The Dealmakers’ Edge with A.Y. Strauss

A.Y. Strauss
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The Dealmakers’ Edge with A.Y. Strauss dives deep into the world of commercial real estate, bringing you exclusive stories, insights, and strategies from the industry’s top investors, developers, and dealmakers. Hosted by Aaron Strauss, founder and managing partner of A.Y. Strauss, a leading real estate law firm, this podcast offers a behind-the-scenes look at what drives success in commercial real estate. From uncovering the unique edge of industry leaders to exploring the challenges and triumphs they’ve faced, this podcast is a must-listen for commercial real estate investors, developers, brokers, and professionals looking to sharpen their skills and stay ahead in the competitive market.Whether you’re navigating real estate law, structuring deals, or scaling your portfolio, The Dealmakers’ Edge delivers actionable insights and inspiring stories to help you take your career to the next level. Tune in to gain valuable knowledge and discover what it takes to thrive in commercial real estate today.

  1. Scaling Multifamily and Building a Tech-First Lending Solution with Derrick Barker

    MAR 19

    Scaling Multifamily and Building a Tech-First Lending Solution with Derrick Barker

    Derrick Barker is the co-founder and CEO of Nectar, a real estate tech financing company that provides liquidity to commercial real estate sponsors across the country. Nectar has completed more than 140 deals across 29 states, deploying over $40 million to lower middle market and middle market operators who need access to equity trapped in their existing assets. After leaving Goldman Sachs, Derrick built his real estate portfolio to more than 4,700 units and $400 million in asset value across multiple brands, including Civitas Communities, a multifamily platform focused on transforming distressed assets into quality housing, and DOMOS Co-Living, a co-living concept renting larger units by the room. Derrick began buying real estate from his dorm room at Harvard, where he also founded a student organization connected to Wall Street that became his first major business success. After graduating, he spent three years trading complex securities at Goldman Sachs while simultaneously building a 500-unit portfolio in his hometown of Atlanta before leaving to focus on real estate full time. Derrick Barker on Multifamily Growth and Tech-First Lending When Derrick Barker was four days from his earnest money going non-contingent on a Koreatown property, his lender came back short. He had equity sitting across his portfolio at 40% and 50% leverage. He didn't want to refinance. There was no clean way to access it without tripping a covenant. That's the problem Nectar exists to solve. Building Nectar meant becoming a technology company first. Derrick went through Techstars, built AI-native processes from the ground up, and created tools his borrowers use to run their businesses more efficiently. The platform is built to provide both data and liquidity to commercial real estate operators. In this episode of The Dealmakers' Edge, Aaron Strauss and Derrick Barker discuss how he built a multifamily portfolio while trading at Goldman, how Nectar is structured to give sponsors access to trapped equity without tripping existing loan covenants, and why relationships matter more in the age of AI than they ever have. 1:44 - Starting his first business at Harvard and how it connected to Wall Street 3:14 - What it felt like walking onto Goldman's trading floor right after the crisis 5:37 - Why rebuilding the community he grew up in drove his early real estate bets 6:59 - What the Civitas model was built on and why distressed assets were hiding demand 8:07 - How DOMOS Co-Living came out of watching single people navigate shared apartments 11:29 - Being four days from non-contingent earnest money when his lender came back short 13:01 - Why Nectar had to be a technology company  15:39 - Running businesses with his wife since college and what makes it work 17:54 - Why he anchors his identity outside of the next success 19:52 - Keeping his personal life low leverage and cash flowing while taking big swings 21:26 - Why relationships matter more in the age of AI and advice for anyone starting out Nectar | Nectar LinkedIn  Derrick Barker on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    24 min
  2. Pioneering Student Housing and Scaling a Development Business with Jared Hutter

