In this episode, Terry Montesi sits down with Sandeep Mathrani to unpack a career defined by bold bets, operational discipline, and contrarian thinking in retail real estate. Sandeep shares how he got his start with a single apartment purchase and quickly evolved into a capital markets leader, eventually leading major turnarounds across the industry. The conversation explores his philosophy on investing in physical retail during periods of skepticism, including navigating bankruptcy, the rise of e-commerce, and the evolution of malls into experiential destinations. Sandeep also reflects on his time leading WeWork, drawing parallels between retail and flexible office, and offers a clear framework for evaluating assets, trends, and long-term opportunities.

They discuss:

How Sandeep’s early real estate wins shaped his long-term investment mindset
Why investing heavily in top-tier malls during downturns created outsized returns
The real impact of e-commerce on brick and mortar and why omnichannel has strengthened physical retail
Lessons from turning around WeWork and applying the same operational playbook across industries
What separates winning retail assets from those that decline over time

Links:

Atlas Hills RE - https://www.atlashillre.com/

Sandeep on LinkedIn - https://www.linkedin.com/in/sandeep-mathrani/

Terry on LinkedIn - https://www.linkedin.com/in/terry-montesi/

Trademark Property - https://trademarkproperty.com/

Topics:

(00:00:00) - Intro
(00:00:58) - Early real estate hustle
(00:06:32) - Surviving the retail apocalypse
(00:11:10) - Omnichannel reality checks
(00:16:48) - Boardroom retail lessons
(00:23:11) - Mixed use and sears boxes
(00:27:52) - Retail outlooks
(00:30:27) - Entertainment risk reality
(00:36:17) - Criteria for saving malls
(00:37:18) - Annapolis turnaround play
(00:39:36) - Oakbrook renovation bet
(00:43:03) - Cutting costs fast
(00:45:36) - Flex work
(00:47:19) - Mall liquidity returns
(00:51:31) - Advice for newcomers

Betting on Physical Retail with Sandeep Mathrani

Leaning In

Betting on Physical Retail with Sandeep Mathrani