The Promote Podcast
Episode: Reubens on Rye and Apollo's Divine NNNtervention
Air Date: March 25, 2026
Host: Hiten Samtani (A), with Co-Host Will Krasne (B)
Episode Overview
In this week's episode, Hiten and Will dive into three headline-making commercial real estate (CRE) stories: the tumultuous investing history of David and Simon Rubin; Apollo and Realty Income’s partnership in the triple-net (NNN) world; and the latest mess surrounding J.C. Penney’s real estate trust. With their trademark mix of humor, market insight, and candid industry commentary, they peel back the layers behind some of the sector’s most consequential recent moves and characters.
Key Discussion Points & Insights
1. Punch List: This Week in CRE
(02:10 - 11:09)
a. The Loss of David Simon (02:21 - 03:37)
- David Simon, CEO of Simon Property Group, died at 64.
- Revered for leading the company to become the largest retail REIT globally, with over 200 million square feet.
- Led the firm’s M&A that reshaped it and showed remarkable leadership through Covid and its aftermath.
- Notable anecdote: Simon’s competitive drive referenced via his omission from an Indiana University alumni list.
Memorable Quote:
"He used to work for Perella, the M&A legend, then went and saved his family business, set him up for an IPO and then went on this incredible M&A tear which created the modern Simon Property Group..." — Hiten (02:51)
b. Fannie and Freddie Turbulence (03:37 - 06:42)
- Privatization hopes for Fannie Mae and Freddie Mac led to stock volatility.
- Hosts stress the critical liquidity these agencies provide to the U.S. multifamily/housing markets.
- Current market uncertainty, rising rates, and government policy drift highlighted.
Notable Segment:
"If that guarantee goes away or somehow becomes implicit, what does that eventually mean? ...We're going to hunt and gather. So you don't want to go down that route." — Hiten (04:50)
c. Brookfield’s Office Stumble (06:42 - 08:34)
- Brookfield “deeds in lieu” another troubled office tower (San Francisco).
- In contrast to rivals scoring big wins, Brookfield faces vacancies and poor timing—peak rates, supply chain issues, and adverse market conditions.
d. Implications of the Iran Conflict; GCC Allocator Risk (08:34 - 11:09)
- Recent attack on Qatari LNG shakes confidence—potential to disrupt 17% of exports.
- GCC (Gulf Cooperation Council) nations are heavyweight CRE allocators; disruption threatens global allocation flows.
- The alternative asset industry’s increasing reliance on sovereign wealth, and the tongue-in-cheek summary of market interdependence:
Quote:
"The global economy is predicated on San Francisco lying to New York about how good AI is and then it's New York lying to the Middle East about how safe private credit is." — Hiten (10:45)
2. Profile Deep Dive: The Rubin Brothers
(12:34 - 21:42)
a. Wild Origins and Approach
- David and Simon Rubin, born to a Baghdadi Jewish family in Mumbai, made fortunes across scrap metals, commodities, and politically fraught environments (notably post-Soviet Russia).
- Known for “bare-knuckle business” and thriving where "life is worth less than the ash of this ashtray."
- Avoided Russian oligarch pitfalls despite being non-Russian and Jewish.
Notable Quote:
"You gotta have balls the size of coconuts." — Will (13:15)
"And those things don't necessarily work very well in Russia." — Hiten (14:43)
b. Strategic Exits and Liquidity
- Exited Russia to Abramovich (Chelsea FC fame) for $300M, leaving them highly liquid.
- Built a major UK property and data center portfolio; sold Global Switch (data centers) for $2.5B to Chinese buyers.
Quote:
"Never went broke taking a profit." — Will (16:48)
c. US Moves: Debt/Luxury Asset Plays (16:48 - 21:22)
- Smart entry into US CRE by buying debt (not just property) on iconic Manhattan hotels in the mid-2010s.
- Deployed at least $4B into high-end, distressed US assets from 2020-2022 (often closing quickly, with minimal diligence).
- Recent trophy acquisitions: W South Beach, JW Marriott Turnberry loan, a Central Park supertall inventory loan, and more.
Notable Quote:
"They do it with very little diligence, which is really attractive for a lot of these assets. There’s no committees, there’s no we’re going to take a while to go syndicate this out." — Will (18:15)
d. The “Rubin Reputation” and Succession
- Reputation for being hard-nosed and moving fast; minimal bureaucracy.
- Anecdote from developer Todd Glazier on Rubins' aggressive tactics:
“But the best thing in the world is everybody now knows the Rubin brothers that are coming to town to lend money are hard-ass sons of bitches.” — Todd Glazier (relayed by Hiten, 21:30)
- Succession: David Rubin's son now runs point on major distressed US projects.
