Leaning In

Hosted by Trademark Property

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May 2026

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About the show

Leaning In is a podcast exploring the future of mixed-use real estate. Trademark Property Company CEO Terry Montesi, and other executives, speak with experts from various backgrounds and areas to discuss mixed-use, multifamily, and brick-and-mortar retail, and what it looks like to lean into it while others are leaning out. For more information about Trademark, visit www.trademarkproperty.com

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May 11, 2026Episode 354 min

Betting on Physical Retail with Sandeep Mathrani

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 mindsetWhy investing heavily in top-tier malls during downturns created outsized returnsThe real impact of e-commerce on brick and mortar and why omnichannel has strengthened physical retailLessons from turning around WeWork and applying the same operational playbook across industriesWhat separates winning retail assets from those that decline over timeLinks: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

April 20, 2026Episode 21 hr 19 min

Reading the Market with JLL's Mark Gibson

In this episode of Leaning In, Terry Montesi sits down with Mark Gibson to break down the current state of real estate capital markets and what’s actually happening beneath the headlines. Mark shares a data-driven perspective on investor behavior, capital flows, and why many widely discussed risks may be overstated. The conversation covers everything from the return of core capital and shifting investment strategies to the evolving outlook across office, retail, and multifamily sectors. Throughout, Mark emphasizes the importance of focusing on fundamentals, playing through market noise, and structuring investments to withstand uncertainty.They discuss:Why institutional investors are shifting back toward core assets and what that means for pricing and deal flowHow capital availability remains strong, with debt markets wide open and becoming a substitute for asset salesThe resurgence of retail as a top-performing sector and what’s driving tenant expansion and landlord leverageThe multifamily supply cycle, current oversupply dynamics, and why long-term fundamentals still point to strong demandHow office is bifurcating, with top-tier assets thriving while lower-quality inventory faces an uncertain futureThe growing importance of operational excellence and sponsor quality in attracting institutional capitalLinks:Trademark PropertyTerry on LinkedInMark on LinkedInJLL Capital Markets North AmericaTopics:(00:00:00) - Intro(00:01:41) - Mark’s career journey(00:04:21) - Markets playing through noise(00:07:32) - Core capital returns(00:15:39) - Managing systemic risk(00:23:35) - DFW and Sunbelt outlook(00:28:44) - Capitulation and deal flow(00:31:35) - Retail leads the pack(00:34:45) - Multifamily supply reset(00:38:12) - Acquisition versus development(00:39:44) - Loan maturities reality check(00:40:38) - Debt markets(00:46:28) - Mall debt returns(00:47:48) - Retail capital surge(00:50:31) - Retail development subsidies(00:53:02) - Ignore headlines, use data(00:55:48) - Multifamily supply cycle(01:00:42) - Institutional multifamily math(01:02:59) - Office capital returns(01:06:34) - Office culture and AI(01:10:27) - Development risk shifts(01:15:05) - Operational excellence wins(01:16:32) - Career advice and wrap

March 5, 2026Episode 139 min

Decoding Retail Market Trends with JLL’s Monica Mason

Terry Montesi sits down with Monica Mason to explore what is really driving the resurgence of retail real estate investment in the United States. Drawing on her work analyzing capital markets data and investor behavior, Monica explains why retail fundamentals have strengthened in recent years and why institutional investors are increasingly allocating capital to the sector. The conversation unpacks the supply constraints created by post pandemic construction costs, the demographic trends shaping retail demand, and how investors are adapting to a higher interest rate environment. Along the way, Monica shares the data signals that matter most for investors evaluating where retail opportunities are emerging.They discuss:• Why retail investment has grown from 7% of total real estate investment in 2021 to 14% today• How pandemic era construction slowdowns and rising costs created a supply shortage that supports rent growth• Why institutional investors increased retail allocations and what is driving the surge in capital flows• The demographic shifts fueling retail investment across the Southeast and Southwest, including Texas and Arizona• Misconceptions around grocery anchored centers and where investors are beginning to look beyond themLinks:Terry on LinkedInMonica on LinkedInTopics:(00:00:00) - Intro(00:00:23) - Meet Monica at JLL(00:01:47) - Why retail rents are rising(00:09:04) - Misconceptions and headlines(00:11:02) - Demographics and wealth split(00:14:21) - Rate volatility and lending(00:19:27) - How JLL uses data models(00:24:37) - Key 2025 data points(00:26:56) - Grocery anchors and beyond(00:32:06) - Cap rates and where capital goes(00:36:10) - Development outlook(00:38:07) - Why retail wins long term

