Brian Payne’s Next Big Idea

In the Cultural Trail, Payne had an idea big enough to transform downtown. With his latest concept, he aspires to reach much farther. Who’s ready for another ride?
Although he has given the tour more than 200 times, Brian Payne launches into his latest Cultural Trail junket with the enthusiasm of someone still trying to raise money for the first paver. Prospective donors Matt and Lee Neff roll alongside the Trail founder on Segways. Above the hum of the electric engines, Payne shares the greenway’s good news: Skyrocketing real-estate prices in Fountain Square! A 21c hotel moving into the old City Hall! The Phoenix Theatre making a new home for itself along the northern edge! The Neffs even mention their own success story. Matt, the CEO of the drug-testing company AIT Laboratories, invested in Hotel Tango Whiskey before the Trail beat a path to the distillery’s front door in Fletcher Place. Suffice it to say, spirits were higher there after that.

As the trio putters from the canal to Mass Ave to Virginia Avenue, Payne—a Meridian-Kessler resident—points out all the condos he wanted to buy before he priced himself out of downtown with the Trail. Restaurant owners like Bluebeard’s Tom Battista wave from patio tables as the man who essentially made their businesses possible whizzes past. Every so often, Payne stops at a landscaping bed or public sculpture and recalls the ancient sewer lines that had to be replaced to allow for them. “My ignorance about civil engineering played to my favor,” he says, laughing. “If I had known about all that, I wouldn’t have thought this was possible, either.”

When people like the Neffs take a meeting with someone like Payne, they know he’s going to ask them for a big check at some point. As president of the Central Indiana Community Foundation, Payne strives to grow the not-for-profit’s $800 million in assets. Philanthropic heavyweights such as Cindy Simon Skjodt and Lori Efroymson-Aguilera describe Payne, who rounded up $63 million for the Cultural Trail alone, as one of the best fundraisers they have known. On the Trail this afternoon, however, he just hopes to establish a relationship with the Neffs. He shares examples of the CICF’s projects and a few of his own long-shot ideas. And while he isn’t fundraising for any specific venture, Payne already has briefed Matt on his most promising new concept: an app that will coordinate all public transportation options in the city.

A transit app may not sound sexy. Actually, neither did the Trail. But Payne believes Indy can lead the nation in public mobility without building a $2 billion light-rail system. Coming from anyone else, the idea would be a nice thought. From Payne, the notion already has attracted a steering committee of city officials and executives. Given the international attention the Trail brought downtown, donors like the Neffs have good reason to listen when the city’s thought leader insists he can achieve something extraordinary once more.

Coasting by the new development that now crowds Fletcher Place, Matt slows his Segway to admire the improvements. “Rule No. 1 in investing or philanthropy: You have to find the man or woman who can make it happen,” he says. And in Indianapolis, few people have proven more capable of making things happen than Brian Payne.


As a boy growing up in San Diego, Payne learned how to listen—a skill that later would serve the fundraiser very well—at an early age. His father, a middle manager at Boeing, harbored dreams of wealth and recognition. “A couple of times, he got close to being an executive, but he always got smacked down,” Payne says. “We had a bar in our house, and every day I would sit across from him there after school as he poured himself a drink. I was only 12 or 13 years old, but I would listen to him complain about how crappy his day was.”

By his freshman year of college, Payne had big ambitions himself—he wanted to be a movie star. At the University of California Los Angeles, he studied theater alongside several promising young actors, including Tim Robbins. One of Payne’s friends during that period, Kyle Gass, later founded the comedy band Tenacious D with Jack Black. Gass remembers Payne as the mature one in a group of debauchers. “He seemed a little more responsible than the rest of us, a little more moderate,” Gass says. “But absolutely no one accused him of being a good actor. He definitely needed to get into management.”

After graduating from UCLA, Payne gave himself one year to land a film role. Having grown up middle-class, he wasn’t interested in waiting tables indefinitely. When that year came and went without a casting call, he enrolled in a theater production graduate program. Not long after finishing the degree, he got a job running a summer Shakespeare festival in Santa Cruz. Raising capital for the small theater group wasn’t glamorous work. Although the town was real-estate rich, not many corporations or executives resided there. As a young guy learning how to ask for money, Payne relied on a lot of $1,000 checks from small-business owners to meet his $250,000 annual budget. But he learned something important about his fundraising philosophy. Sometimes, development people he knew jokingly characterized their job as “professional beggar,” a description Payne likens today to “nails on a chalkboard.” As Payne sees it, the person asking for money has to believe that he’s selling something of tremendous value: a better community. “I’m not asking for a favor,” he says. “I’m working my ass off for donors to make sure their contributions improve their lives and the lives of their children.”

