The Allen Family Business Legacy

Photos by Aaron Milbourn and Richard Sitler 

“So, are you a financial advisor, a home builder or a developer?” It’s a question Greg W. Allen (G2) fields regularly, often followed by puzzled expressions when he answers “yes” to all three.

On the south side of Indianapolis, a multigenerational entrepreneurial spirit has been shaping the local landscape for nearly half a century. While many see real estate development, custom home building and wealth management as separate worlds, the Allen family recognizes the common threads that unite them, allowing for continuity across these diverse industries.

“Finance, opportunity recognition, calculated risk taking and, above all, communication – these are the foundational skills that translate across all our businesses,” explains G2. “With exceptional teams in place, deep industry knowledge and the right operating partners, we’re able to execute at a high level across different sectors.”

G2 lives by a simple principle: “Only do what only you can do.” This philosophy guides how he leads his businesses, focusing his personal energy on vision, strategy and relationship building while empowering specialized teams to excel in their areas of expertise.

The Allen family has built not just homes and commercial developments, but also a legacy of service to the Greenwood community through three interconnected businesses: J. Greg Allen Homes, Allen Commercial Group and Wealth Haus. Each operates independently yet benefits from shared vision, values, and the ability to see opportunities others might miss.

South-Side Roots Run Deep

It all began with J. Greg Allen (G1), a Greenwood High School graduate whose passion for home building ignited at age 11 when his father took him to a Home-A-Rama showcase. That spark grew into J. Greg Allen Builder, established in 1976, which quickly earned a reputation for exceptional quality, attention to detail and reasonable pricing.

“I’m a dyed-in-the-wool south sider,” says G1. “Greenwood is home to us and we feel blessed to continue making an impact locally.”

As the custom home building business flourished, G1 followed the natural entrepreneurial path of expansion, venturing into residential development in the 1990s. His vision transformed Johnson County with some of its most iconic neighborhood entrances and distinctive communities.

Building a Commercial Legacy

The evolution continued with the formation of Allen Commercial Group, a vertically integrated commercial real estate development firm. This expansion allowed the Allen family to develop retail shopping centers, medical office buildings for Franciscan, Community Health Network and Indiana Internal Medicine Corp, and spaces for major retailers like Walgreens, Walmart, Target, Ashley Furniture and Stein Mart to name a few.

The numbers tell an impressive story. G1 has built 2,200 homes and 35 residential subdivisions, and developed thousands of acres in Johnson and surrounding counties for residential, retail, medical and office space. The company’s history reflects more than $500,000,000 in completed projects and boasts another $500,000,000 in its current development pipeline. A study once revealed that G1 has made a more significant impact on the property tax rolls for the City of Greenwood than any other individual in history. This remarkable achievement, among others, earned him the prestigious Ernst & Young Entrepreneur of the Year award for the state of Indiana in 1999.

The Next Generation

G2 joined the family business in the early 2000s, learning the commercial side of operations and helping to manage the marketing and leasing division.

“I’ve always felt a strong desire to add value to my family’s businesses, but dad casts a pretty big shadow, so figuring out how and where value was needed was a tall order,” he says. “While we’ve always had tremendous mutual respect for one another, I realized I needed to establish my own expertise in a complementary field before I could make my biggest contribution to the family business.”

The Great Recession and following years were pivotal for the Allen businesses and G2’s career path. As market conditions shifted the family’s business model, G2 pursued another long-term interest: financial planning and investment management.

“The recession created challenges, but also opportunities,” G2 says. “It was the perfect time to develop expertise that could eventually complement our real estate operations.”

Over the next decade, G2 honed his financial planning skills at Morgan Stanley and later Edward Jones, working with clients from all walks of life and at every stage of their financial journey – from young professionals just starting out, to families planning for college and retirement as well as established business owners.

“I made my mark on our family business as a financial advisor during the COVID-19 pandemic by taking full and timely advantage of the then-current estate and gift tax exemption thresholds, and temporary discounts to value of our commercial real estate holdings,” says G2. “We made some pretty sweet lemonade out of the lemons we were dealt and did it within the time frame necessary to avoid significant amounts of future estate tax liability. And that’s when the business model we’re running on today was birthed.”

It was the perfect moment to marry his two worlds, commercial and residential real estate, with sophisticated financial planning.

“My background in both industries allows me to see opportunities and solutions that might not be obvious to others,” says G2.

Bringing It All Together

Central to this success has been G1’s loyal team.

“Taking care of my people is one of the most rewarding aspects of my business today,” G1 often says. This philosophy has cultivated extraordinary loyalty, with several key team members – including John Cunningham, Mike Gordon, Robin Hawhee, Kristi Case, Kristy Speedy and Bob Wildman – each contributing more than 20 years to the business.

