Billionaire Dan Gilbert has already bet $5.6 billion on Detroit's future, but money can't solve his biggest challenge

Billionaire Dan Gilbert has already bet $5.6 billion on Detroit's future, but money can't solve his biggest challenge

Dan Gilbert and Detroit 2x1

Al Goldis/AP Photo; Bedrock; Samantha Lee/Business Insider

Dan Gilbert, best known as the owner of the Cleveland Cavaliers NBA team, is building a Detroit empire.

  • Dan Gilbert moved his mortgage company Quicken Loans to downtown Detroit in 2010 and founded his real-estate company Bedrock a year later, when the city was just a few years from bankruptcy.
  • Bedrock has invested or allocated a total of $5.6 billion across 100 or so properties in downtown Detroit and nearby neighborhoods, and said it has 98% occupancy of office and residential properties.
  • Gilbert's family of companies employs 17,000 people and is the largest employer and taxpayer in Detroit. Its level of influence on a major American city is unprecedented.
  • With this influence comes critics skeptical of Gilbert's ability or desire to transform the city in a way that is inclusive of its majority black and working-class populations - a criticism he's responded to with increased outreach and partnerships.
  • Getting the lasting support of the local community is an ongoing challenge for Gilbert, and one that will take much more than money to solve.
  • This article is part of Business Insider's ongoing series on Better Capitalism.

When Dan Gilbert was 11 years old he took a drive with his grandfather down Woodward Avenue in Detroit. He sat in the back seat of their 1971 Oldsmobile as his grandfather pointed at an empty retail location on Detroit's main drag and said there "usta be" something over there. Then he pointed out how there usta be streetcars downtown, there usta be this, usta be that.

Gilbert says that memory captures how he saw the city while growing up in the neighboring middle-class suburb of Southfield in the 1960s, and he shared it in a keynote speech with several hundred real estate professionals gathered at the Urban Land Institute's annual meeting in May, at Detroit's Cobo Center.

"Doesn't matter who you are or where you come from: I can guarantee that people have been pointing to things for a long period of time and saying 'usta,'" he said. "And when you look back at the sort of symbolic bottom of Detroit, I couldn't think of any worse or sadder word to describe it than 'usta.'"

city of detroit map

Google Maps; Business Insider

Detroit is a large city that lost hundreds of thousands of residents over decades. Its downtown, where Bedrock's development is focused, became increasingly vacant.

This is finally changing, and it's in no small part because of Gilbert, the billionaire founder of mortgage company Quicken Loans and the owner of NBA's Cleveland Cavaliers.

Over the past eight years, as media reports, films, and books churned out "ruins porn," portraying Detroit as a hollowed-out dystopia, Gilbert and his real-estate firm, Bedrock, were buying swaths of property at bargain prices and pumping in billions of dollars.

Right now there are about 100 properties in Bedrock's Detroit portfolio. Since its founding in 2011, Bedrock has invested and allocated a total of $5.6 billion into the city. Rock Ventures, Gilbert's umbrella company of more than 100 businesses, accounts for 17,000 jobs in Detroit, making it the city's largest employer, minority employer, and taxpayer.

Never before has a private entity held so much influence in a major American city as Rock Ventures holds in Detroit. And no one in the private sector is as powerful as Gilbert.

He moved Quicken Loans, now the US's largest mortgage lender and the foundation of his fortune, to Detroit in 2010 when the city, once a symbol of American greatness, had fallen into the nadir of its decades-long decline. It was three years away from declaring bankruptcy.

As Detroiters struggled with the results of years of poor governance at the city and state levels, Gilbert continued a spending spree with the aim of breathing life back into the heart of the city.

Now, for the first time in years, not only are Detroiters and Michiganders interested in what's happening downtown, but the same tourists who once gawked at the abandoned towers and blighted neighborhoods are also eager to check out what's happening.

