The Dealmakers’ Edge with A.Y. Strauss

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

The Dealmakers’ Edge with A.Y. Strauss is a business podcast hosted by A.Y. Strauss, with 88 episodes on record and a Required Pod Score of 80.

A.Y. Strauss hosts The Dealmakers’ Edge with A.Y. Strauss, a business show with 88 episodes published.

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  Episode #88

  Real Estate Credit & Deal Flow: Finding the Right Opportunities with Sebastian Post

  Oct 1, 202628 min

  Sebastian Post, CFA, is Managing Partner and Co-Head of Investments at Lionheart Strategic Management, where he is responsible for sourcing new investments, capital raising, and managing operations. He also serves on the firm’s Investment Committee. Lionheart invests across real estate credit and equity strategies throughout the United States. Sebastian joined Fisher Brothers in 2011 and was involved in the creation of Lionheart Strategic Management, which launched its third-party fund management business in 2017. Over his tenure, he has worked across the origination and execution of real estate equity and credit investments, helping grow the platform to more than $1 billion in assets under management. Insights from Sebastian Post on Real Estate Credit and Deal Flow There is still strong appetite for real estate credit, but finding the right deals has become the bigger challenge. Sebastian Post sees roughly 1,000 opportunities come across Lionheart Strategic Management’s desk each year, and the firm ultimately closes only about 15 to 20 of them. That selectivity shapes how Sebastian approaches deal flow and underwriting. Lionheart would rather spend another month or two sourcing than force capital into a transaction that does not fit its thesis. The team leans on direct relationships, banks, and brokers to find opportunities, then looks for situations where its development and operating experience can help navigate more complicated transactions without stretching for the last dollar of leverage. In this episode of The Dealmakers’ Edge, Aaron Strauss and Sebastian Post discuss what makes a credit opportunity worth pursuing, why deal flow has become a bigger constraint than capital, how Lionheart approaches complicated construction and transitional loans, and where Sebastian is seeing opportunity in the current market. 1:22 - Joining Fisher Brothers and helping build Lionheart Strategic Management 3:02 - How Lionheart’s deal activity has shifted across market cycles 4:04 - More competition in credit and the move toward whole loan executions 5:26 - Lionheart’s deal size sweet spot and senior banking relationships 7:24 - Why credit capital remains available while equity fundraising stays difficult 10:01 - Where Lionheart’s best deal flow comes from 11:02 - Filtering roughly 1,000 deals down to the opportunities worth pursuing 13:35 - Managing the mental side of dealmaking and delivering bad news fast 15:49 - The Gotham deal and navigating a major construction setback 18:49 - Why Sebastian expects rates to stay higher for longer 22:53 - Revisiting Southern markets and renewed opportunity in California and Chicago 24:47 - Why relationships with your peers compound over a career Mentioned In Real Estate Credit & Deal Flow: Finding the Right Opportunities with Sebastian Post Lionheart Strategic Management | LinkedIn Sebastian Post 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 )

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  Episode #87

  Distressed Assets, Real Returns: Exploring Real Estate Risks & Opportunities with Eli Edwards of Fortress Investment Group

  Sep 17, 202630 min

  Eli Edwards is a Managing Director and Head of Real Estate Equity, US at Fortress Investment Group, based in Menlo Park. Since joining Fortress in 2011, he has focused on opportunistic equity and distressed debt acquisitions across property types and markets throughout the United States. Prior to joining Fortress, Eli worked in real estate investment banking at Barclays and previously worked at Bank of America on defaulted CMBS loans. He received a B.S. in Economics from Duke University, where he graduated Magna Cum Laude. INSIGHTS FROM ELI EDWARDS ON MARKET SELECTION AND INVESTMENT STRATEGY Having the ability to invest across the capital structure creates a different kind of challenge. The opportunity set is broad, so the discipline comes from deciding where the risk is actually worth taking. Eli Edwards has spent years at Fortress making those calls, and one of the clearest lessons from that experience is that distress by itself is not enough. That distinction has shaped where Fortress has been willing to lean in and where it has stayed away. Eli points to Class B office as an area where cheaper pricing did not outweigh weak long-term fundamentals, while San Francisco multifamily and senior housing presented a different setup. In those cases, the short-term disruption came with enough long-term support to justify building a thesis and putting resources behind it. In this episode of The Dealmakers’ Edge, Aaron Strauss and Eli Edwards discuss how Fortress identifies real estate markets and investment themes, why some distressed assets become value traps, where Eli sees opportunity in senior housing and multifamily, and how interest rates and growth factor into equity investment decisions. 1:36 - Starting at Bank of America during the Global Financial Crisis 3:46 - Moving from CMBS servicing to real estate investment banking at Barclays 5:03 - Joining Fortress to move from advising companies to making investment decisions 6:17 - How Fortress evolved across debt, equity, and public real estate investing 9:49 - How Fortress structures its real estate equity team around investment theses 10:40 - Why not all real estate distress creates a good investment opportunity 12:03 - Building the San Francisco multifamily thesis after COVID 14:30 - Finding dislocations before the broader market catches on 15:09 - Why Fortress moved into senior housing and built operational expertise 19:12 - Entering the 1031 exchange and DST market 21:26 - Where Fortress sees multifamily opportunity and why it is avoiding the Sunbelt for DSTs 23:26 - How Eli is thinking about interest rates over the next 6 to 12 months 25:14 - Staying clear-headed through the stress of real estate investing 27:30 - Balancing interest rates and growth when choosing the next investment theme MENTIONED IN DISTRESSED ASSETS, REAL RETURNS: EXPLORING REAL ESTATE RISKS & OPPORTUNITIES WITH ELI EDWARDS OF FORTRESS INVESTMENT GROUP Fortress Investment Group | LinkedIn Eli Edwards 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 )

