From UP student to Pilot landlord

How UP alum Bob Kessi became the ultimate UP landlord

By Brie Haro | April 26, 2021 11:23pm

Bob Kessi, UP alumnus and legendary landlord in 1996 (left) and in 2021 (right).

Photos courtesy of Bob Kessi, Canva by Brennan Crowder.

If you’re a University of Portland student who’s scoured for off-campus housing, chances are you’ve come across the name Bob Kessi, or maybe even reside in one of his properties. As of right now, there are 330 UP students who rent from Kessi. 

Kessi graduated from the University of Portland in 1997, but little did he know that he would go on to serve as a landlord for thousands of UP students throughout the years.

“I’ve been doing this going on 23 years,” Kessi said. “If I had to ballpark it, I would say [the number of students] is probably in the 3500 to 5000 range.”

Being a fresh graduate from UP and having lived off-campus his senior year, Kessi understood that the housing options around UP weren’t the most ideal. His senior year house was very run down and made his belongings reek of mildew, to the point where his mom made him store it all in the garage when he moved back home. 

Kessi playing baseball for UP in 1994.

Photo courtesy of Bob Kessi.

“As a college student, most of the time you're on a budget, so you’re not necessarily too concerned about certain things like that,” Kessi said. “But that's one thing I tucked in the back of my mind for creating quality housing that's both affordable but also in good condition.”

Now, Kessi owns 70 properties that serve as a “home away from home” for students, with market values that have skyrocketed since he first made his timely investments in the UP neighborhood. For example, Multnomah County property records show the 2004 sales price of one of Kessi’s properties on N. Haven street was $251,000. Its current market value, according to Zillow, is almost $750,000

Kessi believes that his business success is much accredited to the fact that he had good timing and never let an opportunity slip from his hands. 

“I had some fortunate timing of deals and of financial windows where, in the early 2000s, loans were relatively easy to get,” Kessi said. “[While] that led to the housing crisis, in my case, it allowed me to get financing to do multiple projects.”

His interest in the housing market sparked during his junior and senior years at UP when he did research on housing and the possibility of creating housing within surrounding cities in Oregon. This led to further inspection on housing amenities for people who worked in Portland but still wanted to live outside of the city. 

“I still remember the notes on [my research] saying ‘this is an interesting idea and is very relevant for the feeling right now of people wanting to live in the Portland area or the surrounding area,’” Kessi said. “That class gave me the structure to really suss out that information, and even though I didn't end up doing that specifically, that was something that caught my attention.”

New rental construction Kessi was working on in 2002.

Photo courtesy of Bob Kessi.

After graduating from UP, Kessi decided to move back home and work with his father in his construction company. He had kept his interest within the housing market and worked heavy construction with an eye of wanting to potentially get into the rental business.

Kessi decided to move back to Portland in the spring of 1998 and bought his first home right around the corner from UP. 

This is when he learned the importance of being in the right place at the right time.  

Kessi believes that with a lot of the homes he has built and deals he walked into, there was something guiding him in that direction. For instance, while living across the street from UP, he saw the neighboring house go up for sale. After a day of work, he walked over and started to talk with the owners. 

“Just because I walked next door, I was able to put in an offer, get an accepted offer, and go into contract on a house that would have been listed the next week, and would have probably had 10 to 15 offers,” Kessi said. 

That wasn’t the only stroke of luck that Kessi had run into. In the current location of Lund Family Hall, there used to be a small neighborhood of houses before UP decided to expand. They had put up orange markers saying if someone could move a house to a different plot, it was basically free.  Kessi looked into it and found neighboring lots that were available but realized that moving a house would not be as feasible as it seemed. 

“Through that process, I realized that there was vacant land, there were homes that had adjacent lots to them that were buildable,” Kessi said. “So, at that same time, I started building houses in North Portland with my freshman year roommate.”

If there was a house that happened to have an adjacent lot, Kessi would buy it and renovate the house while building a new one next to it. It soon became somewhat of a domino effect and would become the business that Kessi always dreamt of having. 

