Images courtesy of Breakwater Chicago

How was the idea for Breakwater Chicago born?

"I came up with the idea for Breakwater Chicago after my business school internship at The Venetian in Las Vegas. I observed that Chicago had not yet picked up on the trend of daytime entertainment—something which had become a significant part of the offerings at properties in Las Vegas. At the same time, as an avid sailor on Lake Michigan, I noticed that the city's massive boating community had no destinations once they left the harbor. From there, my goal was to create the Catalina Island of Chicago—a luxurious offshore destination for boaters and non-boaters alike."

How did your family and friends respond when they heard the idea?

"When I first told my parents, I think they were a little skeptical. It's a big idea that's way outside the box, so most people's initial reactions were of excitement, with a healthy dose of skepticism. As I started to do my diligence on the concept, it seemed that everybody began to see the opportunity and they eventually became as excited about Breakwater Chicago as I was. I have a very close family, and I'm positive that I would not have made it this far without their help and support."

What's been the most enjoyable part of the process, what's been the most challenging?

"The most challenging part of building the concept and business plan for Breakwater Chicago has been convincing people that it's more than just a crazy idea. I have to convince everybody when they first hear about the concept that it can and is happening. Once people throw questions at me, expecting to find holes in our plan but finding that we have answers to every question, that's when folks typically start to see the validity of the business.

"The most enjoyable part was just last week when we announced the project to the public, after two years of pouring in sweat, blood, and tears. The public's reaction to Breakwater Chicago was overwhelmingly positive, and I spent the entire week running (literally!) from interview to interview. I am still trying to reply to all of the emails, texts, and social media messages of support from friends, family, and total strangers."

How would you respond to skeptics who question whether such an ambitious project is possible?

"It is not uncommon for somebody to judge my book by its cover, especially because I am fairly young for a project of this magnitude, and my name doesn't resonate with locals as being powerful like some of the long-standing wealthy families in Chicago. If I sense that an individual does not 'believe,' I will typically just challenge them to try and stump me with a tough question. Over the last two years, we have been able to put together solid answers to just about every question we've heard, so there are very few times I get stumped. Having all of those answers gives skeptics the confidence to at least listen to the full story. If I do get stumped, and it has happened once or twice, I am quick to say that I'll find out and get back to those people. Then I'll work tirelessly until I have that question fully answered."

How have you used what you learned at HBS in this work?

"If there was one thing HBS taught me that has been invaluable throughout the last two years, it's been to put yourself in the other person's shoes. Every case study that we read forced us to think about difficult business situations from the perspective of protagonists such as CEOs, engineers, accountants, and even celebrities or athletes. Before every meeting or call, I spend at least a few minutes thinking about the upcoming interaction from that person's shoes. More often than not, it helps me focus on benefits and avoid pitfalls."

Which HBS professor had the greatest impact on you, and why?

"I feel like this is a trick question! There are so many amazing professors at HBS, and I had the pleasure of taking courses with some of the best: Rakesh Khurana, Clayton Christensen, and John Macomber just to name a few. But the one that had the greatest impact on me would have to be Jan Rivkin, who taught my section Strategy. Professor Rivkin is not only the most genuine and humble genius that I know, but he has a way of making a personal connection with students that, I'm guessing, most remember for a very long time. Plus, once he found out that my grandmother was a tech-savvy woman, Professor Rivkin would always ask, 'What would Grandma D'Arcy do?'"

What advice would you give current HBS students hoping to launch their own business ventures?

"I heard a lot of advice as I was building my businesses; I had two prior start-ups which failed. The point that always hit home with me was, work on something that you love, and the money will follow. My first two businesses were ideas that I thought could be successful and I found them interesting, but I didn't realize until launching Breakwater Chicago what it feels like to truly 'love' what you're working on. I would suggest that students take time to think about that and not just jump to whatever the fad of the year is for start-ups. Also, don't be afraid to start a business that's not technology based."

What do you think will happen first—a Breakwater Chicago concert on Lake Michigan featuring Chicago's own Smashing Pumpkins or a Cubs World Series win?

"As somebody who hates taking trade-offs, I would have to say that we'll celebrate a Cubs World Series win with a Smashing Pumpkins concert at Breakwater Chicago. We may need to build a second vessel for that one, though!"

Can you finish this statement? "A great entertainment experience is…"

"' ...one that never ends.' Patrons should have such a positive experience at a venue or event that they relive the memories with social media posts and storytelling for years to come. I still talk with my high school friends about driving up to Soldier Field in Chicago from the suburbs for a Dave Matthews concert and that was 14 years ago."

Follow Beau D'Arcy on Twitter at twitter.com/BeauDarcy.

Learn more about Breakwater Chicago at www.BreakwaterChicago.com.

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