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  Episode #86

  Family Offices & Purpose-Driven Capital: A Conversation with Ron Diamond

  Sep 3, 202633 min

  Ron Diamond is the Founder and Chairman of Diamond Wealth, a syndicate of more than 100 family offices ranging in size from $250 million to $30 billion, with whom he has invested for more than 20 years. The firm focuses on private markets, including private equity, real estate, venture capital, credit, and special situations. He is also the Founder, Host, and CEO of Family Office World Media and helped create the Family Office Program for TIGER 21. Ron currently serves on the Advisory Board and Steering Committee for the University of Chicago Booth School of Business Family Office Initiative and has taught family office courses at Oxford, Stanford, Harvard, and Chicago Booth. Earlier in his career, Ron founded Pinnacle Capital, a $250 million hedge fund, and held roles at Bear Stearns and Drexel Burnham Lambert. He graduated Magna Cum Laude from Northwestern University with a degree in Economics. Insights from Ron Diamond on Professionalizing Family Offices Ron Diamond has spent more than 20 years investing alongside family offices, and he believes the model has an advantage traditional private equity cannot fully match. Family offices can hold assets longer, avoid the pressure of a fixed exit timeline, and make decisions around long-term compounding instead of a fund clock. The problem is that too few family offices currently have the governance, infrastructure, and execution needed to make that advantage meaningful. That gap is a big part of what Ron is working to change. Through initiatives at Stanford and the University of Chicago Booth School of Business, he has helped build family office education around governance, investing, succession, and best practices. At Booth, that work has grown from a family office course into a broader initiative with an advisory board and conferences designed to bring families together around education rather than pay-to-play deal flow. In this episode of The Dealmakers’ Edge, Aaron Strauss and Ron Diamond discuss why family offices are becoming more important across private markets, how professionalization could help them compete more effectively with private equity, and why better governance and education matter as more wealth moves to the next generation. They also get into the longer-term impact Ron believes family offices could have on how companies are financed and how philanthropic capital is deployed. 1:48 - Starting at Drexel Burnham and launching a hedge fund after its collapse 3:08 - Getting into the family office space 4:39 - How Diamond Wealth aggregates capital across more than 100 family offices 5:53 - Matching investment opportunities with families by asset class 6:40 - How larger family offices source and diligence deals 7:55 - Why family offices can compete differently than private equity 11:10 - Giving business owners a third option beyond private equity or strategic buyers 14:21 - Why professionalization is critical to the future of family offices 15:41 - Building an education-first family office initiative at Stanford 18:10 - Creating the Family Office Initiative at Chicago Booth 21:21 - How family offices could change philanthropy and real-world problem solving 26:12 - Governance, succession planning, and what should happen after a liquidity event 28:35 - How much capital it takes to make a single-family office economically viable 30:22 - The Go-Giver, gratitude, and advice for the next generation Mentioned In Family Offices & Purpose-Driven Capital: A Conversation with Ron Diamond Diamond Wealth | LinkedIn Ron Diamond on LinkedIn The Go-Giver 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 )