To achieve his vision for Wealth Haus, G2 partnered with Clint Heisler, a seasoned CERTIFIED FINANCIAL PLANNER™ with 14 years of experience at Northwestern Mutual. Their complementary strengths – Heisler’s detailed analytical approach and G2’s relationship-building and entrepreneurial skills – created a powerful synergy.

“Our personalities complement each other perfectly,” says Heisler. “I enjoy the singular focus on financial planning and wealth management techniques we bring to our clients, while Greg excels playing in several lanes of traffic at once, and connecting with people and seeing the big picture.”

To achieve the vision for J. Greg Allen Homes, Brandon Poynter, G1’s son-in-law, joined the company as an operating partner specializing in field operations and managing all construction activity. He worked for the company from 1999 to 2010 as a sales associate. He worked in corporate America for the last 15 years while his kids grew up. Once they were all out of the house, he was eager to do something more entrepreneurial.

“Working with family is a perfect match for all,” says Poynter.

Family Business in the Truest Sense

The Allen enterprises are family businesses in every sense of the term. Alicia Cummings, G1’s oldest daughter, serves as chief administrative officer for Wealth Haus and J. Greg Allen Homes. Poynter works as chief construction officer and partner in J. Greg Allen Homes. Even the next generation is already involved, with Avrey Cummings, Alicia’s daughter, working as executive administrator for Heisler at Wealth Haus while studying for her Series 7 and 66 exams.

The extended family and team are equally important to the businesses’ success. Jeanene Christy, G2’s sister-in-law, serves as the interior designer for J. Greg Allen Homes, while Rachel Patterson has been instrumental with branding and marketing for both J. Greg Allen Homes and Wealth Haus. Cam Saylor, the newest addition to the team, brings a unique skill set with dual degrees in finance and informatics from IU, providing valuable input across all three companies.

“These are family businesses but we’re also just a business family,” says G2. “I love what we do and I love the people we do it with. That family feeling extends to everyone on our team.”

Three Businesses, One Integrated Approach

Today, J. Greg Allen Homes, Allen Commercial Group and Wealth Haus operate as independent businesses sharing the same building at 997 East County Line Road in Greenwood. While they function as separate entities, they share common ownership through G2’s involvement in all three, and a unified philosophy centered around long-term success. Each company is supported by dedicated operating partners invested at an ownership level, ensuring operational excellence and stability.

“At Wealth Haus we meet clients exactly where they are in their financial journey,” explains G2.

Their approach is built on providing foundational, fundamental financial advice to people of all ages and at all wealth levels. While G2’s background in real estate certainly informs his perspective, their services span the full spectrum of financial planning, from helping young families build their first budget to guiding retirees through complex estate planning.

“At J. Greg Allen Homes we deliver a one-of-a-kind, custom home building experience that allows our clients the freedom to dream,” says G2.

Through the years they have heard countless stories about the overwhelming nature of custom building a home – the headache of having to be your own architect, your own interior designer and ending up with a product that is only 75% of what was originally desired. It can be disappointing when you end up with a million-dollar white box that looks like every other house in that price range.

“We’re here to change that,” says G2, noting that every custom home should be unique and beautiful in its own right, built perfectly to accompany a family through their current season of life or for a lifetime.

“It’s that belief that drives us to walk alongside our clients and provide all of the resources for them, to sit with them and genuinely hear their wishes and desires,” G2 says.

G2 sees powerful parallels between building a custom home and creating a successful financial strategy. Both processes start with a plan.

“No one has ever hired our home building team and told us to just build whatever we think they need,” G2 says. “We engage in a sophisticated planning process with an architect first, then carry out that plan. The same is true at Wealth Haus. We plan first, then execute.”

The Allen family businesses have each established their own unique identity while maintaining deep roots in the community they’ve served for nearly 50 years.

“Whether you’re dreaming of building a custom home that perfectly reflects your lifestyle, exploring commercial real estate investment opportunities, or seeking personalized financial guidance for your future, the Allen family businesses are ready to welcome you into our extended family of clients,” says G2. “Our multigenerational approach combines decades of expertise with the personal touch that only a family business can provide. We believe that the best relationships are built on trust, communication and shared vision – values that have guided our work for nearly 50 years.”

“Take the first step toward making your dreams a reality by contacting any of our teams today,” G2 adds. “From your first consultation to the completion of your project or financial plan, you’ll experience the difference that comes from working with a business that treats every client like family. Join the Allen family legacy and let’s build something extraordinary together.”

J. Greg Allen Homes: 317-590-6950 or jgregallenhomes.com

Allen Commercial Group: 317-882-7850 or allencommercialgroup.com

Wealth Haus: 317-883-5526 or wealth.haus