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Pioneer Square Labs Director Geoff Entress was born and raised in Pittsburgh. (PSL Photo)

As Managing Director of Seattle startup studio Pioneer Square Labs, Geoff Entress is always looking to the future. It’s necessary as he connects founders with the innovations of tomorrow.

But Entress is also deeply connected to history. He takes pride in the fact that PSL is headquartered and rooted in Pioneer Square, which he calls “‘Seattle’s original neighborhood,’ where prospectors were outfitted for their trip to Alaska during the Klondike Gold Rush of the late 1800s.”

It’s “an appropriate place [to] help prepare today’s generation of entrepreneurs and innovators to start their journeys,” he says.

As Pioneer Square was growing as an outpost for Pacific Northwest trailblazers, Entress’ ancestors were embarking on an odyssey of their own. They immigrated from Germany and Ireland in the 1800s, “so the Entress clan has called Pittsburgh home for over 100 years,” Entress said.

Like generations before him, Entress grew up in Pittsburgh. He left to attend the University of Notre Dame, returning to earn a business degree from Carnegie Mellon University’s Tepper School.

Entress has lived in Seattle for the past 20 years, working at leading venture capital firms Madrona and Voyager. In 2015, he joined PSL. He returns to Pittsburgh several times a year to visit his family and alma mater.

GeekWire interviewed Entress for this Pittsburgh Profile, a series of Q&As with some of the most influential people and interesting characters we meet during our month-long “HQ2” project.

Continue reading for Entress’ answers to our questions, and check out all of our Pittsburgh coverage here

What do you love about Pittsburgh?

Entress: What I love best about Pittsburgh is also what I love best about Seattle – the people.  Pittsburgh is full of wonderful people.  Pittsburghers are incredibly hard-working and diligent. My favorite Andrew Carnegie quote, and Carnegie Mellon University motto, is “My heart is in the work,” and I often think of that quote when I reflect on how fortunate I am to be doing work that I love doing, working with great entrepreneurs to help them be successful.

Carnegie Mellon University. (Photo by Elan Mizrahi for GeekWire)

I think Pittsburghers also have a deep sense of optimism, that no matter how difficult or challenging things seem at the moment, things are going to get better if we work hard to make it so. And we are a lot of fun! My father, who is one of my greatest heroes, has the best sense of humor of anyone I know, and I think this is typical of Pittsburghers in general – things are going to keep getting better, so enjoy the journey.

What would you change? 

Entress: Direct flights from Seattle. There hasn’t been a direct flight from Seattle to Pittsburgh since about 2000. I am tremendously excited that Alaska Airlines is starting one this summer. Will make it much easier for me to get back to my original hometown more often.

Favorite Pittsburgh spot.

Entress: The Carnegie Mellon University campus. I love visiting the university and meeting with the professors and students who are involved with entrepreneurship, technology innovation and company creation. I have been an advisory board member at the Don Jones Center for Entrepreneurship at CMU’s Tepper School of Business for years and, more recently, have been involved with the Swartz Center for Entrepreneurship there, named for fellow Tepper alumnus and Accel Partners founding partner Jim Swartz.  Every time I visit Pittsburgh, I try to visit the CMU campus and meet with the entrepreneurship program team and also try to visit other departments on campus to see what cool new things are being developed there. My 30th Tepper School reunion is in April and I am looking forward to catching up with my former classmates there, all of whom have been doing really exciting things over the last few decades.    

Favorite Pittsburgh celebrity.  

Entress: There are so many great people in Pittsburgh, but I have to give a shout out to my former boss and mentor Stan Druckenmiller. I worked for Stan’s asset management firm Duquesne Capital Management for four summers in Pittsburgh starting in 1980 after I graduated high school. Duquesne Capital eventually grew to be a $12 billion hedge fund firm and Stan is now recognized as one of the best investors ever.  He famously “broke the Bank of England” in 1992 while he was working George Soros and even tried to buy the Pittsburgh Steelers in 2008. Much of my love for investing came from those wonderful summers working with this amazing man. Stan spends most of his time in New York now, but is one of Pittsburgh’s most storied sons.

Best food in Pittsburgh.  