November 20, 2025Episode 81 hr 2 min

From Dallas to Washington: Ray Washburne on Real Estate, Leadership, and Legacy

Ray Washburne joins host Terry Montesi on Leaning In for an in depth conversation about real estate, leadership, and the evolving landscape of Dallas. Ray reflects on his early entrepreneurial years, the lessons that shaped his investment approach, and the principles that guide his work across sectors from hospitality to mixed use development. He and Terry dive into the transformation of Highland Park Village, the challenges and opportunities within downtown Dallas, and the broader economic signals influencing commercial real estate today.They discuss:Ray’s early path into real estate and the mindset shaped by growing up in DallasThe strategy behind acquiring and revitalizing Highland Park VillageWhy reputation and long term relationships drive success in Dallas and WashingtonThe future of downtown Dallas and major projects that could reshape the cityHow consumer behavior, construction costs, and AI are influencing the real estate cycleChallenges in office, adaptive reuse, and where new opportunities may emergeLinks:Gillon Property GroupTrademark Property Terry on LinkedInAudio Topics(00:00:00) - Intro(00:01:25) - Ray’s career and background(00:04:38) - Leadership philosophy(00:09:23) - Luxury retail and Highland Park Village(00:20:48) - Challenges and future of Dallas real estate(00:23:44) - Downtown Dallas development and vision(00:32:12) - Incentivizing real estate investment(00:36:35) - Shifts in domestic manufacturing and tariffs(00:38:17) - Challenges in real estate development(00:41:19) - Office space and adaptive reuse strategies(00:44:34) - Institutional real estate investment trends(00:49:43) - Creating unique experiences in real estate(00:52:55) - Lessons from public sector experience(00:58:30) - Advice for young real estate professionals

October 13, 2025Episode 747 min

Navigating Retail Real Estate: Insights from Kimco CEO Conor Flynn

In this episode of Leaning In, host Terry Montesi sits down with Conor Flynn, CEO of Kimco Realty, for an in-depth discussion about the evolution of retail real estate, the future of mixed-use development, and the trends shaping consumer behavior. Conor shares lessons from his two decades at Kimco, detailing the company’s strategic shift toward grocery-anchored shopping centers, its multifamily expansion efforts, and the advantages of scale in today’s REIT landscape. The conversation also explores how technology, capital markets, and macroeconomic uncertainty are influencing decisions across the retail and development sectors.They discuss:• Lessons learned from a career built within Kimco Realty• How grocery-anchored centers became the foundation of Kimco’s portfolio• The company’s multifamily strategy and use of joint venture partnerships• Navigating today’s capital markets and managing risk amid uncertainty• Emerging retail trends, from off-price and grocery to health and wellness• How technology and consumer behavior will shape the next generation of shopping centersLinks: Trademark PropertyTerry on LinkedInKimco RealtyConor on LinkedInTopics: (00:00:00) - Intro(00:01:13) - Connor Flynn's journey at Kimco(00:04:09) - Lessons learned in real estate(00:07:44) - Kimco's strategic position and mission(00:15:03) - Multifamily expansion and redevelopment(00:18:07) - Navigating economic uncertainty(00:26:10) - Building for a 300 spread(00:26:30) - Navigating uncertainty in development(00:27:50) - Institutional partnerships and success stories(00:29:29) - Retailer categories and trends(00:30:51) - Grocery anchors and leasing strategies(00:39:04) - National vs. local tenants(00:40:42) - Future of retail real estate(00:45:13) - Advice for young professionals(00:46:57) - Conclusion and final thoughts