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  Episode #85

  From Caravan to Empire: The Remarkable Ascent of Alfie Best

  Aug 21, 202632 min

  Alfie Best is the founder of Wyldecrest Parks, a residential mobile home park operator with 120 parks across the UK. He has built the company into Europe’s largest residential park operator, with a business valued at more than £1.2 billion, and is now planning to establish operations in the United States. Born into a Romani Gypsy family in Leicestershire, Alfie started buying and selling cars and vans at 14. After nearly losing his property portfolio during the 1990 recession, he rebuilt through the mobile phone industry, growing an 18-store business before selling it to a Vodafone subsidiary. He later moved into commercial real estate and purchased his first mobile home park in Essex in 2001. Insights from Alfie Best on Scaling Residential Parks and U.S. Expansion A bad deal or market turn can take more than capital. It can consume your time, cloud your judgment, and leave you unable to think clearly. Alfie Best has been through that position more than once, including the 1990 recession when interest rates doubled, property values fell, and he came close to bankruptcy. His response was not simply to keep pushing in the same direction. Alfie talks about stopping, cutting out outside noise, confronting the worst possible outcomes, and deciding whether the next move is to continue or pivot. That approach helped him rebuild, grow Wyldecrest Parks to 120 locations across the UK, and prepare for the company’s expansion into the United States. In this episode of The Dealmakers’ Edge, Aaron Strauss and Alfie Best discuss rebuilding after financial collapse, knowing when to keep moving and when to pivot, evaluating investments without relying on blind trust, scaling a residential park business, and pursuing growth in the U.S. market. 1:38 - Building Wyldecrest Parks from the ground up 6:05 - Growing up in a Romani Gypsy family and starting in business at 14 7:38 - Building a property portfolio before the 1990 recession 11:17 - Rebuilding through an 18-store mobile phone business 13:22 - Creating an affordable housing model through residential parks 15:06 - Acquiring and redeveloping older park properties 19:01 - Investing with knowledge instead of relying on blind trust 23:34 - Confronting the worst and best outcomes after a bad deal 27:59 - Thinking beyond the next six months when building a business 29:01 - Declaring Wyldecrest the UK’s number one operator with one park Mentioned In From Caravan to Empire: The Remarkable Ascent of Alfie Best Wyldecrest Parks | LinkedIn Alfie Best 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 )

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  Episode #83

  From Legal Execution to Business Leadership with Andrew Morris

  Jul 23, 202625 min

  Andrew Morris is a Managing Director at Blue Owl, where he supports the firm’s Real Assets business as a member of the Legal Team. His work spans the firm’s net lease, real estate credit, and digital infrastructure strategies. Before joining Blue Owl, Andrew served as Associate General Counsel and Chief Compliance Officer at First Eagle Alternative Credit. Earlier in his career, he practiced at Kirkland & Ellis LLP and Davis Polk & Wardwell LLP, advising private fund sponsors on legal, regulatory, fund formation, and capital markets matters. He earned his JD, cum laude, from the University of Pennsylvania Carey Law School and his BA in International Affairs, magna cum laude, from The George Washington University. Insights from Andrew Morris on Moving from Legal Execution to Business Leadership Technical expertise can take someone a long way in commercial real estate. The next level requires something different. Leaders have to understand how the business fits together, how decisions affect multiple stakeholders, and where their team can create value beyond the work immediately in front of them. Andrew Morris has built his career around that broader view. As his role expanded, so did the questions he was responsible for answering. The work became less about executing one transaction or solving one legal issue and more about helping people make better decisions, stay aligned, and move the platform forward. In this episode of The Dealmakers’ Edge, Aaron Strauss and Andrew Morris discuss the shift from technical execution to business leadership, what it takes to earn trust across an investment platform, how leaders manage competing priorities, and why understanding the whole picture matters as responsibilities grow. 1:39 - Starting in finance during the financial crisis and finding his path into investment management 3:08 - Advising fund managers at Kirkland and learning how their businesses operate 4:25 - Moving to Chicago and transitioning from outside counsel to an in-house role 6:18 - Joining Blue Owl after the Oak Street acquisition 8:29 - How the role changes from legal execution to managing people and process 10:06 - Staying focused on durable, income-oriented assets in an uncertain market 11:59 - Where digital infrastructure fits within the mission-critical asset strategy 13:37 - Seeing the whole picture and creating value beyond transaction execution 17:58 - Learning the real estate business and earning trust after joining Blue Owl 19:59 - Why understanding a client’s business is the foundation of trust 21:06 - Building a culture where people feel valued and empowered 22:23 - Developing the next generation as the platform continues to grow Mentioned In From Legal Execution to Business Leadership with Andrew Morris Blue Owl | LinkedIn Andrew Morris 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 )

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