Entress: Pittsburgh has many great food options, but when I visit my parents and sister there, I always try to go to The Lebanese Club in Aliquippa.  Most of the week it is “members only,” but it is open to the public on Friday and Saturday evenings.  Awesome Lebanese food and my favorite is their specialty, raw kibbeh. Even if you’re not a raw beef person, definitely give it a try. It does run out, so be sure to get there early. The Mixed Plate of lamb kabobs and grape leaves is also a favorite. And, of course, for those late nights out in Oakland, definitely hit The Original Hot Dog Shop, often referred to as the “O,” for some hand-cut fries and one of their hundreds of beers.

Best insider tip for transplants.  

Entress: Go to some games!  Pittsburghers are sports fanatics and all of the professional sports teams are great (Steelers, Pirates and Penguins), and tailgates at Pitt football games are fond memories from my time growing up.

And get out of town. Downtown Pittsburgh has a lot offer, but Pittsburgh’s outlying neighborhoods have their own character and attractions as well. Falling Water, architect Frank Lloyd Wright’s masterpiece, is located in Fayette County, just 70 miles east of Pittsburgh.  It is amazing and has been an inspiration for generations of architects and dreamers.

Favorite Pittsburgh word or phrase. 

Entress: “You can’t get there from here,” often heard with “I am lost.” There is not a single straight road in Pittsburgh. Part of what makes Pittsburgh so unique, its wonderful hills, valleys, rivers, creeks and gullies, also resulted in some crazy roads.  Driving around Pittsburgh in the early 80s, I always felt lost. Thanks to GPS, things are much easier now. Maybe that’s why so much autonomous driving technology is being developed in Pittsburgh.

Pittsburgh’s most important innovation or invention.

Entress: Pittsburgh has been at the center of a lot of innovation since the steel industry started in the 1800s, but it is hard to say that anything has provided more benefit to humanity than the Polio Vaccine developed by Jonas Salk at the University of Pittsburgh School of Medicine and introduced in 1955.

How would you describe the tech, innovation and startup activity taking place in Pittsburgh to an outsider who hasn’t experienced it?

Entress: I am now somewhat an outsider myself, but I have tried to stay up to date with the innovation happening at Carnegie Mellon through my work with their entrepreneurship program and the McGinnis Venture Competition there. The McGinnis competition is similar to the University of Washington business plan competition run by the Buerk Center for Entrepreneurship every spring.  Both competitions highlight the amazing technologies and startups being produced by both universities, although you will see more robotics and manufacturing automation coming out of CMU.

What do you think are the chances of Amazon HQ2 ending up in Pittsburgh? 

Entress: I think they are great! Pittsburgh hits all of Amazon’s requirements and Pittsburgh and Seattle are similar in so many ways, that I don’t see them going anywhere else.  Pittsburgh is the perfect fit.

Can you tell us about any memorable experiences you had in Pittsburgh that illustrate the character and nature of the city and its tech/startup/engineering community?

Entress: When I was a business student at Carnegie Mellon, some of our projects required us to use workstations in the Computer Science building that were running early versions of the Andrew File System which was still in development at CMU at the time. The Andrew File System was one of the first distributed file systems and is still in use today as it provides more security and scalability than traditional file systems.  Just one example of the innovative technology coming out of the labs in Pittsburgh.

If you were parachuting into Pittsburgh as a tech/business reporter, what’s the first story you’d want to cover? Who is the first person you’d want to sit down with?

Entress: Professor Lenore Blum of the School of Computer Science at CMU.  Professor Blum is not only a brilliant technologist, but she also has been instrumental in driving CMU’s entrepreneurship program beyond the business school so that it now is a campus-wide program.  I would want to talk with her about the Swartz Center for Entrepreneurship, where she is the Faculty Director, and about all of the great companies coming out of the university.  Professor Blum is also a leader in getting more women into CS and she and Carnegie Mellon are making strong gains there, something which we sorely need here in Seattle as well.

Any other advice for us as we prepare for GeekWire HQ2 in Pittsburgh? 

Entress: Nope, you are going to have a great time and I wish I were going with you, I can never get enough time in the ‘Burgh or enough time with my good friends at GeekWire! I really love that you are doing this.

Twitter:  geoffentress

LinkedIn: Geoff Entress


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