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

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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

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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

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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

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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

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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

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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

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