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Video: Dan Gilbert Talks Candidly About Gut Feelings, Relaxing, Pitch Deal-Breakers

February 18, 2017, 10:57 AM by  Alan Stamm

Here's something we don't see every day: Dan Gilbert talks about cooking, eating, boating, traveling, sleeping and pitch meeting deal-breakers.

In a freewheeling conversation with Chicago entrepreneur Hillary Sawchuk, who's from Rochester in Oakland County, the Detroit mogul also riffs on his childhood, a pitch meeting no-no, his vision of Detroit in the next decade and -- for real -- "special theory relativity, general theory relativity, entanglement and quantum physics."


Dan Gilbert riffs on an array of business and personal topics over scotch on the rocks at Wright & Co. downtown. (Photo from A Drink With video)

Who knew?

Even Kirk Pinho of Crain's Detroit Business, who also has sat across from Gilbert with a digital recorder, is hooked. "This interview is really quite fascinating," he tweets Friday with a link. "Some illuminating questions and answers."

Sawchuk, a 2009 Oakland University journalism graduate, started and runs a five-year-old business called A Drink With -- a brands-supported web series that "shares inspiring success stories" from artists, athletes, entrepreneurs and celebrities.

That could be hokey or contrived, but Gilbert's installment isn't.

The Quicken Loans founder and member of "the downtown oligarchy," as he's tagged by Crain's editor-publisher Ron Fournier, sounds reflective, revealing, frank and humorous during an extended  back-and-forth over Glenlivet scotch on the rocks at Wright & Company. Sawchuk lobs 41 thoughtful, well-researched questions and comments in an exchange that seems relaxed and conversational.

"To come back to my hometown and have a drink with Dan Gilbert was a pretty cool experience," she posts on Facebook.

A 12-and-a-half-minute video with highlights is below these excerpts:   

Chilhood hustle: "I was always entrepreneurial. I had candy sales. I once opened up a pizzeria in my mother’s kitchen. I put my younger brother and his friends on bikes for deliveries. We used to make those Chef Boyardee pizzas and we actually put flyers in a bunch of the neighbors’ mailboxes.
"Later that week, we got calls from the health department and they closed us down. We didn’t have licenses and we were violating all kinds of health codes, so it was actually my first exposure to regulation and government."

Detroit on the brink: "Detroit is going to be the capital of the world over the next 10-15 years. . . . In my meetings with the big three [carmakers] here and Waymo —  which is Google’s automated car technology — [we talk about how they] are coming to Detroit. They are opening offices in Detroit. It’s a sea change that is going to drive the economy over the next ten years and Detroit is ground zero of that.
"We can’t blow it. That’s a big, big deal for Detroit. I’m very, very optimistic about Detroit. . . .
"I’m hoping that in 10 years, Detroit is one of the handful of technology, entertainment and marketing centers of the United States or maybe the world. People like you for instance, who have their own business, 30 years old -- they’re a creative class, this is the place to be. This is where the action is."


Chicago entrepreneur Hillary Sawchuk, a 2009 Oakland University graduate, shares drinks and well-prepared questions.

Appeal to young professionals: "We just had an interesting thing in the middle of the winter called a 'Winternship.' We had six kids from Brown and six from Harvard. They came here for two weeks and we put them on a project, but 150 kids applied from Harvard and Brown to come to Detroit in the middle of the winter. Who would have ever thought? That is craziness. It’s really starting to have that turn. . . .
"It’s all about young people, that’s our whole thing. Your generation, young people even down to 20 years old. We have this intern program, 1,400 interns came last summer representing 210 colleges and universities in the United States and the great news was 27,000 applications came in. And it’s not necessarily Quicken Loans, it’s just this Detroit thing.
"This generation wants to impact the community more than previous ones. I use it to sell against New York and Chicago. I say, 'Look, you’re smart, you graduated from a great place, you have energy, you can go to New York, Chicago, Miami or whatever and you’ll do great.' I say, 'But what you won’t do there is see the benefits of what you’ve done in the community immediately and you’ll impact the city.'
"You can do that here. Other cities are already evolved and you can’t do that there. That’s what I use to sell people now."

No long-distance interviews: "People have 60 years of bad shit, for lack of better words, bad stuff that they’ve heard. Whatever I say on the phone isn’t going to get that out of their soul. So I always say come here and I’ll talk to you because you won’t get it unless you’re here."

Pet peeve: "If someone pitches a business plan and they throw me a financial forecast as the first thing and they talk about numbers and money, then I’m out of there as fast as I can because they are just chasing money. They don’t have a vision, a dream, a mission.
"That’s number one. I look for people who are passionate about their 'the,' whatever that is."

Bad fits -- 'sniff it out:' "I’ve learned that if somebody isn’t aligned philosophically, doesn’t believe in your mission or is about themselves first and only, you can sniff it out pretty quick. If you know at the gut level it will absolutely end, it’s just a matter of when. . . .
"If you’re in a meeting with somebody and they work for you and you’re looking at them and something crosses your mind. they are gone, it’s a matter of when. If that thought comes in your mind, it’s over.
"I don’t care about mistakes or making the wrong decision, it’s that their values aren’t aligned with you. Who you are will come out in everything you do, everything. If you know who they are, you’ll know what their decisions are, their actions, behavior.
"My issue over the years has been hanging on too long. Maybe because I was just a wimp about firing them or ending the partnership. There have even been recent things, where people have been with me for 25 years and I should have ended it years ago. 25 years!"


"It’s been a long time since I’ve been at a bar, having a drink. This is good in the middle of the day though. I’m going to try this more often."

► Average nightly sleep: "You’re hitting on a sore subject. . . . On average I probably sleep four to five hours. I stay up late."

Activities to unwind: "I go up north a little bit. I’ll go out of town and travel quite a bit, a lot of it is business. I like to read. I like to work out when I can. . . .
"I wasn’t always a boating guy except the last two years. I just like driving a boat on a nice day. I’ll take the kids around. There is something about water and the lake, it’s good."

Favorite meal: "I like food, but I’m basic. I like a New York steak medium with a baked potato and a salad. If I can get that once a month, I’m good."

In the kitchen: I make eggs. I can do over-medium, over-easy. I can scramble them, I can do an omelet. I’ll make eggs on the weekends or make my kids eggs. Egg whites I can do, too."

Vacation trips: "I like Italy, I’ve been there three or four times. I think I went to Europe for the first time like 10 years ago."

 Afternoon liquor: "It’s been a long time since I’ve been at a bar, having a drink. This is good in the middle of the day though. I’m going to try this more often."


Read more:  A Drink With


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