Building the Next Generation of a Family Business

A different background, and a different lens on retail real estate

Careers aren’t linear. And the best ones usually evolve.

Anya Wolf didn’t start in retail real estate. Her background was in art, including studio work, art history, and hands-on experience in galleries and education. She was fully immersed in a creative path and exploring what that future could look like.

But over time, she gained clarity.

The path forward in the art world is long and highly specialized. Then a loss within her family brought everything into focus. It created urgency and a new perspective on the business side of things. That combination led her to make a decision: step into DLC and understand the investments and platform she had grown up around.

What followed wasn’t a fast track.

She started in a traditional due diligence role. Managing files, answering questions, and supporting transactions. A typical entry point, but one that gave her real exposure to how deals actually get done and how properties are evaluated.

That foundation mattered.

It built a practical understanding of the business, especially around tenant behavior. One of the biggest takeaways is that retail decisions aren’t driven by what consumers want, they’re driven by economics. Rents, incentives, and demographics dictate outcomes, even when demand exists elsewhere.

Now, her focus is evolving again.

After building a strong internal foundation, she’s shifting outward, developing relationships, expanding her network, and bringing new perspectives back into the organization.

Retail remains strong, but interest rate volatility and broader uncertainty are creating friction. Historically, that’s where opportunity shows up.

And for the next generation inside a family business, that matters.

Because this isn’t just about maintaining what was built. It’s about understanding it, evolving it, and ultimately creating your own lane within it.

What You’ll Hear

• Why nontraditional career paths can lead to stronger long-term growth
• How starting in due diligence builds a real understanding of the business
• Why retail decisions are driven by economics, not consumer demand
• How tenants actually evaluate locations and choose markets
• Why asking questions accelerates growth faster than pretending you know
• How to build your own identity inside a family business
• Where the next generation creates value inside an existing platform

Chapters

00:02 – Introduction to Anya Wolf

Background, role at DLC, and how she got here

01:14 – From art to real estate

Starting in art and realizing the limitations of that path

03:24 – The turning point

Family dynamics and the decision to enter the business

09:34 – First role at DLC

What due diligence actually looks like day-to-day

10:48 – Learning the business from scratch

How real estate really works behind the scenes

14:50 – Accelerating growth early on

The power of asking questions and not pretending

18:36 – Shifting from internal to external growth

Why building a network is the next phase

20:19 – State of the retail market

Strength, disruption, and interest rate pressure

25:16 – Building your own identity

Navigating a family business and carving your own lane

29:28 – Rapid fire

Skills, retail nostalgia, and real-life habits