We were lucky to catch up with Diana Ossa and Josh Dobken recently and have shared our conversation below.
Diana and Josh, thanks for joining us, excited to have you contributing your stories and insights. Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?
Like for most people, 2020 was a year of change and challenges. Working from home and in complete isolation from sick family members, the uncertainty of the future started to create a lot of questions for us. At the time, we were living in a 700 square foot apartment in Seattle, Washington and working our W2 jobs as architects – a demanding profession that doesn’t have high compensation and often requires working 100+ hours a week. Our careers were cutting down on time to have any life outside of work, be present for our families, or to even think of starting a family of our own – we started to question our path.
It began with a search for better financial knowledge toward the end of 2020. Books and podcasts about everything from stocks and mutual funds to penny pinching and retirement accounts. However, nothing quite caught our attention like Real Estate Investing.
It seemed natural that two architects would gravitate toward Real Estate. It represented a way for us to supplement our salaries through the potential of passive income. Not wanting to necessarily replace our W2 jobs, it would give us a chance to rely less on our passions for design to support us. It was clear that RE was the path we needed.
And so, we consumed books, podcasts, and anything RE related with an insatiable hunger for knowledge. We began networking with other investors through instagram. We had a network of supportive fellow investors before even owning anything.
As we thought the woes of 2020 were over, 2021 came and hit us both even harder.
Early in 2021 before vaccines were readily available, Diana’s father was stricken with Covid in Medellin, Colombia. At the time, hospitals were completely overwhelmed. With only one ventilator left in the city, he was asked to make a tough decision: to wait and hope he would not need it or agree to be intubated and placed into a medically induced coma immediately. He knew there was a chance he would never wake up, but this was the only option to fight for his life.
After four months in and out of coma, battling Covid, and facing multiple lung infections, Diana’s father passed away in June.
Meanwhile, we had spent 2020 and 2021 remotely watching Josh’s father’s health rapidly deteriorate. In 2015, he had been diagnosed with multiple myeloma, an incurable blood cancer. He had already exceeded the original five-year timeline he had been given by doctors. Josh was anxiously looking forward to spending quality time with his father again in New Jersey after his project in Seattle was completed.
After several delays to that project completion date, Josh’s father passed away days later. He was just barely able to make it home to say goodbye.
2021 was sobering. We were both shown first-hand how fragile our lives are, how everything can change in an instant, and how life needs to be lived with more intention. 2021 affirmed everything we thought about the need to adjust our path.
Diana’s father never got to hear much about our new path. Josh’s father was on his deathbed as we signed paperwork for our first income property, a duplex we purchased sight unseen in Kansas City.
Losing both of our fathers while we were focused on work and on our careers will forever remind us why our priorities needed to shift, and that relying solely on our time-consuming careers for income would never align with the type of life we wanted to lead.
Really though, the biggest risk of all is assuming loved ones will always be there… that there will be time later.
With that in mind, the worst that could happen with RE was that we would go back to relying only on our jobs for income; what did we have to lose by trying?
And what did we have to gain? More time and freedom to be present with our loved ones and on a moment’s notice. A choice with how and where we live. An ability to work in design as a passion. And most importantly, a chance to start a family and be present parents.
Our path became crystal clear.
At the beginning of 2022 we jumped in head-first, knowing fully well that we would need to embrace the concept of “delayed gratification”. We moved from Seattle to Kansas City to house-hack the property we had purchased sight unseen. In doing so, we were able to offset our living costs and began the real estate journey living for free. A complete change from the luxury living we had grown accustomed to, the move to Kansas City also allowed us to build our core team and gave us an opportunity to be able to focus on scaling our portfolio.
Looking back at our first year in KC, we have purchased four doors, two of which are generating income with another undergoing renovations (finishing soon) while we live in the fourth. We have created partnerships with some fantastic individuals and are looking at even more expansion moving into 2023!
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
We are both are architects, designers, and real estate investors. Diana was born in Medellin, Colombia and moved to the US for college when she was 18 where she went to school for Studio Art at Grinnell College in Grinnell, Iowa. Josh was born in Red Bank, New Jersey and studied Finance with a minor in Architecture from Syracuse University. We met at Washington University in St. Louis while pursuing our Master’s in Architecture and Master’s in Construction Management.