3. Market Moves: Apollo & Realty Income’s NNN JV
(22:48 - 28:13)
a. The Structure
- Apollo invests ~$1B in 500 Realty Income triple-net leased (NNN) single-tenant properties.
- Triple-net leases: tenants pay nearly all expenses, creating “mailbox money” for owners—“stay rich” not “get rich” strategy.
Humorous Analogy:
"You've got the nerdy girl and you've got the hot guy over here being like, I can make her the prom queen. And that in this case is Apollo going to Realty Income and saying, let's team up." — Will (22:48)
b. Why JV Now?
- With REITs often trading below NAV, public markets undervalue their real estate ownership—so REITs pivot to generating fee income via asset management JV, not just rent collection.
- Realty Income can recycle capital, diversify income streams, and potentially boost its market multiple.
- Apollo, short on enough traditional debt deals, turns to predictable “bond-like” real estate equity.
- Buyback right for Realty Income at a 6.75% IRR.
Notable Quotes:
"Our size, scale and long standing commitment to providing dependable monthly dividends to investors make this a natural fit with Apollo's insurance capital." — Realty Income CEO Sumit Roy (26:18)
"The game quote really is built around can you originate enough attractive assets to meet your needs? That's why we've been so focused, some might say maniacally focused on really making sure we're building the right type of origination in the right volume." — Apollo Co-President Scott Kleinman (27:12)
c. Broader Trends
- JV-type structures, similar to Realty Income’s deal with Singapore’s GIC, are proliferating: stable, contractual cash flows are highly prized by global capital pools.
4. CRE Battle Royale: JCPenney’s Real Estate Trust Saga
(28:13 - 34:31)
a. Background and Strategy
- JCPenney’s bankruptcy led to creation of a pass-through trust, meant to liquidate 119 stores’ real estate, leased back to a “RemainCo” JCPenney.
- The deal: nearly $1B sale to Onyx Partners (an unknown group with a mysterious “Investment Collaboration for Generational Solutions” tagline).
b. Deal Blows Up: Buyer vs Seller (30:32 - 33:56)
- Onyx failed to close; both parties allege default/bad faith.
- “Dirty estoppels” featured in the dispute: estoppel certificates contain unresolved or undisclosed lease problems, undermining financing and trust between parties.
- Onyx wants their $5M deposit back; Copper Pass-Through Trust wants to keep it and deploy.
Explainer:
"When you buy something and there's a tenant in place, you will have to get...an estoppel...that says...there’s no side deals...the landlord didn't lend you $2 million to pay the rent..." — Will (31:20)
c. Valuation and Repurposing Woes
- Triple net retail, like JCPenney box stores, suffers most when rates rise; hard-to-repurposes stores may be worth substantially less than models suggest.
- Possible future: Trust may take properties public as a REIT instead.
Industry Joke:
“The retail real estate’s littered with the carcass of many an enterprising investor. And I think it’s just claimed potentially two new names…” — Will (34:09)
Notable Quotes & Memorable Moments
-
On the Rubins:
"They are liquid. They're liquid as anybody out there. And their money's not tied up in a company, not tied up in property...ready to go deploy." — Hiten (16:11)
-
On the State of Capital Sourcing:
"The whole alternative asset management industry...it's basically a shark...it has to keep moving forward...they have tapped out. And so they got to go to 401ks...retail...but the biggest fish are these sovereigns." — Will (09:35)
-
On Estoppels:
"Somewhere buried in the lease, this is kosher certificate, basically, right?" — Hiten (31:41)
-
Macro Zinger:
"The global economy is predicated on San Francisco lying to New York about how good AI is and then it's New York lying to the Middle East about how safe private credit is." — Hiten (10:45)
Timestamps for Main Segments
- 00:09 – Opening Banter & Sponsor Shoutouts
- 02:10 – Punch List: Weekly CRE News Run-down
- 12:34 – Rubin Brothers Deep Dive
- 22:48 – Apollo x Realty Income NNN Partnership Breakdown
- 28:13 – JCPenney Trust Sale Fallout
- 34:31 – Wrap Up & Takeaways
Conclusion
This episode is a masterclass in CRE deal-spotting, told with the hosts’ irreverent, insider tone.
- The Rubins: unmatched liquidity and nerve, thriving in chaos, dominating distressed luxury assets.
- Apollo & Realty Income: a landmark JV test-driving CRE’s future as financial product, not just physical asset.
- JCPenney’s Trust: A cautionary tale of retail real estate, documentation drama, and asset repricing in the new rate regime.
Recommended for anyone following high-stakes real estate, capital markets innovations, or just hungry for more “war stories” from the deal trench.