Data & Dating with Ben Rosenfield July 21, 2016 I like to think that I have a pretty good handle on life, but there two things that I will never understand -reality TV and relationships. I have a general grasp on each concept, but it will take decades to answer all my questions. For example; Why are reality shows addicting as hell? What’s going on with modern dating these days? I swear, if I hear one more person tell me how they met their significant other on Tinder…. With that said, you can only imagine when I learned that Chicago tech entrepreneur and star of “Coupled“, Ben Rosenfield, had experience in both I knew I needed to sit down and chat with him. Since I had to keep the interview at a respectable length, and this is a blog for entrepreneurs and not relationship advice, I obviously couldn’t ask him everything on my mind, but you better believe I took A TON some notes! When Wear Now: How do you feel Coupled plays off of modern day relationships ? Ben Rosenfield: I believe “Coupled” dramatizes the superficiality that exists with modern dating. It takes nuances from dating applications (go left/swipe left) and texting “games” that ultimately play a big part in the millennial courting process. WWN: What were the most interesting lessons you learned on Coupled? BR: I didn’t learn any real lessons on “Coupled” related to relationships. However the most interesting lesson I learned was how a reality show is made, which was fascinating. WWN: What is your opinion on the way modern dating and relationships have evolved and work? BR: Unfortunately or fortunately, only time will tell… technology has evolved and reduced the time it takes to connect with another person. Whether it be for an intimate, social, or professional purposes. Just like how a microwave cooks food faster, it’s not necessarily better for you or tastes quite right, but it gets the job done and lets us move on. Does the time savings have positive effects, maybe? People are quick to move on when an issue arises without fear, resulting in an endless string of semi-surface connections and relationships. And when we finally do commit to a relationship, in the back of all our minds, hiding, is the thought that we are missing out on the somone more fit, smarter, better looking, more wealthy, etc… On one side, we can fail fast and find someone that really is the perfect fit for us. On the other, the search for perfection often results in making additional compromises because we’ve waited too long. WWN: How do you feel Chicago’s dating scene is? BR: I believe it’s kind of sad for a such big city. As boys become men and girls become women, Chicago society herds the gen pop into certain tracks. College, first job, girlfriend/boyfriend, second job, engaged, married, first house in suburbs (if you’re slightly more hip, you stay in the city), kids… Falling outside these tracks people become lost and Chicago becomes almost forign. Your friends become much younger before they succumb to the cycle as well. HOWEVER, for 100 days a year, Chicago becomes the most fun city in the country. With the art festivals, music, food, they are the breeding ground for relationship creation. As summer becomes fall and the weather gets cool, people link up and hibernate the winter together. WWN: The internet is a big part of the show and your personal life. How do you balance between digital life and actual life? BR: As a founder of a technology company and a bit of a data geek, I love my digital life and I believe it’s completely emerged in my real life. I love the amount of information that I can get about everything at anytime my heart desires. “Hero”, my newest startup leverages technology and allows anyone with a skill to monetize their excess time anywhere they are in the world. Completely allowing someone to detach and build a life and living off their skillset. It’s the way of the new modern world. WWN: How did you get into app making? BR: I helped a friend launch an app a few years ago and loved the creativity of it. I loved how you can build something that billions of people can use and how that product can change peoples lives. Hero can conceivably help turn 2 billion smartphone users into mini businesses, improving their lives with the extra income they can generate by connecting with people that want to hire them. WWN: Hero is the latest app you’re releasing. How did an idea like that come about? BR: I’ve alway been drawn to working for myself, I’ve also been an avid traveler. As an entreprenuer you’re are constantly putting out fires and solving problems, essentially “saving the day”. Hero is an app built by freelancers for freelancers and really epitomizes my life and what makes me most happy. Working for myself, working on what I want with who I want, wherever I am. Hero connects people to jobs and guarantees that I get paid, on time. Which is the hardest part about working for yourself, getting people to hire me and getting the funds. Photos By: Samantha Jean Photography WWN: In an interview you talked about embracing criticism. How did you come to take it so well? BR: Maybe it’s because I was responsible for myself growing up and depended on hard knocks to learn my lessons. It’s in my nature to embrace criticism, in fact, I love when people tell me I’m doing something wrong. I enjoy peoples’ perspective even when it differs from mine. I love the challenge and to be proven incorrect, I want to grow and change and evolve. I am rarely the smartest person in the room, so I do my best to learn from others. WWN: How does Chicago play into your work as an entrepreneur? BR: Chicago as a professional city to start a business is very warm. It’s in our culture to help others without any benefit other than a “pay it forward” mentality. It’s rare and completely different in the coasts. On the flip side, Chicago is also very pragmatic, which makes it difficult for the dreamer to get backing. Chicagoans are level headed, hardworking rational businesspeople that are ideal for any organization. As an entrepreneur and a bit of big picture dreamer that doesn’t follow the track, there are opportunities and there are limitations. I love Chicago, it is the town that made me, whose values I hold true wherever I am. RELATED POSTSPrina Bagia: Spring/Summer 2015 CollectionWork, Work, WorkoutSpring is that You?