“I've learned that when you have opportunities, you need to take advantage of them and it’s important to put yourself in a position to make it happen,” Kessi said. 

Kessi working with Habitat for Humanity in 1997.

Photo courtesy of Bob Kessi.

Kessi has always been and continues to be very hands-on when it comes to his business. Former banker, Norm Donohoe, and his maintenance man, Ryan Mahoney, can attest to that. 

Donohoe helps identify funding sources and helps with consulting and structuring the financial aspects of Kessi’s business and wishes more people would do business like him. 

“He's a hidden gem,” Donohoe said, “ I really enjoy working with him, he's a straightforward, very reliable, and a really genuine guy… and I think he deals with everyone … which has been part of his success.” 

Mahoney has been working with Kessi for the past five years but has known him since going to UP and working with Kessi’s older brother. 

“I’ve met a lot of landlords throughout the years and Bob’s the best out of all of them,” Mahoney said. “Bob's got a good heart. If any of his tenants have problems, Bob takes it upon himself to bend over backward to solve that problem.”

Kessi knows how the University tries to create a welcoming community for students living both on-campus and off-campus, given that nine people in his family have gone and continue to go to UP. He hopes to perpetuate that standard for the students who rent from him

“The University of Portland is a special place that produces and attracts a special type of person,” Kessi said. “And I enjoy that connection of hearing where people are from what they're interested in doing what they're learning, as well as working with them in the housing environment.”

His first ever experience of taking on responsibility for others’ living arrangements was when he was a Resident Assistant in Shipstad residence hall his junior year. He helped cultivate the culture and spirit that is known within the Shipstad community today.  

“I did it for free room and board, but I also like building community and helping people feel like they're part of the community and part of something bigger than themselves,” Kessi said. 

His philosophy of being a student’s landlord hasn’t changed much since then, besides the fact that he crafts his own contracts. As a landlord, Kessi tries to be as upfront as possible. He says that he doesn’t want there to be any confusion when talking to a possible renter and makes sure that there is good communication between him and his tenets. 

“I’m proud of going against the grain,” Kessi said. “I'm not a landlord that is, for lack of a better term, predatory or looking to make money at any cost. Even though I have things written into the contract I just try to take care of stuff. I want the overall experience to be a good one.”

Kessi poses with learn and burn hosted by Portland Fire early building 2001.

Photo courtesy of Bob Kessi.

Junior nursing major, Mariza Rodriguez, who rents from Kessi, can testify to that and believes that the contract was clear and concise and didn’t have any follow-up questions about the rental agreement.  Anytime she or her roommates had a question concerning the house, they would receive a timely response from either Kessi himself or Mahoney. 

Kessi embraces the fact that he is a part of a young adult’s transition into adulthood and tries to help make that transition as smooth as it can be, especially for students who are trying to navigate their way of learning what it’s like to live in a house. 

“I get parents who call me from out of state and they say, ‘I was referred to you by whomever, and we just know that you're going to take care of our son or daughter.’ and that's big,” Kessi said. 

Kessi understands the responsibility he carries when letting students rent his properties and tries to put himself in those families' shoes, especially after COVID-19 took the world by storm and impacted his student rentals. 

“I'm really impressed with the tenants that I have,” Kessi said. “The majority wanted to honor their commitment and what they said they would do...and if they couldn’t I knew they had a good reason. This is an unusual year all the way around.” 

He is still trying to problem solve for the programs and classes that were cut short and extended into this summer. To accommodate, he has had to alter a number of contracts to extend the lease term through August.

Kessi believes that what helps his business thrive is how he has been able to connect with and communicate with people as clearly and effectively as he can. 

Kessi is glad that he has been able to grow his business with the help of his family and other people along the way, and urges students to stick with a career if they are passionate and determined with getting to their end goal. 

“If you stick with what you want to do if you're passionate about something if you put in the hours, and if you like what you're doing, it's going to be a success,” Kessi said. 

Brie Haro is a Reporter for The Beacon. She can be reached at