Inside the World's First Crypto Mortgage with Josip Rupena

Money Tree Investing

Money Tree Investing Podcast

Stockmarket, Valuestocks, Investing, Finance, Passiveincome, Wealth, Business, Personalfinance

4.6 • 658 Ratings

🗓️ 19 September 2025

⏱️ 65 minutes

🔗️ Recording | iTunes | RSS

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Summary

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Milo to address these gaps, initially focusing on helping global investors buy U.S. real estate without relying on outdated borrower requirements set by legacy banks.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

Transcript

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0:00.0	Welcome to the Money Tree Investing Podcast.
0:04.0	Stock market, wealth, personal finance, value stocks, invest in your life.
0:10.0	Hello, Smart Money Tree Podcasts listeners. Welcome to this week's show.
0:13.0	My name is Kirk Chisholm and I'll be your host.
0:15.0	So today I'm joined with Joseph Repenna.
0:18.0	How you doing today, Joseph?
0:19.0	Doing great. Thanks for having me on the show. Well, I'm excited to dive right in here. Got a new topic, know very little about. So before we begin, tell us a bit about your background. So I started Milo about five and a half years ago. My background prior to starting this company was working at large investment banks. I had started another business, but I was working with institutions, large individuals
0:39.4	that had pretty significant networks and helping them invest, you know, look at the world and
0:44.5	trying to see how I could helpfully make them a little wealthier. So that was the first part of
0:48.7	my career. And then, you know, through that journey, saw an opportunity to build my loan. And
0:52.7	I kind of ran out of reasons of saying no,
0:54.8	why I shouldn't do it. And then eventually, you know, had a pretty good group of individuals around
0:58.8	me that supported me and got me going. So tell us, what does you do? So Milo is a company I started
1:04.0	around the idea of being able to help people that had particular needs, you know, specifically
1:07.7	around buying homes and offering them mortgage and credit. And I started
1:11.6	the company really focused on helping international clients that were buying real estate here in the
1:16.0	US. A lot of those were my clients as a large bank. Morgan Stanley, we probably should have been
1:21.2	doing that pretty well given. We knew a lot about them and had their wealth with us. And it would
1:25.5	take a really long time. And that was something that I started to ask around and ask other individuals. Is this common? Is this something that's happening? And, you know, I think that the assumption was if there are wealthy people, they should be able to to get mortgages in other financial products, but they couldn't. And it was very slow. And, you know, the process just wasn't great. So he said, well, you know, we think we could do something around this, raised capital from investors. And, you know, we got the company
1:48.4	going with that basic idea. And a few years into it really saw similar traits with people that had,
1:54.7	you know, digital assets, you know, specifically Bitcoin. And we started asking them similar
1:58.7	questions. Do you have Bitcoin?
	...

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