Inside the World's First Crypto Mortgage with Josip Rupena

Josip Rupena talks about how his company Milo, created the world's first Crypto mortgage. Josip shares how his background in investment banking led him to found his company, which solves financing challenges for high-net-worth international clients and later Bitcoin holders who struggle to qualify for traditional mortgages despite significant wealth.

He explains how Milo created the world's first crypto mortgage in 2022, allowing clients to buy U.S. real estate without selling Bitcoin. Josip highlights that Milo's products give clients flexibility, preserve upside in both real estate and Bitcoin, and address gaps left by legacy financial institutions in a changing economy.

We discuss..

• How Josip's career in investment banking exposed him to the challenges high-net-worth individuals face when trying to access traditional lending, especially international clients with wealth but no U.S. credit history.
• He founded Milo to address these gaps, initially focusing on helping global investors buy U.S. real estate without relying on outdated borrower requirements set by legacy banks.
• Traditional banks are reluctant to serve clients outside narrow profiles—such as W-2 earners with U.S. tax records—leaving wealthy entrepreneurs and international investors underserved.
• In 2022, Milo pioneered the first crypto mortgage, allowing Bitcoin holders to directly purchase U.S. real estate without liquidating their coins.
• By using Bitcoin as collateral, clients can avoid triggering capital gains taxes while continuing to benefit from potential long-term appreciation.
• Milo structures its loans with institutional partners and securitization, bridging the gap between innovative lending products and traditional capital markets.
• Crypto-backed loans offer borrowers quick access to liquidity while being overcollateralized to protect Milo and its investors from volatility risks.
• Milo's approach demonstrates how fintech can expand financial inclusion by designing products around real client needs rather than forcing clients into rigid bank standards.
• By enabling clients to hold both real estate and Bitcoin, Milo gives them a way to compound upside across two asset classes while maintaining flexibility and financial control.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Douglas Heagren | Mergent College Advisors
• Diana Perkins | Trading With Diana

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For more information, visit the show notes at https://moneytreepodcast.com/crypto-mortgage-with-josip-rupena