Gilbert's imprint is all over downtown, and Bedrock's orange-black-and-white logo is ubiquitous. Bedrock's portfolio includes buildings designed by the iconic architect Albert Kahn, such as the Chase Tower and First National Building and landmarks like the Book Tower. Its most ambitious project is the Hudson's Site, once home to the flagship Hudson's department store and the future home of a mixed-use building that will feature 1 million gross square footage and an 800-foot tower that will be the tallest building in the city - all at a projected cost of $1 billion. After contributing $10 million to the nonprofit M-1 Rail initiative behind downtown's light rail system, he named it the QLine, for Quicken Loans.

chase tower detroit

Richard Feloni/Business Insider

Bedrock owns the Chase Tower, foreground, the Buhl Building behind it, and One Woodward behind that.

But a city is not a collection of properties; it's a complex web of communities. Many of the race and class tensions that are hallmarks of gentrifying neighborhoods across the country are at play in Detroit. But instead of affecting a few blocks, these tensions are on display in a city of more than 670,000 people. Detroit is the largest black-majority city in the America. The last time its downtown underwent a period of urban renewal, in the '50s and '60s, the most densely populated black neighborhoods, in an area known as "Black Bottom," were destroyed. After decades of poverty, crime, and failed attempts at rebirth, it makes sense many Detroiters are skeptical.

It's an unfortunate reality of the city's situation that it took a billionaire and his empire of companies to renovate and develop so many properties that were essentially left to rot. At this point it's not a question of whether Gilbert and Bedrock have influenced the city; it's a question of how they mean to go forward.

After my interview with Gilbert in May, as well as conversations over the past few months with people who work closely with him, local business owners and workers, the mayor, community activists, and experts on the city's history, it became clear that finding a way to alleviate community tensions through outreach and investment is crucial to bringing financial success and stability to the people of Detroit. Because there's never been a situation like this before in the US, Gilbert has had to consider societal aspects at a scale most businesspeople have never had to.

It's remarkable what Rock Ventures - most prominently through Bedrock - has accomplished in less than a decade, during a time when many had written the city off. Now it's a matter of using that influence to help create a sustainable Detroit that elevates Detroiters along with its companies, so that the city can avoid becoming a lifeless collection of renovated skyscrapers.

Building an empire

Dan Gilbert career milestones timeline copy

Shayanne Gal/Business Insider

Gilbert may be best known around the country as the owner of the Cleveland Cavaliers, which he bought in 2005, but his fortune has been built on Quicken Loans.

After getting his bachelor's from Michigan State University and his law degree from Wayne State, in Detroit, he cofounded in 1985 the mortgage company Rock Financial, which he took public in 1998 and sold to Intuit the next year. Intuit renamed it Quicken Loans, and Gilbert bought it back in 2002.

Quicken Loans became America's top mortgage company by volume last year, and remains the foundation of the ever-expanding Rock Ventures family of companies.

Gilbert, who loves motivational phrases and delivers dry one-liners in a nasally Michigan accent, is on a mission to create change. He once told ESPN, laughing, that "passive aggressive" isn't the descriptor for him. He considers himself "aggressive-aggressive."

He brings intensity to all aspects of his business.

There's the infamous open letter he wrote to LeBron James in 2010, attacking him personally when he decided to leave Cleveland for Miami. Gilbert apologized, and James eventually returned for a second run of five years, which included a championship, in 2016.

Read more: Dan Gilbert runs 100 companies according to 19 rules

There's his fight against the lawsuit that the US federal government brought against Quicken Loans, in 2015, alleging it had used fraudulent actions to approve federally backed bad loans between 2007 and 2011. Gilbert adamantly denied wrongdoing and said he refuses to settle the case, which he calls the work of a government acting in bad faith after the subprime-mortgage crisis that led to the Great Recession. Gilbert initially countersued the government in a case that was dismissed.

And there's the casino-gaming business he built, which he founded as part of a campaign encouraging Ohio citizens to vote to legalize casino gambling. He lobbied so persistently and publicly that he began receiving personal attacks from the opposition. Legalization passed overwhelmingly, and today Gilbert's company Jack Entertainment has, among others, three locations in Ohio and the Greektown Casino in Detroit.

Dan Gilbert isn't afraid to speak up, and when he wants something he makes it happen.

The scars are still there

Detroit has the highest percentage of black citizens in an American city, about 80%, and it's long been a working-class city.

