Q&A: #1070 Chris Brown, Entrepreneur (Catered Cruises)

After the market crash of 2008, entrepreneur Chris Brown had lost everything. Homes, cars, and even a boat were all gone. But with a baby on the way, he didn’t have much time to wallow in self-pity. The business-minded Chicago native soon picked himself up by the bootstraps and created a series of successful businesses.

His latest venture, a boat-sharing service called Catered Cruises, is sure to be yet another way that Chicagoans will be able to enjoy the city and all that it has to offer during the summer and beyond.

N’Digo recently sat down with Brown to find out more about his exciting new venture.

PrintTell us about your background?


PrintI was born in Chicago but wasn’t raised here all of my life. Chicago is where I spent most of my grade school years while simultaneously traveling with my stepfather and mother to a Native American Reservation in Wisconsin call Lac Du Flambeau. My parents worked for the U.S. Government, so I had a chance to live abroad as they worked in various countries in Africa and Asia at The U.S. Embassy. After high school, I enlisted in the Marine Corps and while serving my country, I obtained a Bachelors in Criminal Justice and Exercise Science but more importantly found my first calling, helping others through personal training.

In 2008 I started a company called The Boot Camp Guy. Within 12 months, we had our first facility of 2500 square feet and today we operate out of 6000 with a real indoor Marine Corps obstacle course. As an entrepreneur, I have always felt that I needed to put more than one iron in the fire so I also created a website called theteeshirtstore.com that serves as a platform that the average every day American can use to host their own apparel store for free and create their own designs while we do the printing and send their customers the product for them.

PrintWhat is Catered Cruises?


PrintCatered Cruises is a Chicago-based boutique boat company offering affordably-priced boating packages for entertaining friends, family, or business associates. Unlike other Chicago fleets, our flexibility allows departure options in all of Chicago’s ten harbors — from Montrose Harbor in the far north to Jackson Park in the south – at the dates and times of your choice. Each cruise is hosted by an expert captain, with quality catering menus for brunch, lunch and dinner available from a locally-based husband and wife artisan chef team. Music is provided to your preference, or if you wish, you may connect your device to our on board sound system. While spirits are B.Y.O.B., we do not charge a corking fee.

PrintHow did you come up with the idea for Catered Cruises?cc


PrintLast year while renting a yacht from a boat club, I came up with an idea to allow people to experience what I had experienced on the water, but do it at a reasonable rate. CateredCruises.com was quickly developed during the summer 2015 but launched too late in the season. We were not ready as a company and during the off-season I have enlisted both captains and privately owned boats as well as hired a seasoned president to run the company. Catered Cruises is now live and operating for the 2016 season

PrintAre cruises available during many of Chicago’s attractions and festivals?


PrintAbsolutely! Customizable packages are available for all of Chicago’s spectacular attractions: Venetian Night, the Air and Water Show, Blues Festival, Jazz Festival, Lollapalooza, weekly firework displays at Navy Pier, events at Northerly Island, or simply a beautiful view of the sunrise or sunset.

We take pride in providing the highest levels of professionalism and safety standards. As a boutique boat company, Catered Cruises offers service that is highly personalized to meet our customers’ needs.

PrintWhat are some of the key things people need to know if interested in utilizing the service?



  • We are a boat sharing service that can accommodate an intimate couple of two or host an event of up to 150 people on the water.
  • Customers can make their voyage is intimate or as public as desired.
  • We only use registered, license and approved vessels by the U.S. Coast Guard as well as license and USCG approved Captains.
  • Boats are available seven days a week from 6 AM to 11 PM and can be taken down the Chicago River, out for the fireworks, cruise the shoreline, anchor down and swim in the playpen on Lake Shore Drive or get close enough to Northerly Island to hear the concerts being performed.
  • BYOB or bring their own food or have catered meals delivered by local restaurants to you before boarding.

PrintWhat’s the biggest misconception you’ve run into regarding the service?


PrintSome people have coined us as the Uber of boats but we are in no way associated with Uber. By doing so they are actually comparing us to a company using a similar ridesharing model but not to Uber directly as a company. Although we have similar ways of business, we are specifically targeting pre-approved yachts and are giving people a chance to get on the water within an hour of requesting it. There are companies that provide similar services that allow the customers to take boats out on their own or to go out with an unqualified, possibly intoxicated captain at the helm. It should not be misconstrued that we fall into that category. We are the good guys trying to make the water a safer place for all who would like to attend.

PrintWhat are your ideal essentials necessary to have for a guaranteed good time when you gather your friends on the boat?

PrintThe first thing I would need are the right people to bring on the voyage! After that I’d make sure to have the right mix of music, also you gotta remember to BYOB and food of your choice. After that, the only thing left is to pick the destination.

PrintWhat’s the biggest lesson learned since undertaking the boat sharing venture?


PrintThe biggest lesson I’ve learned is to do more research about a new industry and establish what we are selling, how we are selling it and what platform we are selling it on before going all in. After that, put the senior staff in place that are good at what they do and execute. This is essential for any business, let alone one that you are sure to disrupt the industry with by claiming a piece of the market share providing a similar yet different service than what already being offered.

PrintBest business advice you can give?


PrintSurround yourself with smart people you can trust who are good at what they do and determine how each of those individual attributes helps us as team. I’m not an expert in the boating industry or either of the other three other companies I am involved with. It was important for me to find true leader and President for all of my companies so that I can focus on what it is I do best, creating the next opportunity for us as a team.cb3

PrintName a book that changed your life and tell us why?


PrintThe book/movie/experience that change my life is listening to and reading the Secret for the first time. I learned about the power of my thoughts, words and dreams and how they can shape my life as long as I execute a and give effort to my plan and all of its parts. I’m proud to say that I’m only 39 and I haven’t worked for anyone in 12 years and I don’t have any formal business training. Putting the things that I wanted in my life on my Vision Board was a constant reminder of the path that I needed take to get where I see myself going. It was my map and although I’m not an expert in any field, I have learned with age that I don’t have to be to put things in place for all of us to be successful as a team.

PrintFavorite quote of affirmation that you swear by?


Print“Go as far as you can see, when you get there you’ll be able to see further.” I saw myself being the owner of one company when I got there I saw three more and I executed. Now that I’m there I can see the others I know I will create over time.

PrintWhat’s next for Chris Brown?


PrintI have a goal of owning at least 50% of 50 businesses by the time I’m 50 and doing so I’m going to give other entrepreneurs like myself opportunities to go into a new business or grow the business they have. How are we going to invest in those other companies to build our portfolio the of 50 businesses that I’m looking for? With the private banks we’ve created in the form of companies like thebootcampguy.com, cateredcruises.com, theteeshirtstore.com and soon hairextensiondepot.com.cb1

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