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