Over eight years at Shakespeare Santa Cruz, Payne grew the tiny festival into one of the most successful of its kind in the country and attracted actors such as Bryan Cranston who would become stars. Payne became increasingly dissatisfied with his place, though, both geographically and in life. He had worked his way up to a $50,000 salary, which might have been fine were it not for the fact that he lived in one of the most expensive places in the country. Newly married to his first wife, Diane, he saw no path to homeownership for the two of them. And for all its coastal beauty, Santa Cruz resisted change. The budding community builder realized he was living in a place that didn’t want anything built.

In 1993, Payne heard the managing director position was open at the Indiana Repertory Theatre, through a friend who had become the IRT’s artistic director. Although he had never been to the Midwest, he came for an interview and was invigorated by the opportunities he saw. “I was dumbfounded by how nice the houses were in my price range,” he says. “I thought, We might even be able to afford a kid!

Payne took the job. In addition to the birth of his son Jack during this period, Payne enjoyed a lot of success at the IRT. He grew the endowment from $1 million to $11 million, and wasn’t looking for another job. Seven years into Payne’s time here, however, the CEO of the Central Indiana Community Foundation announced he was leaving to head the national YMCA. One of Payne’s best friends in California ran a community foundation, and made a habit of telling Payne what a great gig it was handing out money to worthy causes. Payne thought, That’s a job I would love to have.

There was only one problem: Indianapolis is a small town. If he applied, his board members at the IRT would hear about it. And he shouldn’t have to apply, Payne reasoned. If they saw him as a viable candidate, they would find him. So he waited. And waited. After the CICF conducted its first round of interviews without success, someone on the board finally brought up Payne’s name. Ultimately, the foundation hired him. But Payne claims the board, a “risk management group” then comprised mostly of older white attorneys, wasn’t universally excited about the decision.

“Not all of us wanted to hire you,” one of the members told him in a private moment. “Do not think you’re going to turn this into an arts organization.”


Within months of taking the top job at CICF in late 2000, Payne had an epiphany while riding bikes with his son on the Monon Trail. The Monon was packed that spring afternoon. As he rode, Payne began thinking about something he had heard in a recent city meeting. Someone had suggested marketing Indy neighborhoods with rich histories and entertainment centers—Mass Ave, Fountain Square, Indiana Avenue, and others—as “Cultural Districts.” He loved the idea, but few others latched onto it because those pockets were so disconnected. What if a trail like the Monon linked them? he thought.

Although Payne’s day job was managing CICF’s $800 million and the many grants that organization gives not-for-profits, he began using the last few minutes of every meeting he had with influential people to float his idea of a downtown “Cultural Trail.” Mostly, he received polite smiles. The prospect of tearing up eight miles of streets, taking away parking, raising tens of millions of dollars, and replacing a ton of old utilities seemed laughable to power brokers such as Hulman CEO Mark Miles and Chase president Al Smith when they first heard the idea. Worse yet, Payne’s own board wasn’t behind him. Historically, the CICF was an organization that gave money away to groups with ideas to improve the city—not an organization that generated the ideas itself. Still, Payne kept pushing. He convinced longtime CICF board members Myrta Pulliam and Lori Efroymson-Aguilera to each contribute $1 million, and the Nina Mason Pulliam Charitable Trust and the Lumina Foundation to give $500,000, for the initial studies. Although the large donations could have dried up without anything to show for them, Efroymson-Aguilera remembers feeling optimistic about hers. The philanthropist, who has spent decades on the receiving end of fundraising calls, describes Payne as a natural. “He has stage presence,” Efroymson-Aguilera says. “And yet, he makes you feel comfortable. He’s not pushy. Some fundraisers are so interested in what they want that they can’t see the big picture. He sees the big picture.”

With cost estimates and engineering plans in hand, Payne felt he could finally go to then-Mayor Bart Peterson with the Cultural Trail idea in 2004. Payne’s first marriage was starting to fall apart at the time, and he needed a win. Like many of the business and city leaders who had humored Payne the last few years, Peterson expected to dismiss the Trail. “I had a million meetings during my time as mayor, but that one sticks out in my mind,” Peterson says. “I went in very skeptical. It just seemed so implausible. I thought, I like Brian, but this is just one of those meetings I’m going to have to get through. By the end of the meeting, I was completely convinced it was the right thing to do. It didn’t take two meetings, it took one.”

