The Dealmakers’ Edge with A.Y. Strauss

The Dealmakers’ Edge with A.Y. Strauss

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The Dealmakers’ Edge with A.Y. Strauss episodes

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

    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 [email protected] 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
  • Distressed Assets, Real Returns: Exploring Real Estate Risks & Opportunities with Eli Edwards of Fortress Investment Group

    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 [email protected] 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
  • Family Offices & Purpose-Driven Capital: A Conversation with Ron Diamond

    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 [email protected] 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)
    33 min
  • From Caravan to Empire: The Remarkable Ascent of Alfie Best

    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 [email protected] 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)
    32 min
  • Building a Multifamily Platform Through Market Cycles with Ryan Brome

    Ryan Brome is the Chief Operating Officer of Investments at Forum Investment Group, an institutional platform with nearly $6.5 billion in total capitalization. He leads investment management operations across Forum’s development, ownership, and credit businesses, overseeing the investment lifecycle from sourcing through portfolio management and helping align the teams, processes, and risk controls supporting the platform’s growth.

    Ryan has more than 15 years of experience across real estate and capital markets. Before becoming COO of Investments, he served as Forum’s Senior Managing Director and Head of Capital Strategy and previously led Capital Development. Earlier in his career, he held roles at HFF, Real Capital Solutions, and McWhinney, where he served as Vice President of Capital Markets and Investor Relations. He earned a Bachelor of Arts with an emphasis in Finance from the University of Colorado Boulder.


    Insights from Ryan Brome on Multifamily Investing Through Market Cycles

    Multifamily just absorbed one of the largest waves of new supply the country has seen, yet occupancy across Forum Investment Group’s portfolio has climbed from roughly 93% to 95% and 96%. Rent growth is beginning to return, concessions are becoming less necessary, and Ryan Brome sees improving fundamentals even as heavily supplied markets continue to face distress.

    That uneven market requires more than a single investment strategy. Forum has built its platform to move between lending, acquisitions, and development based on where the strongest risk-adjusted opportunities are emerging. The result is a business designed to remain active as different parts of the multifamily cycle open and close.

    In this episode of The Dealmakers’ Edge, Aaron Strauss and Ryan Brome discuss how to read the next phase of the multifamily cycle and how Forum prepared during the downturn to deploy capital as market conditions improve.

    1:29 - Starting in capital markets and entering real estate through HFF

    2:43 - The lunch that led Ryan to Forum Investment Group

    4:38 - How Forum evolved from regional syndication into an institutional platform

    5:38 - Building a multifamily business designed to invest through market cycles

    8:14 - Where multifamily recovery is taking hold and where distress remains

    10:55 - Integrating development, ownership, and credit across the investment team

    13:54 - Why investor demand for 1031 exchanges and DSTs is growing

    19:30 - Building Forum’s infrastructure during the real estate downturn

    22:47 - How experience and organizational culture build resilience through difficult cycles

    25:38 - Why relationships remain the differentiating factor as AI adoption grows


    Mentioned In Building a Multifamily Platform Through Market Cycles with Ryan Brome

    Forum Investment Group | LinkedIn

    Ryan Brome on LinkedIn


    Podcast Disclosures

    This communication is intended for informational purposes only, does not constitute investment advice or a recommendation, and should not provide the basis for any investment decision. Investments in such transactions noted within this communication will be made solely by means of offering materials provided to the recipient by Forum or its affiliates.

    This material does not constitute a part of the offering materials.

    The term “Portfolio” used throughout this communication means Forum’s collection of direct syndication, stabilized multifamily investments; excluding properties sold and acquired during the quarter as well as multifamily developments closed, under construction and in lease-up as of the date of this communication, unless disclosed otherwise within this communication.

    Discussion of 1031 exchanges is for informational and educational purposes only and should not be construed as an offer to sell, or a solicitation of an offer to buy, any security, nor as investment, tax, or legal advice. Individual tax situations vary; please consult your tax professional regarding your specific circumstances.

    Investment in these transactions involves a high degree of risk, and investors should not invest in such transaction unless they can afford to lose their entire investment.

