the integration of AI in crypto with tools like Alva, Galxe’s AI copilot for crypto research, which empowers users and developers to explore, analyze, and optimize blockchain projects with real-time insights.

Key Takeaways:

• 06:45 - Gravity's cross-chain capabilities and how it simplifies decentralized applications' interactions across multiple blockchains.
• 13:15 - Galxe’s tokenized loyalty points system and how it can reshape reward structures for Web3 projects.
• 21:00 - The seamless integration of AI with blockchain — why Alva could be the key to better crypto research and project management.
• 28:30 - The broader implications of Gravity’s high-performance Layer 1 blockchain on the future of Web3 infrastructure.

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