Sunday Sitdown: ex-MLB exec Ellen Prinzi on new Chicago city app

Looking for ways to experience Chicago personalized to your interests? There’s a new app for that from Olio City, a startup run by Ellen Prinzi, a former Major League Baseball operations manager and scouting coordinator. The app — downloadable free since Friday from oliocity.com or the Apple store, with an Android version due in the fall — makes recommendations based on your interests. Prinzi, 31, spoke with the Chicago Sun-Times’ Sandra Guy about debuting the app in Chicago and St. Louis. An edited transcript follows.

Question: Why Chicago for the app launch?

Answer: This is the heart of the Midwest, and Olio City, headquartered in St. Louis, is a Midwest company. Chicago is behind only Orlando (No. 2) and New York (No. 1) as the No. 3 tourism destination nationwide. There’s a thriving millennial audience, too. I love starting in the Midwest and arriving later on the coasts.

Q: How does the app learn about you?

A: You start by answering four questions. For example, users select up to three options about how they “get down” in their city. That includes “Anything Artsy,” “Nightlife, Baby” and “Hanging with the Family.” They’re asked where they’d splurge, from options such as “Once-in-a-lifetime experience,” “Shopping ‘til I drop” or “Splurge? Get real. I have kids.” Then, a learning algorithm takes over to help provide suggestions, which a user can “like” or “dislike.” The more you “like” and “dislike,” the more it gets to know you. Olio is the first to use this technology in the travel space.

The content is cute, funny and clever. We’ve hired five knowledgeable freelance food writers in Chicago.

Our secret sauce is to marry this content with data. The last great innovation in city discovery was user-generated websites over 10 years ago. Everyone knows it’s frustrating to Google “best sushi in Seattle” and then sift through the results or read a multitude of conflicting reviews. The current options assume all users are the same. The results don’t take into account your interests.

We feature guides to over 30 neighborhoods and guides from Second City’s Rashawn Scott, “Top Chef” winner Sarah Grueneberg and the co-founders of women’s workout club Shred415. Check later this month for new guides, including a Cubs and a White Sox player answering 10 questions about what they love about their city.

We include photos and links to websites, Yelp reviews and other information.

Q: How did your experience in MLB front offices help start your company?

A: Valuing relationships and managing people is the biggest thing that has carried over. And the long hours. With the Cardinals, we matched a data-driven approach with traditional scouting. With Olio City, that’s what I sought to do in combining an old approach (reviews) with a new approach in machine learning.

I was at the University of Kentucky when the Oakland A’s started the “Moneyball” approach to assembling a baseball team, using statistics, analytics and data. I spent every summer in college interning for minor league baseball teams, like the Savannah Sand Gnats, then, ultimately, for the San Francisco Giants and New York Mets.

After serving as baseball operations coordinator for the St. Louis Cardinals, they sent me to MLB scout school for helping run the amateur draft. In baseball, your talent is important. But the difference is the player’s maturity and mental strength. I love people, what makes them tick.

I also draw from my experience of having had great bosses and horrible bosses. It all comes down to treating interns the same way you treat a board member. I try to empower everyone who works for me — five employees in Chicago and five in St. Louis, of whom six are women. I have to be direct and lay out expectations, to clearly articulate what is needed.

It’s easy to blame others. It’s not always important whose fault it is. It’s learning from a mistake, so it’s not repeated, and the whole team learns, myself included.

Our company has won an international start-up competition, has investors and is getting ready to start a seed round.

Q: How do you travel, run a startup and raise a family?

A: My husband, Pete Prinzi, is a coach for the St. Louis Cardinals, on the road 82 days a year.

We have two children — Luke, who will be 5 in July, and Samantha, 4 in August. That’s the hardest part — trying to be a great mom, a great wife, CEO and all the things women do.

It comes down to having a wonderful support system. Yeah, it’s scary. It’s scary as hell. But it’s a good scary.