    IN MAKING AN INVESTMENT DECISION INVESTORS MUST RELY ON THEIR OWN EXAMINATION OF THE TRANSACTION AND THE TERMS OF THE OFFERING, INCLUDING THE MERITS AND RISKS INVOLVED. THESE TRANSACTIONS HAVE NOT BEEN RECOMMENDED OR APPROVED BY ANY FEDERAL OR STATE SECURITIES COMMISSION OR REGULATORY AUTHORITY. FURTHERMORE, THESE AUTHORITIES HAVE NOT PASSED UPON THE ACCURACY OR ADEQUACY OF THIS COMMUNICATION.

    ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENSE. THE U.S. SECURITIES AND EXCHANGE COMMISSION DOES NOT PASS UPON THE MERITS OF ANY SECURITIES OFFERED OR THE TERMS OF THE OFFERING, NOR DOES IT PASS UPON THE ACCURACY OR COMPLETENESS OF ANY OFFERING CIRCULAR OR SELLING LITERATURE. 

    INVESTORS SHOULD CAREFULLY CONSIDER THE RISK FACTORS. THE NON- MANAGING MEMBERSHIP INTEREST SHOULD BE PURCHASED ONLY BY INDIVIDUALS FAMILIAR WITH THE CONTENTION OF THESE TRANSACTIONS AND WHO ARE ABLE TO BEAR THE RISKS ASSOCIATED WITH SUCH TRANSACTIONS.

    FORWARD-LOOKING STATEMENTS

    This communication contains certain forward-looking statements that are based on current expectations (but which are not based on any prior operating history). In light of the numerous factors that can materially affect results, including those set forth in this communication, the inclusion of any such forward looking information herein should not be regarded as a representation by Forum, its manager or any other person that the Forum objectives will be achieved. Forward-looking statements contained herein, or other statements made for or on behalf of Forum or their affiliates, from time to time, are not guarantees of future performance and involve certain risks, uncertainties, and assumptions that are difficult to predict. Therefore, actual outcomes and results may differ materially from what is expressed or forecasted in such forward-looking statements.

    Webpage Disclosures

    This podcast is for informational purposes only and should not be used or construed as an offer to sell, a solicitation of an offer to buy, or a recommendation to buy, sell or hold any security, investment, investment strategy, or market sector. This material is intended only to provide a broad market overview for discussion purposes. Discussion of 1031 exchanges is for informational and educational purposes only and should not be construed as an offer to sell, or a solicitation of an offer to buy, any security, nor as investment, tax, or legal advice. Individual tax situations vary; please consult your tax professional regarding your specific circumstances.

    An investor should not construe the contents of this material as legal, tax, investment, or other advice. Investing involves risk, including the possible loss of principal and fluctuation of value. In considering any performance data contained herein, each recipient should bear in mind that past performance is not indicative of future results, and there can be no assurance that an investment program will achieve comparable results or will achieve any projected, estimated, or targeted results. Any projections, market outlooks, or estimates in this podcast are forward- looking statements and are based upon assumptions that are subject to inherent limitations. This podcast reflects our views and opinions as of the date herein. Which are subject to change at any time based on market and other conditions. We disclaim any responsibility to update these views. Any projections, outlooks, or assumptions should not be construed to be indicative of the actual events which will occur.

    Enjoy the show? Have a guest in mind?  Email us at [email protected] 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
  • From Legal Execution to Business Leadership with Andrew Morris

    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 [email protected] 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
  • Strategic Capital Solutions in a Recalibrating Market with Seth Fisher

    Seth Fisher is a Principal and Head of Special Situations at Prime Finance and a member of the firm’s Special Situations Investment Committee. He is responsible for investment, portfolio construction, and asset management activity for the strategy, which Prime now refers to as Strategic Capital Solutions.

    Prior to joining Prime Finance, Seth was Chief Investment Officer of Equity Investments for Starwood Property Trust’s REIS segment, where he led middle-market investment activity tied to CMBS exposure and commercial real estate special situations. Earlier in his career, he held roles across predecessor business lines at LNR Property, including credit investment activities, note sales, and loan workouts. Seth graduated from the Wharton School at the University of Pennsylvania with a B.S. in Economics.