    MAR 5

    Pioneering Student Housing and Scaling a Development Business with Jared Hutter

    Purpose-built student housing wasn't always an institutional asset class. When Jared was tracking the sector in college, two public companies dominated it and most developers hadn't touched it. His first deal in Syracuse required staking out an unresponsive seller on his morning commute just to get a conversation going — and delivered 40% net returns in 18 months when it sold to a publicly traded company. From that first project, deal sizes have grown from $18 million to $100 million-plus, and the capital stack has evolved alongside them. What started with friends-and-family money has shifted toward institutional partnerships as the sector matured and larger players began paying attention. Aptitude has stayed ahead of that curve by sourcing deals directly, doing the heavy lifting on underwriting before ever approaching a capital partner, and being selective about the markets worth betting on. In this episode of The Dealmakers' Edge, Aaron and Jared discuss how he broke into student housing before institutions cared about it, why large state schools are the only markets worth betting on long term, how to design buildings that hold up against 18-to-22-year-old tenants, and the mindset that keeps him steady through the volatility of development. 1:20 - Falling into real estate by accident and discovering entrepreneurship through development 7:19 - The eight-month pursuit of a seller that launched Aptitude’s first project 11:15 - The importance of disciplined land basis and refusing to “lie to yourself” in underwriting 13:58 - Scaling from friends-and-family capital to institutional partnerships 18:10 - The set-up of Aptitude’s executive team and launching an in-house management platform without team bloat 23:19 - Why student housing is operationally intense, but fundamentally durable, and designing for durability with 18-22 year old tenants 28:23 - Competition within the student housing asset class and why large state universities represent a long-term bet on enrollment stability 33:06 - Creating liquidity through quality construction and long-term market selection 34:19 - Jared’s resilient mindset for when things aren’t going well Mentioned In Pioneering Student Housing and Scaling a Development Business with Jared Hutter Aptitude Development | LinkedIn Jared Hutter on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    40 min
  3. Capitalizing on Market Cycles and Office Distress with Jeff Gronning

    FEB 12

    Capitalizing on Market Cycles and Office Distress with Jeff Gronning

    Jeff Gronning is the CEO of Cannon Hill Capital Partners, a vertically integrated real estate private equity firm formed through a management-led buyout of the investment management business of Columbia Property Trust. Prior to founding Cannon Hill, Jeff served as Executive Vice President and Chief Investment Officer at Columbia Property Trust. Before Columbia, Jeff spent 15 years at Normandy Real Estate Partners, where he co-led the growth of a vertically integrated real estate private equity firm. Prior to Normandy, he served as CFO of Morgan Stanley's real estate investing division. Insights from Jeff Gronning on Capitalizing on Market Cycles in Commercial Real Estate After 35 years navigating market cycles from the RTC era through the financial crisis and COVID, Jeff Gronning recognizes the current setup in office real estate. Values are down 40% to 70% from peak, and capital has been flowing away from the sector for years. In late 2025, his firm Cannon Hill Capital Partners announced a partnership with TriPost to acquire up to $1.5 billion in distressed office assets across the Northeast. Jeff's conviction is rooted in what he's lived through before. When the financial crisis hit in 2008, he and his partners at Normandy Real Estate Partners had dry powder and capital markets expertise that allowed them to acquire assets like Boston's John Hancock Tower while the rest of the market stayed frozen. He believes this moment offers the kind of opportunity he hasn't seen in 15-plus years. In this episode of The Dealmakers' Edge, Aaron and Jeff discuss what it takes to stay unflappable through multiple market cycles, why persistence and hard work matter more than timing, and what makes this moment feel like a generational opportunity in distressed office. 1:39 - Growing up in Northern Virginia and starting at Coopers & Lybrand during the RTC era 2:56 - Moving to Morgan Stanley and working on Real Estate Fund No. 1 4:44 - Leaving Morgan Stanley in 2005 to co-found Normandy Real Estate Partners 8:17 - Acquiring defaulted loans and controlling assets like John Hancock Tower 12:06 - Negotiating the Normandy-Columbia merger in late 2019 and closing in January 2020 13:13 - PIMCO's take-private transaction and navigating activist investors 15:24 - Spinning out 55 people to form Cannon Hill Capital Partners 17:12 - Announcing the TriPost Capital Partners strategic partnership in Q4 2025 18:25 - Office values down 40-70% and the opportunity in distressed office 20:19 - Three-part strategy: distressed debt, gap equity, and conversions 24:39 - Developing the mental edge to stay unflappable through market cycles 25:50 - Controlling what you can control and grinding through with persistence Mentioned In Capitalizing on Market Cycles and Office Distress with Jeff Gronning Cannon Hill Capital Partners | LinkedIn  Jeff Gronning on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    30 min
  4. Servant Leadership and Market Dominance with Chad Lavender

