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GoHealth raised $50 million in funding and was named one of Inc. Magazine’s fastest growing companies in America. How did you two team up?

CLINT JONES: Should we tell you the truth or censor it?

BRANDON CRUZ: We both went to Miami University in Ohio and lived across the hall from each other in the dorm our freshman year. We ended up joining the same fraternity then shared another apartment together later in college but in the meantime we started a business called cheapshotz.com. This was when digital cameras first came out so we’d bring them to bars and restaurants to take people’s pictures and give them a slip of paper so they could go online the next day and buy the photos. Then we’d print, cut and send them out to people. This was way before stuff like this was on the internet.

CLINT: Now when we sift through all of the old photos we realize we have a lot of good blackmail material on our college buddies.

From selling party pics to creating the leading online marketplace for health insurance. What drew you to the healthcare industry?

CLINT: We started this in Chicago when we were both self-employed and had no health insurance. Our parents were like, “You need to get health insurance,” so we went onto Yahoo and Yelp and found an advertisement for an insurance agent. We clicked on the website, filled out the little form and two days later he came over to sell to us. We had no idea what anything meant or what to buy and we didn’t know how to compare what he was offering to other options like Blue Cross Blue Shield or United Healthcare. During this same time a lot of the travel websites where you could compare airlines like Travelocity and Orbitz were becoming really popular so we were like, “There’s something here. If we’re having problems with this, others are as well.”

BRANDON: For us it just turned into an opportunistic type of thing. We just took advantage of what came our way.

Going from college roommates to business partners, how has the dynamic of your relationship changed?

CLINT: Since our first house in Chicago we’ve shared an office and we still share an office today. We’re still really good friends outside of work. We might have our differences here and there but we always seem to work through it and move on.

BRANDON: In the very beginning we made a deal. We said, “No matter what happens with the business, we’re going to make sure the friendship comes first.” We’ve always kept that as number one. People always ask how we’ve stayed friends and I think it’s because we know how to argue very well with one another and we don’t take it personally. We both understand that arguments result out of having passion for wanting the company to do well.

Were there a lot of sleepless nights in the early days of the business when you were trying to get your feet off the ground?

CLINT: In reality there are still sleepless nights. There’s always something that makes you wake up in the middle of the night, some idea that came to you or some issue you have to resolve. It still happens all of the time but to see the continued opportunity and growth is amazing. Everyday you kind of wake up and pinch yourself.

Brandon CruzGoHealthClint JonesClint Jones and Brandon CruzYolk Bloody Mary

Do you remember what you did with your first big paycheck?

CLINT: I still remember getting it. It was a big check from an insurance company for the biggest deal we’ve ever done. We both had 50 or 60 grand in credit card debt at the time so we took the money, built the software we needed and had some left over so we paid off our credit card debt. It was a struggle for awhile!

What would you say is the biggest difference between the two of you?

CLINT: I would say I’m more aggressive at times and he’s probably more conservative. I think it’s good because it’s a nice balancing act with business deals and initiatives. There is a good pull and push that keeps us grounded.

You are part of this year’s Techweek100. What excites you most about Techweek coming to Chicago?

BRANDON: For something that started as a little conference it’s exciting to see the momentum it has gotten and the companies and people involved with it now. Big things are happening this year and it’s amazing to see how everything is coming together. It’s great seeing the involvement of the community in terms of wanting to get together and talk about what’s going on in technology and what’s going on within their businesses.

CLINT: Even five years ago you didn’t think of Chicago as a technology hub so it will be exciting to see where we are even five more years from now.

Mayor Rahm Emanuel recently commended you for having brought over 250 jobs to Chicago. What surprised you most about him?

BRANDON: Just how down to earth and practical he is. We had a couple of dinners and meetings with him, he’s very passionate about doing what’s right for Chicago and he’s very committed to bringing job growth to the city and that’s great for us because we need to hire people and he’s very much behind that.

Best piece of entrepreneurial advice you’ve been given?

BRANDON: Passion shows throughout, that’s number one. If you have passion about what you are selling or what your product is it’s going to bleed over. Number two is to surround yourself with good people. At a really early stage of your business you’re advised to get a board of advisors and bring in some seasoned veterans who you can bounce ideas off of or discuss challenges and say, “Listen, we’re in this weird situation. What advice can you give me?” Because now it’s not about you, it’s about the group who can help you out.

Brandon Cruz and Clint JonesYolk CoffeeKIRSTEN MICCOLI PHOTOGRAPHY

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