In the early 20th century it was the birthplace of the auto industry, which in turn made it a shining symbol of American ingenuity and progress. "The Renaissance City" grew significantly in the 1940s with the Great Migration of African-Americans leaving the South, and Detroit's population hit its peak in 1950, with 1.8 million people. During the '50s, the city became more sprawling, with miles of single-family homes built, but the city also began losing thousands of jobs as manufacturers moved their factories.

Then, in 1967, a five-day race riot exploded after the police arrested 83 people upon raiding an unlicensed drinking club. The governor sent in the National Guard, and President Lyndon Johnson sent in the Army. After five days, 43 people had died, more than 7,200 were arrested, and there was $45 million in damage. It was the bloodiest of the American race riots that summer, and the worst since the Civil War draft riot of 1863. The incident, combined with the election of the city's first black mayor, Coleman Young, in 1974 resulted in so-called white flight from Detroit, where thousands of white citizens left in droves. A clear line between white suburbs and a black city was drawn, and many white former Detroiters grew to resent the city.

General Motors built its new headquarters, the massive tri-towered Renaissance Center, in 1977. But even its original construction reflected the city's dynamic. It was essentially a walled-off fortress, meant to separate its employees from the Detroiters beyond.

With a lack of development and increasing poverty-bred crime in the '80s and '90s, Detroit was the country's arson capital and had one of the country's highest crime rates, fueled by gang violence around the drug trade. As factory jobs in Detroit's waning auto industry vanished and crime rose, more residents left the city.

It was also severely hit by the Great Recession, which added to the thousands of foreclosed houses left abandoned throughout the city. The empty, decaying homes were eyesores in their neighborhoods and facilitated drug dealing and materials scrapping, further raising the crime rate.

Gilbert came in with Quicken Loans in August 2010, just three months after Mayor Kwame Kilpatrick was sentenced to between 18 months and five years in state prison for violating probation after an earlier sentence, which resulted from his highly corrupt time in office. In 2013, he was convicted on 24 federal felony counts; he's serving a 28-year sentence.

Detroit was a mess. But Gilbert built through this period, and when Mike Duggan became mayor in 2014, Gilbert found an ally for his vision of the city.

"His heart's in the right place," Gilbert told me of Duggan. "He has noble purposes, as does this council, too." He added, "I think you're seeing everybody swim together, upstream."

dan gilbert mike duggan

Carlos Osorio/AP

Gilbert and Detroit Mayor Mike Duggan at the groundbreaking of the Hudson's Site in December.

After President Barack Obama's administration appointed Gilbert cochair of the Blight Removal Task Force, in 2014, Duggan recruited Gilbert last year to design a proposal for Amazon to make Detroit the site of the retail giant's second headquarters. The bid, a joint effort of the state, city, and Bedrock, included an offer for $4 billion in tax breaks but was ultimately not enough to sway Amazon, which expressed concern about a lack of adequate public transportation and a limited talent pool.

Though the bid was unsuccessful, it showed that Gilbert, despite not being an elected official, has an outsized influence on where the city is headed and the backing of the state and city governments.

"The City of Detroit is much better off because of Dan Gilbert's investment in our community and we deeply appreciate his contributions," Mayor Duggan said in an email.

Detroit Bedrock City

The map below is interactive. You can adjust zoom and hover over an icon to learn more. Clicking a category hides it from the map.

It became apparent to me that although Detroiters want to see their city be successful, to have a healthy downtown and lively, safe neighborhoods, they're also skeptical, and for good reason.

Take, for example, Detroit's county jail, officially the Wayne County jail site but known locally as the "fail jail." The county began construction of a new jail in 2011 at an estimated cost of $220 million. Two years and $151 million later, the county realized it was now going to be $171 million over budget, making the jail a project it couldn't afford. Wayne County halted the project, and the unfinished concrete building stood there for years. Gilbert bought the land it stood on, along with additional surrounding land, earlier this year. Plans are not yet public for what is now referred to as the Gratiot Site, but as part of the deal, Bedrock agreed to build a new criminal-justice center two miles outside of downtown in a part of the Poletown East neighborhood, which was previously fairly barren.

