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In 2014, someone sold 144 Bitcoin to buy a modest $100,000 home in the United States. At the time, it felt like a sensible decision, trading a volatile digital asset for the stability of real estate. Today, that house is worth about $250,000. The Bitcoin? Worth over $10.8 million.
Years later, that person became a client of Josip Rupena, who now runs Milo, a fintech company built specifically to prevent stories like this one.
“That’s the kind of story we’ve seen too many times,” Rupena said. “It was a good life decision owning a home for your family. But financially, a lot was left on the table.”
Those stories are the reason Milo exists.
Founded in 2019, Milo is a US-based financial technology company that allows borrowers to use Bitcoin as collateral for home loans, enabling them to buy property without selling their crypto.
The idea challenges one of the most entrenched assumptions in personal finance: that digital assets must be liquidated to unlock real-world value.
For Rupena, a former Goldman Sachs and Morgan Stanley advisor who worked with international and high-net-worth clients, the problem was clear long before crypto entered the mainstream. Traditional credit systems were not built for global, asset-diverse consumers. Bitcoin merely exposed the gap.
Rupena’s career began in the heart of global finance. At Goldman Sachs, he worked with institutional private clients overseeing billions in assets.
He later moved to Morgan Stanley, advising international clients and financial institutions, before becoming a portfolio manager and head trader at a registered investment advisor managing over $1 billion.
Across those roles, he saw the same friction repeat itself: wealthy, globally mobile individuals struggled to access US credit not because they lacked assets, but because those assets didn’t fit conventional underwriting boxes.
When Bitcoin adoption accelerated, the mismatch became more pronounced.
“The existing ways for crypto consumers to access home credit left them with unintended tax liabilities,” Rupena explained during an interview with The Bit Gazette.
Selling Bitcoin for a down payment often triggered capital gains taxes and permanently removed exposure to an asset many holders believed in long term.
Milo’s solution was radical but simple: combine Bitcoin’s liquidity with real estate’s stability.
Milo began lending in 2022, introducing what it calls the first crypto mortgage product. Borrowers can finance up to 100% of a home’s purchase price by posting Bitcoin as collateral, without selling it.
The timing, however, was brutal.
Interest rates surged. Crypto markets collapsed in late 2022. Capital became scarce. Skepticism was widespread.
“Lots of emotions,” Rupena admitted. “Pride in creating something people can actually use. But also the difficulty of championing something that didn’t exist before having to explain it over and over, sometimes running through walls.”
Many doubted the product could survive volatility. Bitcoin’s drawdowns raised fears of margin calls and forced liquidations — a familiar risk in crypto lending.
Milo addressed this by design.
Unlike traditional crypto loans, which may trigger margin calls after a 20–25% price drop, Milo’s crypto mortgage structure allows for roughly a 65% drawdown before additional collateral is required. The reason: the loan is backed by both Bitcoin and the underlying real estate.
“If someone took a loan when Bitcoin was $100,000, they wouldn’t have to post more collateral until Bitcoin was around $35,000.”-Rupena explained.
That buffer proved critical. Many Milo clients originated loans when Bitcoin was between $20,000 and $40,000 levels that, in hindsight, gave them substantial downside protection.
Since launching, Milo has originated over $100 million in crypto mortgage loans. The majority of that volume came more recently, as market conditions improved and institutional confidence returned.
But Rupena says the more meaningful figure isn’t on Milo’s balance sheet.
“We’ve helped people keep their Bitcoin,” he said. “And because of that, they’ve created over another $100 million in additional wealth.”
Because Milo finances the full home purchase, borrowers don’t sell their crypto. As Bitcoin appreciated, clients benefited twice: from rising home values and from their retained digital assets.
“In a traditional mortgage, the home appreciates,” Rupena said. “In our product, the home appreciates and the Bitcoin appreciates.”
To him, that dual exposure is what makes crypto mortgages fundamentally different from any existing credit product.
Operating a mortgage business in the US means operating under intense regulatory scrutiny something Rupena embraces rather than avoids.
“Mortgage is heavily regulated,” he said. “Fifty states, fifty different rules. We’re licensed, audited quarterly, and we report every transaction.”
Milo conducts full KYC and AML checks, works with regulated custodians like Coinbase and BitGo, and complies with state-by-state lending laws. The company does not operate as a DeFi workaround or offshore lender.
That regulatory posture shapes Milo’s expansion strategy.
Before entering any new region, Rupena said the company evaluates rule of law, property rights, title protections and capital allocation risks. For now, Milo focuses on US property, but serves clients globally, from the UK and Brazil to Singapore, South Africa and Australia.
“There’s no limitation on where the client is from,” he said. “As long as the property is in the US.”
Rupena repeatedly returned to one theme throughout the conversation: awareness.
Many people, he said, sold Bitcoin years ago to buy homes unaware that alternatives could exist. Some sold $1 million worth of Bitcoin for a $1 million house, only to watch that Bitcoin grow to $5 million while the home’s value stagnated.
Milo cannot reverse those decisions. But it can offer a different path forward.
“We’re not telling people what Bitcoin will do,” Rupena said. “We’re just giving them an option, an option not to sell.”
For a generation balancing digital wealth with real-world milestones, that option may redefine what the American dream looks like in a crypto-native era.
