Back9Booking’s Brent Robertson on Working with Family


Even if you're the world's most functional family, chances are you'd think twice between going into business with them. I mean, Norman Rockwell never painted a single portrait of a father and his son and daughters working an assembly line or sitting in cubicles, did he? And yet, more and more, it seems I hear about siblings and couples working together, even though almost everything I've ever read on the topic strongly discourages it.

Chicago startup Back9booking is the exception that proves the rule. Run by three brothers who are its CEO, COO and CFO, the company allows golfers to search and book tee times to Chicagoland golf courses. The Robertson brothers also run their father's construction business. So, it seems like the family who works together stays together. To find out why this works so well for them -- and maybe how it can for you -- I gave CEO Brent Robertson a call.

Is this the first time you've worked with your brothers?

Brent Robertson: We run a family company as well. My father started a construction-equipment business back in the mid-'90s and since graduating from college I jumped in. Here's a whole background behind it: My father started this company and he had a stroke in 2005. My brother Glenn was working at UBS, the Union Bank of Switzerland, down in Chicago. He left there to go help my dad and help his company because he was not able to work for a while. He grew the company significantly in the two years that he was basically running the company. As soon as I graduated from the University of Illinois in June of '07, I joined Glenn here at Universal Equipment. At that point we had a middle brother, and he graduated college in '05. He joined us three years later. That's when we started the Back9 venture and getting into that as well.

We still run our father's, Universal Equipment. It's an overseas sales company, so a lot of our customers are already in bed, basically, by the time we get up or shortly after we start working. So we get to work early, we take care of Universal Equipment and then we spend the whole day, basically, on our golf website.

What's it like working with them? I've read a lot of things saying not to work with family if you can avoid it.

Brent Robertson: There's definitely drawbacks and there's definitely positive things about it. It's interesting. The thing that you have to be able to do, which is the toughest part, is separate the work from the personal aspect. I think we do a very good job of that. Right now, all we really think about it, and I don't know if it's being an entrepreneur or what, but a lot of the time outside of work I'm still constantly thinking of how we can improve our website, what we can do. I don't sleep because I think of this stuff.

But when we get together for family occasions -- we all live in the West Loop, so we all live within three blocks of each other, so we do see each other a lot even outside of work, socially. We play on intramural sports teams together and so forth. But the tough part is separating the work aspect from the personal relationship aspect. If you can do that, then, I think it's fine to go into work together. If you're working, and everybody's working together and something's not getting done during the day and it's affecting the business, you just have to be honest and straightforward and say, "You need to do a better job on that aspect." It is tough because it's family and it's tough to tell a family member to pick up and start working harder and improve. But we're all partners in this thing together so we don't see anyone as the boss. That almost creates a different dynamic as well.

But you are the CEO.

Brent Robertson: Yeah.

So you're kinda the boss.

Brent Robertson: I'm kinda the boss. [Laughs.] The reason we decided that was really because all three of us are founders of the company and we play to our strengths. I'm more outspoken. I can talk to people and go to golf courses and sit down with the general managers and owners and operators and talk all day. I think that's a big part of being a CEO, the selling side of the whole thing.

Do you think family members thinking of going into business together should lay down ground rules to establish roles like that?

Brent Robertson: It was such an informal thing when I started with Glenn back in '07. While we didn't really define exactly and say, "Hey, I'm your boss and you need to do this, you need to do this," it was more, "Hey, this is what you think you can run with, where your strengths will be best used and go with it from there." We're not really in each other's hair. We do a meeting once a week. We're in the same office so if there are issues we can talk to each other, and we're sitting on the Internet and Gchatting each other and so forth, but we have a meeting once a week where we go through everything that everybody's working on, the progress they've made, the issues they have and if something of an emergency arises where everybody needs to speak to each before then, we are all right here. We can do lunch together very easily and talk amongst each other.

My biggest advice would be to find a way to separate the personal side from the business side because at the end of the day the most important thing is definitely maintaining a healthy relationship with them as brothers. It's more important for me to have them in my life as brothers and family members and close to them in that way than it is to be business partners. Outside of work, when we get together for birthdays or weddings or whatever it is, you just have to find a way to make it all personal. Leave the work aspect at work, because our wives and our fiances and significant others don't want to hear us sitting there talking about work all the time. 

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a columnist for EGM. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.

Contact Us