This week, Josip Rupena, Founder and CEO of Milo, reveals how his company is revolutionizing access to credit by letting clients use their crypto— without cashing it out. If you're curious about real-world crypto applications, borderless lending, and leading through regulatory headwinds, this is the episode you’ve been waiting for.
Drawing on experience at Goldman Sachs and Morgan Stanley, Josip shares his journey from traditional finance to crypto-backed mortgages. Yes, buying real estate without selling your Bitcoin.
We dive into how Milo raised millions in venture capital, scaled across six continents, and navigated the volatile regulatory landscape around crypto. You’ll also hear the story behind Milo’s owl logo, why “obvious” is a company value, and how Josip keeps his team aligned and energized across borders.
Whether you're crypto-curious or a fintech founder in growth mode, this episode will challenge how you think about innovation, leadership, and the future of financial services.
Here are highlights:
-Bitcoin as Collateral: Learn how Milo lets clients buy U.S. real estate without selling their Bitcoin or paying capital gains tax.
-Crypto Myths Debunked: Why the average crypto-backed mortgage client isn’t a “tech bro” but a responsible, long-term investor in their 30s to 50s.
-From Wall Street to Web3: Josip’s journey from Goldman and Morgan Stanley to launching a global fintech startup powered by digital assets.
-Building Through Volatility: How Milo adapted through regulatory pushback, rising interest rates, and crypto market downturns.
-Branding with Purpose: The story behind the Milo name, its owl mascot, and the core company value: Simple, Fast, and Obvious.
About the guest:
Josip Rupena is the founder and CEO of Milo, a financial technology company that offers innovative crypto mortgage and lending solutions. Milo started in 2019 and has raised $24 million in venture capital from M13 Ventures, QED Investors, Metaprop, and 10x Capital. Prior to founding Milo, Josip was a financial advisor at Morgan Stanley working with international clients and financial institutions. Josip also worked at an investment firm with $1 billion in assets under management as a portfolio manager and head trader. He began his career at Goldman Sachs covering institutional private clients with over $3.5 billion in assets. Josip graduated Cum Laude from the University of Miami and majored in Finance.
Connect with Josip:
Website: https://www.milo.io/
LinkedIn: www.linkedin.com/in/josiprupena
Connect with Allison:
Feedspot has named Disruptive CEO Nation as one of the Top 25 CEO Podcasts on the web, and it is ranked the number 6 CEO podcast to listen to in 2025! https://podcasts.feedspot.com/ceo_podcasts/
LinkedIn: https://www.linkedin.com/in/allisonsummerschicago/
Website: https://www.disruptiveceonation.com/
#CEO #leadership #startup #founder #business #businesspodcast
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