Ready to deal: New CEO of Flaherty & Collins eager to grow firm

Following stints in Chicago and New York, Robert Flaherty returned to his hometown of Indianapolis two years year to begin working for the company his father started more than 30 years ago.

Now CEO of Flaherty & Collins, he is looking for ways to keep the company nimble and to accelerate opportunities in the real estate development and management sector across the Midwest.

IBJ talked with Flaherty about becoming CEO of a family company, what he learned from his dad and the company’s portfolio.

This interview has been edited for length and clarity.

How have you navigated your return to the company—one where you were known as the boss’s son for most of your life—as you prepared for and assumed the role of CEO?

I knew there would be a lot of expectations attached to rejoining the company with my last name. That’s why I was intentional about how I approached my career path.

I never wanted to come into the organization and immediately be a drain on resources or have a steep learning curve. I really wanted to hit the ground running and be able to add value from day one—just to show that I wasn’t there to take something away but to contribute to what we already do well.

Starting my career in Chicago doing multifamily investment sales at Colliers International gave me great experience, especially on the transactional side. Then I pursued a master’s in real estate development in New York—another major development market—which gave me deeper exposure to the process from a different angle.

How did you work with your dad to return to the company?

After finishing my degree, I thought seriously about staying in New York. It’s an incredible city with a lot of exciting organizations. But I had to ask myself: “If I’m eventually planning to return to Indianapolis, why not now?”

The sooner I got involved with the company, the sooner I could begin making an impact—and the sooner I could get comfortable with our people and processes. As for succession planning, there was never a formal conversation. Honestly, I don’t think my dad will ever fully retire. He loves what he does. His hobby is the deal.

What was it like as a kid to see your father run a company like Flaherty & Collins?

I grew up alongside the company and the real estate industry. It was founded a couple of years before I was born—the same year my brother was born—so I was always an observer of the ups and downs of how my father grew the company and what he went through in doing that.

Some of my early experiences—like witnessing the Great Recession and seeing major projects like Cosmopolitan on the Canal in downtown Indianapolis take shape—gave me early insight.

While I was always inspired by my father’s successes, I also felt a natural hesitancy. When your last name is on the company, there’s often an urge to forge your own path. That was something I wrestled with for a long time.

One summer, I spent time with the development team—my father’s core skill set in the business—and that’s when everything clicked. I fell in love with the process, the buildings themselves, and the people in the organization.

At 29, some might still consider you “green” in the real estate industry. What makes you the right person to take the reins?

That’s a fair question—and I know you won’t be the last person to ask it.

I think what I bring is a fresh perspective and a strong sense of where we can go next. I’m focused on growth, driving value, finding new opportunities and being open to different ways of doing things.

I have a deep respect for the foundation that’s already been built here. I’m not looking to change things just for the sake of change. My goal is to build on what’s working while staying true to our company’s values—and to bring renewed energy and direction to everything we do.

I know I’m young, and I don’t pretend to be a fully formed real estate professional. But I’m OK with that. What matters is showing up every day willing to listen, work hard and grow into the role in a way that benefits the entire organization.

How do you balance your new ideas with the company’s existing expertise—not just for your own development but for the company’s overall benefit?

I think we’ve built a really talented team—on the development, management and construction sides. These are professionals who’ve spent their careers executing and operating complex projects. I don’t see my role as stepping in to change what they do; I see it as enhancing their ability to do it even better.

The goal isn’t to replace what works. It’s to create space for our people to spend more time doing what they do best.

Where do you see the biggest opportunities for the company to grow?

One area I’m especially interested in is strategic joint ventures. Historically, we’ve self-capitalized most of our projects, which has given us more control and ownership. That approach has served us well. But there’s a reason much of the industry is built on joint ventures—they open doors to scale.

We’re hungry for growth across the company. And to me, one of the best ways to achieve meaningful growth over the next several decades is by approaching outside capital more methodically.

Is the joint venture concept something that is key in better positioning the company for long-term success in a volatile development market?

Well, there’s a strong appetite companywide to push the envelope—to ask what we’re capable of and how well we can do it.

To satisfy that ambition, you need scale. And to achieve scale, you often need outside capital.

That doesn’t mean abandoning what we’ve done well. It means keeping our core model intact while supplementing it with new capabilities enabled by outside capital. That could include things like acquisitions—which tend to be capital-intensive—or even expanding into more traditional garden-style developments, which we’ve done less of historically because we’ve focused more on complex public-private projects.

Development is tough right now. We’re all facing headwinds, interest rates are elevated, and construction costs have outpaced revenue growth. But the broader picture remains: There’s still a nationwide housing shortage, and the slowdown in new supply will only make that more pronounced.

Are developers getting the support they need to build downtown? If not, what could be improved?

From my personal experience, and I want to emphasize that this is just my perspective, I think there’s room for improvement—particularly when it comes to clarity and vision.

In other communities, I’ve found it’s often more straightforward to understand what the city wants to see, how projects can get done and what tools or incentives might be available. That clarity makes a big difference when you’re trying to evaluate the risk and feasibility of a project.

Now, to be fair, Indianapolis has collaborated on some exciting recent projects that prove public-private partnerships can work here. That gives me optimism. But I think for outside developers or even local ones evaluating their next move, there’s still a bit of uncertainty. People want to know: If something worked once, can it work again? Is there a consistent strategy?

Investment thrives on stability and predictability. The more clearly the city can articulate its vision and expectations, the more confidence developers will have to pursue big ideas.

Is Flaherty & Collins in a good position with your portfolio mix these days?

I’m really proud of how balanced our portfolio is across both categories (market-rate multifamily and workforce/lower-income rentals), especially on a national level.

That said, most of our market-rate development tends to be focused in the Midwest, which has been a strong region for us. We’ve avoided the oversupply issues that some Sun Belt markets are now dealing with, and we’ve seen steady, healthy economic growth.

In terms of asset class, there’s definitely been a big policy shift toward affordability—and that’s important. But people also need to understand that affordable housing adds a financial gap to a project. If it’s not supported by tax credits or other incentives, that gap has to be covered somehow, and that increases the complexity and cost of getting a deal done.•

— Mickey Shuey

Editor’s note: This story has been updated to correct two errors. Robert Flaherty joined Flaherty & Collins in 2023, and he attended Columbia University in New York City for his master’s degree.