July 17, 2025Episode 61 hr 2 min

AI's Influence: Transforming Human Behavior and Retail Dynamics

In this forward-looking episode of Leaning In, Terry Montesi is joined by Bart Higgins and Katie Hillier of Future Perfect X, to explore how artificial intelligence is transforming the future of human behavior, retail, and placemaking. Drawing on their deep backgrounds in design, anthropology, and innovation, Bart and Katie unpack how AI will shift the foundational drivers of consumer experience and commercial real estate. From programmable biology and co-intelligent AI agents to personalized retail journeys and ambient environments, they illustrate what it means to future-proof a business in the age of the "limitless self." This conversation challenges leaders to rethink how places are designed and how brands will maintain emotional relevance in an AI-mediated world.They discuss:Why understanding the future human is more important than understanding the technology itselfHow AI will alter core human traits like identity, emotion, and decision-makingWhy the commercial construct of retail must evolve beyond the needs-based and self-growth economiesWhat the rise of avatars and AI companions means for brand loyalty and physical retailHow retail developers can position themselves as tastemakers in a world of infinite contentThis episode is a must-listen for anyone shaping the future of consumer spaces, brands, or experiences.Topics:(00:00:00) - Intro(00:00:42) - Introducing Bart and Katie(00:04:00) - How does one go about being an innovation consultant?(00:12:34) - How brands and businesses in CRE can future-proof themselves(00:16:19) - How will AI disrupt retail as a business model?(00:23:05) - How is the retail experience going to change as we move forward?(00:27:59) - What are some of the needs consumers are expecting retailers to fill?(00:42:05) - How do you see AI impacting how retail places need to evolve?(00:48:03) - What does the future of retail look like outside of AI?(00:50:36) - Who’s doing a great job of future-proofing themselves?(00:53:53) - Closing questions

June 25, 2025Episode 558 min

The Art of Retail Reinvention: A Conversation with RH’s Steve Rouman

In this episode of Leaning In, Trademark CEO Terry Montesi sits down with Steve Rouman, SVP of Real Estate at RH, to talk about his journey from the landlord side of the business to leading real estate strategy for one of retail’s most design-driven brands.They dive into RH’s transformation into a luxury lifestyle brand, the future of retail site selection, post-COVID consumer behavior, and how physical retail and e-commerce can work together. Steve also shares advice for industry newcomers and why human connection still sits at the heart of retail.🎧 Listen in for a forward-looking take on retail, design, and the evolving role of place.Topics:(00:00:00) - Intro(00:01:12) - Steve’s background and career(00:08:05) - RH's transformation and real estate strategy(00:13:11) - Site selection and unique real estate moves(00:18:02) - Surprises and lessons in retail site selection(00:26:12) - Future growth and expansion plans(00:30:07) - New store concepts and expansions(00:32:40) - AI and the future of retail(00:35:29) - E-commerce and physical retail synergy(00:39:09) - Retailers excelling in brick and mortar(00:44:07) - Future of retail real estate(00:49:24) - Advice for aspiring retail real estate professionals(00:53:13) -Terry’s proudest moments(00:58:05) - Conclusion and final thoughtsLinks:Trademark Property⁠⁠⁠⁠⁠⁠Terry on LinkedInRHSteve on LinkedIn

May 30, 2025Episode 41 hr 0 min

Boom, Bust, or Balancing Act? 2025's Economic Outlook

In this special live episode of Leaning In, Trademark CEO Terry Montesi is joined by returning guest and renowned economist Dr. Peter Linneman to break down what’s shaping the economic landscape as we move through 2025.From inflation and interest rates to capital flows, consumer shifts, and real estate dynamics, Peter offers grounded insights and a healthy dose of perspective on where we’ve been—and where we may be headed.Whether you're navigating strategy in retail, real estate, or simply trying to make sense of a volatile market, this conversation delivers clarity, not noise.🎧 Stream now and follow Leaning In for more conversations on what’s shaping the future of commercial real estate.