Currently, Diana works as an architect for Seattle-based firm Mithun, recipient of the 2023 AIA Firm Award. Her primary focus is in the design and presentation of large multifamily housing projects, particularly student housing.
Josh currently works as a designer for Populous, an international firm based in Kansas City focused on sporting venues and other large scale projects. Josh was part of the team that designed and constructed Climate Pledge Arena in Seattle, which has won multiple awards and has been called the most progressive, responsible, and sustainable arena in the world.
Together, we began real estate investing in 2021 in Kansas City, Missouri and Medellin, Colombia. We currently have 5 doors, and are focused on value-add properties, rehabbing and using our design and construction skills to improve properties to provide beautiful spaces to our tenants. We use a mixture of short, medium, and long term rental strategies.
We are also starting a design consultation company where we hope to help many investors like us to design and renovate their spaces to maximize their profits and support them throughout the design process – something that scares many investors when getting started. With our experience in architecture and construction, we are also pursuing larger investment opportunities where we can take advantage of our knowledge to design and develop multifamily housing.
Let’s talk about resilience next – do you have a story you can share with us?
As is the case with many seeking to better their situation, our story began with challenges and a need to stay on track towards our goals. Losing both of our fathers is the biggest emotional challenge we have ever had to face. In the wake of those events, many told us to slow down, to try and relax, and to let things calm down a bit. Instead of slowing down, our father’s passings helped better define our “why” and reaffirmed our purpose – it motivated us to push harder and to get started sooner in RE.
Rather than waiting for life to calm down, we decided to pack our bags and move across country to pursue RE investing. We got way outside of our comfort zone. We left our beautiful apartment in Seattle, and with that our comfortable lifestyles. We kept telling ourselves that delaying gratification meant that future rewards were worth the time, effort, and sacrifices we knew were necessary.
We moved to Kansas City, a place where we had minimal connections and minimal community. Moving alone could have been considered enough of a culture shock but going from a luxury apartment to a fixer-upper home made it even more extreme and jarring.
Social events and other distractions would unfortunately become a thing of the past. When we weren’t working on our time consuming W2 jobs, we were pouring hours into our investment properties. Every hour of the day was spent focused on networking, looking at properties, analyzing deals, or doing some sort of house project.
We learned, we mourned, we cried, we kept going. We have learned how to pivot and adjust to changing circumstances, to challenges, and discomfort. All of this because we knew that if we remained on track, the delayed gratification would be worth it.
What’s a lesson you had to unlearn and what’s the backstory?
That you need to have all the information clearly laid out to take action. That failure is bad.
It’s important to acknowledge that failure is just a part of the process of success. Being afraid of failure is paralyzing in that you don’t get to learn a lesson from inaction the same way that you can learn a lesson from a failed action. The more you fail, the better your successes will be.
We have spent countless hours reading, listening to podcasts, talking, and networking with other investors, hoping to learn everything we needed in order to purchase our first property. While education is an incredible asset, there is nothing that teaches like action – education and action go hand in hand. Going through the steps, counting reps, and taking action will enhance and enrich future decisions.
Real estate has taught us that sitting on the sidelines and waiting for the perfect moment does not create the perfect moment, and sometimes you just have to go after it and trust that you will figure things out as they come up. It has taught us to be nimble, and ready to pivot, learn and adjust through the process.
Most importantly, education is an internal experience for each of us. It doesn’t allow you to strengthen the connections you have with others the same way action does. Action is a is a shared experience where you can then tap into the education of others. It grows your support network and builds trust and confidence. It also gives you a sense of perspective on the things you have learned. No book or podcast will ever teach you what taking action will. This is a lesson that goes well beyond the boundaries of real estate as well.
With real estate, there are no two deals that will be the same. Knowing and trusting that you are surrounded by the right people will help you take that leap and take action, and trust that the right path will show itself to you as you grow, learn and experience the situation for yourself.
Contact Info:
- Website: coming soon
- Instagram: d.i.fi
- Linkedin: Diana Ossa, AIA / Josh Dobken
Image Credits
Life in the Magic Hour