The Dealmakers’ Edge with A.Y. Strauss

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May 2026

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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.

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May 28, 2026Episode 8131 min

Finding the Right Partners and Building for Generations with Sharon Solomon

Sharon Solomon is a principal at Northlake Development Group, a family office development business with a pipeline of residential and multifamily projects across Santa Fe, New Mexico and South Florida. At Northlake, Sharon leads development strategy, capital planning, and partnership structuring, building the firm alongside her two sons as a multi-generational platform.Prior to launching Northlake, Sharon spent 25 years in financial services, including 11 years at RBC Capital Markets, where she served as US Head of Brand and Client Strategy. Before RBC, she was a member of the executive team at Carlin Financial Group and a founder of predecessor firm Nextgen Trading. She began her career as a Product Manager at Goldman Sachs Asset Management. Sharon is a CPA and holds a BS in Accounting from Brooklyn College.Insights from Sharon Solomon on Finding the Right Development PartnersSharon Solomon spent two years getting to know a Dallas-based developer before structuring a JV for a 430-unit multifamily project in Santa Fe. She needed a partner with experience in mountain west markets who was also willing to share decision-making with a family that wanted to be deeply involved. That combination took time to find, and the structure they built together reflects it.Not every project in her pipeline needed that same approach. In Naples, she hired a local developer as a consultant and brought in a builder with deep roots in the market. In Titusville, a planned JV converted into a fee builder arrangement when the structure didn't make sense. The thread across all of them is matching the partnership to what each project actually requires, and making sure the people involved are incentivized well enough to treat it like their own.In this episode of The Dealmakers' Edge, Aaron Strauss and Sharon discuss how she evaluates what kind of partnership each project needs, why cutting a developer's fees can backfire on the project they're building for you, and how she's building a multi-generational development business with her two sons designed to outlast any single deal.1:25 - Growing up in a family of Holocaust survivors and starting at Brooklyn College5:05 - Starting in New Jersey with value-add rentals and Airbnb units7:05 - Bringing her sons in and committing to a multi-generational development business10:50 - The Santa Fe assemblage and why Los Alamos job growth drove the thesis12:35 - Spending two years getting to know RCR before structuring the JV14:10 - The Hutchinson Island oceanfront assemblage and looking for the right partner16:01 - Titusville and a planned JV that converted into a fee builder arrangement18:06 - Decision-making rights and negotiating co-developer status22:17 - Getting ahead of Opportunity Zone 2.0 before the next designations 25:37 - Managing the ups and downs of development over years and decadesMentioned In Finding the Right Partners and Building for Generations with Sharon SolomonNorthlake Development Group | LinkedInSharon Solomon on LinkedInEnjoy 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)

May 14, 2026Episode 8022 min

Raising Capital and Co-GP Investing with Abraham Cooper

When Abraham Cooper left JLL in January 2020 to launch Polly Park Capital, the world shut down within weeks. He saw it as an opening. By summer, he had financed Hudson Heritage, a $65 million construction loan for a ShopRite-anchored mixed-use community in upstate New York and one of the few retail construction loans to close anywhere in the country during the pandemic.Polly Park was built as a merchant bank with two business lines. On the advisory side, Abraham has placed capital for transactions ranging from a $360 million construction financing for a senior living community in Tysons Corner to a $75 million programmatic joint venture for a Wilmington-based operator scaling to 10,000 units. On the principal side, he co-invests alongside local operators on ground-up development, anchored by a high-net-worth partner and focused on the New York tri-state and South Florida.In this episode of The Dealmakers' Edge, Aaron Strauss and Abraham Cooper discuss how Polly Park's merchant banking and co-GP businesses work together, why he targets East Coast coastal cities where capital and tenancy understand the product, how he vets operating partners on co-GP deals, and the grounding that keeps him steady through the stress of dealmaking.1:16 - Polly Park Capital and the merchant bank model1:50 - Starting at CBRE and moving to JLL capital markets2:16 - Launching Polly Park in 2020 and seeing the pandemic as an opportunity2:50 - Financing Hudson Heritage during the pandemic3:28 - How brokerage experience at CBRE and JLL shaped the principal mindset6:47 - Having $200 million of advisory runway going into the pandemic7:55 - Splitting time between merchant banking and co-GP investing8:42 - Range of advisory transactions from Tysons Corner to Nashville to Wilmington9:59 - Vetting local operators and structuring co-GP deals11:34 - Targeting East Coast coastal cities where capital and tenancy understand the product12:28 - Equanimity and grounding through the stress of dealmaking15:00 - Reading the market and why better days are ahead16:52 - Scaling from high-net-worth to institutional capital18:39 - Using AI to augment, not replace, human underwriting20:22 - Sticking to core markets and what's exciting aheadMentioned In Building a Raising Capital and Co-GP Investing with Abraham CooperPolly Park Capital | LinkedInAbraham Cooper on LinkedInEnjoy 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)