Read more: Gilbert's podcast interview with Business Insider

According to a report published by the Detroit city council in May, in the past eight years Bedrock developments have received about $127 million in local tax abatements across 15 developments, and paid about $640 million in local taxes for these same properties. A study from the George Washington University School of Business found Rock Ventures paid $1.6 billion in total state and local taxes across its family of companies between 2011 and 2016.

That same month, Michigan approved a plan for granting Bedrock $618 million in tax incentives over 30 years for four of its biggest projects: the Hudson's Site, the Monroe Blocks developments, an expansion of One Campus Martius, and renovations of the Book Building and Book Tower. The incentives come in a variety of forms and include $256.3 million in state income taxes paid by employees working on the projects and $51.7 million paid in state income taxes from those who will live in the properties.

The Detroit People's Platform, an activist organization, has protested the allocation of public funds for Gilbert's projects, and sees developments like the Hudson's Site as distractions from problems like a broken school system. The organization has argued Detroit's mandated community benefits ordinances - which require a developer to allocate agreed-upon amenities to the neighborhood where the project resides (the Hudson's Site incentives deal includes a $1.7 million CBO) - to have an imbalance where the developer has far more sway than community members.

Another activist organization, the Grace Lee Boggs Center, is publicly critical of Gilbert. I spoke with members Shea Howell, Richard Feldman, and Myrtle Curtis, who agreed that they see Gilbert as an inevitable corporate force. They said his developments - kicked off with Quicken Loans moving in eight years ago - are creating, in Howell's words, a "white island" downtown in a majority-black city.

grace lee boggs

Richard Feloni/Business Insider

Richard Feldman, Shea Howell, and Myrtle Curtis see Gilbert as an inevitable outcome of the city's path, but believe lasting progress will have to come from grassroots change in the neighborhoods.

I heard variations on this theme repeatedly: Gilbert is making a big difference downtown, but it's not just downtown that needs it.

Angela Branch is the owner of the downtown sandwich shop Wala. She told me she doesn't think Gilbert has nefarious motives, but she understands why some Detroiters do, saying that while sparking development downtown is appreciated, the majority of Detroiters are living in neighborhoods that still contain blighted homes or lack basic services. "It just - it doesn't translate to the people," she said. "And it makes him look like the big mean white guy, billionaire white guy trying to take over what the people who have been in the communities forever have been trying to get to. There's a disconnect."

Branch told me her feelings about Gilbert are complicated. She'd prefer he spend more of his money in the neighborhoods, where she believes it could have a bigger influence. "I mean, in many cases, he's like a doggone godsend, but in others, it's just, like, this is not going to bode well downstream, decades from now," she said. "We'll be all living in Gilbertville."

A public-relations disaster last summer seemed to amplify the fear of this narrative coming true. A Bedrock ad featured a crowd of mostly white people with the slogan "See Detroit Like We Do" and immediately became a major local story for a news cycle. Gilbert had the poster taken down and released an apology on Facebook. He showed that it was the first of a series of posters that represented a diverse group of people, but didn't defend it. He said that he didn't personally approve the campaign, and that even if all the posters had gone up at once, he still found the slogan demeaning. ""Who cares how 'we see Detroit'?!" he wrote on Facebook.

Gilbert told me the argument that Bedrock's initiatives overlook people living in the neighborhoods is "completely false." He has invested so heavily in downtown first, he said, because he sees the neighborhoods and downtown as inextricably linked.

detroit neighborhood

Richard Feloni/Business Insider

Gilbert said Bedrock's downtown developments are contingent on improved neighborhoods, as well. There are many that are not nearly in as good as shape as the one above.

"I don't know if there is anybody, or any entity, governmental or nongovernmental, more active in the neighborhoods than we are," Gilbert said. "I don't like to go around bragging about it - like maybe that's our problem - but we care deeply about the neighborhoods, and ... we just think it's all on the same side. There's no way businesses can be successful by having really bad neighborhoods in a successful downtown. It just doesn't work that way."

