Karl Chiao

This transcript has been edited for clarity, readability, and flow. Minor adjustments have been made to remove filler words and improve structure while preserving the original meaning and intent of the conversation.

Henry Harrison:
Welcome to the show, Karl. Thank you for coming on the Entrepreneurs, Business and Finance podcast.

Karl is a very interesting person and a good friend. He has always been deeply involved in the community, and one of the many things that stands out about him is that he is truly a give-back kind of guy.

He also has a diverse background in real estate development and a range of other ventures.

Let’s start with your background. You came to this country as a young boy, went to Texas A&M, and then SMU Law. What was that journey like?

Karl Chiao:
I came to the United States when I was five years old. My parents wanted to build something independently.

Both sides of my family had been part of Chiang Kai-shek’s government in China before relocating to Taiwan. My family had done well there, but my parents wanted to create their own path in America.

We moved to San Antonio, and I didn’t speak English at first. I learned by watching Sesame Street and The Electric Company.

I grew up in San Antonio and eventually went to Texas A&M. I started in aerospace engineering, but that didn’t last long. I switched to political science, partly because of my family’s background in politics.

That led me to SMU Law, and I’ve now been in Dallas for over 30 years.

One skill that really helped me was remembering people. I treated it like collecting baseball cards—I wanted to know who people were, where they were from, and a few key details about them.

Henry Harrison:
You’re also someone who genuinely takes interest in others.

You host a weekly lunch that has been going on for decades, bringing together a wide range of people.

Karl Chiao:
That’s right.

For me, it’s about collecting good people.

That lunch has been going on for about 28 years. It started as an idea inspired by my former father-in-law’s group.

Now it’s a network of 80 to 90 people who come and go depending on availability.

The purpose is not business—it’s connection. If someone treats it like a business-hunting exercise, they usually don’t get invited back.

It’s about building real friendships.

Henry Harrison:
That’s something I appreciate more over time—long-term relationships.

Karl Chiao:
Absolutely.

At one point, I realized I didn’t even know what many of my friends did professionally. They were just my friends.

Later, through tools like LinkedIn, I realized many were CEOs or leaders of major organizations.

That reinforced something important—relationships should be built on genuine connection, not transactions.

Henry Harrison:
Let’s talk about real estate development, particularly your work on the Florida Gulf Coast.

Karl Chiao:
My former father-in-law had built one of the early resorts in Destin.

In the mid-1990s, we decided to develop a golf course in an underdeveloped area of the Florida Panhandle—what was called the Forgotten Coast.

We acquired about 360 acres near Carrabelle, Florida, and built a golf course called St. James Bay.

We sold lots successfully, but in hindsight, we were early.

By the time the 2008 downturn hit, it became clear that holding the remaining assets wasn’t the best move.

That taught me an important lesson: don’t get emotionally attached to a project. If you’ve made your money, sometimes it’s best to move on.

Henry Harrison:
And today, you’re doing something quite different in Dallas.

Karl Chiao:
Yes, office condo development.

We build office parks in growing suburban areas like Prosper, Frisco, and McKinney—places with strong residential growth but limited office space.

The model works because:

• Professionals can own their office space

• They can work closer to home

• We can manage risk by phasing development

Each project is around $20 million, with about $2.5 million in equity and the rest financed through a revolving construction line.

As units sell, we pay down the line, and the later units generate strong profits.

If the market shifts, we can pause development—unlike large office towers, where you must complete the entire project.

Henry Harrison:
That’s a smart, risk-managed approach.

Let’s talk about your involvement with Beta Theta Pi.

Karl Chiao:
That started when I joined the national foundation board.

Over time, I became more involved in the Dallas alumni chapter.

There are about 1,800 Beta alumni in Dallas, but only a small percentage were engaged.

We’ve worked to reenergize the group with events and programming, especially for younger alumni.

One thing I care deeply about is mentorship. Younger men need guidance, accountability, and community.

There’s also a growing focus on mental health, especially after COVID, when many young people experienced isolation.

Henry Harrison:
That’s incredibly important work.

Let’s wrap up with your role at the Dallas Historical Society.

Karl Chiao:
That came out of my experience with Heritage Auctions, where I worked with collections and estates.

The Dallas Historical Society has been around since 1922 and is housed in the Hall of State at Fair Park.

When I stepped into a leadership role, the organization had struggled with turnover and lack of momentum.

Over the past five years:

• We’ve raised more money than in the previous 20

• Grown from 5 to 15 employees

• Acquired major collections, including Tom Landry’s

We’ve also restored the building to reflect its original 1936 design.

What I learned is that nonprofits often need a for-profit mindset—not to change the mission, but to improve execution, fundraising, and growth.

That approach has helped transform the organization into one that is not just surviving, but thriving.

Henry Harrison:
That’s incredibly impressive.

Karl, thank you for sharing your story and for everything you do for the community.

Karl Chiao:
Thank you for having me.

Henry Harrison:
I’ll see you soon.

Karl Chiao:
Sounds great. Thanks, Henry.