April 23, 2026Episode 7934 min

Raising Common Equity and Building an Investor-First Practice with Adam Steinberg

Adam Steinberg is a Principal at Ackman-Ziff Real Estate Group, where he co-heads the equity business and chairs the equity approval committee. Since joining in 2004, Adam has focused exclusively on raising common equity for clients, closing transactions aggregating billions of dollars of capital across traditional and alternative asset classes.Prior to Ackman-Ziff, Adam spent four years as a principal at Partners Group, investing on behalf of an opportunity fund. Before that, he helped build a capital markets group at AEW Capital Management and worked as a capital advisor at Boston Financial Group, which was later acquired by Lend Lease.Adam began his real estate career as a financial analyst in the real estate group at Salomon Brothers during the early 1990s. He holds a degree from Dartmouth College and an MBA from Cornell University.Insights from Adam Steinberg on Raising Common Equity When Ackman-Ziff's equity team evaluates a new assignment, the first question isn't whether the deal is good. It's whether they can win. Adam Steinberg and his partners treat time the way other firms treat capital. It's the scarce resource, and every deal that comes through the door gets measured against the probability of getting it done.The process starts with investors. Before sourcing deals, Adam's team goes to equity partners first, asking what's on their shortlist and what they can actually get through their investment committee. That investor-first approach has pushed the practice into alternative asset classes like powered land, clustered student housing, and solar and battery storage, where risk-adjusted returns are more compelling than in traditional deals.In this episode of The Dealmakers' Edge, Aaron Strauss and Adam Steinberg discuss how the equity advisory business has evolved over two decades, why common equity is harder to raise than preferred, what it takes to get a deal done, and how sponsors can position themselves to attract institutional capital for the first time.3:18 - First real estate job as a financial analyst at Salomon Brothers during the early nineties recession4:23 - Three lessons from Salomon Brothers that still drive how he works today5:36 - Cornell, investment sales, and building a capital markets group at AEW7:30 - Joining Ackman-Ziff in 2004 and growing the equity business10:17 - How the practice evaluates deals and why time is the scarce resource13:06 - Common equity versus preferred and mezzanine15:04 - Reverse engineering deal flow by going to investors first18:22 - Programmatic versus one-off deals and what a successful program requires21:41 - When to stay with friends-and-family capital and when to move to institutional23:26 - Using a recapitalized asset as a seed deal for an institutional partner26:24 - Where the common equity market stands today30:47 - Finding the mental break that forces you fully off the dealMentioned In Raising Common Equity and Building an Investor-First Practice with Adam SteinbergAckman-Ziff Real Estate Group | LinkedInAdam Steinberg on LinkedInEnjoy 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)

April 9, 2026Episode 7845 min

Cannabis Law and Commercial Real Estate with Jennifer Cabrera and Sahar Ayinehsazian