    JAN 22

    Servant Leadership and Market Dominance with Chad Lavender

    Chad Lavender is the President of Capital Markets for North America at Newmark. He has more than 15 years of commercial real estate experience, particularly in healthcare and senior housing. Over his career, Chad has completed more than $50 billion in transactions across the U.S., beginning his journey in markets like Alabama and Dallas. Prior to joining Newmark, Chad worked in high-rise development before moving to lead the National Seniors Housing Group at HFF (Holliday Fenoglio Fowler), growing it into the number one senior housing platform in the country. He also worked as an investment advisor with Apartment Realty Advisors’ (ARA)  senior housing group before ARA was acquired by Newmark. Insights from Chad Lavender on Servant Leadership in Capital Markets Chad Lavender leads one of the largest capital markets teams at Newmark. Ask him who he reports to, and he'll point to the advisors on his platform. His job is supporting the people doing deals, helping them hit their goals, and clearing obstacles out of their way. That approach has kept his senior housing team at number one in the country for more than a decade. The same thinking shapes how he works with clients. For two years straight, Chad and his partner Ryan Maconachy told prospects they should refinance their assets instead of selling them. Refinancing didn't generate a commission. Selling did. But refinancing was the right call for those clients at that moment, so that's what Chad recommended. They played for the long term, put client interests ahead of their own revenue, and ended up doubling their business every single year from 2012 to 2019. In this episode of The Dealmakers' Edge, Aaron and Chad discuss what servant leadership actually looks like in a transaction business, why telling clients the truth builds more value than chasing every deal, how market dominance comes from discipline and consistency, and why attitude, effort, and energy are the only variables you can actually control. 2:08 - Growing up in Tuscaloosa with family in real estate and development 3:22 - Running a T-shirt business at Alabama and learning sales 4:02 - Starting in high-rise development in January 2008 as the financial crisis hit 5:16 - Cold-calling 62 groups and asking for introductions, not jobs 6:08 - Working triple duty as an analyst and broker at ARA 7:10 - Launching senior housing with Ryan Maconachy and advising clients to refinance 8:12 - Pitching HFF and doubling revenue every year from 2012 to 2019 9:03 - Maintaining number one market share through COVID 14:16 - Servant leadership and reporting to advisors 19:23 - Controlling attitude, effort, and energy 20:51 - Market outlook across asset classes and emerging opportunities 24:01 - Be forever curious and work relentlessly Mentioned In Servant Leadership and Market Dominance with Chad Lavender Newmark | LinkedIn Chad Lavender on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    25 min
  5. Contrarian Investing and Building for the Long Term with James Ryan

    JAN 8

    Contrarian Investing and Building for the Long Term with James Ryan

    James Ryan founded RYCO Capital in 2018 and has led the firm since its inception. Since establishing the company, James has personally overseen all aspects of its growth and operations. His team has grown and expanded, and he has been a contrarian to great success, acquiring multifamily properties across New York City. Prior to founding RYCO Capital, James held leadership and finance roles across real estate development and early-stage technology firms. He earned his BA in Political Science from Yale University. Insights from James Ryan on Contrarian Investing in New York City Multifamily When New York passed the Housing Stability and Tenant Protection Act in 2019, capital fled the multifamily market overnight. When COVID hit in early 2020, the exodus accelerated. James Ryan saw something different: supply constraints in the tightest housing market in the country, with assets trading at prices that still cash-flowed even if rents stayed flat. RYCO Capital's family office structure gave James an advantage most syndicators don't have - he could say no to deals that didn't make sense and wait for the right opportunities. Between 2020 and 2024, while others stayed on the sidelines, he bought across Brooklyn and Manhattan, raised capital by showing protected downside scenarios, and built a team capable of executing complex, multi-year value-add projects. In this episode of The Dealmakers' Edge, Aaron and James discuss contrarian investing, raising capital without fee pressure, building quality assets that can hold through market cycles, and managing the grind of daily operations while staying focused on long-term goals. 1:40 - Growing up in Rochester and starting in Brooklyn real estate after Yale 3:31 - Family office background in Rochester and buying out father’s partner after a tragic loss 5:33 - Looking at secondary markets in 2019 and finding everything overpriced 6:10 - How the Housing Stability and Tenant Protection Act changed the NYC market overnight 7:35 - Closing on four Brooklyn properties in January 2020 and what happened next 8:48 - The thesis: supply constraints and New York City isn't dead 11:21 - Raising capital and focusing on deals the team believes in 12:28 - Underwriting for downside protection and returning principal to investors 15:38 - Why having institutional backing prevents deal-making adrenaline 18:41 - Building a vertically integrated team that executes at a high level 23:22 - Managing adversity, the daily grind, and staying focused on long-term vision 26:08 - Work-life balance, family time, and avoiding hustle culture Mentioned In Contrarian Investing and Building for the Long Term with James Ryan RYCO Capital | LinkedIn James Ryan on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    28 min
  6. Leading the Future of Affordable Housing with Jason Bordainick