    Insights from Seth Fisher on Strategic Capital Solutions

    A borrower may need a stretched senior loan, preferred equity, mezzanine debt, structured equity, or another capital solution altogether. For Seth Fisher and the team at Prime Finance, the advantage is being able to match the capital structure to the sponsor, the asset, and the situation.

    That flexibility matters in a market where commercial real estate capital structures are still recalibrating for a normalized rate environment. Banks are being more strategic with capital, borrowers are hesitant to lock into long-term fixed-rate debt, and private credit is playing a larger role in how real estate borrowers solve for flexibility. Prime’s rebrand from Special Situations to Strategic Capital Solutions reflects a business that includes secondary loan acquisitions and partnership capital for complex situations.

    In this episode of The Dealmakers’ Edge, Aaron Strauss and Seth Fisher discuss how today’s recapitalization environment is shaping private credit, why Prime shifted from Special Situations to Strategic Capital Solutions, how flexible capital solutions are structured in practice, and why repeat relationships remain central to deal flow, credibility, and execution in commercial real estate.

    1:53 - Learning real estate basics in industrial brokerage

    3:15 - How the GFC shaped Seth’s view of risk and downside protection

    4:14 - Building the three legs of special situations investing

    6:31 - Moving back to Chicago and joining Prime Finance

    7:57 - Strategic Capital Solutions and the specialized platform model

    10:27 - The current era of recapitalization

    16:58 - Rebranding from Special Situations to Strategic Capital Solutions

    21:18 - Building relationships before you need them

    23:18 - Managing stress by breaking problems into smaller pieces


    Mentioned In Strategic Capital Solutions in a Recalibrating Market with Seth Fisher

    Prime Finance | LinkedIn

    Seth Fisher on LinkedIn

    Enjoy the show? Have a guest in mind?  Email us at [email protected] 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
  • Best Of: 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 traditions 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 [email protected] 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)
    32 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 Partners

    Sharon 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 College

    5:05 - Starting in New Jersey with value-add rentals and Airbnb units

    7:05 - Bringing her sons in and committing to a multi-generational development business

    10:50 - The Santa Fe assemblage and why Los Alamos job growth drove the thesis

    12:35 - Spending two years getting to know RCR before structuring the JV

    14:10 - The Hutchinson Island oceanfront assemblage and looking for the right partner

    16:01 - Titusville and a planned JV that converted into a fee builder arrangement

    18:06 - Decision-making rights and negotiating co-developer status

    22:17 - Getting ahead of Opportunity Zone 2.0 before the next designations 

    25:37 - Managing the ups and downs of development over years and decades


    Mentioned In Finding the Right Partners and Building for Generations with Sharon Solomon

    Northlake Development Group | LinkedIn

    Sharon Solomon on LinkedIn

    Enjoy the show? Have a guest in mind?  Email us at [email protected] 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)
    32 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 model

    1:50 - Starting at CBRE and moving to JLL capital markets

    2:16 - Launching Polly Park in 2020 and seeing the pandemic as an opportunity

    2:50 - Financing Hudson Heritage during the pandemic

    3:28 - How brokerage experience at CBRE and JLL shaped the principal mindset

    6:47 - Having $200 million of advisory runway going into the pandemic

    7:55 - Splitting time between merchant banking and co-GP investing

    8:42 - Range of advisory transactions from Tysons Corner to Nashville to Wilmington

    9:59 - Vetting local operators and structuring co-GP deals

    11:34 - Targeting East Coast coastal cities where capital and tenancy understand the product

    12:28 - Equanimity and grounding through the stress of dealmaking

    15:00 - Reading the market and why better days are ahead

    16:52 - Scaling from high-net-worth to institutional capital

    18:39 - Using AI to augment, not replace, human underwriting

    20:22 - Sticking to core markets and what's exciting ahead

    Mentioned In Building a Raising Capital and Co-GP Investing with Abraham Cooper

    Polly Park Capital | LinkedIn

    Abraham Cooper on LinkedIn

    Enjoy the show? Have a guest in mind?  Email us at [email protected] 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)
    23 min

About The Dealmakers’ Edge with 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,…