Cannabis is showing up in more CRE conversations than ever, and most of the people having those conversations are figuring it out as they go. The asset class looks familiar enough on the surface that standard deal instincts seem to apply. They rarely do.Jennifer Cabrera and Sahar Ayinehsazian have guided landlords, lenders, and investors through enough of these deals to know where the assumptions break down. The financing options exist but require a different approach to find. The regulatory framework is specific enough that getting local counsel early changes outcomes. And the market is maturing in ways that are creating real opportunity for the people paying attention.In this episode of The Dealmakers' Edge, Aaron Strauss is joined by Jennifer Cabrera and Sahar Ayinehsazian to discuss what landlords need to know before signing a cannabis lease, how lenders are approaching cannabis-related properties, and where the real opportunities are as more state markets mature. For a deeper dive into the regulatory outlook for the year ahead, Jennifer and Sahar are hosting a webinar on April 21st.3:09 - Retail leasing trends and what makes a cannabis-zoned property valuable5:01 - The landlord, lender, and tenant triangle and why transparency with your lender matters8:08 - How to find a bank willing to finance a cannabis-related property9:45 - Financing options for operators and sponsors without institutional backing13:35 - What a cannabis lease actually needs to cover and why standard counsel isn't enough16:03 - Local approval in New Jersey and why planning boards get it wrong19:07 - Building lease exit provisions for regulatory surprises outside anyone's control20:42 - Default post-occupancy and the opportunity a departing cannabis tenant can leave behind23:31 - Why cannabis operators have no bankruptcy protection and what landlords should plan for instead25:56 - The unlicensed market problem and what happened in Los Angeles30:13 - Landlord liability for unlicensed cannabis tenants31:36 - Advertising restrictions for cannabis and what billboard and signage owners need to know34:08 - When to call cannabis counsel and what it actually costs to wait37:29 - Market maturation, the liquor store model, and the hemp beverage loophole closing41:21 - Why market maturation is improving the quality of cannabis investment opportunitiesMentioned In Cannabis Law and Commercial Real Estate with Jennifer Cabrera and Sahar AyinehsazianA.Y. Strauss | LinkedInJennifer Cabrera on LinkedInSahar Ayinehsazian on LinkedInSign up for the April 21st webinar - A.Y. Strauss Presents: The 2026 Cannabinoid Compass: Legal, Compliance & Regulatory ConcernsEnjoy 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)

March 19, 2026Episode 7723 min

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 LendingWhen 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 Street3:14 - What it felt like walking onto Goldman's trading floor right after the crisis5:37 - Why rebuilding the community he grew up in drove his early real estate bets6:59 - What the Civitas model was built on and why distressed assets were hiding demand8:07 - How DOMOS Co-Living came out of watching single people navigate shared apartments11:29 - Being four days from non-contingent earnest money when his lender came back short13:01 - Why Nectar had to be a technology company 15:39 - Running businesses with his wife since college and what makes it work17:54 - Why he anchors his identity outside of the next success19:52 - Keeping his personal life low leverage and cash flowing while taking big swings21:26 - Why relationships matter more in the age of AI and advice for anyone starting outNectar | Nectar LinkedIn Derrick Barker on LinkedInEnjoy 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)

March 5, 2026Episode 7640 min

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 development7:19 - The eight-month pursuit of a seller that launched Aptitude’s first project11:15 - The importance of disciplined land basis and refusing to “lie to yourself” in underwriting13:58 - Scaling from friends-and-family capital to institutional partnerships18:10 - The set-up of Aptitude’s executive team and launching an in-house management platform without team bloat23:19 - Why student housing is operationally intense, but fundamentally durable, and designing for durability with 18-22 year old tenants28:23 - Competition within the student housing asset class and why large state universities represent a long-term bet on enrollment stability33:06 - Creating liquidity through quality construction and long-term market selection34:19 - Jared’s resilient mindset for when things aren’t going wellMentioned In Pioneering Student Housing and Scaling a Development Business with Jared HutterAptitude Development | LinkedInJared Hutter on LinkedInEnjoy 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)