    12/18/2025

    Leading the Future of Affordable Housing with Jason Bordainick

    Jason Bordainick started his first company from a dorm room at the University of Virginia. Off Campus Partners became the nation's largest online marketplace for student housing and was eventually acquired by CoStar. That success gave him credibility, momentum, and the confidence to take on something harder. In 2010, he and his childhood friend Andy Cavaluzzi decided to build a business in affordable housing preservation. Expertise, relationships, and regulatory fluency created steep barriers to entry in the space. They had vision but no track record in the asset class, no institutional backing, and no family real estate firm to lean on. For three and a half years, they submitted proposals, chased deals, and came up just short. That grind built the discipline and partnership that would eventually shape Hudson Valley Property Group into one of the leading platforms in the space. In this episode of The Dealmakers' Edge, Aaron and Jason discuss what it takes to break into a market with high barriers to entry, how to build institutional trust from scratch, and why consistency and execution matter more than having all the answers upfront. Jason shares lessons from proving out a model, earning credibility deal by deal, and leading a business that does well by doing good. 2:57 - Starting Off Campus Partners from a dorm room and winning a business plan competition 4:57 -Teaming up with childhood friend Andy Cavaluzzi to start Hudson Valley Property Group in 2010 6:48 - Understanding capital-A Affordable housing and the role of Section 8 and LIHTC programs 11:49 - Starting with $5,000 and $10,000 checks and compounding investor trust 14:52 - Values-first leadership and how you do anything is how you do everything 16:21 - Using discipline and AI to screen projects and deploy capital at scale 18:16 - Managing adversity and the mental challenges of entrepreneurship 21:14 - How adversity strengthens partnerships and builds equal commitment 23:35 - Career advice for the next generation and the value of specialization Mentioned In Leading the Future of Affordable Housing with Jason Bordainick Hudson Valley Property Group | LinkedIn Jason Bordainick on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    27 min
  7. How Courage and Consistency Close Deals with Henry Stimler

    12/04/2025

    How Courage and Consistency Close Deals with Henry Stimler

    Henry Stimler serves as an Executive Managing Director on Newmark’s Capital Markets Strategies team, where he specializes in originating and structuring in multifamily debt and equity with an emphasis on large bespoke portfolio transactions. Based in the firm’s New York headquarters, Stimler is known for guiding traditional Tri-State investors into new high growth markets across the U.S., including the Midwest, Texas and South Florida, while also sourcing global equity from key international cities like London, Tel Aviv and Johannesburg. Prior to joining Newmark, Stimler founded and served as Director of London Green Capital, a debt origination firm.  Insights from Henry Stimler on How Courage and Consistency Close Deals Henry Stimler runs a full calendar. Client meetings, travel, prospecting, closings, and pipeline follow-ups take up most days, yet he still takes calls from young professionals, makes time for anyone genuinely trying to learn the business, and sees mentorship as part of the job. That mindset was shaped by starting from zero after the 2008 crash. He went from a thriving business to being overdrawn at the ATM and had to rebuild his career piece by piece. It taught him to focus on real opportunities, protect his time and rely on a team where everyone brings a different strength. In this episode of The Dealmakers’ Edge, Aaron talks with Henry about rebuilding from the ground up, sourcing and structuring large multifamily transactions, and keeping deals on track in challenging market conditions. Henry discusses rejection, resilience, mentorship and what it takes to close complex deals. 1:50 – Henry’s background growing up in London and leaving the traditional path 2:35 – Discovering an arbitrage opportunity and building Phoenix 2:50 – The 2008 crash and losing everything, including assets and business 3:20 – Rebuilding through club promotion, opening venues, and returning to finance 3:53 – Turning a shuttered Chinese restaurant into one of NYC’s hottest nightclubs 6:12 – Closing his first deal and earning a $25K commission before his son was born 6:21 – Transition to Newmark when Cantor rolls platforms together 7:03 – Building a national platform and taking NYC investors into new markets 7:57 – Success is not linear and why connection skills drive outcomes 10:51 – How to spot time wasters and protect your capacity 12:12 – “Fish with a net” and why small maybes drain time 14:24 – Making time for students and early-career outreach 16:35 – Keeping a billion-dollar pipeline moving toward closing 18:53 – Team structure in practice and the yin and yang with Bill Weber 21:32 – Developing junior talent and the cold outreach that led to a $230M closing 29:02 – The perspective and humility carried forward from the 2008 crash Mentioned In How Courage and Consistency Close Deals with Henry Stimler Newmark | LinkedIn  Henry Stimler on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    31 min
  8. Navigating Market Cycles and Risk Management with Ran Eliasaf

