Chris Kostoulas is the co-founder and COO at Peek, an end-to-end solution for virtual-first leasing in the multi-family space. Peek works with luxury real estate developers and property managers in the Chicago area and across the country.
Prior to founding Peek, Chris began his career as a convertible bonds and derivatives trader at Morgan Stanley, and then built an impressive track record in operations, product and business development as one of the first 300 employees at Uber.
Tell us about your background. Where did you grow up, where did you go to school?
I grew up in Manhasset, Long Island, a suburb about 30 minutes outside of NYC. I was lucky to be surrounded by a huge Greek family growing up. I had 11 cousins in the same school system at the same time as me!
At college, I double-majored in computer science and finance at the University of Richmond, where I studied on a full academic scholarship. After graduation, I started my career at Morgan Stanley as a convertible bonds and derivatives trader. While the environment was exciting and the team was great, I pretty quickly knew in my heart that finance wasn’t a forever thing for me, and that I wanted to get back into the world of technology.
After Morgan Stanley, I spent 6.5 years at Uber, working in operations, launch, product, and finally business development. During my time at the company, I witnessed true hyper-growth. We went from 300 employees to 25,000 by the end of my tenure. It was an educational experience like none other and I took many lessons learned with me to Peek.
How did you get your start in the industry?
I came into the real estate industry completely cold. My co-founder, Austin Lo, had spent some time as a consultant for a proptech company and as a practicing real estate agent in New York City. Austin and I were friends for a long time before starting the company. So, when Austin saw the gap in the market for a scalable virtual leasing solution, he knew my background in scaling businesses would be a great fit and he pitched me on joining him to start Peek.
When assessing the industry and opportunity, I looked at it pretty simply. I worked backwards — an interactive virtual tour is the best way to understand a space you are considering moving into. Those interactive virtual tours also happen to save the other side of that equation (agent, manager, etc.) time. I thought, a double whammy of time savings, so why don’t these exist for every unit? And with that simple line of thinking, I left Uber to start Peek with Austin.
Did you have a mentor who helped you get on your feet, or is there someone you turn to now for support?
I’ve been really fortunate to have a number of incredible mentors throughout my journey. A few in particular stand out — Rob Citrino from my days at Morgan Stanley. He truly helped me get my footing and confidence in the professional world.
Also, Kim Fennell (Former Head of Data Partnerships) and Emil Michael (Former Chief Business Officer) from my days at Uber have both really helped me grow as a business development professional. They helped me learn how to evaluate and structure great deals, and as you can imagine, that skillset has been critical in scaling Peek!
What does an average day in the life of Chris Kostoulas look like?
Typically, I’ll wake up around 7:15 a.m. and get a quick workout or run in before my morning stand-ups which start at 9:00 a.m. Every day, I do a 15-minute standup with our sales team, a 15-minute standup with our ops team, and a 30-minute sync with my co-founder, Austin. Since we’ve been a remote organization from the beginning, these syncs are critical to keeping everyone aligned and on target.
From there, every day is different, but usually full of Zoom calls with potential customers, existing customers, other companies (in a BD capacity), investors, and internal teams. In between the calls, I’ll usually get lunch delivered and consume an exorbitant amount of La Croix sparkling waters.
Days will usually wind down around 6-6:30 p.m., after which I’ll spend as much time outside as possible (weather permitting).
What do you like most about your job?
I love how different every day is, but even more so, I love how much of an opportunity each day is to progress. I wake up each morning thinking, “What can I do today to push the company forward? What deal can we make? What product features can we ship? What customer insights can we learn from?”
There’s always an infinite number of things to do to help us continue to grow.
What’s fun about building a company is that when everyone is bought in, you have some traction, and you genuinely like the people you’re building with, it becomes a collective mission, not a job.
Looking to the future, what do you hope to achieve/work on that you haven’t already?
I’m excited to become more connected with the real estate industry, specifically multifamily. I really think we are in the middle of a proptech boom, and there are so many interesting people doing incredible things and trying to shake off the “real estate is archaic” stereotype for good. We’re excited to be a part of the movement and continuing to innovate for the industry.
What kind of changes do you hope to see in the industry in the near future?
I believe that AR/VR tools are going to become really interesting very soon. Real estate is one of the most obvious applications for this technology — so when a good, lightweight and scalable headset comes out (the Quest 2 is close but not quite there), I think we’re going to see some awesome applications that truly redefine the prospect journey.
How do you spend your time away from the office?
Outside of Peek, I spend as much of my time as possible with family and friends. I love to get outside, whether hanging out in Domino Park in New York City or out on the North Fork of Long Island.
I’m an avid guitar player, so I’ll play my Taylor acoustic as a way to unplug (no pun intended). I also love math and strategy games, so naturally, I enjoy playing Poker — in fact before starting Peek I was ranked as a top 1,000 tournament player globally.