February 12, 2026Episode 7530 min

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 EstateAfter 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 era2:56 - Moving to Morgan Stanley and working on Real Estate Fund No. 14:44 - Leaving Morgan Stanley in 2005 to co-found Normandy Real Estate Partners8:17 - Acquiring defaulted loans and controlling assets like John Hancock Tower12:06 - Negotiating the Normandy-Columbia merger in late 2019 and closing in January 202013:13 - PIMCO's take-private transaction and navigating activist investors15:24 - Spinning out 55 people to form Cannon Hill Capital Partners17:12 - Announcing the TriPost Capital Partners strategic partnership in Q4 202518:25 - Office values down 40-70% and the opportunity in distressed office20:19 - Three-part strategy: distressed debt, gap equity, and conversions24:39 - Developing the mental edge to stay unflappable through market cycles25:50 - Controlling what you can control and grinding through with persistenceMentioned In Capitalizing on Market Cycles and Office Distress with Jeff GronningCannon Hill Capital Partners | LinkedIn Jeff Gronning on LinkedInEnjoy 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)

January 22, 2026Episode 7425 min

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 MarketsChad 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 development3:22 - Running a T-shirt business at Alabama and learning sales4:02 - Starting in high-rise development in January 2008 as the financial crisis hit5:16 - Cold-calling 62 groups and asking for introductions, not jobs6:08 - Working triple duty as an analyst and broker at ARA7:10 - Launching senior housing with Ryan Maconachy and advising clients to refinance8:12 - Pitching HFF and doubling revenue every year from 2012 to 20199:03 - Maintaining number one market share through COVID14:16 - Servant leadership and reporting to advisors19:23 - Controlling attitude, effort, and energy20:51 - Market outlook across asset classes and emerging opportunities24:01 - Be forever curious and work relentlesslyMentioned In Servant Leadership and Market Dominance with Chad LavenderNewmark | LinkedInChad Lavender on LinkedInEnjoy 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)

January 8, 2026Episode 7328 min

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 MultifamilyWhen 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 Yale3:31 - Family office background in Rochester and buying out father’s partner after a tragic loss5:33 - Looking at secondary markets in 2019 and finding everything overpriced6:10 - How the Housing Stability and Tenant Protection Act changed the NYC market overnight7:35 - Closing on four Brooklyn properties in January 2020 and what happened next8:48 - The thesis: supply constraints and New York City isn't dead11:21 - Raising capital and focusing on deals the team believes in12:28 - Underwriting for downside protection and returning principal to investors15:38 - Why having institutional backing prevents deal-making adrenaline18:41 - Building a vertically integrated team that executes at a high level23:22 - Managing adversity, the daily grind, and staying focused on long-term vision26:08 - Work-life balance, family time, and avoiding hustle cultureMentioned In Contrarian Investing and Building for the Long Term with James RyanRYCO Capital | LinkedInJames Ryan on LinkedInEnjoy 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)

December 18, 2025Episode 7226 min

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 competition4:57 -Teaming up with childhood friend Andy Cavaluzzi to start Hudson Valley Property Group in 20106:48 - Understanding capital-A Affordable housing and the role of Section 8 and LIHTC programs11:49 - Starting with $5,000 and $10,000 checks and compounding investor trust14:52 - Values-first leadership and how you do anything is how you do everything16:21 - Using discipline and AI to screen projects and deploy capital at scale18:16 - Managing adversity and the mental challenges of entrepreneurship21:14 - How adversity strengthens partnerships and builds equal commitment23:35 - Career advice for the next generation and the value of specializationMentioned In Leading the Future of Affordable Housing with Jason BordainickHudson Valley Property Group | LinkedInJason Bordainick on LinkedInEnjoy 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)