The City of Indianapolis agreed to provide the right of way for the Cultural Trail, but the project would be privately funded. In 2005, Payne and his team hired Rundell Ernstberger Associates to design it and R.W. Armstrong to build it. Initial estimates suggested the cost would approach $35 million. Selling his vision for a beautifully landscaped paver path that would connect every major cultural institution downtown, Payne had some early success fundraising for the concept. But he lacked a lead donor. So when Gene and Marilyn Glick’s advisors met with him and said the couple might be interested in donating $15 million if he changed the name to the Peace Trail—world peace being a passion of Gene’s—Payne faced the biggest decision of his career. After all, connecting culture was a bedrock principle of the project. “Timing is everything,” Payne says. “That happened shortly before the budget went from $35 million to $50 million, and I thought if they turned us down, we could find it elsewhere. Had it happened six months later, I might have buckled.”

The Cultural Trail label stuck. Adding the Glicks to the name, Payne also worked in a Peace Walk on one section of the Trail to acknowledge Gene’s personal vision. But shortly after construction began along Alabama Street in 2007, the global economy collapsed. With only half of the necessary funds raised and donors retreating, the entire project was in jeopardy before the first mile of pavers was in the ground. Payne turned his attention to other sources of money. The federal government had announced a massive $20 million transportation grant called TIGER, and although officials told Payne the Trail had very little chance of getting it due to the volume of competition, he was desperate for the windfall. Because the CICF still considered the project Payne’s hobby and not part of his day job, he and his second wife, Gail, whom he met at the foundation and married in 2008, spent plenty of time at home fine-tuning the wording of the petition.

“I recall one Sunday when our friend Neal Brown [owner of The Libertine] had invited us to this VIP experience at Dig IN,” he says. “The weather was perfect. We were planning to ride our bikes to White River State Park for this incredible dinner with friends. But we hadn’t polished our application for the TIGER grant, which was the only way the Cultural Trail was ever going to be completed. So we stayed inside filling out paperwork instead. There were a lot of weekends like that.”

Those weekends paid off. In 2010, the U.S. Department of Transportation awarded the $20 million to Payne and his team. The Cultural Trail had a clear path to completion.

If you’ve driven down Virginia Avenue since the final leg of the Trail opened in 2013, you don’t need a reminder of how radically it transformed the downtown landscape. With restaurant openings such as Milktooth and Bluebeard, Fletcher Place blossomed into a foodie mecca along the Trail almost overnight. Fountain Square, a long-suffering neighborhood cut off decades ago by the interstate, has enjoyed a renaissance with development projects like the $9.1 million mixed-use Forte building. The IU Public Policy Institute released a study last year that showed property assessments were up 148 percent along the Trail since 2008, an increase of more than $1 billion.

For the people selling the city to conventions and visitors, the Trail has become their primary marketing tool. When Gen Con was shopping around for other cities to host its 60,000 attendees a few years ago, Payne led the organizers on a guided tour of the new path and sold them on the idea of staying in Indianapolis. Chris Gahl, a vice president at Visit Indy, recalls an even bigger role the Trail played in 2013. “We had been trying for years to turn the attention of The New York Times to Indianapolis,” he says. “They had a freelance writer in Chicago, and we had invited her to come see the city during the Super Bowl. We had invited her to see the Indianapolis 500. But it wasn’t until the Cultural Trail opened, and city planners from Paris and Portland were coming to check it out, that we finally got her to say yes. Brian spent four hours showing her the city by bike. She went back, and in 2014, Indianapolis was on their highly sought-after ‘52 Places to Go’ list. Without the Cultural Trail, Indy does not make that list.”

As good as the Trail has been for the city’s reputation, it has been even better for Payne’s. A guy once known for running small arts organizations is now someone who Gets Things Done. In the last few years, Payne has spoken in Copenhagen, the Netherlands, Calgary, and numerous U.S. destinations about the Trail. Shelves of awards for community development line his downtown office. Three years ago, he handed off the project to a group called Indianapolis Cultural Trail Inc. that maintains it. Payne removed himself from the board, but he can’t bring himself to dissociate from the Trail entirely. When he sees withering landscaping beds along the path, he says something. When he passes one of the Trail’s contemporary streetlights that has burned out, ICTI will hear about it.

Payne doesn’t feel any pressure to follow up his big hit with another. If anything, the pressure is off. Not many people dream in eight-mile segments, let alone accomplish anything on that scale. But the prospect of having his greatest achievement behind him at age 57 doesn’t sit well, either. As he did with the Trail, Payne has been sharing a new concept in the last 10 minutes of every meeting he takes. And while it probably won’t require the $63 million his first big idea ultimately cost, the notion is in some ways even more ambitious.

“I don’t know whether an idea is a good one or not until I say it out loud,” he says. “So I’m saying it out loud.”