He pointed to several of Rock Ventures' "for-more-than-profit" neighborhood initiatives: It accumulated data on thousands of properties for the Blight Removal Task Force. It led a free, yearlong project to create an electronic database of virtually all public high-school transcripts dating from 1950. It invested $5 million into the Rehabbed and Ready program, a partnership with The Home Depot and the Detroit Land Bank Authority, which has paid back taxes on about 60 foreclosed single-family homes and renovated them to go back on the market.

Quicken Loans also created the Quicken Loans Community Investment Fund in collaboration with the United Community Housing Coalition. It's a home-ownership-education effort that has allocated $500,000 to hiring local canvassers to offer educational services to thousands of Detroiters.

Aside from those initiatives, Bedrock has a number of properties outside of downtown, including Brush Park City Modern, a development of 400 houses, 20% of which are affordable housing for seniors in the Brush Park neighborhood, and the massive, $300 million Brewster-Douglass in the same neighborhood with a plan that will include 913 residential units (a quarter being affordable housing), public space, an early-childhood-education facility, and a small hotel.

At the Grace Lee Boggs Center, Curtis told me she's seen the literature Quicken Loans and Bedrock distributes around Detroit about its initiatives. "It is not an invitation," she said, "it is, 'This is what's going on - isn't it great?'"

Going beyond business

Everyone seems to have an opinion about what Gilbert could do differently, even those who largely approve of his work.

"He's a visionary, and he definitely has a mission he wants to accomplish, but I think he also needs to continue to be very cognizant of the inclusiveness of the city," said Aaron Foley, author of "How to Live in Detroit Without Being a Jackass."

Foley oversees and local programming as the first "chief storyteller" in the mayor's office, and he recognizes that some Detroiters - not unlike Curtis - could view Gilbert's work as imposed on the city, even if it benefits them. Any project that infringes on Detroit's proud, majority-black culture would inevitably fail, he said.

aaron foley detroit

Richard Feloni/Business Insider

Aaron Foley is the "chief storyteller" for the mayor's office, and is the author of "How to Live in Detroit Without Being a Jackass."

"Gilbert should follow the mayor's model of going to Detroiters' living rooms," he said, referring to the weekly house parties Duggan has across the city, which serve as casual town-hall meetings where he can hear what's top of mind in specific neighborhoods.

Gilbert may not be making house calls in the near future, but there are clear signs he's aware of what Detroiters want.

Candice Matthews is the cofounder and executive director of Cincinnati-based startup accelerator Hillman, which empowers startups led by women and people of color, both underrepresented in the venture-capital space. She met Gilbert last year when she was looking for funding. Her cofounder, Dhani Jones, had known Gilbert for several years, and Jones was so taken with Rock Ventures' mission that he moved to Detroit this summer to work for Gilbert and run a $1 million fund for minority entrepreneurs in Detroit.

Matthews told me that while she is not partnered with Rock Ventures, she remains in touch to share intel on rising minority-led startups. Matthews said her view from the inside proved to her that there was a genuine desire on Gilbert's part to have his role in the transformation of Detroit be inclusive, and that any missteps along the way were due to the unprecedented nature of the project.

"I think it's really hard being the maestro," Matthews said of Gilbert. "It's really hard being the one that has to look at all the numbers at a macro level and figure out how you make adjustments for culture."

Last year Quicken Loans launched its inaugural Detroit Demo Day, a pitch competition for Detroit startups, with a $1 million fund. By the time of the second annual Demo Day, Matthews told me she'd already seen a more deliberate effort to be inclusive. Not only was Rock Ventures more explicitly speaking about this effort, she said, but there were there more investments in minority-led startups.

Gilbert also recently appeared with Jones at the National Association of Black Journalists conference held in Detroit, where they announced that the Afrotech conference for black tech entrepreneurs would be held in Detroit in August.

