Building the Next Generation of a Family Business
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Topics: retail real estate, career pivot, family business dynamics, next generation leadership, personal brand building, due diligence, tenant strategy, site selection, retail economics, internal growth, external networking
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
About Retail Retold:
The Retail Retold Podcast highlights community retailer stories from across the country and gives a behind-the-scenes perspective from business leaders in both retail and real estate industries. The show’s episodes contain valuable insights that help solve the needs of entrepreneurs and real estate pros. Join host Chris Ressa and new guests weekly for amazing insights and thought-provoking stories.