What happens when experience becomes perspective?

Every year, thousands of retail real estate professionals descend on Las Vegas looking for answers.

Where are rents headed? Who's expanding? What's the next opportunity? Which relationships will create the next great deal?

But before the meetings begin and before the convention floor opens, there's a more important question worth asking:

What actually separates the people and companies that consistently outperform everyone else?

Recorded on the eve of ICSC Las Vegas, this special Retail Retold conversation flips the script. Adam Ifshin steps into the host chair and turns the microphone on Chris Ressa, creating a rare opportunity to go beyond the public persona and explore the experiences, decisions, and leadership lessons that shaped his career.

Together, they unpack everything from career-defining pivots and hard-earned management lessons to navigating uncertainty, building high-performing teams, and leading through pressure. The result is a candid conversation about what it takes to grow from dealmaker to operator and why leadership matters more than ever in today's retail real estate environment.

The timing couldn't be better.

Retail real estate is entering a new chapter. Supply remains constrained. Retailers continue to adapt. Landlords are operating from a position of strength. Yet favorable market conditions alone don't create lasting success.

The organizations pulling ahead today are doing something different. They're building teams that trust one another, developing leaders who can perform under pressure, and creating cultures where accountability and ambition coexist.

As the industry gathered in Las Vegas for its biggest week of the year, Adam and Chris explored the principles that drive long-term success on the convention floor, in the boardroom, and across the careers of the people leading the business forward.

The deals made at ICSC mattered.

The people leading them matter even more.

• Why Chris left DLC and what brought him back less than a year later
• The lunch conversation that led to his promotion to COO
• Lessons learned from growing from leasing rep to executive leadership
• The leadership mistake Chris still works on today
• How DLC navigated the uncertainty of COVID without layoffs
• Why culture and trust matter more than real estate expertise alone
• Chris's framework for building teams people want to work for
• The career advice that shaped his approach to leadership and success

00:01 — Adam turns the tables

For the first time, Chris Ressa takes the guest seat as Adam Ifshin steps in as host.

01:56 — Finding the right fit

Chris reflects on his early career and the decision that brought him to DLC.

03:10 — The grass isn't always greener

Why leaving DLC became one of the most important lessons of Chris's career.

05:37 — The second chapter

Returning to DLC creates the foundation for years of growth and leadership.

06:13 — A lunch that changed everything

The unexpected conversation that led to Chris becoming COO.

07:27 — Learning from a different perspective

Chris shares what he's learned from working closely with Adam Ifshin.

09:11 — The leadership mistake that never goes away

The challenge of letting go, delegating, and leading through others.

10:45 — Leading through the unknown

How COVID became a defining moment for DLC's leadership team.

13:26 — The age of the operator

Why execution, culture, and leadership are becoming the industry's greatest differentiators..

14:20 — Building teams people want to run through walls for

Chris's philosophy on trust, accountability, and creating winning teams.

16:43 — The hardest worker in the room

The mindset that shaped Chris's career and leadership style.

18:22 — A personal moment

The story behind introducing Adam to Chris's father and why it mattered.

19:22 — Looking back before looking ahead

Reflections on leadership, mentorship, and the people who shape a career.