‘In a rapidly growing company, you feel you are in a different organization every four to six weeks’: A day in the life of Milo founder and CEO, Josip Rupena

While the concept of leveraging against crypto is not new anymore, lately a few companies are applying the model to mortgage lending. Using cryptocurrency as collateral, these firms help crypto holders utilize their digital assets to purchase US real estate.

Josip Rupena’s Milo is a Miami-based financial technology company that offers home financing solutions for global consumers. Earlier this year, Milo added crypto-backed mortgages to its suite of products, being the first of its kind for customers in the US.

Josip was born in 1984 and spent his formative years in Miami. His parents immigrated to the US from Chile and Croatia, so he grew up in a culturally diverse household speaking Spanish. In his early days, he was a competitive tennis player, which provided him a chance to travel all around the world competing in different tournaments. This opportunity proved to be an enriching experience for him as he came into contact with multicultural communities and their way of life. 

Soon after graduating from the University of Miami in 2007, he started his career working at investment banks. He joined Goldman Sachs as an analyst, researching companies' financials that wanted to go public, and later explored the private wealth management wing of Morgan Stanley.

During that time, Josip became acquainted with the challenges of moving money into the US to buy or invest in real estate. After devoting over ten years to the banking sector and gaining sufficient industry knowledge, he took the plunge of starting his own startup, Milo, in 2018.

“I think it started with a customer, and then we dived in, compiled the data, and started to analyze how many people have crypto, global wallets, and a strong desire for crypto-backed mortgages,” he said.

A growing company comes with a number of opportunities and unforeseeable challenges, but Josip has got it all sorted by maintaining a healthy balance between work and his personal life.

Here's what a day in his life looks like.

Before work: mornings and weekends are for family

My morning routine is quite simple and short. I’ve got young kids, so they wake me up early. I try to make the most of my time when I am with them in the morning, seeing how their previous day went since I arrive home reasonably late – and then I head off to work. 

The combination of having kids and a startup has been fantastic because it allows me to keep my life balanced and focused on what’s important and what I’m working towards – which is to give them a better life.

On weekends, I try to make sure to spend maximum time with my family and have breakfast together, which is the other life-balancing act. 

I go to the park with my kids and have an enjoyable and amusing outdoor time, which helps me wind down – also being closer to nature revitalizes my mind and rejuvenates me for the week ahead.

At work: locked in the office from Monday to Friday, managing clients, employees, and everything in between

Every single day at work is absolutely different. I definitely have my calendar planned out, in terms of internal meetings, external meetings, speaking to our customers, partners, and product team on how to build better solutions, and interacting with the loan team. Each new day is tremendously different from the day gone by, which I think is the exciting part about the job.

We have an office in Miami and in Colombia. The employees that are in South Florida work from the office site, and we have an optional work-from-home on Wednesdays. We do have employees in other locations as well who work remotely, but they also visit the Miami-based office quite frequently. So I would say we have a hybrid combination of both remote and on-site. 

Our team has over eleven nationalities, comprising people from Colombia and South America, which creates a multicultural environment – this also gives us a competitive edge when we deal with international clients as we can relate to a lot of different pros and cons they face in terms of willingness to invest in the US.

The bigger challenge, I would say, is of managing clients’ expectations – if it was up to us, we would provide the easiest and most seamless product, but because of catering to regulations and restrictions, the product sometimes can be a bit different than expected.

When it comes to time-management, if you’re running a company, it is very difficult to have a 9 to 5 mindset, as your mind is always thinking and engaged in creating innovative ideas. For me, it comes down to being locked in the office from Monday to Friday to focus on work. I generally sit quite late after 6 when I don’t have any external meetings – and that is the most uninterrupted, tranquil, and productive time for me at work.

My leadership style is such that my team and I have a very open communication channel for exchanging dialogue and having conversations about things. I hope they come to me when they are facing any sort of challenge in a professional or personal capacity, because I strongly believe that the sooner we detect and address a problem, the sooner we can collectively find its adequate solution. 

On the flip side, if a stumbling block isn’t addressed earlier, it becomes a bigger issue later, resulting in a tight spot. I treat all my employees in very high regard and wish nothing but success and prosperity for them, professionally and personally, but I can help them in doing so only if they allow me the opportunity to talk to them. It can be me or someone else in the team who can lend a helping hand when they are in need. 

One lesson that I feel has helped me the most throughout my professional journey is that when you are in a rapidly growing company, you feel you are in a different organization every four to six weeks. As soon as you set into a rhythm with your team, you are hiring more people. You’re looking into new opportunities left right and center, and you’re getting feedback from the ever-evolving market to be on your toes all the time. So you need to be open-minded, flexible, and adaptable at all times.