Regina Gaines, president and managing partner of the House of Pure Vin wine shop downtown, located in a Bedrock property, considers Gilbert a "mentor and a friend." She told me she sees him as a champion of lifelong Detroiters, and that he should not be blamed for all of the difficulties happening in a time of transformation. "Detroit is going through economic, demographic, social, and psychographic changes simultaneously," she told me. "The change is happening at warp speed," she said, adding that there are Detroiters "getting left behind." The opportunities are plentiful, but communication is poor.

regina gaines dan gilbert

Dontae Rockymore

Regina Gaines has her wine store, House of Pure Vin, in a Bedrock property, and said that Gilbert has been a mentor and friend.

Gaines said she recognizes that she's benefited from a variety of entrepreneur programs, including those from Goldman Sachs, JPMorgan Chase, and Quicken Loans, but it's because of that privilege that she also feels responsibility.

"If I do my part and teach others how to launch, compete, and sustain in the new Detroit economy, there will be more conversations about the success of black Detroiters benefiting from the revitalization of Detroit," she said. "This is where it starts. We all have a part to do. It is not just on Dan Gilbert."

Trust the process

Robert Fishman, a University of Michigan professor of urban planning who has extensively researched Detroit, told me that he's optimistic about Gilbert's version of renewal. He said that the urban renewal of the 20th century began with the concept that the current version of downtown was obsolete and had to be started all over, including making way for things like highways through vast destruction. He appreciated that, in contrast, Gilbert is retaining the Woodward Avenue corridor - that same boulevard he drove down with his grandfather at age 11.

"For the most part, he's staying within the traditional framework of downtown Detroit, going back really to the Woodward plan of 1809," Fishman said. "Some of the big chunks, they are these massive areas that are still empty. But when he can, it seems to me that he's, as I say, staying within the liveliness and the real power of downtown design."

He continued: "Downtown Detroit will never be a bonanza like it was in the '20s, but it will at least have turned around sufficient to generate the funding for schools, neighborhood developments, parks - just a functioning city government."

Fishman said it's important to keep in mind that Metro Detroit, the southeastern portion of Michigan including and surrounding the city, has essentially never lost its 4.3 million overall population, even as Detroit languished. That flight from the city is part of an ugly history, but Fishman's point is that if the city comes back, the region can support it, unlike comparative places like parts of postindustrial upstate New York.

It was apparent as I spent time both downtown and in some of the neighborhoods that Detroit is still in the early days of its recovery. I saw few police vehicles, and when my hotel had a fire alarm (ultimately false) go off at 2:30 a.m., it took about 20 minutes for the fire department to show up. During the Urban Land Institute's conference, the downtown seemed to bustle with people, even during work hours. It was significantly quieter once the real-estate-developer crowd went home. When I boarded the Q Line, it stopped after five minutes and discharged its passengers to walk the rest of the way (a representative for M-1 told me that M-1 has been working with the city to reduce blocked tracks as residents adjust).

q line

Carlos Osorio/AP

The QLine light rail heads down Woodward Avenue shortly after launching last year.

Despite all this, there is a real sense that change has come to the city. Whereas tourists once walked to see soot-stained crumbling buildings built in the '20s and '30s, they can now take in buildings that no longer look like ruins from a lost civilization. Multiuse properties in progress, like Hudson's Site and the Shinola Hotel, will bring contemporary shopping and event spaces in hopes of keeping tourists and new residents around a bit longer than they otherwise would.

As for how this project could withstand a potential recession in the near future, Bedrock says it has 98% of its office and residential properties filled, and that there is a waiting list for tenants for properties in development.

In the time since I visited Detroit in the spring, Ford bought the 18-story Michigan Central Station. The long-abandoned rail station was perhaps the most iconic image of a dead Detroit, and it's hard to imagine Ford wanting to turn it into a development lab without the developments the city has undergone in the past few years - many of which Gilbert has been behind.

This current "rebirth" of Detroit is in its nascent stage. It will be yet another meaningless cycle of growth and decline if it cannot get the support of real Detroiters throughout the city and be accompanied by lasting institutional changes at the government level to sectors like public education and infrastructure. A vibrant downtown is not going to be enough to persuade people to move to Detroit if there aren't resources in place that encourage them to establish roots.

But Gilbert is making a long-term bet on the city. As he said, Detroit isn't a short-term project for him. "Projects come to an end, right?" he told me. "So I guess I would call it a process."

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