    11/06/2025

    Navigating Market Cycles and Risk Management with Ran Eliasaf

    Ran Eliasaf is the founder of Northwind Group, a real estate private credit platform based in New York. He founded the firm in 2008 and oversees all investment activity. Throughout his career, Ran has executed more than 300 real estate transactions totaling over $5.5 billion, investing in commercial properties in New York City and healthcare and senior-living properties across the U.S. In 2017, he spearheaded the creation of Northwind’s credit platform and launched the firm’s discretionary closed-ended debt funds, which now manage more than $2 billion in assets. Under Ran’s leadership, Northwind has evolved into an institutional-grade private credit business, investing with a focus on discipline, risk management, and transparency. Before founding Northwind Group, Ran co-founded and served as CEO of a real estate fund that acquired a portfolio of grocery-anchored shopping centers in Florida and Texas. Insights from Ran Eliasaf on Navigating Market Cycles and Risk Management After more than six years in the Israeli Navy as a ship commander, Ran Eliasaf eventually made his way into real estate and founded Northwind Group in 2008. When the financial crisis hit, he was one of the few buyers with liquidity—acquiring distressed debt backed by grocery-anchored assets while most of the market froze. Northwind grew deal by deal for more than a decade before launching its first institutionally backed credit fund in 2020. Today, the firm focuses on middle-market real estate loans, where discipline matters more than upside and one bad loan can wipe out the return of ten good ones. In this episode of The Dealmakers’ Edge, Aaron and Ran discuss how Navy-level discipline translates into private credit, why honesty, integrity, and transparency shape every deal, and the principles Northwind Group relies on to protect capital and outperform through market cycles. 2:03 — Growing up on Israeli Air Force bases and serving over six years as a ship commander 2:58 — Opening a surfing school in the Dominican Republic and returning for law school 3:52 — Launching Northwind Group in 2008 and buying distressed debt during the financial crisis 5:42 — More than a decade of deal-by-deal capitalization before the first credit fund in July 2020 8:14 — Why Northwind Group focuses on $20M–$100M loans and the niche between banks and mega-funds 12:03 — Building a healthcare lending platform and the tech used to underwrite a complex asset class 13:35 — Northwind Group’s core principles: honesty, integrity, and transparency 16:08 — Managing a high-intensity lending environment and why surfing keeps Ran grounded 19:58 — Political risk as a major underwriting factor and why Northwind Group still believes in New York 21:37 — Zero principal losses, never taking back a property, and protecting investor capital Mentioned in Navigating Market Cycles and Risk Management with Ran Eliasaf Northwind Group | LinkedIn  Ran Eliasaf on LinkedIn Enjoy the show? Have a guest in mind?  Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.  Connect with Aaron and the A.Y. Strauss team: Our website (www.AYStrauss.com)  Aaron's website bio page  (Aaron's bio page) Aaron's LinkedIn account (LinkedIn) Our Twitter account (@AYStrauss)

    24 min
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About

The Dealmakers’ Edge with A.Y. Strauss dives deep into the world of commercial real estate, bringing you exclusive stories, insights, and strategies from the industry’s top investors, developers, and dealmakers. Hosted by Aaron Strauss, founder and managing partner of A.Y. Strauss, a leading real estate law firm, this podcast offers a behind-the-scenes look at what drives success in commercial real estate. From uncovering the unique edge of industry leaders to exploring the challenges and triumphs they’ve faced, this podcast is a must-listen for commercial real estate investors, developers, brokers, and professionals looking to sharpen their skills and stay ahead in the competitive market.Whether you’re navigating real estate law, structuring deals, or scaling your portfolio, The Dealmakers’ Edge delivers actionable insights and inspiring stories to help you take your career to the next level. Tune in to gain valuable knowledge and discover what it takes to thrive in commercial real estate today.

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