Bitcoin = Home: The Mortgage Revolution No One Saw Coming with Josip Rupena of Milo

Josip Rupena joins Charlie to talk crypto mortgages, Bitcoin homeownership, and how Milo is helping HODLers unlock homes — without ever selling their coins.
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.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)
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