April 15, 2025Episode 352 min

Open-Air Retail, Supply-Demand Trends, and What’s Next with DLC's Adam Ifshin

The retail real estate landscape is evolving, and few people understand its intricacies better than Adam Ifshin, Founder and CEO of DLC Management. In this episode, Trademark CEO Terry Montesi sits down with Adam to discuss how value-driven open-air centers, omnichannel innovation, and institutional capital are reshaping the industry.Adam shares insights on why open-air retail continues to outperform, how AI is poised to revolutionize retail operations, and why institutional investors are re-embracing retail real estate. He also dives into the impact of supply and demand dynamics, the future of apparel shopping, and the challenges of new development in today’s market. With over 30 years of experience and a track record of transforming underperforming assets, Adam’s perspective offers a must-listen deep dive into where retail and retail real estate are headed.To stay informed and hear more from top voices in the industry, subscribe to Leaning In and sign up here to be the first to know when a new episode drops!Links: ⁠Trademark Property⁠⁠⁠⁠⁠⁠Terry on LinkedInAdam on LinkedInTopics:(00:05:22) - DLC's Evolution and Core Values (00:11:48) - Investment Strategy and Market Trends (00:16:09) - Pandemic Impact on Retail (00:22:39) - Omnichannel Retail and Future Outlook (00:24:43) - Retailers Must Adapt or Perish (00:25:35) - Bankruptcy and Replacement Tenants (00:27:31) - The Shift to Open-Air Retail (00:30:40) - Consumer Behavior Post-Pandemic (00:32:46) - Interest Rates and Inflation Impact (00:36:31) - Supply and Demand in Retail Real Estate (00:43:23) - The Role of AI in Retail Real Estate (00:45:52) - Future Trends in Retail Real Estate (00:51:04) - Closing Remarks and Final Thoughts

March 21, 2025Episode 248 min

Retail’s Evolution: Malls, Department Stores, and the Road Ahead

The retail world is changing, and two of the biggest names in department stores—Dillard’s and Macy's—are at the forefront. In this episode, Trademark CEO Terry Montesi sits down with the SVPs of Real Estate: Chris Johnson of Dillard's and Chuck DiGiovanna of Macy's, to discuss Retail’s Evolution: Malls, Department Stores, and the Road Ahead.These industry giants share insights into how department stores and malls are adapting to today’s retail landscape, from innovative strategies to the importance of creativity and strong developers.Chris and Chuck also explore the impact of technology, capital markets, and tariffs on the future of retail. With their extensive experience at some of the most recognizable names in retail, this episode is a must-listen for anyone interested in the future of malls, department stores, and the retail industry as a whole.To stay informed and hear from two leaders shaping the future of retail, subscribe to Leaning In and sign up here to be the first to know when a new episode drops!Links: Trademark Property⁠⁠Terry on LinkedInChris on LinkedInChuck on LinkedInTopics: (00:00:00) - Intro(00:01:01) - Chuck and Chris' Journey in Real Estate (00:02:31) - Current State of Macy's and Dillard's (00:03:49) - Challenges and Trends in Retail (00:05:53) - The Future of Malls and Department Stores (00:09:22) - Investment and Redevelopment Opportunities (00:16:18) - The Role of Department Stores Moving Forward (00:24:25) - Navigating Mall Usage Restrictions (00:25:59) - Impact of the Pandemic on Retail (00:29:23) - The Future of Online and Brick-and-Mortar Stores (00:33:07) - Advice for Mall Property Owners (00:37:08) - Challenges in Mall Financing (00:43:37) - Future Trends in Retail and Real Estate (00:47:24) - Closing Thoughts and Opportunities