Unlikely as it sounds, Payne’s latest project began in an email to Indianapolis Monthly. The magazine was putting together an issue on the future of the city a few years ago, and the editors had reached out to several people for their ideas. Payne says he shot off a note about an app that could coordinate all of the public transportation options in Indy. Somehow, that email failed to reach the editors. The idea was never published. But the more Payne thought about the app, the more it made sense. Indy probably isn’t going to build a light-rail system in his lifetime, he reasoned. What assets do we have? One of the most successful bike-share programs in the country. The Cultural Trail. The first electric car–share franchise in the country (BlueIndy). Eventually, the Red Line bus rapid-transit system. Uber. What if all of those options were integrated into a single app and payable with a single card? A person could create a profile that indicated what transportation options he would and wouldn’t use, and the app would tell him how to get from his present location to, say, Castleton. Maybe that individual wouldn’t be willing to ride a bike, but would take the Red Line to 86th Street, where an Uber car would be waiting to take him the rest of the way. Perhaps another person would be willing to use the bike share for a distance of less than a mile, where a BlueIndy car would sit reserved for her to drive wherever she pleased. In other words, we might be able to create an infrastructure from what currently exists that would convince more people to leave their cars in the garage.

A few years ago, when Payne began sharing the idea with his confidants, it was a radical concept. Today, a couple of places have something approaching this. Moovel, which bought a startup company from Austin, Ridescout, before it was acquired by the owner of Mercedes last year, sells an app to cities hoping to integrate their transit options. So Payne began thinking about how to take the idea further. What if discounts were offered when road traffic is highest? Would that kind of dynamic pricing encourage ridership? What about people with disabilities? Currently, IndyGo’s small vehicles for those individuals make the service extremely expensive per person. Corporations like Lilly have service vans—used to transport employees between buildings—sitting idle for hours at a time. Could they be tied into this system? Butler University has expressed interest in making their IDs compatible with a universal transit app. Payne even has considered how this would accommodate driverless cars when they come along.

He’ll be the first to admit that he doesn’t have all the details worked out yet. But Payne does have a steering committee, which includes Kathy Davis, an advisor to Mayor Joe Hogsett. She finds the app intriguing, albeit tough to sell. “So much of the economic analysis I read right now talks about individual empowerment as the biggest industry of the next 20 years,” she says. “It’s the growth of the shared economy. This fits right into that. And yet, the idea is abstract. It’s even harder to envision than the Cultural Trail was. You can’t draw a picture of it.”

Another member of the committee, Meredith Klekotka, moved to Indy last year largely because of the Cultural Trail. Payne’s visits to St. Louis, where Klekotka worked for a bicycle and pedestrian advocacy group, convinced her this was the place she needed to be. Now a planner for the Department of Metropolitan Development, she includes the transit app in grant applications. “There’s a lot of energy in this industry, but it’s in its infancy,” she says. “Everyone’s vying to get the best product. If we can get all of the transit providers on board, we can create something next-level.”

That’s Payne’s current challenge. While IndyGo, the bike-share program, and other transit groups have expressed interest, BlueIndy has been tougher to bring to the table. Owned by Bollore, a French company, the electric car–share service will be an essential partner. And as with the Cultural Trail, politics may play a role. Klekotka says former Mayor Greg Ballard loved the transit app idea, but that Hogsett has only received a brief introduction to it.

Payne tends to think in terms of five-year projects, acknowledging that the Cultural Trail took more than 10. So even if he’s successful with his sophomore effort, local riders might not be planning integrated trips on their smartphones until 2020. But resistance to the seemingly unlikely didn’t deter him the first time. “I talk to people who say, ‘You’re an outlier. People don’t want transportation to be an adventure,’” he says. “But plenty of folks agree with me. I recently met a multimillionaire donor who took an Uber to our meeting at Patachou. He owns a Tesla and he left it in the garage. Why? He was curious about the experience. Right now, people like that only amount to 10 percent of the population. But among Millenials? A lot more.”

In addition to the personal mobility app, Payne spends some of his time advancing other ideas, too. Reconnecting to Our Waterways, an initiative of his, aims to clean up and beautify the White River tributaries. His wife, Gail, has an idea for a boardwalk in Broad Ripple that Payne intends to help make happen. And for several years, he has struggled to conceive a project that will address economic inequality here in a significant way. He always returns to transportation, though. Payne believes that how people get from place to place determines how much they interact, which in turn affects quality of life for the entire community.

“Did I mention we’re working on a $100 million idea to take bicycling connectivity into every Indianapolis neighborhood?” he says, almost as an aside. Which sounds crazy. But if you have a few million dollars and an hour for a tour of the Trail he built, Payne will be happy to make you a believer.