I was recently reading an article on Forbes on how the Mid West is slowly becoming a venture capital’s go-to destination for slow but sure investments in the Midwestern start-up scene. Ever since Groupon heated up the scene, Chicago has emerged as one of the top startup hubs in the United States, naturally inspiring a whole generation and recently described as one of the top the top 10 globally by Startup Genome. Quoting George Deebs from his article on Forbes, he says ‘The Midwest offers the highest concentration of Fortune 500 companies than any other region in the country. These same companies are all hungry for innovation, and looking for ways to partner with local startups or accelerator programs that can help their business needs’.
In my new series of Chicago entrepreneur interviews, I’d like to present to you Corbett Drummey from Popular Pays, a company with a business model that uses instagram users, where people can score free things in exchange for their popularity! In Corbett’s own words, he shares: Pop Pays shows you products worth sharing and lets you pay for products with a photo on Instagram. The more valuable photos, the more valuable products. It varies from a cup of coffee at a local shop to a shirt from a local store registered on the Pop Pays app. Corbett is one of those characters that you can easily call a free spirit. He can also come across as an artist, a tech geek or a musician. Easily. In fact, speaking to Corbett makes you feel as though you’re speaking to John Lennon from the Beatles- very relaxed and very much himself! Here’s a quick Q&A with the successful Pop-Pays co-founder.
You say you’re hungry to change the world.. in what ways did you think you would end up creating change
Decentralising advertising like uberX did for taxis and Airbnb did to Hotels.
Have you always wanted to work in technology/tech or do you think it’s a business suitable for the way of the worlds?
I have always loved tech. I was bummed in my last job that I didn’t get to work with any cutting edge technologies.
How did your education at the renouned William & Mary College help get you where you are today. Is it the oldest therefore the best?
I’ve also broken a window in the oldest building on campus! Colleges help mostly as a space for students to mature over those 4 years, which I did a lot. The biz school there helped motivate me and the entrepreneurship program and professors taught me self-reliance.
Is there a difference between the East Coast and the Mid-west in the tech scene?
Absolutely. Twitter would not have been funded here. Chicago funds revenue-first businesses with understandable biz models and precedents. The east coast is less strict in that sense, and the west coast even more so. 
How did Chicago contribute to your success?
Low cost of starting a venture and general living. Chicago is a friendlier, cleaner, smaller city than NYC. We’re the social city.
Visitor Tips?
A list of places: Big Star, Longman & Eagle, A bridge at Canal & Cermak st. that’s not very legal to climb, Gaslight coffee, Bang Bang pie, and Parson’s Chicken & Fish.
The idea for Pop-Pays came after
Beer
Did you think it was going to work?
We did not. But we had a solid background in Biz & Advertising as well as help from friends.
Special Mantras, Disciplines & learnings
– I’ve learned the importance of having a north star from Allan, my co-founder, as well as the importance of meeting people. – – From Emerson Spartz I’ve learned how to learn, as well as the importance of reading, which has given me almost all my other lessons.
– From Dan Dovaes — how to live
Travel inspires entrepreneurs and creatives everywhere, which destination recently inspired you and why?New york. There’s a talented group of entrepreneurs there who are successful, painfully hip, and still somehow easy to connect with.
What’s your goal
Haha, to live forever
June 2014, random: How do you feel about the Turkish Govt. at the moment?
I find it strange that they blocked alcohol advertising, although reportedly it’s food for pop pays as it’s a legal gray area and still a potential way for companies to advertise. Also, super surprised they were trying to ban twitter. The turkish people are very tech savvy so of course they’ll get around things like that. I’ll admit I practice Tim Ferris’ “selective ignorance” thing and don’t stay up to date on a lot of stuff like this.
The future: self-driving cars, nanobots, graphene, and 3d printers. Our culture – from burning man to TED Talks. Modern-day heroes like Elon Musk. And the prospect of growing our own team and company to contribute to the zeitgeist of these times.Do you have any quotes you live by?
Many. One that has helped immensely is simple:
“Focus on the important things”. But that’s easier said than done.
To get a similar look to Corbetts, here’s a guide:
